JPS6169070A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To improve sensitivity, to stabilize the characteristics during repetitive use and to eliminate toxicity by providing a photosensitive layer contg. the triphenyl amine deriv. expressed by the specific formula on a substrate. CONSTITUTION:The photosensitive layer 4 consisting of the laminate of a carrier generating layer consisting essentially of a carrier generating material and a carrier transfer layer 3 contg. the triphenyl amine deriv. expressed by the formula (R1, R2, R3, R4 denote a hydrogen atom, halogen atom, alkyl group, etc., R5 denotes a hydrogen atom, halogen atom, alkyl group, arom. carbocyclic ring group, etc. W denotes the substd. or unsubstd. chain carbon atom group forming the condensed ring without conjugation with the benzene ring bonding with R1, R2) is provided on the conductive substrate 1 to form an ele ctrophotographic sensitive body.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive compound as a main component.

Conventionally, electrophotographic photoreceptors (hereinafter sometimes simply referred to as photoreceptors) include selenium, zinc oxide, cadmium sulfide,
BACKGROUND ART Inorganic photoreceptors having a photosensitive layer mainly composed of an inorganic photoconductive compound such as silicon have been widely used. However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture. It crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. Cadmium sulfide also has problems with moisture resistance and durability, and zinc oxide has problems with durability, etc.

In order to overcome the drawbacks of these inorganic photoreceptors, there are 8!
The development and research of photoreceptors has been actively conducted in recent years.6 For example, Japanese Patent Publication No. 10496/1983 discloses a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-trinitro-9-fluorene. There is a description of an organic photoreceptor having the following. However, this photoreceptor is not necessarily satisfactory in terms of sensitivity and durability. ! Attempts have been made to develop photoreceptors. Many studies have been conducted on such so-called function-separated type photoreceptors because each material can be selected from a wide range and a photoreceptor having arbitrary performance can be produced relatively easily.

As a result, various azo compounds have been developed and put into practical use as carrier-generating substances. On the other hand, regarding carrier transport substances, for example, JP-A-51-94829, JP-A-5
A wide variety of substances have been proposed, as disclosed in Japanese Patent Application Laid-open No. 2-72231, Japanese Patent Application Laid-Open No. 53-27033, vP Publication No. 55-52063, Japanese Patent Application Laid-Open No. 58-65440, and the like.

[Problem that the invention seeks to solve]

Although some electrophotographic photoreceptors made using carrier transport materials such as those described above exhibit relatively excellent electrophotographic performance, their durability against light or electrical loads is weak, and their durability during repeated use is poor. Because it causes unstable performance and deterioration, it does not fully satisfy the practical needs of cheap water.
It has been desired to develop a carrier transport material that has even better carrier transport function and exhibits stable performance over long periods of use.

Furthermore, in recent years Ar laser and He-N have been used as light sources for photoreceptors.
Gas lasers such as e-lasers and semiconductor lasers are beginning to be used. A characteristic of these lasers is that they can be turned on and off in chronological order, making them particularly promising as a light source for printers such as the Intelinonin Tocobi 7, which has two processing functions, and printers for computer output. In particular, semiconductor lasers are attracting attention because their nature does not require electrical signal/optical signal conversion elements such as acoustic engineering elements, and they can be made smaller and lighter. The spectral sensitivity of conventional photoreceptors is too short, as the oscillation power is lower than that of gas lasers, and the oscillation @ is also at long wavelengths (approximately 780 nm or more). It is difficult to apply this to devices that use light as a light source, and new improvements have been required for carrier transport materials.

The present invention has been carried out in order to solve these problems and provide an electrophotographic photoreceptor with extremely high durability.

[Means for solving problems]

The above problem was solved by an electrophotographic derivative characterized in that a conductive support contains a triphenylamine derivative represented by the following general formula (I).

General formula [I]' In the formula, R, , R, , R, and R4 are hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, hydroxyl groups, dialkylamino groups, noarylami/groups, dialkylamino groups, sia7 groups, or Represents a nitro group.

When R1 to R1 are an alkyl group or an alkoxy group, the number of carbon atoms is preferably 1 to 18, particularly preferably 1 to 8.

Rs represents a hydrogen atom, a halogen atom, an alkyl group, a sia/group, an aromatic carbocyclic group, or an aromatic heterocyclic group,
When it is an alkyl group, it preferably has 1 to 4 carbon atoms. Further, examples of aromatic carbocyclic groups include phenyl group and naphthyl group, and preferred aromatic heterocyclic groups include chenyl group, furyl group, and bilinol group.

W represents a substituted or unsubstituted chain carbon atom forming a non-conjugated ring with the benzene ring to which R, R2 is bonded, or more preferably a substituted or unsubstituted chain heteroatom group.

Particularly preferable combination rings formed by the above-mentioned W atomic groups are as follows. In the present invention, the triphenylamine derivative represented by the above-mentioned general formula (r) is used as the photoconductive ring of the electrophotographic photoreceptor. By using only the excellent carrier transport ability of the triphenylamine derivative of the present invention as a functional substance, it is possible to create a so-called functionally separated electrophotographic photoreceptor in which carrier generation and transport are performed using separate substances. By using it as a carrier transport material, it has excellent coating properties, and has improved charge retention, sensitivity,
It is possible to produce an electrophotographic photoreceptor that has excellent electrophotographic properties such as residual potential, exhibits little fatigue deterioration even after repeated use, and exhibits stable properties against heat and light. Furthermore, the triphenylamine derivative used in the present invention can be used alone or in combination of two or more types from among the tri-72nylamine derivatives represented by the general formula (1), and can also be used in combination with other photoconductive substances. May be used in combination.

Specific examples of the tri722ylamine derivatives represented by Maero general formula (1) that are effective in the present invention include those having the following structural formula; is not limited.

Exemplary Compounds Among the compounds represented by general formula (1), compounds represented by general formula CIa) C1a) In the table below, the bonding positions of R6 and R2 are indicated by the numbers shown in general formula (Ia), and the bonding positions of R3 and R1 are The positions are indicated as o, II+p as seen from the bonding position with N of the benzene ring.

Among the compounds represented by the general formula [■], the compound represented by the general formula CIb).

[Ib] A compound represented by the general formula CIc) among the compounds represented by CD. - [IC1 A compound represented by the general formula 〇d:] among the compounds represented by the general formula CI).

[Idl', ;"jj+notoshi2/ Next, a specific example of synthesis of the siliphenyl7mine derivative of the present invention will be described.

Synthesis Example (Synthesis of Exemplified Compound B-13) Dehydrated ether Z OOsQ in 500mQ full pen 〇-Putyltium hexane i1? ! Add 14.5 g (approximately 0.0105 mole). Under nitrogen atmosphere,
Add 5.56 g (0.01 mol) of triphenylamine-4-notyltriphenylphosphonium chloride;
After stirring for 5 hours, 1.74° (0.01 mol) of 5.7-dimethyl-1-tetralone in dehydrated ether 60. Add Q solution dropwise.

After reacting at room temperature for 48 hours, the precipitate is removed by lt:A, the IF solution is concentrated, and the target product is fractionated using silica gel column chromatography.

Yield 1 2.1g<52%) The compound of the present invention as described above has almost no photosensitivity to visible light by itself, but by applying a certain sensitization method, it can be made photoconductive to visible light. can be applied alone to form a photoreceptor. The first method is to add an organic dye and perform spectral sensitization (dye sensitization).

The second method is a method of sensitizing by forming a charge transfer complex.The following dyes can be used for 1-minute photosensitization.

(1) Methyl violet, crystal violet,
Triphenylmethane dyes such as malachite green (Z); Xanthine dyes such as erythrosine and rose bengal (3); Thianone dyes such as methyl blue and methylene green; (4); ) Cyanine dyes such as thiacyanine and oxacyanine (6) Styryl dyes such as p-tumethylamino/styrylquinoline (7) Bylylium salt dyes such as pyrylium salt, thiapyrylium salt, and benzopyrylium salt (8) 3', 3 '-Cycarpazolylmethane dyes and electron-accepting substances that can be formed with the compound of the present invention and charge transfer complexes include 2,4.7-)linitrofluorenone, 2
．． Lewis acids such as 4.5.7-thitrani), chloranil, tetracyf/quinomethane, etc. are used.

However, the compound of the present invention utilizes only its carrier transport ability and is combined with other organic dyes, pigments, or carrier-generating substances having carrier-generating ability, such as non-stirring conductors, to create a functionally separated photoreceptor. In some cases, membranes can also produce favorable effects.

The dyes shown in (1) to (8) above are useful as carrier-generating substances, and the following may be mentioned.

(1) Azo dyes such as mo/7zo dyes, nos 7zo dyes, and trisfuji dyes (2) Perylene dyes such as perylene R anhydride and perylenic acid imide (3) Innovo dyes such as innovo, thioinnovo, etc. 4) Polycyclic carboxyl//heads such as anthraquinone, bilenequinone, and 7-lapanthrones (5) Quinacridone dyes (6) Bisbencyimiguzole dyes (7) Ing-containing Ron dyes (8) Square lyrifume dyes (9) 7 talocyanine pigments such as gold 1c7 talocyanine, fi 7 thalocyanine, etc. (10) selenium, 7 thalocyanine combinations (11) filfi such as Cds, Cds e, amorphous silicon, etc. Photoconductor (12) Eutectic complex formed from biryllium salt dye, thiapyrylium salt dye and polycarbonate Among these various carrier-generating substances, consider the characteristics as a photoreceptor for semiconductor laser printers! Preferred carrier generating substances include azo compounds shown in the following general formulas (Iff) to (XM). However, in the general formula (I[[) to [X■]], general formula CI[], Z represents
izRsz+Ris+ R$41 Rss and R,,
is a hydrogen atom, a halogen atom, a furkyl group, an alkoxy group, a hydroxyl group, a nitro group, a cyano group, a noalkylamine/group,
Represents a 7-enzyme 7 group, an amide group, a 7-syl group, a carboxyl group, or an alkoxycarbonyl group.

General formula [I1[) %Formula% [In the formula, Q and Q are hydrogen atoms, halogen atoms,
[In the formula, Q3. Q and Q represent a hydrogen atom, a halogen atom, a furkyl group, or an alkoxyl group,] General formula (V) [In the formula, Q and Q are a hydrogen atom, )) a rodene atom, an alkyl group, or General formula (W) representing an alkoxyl group General formula [■] ^-N=N N=
General formula to N- [■] ＾-N=N N=N-＾-General formula ff) General formula (X) [In the formula, Q, upstream Q, is a hydrogen atom, a halogen atom,
General formula (XI) represents an alkyl group, a hydroxyl group, or an alfxyl group. n) [In the formula, Q 11 and Q +3 represent a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, or an alkoxyl group f] General formula (XI[[) [In the formula, Q +4 and 5 represent hydrogen atoms] , represents a halogen atom, a furkyl group, a hydroxyl group or an alkoxyl group, and Xl and X2 are /%l1ffdene atom (F, Cfi
, Br! or I),] General formula (XIV) [wherein, Q l &Ql represent a hydrogen atom, a halogen atom, a furkyl group, a hydroxyl group, or an alfxyl group, and Q II represents a hydrogen atom, represents a Schiff/group, a furkyl group, or a phenyl group, and Q Is to Q 13 are a hydrogen atom, a halogen atom, a Schiff) group, a furkyl group, an alkoxyl group, a hydroxyl group, an ami 7 group, a dialkyl ami 7 group, a nophenylami 7 group, or a 7 Represents a sil group] General formula (XV) [In the formula, Q 21 and V Q 2 s represent a hydrogen atom, a halogen atom, an alkyl group, a water R group, or an alkoxyl group, Ql, upper C' Q 2 t is a hydrogen atom, a furkyl group,
represents an alkoxyl group, a vinyl group which may have a direct substituent, an acyl group, an alkoxycarbonyl group, a halogen atom or a cyano group] General formula ()l) [wherein Q2. and Q 21 represents a hydrogen atom, I) a rodene atom, a furkyl group* or an alfxyl group, and Q
za and Q sl are hydrogen atoms, /ano groups, I) Rob Specific examples of the above carrier-generating substances are as follows.

One having the structure of general formula CIII].

Those having the structure of the general formula [■].

, , , , , J--”Q general formula [
V] structure.

One having the structure of the general formula CVII.

Those having the structure of the general formula CtTl).

One with four general formulas [X-cho].

N=N-A Those having the structure of general formula (IX).

Those having the structure of general formula (X).

General formula (having the g-shape of XTI.

Those having the structure of the general formula [■].

Among those having the structure of general formula [Xm], the following general formula rX
IIT=).

5.゛--CXIfJa] Among those having the structure of the general formula (X]'V), those having the structure of the following general formula CXrV.

General formula CXJV&) General formula CXV ``1'' Among those having an imitation, those having the structure of the following general formula [Xva].

General formula (XVa) - having the structure of the mosquito formula [XVI].

In addition, a photoreceptor for visible light (for example, as a light source, a halogen lamp, a xenon lamp, a tungsten lamp, an LED
, He Ney-Zer, Mah Ha+) Dragon's visible laser, etc.), the following general formulas [X■] to (XXX) are particularly preferred carrier generating substances. Examples include azo compounds. However, in the following general formula [Xn)-(XXX), A'
represents the general formula [H'].

General formula [■'] [In the formula, Z' represents R,, -R□ and R,, -R,, hydrogen atom, halogen atom, alkyl group, alkoxy group, hydroxyl group, nitro group, sia / group, difurkyl7mino group, )7enyl7mi/ group, amide group, acyl group, carboxyl group, or alkoxycarbonyl group.

General formula [X■] QHQii [In the formula, Q 32 and Q here are water'Xyi,
Represents a halogen atom, an alkyl group, a hydroxyl group or an alkoxyl group] General formula [X Formula (XI) [wherein Ql and Q3? represents a hydrogen atom, /S Roden Fushi, an alkyl group or an alkoxy group,] General formula (XX) General formula [χ℃] General formula (Xn) NU L General formula [XXll1] (wherein, Q, represents a halogen atom, an alkyl group, an alkoxyl group, a nofurkylami/group, a hydroxyl group, or a cyano group, p represents an integer of 0-5] General formula (XX!V) [wherein, Q5. and Q4゜is a hydrogen atom, a halogen atom, a furkyl group, a nnnamyl group, a 7-syl group, an ester group, or a phenyl group which may have a substituent. General formula [XXV] Ql [wherein 5Q41 and Q4m are hydrogen represents an atom, a halogen atom, an alkyl group, an alkoxy group or a hydroxyl group] General formula (XXV [) [wherein Q 42 and Q 44 are hydrogen atoms] 10
General formula (XX■) General formula (XX■) as [wherein Q45 and Q□ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or represents a hydroxyl group,
] General formula (XXff) Q4T 04g [In the formula, Q4. and Q 4m represents a hydrogen atom, a halogen atom, a furkyl group, an alkoxy group, or a hydroxyl group.] General formula (XXX) [In the formula, Ql, and Qso represent a hydrogen atom, a halogen atom, a furkyl group, or an alkoxy group. Or add hydroxyl group to h+
−] Those having the structure of the general formula [■].

Q review - Those having the structure of the ff formula [-].

Among those having the 1 character of the general formula [), those having the umezo of 0IIW-a) [Summer-1] Among those having the structure of the general formula (ff), those having the structure [-b).

Among those with the structure of the general formula [bean], those with the structure of [summer-〇].

・Number Those having the structure of general formula (XX).

Those having the structure of general formula [X1].

Those having the structure of general formula (XXI).

Those having the structure of general formula [m].

- Mathematical C mouth] 2 knees; what to do.

Qs* Qaa ·of -The one that nurtures the nine structures of the shell type [face] AI ? Those having the structure of formula Cm).

Those having the structure of general formula (XXII+).

Below) Moshio Those with the general formula [expletive] Jinzo.

Q.

General formula CX'XIO's regret! Those with f.

Q- Having the structure of the general formula (XXX) Qm The cyclized nophenylamine derivative used in the present invention does not have the ability to form a coating by itself, so a photosensitive layer is formed by combining various binders. Ru.

Any binder can be used as the binder, but it is hydrophobic and has a high dielectric constant. It is preferable to use a gas-insulating film-forming polymer. Examples of such a polymer include, but are not limited to, the following.

(1) Polycarbonate (2) Polyester (3) Ivy acrylic resin.

(4) Acrylic resin (5) Polyvinyl chloride (6) Polyvinyl chloride (7) Polystyrene (8) Polyvinyl acetate (9) For styrenic copolymerization (e.g. styrene-butanonin copolymer, styrene methyl methacrylate) Copolymer) (10) Acryloni)lyl copolymer resin (e.g. vinylidene chloride-acrylonitrile copolymer, etc.) (11) Vinyl chloride-vinyl acetate copolymer (12)
Vinyl chloride-vinyl acetate-maleic anhydride copolymer (13) Silicone resin (14) Silicone-alkyd tII! ! (15)
71nolff1jlllF (e.g. 7E7-formaldehyde fat, ■-cresol-formaldehyde at fat, etc.) (16) Styrene-alkyd resin (17) Poly-N-vinylcarbazole (18) Polyvinyl butyral (19) Polyvinyl 7-olmar These binders can be used alone or as a mixture of two or more.

As shown in FIGS. 12B to 2V, the photoreceptor of the present invention has a carrier-generating layer 2 containing a carrier-generating substance as a main component and a carrier-transporting layer 2 containing the triphenylamine derivative of the present invention on a conductive support 1. A photosensitive material N4 is provided which is a laminate with carrier transport N3 containing as a main component. As shown in tIS3 and FIG. 4, this photosensitive layer 4 may be provided via an intermediate M5 provided on the conductive support 1. When the photosensitive layer 4 has a two-layer structure in this way, it is most effective. An electrophotographic photoreceptor having excellent electrophotographic properties can be obtained. Further, in the present invention, as shown in FIGS. 5 and 6, a photosensitive layer 4 formed by dispersing a carrier generating substance 7 in the form of fine particles in a layer 6 mainly composed of the carrier transporting substance is used as a conductive support. The fifth (21st and sixth
Preferable results can also be obtained by providing a single photosensitive layer 4 as shown in the figure.

If the photosensitive layer 4 has a two-layer structure, it is determined whether the carrier generation layer 2 or the carrier transport layer 3 is the upper layer.
It is determined by whether the 1L polarity is selected as positive or negative. In other words, when forming a negatively charged photosensitive layer, it is advantageous to use the carrier transport N3 as an upper layer, because the tri7dinylamine derivative in the carrier J7 transport layer 3 has a high transport ability for holes. This is because it is a substance that has

Also, the chips and chips 7 forming the two-layer #I photosensitive layer 4 are generated N.
2 is a conductive support] or carrier transport N3
[It can be formed by the following method after providing an intermediate layer such as an adhesive layer or a barrier layer if necessary.

(1) Shin'g! Vapor deposition method (2) A method of applying a solution containing a carrier-generating substance dissolved in a suitable solvent.

(3) A method in which a carrier-generating substance is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and if necessary, mixed and dispersed with a binder to form a dispersion liquid.

The carrier generation layer 2 formed in this way! ! Preferably, i is 0.01 to 5 microns, more preferably 0.05 to 3 microns.

Although the thickness of the carrier transport layer M3 can be changed as necessary, it is usually preferably 5 to 30 mm thick.The composition ratio of the second carrier transport layer 3 is based on the triphenylamine derivative of the present invention. Carrier transport substance 1
It is preferable to use the binder in an amount of 0.8 to 10 parts by weight per weight tg, but when forming the photosensitive layer 4 in which a fine powder carrier-generating substance is dispersed, carrier-generating substance type 1! It is preferable that the binder be contained in an amount of 5 parts to 1 part or less per part of the binder.

Further, when the carrier generation layer 2 is configured as a dispersion type layer using a binder, it is preferable to use the N binder in an amount of 5 parts or less per 1 part by weight of the carrier generating substance.

The conductive support 1 used in the construction of the electrophotographic photoreceptor of the present invention mainly includes the following, but is not limited to these.1.1) Aluminum plate, stainless steel plate, etc. Meeting board.

2) A thin metal layer such as full mini 7m, balanoum, or porcelain is provided on a support such as paper or plastic film by lamination or vapor deposition.

3) A layer of a conductive compound such as a conductive polymer, ink oxide, tin oxide, etc. is provided on a support such as a soft or plastic film by coating or vapor deposition.

The intermediate layer 5, such as an adhesive layer or a barrier layer, may be made of an organic polymer material such as gelatin, casein, starch, polyvinyl alcohol, vinyl acetate, ethyl cellulose, or carboquine methyl cellulose, in addition to the molecular polymer used as the binder. Alternatively, aluminum oxide or the like is used.

The photoreceptor of the present invention has the above-mentioned structure, and as is clear from the examples described later, it has excellent charging characteristics, sensitivity characteristics, and W image forming characteristics.

The present invention will be specifically explained below using Examples, but the embodiments of the present invention are not limited thereto.

Example 1 Selenium was evaporated onto a conductive support consisting of a laminate of aluminum foil on a polyester film to a thickness of 0.
A carrier generation layer of 5 microns was formed. in addition,
1 part of Exemplified Compound B-1,6 heavy J and Polycarbofuyu-F [Panlite L-IZ50J (IF Jinkaseisha 1 Li 101
! were dissolved in 90 parts of 1,2-dichloromethane, and the film thickness after drying was 11 microns.
The electrophotographic photoreceptor of the present invention was prepared by coating the powder to form a transport layer.

Electrostatic copying paper test for this electrophotographic photoreceptor! Device"
The electrophotographic characteristics were measured using a dynamic method using a model 5P-428 (Kawaguchi Electric Seisakusho 91). That is,
The surface potential of the photosensitive layer of the photoreceptor was charged for 5 seconds at a charging voltage of -6 KV (8), and then the light from a tungsten lamp was applied to the surface of the photoreceptor so that the illuminance was 35111X to J! uJtL, the amount required to attenuate the surface potential V^ by half t(low-exposure 1)E M (l
The surface potentials (residual potentials) VFI after irradiating ux-sea) fiz with a fallen light amount of 301 ux-see were determined. The same measurement was repeated 100 times.

The results are shown in Table 1.

1st! As is clear from the table in IC 2, the electrophotographic photoreceptor of the present invention has sufficient R4 load holding power, has a low commercial sensitivity, low residual potential, and maintains good durability even after repeated use. It has excellent properties as a photographic photoreceptor.

Comparative Example 1 A comparative photoreceptor was prepared in the same manner as in Example 1, except that Compound T-1 below was used instead of Exemplary Compound B-1 as a carrier transporting substance. -13c When this photoreceptor was measured in the same manner as in Example 1, the results of the second wheat were obtained.

As is clear from the above results, the comparative photoreceptor
' was significantly inferior to the photoreceptor of the present invention of Example 1 in terms of stability during repeated use.

Examples 2 to 4 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1, except that exemplified compounds l1ljB-20, B-21, and B-2 were used instead of exemplified compound B-1 as a carrier-generating substance. It was created. The initial characteristics of these photoreceptors were measured in the same manner as in Example 2, and the results obtained were the same as in Example 3.

Table 3 Example 5 A polyester film with a thickness of 0 made of vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-LEC MF-10J (manufactured by Block Chemical Co., Ltd.) was placed on a conductive support made of aluminum vapor-deposited on a polyester film. , 05 micron intermediate layer is provided, and on top of that is Nobromo 7th 7thlon [Monolite Red 2].
YJ (C, 1, No. 593001 manufactured by C1 company) 1 layer! Polycarbonate was added to the fractional liquid obtained by adding 1,2-ν parts to 30 weight US of tetraloethane and dispersing it in a ball mill.
Panlight L-1250J (Ondai Kaseisha U) 1.
A carrier-generating layer was formed by dissolving 5 parts by weight of the carrier-generating layer and applying a sufficiently mixed coating solution to a film thickness of 2 microns after drying.

On top of that, Exemplified Compound B-5.6 times! A carrier transport layer was formed by applying a solution of Miyako and 10 parts by weight of the polyester "Pylon 200J (manufactured by Toyobo Co., Ltd.) dissolved in 90 parts of 1,2-nochloroethane so that the film thickness after drying was 11 microns. An electrophotographic photoreceptor of the present invention was prepared. This photoreceptor was measured in the same manner as in Example 1, and results of tj & 4 were obtained.

Table 4 Comparative Example 2 Measurements were made in the same manner as in Example 1 for Example 5 and this comparative photoreceptor, except that Compound T-2 below was used instead of Exemplified Compound B-5 as a carrier transport substance. The results shown in Table 5 were obtained.

As is clear from the results in Table 5 and above, the comparative photoreceptor was significantly inferior in sensitivity and repeated stability compared to the compound of the present invention.

6. Polyester "Pylon 200J" was placed on a conductive support made of aluminum foil laminated on a polyester film.
(manufactured by Toyo Uki Co., Ltd.) with a thickness of 0.1 micron.

On top of that, a liquid containing 1 part of 7zo pigment represented by the following structural formula as a carrier generating substance dispersed in 60 parts by weight of 1,2-nochloroethane was added after drying. A carrier generation layer was formed by coating so that the thickness of A was 0.3 microns. Furthermore, exemplified compound B-5.61! 'j1 part and polycarbonate "Panlite L-1250J (manufactured by Masenjin Kasei Co., Ltd.)"
An electrophotographic photoreceptor of the present invention was prepared by forming a carrier transport layer by coating a solution obtained by dissolving 1Offii part and 1,2-Fukuro 01 Fufu in 9011 parts of 1,2-Fukuro 01 Fufu to a thickness of 15 microns after drying. . The initial characteristics of this photoreceptor were measured in the same manner as in Example 1, and V A = -
910v, E% = 4.21ux-see and VF
I=OV.

In addition, the second photoconductor is an electrophotographic photoconductor 7U-Bix2000.
When a photocopy test was carried out using the RJ (manufactured by Konishiroku Photo Industry Co., Ltd.), a copy image was obtained that was faithful to the original, had high contrast, excellent gradation, and was in # period.

Even when this was repeated 1000 times, a good copy image was obtained, which was the same as in the 4JJ period.

Example 7 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 6, except that the following compound was used as a carrier generating substance.

The initial characteristics of the second photoreceptor are VA = -880v, E) 4 =
4.31ux-see, V steam = Ov. This was electrophotographically copied mrU-B ix 2000 RJ (
(manufactured by Konishiroku Photo Industry Co., Ltd.) and conducted a live-action test.10
Good copy 'fR, no different from the first M even after 00 repetitions
Got the statue.

Example 8 The triphenyl7mine derivative of the present patent has excellent performance as a carrier transport material for photoreceptors in semiconductor laser printers. Actually, a photoreceptor for a semiconductor laser was produced as described below, and good results were obtained.

A vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC MF-10J (manufactured by Tanezu Kagaku Co., Ltd.) with a thickness of 0.05 μm was placed on an aluminum drum with an outer diameter of 10 cm as a conductive support. A layer is provided on which the compound G-1SL2g is added (1+2-7')aaxfn1
A carrier generation layer was formed by mixing a dispersion liquid of 10t*Q and dispersing it in a ball mill for 24 hours and applying it to a film thickness of 0.1 μ- after drying. On this carrier generation layer, a solution of 6 g of Exemplary Compound B-24+ and methacrylic resin "Acrivet" (Mitsubishi Rayon Co., Ltd. B 10) dissolved in 1,2-nochloroethane 7G, Q was added to the dried film. Apply it to a thickness of 18μ- and apply it to +77
A transport layer is formed to produce the electrophotographic photoreceptor of the present invention.

The sensitivity of this photoreceptor to a 79 On- semiconductor laser beam is 420 vo) l-am''・11 W-'・
A photographic test was carried out using an experimental machine equipped with a semiconductor laser (790 na) whose laser light intensity on the surface of the photoreceptor of the present invention was 0.85 IIW and had an optical attenuation rate of 5ee-' (light attenuation rate).

After the surface of the photoreceptor was charged to -6 KV, it was exposed to laser light and reversely developed at a Bayer voltage of -ZSOv, and a good image without capri was obtained.

Comparative Example 3 A comparative photoreceptor was obtained in the same manner as in Example 8 except that the following exemplified compound T-3 was used instead of exemplified compound B-24. Sensitivity is 110 voH-cm"・μW-' ・5ee
-' (light attenuation rate). Using the second comparative y@sensitive member, a photo-taking test using a semiconductor laser was conducted in the same manner as in Example 8, but a good Ii image was not obtained due to a large amount of capri.

Examples 9 to 32 Photoreceptors were prepared by combining the carrier-generating substances shown in Table 6 and the carrier-transporting substances of the present invention.

What are the conditions for making the photoreceptor using both of the above materials? Everything was the same as in Example 8 except for 1w1. The sensitivity of each sample to the 79On- laser beam was good as shown in the table.
As is clear from the results of the Examples and Comparative Examples in the table above, the photoreceptor of the present invention has significantly better characteristics such as stability, sensitivity, durability, and combination with a wide range of carrier transport substances than the comparative photoreceptor. It is something that was given.

[Examples 33 to 56] Photoreceptors were prepared by replacing the carrier-generating substance and carrier-transporting substance B-5 of Example 6 with the carrier-generating substance and carrier-transporting substance shown in Table 7, respectively. Measure the photosensitivity E to visible light according to the seventh method.
The results shown in the table were obtained.

As shown in the table, the number of uses of the carrier transport material according to the present invention is
Table 7 [Effects of the Invention] According to the present invention, it is possible to obtain an excellent photoreceptor that has high sensitivity, extremely stable characteristics during repeated use, and has no toxicity problems.

[Brief explanation of drawings]

10 to 6 each represent a cross-sectional view of an example of the mechanical structure of the electrophotographic photoreceptor of the present invention. 1...Electroconductive support 2--...Carrier generation layer 3...Carrier+77 Transport layer 4...Photosensitive layer 5...Intermediate layer 6... Calendar 7 containing well J7 transport substance
--- Carrier-generating substance agent Patent attorney No 1) View of righteousness Figure 2 Figure 4

Claims (3)

[Claims] (1) An electrophotographic photoreceptor comprising a photosensitive layer containing a triphenylamine derivative represented by the following general formula [I] on a conductive support. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_1, R_2, R_3, R_4 are hydrogen atoms, halogen atoms, alkyl groups, alkoxy groups, hydroxyl groups, dialkylamino groups, diarylamino groups, dialkyl represents an amino group, a cyano group, or a nitro group; R_5 represents a hydrogen atom, a halogen atom, an alkyl group, a cyano group, an aromatic carbocyclic group or an aromatic heterocyclic group; W represents R_1, R_
It represents a substituted or unsubstituted chain carbon atomic group or a substituted or unsubstituted chain hetero atomic group that forms a non-conjugated condensed ring with the benzene ring to which 2 is bonded. ] (2) The photosensitive layer contains a carrier-generating substance and a carrier-transporting substance, and the carrier-transporting substance has the general formula [
The electrophotographic photoreceptor according to claim 1, which uses a triphenylamine derivative represented by I]. (3) The electrophotography according to claim 1 or 2, wherein the photosensitive layer is constituted by a laminate of a carrier-generating layer containing a carrier-generating substance and a carrier-transporting layer containing a carrier-transporting substance. Photoreceptor.