JP3047538B2 - Novel diamino compound, photoreceptor and electroluminescent device using the diamino compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The diamino compound of the present invention can be used as a light-sensitive material for electrophotography and the like.
Specifically, it can be used as a charge transport material for a photoreceptor or an electroluminescent element.

[0002]

2. Description of the Related Art Various organic compounds which can be used as a light-sensitive material or a charge transport material are conventionally known, for example, anthracene derivatives, anthraquinone derivatives, imidazole derivatives, carbazole derivatives, hydrazone derivatives, styryl derivatives and the like. JP-A-142646 discloses the following general formula:

Embedded image [Wherein R _{1 to} R ₆ represent those described in the above publication], and JP-A-58-58551 discloses the following general formula:

Embedded image [Wherein, R _{1 to} R ₈ represent those described in the above publication]. However, when the above-mentioned materials are applied to, for example, a photoreceptor, it is basically required that they have excellent photosensitivity or charge transportability,
Furthermore, compatibility with other members, durability, weather resistance, and the like are also required, and there is no material that satisfies such characteristics.

[0003]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and has as its object to provide a photoreceptor or an electroluminescent device using a diamino compound different from any of the above structures. I do.

[0004]

Means for Solving the Problems The present invention provides the following general formula [I]:

Embedded image And a photoreceptor having a photosensitive layer containing the diamino compound, and an electroluminescent device containing the diamino compound as a charge transport material.

In the general formula [I], Ar ₁ , Ar ₂ , Ar ₃ ,
Ar ₄ is each independently an alkyl group such as a methyl group or an ethyl group, an aralkyl group such as a benzyl group,
An aryl group such as a phenyl group and a tolyl group; a biphenyl group; and a heterocyclic group such as a residue such as thiophene, furan, and dithiophene, and particularly preferably a biphenyl group.
These groups may have an alkyl group such as a methyl group, an alkoxy group such as a methoxy group, or a substituent such as a phenoxy group or a halogen atom. Particularly preferred Ar _{1 to} Ar ₄ are biphenyl groups having an alkyl group. R ₁ , R ₂ , R
₃ each independently represents a hydrogen atom, an alkyl group such as a methyl group and an ethyl group, an alkoxy group such as a methoxy group and an ethoxy group, and a halogen atom such as Cl and Br. X is -O-, -S- or

Embedded image Represents In Chemical Formula 6, R ₄ and R ₅ each represent a hydrogen atom, an alkyl group such as a methyl group, an ethyl group or a propyl group, or an aryl group such as a phenyl group or a tolyl group, but do not simultaneously take a hydrogen atom.

Specific examples of the compound having a diamino structure represented by the general formula [I] include those having the following structural formulas.

[0007]

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[0008]

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[0009]

Embedded image

[0010]

Embedded image

[0011]

Embedded image

[0012]

Embedded image

[0013]

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[0014]

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[0015]

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[0016]

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Particularly preferred compounds among the above examples are [11],
[16], [18], [19], [25], [28], [29], [30], [36] and [37].

The diamino compound represented by the general formula [I] can be synthesized by the following method. That is, the following general formula [II]:

[0019]

Embedded image [Wherein X and R _{1 to} R ₃ have the same meanings as in general formula [I]] and the following general formulas [III] and [I
V]:

[0020]

Embedded image [Wherein Ar _{1 to} Ar ₄ have the same meanings as in general formula [I]], by synthesizing an amino compound represented by the Ullmann reaction in the presence of a basic compound or a transition metal compound catalyst and a solvent. Can be.

As the basic compound used in the present invention, hydroxides, carbonates, bicarbonates, and alcoholates of alkali metals are generally used, and quaternary ammonium compounds, aliphatic amines and aromatic compounds are used. It is also possible to use organic bases such as amines. Of these, carbonates and bicarbonates of alkali metals and quaternary ammoniums are preferably used. Furthermore, alkali metal carbonates and bicarbonates are most preferred from the viewpoints of reaction rate and thermal stability.

The transition metal or transition metal compound used in the present invention includes, for example, Cu, Fe, Co, Ni, Cr, V, Pd,
Metals such as Pt and Ag and their compounds are used,
Copper and palladium and their compounds are preferred in terms of yield. The copper compound is not particularly limited, and most copper compounds are used, but cuprous iodide, cuprous chloride, cuprous oxide, cuprous bromide, cuprous cyanide, cuprous sulfate ,
Cupric sulfate, cupric chloride, cupric hydroxide, cupric oxide,
Cupric bromide, cupric phosphate, cuprous nitrate, cupric nitrate,
Copper carbonate, cuprous acetate, cupric acetate and the like are preferred. Among them, especially, CuCl, CuCl ₂ , CuBr, CuBr ₂ , CuI, Cu
O, Cu ₂ O, CuSO ₄ , and Cu (OCOCH ₃ ) ₂ are preferred in that they are easily available. As a palladium compound,
A halide, a sulfate, a nitrate, an organic acid salt, or the like can be used. The amount of the transition metal and its compound used is 0.5 to 500 mol% of the halide to be reacted.

The solvent used in the present invention may be any commonly used solvent, but aprotic polar solvents such as nitrobenzene, dimethylformamide, dimethylsulfoxide and N-methylpyrrolidone are preferably used. The reaction of the present invention is generally carried out under normal pressure at 100 to 250.
The reaction is carried out at a temperature of ° C., but may be carried out under pressure. After the completion of the reaction, a solid substance precipitated in the reaction solution is removed, and then the solvent is removed to obtain a product.

The diamino compound represented by the general formula [I] can be used as a photosensitive material for a photoreceptor, particularly as a charge transporting substance. Further, it can be used for a charge transporting layer of an electroluminescent element by utilizing its charge transporting property. First, a case where the diamino compound represented by the general formula [I] is used as a charge transport layer of a photoreceptor will be described. The photoreceptor of the invention has a photosensitive layer containing one or more diamino compounds represented by the general formula [I].
The diamino compound represented by the general formula [I] is particularly excellent in charge transportability.

As the photoreceptor, various types of photoreceptors are known, and the photoreceptor of the present invention may be in any of these forms. For example, a single-layer photoreceptor having a photosensitive layer formed by dispersing a charge generating material and a charge transport material in a resin binder on a support, or a charge generating layer having a charge generating material as a main component is provided on a support. And a so-called laminated photoreceptor provided with a charge transport layer thereon.

The diamino compound of the present invention acts as a charge transporting substance in a photoreceptor, and can transport a charge carrier generated by absorbing light extremely efficiently.
Further, the diamino compound of the present invention is excellent in light stability, hardly oxidized because it does not have an olefin double bond in the molecule, has good ozone resistance, and has excellent durability that can withstand repeated use. A photoreceptor can be obtained. Further, the diamino compound of the present invention has good compatibility with a binder resin, and can provide a photoconductor having excellent sensitivity and repetition characteristics.

As the charge generating material, bisazo pigments,
Triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes, cyanine dyes, styryl dyes, pyrylium dyes, azo pigments, quinacridone pigments, indigo pigments, perylene pigments, polycyclic quinones Organic substances such as pigments, bisbenzimidazole pigments, indathrone pigments, squarium salt pigments, azulene pigments, phthalocyanine pigments, pyrrolopyrrole pigments, and selenium alloys such as selenium, selenium / tellurium, selenium / arsenic, and sulfide Inorganic substances such as cadmium, cadmium selenide, zinc oxide, and amorphous silicon are exemplified.
In addition, any material that absorbs light and generates charge carriers at an extremely high probability can be used.

Examples of suitable binder resins include, but are not limited to, saturated polyester resins, polyamide resins, acrylic resins, ethylene-vinyl acetate resins, ionically crosslinked olefin copolymers (ionomers), styrene −
Thermoplastic resins such as butadiene block copolymer, polycarbonate, vinyl chloride-vinyl acetate copolymer, cellulose ester, polyimide, and styrene resin; epoxy resin, urethane resin, silicone resin, phenol resin, melamine resin, xylene resin, and alkyd resin Thermosetting resin such as thermosetting acrylic resin; photocurable resin; and photoconductive resin such as polyvinyl carbazole, polyvinyl pyrene, polyvinyl anthracene, and polyvinyl pyrrole. These can be used alone or in combination. These electrically insulating resins were measured alone to be 1 × 10
It is desirable to have a volume resistance of ¹² Ω · cm or more.

In order to manufacture a single-layer type photoreceptor, fine particles of a charge generating material are dispersed in a resin solution or a solution in which a charge transporting material and a resin are dissolved, and this is coated on a conductive support and dried. Good. At this time, the thickness of the photosensitive layer is 3 to 3
0 μm, preferably 5 to 20 μm. If the amount of the charge generating material used is too small, the sensitivity is poor, and if it is too large, the chargeability is deteriorated, the mechanical strength of the photosensitive layer is reduced, and the proportion in the photosensitive layer is 1 part by weight of the resin. 0.
The range is from 0.01 to 2 parts by weight, preferably from 0.2 to 1.2 parts by weight. The diamino compound represented by the general formula [I] as the charge transporting material is 0.01 to 1 part by weight of the binder resin.
To 2 parts by weight, preferably 0.2 to 1.5 parts by weight.
When the amount is less than 0.01 part by weight, the sensitivity is poor. When the amount is more than 2 parts by weight, the functional strength of the photosensitive layer is weakened and the repetition characteristics are deteriorated.

In order to prepare a laminated photoreceptor, a charge generation material is vacuum-deposited on a conductive support, or dissolved in an appropriate solvent and applied, or a pigment is applied to an appropriate solvent or an appropriate solvent. For example, it is obtained by applying and drying a coating solution prepared by dispersing in a solution in which a binder resin is dissolved, and then applying and drying a solution containing a charge transport material and a binder resin thereon. At this time, the thickness of the charge generation layer is 4 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer is 3 to 5 μm.
0 μm, preferably 5 to 30 μm. The ratio of the charge transport material in the charge transport layer was 0.2 with respect to 1 part by weight of the binder resin.
To 2 parts by weight, preferably 0.3 to 1.3 parts by weight.

The photoreceptor of the present invention can be used together with a binder resin together with a plasticizer such as halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, dibutyl phthalate, O-terphenyl, chloranyl, tetracyanoethylene, 2,4,7.
An electron-withdrawing sensitizer such as trinitrofluorenone, 5,6-dicyanobenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid, methyl violet, rhodamine B, cyanine dye, pyrylium salt And sensitizers such as thiapyrylium salts. As the electrically insulating binder resin used in the present invention, a binder such as a thermoplastic resin or a thermosetting resin, a photocurable resin, a photoconductive resin, or the like, which is known as an electric insulator, is used. it can. As the conductive support used in the photoreceptor of the present invention, copper, aluminum, silver,
Sheets or drums of iron or nickel foil or plate are used, or these metals are vacuum-deposited or electroless-plated on plastic films, etc., or conductive polymers, indium oxide, tin oxide And a layer of a conductive compound, such as a paper or a plastic film, provided by coating or vapor deposition.

FIGS. 1 to 5 schematically show examples of the constitution of a photoreceptor using the diamino compound of the present invention. Figure 1 shows the substrate
(1) A photoreceptor having a photosensitive layer (4) formed by mixing a photocharge generating material (3) and a charge transporting material (2) with a binder, wherein the diamino compound of the present invention is used as a charge transporting material. Used. FIG. 2 shows a function-separated type photoreceptor having a charge generation layer (6) as a photosensitive layer and a charge transport layer (5).
The charge transport layer (5) is formed on the surface of (6). The charge transport layer (5) contains the diamino compound of the present invention. FIG. 3 shows a function-separated type photoreceptor having a charge generation layer (6) and a charge transport layer (5) as in FIG. 2, but the charge transfer layer (5) has a surface opposite to FIG. A generation layer (6) is formed. FIG. 4 shows a surface protective layer on the surface of the photoreceptor of FIG.
(7), and the photosensitive layer (4) is a charge generating layer (6).
And a function-separated type photoconductor having a charge transport layer (5). FIG. 5 shows an intermediate layer between the substrate (1) and the photosensitive layer (4).
(8), the intermediate layer (8) has improved adhesion,
It can be provided to improve coatability, protect the substrate, and improve charge injection from the substrate to the photosensitive layer.

As the material used for the intermediate layer, polyimide, polyamide, nitrocellulose, polyvinyl butyral, polyvinyl alcohol, aluminum oxide and the like are suitable, and the film thickness is desirably 1 μm or less.

The diamino compound represented by the general formula [I] of the present invention can be applied to a charge transport layer of an electroluminescence device by utilizing its charge transport property. Hereinafter, a case where the diamino compound of the present invention is applied to a charge transport layer of an electroluminescent device will be described. The organic electroluminescence element is composed of at least an organic light emitting layer and a charge transport layer containing a diamino compound between electrodes. FIG. 6 schematically shows an electroluminescent element. In the figure, (11) is an anode, on which a charge transport layer is provided.
(12), an organic light emitting layer (13) and a cathode (14) are sequentially laminated, and the charge transport layer has the general formula
It contains the diamino compound represented by [I]. Anode (1
By applying a voltage to 1) and the cathode (14), the organic light emitting layer (13) develops color.

Anode of organic electroluminescence element
As the conductive material used as (11), those having a work function of more than 4 eV are preferable, and carbon, aluminum, vanadium, iron, cobalt, nickel, copper, zinc,
Tungsten, silver, tin, gold and their alloys,
Tin oxide and indium oxide are used. The metal forming the cathode 14 preferably has a work function of less than 4 eV, and magnesium, calcium, titanium, yttrium, lithium, gadolinium, ytterbium, ruthenium, manganese, and alloys thereof are used. In the organic electroluminescence element, at least the anode (11) or the cathode (14) is a transparent electrode so that light emission can be seen. At this time, if a transparent electrode is used for the cathode, the transparency is likely to be impaired. Therefore, it is preferable to use the anode as the transparent electrode. In the case of forming a transparent electrode, a conductive material as described above may be formed on a transparent substrate by means of vapor deposition, sputtering, or the like so as to secure a desired light-transmitting property. As a transparent substrate, it has a moderate strength, when producing an electroluminescent element,
It is not adversely affected by heat due to vapor deposition and the like, and is not particularly limited as long as it is transparent.Examples of such a material include a glass substrate and a transparent resin such as polyethylene, polypropylene, polyether sulfone, and polyether ether ketone. It is also possible to use. As a transparent electrode formed on a glass substrate, commercially available products such as ITO and NESA are known, and those may be used.

The charge transport layer (12) is made of the above-mentioned general formula [I]
May be formed by vapor deposition, or may be formed by spin coating an appropriate resin solution of the diamino compound. When formed by a vapor deposition method, the thickness is usually 0.01 to 0.3 μm. When formed by a spin coating method, the diamino compound is added to the binder resin by 2 μm.
The thickness is set to about 0.0 to 80% by weight so that
The thickness may be about 5 to 1.0 μm.

An organic light emitting layer is formed on the charge transport layer (12) formed as described above. As the organic light-emitting material used for the organic light-emitting layer, known materials can be used. For example, epidolidine, 2,5-bis [5,7-di-t-pentyl-2-benzoxazolyl] thiophene, 2,2′- (1,
4-phenylenedivinylene) bisbenzothiazole, 2,
2 ′-(4,4′-biphenylene) bisbenzothiazole,
5-methyl-2- {2- [4- (5-methyl-2-benzoxazolyl) phenyl] vinyl} benzoxazole,
5-bis (5-methyl-2-benzoxazolyl) thiophene, anthracene, naphthalene, phenanthrene, pyrene, chrysene, perylene, perinone, 1,4-diphenylbutadiene, tetraphenylbutadiene, coumarin,
Macridine stilbene, 2- (4-biphenyl) -6-phenylbenzoxazole, aluminum trisoxine, magnesium bisoxin, bis (benzo-8-quinolinol) zinc, bis (2-methyl-8quinolinolate) aluminum oxide, indium tris Oxine, aluminum tris (5-methyloxin), lithium oxine, gallium trioxin, calcium bis
(5-chlorooxin), polyzinc-bis (8-hydroxy-5-quinolinonyl) methane) dilithium epindridione, zinc bisoxin, 1,2-phthaloperinone,
Examples thereof include 2-naphthaloperinone. Also, common fluorescent dyes such as fluorescent coumarin dye, fluorescent perylene dye, fluorescent pyran dye, fluorescent thiopyran dye,
Fluorescent polymethine dyes, fluorescent merocyanine dyes, fluorescent imidazole dyes and the like can also be used. Among them, particularly preferred are chelated oxinoid compounds.

The organic light-emitting layer may have a single-layer structure of the above-described light-emitting substance, or may have a multi-layer structure in order to adjust characteristics such as light emission color and light emission intensity. Next, the above-described cathode is formed on the organic light emitting layer.

As described above, the charge transport layer (12) is formed on the anode (11).
The case where the light emitting layer (13) and the cathode (14) are sequentially laminated to form an organic luminescence element has been described.
A light emitting layer (13), a charge transport layer (12) and an anode may be sequentially laminated on (14). One set of transparent electrodes is made of a suitable lead wire (15) such as nichrome wire, gold wire, copper wire, platinum wire, etc.
And the organic luminescence element is connected to both electrodes with an appropriate voltage.
Light is emitted by applying (Vs). The organic electroluminescence device of the present invention is applicable to various display devices, display devices, and the like.

[0040]

EXAMPLES The photoreceptor of the present invention will be described in more detail with reference to Examples and Comparative Examples. In the following examples, “parts” means “parts by weight” unless otherwise specified.

Example 1 Disazo compound represented by the following general formula [A]

Embedded image 0.45 parts and 0.45 parts of a polyester resin (Vylon 200; manufactured by Toyobo Co., Ltd.) were dispersed together with 50 parts of cyclohexanone by a sand grinder. Using a film applicator, apply 0.3 g of the obtained dispersion of the disazo compound on an aluminized mylar having a thickness of 100 μm.
/ m ² and dried.

On the charge generation layer thus obtained, 70 parts of a diamino compound [2] and a polycarbonate resin
(Panlite K-1300; manufactured by Teijin Chemicals Ltd.)
-A solution dissolved in 400 parts of dioxane was dried to a film thickness of 16
It was applied to a thickness of μm and dried to form a charge transport layer. Thus, an electrophotographic photoreceptor having two photosensitive layers was obtained.

The photoreceptor thus obtained was subjected to a commercially available electrophotographic copying machine (EP-470Z, manufactured by Minolta Camera Co., Ltd.).
Corona charging at −6 Kv, initial surface potential V ₀ (V), exposure amount E _1/2 (lux · se
c) Decay rate DD of initial potential when left in the dark for 1 second
R ₁ (%) was measured.

Examples 2 to 4 In the same manner as in Example 1, but with the same constitution, except that diamino compound [2] used in Example 1 was replaced with diamino compounds [5], [6] and [7] Were prepared respectively. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 5 Disazo compound represented by the following general formula [B]

Embedded image 0.45 parts, polystyrene resin (molecular weight 40000) 0.4
5 parts were dispersed together with 50 parts of cyclohexanone by a sand grinder.

The obtained dispersion of the bisazo compound was applied to a thickness of 1
Using a film applicator, the film was applied on a 00 μm aluminized mylar using a film applicator to a dry film thickness of 0.3 g / m ² and then dried. A solution obtained by dissolving 70 parts of the diamino compound [10] and 70 parts of a polyarylate resin (U-100; manufactured by Unitika) in 400 parts of 1,4-dioxane is obtained on the charge generation layer thus obtained. It was applied to a thickness of 16 μm and dried to form a charge transport layer. Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was produced.

Examples 6 to 8 In the same manner as in Example 5, but having the same constitution, except that the diamino compound [10] used in Example 5 was replaced with diamino compounds [11], [13], and [16] Were prepared respectively. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 9 Polycyclic quinone pigment represented by the following general formula [C]

[0049]

Embedded image 0.45 parts, polycarbonate resin (Panlite K-13
000: Teijin Chemicals Ltd.) 0.45 parts of dichloroethane 50
With a sand grinder. The resulting dispersion of the polycyclic quinone pigment was applied onto an aluminized mylar having a thickness of 100 μm using a film applicator so that the dry film thickness became 0.4 g / m ^2, and then dried.
On the charge generation layer thus obtained, 60 parts of a diamino compound [17] and a polyarylate resin (U-100;
A solution prepared by dissolving 50 parts of 400 parts of 1,4-dioxane (manufactured by Unitika Ltd.) was applied so that the dry film thickness became 18 μm,
It was dried to form a charge transport layer. Thus, 2
An electrophotographic photoreceptor having a photosensitive layer composed of layers was prepared.

Examples 10 to 11 In the same manner as in Example 9, except that the diamino compounds [18] and [25] were used in place of the diamino compound [17] used in Example 9, respectively. The body was made. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 12 A perylene pigment represented by the following general formula [D]

Embedded image 0.45 part and 0.45 part of butyral resin (BX-1; manufactured by Sekisui Chemical Co., Ltd.) were dispersed together with 50 parts of dichloroethane by a sand mill. The resulting perylene pigment dispersion was applied on a 100 μm-thick aluminized mylar using a film applicator so that the dry film thickness was 0.4 g / m ^2, and then dried. 50 parts of a diamino compound [26] and 50 parts of a polycarbonate resin (PC-Z; manufactured by Mitsubishi Gas Chemical Co., Ltd.) were placed on the charge generation layer obtained in this manner.
A solution dissolved in 400 parts of 4-dioxane has a dry film thickness of 1
It was applied so as to have a thickness of 8 μm to form a charge transport layer. Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was produced.

Examples 13 to 14 The same method as in Example 12, except that the diamino compound [28] and [29] were used in place of the diamino compound [26] used in Example 12, respectively. The body was made. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 15 0.45 part of titanyl phthalocyanine, butyral resin (B
X-1; manufactured by Sekisui Chemical Co., Ltd.) was dispersed in a sand grinder together with 50 parts of dichloroethane.
The dispersion of the obtained phthalocyanine pigment was 100 μm thick.
Was applied using a film applicator to a dry film thickness of 0.3 g / m ² and then dried. On the charge generation layer thus obtained, 50 parts of a diamino compound [31] and a polycarbonate resin (P
A solution prepared by dissolving 50 parts of CZ (manufactured by Mitsubishi Gas Chemical Co., Ltd.) in 400 parts of 1,4-dioxane was applied to a dry film thickness of 18 μm to form a charge transport layer. In this way,
An electrophotographic photoreceptor having two photosensitive layers was prepared.

Examples 16 to 17 In the same manner as in Example 15, except that the diamino compounds [36] and [37] were used instead of the diamino compound [31] used in Example 15, respectively. The body was made. The thus obtained photosensitive member was measured _{V 0, E 1/2,} DDR 1 in the same manner as in Example 1.

Example 18 50 parts of copper phthalocyanine and 0.2 part of tetranitro copper phthalocyanine were dissolved in 500 parts of 98% concentrated sulfuric acid with sufficient stirring, and the mixture was poured into 5000 parts of water, and the photoconductivity of copper phthalocyanine and tetranitro copper phthalocyanine was changed. After precipitating the conductive material composition, it was filtered, washed with water, and dried at 120 ° C. under reduced pressure. 10 parts of the photoconductive composition thus obtained was mixed with 22.5 parts of a thermosetting acrylic resin (Acrydic A405; manufactured by Dainippon Ink) and a melamine resin (Super Beckamine J).
820; manufactured by Dainippon Ink and the like, 7.5 parts, diamino compound [3
8] 15 parts were placed in a ball mill pot together with 100 parts of a mixed solvent obtained by mixing methyl ethyl ketone and xylene in the same amount, and dispersed for 48 hours to prepare a photosensitive coating solution. This coating solution was applied on an aluminum substrate and dried. About 15μm thick
To form a photosensitive member. The photoreceptor thus obtained was subjected to the same method as in Example 1, except that corona charging was performed at +6 Kv, and V ₀ , E _1/2 , and DDR ₁ were measured.

Examples 19 to 21 In the same manner as in Example 18, but having the same constitution, except that the diamino compound [38] used in Example 18 was replaced with diamino compounds [42], [44] and [48] Were prepared respectively. Example 1 of the photoreceptor thus obtained was used.
V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 8.

Comparative Examples 1 to 4 In the same manner as in Example 18, but having the same constitution, except that the diamino compound used in Example 18 was replaced by the following compound
Example 18 except that [E], [F], [G], and [H] were used.
A photoreceptor was produced in exactly the same manner as described above.

Embedded image With respect to the photoreceptor thus obtained, V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 18.

Comparative Examples 5 to 7 In the same manner as in Example 18, but having the same constitution, except that the diamino compound [38] used in Example 18 was replaced by the following compounds [I], [J] and [K] A photoconductor was prepared in the same manner as in Example 18, except that each was used.

Embedded image In Comparative Examples 1 to 7, compounds [G], [H], and [I]
It was observed that the photosensitive coating solution using [H] and [H] partially precipitated crystals during the coating of the photosensitive layer. With respect to the photoreceptor thus obtained, V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 18. Table 1 summarizes the measurement results of V ₀ , E _1/2 , and DDR ₁ of the photoreceptors obtained in Examples 1 to 21 and Comparative Examples 1 to 7.

[0058]

[Table 1]

As can be seen from Table 1, the photoreceptor of the present invention has a sufficient charge retention ability, whether it is a laminated type or a single layer type, and has a dark decay rate small enough to be used as a photoreceptor.
Excellent in sensitivity. Further, a repetitive actual shooting test at the time of positive charging was performed on a photoconductor of Example 18 using a commercially available electrophotographic copying machine (manufactured by Minolta Camera Co., Ltd .; EP-350Z).
In the final image, a clear image was obtained with excellent gradation and no change in sensitivity, and it was found that the photoreceptor of the present invention had stable repetition characteristics.

[0060]

The present invention has provided a photoreceptor containing a diamino compound as a charge transport material in a photosensitive layer. A photoreceptor to which the diamino compound of the present invention was applied as a charge transporting material for a photosensitive layer was excellent in photoreceptor characteristics such as sensitivity, charge transporting property, initial surface potential, and dark decay rate, and had little light fatigue upon repeated use.

[Brief description of the drawings]

FIG. 1 is a schematic view of a dispersion type photoconductor in which a photoconductive layer is laminated on a conductive support.

FIG. 2 is a schematic diagram of a function-separated type photoconductor in which a charge generation layer and a charge transport layer are laminated on a conductive support.

FIG. 3 is a schematic view of a function-separated type photoconductor in which a charge transport layer and a charge generation layer are laminated on a conductive support.

FIG. 4 is a schematic diagram of a photosensitive member in which a photosensitive layer and a surface protective layer are formed on a conductive support.

FIG. 5 is a schematic diagram of a photoconductor in which an intermediate layer and a photosensitive layer are formed on a conductive support.

FIG. 6 shows a schematic sectional view of an electroluminescent element.

[Explanation of symbols]

1: conductive support, 2: charge transport material, 3: charge generation material, 4: photosensitive layer, 5: charge transport layer, 6: charge generation layer,
7: surface protective layer, 8: intermediate layer, 11: anode, 12: charge transport layer, 13: organic light emitting layer, 14: cathode

──────────────────────────────────────────────────続 き Continued on the front page (58) Investigated field (Int.Cl. ⁷ , DB name) C07C 217/92 C07C 211/54 C07C 323/37 C07D 333/36 G03G 5/06 312 CA (STN) REGISTRY ( STN)

Claims (3)

(57) [Claims] 1. The following general formula [I]: [In the formula, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ each independently represent an alkyl group which may have a substituent, an aralkyl group,
Represents an aryl group, a biphenyl group or a heterocyclic group;
₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group or an alkoxy group, or a halogen atom; X represents —O—, —S— or (In the formula, R ₄ and R ₅ represent a hydrogen atom, an alkyl group or an aryl group, but are not hydrogen atoms at the same time.) ] The diamino compound represented by these. 2. On a conductive support, the following general formula [I]: [In the formula, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ each independently represent an alkyl group which may have a substituent, an aralkyl group,
Represents an aryl group, a biphenyl group or a heterocyclic group;
₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group or an alkoxy group, or a halogen atom; X represents —O—, —S— or (In the formula, R ₄ and R ₅ represent a hydrogen atom, an alkyl group or an aryl group, but are not hydrogen atoms at the same time.) ] The photosensitive member which has the photosensitive layer containing the diamino compound represented by these. 3. The following general formula [I]: [In the formula, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ each independently represent an alkyl group which may have a substituent, an aralkyl group,
Represents an aryl group, a biphenyl group or a heterocyclic group;
₁ , R ₂ and R ₃ each independently represent a hydrogen atom, an alkyl group or an alkoxy group, or a halogen atom; X represents —O—, —S— or (In the formula, R ₄ and R ₅ represent a hydrogen atom, an alkyl group or an aryl group, but are not hydrogen atoms at the same time.) ] The electroluminescent element containing the diamino compound represented by these as a charge transport material.