JPS60196768A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain high sensitivity, low residual potential and excellent durability by incorporating a specific triaryl amine deriv. as a carrier transfer material into the titled body. CONSTITUTION:The triaryl amine deriv. expressed by the formula (An1, An2 are substd. and unsubstd. phenyl, naphthyl, and may have groups such as alkyl, alkoxy, halogen, amino, etc. as the substituent, R1-R7 are respectively H, alkyl, alkenyl, alkoxy, phenoxy, amino, etc., R3-R7 are not simultaneously H) is used as a carrier transfer material (CTM) for constituting a function sepn. type photosensitive body. The most excellent electrophotographic characteristic is obtd. when the photosensitive layer is made into two-layered constitution by providing a carrier generating layer 2 and a carrier transfer layer 3 contg. such CTM adjacent to the layer 2 via an intermediate layer 5 according to need on a conductive base 1. A good electrifying characteristic, photosensitive characteristic and image characteristic are thereby obtd. and even if the photosensitive body is repeatedly used, the various characteristics are stable and said body has excellent durability.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly to a novel electrophotographic photoreceptor having a photosensitive layer containing a carrier-generating substance and a carrier-transporting substance.

Conventionally, electrophotographic photoreceptors having photosensitive layers containing inorganic photoconductors such as selenium, zinc oxide, and cadmium sulfide as main components have been widely known. However, these properties are not always satisfactory in terms of properties such as thermal stability and durability, or they are difficult to manufacture due to toxicity.
There were also problems in handling.

First, electrophotographic photoreceptors having a photosensitive layer containing an organic photoconductive compound as a main component are relatively easy to manufacture, inexpensive, and easy to handle. It has many advantages, such as superior thermal stability, and has attracted a lot of attention in recent years. Poly-N-vinylcarbazole is the most well-known such organic photoconductive compound, and 2.4.7-)
Electrophotographic photoreceptors having a photosensitive layer mainly composed of a charge transfer complex formed from a Lewis acid such as linitro-9-fluorenone have already been put into practical use.

On the other hand, electrophotographic photoreceptors are known that have a laminated type or dispersion type functionally separated photosensitive layer in which the carrier generation function and the carrier transport function of the photoconductor are assigned to separate substances, respectively. Electrophotographic photoreceptors having a photosensitive layer consisting of a carrier generation layer consisting of a thin layer of amorphous selenium and a carrier transport layer containing poly-N-vinylcarbazole as a main component have already been put to practical use.

However, since poly-N-vinylcarbazole lacks visibility, its coating is hard and brittle and prone to cracking and peeling, so electrophotographic photoreceptors using it have poor durability. If a flexibilizing agent is added to improve this drawback, the residual potential will increase when subjected to the electrophotographic process, and as the material is used repeatedly, the residual potential will accumulate and capri will gradually appear in the copied image. It has the disadvantage of becoming.

In addition, since low-molecular organic photoconductive compounds generally do not have film-forming ability, they are used in combination with any binder, and therefore the physical properties of the film can be determined by selecting the type and composition ratio of the binder used. However, the types of organic photoconductive compounds that have high compatibility with binders are limited, and in reality they cannot be used in electrophotographic photoreceptors. The reality is that there are not many materials that can be used in the composition of the photosensitive layer.

For example, 2,5-bis(P-noethylaminophenyl),-1,3,4-oxadiazole described in U.S. Pat. Since the material has low compatibility with binders that are usually preferably used as materials for photosensitive layers, it is necessary to mix it with binders such as polyester and polycarbonate in the proportions required to obtain favorable electrophotographic properties. If formed, oxadiazole crystals will precipitate at a temperature of 50° C. or higher, which has the disadvantage of deteriorating electrophotographic properties such as charge retention and sensitivity.

On the other hand, the diarylalkane derivatives described in U.S. Pat. When used in the construction of a photosensitive layer of a photoreceptor for repetitive transfer type electrophotography in which charging and exposure are repeated, the disadvantage is that the sensitivity of the photosensitive layer gradually decreases.

The reality is that a carrier transport material having Amagawa-I favorable characteristics for producing an electrophotographic photoreceptor has not yet been found.

The main objective of the present invention is to provide a novel carrier transport material that has high compatibility with a binder and can form a homogeneous photosensitive layer.

Another object of the present invention is to provide an electrophotographic photoreceptor with high sensitivity and low residual potential.

Still another object of the present invention is to maintain stable characteristics over a long period of time with little fatigue deterioration due to repeated use when used as a photoreceptor for electrophotography of a repetitive transfer type in which charging, exposure, development, and transfer steps are repeated. An object of the present invention is to provide an electrophotographic photoreceptor having excellent durability.

In order to achieve the above object, the present inventors have conducted extensive research and found that by using a specific triarylamine derivative as a carrier transport material for a functionally separated photoreceptor,
The present invention has been completed by discovering that the first objective can be achieved.

The above object is achieved by using a triarylamine derivative represented by the following general formula as a carrier transport material constituting a functionally separated photoreceptor.

General formula [1] In the formula, N + + A n represents a substituted or unsubstituted phenyl group or a naphthyl group, respectively, and these substituents include a substituted or unsubstituted alkyl group, a substituted or unsubstituted It represents an alkenyl group, a substituted or unsubstituted alkoxy group, a halogen atom, an amine 7 group, a substituted amine 7 group, a substituted or unsubstituted phenoxy group, or a substituted or unsubstituted alkenyloxy group.

R,, R7, R3, R,, RS, R6, and R7 may be the same or different, and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted,
Unsubstituted alkoxy group, substituted or unsubstituted alkenyloxy group, substituted or unsubstituted phenoxy group, amine 7 group, substituted amine 7 group, hydroxyl group, halogen atom, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted represents an acetyl group.

However, this excludes the case where R3, R4, R5, R6, and R7 are hydrogen atoms at the same time.

That is, in the present invention, the carrier transport ability of the triarylamine derivative represented by the above general formula is utilized, and this is used as a carrier in the photosensitive layer of a so-called functionally separated photoreceptor in which carrier generation and transport are performed using separate substances. When used as a transport material, it has excellent film properties, excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and has little fatigue deterioration even after repeated use.
It is possible to create an electrophotographic photoreceptor that exhibits stable characteristics without any change in the above-mentioned characteristics. Specific examples of the triarylamine derivatives represented by the above general formula that are effective in the present invention include those having the following structural formulas. A-(3) A-(4) A-(5) A-(6) A-(8) A-(9) A-(10) A-(1,1) Δ-(12) A-( +3) Δ-(14) A-(15) A-(16) A-(17) A-(18) A-(19) A-(20) Δ-(21) A-(22) Δ-( 2:1) A-(24) A-(25) Δ-(26) A-(27) A-(28) A-(29) A,-(30) 8-(31) A-(32) A-(33) A-(34) A-(36) A-(37) A-(38) A-(40) A-(41) 8-(42) A-(43) A-(44) A-(45) A-(46) A-(47) A-(48) A-(49) A-(50) A-(5]) A-(52) 8-(53) A-(54 ) A-(55) A-(56) A-(57) A-(58) A-(59) A-(60) A-(61) A-(62) A-(63) A-(64 ) 113 A-(65) A-(66) A-(67) A-(68) A-(69) A-(70) A-(71) A-(72) A-(73) A- (75) A-(76) i-t3 A-(77) A-(78) A-(79) A-(80) A-(81) A-(82) A-(84) A-( 85) A-(86) A-(87) A-(88) A-(89) A-(90) A-(91) A-(92) A-(93) Δ-(94) A-( 95) A-(96) A-(97) A-(98) A-(99) A-(101) A-(102) A-(103) A-(104) A-(105) A-( 106) A-(107) A-(108) A-(109) A-(110) A-(111) A-(112) A-(113) A-(116) A-([7) A- (118) A-(119) A-(120) A-(124) A-(122) A-(123) A-(124) A-(125) A-(126) A-(127n A- (128) The above triarylamine derivatives can be easily synthesized by known methods.
ic Reactions vol, 25 P, 73
(John Wiley & 5ons, Inc.)
As described, an aromatic aldehyde represented by the following general formula [■] and a dialkyl phosphonate represented by the following general formula [1ll] are mixed in a solvent such as N,N-dimethylformamide in the presence of sodium alkoxide, etc. It can be easily obtained by subcondensation.

[11[I[1] [11 where A nzAn2yRltR21R3wR<tRs
+RevR7 represents the same as in general formula II), and R8 represents an alkyl group or an aryl group.

Next, a typical method for synthesizing the triallino (amine derivative) used in the present invention will be specifically explained.

Synthesis Example 1 (Synthesis of Exemplified Compound A-(41)) 4.8 g (0.02 m
ol) and 4-methyl-4'-formyltriphenylamine 6, Og (0,02 pupils of) are added to 70-N,N-dimethylformamide, dissolved, and then cooled with water.

Add 2.2g (0.04ml) of sodium methoxide to this solution.
ol) gradually while keeping the internal temperature below 10°C.

Thereafter, the mixture was stirred for 1 hour under water cooling and for 2 hours at room temperature.

After leaving it at room temperature overnight, add 50% water ice. lll1! The precipitate was collected by filtration and recrystallized twice with a mixed solvent of toluene/isopropyl alcohol = 1:2.

Yield: 5.2g (70.0%) Melting point: 130°C to 132°C Fl) -brass spectrum: ta/e = 37
Since the molecular ion of No. 5 was detected, it was confirmed that the obtained compound was the target compound. - Synthesis Example 2 (Synthesis of Exemplified Compound A-(62)) 5.2 g (0.02 m
ol) and 6.4 g of 4-methyl-4'-methoxy-4''-formyltriphenylamine (0,02111o
1) is added to 70-N,N-trimethylformamide, dissolved, and then cooled with water.

Add 2.2g (0.04ml) of sodium methoxide to this solution.
ol) gradually while keeping the internal temperature below 10°C.

Thereafter, the mixture was stirred for 1 hour under water cooling and for 2 hours at room temperature.

After further standing overnight at room temperature, 50% of water ice was added and the precipitate was collected by filtration, toluene/isopropyl alcohol = 1:2.
It was recrystallized twice with a mixed solvent of

Yield: 6.1 g (72.0%) Melting point: 109°C to 111°C Since a molecular ion beam with m/e=421 was detected in the FD n+ass spectrum, it was confirmed that the obtained compound was the target compound.

The carrier transporting material of the present invention can effectively constitute an electrophotographic photoreceptor in combination with any carrier generating material. Examples of the carrier-generating substance used in the present invention include organic dyes and pigments having carrier-generating ability. Particularly preferred organic dyes/pigments include azo dyes such as mo/azo dyes, bisazo dyes, and trisazo dyes.

For example, the azo dyes described in the following publications are effectively used as carrier-generating substances in the present invention, but the carrier-generating substances effective in the present invention are not limited to these. (
Hereinafter, A represents a coupler. )B-(1) JP-A-53
-95033 publication RR:H, C2H6 B-(2) JP-A-53-133445 publication B-(3
) JP-A-54-2129 B-(4) JP-A-54-2129 B-(4)
Publication No. 54-12742 B-(5) JP-A-54-20
736 Publication B-(6) JP-A-54-21728-B-(7) JP-A-54-22834-A B-(8
) JP-A-55-69148 B-(9) JP-A-55-73057 B-(10) JP-A-56-2
Publication No. 1128 +3-(11) JP-A-56-1434
37 Publication B - (12) JP 56-11945 B - (15) JP 53-132347 B - (16) JP 56-46237 B -
(17) JP-A-57-182747 B-(18
) JP-A-57-182748 B-(19)
JP-A-58-70232 JP-A-58-14074
No. 5 Publication B-(20) JP-A No. 58-152248 B
-(21) JP-A-58-194035 B -(
22) JP-A-58-173748 B-(23
) JP-A-57-63542 Since the triarylamine derivative of the present invention does not have film-forming ability, when it is used to form a photosensitive layer, it is preferably used together with a binder. The preferred binder used in the present invention is a hydrophobic, high dielectric constant, electrically insulating film-forming polymer. Examples of such polymers include the following.

C-(1) Polystyrene C-(2) Polyvinyl chloride C-(3) Polyvinylidene chloride C7(4) Polyvinyl acetate C-(5) Acrylic resin C-(6> Methacrylic resin C-(7) Polyester C- (S) Polycarbonate C-(9) 7-ethyl formaldehyde resin C-(10
) Styrene-butadiene copolymer C-(+1) Vinylidene chloride-acrylonitrile copolymer C-(+2) Vinyl chloride-vinyl acetate copolymer C-(1)
3) Vinyl chloride-vinyl acetate-maleic anhydride copolymer-C-(14) Silicone resin C-(15) Silicone-flukyd resin C-(16) Styrene-alkyd resin C-(17) Poly-N- Vinyl carbazole C-(18) Polyvinyl butyral C-(19) Polyvinylanthracene C-(20) Phenoxy resin c-(21) Polyacrylamide c-(22) Polyamide C-(23) Urethane resin C-(24) Epoxy resin These binders may be used alone or in combination of two or more, or at least two of the monomers constituting the polymer.
Although the binder used in the present invention is used as a copolymer containing more than one species, the binder used in the present invention is not limited to these.

The photoreceptor of the present invention is shown in FIGS. 1, 2, 3, and 4.
As shown in the figure, when a carrier generation layer 2 and a carrier transport layer 3 are provided adjacent to this layer on a conductive support 1 via an intermediate layer 5 if necessary, the photosensitive layer has a two-layer structure. As shown in FIGS. 5 and 6, a carrier transporting substance is deposited as a main component on a conductive support 1 via an intermediate JvI5 as required. A photoreceptor in which fine particles 7 of a carrier-generating substance are dispersed in a photoreceptor layer 6 containing as a material can also be effectively used in the present invention.

When the photosensitive layer 4 has a two-layer structure, which of the carrier generation layer 2 and the carrier transport layer 3 is to be the upper layer is determined by whether the charging polarity is positive or negative. That is, when used with negative charge, it is advantageous to use the carrier transport layer 3 as an upper layer, and this is because the triarylamine derivative of the present invention in the carrier transport layer is a substance having a high transport ability for holes. This is because.

In addition, carrier generation N2 constituting the photosensitive layer 4 having a two-layer structure
can be formed on the conductive support 1 or the carrier transport layer (J2 directly, or optionally provided with an intermediate layer such as an adhesive layer or a barrier layer) by the following method.

D-(1) A method of dissolving a carrier-generating substance in a suitable solvent and applying it.

D-(2) A method in which a carrier-generating substance is made into fine particles in a dispersion medium using a ball mill, a homomixer, a sand mill, a colloid mill, a roll mill, etc., and a dispersion obtained by mixing and dispersing with a binder as necessary is applied. .

Here, the solvent used for forming the carrier generation layer includes n-butylamine, diethylamine, triethylamine, monoethanolamine, jetanolamine, triethanolamine, ethylenediamine, impropaturamine, pyridine, 1,8-diazabicyclo( 5,
Organic amines such as 4,0)-7-undecene, ketones such as acetone, methyl ethyl ketone, cyclohexanone, diethyl ketone, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, dichloromethane, chloroform, 1,2 - Halogenated hydrocarbons such as dichloroethane and trichlene, ethers such as dioxane, tetrahydro-7rane, butyl ethyl ether, methanol,
In addition to alcohols such as ethanol, isopropyl alcohol, and 7'tanol, and esters such as methyl acetate, ethyl acetate, butyl acetate, and methylcellosolve acetate,
Examples include NtN-trimethylformamide and trimethylsulfoxide.

These may be used alone or in combination of two or more depending on the purpose.

When a binder is used in the carrier generation layer, any binder can be selected from the above-mentioned binders alone or as a mixture.

The thickness of the carrier generation layer 2 formed in this way is
It is preferably 0.01 to 3 microns, more preferably 0.05 to 1 micron.

The particle size of the carrier-generating substance is preferably 3 microns or less, more preferably 0.5 microns or less.

Further, the thickness of the carrier transport layer 3 can be changed as necessary, but it is usually preferably 5 to 30 microns.

The composition ratio in this carrier transport layer 3 is preferably 0.8 to 5 parts by weight of the binder to 1 part by weight of the carrier transport material whose main component is the above-mentioned triarylamine derivative.

When forming the photosensitive layer 4 in which a fine powder carrier-generating substance is dispersed, it is preferable to use the binder in an amount of 5 parts by weight or less per 1 part by weight of the carrier-generating substance. When a binder is used in the carrier generation layer 2, it is preferably used in an amount of 5 parts by weight or less, more preferably 2 parts by weight or less, per 1 part by weight of the carrier generating substance.

The solvent used to form the carrier transport layer is arbitrarily selected from those capable of dissolving the carrier transport substance and the binder depending on coating conditions and the like.

The most common solvents include ethers such as tetrahydro7rane, dioxane, and butyl ethyl ether, ketones such as acetone, methyl ethyl ketone, cyclohexanone, and diethyl ketone, benzene, toluene, xylene,
Aromatic hydrocarbons such as chlorobenzene, methylene chloride,
Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, alcohols such as methanol, ethanol, isopropyl alcohol, butanol, esters such as methyl acetate, ethyl acetate, butyl acetate, methylcellosolve acetate, etc. Mixtures may be mentioned.

Examples of the conductive support used in the construction of the electrophotographic photoreceptor of the present invention include metal plates such as aluminum, nickel, iron, and stainless steel, metal drums, and metal belts, as well as polyester films laminated with aluminum thin films, paper, aluminum, gold, nickel,
Examples include polyester films and paper made conductive by vapor-depositing palladium, indium oxide, and tin oxide.

As an intermediate layer such as an adhesive layer or a barrier layer, in addition to the high molecular weight polymer used as a binder for the photosensitive layer,
Aluminum oxide or the like is used.

The electrophotographic photoreceptor of the present invention has the above structure,
As is clear from the Examples described below, it has excellent charging characteristics, sensitivity characteristics, and image characteristics, and these characteristics are stable even after repeated use, and it has excellent durability.

EXAMPLES The present invention will be specifically explained below with reference to Examples, but the embodiments of the present invention are not limited thereto.

Example 1 A vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC MP-10J (made by Tanezu Kagaku Kogyo Co., Ltd.) was coated on a conductive support made of polyethylene terephthalate having a thickness of 100 microns and coated with aluminum. Thickness 0
．． A 1-micron intermediate layer was provided, and 2 g of a bisazo compound shown by the structural formula below and a polymethyl methacrylate resin [
Elbasite 2010J (manufactured by DuPont Hg and 1,2
-dichloroethane 100- and dispersed in a ball mill for 24 hours, and the resulting dispersion was applied onto the intermediate layer using a wire bar and dried, with a coating amount of 0.3 g/
The carrier generation layer of theory 2 was formed.

On the other hand, 11.25 g of the triarylamine derivative shown in Exemplary Compound A-(62) and 15 g of polycarbonate resin [Panlite L-12504 (manufactured by Ondai Kasei Co., Ltd.) were dissolved in 1°2-dichloroethane 100- The resulting solution was applied onto the carrier generation layer using a doctor blade and sufficiently dried to form a carrier transport layer having a thickness of 15 microns, thereby producing an electrophotographic photoreceptor of the present invention. This will be referred to as "Sample 1".

Examples 2 to 13 In forming the carrier transport layer, exemplary compounds A-(1), A-(5), Δ- were used as triarylamine derivatives.
(7), A-(13), A-(15), A-(2
2), A-(33), A-(41), A-(43)
, A-(59), A-(61), and V A-(7
7) 12 in the same manner as in Example 1 except that each of
A seed electrophotographic photoreceptor of the present invention was prepared. These are referred to as "Sample 2" to "Sample 13J", respectively.

Comparative Example 1 In the formation of the carrier transport layer, a compound having the following structural formula was used as the triarylamine derivative.
A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 1. This is referred to as 1-Comparative Sample 1.

In the formation of the carrier generation layer, a bisazo compound having the following structural formula is used as a carrier generation substance, and in the formation of the carrier transport layer, exemplary compounds A-(1), A-
(5), A-(8), A-(41), A-(43
), A-(56), and A-(56) were used in the same manner as in Example 1 to prepare six types of electrophotographic photoreceptors of the present invention.

These are referred to as "Sample 14" to "Sample 19J", respectively.

Comparative Example 2 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 14, except that a triarylamine derivative having the following structural formula was used as a carrier transport substance in forming the carrier transport layer. This is designated as "Comparative Sample 2" 6. In the formation of the carrier generation layer, a bisazo compound having the following structural formula is used as the carrier generation substance, and in the formation of the carrier transport layer, the exemplary compound A-(6) is used as the carrier transport substance. , A-(9), A-(22),
Five types of electrophotographic photoreceptors of the present invention were prepared in the same manner as in Example 1 except that each of those shown as Δ-(61) and A-(62) was used. These are each "sample 20" ~
It is called "Sample 24."

Comparative Example 3 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 20, except that a triarylamine derivative having the following structural formula was used as the carrier transport substance in forming the carrier transport layer. This will be referred to as "comparative sample 3."

Examples 25 to 29 In the formation of the carrier generation layer, a bisazo compound having the following structural formula was used as the carrier generation substance, and in the formation of the carrier transport layer, exemplary compounds A-(5), A-(41), A-(61), A
Five types of electrophotographic photoreceptors of the present invention were prepared in exactly the same manner as in Example 1 using each of those shown in A-(62) and A-(64).

These are respectively referred to as "sample 25" to "sample 29."

Comparative Example 4 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 25, except that a triarylamine derivative having the following structural formula was used as the carrier transport material in forming the carrier transport layer. Comparative Trial Examples 30 to 38 A bisazo compound having the following structural formula was used as a carrier-generating substance in the formation of the carrier-generating layer, and exemplified compounds A-(1) and A were used as the carrier-transporting substance in the formation of the carrier-transporting layer. -(3), A-(5), A-(3
5), A-(38), A-(61), A-(62)
, A-(64), and A-(65) were used in the same manner as in Example 1 to prepare nine types of electrophotographic photoreceptors of the present invention. These are each labeled as “sample 30”.
J~ "Sample 38".

Comparative Example 5 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 30, except that a triarylamine derivative having the following structural formula was used as a carrier transport substance in forming the carrier transport layer. This will be referred to as "comparative sample 5."

Examples 39 to 42 In forming a carrier generation layer, a bisazo compound having the following structural formula was used as a carrier generation substance,
Exemplary compounds A-(1), A-(5), A-(old), A- as carrier +77 transport substances in the formation of the transport layer
Example 1 except that each of those shown in (62) was used.
Four types of electrophotographic photoreceptors of the present invention were prepared in the same manner as described above. These are respectively referred to as "Sample 39" to 1-Sample 42].

Comparative Example 6 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 39 using a triarylamine derivative having the following structural formula as a carrier transporting substance in the formation of a carrier transporting layer. This will be referred to as "comparative sample 6."

Examples 43 to 47 In the formation of the carrier generation layer, a bisazo compound having the following structural formula was used as a carf generation substance, and in the formation of the carrier transport layer, exemplary compounds A-(5) and A-(9) were used as the carrier transport substance. , A-(61), A-
Five types of electrophotographic photoreceptors of the present invention were prepared in the same manner as in Example 1 except that each of those shown in (62) and A-(75) was used. These are respectively "sample 431~"
"Sample 47".

Comparative Example 7 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 43, except that a triarylamine derivative having the following structural formula was used as a carrier transport substance in forming the carrier transport layer. This will be referred to as "comparative sample 7."

Examples 48 to 51 In the formation of the carrier generation layer, a trisazo compound having the following structural formula was used as the carrier generation substance, and in the formation of the carrier transport layer, as the carrier transport substance, exemplary compounds A-(6), A-(44), A-(62
), A-(65), and the like were used in the same manner as in Example 1 to prepare four types of electrophotographic photoreceptors of the present invention. These are "Sample 48" to "Sample 5" respectively.
1".

Comparative Example 8 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 48, except that a triarylamine derivative having the following structural formula was used as a carrier transport substance in forming the carrier transport layer. This is referred to as "comparative sample 8."

Examples 52 to 55 A bisazo compound having the following structural formula was used as a carrier-generating substance in the formation of carrier-generating Jf'J, and exemplary compounds A-(1) and A-(33) were used as the carrier-transporting substance in forming the carrier-transporting layer. , A-(62),
Four types of electrophotographic photoreceptors of the present invention were prepared in the same manner as in Example 1, except that each of those shown by Δ-(75) was used. These are respectively referred to as "sample 52" to "sample 55."

Comparative Example 9 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 52, except that a triarylamine derivative having the following structural formula was used as a carrier transport substance in forming the carrier transport layer. This will be referred to as "comparative sample 9."

Examples 56 to 59 In the formation of the carrier generation layer, a bisazo compound having the following structural formula was used as the carrier generation substance, and in the formation of the carrier transport layer, A-(1) and A-(16) were used as exemplary compounds as the carrier transport substance. , A-(64),
Four types of electrophotographic photoreceptors of the present invention were prepared in the same manner as in Example 1 except that each of those shown in A-(66) was used. Comparative Example 10 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 56, except that a triarylamine derivative having the following structural formula was used as a carrier transport substance in the formation of the carrier transport layer. .This is referred to as "comparative sample 10."

Examples 60 to 63 In the formation of the carrier generation layer, a trisazo compound having the following structural formula was used as the carrier generation substance, and in the formation of the carrier transport layer, exemplary compounds A-(5) and A- were used as the carrier transport substance. (61), A-(62
) and A-(64) were used, but in the same manner as in Example 1, four types of electrophotographic photoreceptors of the present invention were prepared. These are designated as “Sample 60” to “Sample 6” respectively.
3".

Comparative Example 11 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 60, except that a triarylamine derivative having the following structural formula was used as the carrier transport substance in forming the carrier transport layer. This will be referred to as "Comparative Sample 11."

Examples 64 to 67 In the formation of the carrier generation layer, a bisazo compound having the following structural formula was used as the carrier generation substance, and in the formation of the carrier transport layer, exemplary compounds A-(6) and A-(24) were used as the carrier transport substance. ,A-(63),A
- Example 1 except that each of those shown in (67) was used.
An electrophotographic photoreceptor of the present invention was prepared in the same manner as described above. These will be referred to as "Sample 64" to "Sample 67", respectively.

Comparative Example 12 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 64, except that a triarylamine derivative having the following structural formula was used as the carrier transport material in forming the carrier transport layer. This will be referred to as "Comparative Sample 12."

For each of the electrophotographic photoreceptors of the present invention, Samples 1 to 67, and comparative electrophotographic photoreceptors, Comparative Samples 1 to 12, obtained as described above, "Electrostatic Paper Analyzer, sp 428 type" was used. '' (newly manufactured by Kawaguchi Denki) to investigate its electrophotographic characteristics. That is, in order to attenuate the acceptance potential VA (V) when the photoreceptor surface is charged at a charging potential of -6 KV for 5 seconds and the potential (initial potential) VI (V) after dark decay for 5 seconds. The required exposure amount E+ (lux·sec) was investigated.

In addition, using the same measurement method, the initial potential was set to -500 (V
) to -50 (V) are shown in Tables 1 to 5.

Table 1, Table 2, Table 3, Table 4, Table 5 As is clear from the above results, the electrophotographic photoreceptor of the present invention has superior sensitivity characteristics compared to the comparative electrophotographic photoreceptor, and in particular, It has excellent characteristics.

Example 68 An electrophotographic photoreceptor of the present invention was prepared by coating the same intermediate layer, carrier generation layer, and carrier transport layer as in Example 9 on the surface of an aluminum drum by a dip method.

This drum-shaped photoreceptor was modified for negative charging (dry type)
(manufactured by Rokusha Kogyo Co., Ltd.) and made continuous copies at 20,000:1B, it was faithful to the original image and had no fog.
A clear image with excellent gradation was obtained. This is 2G, 00
A stable image was obtained without any change over the 0-day period, demonstrating that the electrophotographic photoreceptor of the present invention has extremely excellent durability.

[Brief explanation of the drawing]

tIIJ1 to FIG. 6 each represent a cross-sectional view showing an example of the mechanical structure of the electrophotographic photoreceptor of the present invention. 1... Conductive support 2... Carrier generation layer 3...
・Carrier transport layer 4...Photosensitive layer 5...Intermediate layer 6...Layer containing a carrier transport substance 7...Carrier generating substance Agent Patent attorney No. 1) Parent-in-law - Engraving of drawings (Contents) No change) Horse 1 bad Horse? Figure) Figure 5 Sujito Zucho 1J11 Sansho (Type 11) July 11, 1980 Director General of the Patent Office Manabu Shiga 1.1 Display of 1980 Patent Application F553242 No. 2, Title of the Invention Electrophotographic photoreceptor: 3. Relationship with the person making the amendment Patent applicant address Higashijo: [1-chome Nishi-Shinjuku, Shinjuku-ku, Tokyo [No. 126-2 Name (]27) Konishiroku Photo Industry Co., Ltd. 4, Agent 〒1
91 Address: 1 Sakura-cho, Hino-shi, Tokyo 1982 6116+1 (shipped): June 2, 1980
6th) 6. Specification and drawings subject to amendment 7. Contents of amendment

Claims (1)

[Claims] (1) In an electrophotographic photoreceptor in which a photosensitive layer containing a carrier-generating substance and a carrier-transporting substance is provided on a conductive support, a triarylamine derivative represented by the following general formula [1] is used as the carrier-transporting substance. Contain!
An electrophotographic photoreceptor. General formula [1] (However, in the formula, A11++Ar12 is a substituted or unsubstituted 7enyl group, naphthyl A';, 'tk: I, these substituents include a substituted or unsubstituted furkyl group, a substituted or unsubstituted represents an alkenyl group, a substituted or unsubstituted alkoxy group, a halogen atom, an amine 7 group, a substituted amine 7 group, a substituted or unsubstituted phenoxy group, or a substituted or unsubstituted alkenyloxy group, R,, R2, R3 , R,, R5, R6, and R7 may be the same or different, and each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkoxy group. represents an alkenyloxy group, a substituted or unsubstituted phenoxy group, an ami7 group, a substituted ami7 group, a hydroxyl group, a halogen atom, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted acetyl group.However, Rs- (Except when R<-RssR6yRy are hydrogen atoms at the same time.)