JPS63113541A - Photoconductive composition - Google Patents

Abstract

PURPOSE:To improve preservable stability and sensitization efficiency of the titled composition by using a specific compd. as a sensitizing dye. CONSTITUTION:The sensitizing dye is composed of the compd. shown by the formula. In the formula, (n) and (m) are each 0-3, both (m) and (n) are not 0 simultaneously, (p) and (q) are each 0 or 1, L is a methine group, etc., R1 and R2 are each a substd. or an unsubstd. aliphatic hydrocarbon group, R3-R5 are each hydrogen atom, etc., Z1 and Z2 are each a non-metallic atomic group necessary for forming a 5- or 6-membered ring. The compounding amount of the sensitizing dye is 0.0001-20.0pts.wt. preferably 0.001-10.0pts.wt. per 100pts. wt. a photoconductive body. The sensitizing dye can be incorporated to a photosensitive layer solely of with combining said dyes. Thus, the sensitivity and the stability of the titled composition is remarkably improved.

Description

Detailed Description of the Invention <Industrial Application Field> The present invention provides a photoconductive composition comprising a photoconductor dispersed in a binder resin, in which the photoconductor is spectrally enhanced by a novel dye. The present invention relates to photoconductive compositions.

(Prior Art) Many spectral sensitizing dyes are already known in electrophotographic photosensitive layers of photoconductor-resin dispersion systems. There are various properties required of these spectral sensitizing dyes, including good adsorption to the photoconductor, high sensitization efficiency, and not lowering the resistance of the electrophotographic photosensitive layer in the dark more than necessary. is a particularly important point. Examples of dyes that meet these requirements are U.S. Pat. Nos. 3,052,540 and 3,110,591.
No. 3125447, No. 3128179, No. 31
No. 32942, No. 3241959 and No. 31210
No. 08 and British Patent No. 1,093,823.

On the other hand, dyes for spectral sensitization to red light or infrared rays are described in U.S. Pat. No. 3,619,154 and U.S. Pat. In particular, polymethine dyes with long methine chains (for example, 5 or more) have been the main focus.

<Problems to be Solved by the Invention> However, these dyes are generally easy to decompose, and are significantly degraded during the storage of the dye or during the manufacturing process and storage of the electrophotographic photosensitive layer, resulting in a significant practical problem in that the performance deteriorates. There were drawbacks. Harasaki et al. state that sensitizing dyes to red or infrared light are more unstable than sensitizing dyes to shorter wavelength light (visible light). (“Industrial Chemistry Magazine” Vol. 66, No. 2, p. 26 (1963)). In particular, this instability tends to increase as the methine chain in the sensitizing dye becomes longer. The appearance of a certain pigment is desired.

Furthermore, it is desired that dyes with high sensitization efficiency to long wavelength light as described above be developed.

Therefore, an object of the present invention is to provide a photoconductor-resin dispersion photoconductive composition containing a spectral enhancing dye that has excellent storage stability and high sensitization efficiency.

Another object of the present invention is to provide a photoconductive composition that can be used as a photoreceptor for electrophotography using a laser as a light source.

A further object of the present invention is to provide a photoconductive composition containing, as a spectral enhancer, a novel dye that is colorless and transparent, has absorption in far-infrared to near-infrared, and provides high sensitization efficiency. be.

(Means for Solving the Problems) In the above-mentioned aspect, in the photoconductive composition containing a photoconductor, an exacerbating dye, and a binder resin, the sensitizing dye is a compound represented by the following general formula (1). It has been found that this can be achieved by a photoconductive composition characterized in that:

General formula (1) % formula %) In formula [I], n and m are each 0. 1. Represents 2 or 3. However, m and n never become O at the same time.

p and q each represent 0 or 1.

L represents a methine group or a substituted methine group.

R and R2 are the same or different and each represents a substituted or unsubstituted aliphatic group.

R, , R, and R3 are each the same or different, and each represents a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group,
It represents a substituted or unsubstituted amino group or a halogen atom, and/or R3 and R4+R1 and R3 and/or R4 and R5 form a fused 6-membered ring.

ZI and Z2 are the same or different and each represents a group of nonmetallic atoms necessary to form a 5-membered ring or a 6-membered ring, and these rings may have a substituent, and It may be condensed with.

Xqma represents an anion.

r represents 1 or 2. However, when the dye forms an inner salt, r is 1.

Each substituent in the compound represented by general formula CI) is preferably the substituent shown below.

That is, R1 and R2 may be the same or different from each other, and are unsubstituted alkyl groups having 18 or less carbon atoms (for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, octyl group, decyl group, dodecyl group). , octadecyl group, vinylmethyl group, cyclohexyl group, etc.) or substituted alkyl group [substituents include, for example, carboxy group, sulfo group, cyano group, halogen atom (e.g., hydrogen atom, chlorine atom, bromine atom), hydroxy group , alkoxycarbonyl groups having 8 or less carbon atoms (e.g. methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group, benzyloxycarbonyl group, etc.), alkoxy groups having 8 or less carbon atoms (e.g. methoxy group, ethoxy group, benzyloxy group, phenethyl group) (oxy group, etc.), monocyclic aryloxy group having 10 or less carbon atoms (e.g. phenoxy group, p-tolyloxy group, etc.), acyloxy group having 3 or less carbon atoms (e.g. acetyloxy group, propionyloxy group, etc.), carbon number 8 or less acyl group (e.g. acetyl group, propionyl group, benzoyl group, mesyl group, etc.), carbamoyl group (e.g. carbamoyl group, N, N-dimethylcarbamoyl group, morpholinocarbonyl group, piperidinocarbonyl group, etc.), sulfamoyl group (For example, sulfamoyl group, N.

N-dimethylsulfamoyl group, morpholinosulfonyl group, piperidinosulfonyl group, etc.), aryl groups having 10 or less carbon atoms (e.g. phenyl group, 4-chlorophenyl group, 4-methylphenyl group, α-naphthyl group, etc.) An alkyl group having 18 or less carbon atoms substituted with

L represents a methine group or a substituted methine group, and as a substituent for the methine group, an alkyl group having 1 to 4 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, a butyl group, etc.)
, aryl group having 7 to 10 carbon atoms, substituted alkyl group (e.g. benzyl group, phenethyl group, 3-phenylpropyl group, 4-phenylbutyl group, etc.), carbon number 6 to 1
0 aryl group (e.g. phenyl group, naphthyl group, etc.)
is preferred.

It is also preferable to crosslink between methylene groups with a trimethylene group to form a 6-membered carbon ring on the methylene chain.

The alkyl groups for R3, R4 and R3 include lower alkyl groups having 1 to 4 carbon atoms (for example, methyl group, ethyl group,
isopropyl group, butyl group, etc.), and the alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms (eg, methoxy group, ethoxy group, propoxy group, butoxy group, etc.).

R3, R4, and R1 are unsubstituted or substituted amino or may be different, each of which is a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms (e.g., methyl group, F-/L4, propyl group, butyl group, etc.); Acyl groups having 2 to 8 carbon atoms (eg, acetyl group, propionyl group, benzoyl group, etc.) and aryl groups having 6 to 12 carbon atoms (eg, phenyl group, naphthyl group, etc.) are preferred.

It is also preferable that R6 and R1 are linked to each other to form a 5-membered ring or a 6-membered ring. Furthermore, R6 and/or R1 may be bonded to the benzene ring of the henzopyrylium ring to form a condensed ring.

Z and Z2 represent a group of nonmetallic atoms necessary to form a 5- or 6-membered ring, and the ring is, for example, a thiazole nucleus (e.g., thiazole, 4-methylthiazole, 4-phenylthiazole, 5-methylthiazole, 5 -phenylthiazole, 4,5-dimethylthiazole, 4,5-diphenylthiazole, 4, (2-chenyl)thiazole, etc.), benzothiazole nuclei (e.g. benzothiazole, 4-chlorobenzothiazole, 5-chlorobenzothiazole, 6
-Chlorobenzothiazole, 7-chlorobenzothiazole, 4-methylbenzothiazole, 5-methylbenzothiazole, 6-methylbenzothiazole, 5-bromobenzothiazole, 6-bromobenzothiazole, 5-trifluoromethylbenzothiazole, 5 -Phenylbenzothiazole, 4-methoxybenzothiazole, 5-methoxybenzothiazole, 6-methoxybenzothiazole, 5-carpoxyhenzothiazole, 5-cyanobenzothiazole, 5-fluorobenzothiazole, 5-ethoxybenzothiazole , tetrahydrobenzothiazole, 5,6-simethoxybenzothiazole, 5-hydroxybenzothiazole, 6-hydroxybenzothiazole, etc.), naphthothiazole core (e.g. naphtho-(1,2
-d) thiazole, naphtho(2,1-d]thiazole,
naphtho(2,3-d)thiazole, 5-methoxynaphthoC2,1-d)thiazole, 5-ethoxynaphtho(2,
1-d) Thiazole, 8-methoxynaphtho(1,2-d)
)thiazole, 7-methoxynaphtho(1,2-d)thiazole, etc.), oxazole nuclei (e.g. 4-methyloxazole, 5-methyloxazole, 4-phenyloxazole, 4.5-diphenyloxazole, 4-ethyloxazole, 4 5-dimethyloxazole, 5-phenyloxazole, etc.), benzoxazole nuclei (e.g. benzoxazole, 5-chlorobenzoxazole, 5-methylbenzoxazole, 5-phenylbenzoxazole, 6-methylbenzoxazole, 5.6
-Simethylbenzoxazole, 4,6-dimethylhenzoxazole, 5-methoxybenzoxazole, 5
-ethoxybenzoxazole, 5-fluorobenzoxazole, 6-methoxybenzoxazole, 5-hydroxybenzoxazole, 6-hydroxybenzoxazole, etc.), naphthoxazole nuclei (e.g. naphtho(1,2-d)oxazole, naphtho(2, 1-d) oxazole, naphtho[2,3-d) oxazole, etc.),
Selenazole core (e.g. selenazole, 4-methylselenazole, 4-phenylselenazole, 4,5-diphenylselenazole, etc.), benzoselenazole core (e.g. benzoselenazole, 5-chlorobenzoselenazole,
5-methylbenzoselenazole, 5-methoxybenzoselenazole, 5-phenylbenzoselenazole, etc.), naphthoselenazole core (e.g. naphtho(1,2-d)selenazole, naphtho(2,3-d)selenazole, etc.) ), imidazole core (e.g. 1-ethylimidazole, 1-benzylimidazole, etc.), benzimidazole nucleus (e.g. 1. 3-diethylbasiimidazole, 1,3-diethyl-5,6-cyclopenzimitazole, 1. 3
-diethyl-5-trifluoromethyl-6-chlorobenzimidazole, 1. 3-diethyl-5-cyano-6
-chlorobenzimidazole, etc.), naphthoimidazole nuclei (e.g., IH-naphtho(2,3-d)imidazole, etc.), thiazoline nuclei (e.g., thiazoline, 4-methylthiazoline, 4-phenylthiazoline, etc.), imidazoquinoline nuclei (e.g., IH -imidazo(4,5-b]quinoline etc.), imidazo(4,5-b)quinoxaline nucleus (e.g. 1
．． 3-diethylimidazo(4,5-b)quinoxaline,
1,3-diallylimidazoC4,5-b) Quinoxaline, 1,3-diphenylimidazo(4,5-b) Quinoxaline 6-chloro-1,3-diethyl-imidazo[4,.

5-b] Quinoxaline, 6-chloro-1,3-diallylimidazo (4,5-t)) quinoxaline, 6,7-dichloro-1,3-diphenylimidazo (4,5-b) quinoxaline, etc.), oxazoline nucleus (e.g. 5,5-dimethyloxazoline etc.), isoxazole nucleus (e.g. 5,5-dimethyloxazoline etc.),
-methylisoxazole, etc.), benzisoxazole nucleus (e.g. benzisoxazole, etc.), 3,3-dialkylindolenine nucleus (e.g. 3,3-dimethylindolenine, 3,3,5-trimethylindolenine, 5-
Chloro-3,3-dimethylindolenine, 5-ethoxycarbonyl-3,3-dimethylindolenine, 5-carboxy-3,3-dimethylindolenine, 5-sulfo-
3,3-dimethylindolenine, etc.), 2-pyridine nucleus (
For example, pyridine, 5-methylpyridine, etc.) 4-pyridine nucleus (for example, pyridine, etc.), 2-quinoline nucleus (for example, 6-
nitoxyquinoline, 6-ethylquinoline, 6-chloroquinoline, 8-fluoroquinoline, etc.), 4-quinoline nucleus (e.g. 8-methylquinoline, 8-)fluoroquinoline,
6-chloroquinoline, etc.), 1-isoquinoline core (eg, isoquinoline, etc.) are preferred.

X- represents an anion, and specifically preferred are chloride, bromide, iosito, thiocyanate, perchlorate, valatoluenesulfonate, and tetrafluoroborade.

Specific examples of the compound represented by general formula (1) are listed below, but the present invention is not limited thereto.

Compound-1 CI! 040 Compound-9 Compound-10 Compound-12 czo4C) Compound-16 Compound-17 Compound-19 Compound-20 Compound-21 Compound-22 Compound-23 Compound-24 C1○40 Compound-25 Compound-26 Compound-27 Compound- 28 H3CCH3C1o, 0 Compound-29 Compound-30 Compound-31 Compound-32 Compound-33 Compound-34 Compound-35 Compound-36 Compound-37 The compound represented by general formula (1) can be synthesized by various synthesis methods. For example, as shown in the reaction formula below,
Intermediate (A) obtained by reaction of a heterocyclic/quaternary salt derivative having an active methyl group and a 4-methylthiocoumarin derivative
and intermediate [B].

(XρLl-1 (XpLz-+ Intermediate (A) Intermediate CB) In the above formula, Y represents a leaving group that is often used when synthesizing a dye, such as a halogen atom (such as a chlorine atom)
, substituted amino groups (e.g. N-acetylanilino group, dimethylamino group, etc.), substituted mercapto groups (e.g. methylthio group, ethylthio group, 3-sulfopropylthio group, 4
-sulfobutylthio group, etc.), sulfonate i, alkoxy groups (eg, methoxy group, ethoxy group, phenoxy group, etc.).

○　　　○ X,,X, represent anions.

r, , r2, r, , represent 1 or 2, and are 1 when the molecule forms an inner salt.

R+, R2, R3, R4, R5, Zl -Zz, n%
m, , p, and q have the same meanings as explained in general formula (1).

In addition to the above-mentioned synthetic methods, for example, US Pat.
31,105, Ukr, Khim,
Zh, Vol. 46, No. 9, pp. 965-971 (1980)
It can be synthesized using the method described in .

Next, a synthesis example of the compound represented by the general formula (1) of the present invention will be explained in detail using the following synthesis example.

Synthesis Example-1 (Synthesis of Intermediate (A)) 1-(1) 3-ethyl-2-[(4-methyl-2
H-chromen-2-ylidene) methylbenzothiazolium perchlorate 17.5 g of -toluenesulfonate and 8.8 g of 4-methylthiocoumarin were heated at 150°C for 15 hours. After that, add 20mj of methanol to the reaction mixture! Then, acetone 4QmA was added to make a homogeneous solution. After cooling to room temperature, 60% perchloric acid 1
When 5.7 g was added and stirred at room temperature, crystals were precipitated. Collect the crystals by filtration, wash with a small amount of acetone, and then add 20ml of methanol at room temperature! ! The crystals were added to a mixed solvent of 40 m6 of acetone, stirred for 30 minutes, collected by filtration, and washed with acetone to obtain the desired product 8.
．． 5g was obtained. (Yield 40%) Brown crystal mp 280°C or higher (decomposition) 1-(2)
5-1-Lifluoromethyl-3-ethyl-2-[(
4-Methyl-2H-chromen-2-ylidene)methyl]-benzothiazolium p-1-luenesulfonate 5-trifluoromethyl-3-ethyl-2-methylbenzothiazolium p-toluenesulfonate2. 37g
After heating and reacting 1.0 g of 4-methylthiocoumarin at 150 DEG C. for 20 hours, 10 mj2 of methanol, then 10 ml of acetone, and 20 ml of ethyl acetate were added to the reaction mixture to form a homogeneous solution. When cooled to room temperature, crystals precipitated. The crystals were collected by filtration, washed with a small amount of acetone, and then mixed with 1 Q ml of methanol, 10 ml of acetone, and 20 ml of ethyl acetate at room temperature.
The crystals were added to a mixed solvent of m1, stirred for 40 minutes, collected by filtration, and washed with acetone to obtain 1.4.7 g of the desired product.

(Yield 46%) Brown crystal mp 272-273°C (decomposition) 1-(3)
5-chloro-3-ethyl-2-[(4-methyl-2
H-chromen-2-ylidene) methyliobenzothiazolium p-toluenesulfonate 5-chloro-3-ethyl-2-methylbenzothiazolium p-toluenesulfonate 11.1 g and 4-methylthiocoumarin 5.5 g After heating and reacting at 150°C for 23 hours, 25 ml of methanol, then 50 ml of acetone and 150 rrl of ethyl acetate were added to the reaction mixture, and upon cooling to room temperature, crystals were precipitated. The crystals were collected by filtration, washed with a small amount of acetone, and then mixed with 25 mL of methanol and 50 mL of acetone at room temperature.
m! The crystals were added to a mixed solvent of 15 Qml of ethyl acetate, stirred for 20 minutes, collected by filtration, and washed with acetone to obtain the desired product 7.
．． 9g was obtained. (Yield 52%) Brown crystal m9282
~283°C (decomposition) 1-(4) 5-methyl-3
-Ethyl-2-[(4-methyl-2H-chromen-2-ylidene)methylbenzothiazolium perchlorate 5-methyl-3-ethyl-2-methylbenzothiazolium p-)luenesulfonate 2.07 g. After heating and reacting 1.0 g of 4-methylthiocoumarin at 150°C for 25 hours, 1 methanol was added to the reaction mixture.Qmj! Next, 10 ml of acetone and 20 ml of ethyl acetate were added, and when the mixture was cooled to room temperature, crystals were precipitated. After the crystals were collected by filtration and washed with a small amount of acetone, 20 mf of methanol and then 40 ml of acetone were added to form a homogeneous solution at room temperature. 5 g of 60% perchloric acid was added thereto, and after stirring at room temperature for 30 minutes, the precipitated crystals were collected by filtration and washed with acetone to obtain 1.46 g of the desired product.

(Yield 55%) Brown crystals m+) 27 Q ~ 275°C (decomposition) 1-(
5) 5-methoxy-3-ethyl-2-((4-methyl-2H-chromen-2-ylidene)methyl)penzothiazolium iodide 5-methoxy-3-ethyl-2-methylbenzothiazolium After a heating reaction of 2.15 g of p-) luenesulfonate and 1.0 g of 4-methylthiocoumarin at 150°C for 20 hours, 15 ml of methanol and 1 liter of acetone were added to the reaction mixture.
2mj+ was added to make a homogeneous solution. 1.7 g of sodium iodide (5 ml of acetone solution) was added dropwise to this solution and stirred at room temperature to precipitate crystals. After collecting the crystals by filtration and washing with a small amount of acetone, the crystals were added to 20 ml of room temperature sewage water, stirred for 15 minutes, collected by filtration, and washed with acetone to obtain the desired product 1.
02g was obtained. (Yield 38%) Brown crystal mp 27
3-274℃ (decomposition) 1-(6) 3-ethyl-2
-((4-Methyl-2H-chromen-2-ylidene)methyl)-naphtho(2,1-d)thiazolium iosito3-ethyl-2-methylnaphtho-(2,1-d)thiazolium iosito2. 27g and 4-methylthiocoumarin 1
．． After reacting Og by heating at 150° C. for 21 hours, 8 mff1 of methanol and then 12 ml of acetone were added to the reaction mixture to form a homogeneous solution. Add 1.7 sodium iodide to this solution.
g (5 ml of water solution) was added dropwise and stirred at room temperature for 1 hour to precipitate crystals.

The crystals were collected by filtration and washed with a small amount of acetone, then added to a mixed solvent of 15 ml of sewage water and 15 mj2 of acetone at room temperature, stirred for 15 minutes, collected by filtration, and washed with acetone to obtain the desired product.
．． 8g was obtained. (Yield 28%) Brown crystal mp28
0°C or higher (decomposition) 1-(7) 3-ethyl-2-(
(4-Methyl-2H-chromen-2-ylidene)methyl)naphtho(1,2-d) thiazolium iosito 3-ethyl-2-methylnaphtho(1,2-d) thiazolium iosito 2.27 g and 4-methylthiocoumarin1.
From 0 g, 0.08 g of the target product was obtained in the same manner as in 1-(6). (Yield 3.5%) Brown crystals ml) 140-1
42°C (decomposition) Synthesis Example 2 (Compound-1) 2-((3-ethyl-2(3H)-benzothiazolinylidene)methyl)-4-(3-(3-ethyl-2(3H)
-benzothiazolinylidene)propenyl)-5,6-benzopyrylium perchlorate 3-ethyl-2-((4-methyl-2H-chromene-2
-ylidene)methyl)-benzothiazolium perchlorate 2.8 g and 2-(2-acetanilidevinyl)-3
- Add 3.0 g of ethylbenzothiazolium iodide to 150 m of ethanol, heat to reflux, and then add 6 m of triethylamine! ! added. The reaction mixture was cooled to room temperature for 15 minutes, and the precipitated crystals were collected by filtration. The obtained crude crystals were purified by silica gel column chromatography (developing solvent: methanol/chloroform = 1/8) and then recrystallized (twice) from methanol/chloroform = 2/8 to obtain 1.7 g of the target product. . Mental brown crystals, yield 43%, melting point 26
0-262℃ (decomposition), max
m a x8X
10'.

Synthesis Example 3 (Compound-2) 2-((3-ethyl-2(3H)-benzothiazo linylidene)methyl)-4-(3-(3-ethylnacito(
1,2-d)-thiazolinylidene)propenyl)-5,
6-benzopyrylium perchlorate 3-ethyl-2-((4-methyl-2H-chromene-2
-ylidene)methyl)benzothiazolium verchlorate 3.0g and 2-(2-acetanilidevinyl)-3-
Ethylnaphtho(1,2-d)thiazolium p-)riensulfonate3. 9 g was added to 150 ml of ethanol, and after heating under reflux, 6 ml of triethylamine was added. 1
After reacting for 5 minutes, the mixture was cooled to room temperature and the precipitated crystals were collected by filtration.

The obtained crude crystals were purified by silica gel column chromatography (developing solvent: methanol/chloroform = 2/8) and then recrystallized (twice) from methanol/chloroform = 2/8 to obtain 1.8 g of the target product. . Bright brown crystals, yield 38%, max Synthesis example 4 (Compound-7) 2-((3-ethyl-2(3H)-benzothiazolinylidene)methyl)-4-(5- (3-ethyl-5,6-dimethyl-2(3H)-benzothiazolinylidene)-3-
Methyl-1,3-pentadienyl)-5,6-benzopyrylium perchlorate 3-ethyl-2-((4-methyl-2H-chromene-2
-ylidene)methyl)benzothiazolium p-) 3.3 g of luenesulfonate and 2-(4-ethoxy-3-methyl-1,3-butadienyl)-3-ethyl-5,6-
3.1 g of dimethylbenzothiazolium iosite was added to 150 ml of ethanol, and after heating to reflux, 6 ml of triethylamine was added. After reacting for 12 minutes, cool to room temperature,
The precipitated crystals were collected by filtration. The resulting crude crystals were purified by silica gel column chromatography (developing solvent: methanol/chloroform = 2/8), and then 500 ml of methanol was added.
A solution of 1.8 g of sodium perchlorate dissolved in 100 rrl of water was added. The precipitated crystals were collected by filtration and recrystallized from methanol-chloroform (twice) to obtain 2.7 g of the desired product.

Bright brown crystals, yield 56%, melting point 200-202℃2,
17X10S.

Synthesis Example 5 (Compound-9) 2-((3-ethyl-2(3H)-benzothiazolinylidene)methyl)-4-(3-(3-ethyl-2(3H)
-benzoxazolinylidene)propenyl)-5,6-
Benzopyrylium perchlorate 3-ethyl-2-((4-methyl-2H-chrome-2-
3.0 g of ylidene) methyl) benzothiazolium perchlorate, 3.1 g of 2-(2-anilinovinyl)-3-ethylbenzoxacilium ethanesulfur) and 5 ml of acetic anhydride in DMF 100 mj! After heating at 100°C for 5 minutes, add 6mj2 of triethylamine, and then heat for 5 minutes.
The reaction was heated for a minute. After cooling to room temperature, the precipitated crystals were collected by filtration, and the resulting crude crystals were recrystallized (twice) from methanol-chloroform to obtain 2.6 g of the target product. Dark green crystals, yield 62%, melting point 268-270"C Used as a sensitizer for photoconductive materials.

As the inorganic photoconductive substance, zinc oxide, titanium oxide, zinc sulfide, cadmium sulfide, etc. can be used. Examples of organic photoconductive substances include polymeric substances.
The following (1) to (5) can be mentioned.

(1) Polyvinylcarbazole and its derivatives described in Japanese Patent Publication No. 34-10966, (2) Japanese Patent Publication No. 43-1
Polyvinylpyrene, polyvinylanthracene, poly-2 described in JP-A No. 8674 and Japanese Patent Publication No. 43-19192
-vinyl-4-(4'-dimethylaminophenyl)-5
-vinyl polymers such as phenyl-oxazole and poly-3-vinyl-N-ethylcarbazole; (3) polyacenaphthylene, polyindene, and copolymers of acenaphthylene and styrene described in Japanese Patent Publication No. 19193-1973; (4) Condensation resins such as pyrene-formaldehyde resin, brompyrene-formaldehyde resin, and ethylcarbazole-formaldehyde resin described in Japanese Patent Publication No. 56-13940, (5) JP-A No. 56-9083.3 , 56-1615
Various triphenylmethane polymers described in Publication No. 50.

Examples of low molecular weight compounds include the following (6) to (18).

(6) Triazole derivatives described in US Pat. No. 3,112,197, etc.; (7) Oxadiazole derivatives, described in US Pat. No. 3,189,447, etc.;
Imidazole derivatives described in Publication No. 16096, etc. (9) U.S. Patent No. 3615402, U.S. Patent No. 382098
No. 9, No. 3542544, Special Publication No. 45-555, No. 10983-1983, Japanese Patent Publication No. 93224-1971,
JP-A-55-77105, JP-A-56-4148,
JP-A-55-108667, JP-A-55-15695
No. 3, polyarylalkane derivatives described in JP-A-56-36656, publications, etc. (10) U.S. Pat. No. 3180729, U.S. Pat. No. 42787
No. 46, JP-A-55-88064, JP-A-55-88
No. 065, JP-A-49-105537, JP-A-55-
No. 51086, JP-A-56-80051, JP-A-56
-88141, JP-A-57-45545, JP-A-5
Pyrazoline derivatives and pyrazolone derivatives described in No. 4-112637, JP-A-55-74546, publications, etc.

(11) U.S. Patent No. 3,615,404, Japanese Patent Publication No. 5
1-10105, JP-A-54-83435, JP-A-54-110836, JP-A-54-119925,
Phenyldiamine derivatives described in Japanese Patent Publication No. 46-3712, Japanese Patent Publication No. 47-28336, publications, etc. (12) U.S. Patent No. 3567450, Japanese Patent Publication No. 49-3
No. 5702, West German Patent (DAS) No. 1110518,
U.S. Patent No. 3180703, U.S. Patent No. 324059
No. 7, U.S. Patent No. 3,658,520, U.S. Patent No. 423
No. 2103, U.S. Patent No. 4175961, U.S. Patent No. 4012376, JP 55-144250, JP 56-119132, JP 39-27577,
(13) Amino-substituted chalcone derivatives described in U.S. Pat. No. 3,526,501; (14) U.S. Pat. No. 3,542,546. (15) Oxazole derivatives described in U.S. Pat. No. 3,257,203, etc., (16) Styryl anthracene derivatives described in JP-A-56-46234, etc., (17) Fluorenone derivatives described in JP-A-54-110837, etc., (18) U.S. Patent No. 3717462, JP-A-54-5
9143 (corresponding to U.S. Patent No. 415098), JP 55-52063, JP 55-52064, JP 55-46760, JP 55-85495, JP 57-11350 No., Japanese Patent Publication No. 57-14874
Vidrazone derivatives disclosed in Patent No. 9, Publication No. 1, etc.

Two or more of these photoconductive substances may be used in combination depending on the case.

Among these photoconductive materials are poly-N-vinylcarbazole; triarylamines such as tri-p-tolylamine and triphenylamine; 4,4'-bis(diethylamine)-2°2'-dimethyltriphenyl; polyarylmethane such as methane; and 3-(4
-dimethylaminophenyl)-1,5-diphenyl-2
-Unsaturated heterocycle-containing compounds represented by pyrazoline derivatives such as pyrazoline are preferably used.

The photoconductive composition of the present invention containing the polymethine dye of formula (1) of the present invention as a sensitizer can be obtained by dissolving these dyes, a photoconductive substance, and a binder resin in an organic solvent.

This can be coated onto a conductive support by a commonly used method such as spin coating, blade coating, knife coating, reverse roll coating, dip coating, rod bar coating, or spray coating, and dried and used as a photoreceptor. It can be used as a photosensitive layer (photoconductive layer) in a single-stone type electrophotographic photosensitive material, and can also be used as a charge carrier in a functionally separated electrophotographic photosensitive material having two layers: a charge carrier generation layer and a charge carrier transport layer. It can be used as a generation layer.

The photoconductive composition of the present invention can also be used in a photoelectrophoresis method by producing particles from the above organic solvent solution using a mini-spray device or the like, and dispersing the particles in an insulating liquid. .

The photoconductive composition of the present invention can be used as a photoconductive layer in the image pickup tube of a red- or infrared-sensitive video camera, or over a one-dimensional or two-dimensional array of semiconductor circuits for known signal transfer or scanning. It can be used as a photoconductive layer sensitive to red light or infrared rays of a solid-state image sensor having a light-receiving layer (semiconductive layer).

The method of using the sensitizing dye when used as an ordinary electrophotographic photoreceptor in the present invention may be according to a conventionally known method, which involves dispersing the photoconductor in a binder resin and then adding a dye solution. Particularly convenient methods include placing the photoconductor in advance in a dye solution, adsorbing the dye, and then dispersing it in a binder resin. The amount of sensitizing dye used in the present invention varies over a wide range depending on the degree of sensitization required. That is, it can be used in an amount of 0.0001 to 20.0 parts by weight per 100 parts by weight of the photoconductor, but preferably in a range of o, ooi to 10.0 parts by weight.

The sensitizing dyes used in the present invention can be contained in the photosensitive layer singly or in combination of two or more.

Depending on the purpose, the sensitizing dye of the present invention may also be used with other conventionally known spectral sensitizing dyes (for example, rose bengal, eosin,
Needless to say, it can be used in combination with

In addition, acid anhydrides and the like are sometimes added to zinc oxide, which is one of the photoconductors, to promote spectral sensitization, but in the present invention, the stability of the sensitizing dye of the present invention is sufficient. It is advantageous in that various conventionally known additives for electrophotographic photosensitive layers can be used in combination.

As the binder that can be combined, all conventionally known binders can be used. Typical examples include vinyl chloride-vinyl acetate copolymer, styrene-butyl methacrylate copolymer, styrene-butyl methacrylate copolymer, polymethacrylate, polyacrylate, polyvinyl acetate, polyvinyl butyral, alkyd resin, silicone resin, and epoxy. resin, epoxy ester resin, polyester resin, etc.

It is also possible to combine it with an aqueous acrylic emulsion or an acrylic ester emulsion.

For examples of specific polymeric materials useful as binders, see Research Disclosure.
H Disclosure), Volume 109, Pages 61-67, under the title "Electrophotographic Elements, Materials and Methods".

Generally, sensitizing dyes are susceptible to oxidation, and therefore, it is desirable to avoid using them together with catalyst compounds that promote oxidation.

For example, among vinyl polymerization initiators, care must be taken when using peroxides such as benzoyl peroxide, and organic acid salts of heavy metals that promote hardening of unsaturated fatty acids. Regarding this point, even the sensitizing dye used in the present invention requires the same level of consideration as conventional sensitizing dyes, but conventional polymethine dyes cannot be used in combination with these oxidation promoters. However, the problem was that it disintegrated in a short period of time. However, when the dye of formula (I) of the present invention is used, its stability is significantly improved.

Generally, the amount of binder present in the photoconductive compositions of the present invention can vary. Typically, useful amounts of binder range from about 10 to about 90% by weight, based on the total amount of the photoconductive material and binder mixture.

The electrophotographic photosensitive layer according to the present invention can be provided on a conventionally known support. Generally speaking, the support for the electrophotographic photosensitive layer is preferably electrically conductive, such as a metal plate or a plastic film provided with a conductive layer (for example, a thin film made of aluminum, palladium, indium oxide, tin oxide, cuprous iodide, etc.). (layers), conductive-treated gi, etc. are often used. Polymers containing quaternary ammonium salts (for example, polyvinylbenzyltrimethylammonium chloride, US Pat. No. 4,108,802) can be used as conductive treatment agents for paper.
No. 4118231; No. 4126467; No. 41
A polymer containing quaternary nitrogen in the main chain as described in No. 37217,
U.S. Patent No. 4,070,189; Japanese Patent Application Publication No. 54-20977
Quaternary salt polymer latex (described in sclosure #16258), polystyrene sulfonate salts, colloidal alumina, etc. are well known, and can usually be used in combination with polyvinyl alcohol, styrene-butadiene latex, gelatin, casein, etc. many.

As the organic solvent used for dispersion, a volatile hydrocarbon solvent with a boiling point of 200°C or less is used, and in particular, a volatile hydrocarbon solvent having 1 to 3 carbon atoms such as dichloromethane, chloroform, 1,2-dichloroethane, tetrachloroethane, dichloropropane or trichloroethane is used. Halogenated hydrocarbons are preferred.

Various other solvents used in coating compositions, such as aromatic hydrocarbons such as chlorobenzene, toluene, xylene or benzene, ketones such as acetone or 2-butanone, ethers such as tetrahydrofuran, and methylene chloride, and mixtures of the above solvents may also be used. Available for use.

Solvent contains dye, photoconductive material and other additives
1 to 100g is added per 1g, preferably 5 to 20g.

The coating thickness of the photoconductive composition of the present invention on a suitable support is:
Can vary widely. Typically, coatings can be applied within the range of about 10 microns to about 300 microns (before drying). The preferred range of coating thickness before drying is approximately 5
It was found to be in the range of 0 microns to about 150 microns. However, useful results can be obtained even outside this range. The dry thickness of this coating may range from about 1 micron to about 50 microns.

Furthermore, as another mode of use of the composition of the present invention, a sensitizer can be incorporated into particles used for photoelectrophoresis to obtain images by photoelectrophoresis. Particles used in the photoelectrophoresis method are produced from a solution consisting of a photoconductive substance such as poly-N-vinylcarbazole and the sensitizer of the present invention using a mini-spray apparatus. These particles can also be used in insulating liquids containing saturated hydrocarbons such as decane, dodecane, octane, paraffin, isooctane, etc.
Preferably Isopar E, Iso-H1 Isopar G
(manufactured by Esso Chemical Co., Ltd., trade name) or the like to form a dispersion liquid, which is used for photoelectrophoresis. Isopar E1 Isopar H and
Isopar G contains 99.9.99 saturated hydrocarbons, respectively.
．． 3 and 99.8% by weight, and 0.05.0.2 and 0.2% by weight of aromatic hydrocarbons, respectively. However, Isopar H contains 0.5% by weight or less of olefin. The respective boiling points are 115℃~142"C, 174℃
~189°C and 158°C to 177°C. The amount of particles in the dispersion is from 0.5 to 10% by weight, preferably from 1 to 3% by weight, based on the dispersion.

Regarding the photoelectrophoresis method and its equipment, see 45-2 Japanese Patent Publication.
No. 0640.

Necessary additives may be appropriately added to the photoconductive layer and particles in order to improve the properties of the photoconductive layer and particles.

In the photoelectrophoresis method described above, for example, an electrically insulating binder component can also be present in the photoconductive composition of the present invention. Preferred binders used in making the photoconductive compositions of the present invention are film-forming, hydrophobic polymeric binders with fairly high dielectric strength and good electrical insulation properties. A typical example of such a substance is as follows. ; Natural resins such as vinyl resins, gelatin, cellulose ester derivatives, and cellulose nitrate; Polycondensates including polyesters and polycarbonates; Silicone resins; Alkyd resins including styrene-alkyd resins; Paramine; and various mineral waxes, etc. .

Generally, the amount of binder in the photoconductive compositions of the present invention can vary, and typically useful amounts of binder are from about 10 to about 90% by weight, based on the total amount of the photoconductor and binder mixture. is within the range of

Charge control agents and dispersion stabilizers may also be added when producing photoconductive particles. In particular, a copolymer of lauryl methacrylate and styrene (copolymerization ratio 4 to 2:1) or a copolymer of 2-ethylhexyl methacrylate and styrene (copolymerization A ratio of 4:2 to 1) and the like are advantageously used.

In addition to the above-mentioned dispersion stabilizer, the photoconductive composition of the present invention generally contains a plasticizer such as chlorinated diphenyl, dimethyl phthalate, and an epoxy resin (trade name Epicote) to improve flexibility and strength. Up to 60 parts by weight, preferably 10 to 40 parts by weight, can be added to 00 parts by weight of the photoconductive material.

In addition, in order to improve the strength, JP-A-58-65438
No., JP-A-58-65439, JP-A-58-1022
No. 39, JP-A-58-102240, JP-A-58-1
Urea compounds, thiourea compounds, carbonylamine compounds, thiocarbonylamine compounds, which are respectively described in No. 07544 and JP-A-58-129434,
A chemical sensitizer such as a sulfonylamine compound or a dicarbonylamine compound is added in an amount of 1 to 100 parts by weight, preferably 3 to 50 parts by weight, per 100 parts by weight of the photoconductive substance.
An overlapping section can also be added.

(Example) The present invention will be described below with reference to specific examples, but the content of the present invention is not limited to these.

Examples 1 to 7 Bo+7-N-vinylcarbazole (trade name Rubican 17
0. BASF (1 day, 25°C, in THF) 5g, 1st
Dye 35■ of the specific compound example shown in the table, 30mg of 3,3'-dinitrobenzanilide and methylene chloride 26
mf and ethylene chloride at 12 mA to prepare a photosensitive solution.

This photosensitive solution was applied to a conductive transparent support (a 100 μm polyethylene terephthalate support with a surface resistance of
03Ω) to obtain an organic thin film having a photosensitive layer of about 4μ.

This organic thin film was heated to 400cm by +5kV corona discharge.
The amount of exposure required to attenuate the potential by half, that is, the half-reduced exposure amount E! 4 (erH/c+d) was measured.

As a light source, a galylium-aluminum-arsenic semiconductor laser (oscillation wavelength: 780 μm) was used.

The results are shown in Table 1.

Table 1 1 (1) 61.0 2 (2) 55.2 3 (7) 49.8 4(1↓)45.6 5 (12) 53.1 6 (21) 50.2 7 (34) 48.5 *) Indicated by the number of the above compound example.

From the above, it can be seen that the photoreceptor using the sensitizing dye of the present invention has 7
It can be seen that it responds to light with a long wavelength of 80 μm.

Example 8 As an organic photoconductive substance, 5 g of 4,4'-bis(diethylamino)-2,2'-dimethyltriphenylmethane,
Bisphenol A polycarbonate (
Manufactured by GE, trade name Lexan 121) 5g: 40mg of the dye of compound example (1), and 0.2g of an anilide compound with the following structural formula as a chemical sensitizer, and methylene chloride 3Q
mj! was dissolved in 30 ml of ethylene chloride to prepare a photosensitive solution.

An organic thin film was prepared in the same manner as in Example 1, and when Ez was measured, EV2 was 54. 8 (erg/cffll).

(Anilide compound) Examples 9 to 21 As an organic photoconductive substance, 5 g of 4,4'-bis(diethylamino)-2,2'-dimethyltriphenylmethane,
Bisphenol A polycarbonate (
Manufactured by GE, trade name: Lexan 121) 5 g, dye 40 as a specific example of the compound shown in Table 2, 0.2 g of an anilide compound with the following structural formula as a chemical aggravator, methylene chloride 30
rnβ and ethylene chloride 3Qmj! A photosensitive solution was prepared. An organic thin film was produced in the same manner as in Example 1.

(Anilide compound) The photoreceptor produced in this way was
P-428 (manufactured by Kawaguchi Electric Co., Ltd.) was used to corona charge the sample at 15 KV using a stacitor method, and after holding the sample in a dark place for 30 seconds, it was exposed to light at an illuminance of 2 nux to examine the charging characteristics. The charging characteristics are determined by the initial charging potential (■0) and how much the potential after 30 seconds of dark decay is maintained with respect to the initial potential (■0), that is, the dark charge retention rate (DRR). (%)・
And the same EV2 as in Example 1 was measured. The results are shown in Table 2.

Table 2 Examples 24 to 26 Particulate zinc oxide (average particle size 0.5 to 1 μm, manufactured by Sakai Chemical Co., Ltd. 5azsx2000Q) 100 parts (all parts mean parts by weight), acrylic resin (Diamond manufactured by Mitsubishi Rayon Co., Ltd.) LROO9e) 30 parts of 40% by weight toluene solution, 0.02 parts of phthalic anhydride, 60 parts of toluene, 1°OX 1 of each of the dyes of the specific examples of compounds shown in Table 3.
0-jMo 7! A dispersion was prepared by mixing 8 parts of a dye solution containing 1/1 methanol and kneading for 2 hours in a porcelain ball mill.

This dispersion was applied onto an aluminum foil to a dry yield of about 8 μm, and then dried in a constant temperature bath at 50° C. for 2 hours to produce an electrophotographic photoreceptor.

Charging characteristics: Vo, DRR,
E! 4 was measured. The results are shown in Table 3.

Table 3 Example 27 and Comparative Example A 100 parts of fine particulate zinc oxide (average particle size 0.5 to 1 μm, 5azex2000Q manufactured by Sakai Chemical Co., Ltd.) (all parts mean parts by weight), acrylic resin (manufactured by Mitsubishi Rayon Co., Ltd.) Dianal LROO9Q) 40% by weight l luene solution 3
0 parts, 60 parts of toluene and the compound (37) of the present invention in 1.0 parts. OXIO-3Moj2/(l) of methanol solution and dye solution were mixed together and 2 parts were mixed in a porcelain ball mill.
A dispersion was prepared by kneading for a period of time.

This dispersion was coated on aluminum foil with a dry film of about 4 to 8 mL, respectively.
An electrophotographic photoreceptor (1) was prepared by applying the coating to a thickness of .mu.m and then drying it in a constant temperature bath at 50.degree. C. for 2 hours.

On the other hand, photoreceptor A was treated in exactly the same manner as above except that the following comparative compound was used instead of the above compound (37).
was created.

(Comparative Compound A) Regarding the above two types of photoreceptors, spectral reflectance was measured and spectral photographs were taken by ordinary electrophotography using a liquid developer using a carbon blank as a toner.

As a result of measuring the spectral reflectance, the electrophotographic photosensitive layer containing Compound (37) showed a clear absorption maximum at a wavelength of 784 nm, but the electrophotographic photosensitive layer containing the comparative compound had a wavelength of 800 nm.
No absorption was observed near m.

As a result of spectrophotography, the electrophotographic photosensitive layer containing compound (37) showed a response in the specific photosensitive range of ZnO around a wavelength of 380 nm, as well as a response due to spectral aggravation in the wavelength range corresponding to the spectral reflectance mentioned above. showed that.

On the other hand, in the electrophotographic photosensitive layer containing the comparative compound, no response other than the response in the ZnO specific photosensitive region was observed.

In other words, it was revealed that the electrophotographic photosensitive layer containing Comparative Compound A was not spectrally sensitized.

On the other hand, these photoreceptors (1) and A are charged to -400V by corona discharge of -6KV, and the exposure amount required for the potential to attenuate to 2, that is, the half-reduced exposure amount E% [e
rg/cni] was measured.

A gallium-aluminum-arsenic semiconductor laser (oscillation wavelength: 780 nm) was used as a light source.

Electrophotographic photoreceptor (1) of the present invention using compound (37)
The E% of was 56 [erg/cni], whereas
Photoreceptor A using Comparative Compound A showed no photosensitivity.

The above results were due to the fact that Comparative Compound A disappeared due to decomposition due to its instability, and such decomposition occurred when preparing a dispersion of the composition, in which zinc oxide, etc. and a pigment were added in advance, and then the compound A was placed in a ball mill. It is presumed that the dye was decomposed during the dispersion because it was dispersed for 2 hours. On the other hand, it can be seen that the sensitizing dye of the present invention exists stably even under such processing conditions and exhibits a spectral sensitizing effect.

Example 28 and Comparative Example B Regarding the two types of compounds shown in Example 27, Example 27
An electrophotographic photosensitive layer was prepared using a method different from that of the previous method.

100 parts of fine particulate zinc oxide (average particle size 0.5 to 1 μm, manufactured by Sakai Chemical Co., Ltd., 5azex20QOQ), styrenated alkyfd resin (Styresol #42 manufactured by Nippon Reichhold Co., Ltd.)
35 parts of a 25% by weight toluene solution of 50o) and 40 parts of toluene were mixed and kneaded in a porcelain ball mill for 2 hours to prepare a white dispersion. Add 25% of polyisocyanate resin (Nippon Reichhold Co., Ltd., Burnock D-750e) to this dispersion.
15 parts of a butyl acetate solution was added and stirred thoroughly for 3 minutes.Furthermore, 10 parts each of the two types of methanol solutions shown in Example 27 were added to this dispersion and stirred well. These two types of dispersions were each applied onto aluminum foil to a dry film thickness of 10 μm, and then dried in a constant temperature bath at 50° C. for 15 hours to obtain two types of electrophotographic photosensitive layer materials. Of the two types of materials thus obtained, the materials having electrophotographic photosensitive layers containing Comparative Compound A and Compound (37) are named Comparative Sample B and Sample (2), respectively.

Spectral reflectance and spectral sensitivity by electrophotography were measured for these two types of samples. The absorbance at the maximum absorption wavelength in the spectral reflectance wavelength range of 700 nm to 850 nm was measured for the two types of samples immediately after production and after storage for one week under conditions of 50°C and 80% RH, and the absorbance after the accelerated test was calculated. The stability was estimated by using the value divided by the absorbance immediately after as the stability value. The closer the stability value is to 1, the more stable it is. Stability values are listed in Table 4. In this example, in order to prevent the decomposition of the dye during the preparation of the photosensitive layer, a method was adopted in which zinc oxide and resin were dispersed in advance and then the dye was added. Furthermore, in order to suppress the promotion of decomposition of the dye, a resin with an acid value of zero was used.

Comparative sample B in Table 4 has a maximum reflectance at a wavelength of 800n immediately after manufacture.
around m (corresponding to the maximum absorption wavelength of the comparison compound) and around 380 nrn (corresponding to the maximum absorption wavelength of ZnO)
However, after the accelerated test, the wavelength was 800 nm.
The maximum reflectance near m disappeared and the spectral absorbance curve became flat, and only the maximum reflectance near a wavelength of 380 nm was observed.

This fact indicates that the comparative compound in the electrophotographic photosensitive layer disappeared under accelerated test conditions.

On the other hand, for sample (2), the degree of spectral exacerbation immediately after manufacture and after the accelerated test was measured in the same manner as in Example 27, and a spectral sensitivity ratio almost equivalent to the above stability value was obtained. In other words, it was revealed that sample (2) achieved the desired spectral enhancement to almost the same extent by compound (37) immediately after production and after the accelerated test.

(Effects of the Invention) The photoconductive composition of the present invention is a highly sensitive photoreceptor that exhibits a sufficient sensitizing effect. In particular, the dye group of the present invention, which is sensitized to a long wavelength range of 750 nm or more, can achieve significantly higher sensitivity and significantly improved stability compared to conventional laser electrophotographic photoresists.

That is, the present invention overcomes the drawback that conventional electrophotographic photosensitive layers containing cyanine dyes cannot withstand long-term storage by using aggravating dyes having the above-described characteristic skeleton structure. Not only has the decomposition of the sensitizing dye been reduced during the production of the photosensitive layer, but the photosensitive layer can also be used under harsh test conditions such as 50°C and 80% R, H (relative humidity). In comparison, it has a remarkable effect in that it shows very good stability. In particular, it has much greater stability than conventionally used red or infrared sensitizing dyes.

Since the dye is highly stable, the method of using the aggravating dye in the present invention does not require consideration such as setting special dispersion mixing conditions or carefully selecting the timing of addition, so the process of manufacturing the photosensitive material is simplified. This has the advantage of stabilizing the quality and performance of photosensitive materials. Furthermore, when inorganic photoconductors such as zinc oxide, titanium oxide, zinc sulfate, and cadmium sulfide are used as photoconductors, the coexistence of these photoconductors with sensitizing dyes can cause problems, especially those known in the art under light irradiation. Sensitizing dyes tend to be easily decomposed, and in particular when using red or infrared sensitizing dyes, restrictions such as carrying out photosensitive layer manufacturing work in the dark have been necessary. It is also a significant effect of the present invention that such restrictions are significantly relaxed.

Representative Patent Attorney (8107) Kiyoshi Sasaki (and 3 others) Procedural amendment January 28, 1988

Claims (1)

[Scope of Claims] A photoconductive composition containing a photoconductor, a sensitizing dye, and a binder resin, characterized in that the sensitizing dye is a compound represented by the following general formula [I]. Conductive composition. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula [I], n and m each represent 0, 1, 2, or 3. However, m and n never become 0 at the same time. p and q each represent 0 or 1. L represents a methine group or a substituted methine group. R_1 and R_2 are the same or different and each represents a substituted or unsubstituted aliphatic group. R_3, R_4 and R_5 are each the same or different and each represents a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, a substituted or unsubstituted amino group or a halogen atom, and/or R_3 and R_4, R_3 and R_5 and/ Or R_4 and R_5 form a fused 6-membered ring. Z_1 and Z_2 are the same or different, and each represents a group of nonmetallic atoms necessary to form a 5-membered ring or a 6-membered ring, and these rings may have a substituent and are incompatible with other rings. May be condensed. X^■ represents an anion. r represents 1 or 2. However, when the dye forms an inner salt, r is 1.