JPH10282701A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To form a eutectic complex-contg. photosensitive layer having superior electrophotographic sensitivity and high wear resistance by forming a photoconductive layer contg. a eutectic complex consisting essentially of a pyrylium dye and a polycarbonate having a triarylamine structure in the principal chain and/or a side chain on an electrically conductive substrate. SOLUTION: A photoconductive layer contg. a eutectic complex consisting essentially of a pyrylium dye and a polycarbonate having a triarylamine structure in the principal chain and/or a side chain is formed on an electrically conductive substrate or a photoconductive layer contg. a eutectic complex consisting essentially of a pyrylium dye and a high molecular electric charge transferring material represented by the formula is formed on an electrically conductive substrate. In the formula, each of R1 -R3 is alkyl or halogen, R4 is H or alkyl, each of R5 and R6 is aryl, each of (o) to (q) is an integer of 0-4, (k) and (j) show the ratio between units, 0.1<=k<=1, 0<=j<=0.9, (n) is an integer of 5-5,000 as the number of repeating units and X is a divalent aliphatic group, a divalent alicyclic group, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member, and is suitably used for a copying machine, a laser printer, a laser facsimile, and the like.

[0002]

2. Description of the Related Art As an electrophotographic method, a Carlson process and various other deformation processes are known.
Widely used in copiers and printers. Among the photoreceptors used in such an electrophotographic method, those using an organic photosensitive material have recently been used because of their advantages such as low cost, mass productivity, and no pollution.

[0003] Organic electrophotographic photoreceptors include a photoconductive resin represented by polyvinyl carbazole (PVK), P
VK-TNF (2,4,7-trinitrofluorenone)
There are known charge-transfer complex type typified by the formula (I), pigment dispersion type typified by the phthalocyanine-binder, and function-separated type photoreceptors using a combination of a charge generating substance and a charge transporting substance.

[0004] In recent years, photoconductors having a single-layer photosensitive layer have been reviewed from the viewpoint of cost and the like. Heretofore, as the single-layer photosensitive layer, those in which a charge transporting substance and a charge generating substance are dispersed in a binder resin, a eutectic complex type photosensitive layer, and the like have been proposed.
In particular, an electrophotographic photoreceptor having a photoconductive layer made of a eutectic complex comprising a pyrylium-based dye and an electrically insulating polymer and, if necessary, a composition containing a triphenylmethane-based sensitizer is known (for example, JP-B-46-22518, JP-B-46-22519, JP-B-51-1129, JP-A-47-10785, and JP-A-51-88.
226, JP-A-51-93324, JP-A-53-87227, etc.). These photoconductors have an electrophotographic sensitivity that is practically acceptable, but do not have satisfactory characteristics. In order to improve these, sensitizers have been studied, and relatively high-sensitivity photoconductors have been manufactured (for example, JP-A-63-206760, JP-A-63-213851, and Kaisho 63-
No. 213853).

However, the photosensitive layers of these photoreceptors use a sensitizer mainly composed of a low-molecular charge transport material dispersed in the photosensitive layers. For this reason, it is generally soft and has a drawback that the Carlson process is likely to cause film shaving due to repeated use. Improvement in this respect has been desired.

[0006]

An object of the present invention is to provide a photoreceptor having a eutectic complex photosensitive layer having excellent electrophotographic sensitivity and high abrasion resistance. More specifically, it is an object of the present invention to provide a photosensitive member having particularly excellent electrophotographic sensitivity when positively charged. Another object of the present invention is to provide a low-cost photoreceptor that can be easily manufactured.

[0007]

Means for Solving the Problems As described above, the object of the present invention is to provide (1) a method in which a conductive support is mainly provided with a pyrylium dye and a polycarbonate containing a triarylamine structure in a main chain and / or a side chain. An electrophotographic photoreceptor characterized in that a photoconductive layer containing a eutectic complex as a component is provided. " (2) A feature is that a photoconductive layer containing a eutectic complex containing a pyrylium-based dye and a polymer charge transporting material represented by the following formula (1) as main components is provided on a conductive support. Electrophotographic photoreceptor.

[0008]

Embedded image In the formula, R ₁ , R ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group or a halogen atom, R ₄ is a hydrogen atom or a substituted or unsubstituted alkyl group, and R ₅ and R ₆ are substituted or unsubstituted. A substituted aryl group, o, p, and q each independently represent an integer of 0 to 4, k and j each represent a composition, and 0.1 ≦
k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units and is an integer of 5 to 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula.

[0009]

Embedded image In the formula, R ₁₀₁ and R ₁₀₂ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom.
l and m are integers from 0 to 4, Y is a single bond, and has 1 to 1 carbon atoms.
2 linear, branched or cyclic alkylene groups, -O
-, - S -, - SO -, - SO 2 -, - CO -, - CO
—O—Z—O—CO— (wherein, Z represents an aliphatic divalent group) or

[0010]

Embedded image (In the formula, a represents an integer of 1 to 20, b represents an integer of 1 to 2,000, and R ₁₀₃ and R ₁₀₄ represent a substituted or unsubstituted alkyl group or aryl group.) Here, R ₁₀₁ and R ₁₀₂ and R ₁₀₃ and R ₁₀₄ may be the same or different. (3) a photoconductive layer comprising a eutectic complex containing a pyrylium-based dye and a polymer charge-transporting material represented by the following formula (2) as main components on a conductive support: Electrophotographic photoreceptor.

[0011]

Embedded image In the formula, R ₇ and R ₈ represent a substituted or unsubstituted aryl group, A
r ₁ , Ar ₂ and Ar ₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). And (4) "a photoconductive layer comprising a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (3) as main components is provided on a conductive support." Electrophotographic photoreceptor.

[0012]

Embedded image In the formula, R ₉ and R ₁₀ are a substituted or unsubstituted aryl group,
Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). (5) A photoconductive layer comprising a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (4) as main components is provided on a conductive support. Electrophotographic photoreceptor.

[0013]

Embedded image In the formula, R ₁₁ and R ₁₂ are a substituted or unsubstituted aryl group,
Ar ₇ , Ar ₈ and Ar ₉ are the same or different arylene groups, p
Represents an integer of 1 to 5. X, k, j and n are the same as in the case of the above equation (1). (6) A feature is that a photoconductive layer containing a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (5) as main components is provided on a conductive support. Electrophotographic photoreceptor.

[0014]

Embedded image In the formula, R ₁₃ and R ₁₄ are a substituted or unsubstituted aryl group,
Ar ₁₀ , Ar ₁₁ and Ar ₁₂ are the same or different arylene groups,
X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group. X, k, j and n are the same as in the case of the above equation (1). ”, (7)
"Electrophotographic photosensitive material characterized in that a photoconductive layer containing a eutectic complex containing a pyrylium dye and a polymer charge transport material represented by the following formula (6) as main components is provided on a conductive support. body.

[0015]

Embedded image In the formula, R ₁₅ , R ₁₆ , R ₁₇ and R ₁₈ are a substituted or unsubstituted aryl group, Ar ₁₃ , Ar ₁₄ , Ar ₁₅ and Ar ₁₆ are the same or different arylene groups, Y ₁ , Y ₂ and Y ₃ are A single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom, and a vinylene group may be the same or different. X, k, j and n are the same as in the case of the above equation (1). (8) "A photoconductive layer comprising a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (7) as main components is provided on a conductive support. Electrophotographic photoreceptor.

[0016]

Embedded image In the formula, R ₁₉ and R ₂₀ represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₉ and R ₂₀ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). And (9) that a photoconductive layer containing a eutectic complex containing a pyrylium dye and a polymer charge transport material represented by the following formula (8) as main components is provided on a conductive support. Electrophotographic photoreceptor.

[0017]

Embedded image In the formula, R ₂₁ is a substituted or unsubstituted aryl group, A
r ₂₀ , Ar ₂₁ , Ar ₂₂ and Ar ₂₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). (10) A photoconductive layer comprising a eutectic complex containing a pyrylium-based dye and a polymer charge-transporting material represented by the following formula (9) as main components is provided on a conductive support. Electrophotographic photoreceptor.

[0018]

Embedded image In the formula, R ₂₂ , R ₂₃ , R ₂₄ , and R ₂₅ are a substituted or unsubstituted aryl group, Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ , Ar ₂₈
Represents the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). ”, (11)
"Electrophotographic photosensitive material characterized in that a photoconductive layer containing a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (10) as main components is provided on a conductive support. body.

[0019]

Embedded imageWhere R₂₆, R₂₇Is a substituted or unsubstituted aryl group,
Ar₂₉, Ar₃₀, Ar ₃₁Represents the same or different arylene groups
Express. X, k, j and n are the same as in the case of the above equation (1).
The same. Is achieved.

(12) The method according to (1) to (1), wherein the photoconductive layer contains a low-molecular charge transport material.
The electrophotographic photosensitive member according to any one of the above (11). "
Achieved by

(13) The electrophotographic photosensitive member according to the above (12), wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (11).

[0022]

Embedded image In the formula, R ₂₀₁ , R ₂₀₂ , R ₂₀₃ and R ₂₀₄ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted aryl group, and Ar ₁₀₁ represents a substituted or unsubstituted aryl group, Ar ₁₀₂ represents a substituted or unsubstituted arylene group, Ar ₁₀₁ and R ₂₀₁ may jointly form a ring, and n ₁ is an integer of 0 or 1. (14) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (12).

[0023]

Embedded image In the formula, R ₂₀₅ represents a lower alkyl group, a lower alkoxy group or a halogen atom, n ₂ represents an integer of 0 to 4,
R ₂₀₆ and R ₂₀₇ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. (15) "The following (1)
(3) The electrophotographic photoreceptor according to the above (12), comprising a low-molecular charge transporting material represented by the formula:

[0024]

Embedded image In the formula, R ₂₀₈ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group or a heterocyclic group;
₂₀₉ and R ₂₁₀ may be the same or different and include a hydrogen atom,
Lower alkyl group, a hydroxyalkyl group C ₁ -C _4, C
₁ -C ₄ a chloroalkyl group, or a substituted or unsubstituted aralkyl group, also, R ₂₀₉ and R ₂₁₀ may form a heterocyclic ring containing a nitrogen jointly, R _211, R ₂₁₂ are each the same And may be different, and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. (16) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transport material represented by the following formula (14).

[0025]

Embedded image In the formula, R ₂₁₃ represents a hydrogen atom or a halogen atom;
₂₁₄ is a substituted or unsubstituted aromatic residue or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, Selected from the group consisting of an alkoxy group and a nitro group). (17) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transport material represented by the following formula (15).

[0026]

Embedded image In the formula, R ₂₁₅ , R ₂₁₆ and R ₂₁₇ each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a heterocyclic group, and at least two of R ₂₁₅ , R ₂₁₆ and R ₂₁₇ are aryl. Represents a group or a heterocyclic group. (18) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transport material represented by the following formula (16).

[0027]

Embedded image In the formula, Ar ₁₀₃ and Ar ₁₀₄ each represent a substituted or unsubstituted aryl group or a heteroaromatic ring. ”, (1
9) The above-mentioned (1), wherein the photoconductive layer contains a low-molecular-weight charge transporting material represented by the following formula (17).
The electrophotographic photosensitive member according to the item 2).

[0028]

Embedded image In the formula, Ar ₁₀₅ represents a substituted or unsubstituted aryl group or a heteroaromatic ring, and R ₂₁₈ and R ₂₁₉ are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a heterocyclic group, respectively. _At least one of ₂₁₈ and R ₂₁₉ comprises an aryl group or a heterocyclic group. "
(20) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transport material represented by the following formula (18).

[0029]

Embedded image In the formula, R ₂₂₀ and R ₂₂₂ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group,
R ₂₂₁ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group, and n ₃ represents an integer of 0 or 1. (21) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (19).

[0030]

Embedded image In the formula, R ₂₂₃ represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, or a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group (provided that the substituent is a di-lower alkyl group). Amino group, lower alkyl group, lower alkoxy group, halogen atom, aralkylamino group or amino group). (22) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transport material represented by the following formula (20).

[0031]

Embedded image In the formula, Ar ₁₀₆ represents a substituted or unsubstituted biphenylene group, and R ₂₂₄ , R ₂₂₅ and R _{226 each} represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group, an alkoxy group which may have a substituent, Aryloxy group, alkyl mercapto group, methylenedioxy group, methylenedithio group,
Represents an aryl group, and R ₂₂₄ , R ₂₂₅ and R ₂₂₆ may be the same or different. U, v, and w each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₂₂₄ , R ₂₂₅ and R ₂₂₆ may be the same or different. (23) The electrophotographic photoreceptor according to the above (12), wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (21).

[0032]

Embedded image Wherein, R ₂₂₇ and R ₂₂₈ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R ₂₂₇
And at least one of R ₂₂₈ represents a substituted or unsubstituted aryl group. Is achieved.

The present inventors have found that a eutectic complex comprising a pyrylium-based dye and a polycarbonate containing a triarylamine structure in a main chain and / or a side chain exhibits extremely excellent electrophotographic sensitivity and extremely high abrasion resistance. The present inventors have found that the present invention exhibits the property, and have led to the present invention. Therefore, the electrophotographic photoreceptor of the present invention is provided with a eutectic complex (photosensitive layer) comprising at least a pyrylium-based dye and a polycarbonate containing a triarylamine structure in a main chain and / or a side chain, on a conductive support. It is characterized by having. More specifically, the present invention is characterized in that a polycarbonate containing a triarylamine structure in a main chain and / or a side chain is a polymer charge transport material represented by the above formulas (1) to (10).

Further, the present inventors have proposed a pyrylium dye 1
It has been found that the sensitivity characteristics of an electrophotographic photoreceptor having a composition of 5 to 100 parts by weight of a polymer charge transporting substance with respect to parts by weight are excellent. Further, the use of the polymer charge transporting material of the above formulas (1) to (10) makes it possible to reduce the possibility of dispersing the low molecular weight charge transporting material in the eutectic complex photosensitive layer comprising an electrically insulating polymer and a pyrylium dye. It was found that the wear resistance was much higher. Further, a small amount of a low-molecular-weight pigment is added to the photosensitive layer of the eutectic complex comprising a pyrylium-based dye and a polycarbonate containing a triarylamine structure in the main chain and / or the side chain [the polymer charge transport material of the above formulas (1) to (10)]. It has been found that by containing a molecular charge transporting substance [particularly, a low molecular weight charge transporting substance represented by the formulas (11) to (21) is good], sensitivity characteristics can be improved with almost no decrease in wear resistance. The present invention has been completed.

Next, the present invention will be described with reference to the drawings. FIG. 1 is a cross-sectional view showing a configuration example of a photoreceptor used in the present invention. A eutectic complex photosensitive layer (31) is formed on a conductive support (21). FIG. 2 is a cross-sectional view showing another configuration example, in which an intermediate layer (25) is provided between a conductive support (21) and a eutectic complex photosensitive layer (31).
FIG. 3 is a cross-sectional view showing still another configuration example, in which a charge transport layer (33) is laminated on a conductive support (21) and a eutectic complex photosensitive layer (31). FIG. 4 shows an electrophotographic composite photoreceptor as an application example of the present invention. A photosensitive layer (35) (hereinafter, referred to as a second photosensitive layer) having sensitivity to light transmitted through the eutectic complex photosensitive layer (31) is provided on the conductive support (21), and the eutectic complex is formed thereon. A photosensitive layer (31) is provided.

As the conductive support (21), one having conductivity of 10 ¹⁰ Ω or less, for example, aluminum, nickel, chromium, nichrome, copper, silver, gold, platinum,
Metals such as iron, oxides such as tin oxide and indium oxide coated on film or cylindrical plastic or paper by evaporation or sputtering, or plates of aluminum, aluminum alloy, nickel, stainless steel, etc. D. I. , I. I. A pipe or the like that has been surface-treated by cutting, superfinishing, polishing, or the like after it is formed into a tube by a method such as extrusion, drawing, or the like can be used.

As described above, the eutectic complex photosensitive layer (31)
Is a polycarbonate containing a pyrylium-based dye and a triarylamine structure in a main chain and / or a side chain, more specifically, a polycarbonate made of a pyrylium-based dye and a polymer charge transport material represented by the above formulas (1) to (10). is there. There are three types of pyrylium dyes, pyrylium salts, thiapyrylium salts, and selenapyrylium salts, having the following general formula.

[0038]

Embedded image In the above formula, R ₄₀₁ , R ₄₀₂ , R ₄₀₃ , R ₄₀₄ , and R ₄₀₅ are respectively (a) a hydrogen atom, (b) methyl, ethyl, propyl, isopropyl, butyl, t-butyl, amyl,
Isoamyl, hexyl, octyl, nonyl, alkyl C ₁ -C _15, such as dodecyl, (c) methoxy, ethoxy, propoxy, butoxy, amyloxy, hexoxy,
Alkoxy groups such as octoxy, (d) phenyl, 4-
Alkylphenyls such as diphenyl, 4-ethylphenyl, 4-propylphenyl; 4-ethoxyphenyl,
4-methoxyphenyl, 4-amyloxyphenyl, 2-
Hexoxyphenyl, 2-methoxyphenyl, 3,4-
Alkoxyphenyls such as diethoxyphenyl; 2-
Β-hydroxyalkoxyphenyls such as hydroxyethoxyphenyl and 3-hydroxyethoxyphenyl;
4-hydroxyphenyl, 2,4-dichlorophenyl,
3,4-dibromophenyl, 4-chlorophenyl, 3,
Halophenyls such as 4-dichlorophenyl; aminophenyls such as azidophenyl, nitrophenyl, 4-diethylaminophenyl and 4-dimethylaminophenyl; naphthyl, styryl, methoxystyryl, diethoxystyryl, dimethylaminostyryl, 1-butyl-4
-Represents an aryl group including a substituted aryl group such as a vinyl-substituted aryl group such as p-dimethylaminophenyl-1,3-butadienyl and β-ethyl-4-dimethylaminostyryl. X is a sulfur, oxygen or selenium atom, and Z ^- is perchlorate, fluoroborate, iodide, chloride, bromide, lead sulfate, periodide,
Anionic functional groups such as p-toluenesulfonate and hexafluorophosphate. Further, R ₄₀₁ ,
R ₄₀₂ , R ₄₀₃ , R ₄₀₄ , and R ₄₀₅ may be the atoms necessary to complete an aryl ring fused to the pyrylium nucleus. Representative examples of such pyrylium dyes are shown below.

[0039]

[Table 1-1]

[0040]

[Table 1-2]

[0041]

[Table 1-3]

[0042]

[Table 1-4]

[0043]

[Table 1-5]

[0044]

[Table 1-6]

[0045]

[Table 1-7]

[0046]

[Table 1-8]

[0047]

[Table 1-9] Particularly useful pyrylium dyes are those having the general formula:

[0048]

Embedded image Wherein R ₄₀₆ and R ₄₀₇ are a C ₁ -C ₆ alkyl group and C ₁
An aryl group such as a substituted phenyl group having at least one substituent selected from a C ₆ alkoxy group, and R ₄₀₈ is a C ₁ -C ₆ alkylamino-substituted phenyl group, wherein the alkyl moiety is a dialkylamino-substituted phenyl group. And a haloalkylamino-substituted phenyl group. X is oxygen, sulfur,
Alternatively, the selenium atom and Z ^- are as described above.

Next, the polymer charge transporting material used in the present invention will be described. Polycarbonates containing a triarylamine structure in the main chain and / or side chain are examples of the polymer charge transporting material in the present invention. Among them, polymer charge transport materials represented by the following formulas (1) to (10) are particularly useful. The polymer charge transporting substances represented by the formulas (1) to (10) are exemplified below, and specific examples are shown.

[0050]

Embedded image In the formula, R ₁ , R ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group or a halogen atom, R ₄ is a hydrogen atom or a substituted or unsubstituted alkyl group, and R ₅ and R ₆ are substituted or unsubstituted. A substituted aryl group, o, p, and q each independently represent an integer of 0 to 4, k and j each represent a composition, and 0.1 ≦
k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units and is an integer of 5 to 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula.

[0051]

Embedded image In the formula, R ₁₀₁ and R ₁₀₂ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom.
l and m are integers from 0 to 4, Y is a single bond, and has 1 to 1 carbon atoms.
2 linear, branched or cyclic alkylene groups, -O
-, - S -, - SO -, - SO 2 -, - CO -, - CO
—O—Z—O—CO— (wherein, Z represents an aliphatic divalent group) or

[0052]

Embedded image (In the formula, a represents an integer of 1 to 20, b represents an integer of 1 to 2,000, and R ₁₀₃ and R ₁₀₄ represent a substituted or unsubstituted alkyl group or aryl group.) Here, R ₁₀₁ and R ₁₀₂ and R ₁₀₃ and R ₁₀₄ may be the same or different.

Specific examples of formula (1) R ₁ , R ₂ and R ₃ each independently represent a substituted or unsubstituted alkyl group or a halogen atom, and specific examples thereof include the following. , May be the same or different.

The alkyl group is preferably C ₁ -C ₁₂
In particular, it is a C ₁ -C ₈ , more preferably a C ₁ -C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C ₁ -C ₄ alkoxy group, It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl, trifluoromethyl, 2-hydroxyethyl,
2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl group, 4
-Methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. R ₄ represents a hydrogen atom or a substituted or unsubstituted alkyl group,
Specific examples of the alkyl group include R ₁ , R ₂ and R ₃ described above.
And the same. R ₅ and R ₆ represent a substituted or unsubstituted aryl group (aromatic hydrocarbon group and unsaturated heterocyclic group). Specific examples thereof include the following, and even if they are the same, they are different. You may.

As the aromatic hydrocarbon group, a phenyl group,
As a condensed polycyclic group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a , D] cycloheptenylidenephenyl group, and a non-fused polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

The above aryl group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. As the alkyl group, the above R ₁ ,
The same as R ₂ and R ₃ can be mentioned.

(3) Alkoxy group (-OR ₁₀₅ ). Examples of the alkoxy group (—OR ₁₀₅ ) include those in which R ₁₀₅ is an alkyl group defined in the above (2), and specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group. Groups, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) an aryloxy group. As the aryloxy group,
Aryl groups include those having a phenyl group and a naphthyl group. This is a C ₁ -C ₄ alkoxy group, C ₁
It may contain a C ₄ to C ₄ alkyl group or a halogen atom as a substituent. Specifically, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group, 4-methoxypheninoxy group, 4-chlorophenoxy group, 6-methyl-2-naphthyloxy group, and the like Is mentioned.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) an alkyl-substituted amino group. Examples of the alkyl-substituted amino group include those in which the alkyl group is the alkyl group defined in the above (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group,
And an N, N-dibenzylamino group. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

The structural part represented by X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (A) by a phosgene method, a transesterification method, or the like.
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. The structural part represented by X is also introduced into the repeating unit by a polymerization reaction of a diol compound having a triarylamino group of the following general formula (A) with a bischloroformate derived from the following general formula (B). Is done. In this case, the polycarbonate produced is an alternating copolymer.

[0061]

Embedded image Specific examples of the diol compound of the general formula (B) include the following. 1,3-propanediol, 1,4
-Butanediol, 1,5-pentanediol, 1,6
-Hexanediol, 1,8-octanediol, 1,
10-decanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-1,3-propanediol, diethylene glycol, triethylene glycol, polyethylene glycol, poly Aliphatic diols such as tetramethylene ether glycol and 1,4-cyclohexanediol,
1,3-cyclohexanediol, cyclohexane-
And cyclic aliphatic diols such as 1,4-dimethanol.

As the diol having an aromatic ring,
4,4′-dihydroxydiphenyl, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) -1-phenylethane, 2,2 -Bis (4-hydroxyphenyl) propane, 2,2-bis (3-methyl-4-hydroxyphenyl) propane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 1,1-
Bis (4-hydroxyphenyl) cyclopentane, 2,
2-bis (3-phenyl-4-hydroxyphenyl) propane, 2,2-bis (3-isopropyl-4-hydroxyphenyl) propane, 2,2-bis (4-hydroxyphenyl) butane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane, 4,4′-dihydroxydiphenylsulfone,
4'-dihydroxydiphenylsulfoxide, 4,4 '
-Dihydroxydiphenyl sulfide, 3,3'-dimethyl-4,4'-dihydroxydiphenyl sulfide,
4,4'-dihydroxydiphenyl oxide, 2,2-
Bis (4-hydroxyphenyl) hexafluoropropane, 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxyphenyl) xanthene, ethylene glycol-bis (4-hydroxybenzoate), diethylene glycol- Bis (4-hydroxybenzoate), triethylene glycol-bis (4
-Hydroxybenzoate), 1,3-bis (4-hydroxyphenyl) -tetramethyldisiloxane, phenol-modified silicone oil and the like.

[0063]

Embedded image In the formula, R ₇ and R ₈ represent a substituted or unsubstituted aryl group, A
r ₁ , Ar ₂ and Ar ₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the expression (1).

Specific examples of the formula (2) R ₇ and R _{8 each} represent a substituted or unsubstituted aryl group. Specific examples thereof include the following, which may be the same or different. . As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
Terphenylyl group, or

[0065]

Embedded image (Where W is -O-, -S-, -SO-, -SO
Represents _2- , -CO- or the following divalent group. )

[0066]

Embedded image

[0067]

Embedded image

[0068]

Embedded image

[0069]

Embedded image Is represented by

Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group and a carbazolyl group. The arylene groups represented by Ar ₁ , Ar ₂ and Ar ₃ include the divalent groups of the aryl groups represented by R ₇ and R ₈ , which may be the same or different. The above-mentioned aryl group and arylene group may have the following groups (1) to (7) as substituents. Also,
These substituents have the same meanings as R ₁₀₆ , R ₁₀₇ and R ₁₀₈ in the above general formula.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. The alkyl group is preferably C
₁ -C ₁₂ especially more preferably C ₁ -C ₁₈ linear or branched alkyl group of C ₁ -C _4, these alkyl groups may further fluorine atom, a hydroxyl group, a cyano group, a C ₁ -C ₄ Alkoxy group, phenyl group, or halogen atom, C _1-
It may contain a phenyl group substituted with a C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (—OR ₁₀₉ ). The alkoxy group (-OR _109), represents an alkyl group as defined R ₁₀₉ is (2). Specifically, methoxy, ethoxy, n-propoxy, i-propoxy, t-butoxy, n-butoxy, s-butoxy, i-butoxy, 2-hydroxyethoxy, 2-cyanoethoxy, benzyloxy , 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) an aryloxy group. As the aryloxy group,
Aryl groups include those having a phenyl group and a naphthyl group. This is a C ₁ -C ₄ alkoxy group, C ₁
It may contain a C ₄ to C ₄ alkyl group or a halogen atom as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) an alkyl-substituted amino group represented by the following formula:

[0074]

Embedded image In the formula, R ₁₁₀ and R ₁₁₁ each independently represent an alkyl group or an aryl group defined in the above (2). As the aryl group include a phenyl group, a biphenyl group, a naphthyl group, which alkoxy group C ₁ ~C _4, C ₁ ~
It may contain a C ₄ alkyl group or a halogen atom as a substituent. Further, a ring may be formed together with a carbon atom on the aryl group. Specific examples of the alkyl-substituted amino group include a diethylamino group, an N-methyl-N-phenylamino group, an N, N-diphenylamino group, an N, N-di (p-tolyl) amino group, a dibenzylamino group, Examples include a piperidino group, a morpholino group, and a julolidyl group.

(7) An alkylenedioxy group or an alkylenedithio group such as a methylenedioxy group or a methylenedithio group.

When the diol compound having a triarylamino group represented by the following general formula (C) is polymerized by a phosgene method, a transesterification method, or the like,
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Further, the structural part of X is introduced into the repeating unit also by a polymerization reaction between a diol compound having a triarylamino group of the following general formula (C) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0077]

Embedded image Examples of the diol compound of the general formula (B) include the same as the diol compound of the formula (1).

[0078]

Embedded image In the formula, R ₉ and R ₁₀ are a substituted or unsubstituted aryl group,
Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. X, k, j and n are the same as in the case of the expression (1).

Specific examples of formula (3) R ₉ and R ₁₀ represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. . As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

The arylene groups represented by Ar ₄ , Ar ₅ and Ar ₆ include the divalent groups of the aryl groups represented by R ₉ and R ₁₀ , which may be the same or different. The above-mentioned aryl group and arylene group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. As the alkyl group, preferably,
C ₁ -C _12, especially C ₁ -C ₈ , more preferably C ₁ -C
₄ is a linear or branched alkyl groups, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ ~
A C ₄ alkoxy group, a phenyl group, or a halogen atom,
It may contain a phenyl group substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (—OR ₁₁₂ ). Examples of the alkoxy group (—OR ₁₁₂ ) include those in which R ₁₁₂ is an alkyl group defined in the above (2), and specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) Aryloxy group. Examples of the aryloxy group include a phenyl group and a naphthyl group as the aryl group. This is a C ₁ -C ₄ alkoxy group, C ₁
It may contain a C ₄ to C ₄ alkyl group or a halogen atom as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.

(6) Alkyl-substituted amino group. As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group,
And an N, N-dibenzylamino group. (7) acyl group; specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When the diol compound having a triarylamino group represented by the following general formula (D) is polymerized by a phosgene method, a transesterification method, or the like,
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. The structural part of X is also introduced into the repeating unit by a polymerization reaction between a diol compound having a triarylamino group of the following general formula (D) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0086]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0087]

Embedded image In the formula, R ₁₁ and R ₁₂ are a substituted or unsubstituted aryl group,
Ar ₇ , Ar ₈ and Ar ₉ are the same or different arylene groups, p
Represents an integer of 1 to 5. X, k, j and n are (1)
Same as for expressions.

Specific examples of the formula (4) R ₁₁ and R ₁₂ represent a substituted or unsubstituted aryl group. Specific examples thereof include the following, which may be the same or different. . As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

The arylene groups represented by Ar ₇ , Ar ₈ and Ar ₉ include the divalent groups of the aryl groups represented by R ₁₁ and R ₁₂ , which may be the same or different. The above-mentioned aryl group and arylene group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. As the alkyl group, preferably,
C ₁ -C _12, especially C ₁ -C ₈ , more preferably C ₁ -C
₄ is a linear or branched alkyl groups, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ ~
A C ₄ alkoxy group, a phenyl group, or a halogen atom,
It may contain a phenyl group substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (—OR ₁₁₃ ). Examples of the alkoxy group (—OR ₁₁₃ ) include those in which R ₁₁₃ is an alkyl group defined in the above (2). Specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) an aryloxy group. As the aryloxy group,
Examples of the aryl group include a phenyl group and a naphthyl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group,
4-methoxyphenoxy group, 4-chlorophenoxy group,
6-methyl-2-naphthyloxy group and the like.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) an alkyl-substituted amino group. Examples of the alkyl-substituted amino group include those in which the alkyl group is the alkyl group defined in the above (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group,
And an N, N-dibenzylamino group. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When the diol compound having a triarylamino group represented by the following general formula (E) is polymerized by a phosgene method, a transesterification method, or the like,
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. The structural part of X is also introduced into the repeating unit by a polymerization reaction between a diol compound having a triarylamino group of the following general formula (E) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0093]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0094]

Embedded image In the formula, R ₁₃ and R ₁₄ are a substituted or unsubstituted aryl group,
Ar ₁₀ , Ar ₁₁ and Ar ₁₂ are the same or different arylene groups,
X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group. X, k, j and n are the same as in the case of the expression (1).

Specific examples of formula (5) R ₁₃ and R ₁₄ represent a substituted or unsubstituted aryl group. Specific examples thereof include the following, which may be the same or different. . As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

The arylene groups represented by Ar ₁₀ , Ar ₁₁ and Ar ₁₂ include the divalent groups of the aryl groups represented by R ₁₃ and R ₁₄ , which may be the same or different.
The above-mentioned aryl group and arylene group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. The alkyl group is preferably a C ₁ -C _12, especially a C ₁ -C ₈ , more preferably a C ₁ -C ₄ linear or branched alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group ,
Cyano group, C ₁ -C ₄ alkoxy group, a phenyl group, or a halogen atom, C ₁ -C alkyl or C ₁ -C ₄ of ₄
May contain a phenyl group substituted with an alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n
-Butyl group, i-butyl group, trifluoromethyl group, 2
-Hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4
-Chlorobenzyl group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like.

(3) An alkoxy group (—OR ₁₁₄ ). Examples of the alkoxy group (—OR ₁₁₄ ) include those in which R ₁₁₄ is an alkyl group defined in the above (2). Specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) Aryloxy group. Examples of the aryloxy group include those having a phenyl group or a naphthyl group as the aryl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group,
Examples thereof include a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, and a 6-methyl-2-naphthyloxy group.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.

(6) Alkyl-substituted amino group. Examples of the alkyl-substituted amino group include those in which the alkyl group is the alkyl group defined in the above (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, N, N -Dibenzylamino group and the like. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

The structural portions of X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group, and the substituent includes a cyano group, a halogen atom, a nitro group, the above R ₁₃ , The aryl group of R _{14 and} the alkyl group of the above (2) are exemplified.

When the diol compound having a triarylamino group of the following general formula (F) is polymerized by a phosgene method, a transesterification method, or the like,
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Further, the structural part of X is introduced into the repeating unit by a polymerization reaction between a diol compound having a triarylamino group of the following general formula (F) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0103]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0104]

Embedded image

In the formula, R ₁₅ , R ₁₆ , R ₁₇ and R ₁₈ are a substituted or unsubstituted aryl group, Ar ₁₃ , Ar ₁₄ , Ar ₁₅ , A
r ₁₆ is the same or different arylene group, Y ₁ , Y ₂ , Y ₃ are a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, It represents a sulfur atom or a vinylene group and may be the same or different. X, k, j
And n are the same as in equation (1).

Specific examples of the formula (6) R ₁₅ , R ₁₆ , R ₁₇ and R ₁₈ represent a substituted or unsubstituted aryl group. Specific examples thereof include the following. Or different.

Examples of the aromatic hydrocarbon group include a phenyl group,
As a condensed polycyclic group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a , D] cycloheptenylidenephenyl group, and a non-fused polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

Ar ₁₃ , Ar ₁₄ , Ar ₁₅ and Ar ₁₆
Examples of the arylene group represented by are the divalent groups of the above aryl groups represented by R ₁₅ , R ₁₆ , R ₁₇ and R ₁₈ , which may be the same or different.

The above aryl group and arylene group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. As the alkyl group, preferably,
C ₁ -C _12, especially C ₁ -C ₈ , more preferably C ₁ -C
₄ is a linear or branched alkyl groups, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ ~
A C ₄ alkoxy group, a phenyl group, or a halogen atom,
It may contain a phenyl group substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (-OR ₁₁₅ ). Examples of the alkoxy group (—OR ₁₁₅ ) include those in which R ₁₁₅ is an alkyl group defined in the above (2), and specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) An aryloxy group. Examples of the aryloxy group include a phenyl group and a naphthyl group as the aryl group. This is a C ₁ -C ₄ alkoxy group, C ₁
It may contain a C ₄ to C ₄ alkyl group or a halogen atom as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be

The structural parts of Y ₁ , Y ₂ and Y ₃ are a single bond,
It represents a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom, and a vinylene group, which may be the same or different.

Examples of the alkylene group include divalent groups derived from the alkyl group shown in the above (2), and specifically, a methylene group, an ethylene group, a 1,3-propylene group, a 1,4 -Butylene group, 2-methyl-1,3-propylene group, difluoromethylene group, hydroxyethylene group, cyanoethylene group, methoxyethylene group, phenylmethylene group, 4-methylphenylmethylene group, 2,2-
Examples thereof include a propylene group, a 2,2-butylene group, and a diphenylmethylene group.

The cycloalkylene group includes 1,1-
Cyclopentylene group, 1,1-cyclohexylene group,
Examples thereof include a 1,1-cyclooctylene group.

Examples of the alkylene ether group include a dimethylene ether group, a diethylene ether group, an ethylene methylene ether group, a bis (triethylene) ether group, and a polytetramethylene ether group.

When the diol compound having a triarylamino group represented by the following general formula (G) is polymerized by a phosgene method, a transesterification method, or the like,
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. The structural part of X is also introduced into the repeating unit by a polymerization reaction between a diol compound having a triarylamino group of the following general formula (G) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0117]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0118]

Embedded image In the formula, R ₁₉ and R ₂₀ represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₉ and R ₂₀ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. X, k, j and n are the same as in the case of the expression (1).

Specific examples of the formula (7) R ₁₉ and R _{20 each} represent a substituted or unsubstituted aryl group. Specific examples thereof include the following, which may be the same or different. .

As the aromatic hydrocarbon group, a phenyl group,
As a condensed polycyclic group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a , D] cycloheptenylidenephenyl group, and a non-fused polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

When R ₁₉ and R ₂₀ form a ring, 9
-Fluorinidene, 5H-dibenzo [a, d] cyclohebutenylidene and the like. Ar ₁₇ , Ar ₁₈
And the arylene group represented by Ar ₁₉ includes R ₁₉ and R ₂₀
And a divalent group of the aryl group represented by the above, and may be the same or different.

The above aryl group and arylene group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. As the alkyl group, preferably,
C ₁ -C _12, especially C ₁ -C ₈ , more preferably C ₁ -C
₄ is a linear or branched alkyl groups, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ ~
A C ₄ alkoxy group, a phenyl group, or a halogen atom,
It may contain a phenyl group substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (—OR ₁₁₆ ). The alkoxy group (-OR _116), include those R _{11 6} are alkyl groups as defined above (2), specifically, methoxy group, an ethoxy radical, n-propoxy group, i-propoxy group, t-butoxy Group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) An aryloxy group. Examples of the aryloxy group include those having a phenyl group or a naphthyl group as the aryl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group,
Examples thereof include a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, and a 6-methyl-2-naphthyloxy group.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) an alkyl-substituted amino group. Examples of the alkyl-substituted amino group include those in which the alkyl group is the alkyl group defined in the above (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group,
And an N, N-dibenzylamino group. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When the diol compound having a triarylamino group represented by the following general formula (H) is polymerized by a phosgene method, a transesterification method or the like, the diol compound represented by the following general formula (B) is used in combination with the diol compound represented by the following general formula (H). Is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer.
The structural part of X is also introduced into the repeating unit by a polymerization reaction between a diol compound having a triarylamino group of the following general formula (H) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0127]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0128]

Embedded image In the formula, R ₂₁ is a substituted or unsubstituted aryl group, A
r ₂₀ , Ar ₂₁ , Ar ₂₂ and Ar ₂₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the expression (1).

Specific examples of formula (8) R ₂₁ represents a substituted or unsubstituted aryl group. Specific examples thereof include the following, which may be the same or different.

As the aromatic hydrocarbon group, a phenyl group,
As a condensed polycyclic group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a , D] cycloheptenylidenephenyl group, and a non-fused polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

Also, Ar ₂₀ , Ar ₂₁ , Ar ₂₂ and Ar ₂₃
Examples of the arylene group represented by are the divalent groups of the aryl group represented by R ₂₁ , which may be the same or different.
The above-mentioned aryl group and arylene group may have the following groups as substituents. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group.

(2) An alkyl group. As the alkyl group,
Preferably, C ₁ -C ₁₂ especially C ₁ -C _8, more preferably a straight-chain or branched-chain alkyl group of C ₁ -C _4,
These alkyl groups may further fluorine atom, a hydroxyl group, a cyano group, an alkoxy group of C ₁ -C _4, substituted with a phenyl group, or a halogen atom, an alkyl group or a C ₁ -C ₄ alkoxy group C ₁ -C ₄ May contain a phenyl group.
Specifically, a methyl group, an ethyl group, an n-propyl group, i
-Propyl group, t-butyl group, s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl, 4-methylbenzyl, 4-methoxybenzyl, 4-phenylbenzyl and the like.

(3) An alkoxy group (—OR ₁₁₇ ). Examples of the alkoxy group (—OR ₁₁₇ ) include those in which R ₁₁₇ is an alkyl group defined in the above (2), and specific examples include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, and a t-butoxy group. , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) An aryloxy group. Examples of the aryloxy group include those having a phenyl group or a naphthyl group as the aryl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group,
Examples thereof include a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, and a 6-methyl-2-naphthyloxy group.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.

(6) Alkyl-substituted amino group. As the alkyl-substituted amino group, an alkyl group represented by the alkyl group defined in the above (2) is used. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When the diol compound having a triarylamino group represented by the following general formula (J) is polymerized by a phosgene method, a transesterification method, or the like, a diol compound represented by the following general formula (B) is used in combination with the diol compound represented by the following general formula (J). Is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer.
Further, this structural part X is composed of a diol compound having a triarylamino group represented by the following general formula (J) and the following general formula (B)
Is also introduced into the repeating unit by a polymerization reaction with bischloroformate derived from In this case, the polycarbonate produced is an alternating copolymer.

[0138]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0139]

Embedded image In the formula, R ₂₂ , R ₂₃ , R ₂₄ , and R ₂₅ are a substituted or unsubstituted aryl group, Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ , Ar ₂₈
Represents the same or different arylene groups. X, k, j and n are the same as in the case of the expression (1).

Specific examples of the formula (9) R ₂₂ , R ₂₃ , R ₂₄ and R ₂₅ represent a substituted or unsubstituted aryl group. Specific examples thereof include the following. Or different.

As the aromatic hydrocarbon group, a phenyl group,
As a condensed polycyclic group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a , D] cycloheptenylidenephenyl group, and a non-fused polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

In addition, Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ ,
And the arylene group represented by Ar ₂₈ includes R ₂₂ ,
The aryl group represented by R ₂₃ , R ₂₄ , and R ₂₅ may be the same or different. The above-mentioned aryl group and arylene group may have the following groups as substituents.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) an alkyl group. As the alkyl group, preferably,
C ₁ -C _12, especially C ₁ -C ₈ , more preferably C ₁ -C
₄ is a linear or branched alkyl groups, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ ~
A C ₄ alkoxy group, a phenyl group, or a halogen atom,
It may contain a phenyl group substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (—OR ₁₁₈ ). Examples of the alkoxy group (—OR ₁₁₈ ) include those in which R ₁₁₈ is an alkyl group defined in the above (2). Specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) An aryloxy group. Examples of the aryloxy group include those having a phenyl group or a naphthyl group as the aryl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group,
Examples thereof include a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, and a 6-methyl-2-naphthyloxy group.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.

(6) An alkyl-substituted amino group. Examples of the alkyl-substituted amino group include those in which the alkyl group is the alkyl group defined in the above (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, N, N -Dibenzylamino group and the like. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When the diol compound having a triarylamino group represented by the following general formula (L) is polymerized by a phosgene method, a transesterification method, or the like,
It is introduced into the main chain by using a diol compound of the following general formula (B) in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. The structural part X is also introduced into the repeating unit by a polymerization reaction between a diol compound having a triarylamino group represented by the following general formula (L) and a bischloroformate derived from the following general formula (B). . In this case, the polycarbonate produced is an alternating copolymer.

[0149]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

[0150]

Embedded image In the formula, R ₂₆ and R ₂₇ are a substituted or unsubstituted aryl group,
Ar ₂₉ , Ar ₃₀ and Ar ₃₁ represent the same or different arylene groups. X, k, j and n are the same as in the case of the expression (1).

Specific examples of formula (10) R ₂₆ and R _{27 each} represent a substituted or unsubstituted aryl group. Specific examples thereof include the following, which may be the same or different. .

As the aromatic hydrocarbon group, a phenyl group,
As a condensed polycyclic group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a , D] cycloheptenylidenephenyl group, and a non-fused polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group, and a carbazolyl group.

The arylene groups represented by Ar ₂₉ , Ar ₃₀ and Ar ₃₁ include the divalent groups of the aryl groups represented by R ₂₆ and R ₂₇ , which may be the same or different. The above-mentioned aryl group and arylene group may have the following groups as substituents.

(1) A halogen atom, a trifluoromethyl group, a cyano group, and a nitro group. (2) an alkyl group. As the alkyl group, preferably,
C ₁ -C _12, especially C ₁ -C ₈ , more preferably C ₁ -C
₄ is a linear or branched alkyl groups, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ ~
A C ₄ alkoxy group, a phenyl group, or a halogen atom,
It may contain a phenyl group substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, t-butyl, s-butyl, n-butyl, i-butyl
-Butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group,
Examples include a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group.

(3) An alkoxy group (—OR ₁₁₉ ). Examples of the alkoxy group (—OR ₁₁₉ ) include those in which R ₁₁₉ is an alkyl group defined in the above (2), and specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, a t-butoxy group , N-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like.

(4) An aryloxy group. Examples of the aryloxy group include those having a phenyl group or a naphthyl group as the aryl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group,
Examples thereof include a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, and a 6-methyl-2-naphthyloxy group.

(5) Substituted mercapto group or arylmercapto group. Specific examples of the substituted mercapto group or arylmercapto group include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) an alkyl-substituted amino group. Examples of the alkyl-substituted amino group include those in which the alkyl group is the alkyl group defined in the above (2). Specifically, a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group,
And an N, N-dibenzylamino group. (7) an acyl group. Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When the diol compound having a triarylamino group represented by the following general formula (M) is polymerized by a phosgene method, a transesterification method or the like, the diol compound represented by the following general formula (B) is used in combination with the diol compound represented by the following general formula (B). Is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer.
Further, this structural part X is composed of a diol compound having a triarylamino group represented by the following general formula (M) and a general formula (B)
Is also introduced into the repeating unit by a polymerization reaction with bischloroformate derived from In this case, the polycarbonate produced is an alternating copolymer.

[0159]

Embedded image As the diol compound of the general formula (B), the same diol compounds as in the formula (1) can be mentioned.

X in the formulas (1) to (10) (general formula B
In the formula, X) preferably has the following structure.

[0161]

Embedded image In the formula, when R ₃₀₁ and R ₃₀₂ are each independently, a hydrogen atom, an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc. (Including a substituted alkyl group such as trifluoromethyl), an aryl group such as phenyl and naphthyl (including a substituted aryl group having a substituent such as halogen and an alkyl group having 1 to 5 carbon atoms), When R ₃₀₁ and R ₃₀₂ are bonded to each other, they represent a group of carbon atoms necessary to form a cyclic hydrocarbon group containing cycloalkanes such as hexyl and polycycloalkanes such as norbornyl. R ₃₀₃ and R ₃₀₄ each represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogen atom such as chlorine, bromine or iodine.

To form the eutectic complex photosensitive layer (31), the above-mentioned pyrylium-based dye and a polycarbonate containing a triarylamine structure in the main chain and / or the side chain are suitably used in a suitable solvent such as tetrahydrofuran, toluene, 1,2- It is dissolved in dichloroethane, methylene chloride, chloroform, monochlorobenzene, dichlorobenzene, benzene, etc., applied on a conductive support (11) and dried to form a film having a thickness of 5 to 5 μm.
What is necessary is just to form a photoconductive layer (eutectic complex photosensitive layer) of 0 μm. The coating can be performed by a dip coating method, a bead coating method, a spray coating method, a wire blade, a doctor blade, an air knife, or the like. During this coating and drying, a eutectic complex is formed between the pyrylium-based dye and a polycarbonate containing a triarylamine structure in the main chain and / or side chain. The proportion of each component in the eutectic complex photosensitive layer (31) is suitably from 5 to 100 parts by weight of the polymer charge transport substance per 1 part by weight of the pyrylium-based dye.

The eutectic complex photosensitive layer (31) may optionally contain an appropriate binder resin and a low-molecular charge transport material. The low-molecular charge transporting material that can be used in combination with the eutectic complex photosensitive layer (31) includes a hole transporting material and an electron transporting material.

Examples of the electron transporting substance include chloranil, bromanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,
4,8-trinitrothioxanthone, 2,6,8-trinitro-4H-indeno [1,2-b] thiophene-4
ON, 1,3,7-trinitrodibenzothiophene-
Electron accepting substances such as 5,5-dioxide are exemplified. These electron transport materials can be used alone or as a mixture of two or more.

As the hole transporting substance, the following electron donating substances can be used, and are preferably used. For example, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, triphenylamine derivatives, 9-
(P-diethylaminostyrylanthracene), 1,1
-Bis- (4-dibenzylaminophenyl) propane,
Styryl anthracene, styryl pyrazoline, phenylhydrazone, α-phenylstilbene derivative, thiazole derivative, triazole derivative, phenazine derivative,
Examples include acridine derivatives, benzofuran derivatives, benzimidazole derivatives, and thiophene derivatives. These hole transporting substances can be used alone or as a mixture of two or more kinds.

Among them, low molecular charge transporting substances represented by the following formulas (11) to (21) are preferable.

[0167]

Embedded image In the formula, R ₂₀₁ , R ₂₀₂ , R ₂₀₃ and R ₂₀₄ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted aryl group, and Ar ₁₀₁ represents a substituted or unsubstituted aryl group, Ar ₁₀₂ represents a substituted or unsubstituted arylene group, Ar ₁₀₁ and R ₂₀₁ may jointly form a ring, and n ₁ is an integer of 0 or 1.

[0168]

Embedded image In the formula, R ₂₀₅ represents a lower alkyl group, a lower alkoxy group or a halogen atom, n ₂ represents an integer of 0 to 4,
R ₂₀₆ and R ₂₀₇ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom.

[0169]

Embedded image In the formula, R ₂₀₈ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group or a heterocyclic group;
₂₀₉ and R ₂₁₀ may be the same or different and include a hydrogen atom,
Lower alkyl group, a hydroxyalkyl group C ₁ -C _4, C
₁ -C ₄ a chloroalkyl group, or a substituted or unsubstituted aralkyl group, also, R ₂₀₉ and R ₂₁₀ may form a heterocyclic ring containing a nitrogen jointly, R _211, R ₂₁₂ are each the same And may be different, and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom.

[0170]

Embedded image In the formula, R ₂₁₃ represents a hydrogen atom or a halogen atom;
₂₁₄ is a substituted or unsubstituted aromatic residue or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, Selected from the group consisting of an alkoxy group and a nitro group).

[0171]

Embedded image In the formula, R ₂₁₅ , R ₂₁₆ and R ₂₁₇ each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a heterocyclic group, and at least two of R ₂₁₅ , R ₂₁₆ and R ₂₁₇ are aryl. Represents a group or a heterocyclic group.

[0172]

Embedded image In the formula, Ar ₁₀₃ and Ar ₁₀₄ each represent a substituted or unsubstituted aryl group or a heteroaromatic ring.

[0173]

Embedded image In the formula, Ar ₁₀₅ represents a substituted or unsubstituted aryl group or a heteroaromatic ring, and R ₂₁₈ and R ₂₁₉ are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a heterocyclic group, respectively. _At least one of ₂₁₈ and R ₂₁₉ comprises an aryl group or a heterocyclic group.

[0174]

Embedded image In the formula, R ₂₂₀ and R ₂₂₂ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group,
R ₂₂₁ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group, and n ₃ represents an integer of 0 or 1.

[0175]

Embedded image In the formula, R ₂₂₃ represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, or a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group (provided that the substituent is a di-lower alkyl group). Amino group, lower alkyl group, lower alkoxy group, halogen atom, aralkylamino group or amino group).

[0176]

Embedded image In the formula, Ar ₁₀₆ represents a substituted or unsubstituted biphenylene group, and R ₂₂₄ , R ₂₂₅ and R _{226 each} represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group, an alkoxy group which may have a substituent, Aryloxy group, alkyl mercapto group, methylenedioxy group, methylenedithio group,
Represents an aryl group, and R ₂₂₄ , R ₂₂₅ and R ₂₂₆ may be the same or different. U, v, and w each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₂₂₄ , R ₂₂₅ and R ₂₂₆ may be the same or different.

[0177]

Embedded image Wherein, R ₂₂₇ and R ₂₂₈ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R ₂₂₇
And at least one of R ₂₂₈ represents a substituted or unsubstituted aryl group. If the amount of the low-molecular charge transporting substance is too large, the abrasion of the film becomes large.

Examples of the binder resin usable in combination with the eutectic complex photosensitive layer (31) include polycarbonate (bisphenol A type, bisphenol Z type), polyester, methacrylic resin, acrylic resin, polyethylene, vinyl chloride, vinyl acetate, polystyrene, and phenol resin. , Epoxy resin, polyurethane, polyvinylidene chloride, alkyd resin, silicon resin, polyvinyl carbazole, polyvinyl butyral, polyvinyl formal, polyacrylate, polyacrylamide, phenoxy resin and the like. These binders can be used alone or as a mixture of two or more.

In the present invention, the eutectic complex photosensitive layer (3
A plasticizer or a leveling agent may be added during 1). As the plasticizer, those used as plasticizers for general resins such as dibutyl phthalate and dioctyl phthalate can be used as they are, and the amount used is 0 to 30 parts by weight based on 100 parts by weight of the polymer charge transporting substance. The degree is appropriate. As the leveling agent, silicone oils such as dimethyl silicone oil and methyl phenyl silicone oil, and polymers or oligomers having a perfluoroalkyl group in a side chain are used. About 1 part by weight is appropriate.

The electrophotographic photosensitive member used in the present invention includes:
An undercoat layer (25) can be provided between the conductive support (21) and the eutectic complex photosensitive layer (31). The undercoat layer (25) is provided for the purpose of improving adhesiveness, preventing moiré, etc., improving coatability of the upper layer, reducing residual potential, and the like. The undercoating layer (25) generally contains a resin as a main component. However, considering that a photosensitive layer is coated thereon with a solvent, these resins are resins having high resistance to dissolution in general organic solvents. Desirably. Such resins include polyvinyl alcohol, casein,
Water-soluble resins such as sodium polyacrylate, alcohol-soluble resins such as copolymerized nylon and methoxymethylated nylon, polyurethanes, melamine resins, alkyd-melamine resins, epoxy resins, and other curing resins that form a three-dimensional network structure. No. Further, a fine powder of a metal oxide such as titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide, or a metal sulfide or a metal nitride may be added. These undercoat layers are made of a suitable solvent,
It can be formed using a coating method.

Further, as the undercoat layer of the present invention, a metal oxide layer formed by, for example, a sol-gel method using a silane coupling agent, a titanium coupling agent, a chromium coupling agent or the like is also useful. . In addition, the undercoat layer of the present invention is provided with Al ₂ O ₃ by anodic oxidation, an organic substance such as polyparaxylene (parylene), SiO, S
Those provided with an inorganic substance such as nO ₂ , TiO ₂ , ITO, CeO ₂ by a vacuum thin film manufacturing method can also be used favorably. The thickness of the undercoat layer is suitably from 0 to 5 μm. Further, the eutectic complex photosensitive layer (31) in the present invention may be used as a charge generation layer, and a charge transport layer (33) may be laminated to form a laminated photoconductor.

Next, the charge transport layer (33) will be described. The charge transport layer (33) can be formed by dissolving or dispersing a charge transport material and a binder resin in a suitable solvent, and applying and drying this. If necessary, a plasticizer or a leveling agent can be added. As the charge transport material, the above-described hole transport material and electron transport material can be used. As the binder resin that can be used in combination with the charge transport layer (33), polycarbonate (bisphenol A)
Type, bisphenol Z type), polyester, methacrylic resin, acrylic resin, polyethylene, vinyl chloride, vinyl acetate, polystyrene, phenolic resin, epoxy resin, polyurethane, polyvinylidene chloride, alkyd resin, silicone resin, polyvinyl carbazole, polyvinyl butyral, polyvinyl Formal, polyacrylate, polyacrylamide, phenoxy resin and the like are used. Among them, the above (2) to
The polycarbonate having the structure of the formula (4) is effectively used. These binders can be used alone or as a mixture of two or more.

Further, a polymer charge transporting substance having both functions of a binder resin and a charge transporting substance can be used as the binder resin. Examples of the polymer charge transport material used in this case include the following. (A) Polymer having carbazole ring in main chain and / or side chain For example, poly-N-vinylcarbazole,
Compounds described in JP-A-82056, JP-A-54-9632, JP-A-54-11737 and JP-A-4-183719 are exemplified. (B) Polymer having a hydrazone structure in the main chain and / or side chain. For example, JP-A-57-78402, JP-A-3-5-5
Compounds described in JP-A No. 0555/1999 and the like are exemplified. (C) Polysilylene polymer For example, JP-A-63-285552,
Compounds described in, for example, JP-A No. 19497 and JP-A-5-70595 are exemplified. (D) Polymer having a tertiary amine structure in the main chain and / or side chain, for example, N, N-bis (4-methylphenyl) -4-aminopolystyrene, JP-A-1-13061, JP-A-1-13061 -19049, JP-A 1-1728,
JP-A-1-105260, JP-A-2-16733
No. 5, JP-A-5-66598, JP-A-5-4
Compounds described in JP-A-03350 are exemplified. (E) Other polymers For example, a formaldehyde condensation polymer of nitropyrene, JP-A-51-73888, JP-A-56-15074
Compounds described in, for example, Japanese Patent Application Publication No. 9-No. 9 are exemplified. The polymer charge transporting material used in the present invention includes not only the above-mentioned polymers but also copolymers of known monomers, block polymers, graft polymers, star polymers, and, for example, JP-A-3-109406. It is also possible to use a crosslinked polymer or the like having an electron donating group as disclosed in Japanese Patent Application Laid-Open Publication No. H11-163,036. Furthermore, the polymer charge transport materials of the formulas (1) to (10) described in the present invention can of course be used favorably. The film thickness of the charge transport layer (33) is suitably about 5 to 100 μm. In the present invention, a plasticizer and a leveling agent may be added to the charge transport layer (33). As the plasticizer and the leveling agent, those described above can be used as they are.
The amount used is the same as described above.

Further, in the present invention, an antioxidant can be added for the purpose of improving environmental resistance, especially for the purpose of preventing a decrease in sensitivity and an increase in residual potential. The antioxidants that can be used in the present invention include the following.

Monophenolic compounds 2,6-di-tert-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-tert-butyl-4-ethylphenol, stearyl-β- (3,5- Di-t-
(Butyl-4-hydroxyphenyl) propionate and the like.

Bisphenolic compounds 2,2'-methylene-bis- (4-methyl-6-t-butylphenol), 2,2'-methylene-bis- (4-
Ethyl-6-t-butylphenol), 4,4′-thiobis- (3-methyl-6-t-butylphenol),
4,4'-butylidenebis- (3-methyl-6-t-butylphenol) and the like.

High molecular phenolic compound 1,1,3-tris- (2-methyl-4-hydroxy-
5-t-butylphenyl) butane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-
4-hydroxybenzyl) benzene, tetrakis- [methylene-3- (3 ′, 5′-di-tert-butyl-4′-hydroxyphenyl) propionate] methane, bis [3,3′-bis (4′-hydroxy -3'-t-butylphenyl) butyric acid] glycol esters, tocophenols and the like.

Paraphenylenediamines N-phenyl-N'-isopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N-phenyl-N-sec-butyl-p-
Phenylenediamine, N, N'-di-isopropyl-p
-Phenylenediamine, N, N'-dimethyl-N, N '
-Di-tert-butyl-p-phenylenediamine and the like.

Hydroquinones 2,5-di-t-octylhydroquinone, 2,6-didodecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5-chlorohydroquinone, 2-t
-Octyl-5-methylhydroquinone, 2- (2-octadecenyl) -5-methylhydroquinone and the like.

Organic sulfur compounds: dilauryl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, ditetradecyl-3,3'-thiodipropionate and the like.

Organic phosphorus compounds Triphenylphosphine, tri (nonylphenyl) phosphine, tri (dinonylphenyl) phosphine, tricresylphosphine, tri (2,4-dibutylphenoxy) phosphine and the like.

These compounds are known as antioxidants for rubber, plastics, oils and the like, and can be easily obtained as commercial products. The addition amount of the antioxidant in the present invention is 0.1 to 10 parts by weight based on 100 parts by weight of the charge transport material.
0 parts by weight, preferably 2 to 30 parts by weight.

As an application example of the present invention, a composite photoconductor for electrophotography as shown in FIG. For the second photosensitive layer (35), a known material (for example, JP-A-56-12) is used.
No. 1044), and the above-mentioned eutectic complex photosensitive layer (31) can be used as the first photosensitive layer. An image can be formed by applying a known process (for example, JP-A-56-121044) to the composite photoreceptor for electrophotography thus formed.

[0194]

Next, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples. All parts used in the examples are parts by weight. Example 1 A coating liquid for a eutectic complex photosensitive layer having the following composition was applied on an aluminum-deposited polyethylene terephthalate film and dried to form a eutectic complex photosensitive layer having a thickness of about 20 μm. Was prepared. (Coating solution for eutectic complex photosensitive layer) 24 parts of methylene chloride 16 parts of chloroform 0.2 part of a pyrylium dye having the following structure

[0195]

Embedded image 4 parts of polymer charge transport material having the following structure

[0196]

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Example 2 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0198]

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Example 3 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0200]

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Example 4 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0202]

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Example 5 A photoconductor was prepared in the same manner as in Example 1 except that one part of a low-molecular charge transporting material having the following structure was added to the coating solution for the eutectic complex photosensitive layer of Example 1.

[0204]

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Example 6 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0206]

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Example 7 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0208]

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Example 8 A photoconductor was prepared in the same manner as in Example 1, except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0210]

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Example 9 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0212]

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Example 11 A photoconductor was prepared in the same manner as that of Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0214]

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Example 12 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0216]

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Example 13 A photoconductor was prepared in the same manner as in Example 1 except that 1 part of a low-molecular charge transporting material having the following structure was added to the eutectic complex photosensitive layer coating solution of Example 1.

[0218]

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Example 14 A photoconductor was prepared in the same manner as in Example 13 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the eutectic complex photosensitive layer coating liquid of Example 13. did. Example 15 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transport material used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 13. Example 16 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transport material used in Example 4 was added to the eutectic complex photosensitive layer coating liquid of Example 13. Example 17 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transporting material used in Example 5 was added to the eutectic complex photosensitive layer coating solution of Example 13. Example 18 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transporting material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 13. Example 19 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transporting material used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 13. Example 20 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 13. Example 21 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 13. Example 22 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 13. Example 23 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transport material used in Example 11 was added to the eutectic complex photosensitive layer coating solution of Example 13. Example 24 A photoconductor was prepared in the same manner as that of Example 13 except that one part of the low-molecular charge transporting material used in Example 12 was added to the coating solution for the eutectic complex photosensitive layer of Example 13.

Example 25 Example 1 was repeated except that the polymer charge transporting material of the eutectic complex photosensitive layer coating liquid in Example 1 was changed to one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0221]

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Example 26 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. did. Example 27 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transporting substance used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 28 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 4 was added to the eutectic complex photosensitive layer coating solution of Example 25. Example 29 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 5 was added to the eutectic complex photosensitive layer coating solution of Example 25. Example 30 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 31 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular-weight charge transport material used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 32 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 33 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 34 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 35 A photoconductor was prepared by the same way as that of Example 25 except that one part of the low-molecular charge transport material used in Example 11 was added to the coating solution for the eutectic complex photosensitive layer of Example 25. Example 36 A photoconductor was prepared in the same manner as that of Example 25 except that one part of the low-molecular charge transport material used in Example 12 was added to the coating solution for the eutectic complex photosensitive layer of Example 25.

Example 37 Example 1 was repeated except that the polymer charge transporting material in the coating liquid for the eutectic complex photosensitive layer in Example 1 was changed to one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0224]

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Example 38 A photoconductor was prepared in the same manner as that of Example 37 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. did. Example 39 A photoconductor was prepared by the same way as that of Example 37 except that one part of the low-molecular charge transport material used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 40 A photoconductor was prepared by the same way as that of Example 37 except that one part of the low-molecular charge transport material used in Example 4 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 41 A photoconductor was prepared in the same manner as that of Example 37 except that one part of the low-molecular charge transport material used in Example 5 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 42 A photoconductor was prepared in the same manner as that of Example 37 except that one part of the low-molecular charge transport material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 43 A photoconductor was prepared by the same way as that of Example 37 except that one part of the low-molecular charge transport material used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 44 A photoconductor was prepared by the same way as that of Example 37 except that one part of the low-molecular charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 45 A photoconductor was prepared by the same way as that of Example 37 except that one part of the low-molecular-weight charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 46 A photoconductor was prepared in the same manner as that of Example 37 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 47 A photoconductor was prepared by the same way as that of Example 37 except that one part of the low-molecular charge transport material used in Example 11 was added to the coating solution for the eutectic complex photosensitive layer of Example 37. Example 48 A photoconductor was prepared in the same manner as that of Example 37 except that one part of the low-molecular-weight charge transporting substance used in Example 12 was added to the coating solution for the eutectic complex photosensitive layer of Example 37.

Example 49 Example 1 was repeated except that the polymer charge transporting substance of the coating solution for the eutectic complex photosensitive layer in Example 1 was changed to the one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0227]

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Example 50 A photoconductor was prepared in the same manner as that of Example 49 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. did. Example 51 A photoconductor was prepared in the same manner as that of Example 49 except that one part of the low-molecular charge transporting substance used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 52 A photoconductor was prepared in the same manner as that of Example 49 except that one part of the low-molecular-weight charge transporting substance used in Example 4 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 53 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular-weight charge transporting substance used in Example 5 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 54 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular charge transport material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 55 A photoconductor was prepared in the same manner as that of Example 49 except that one part of the low-molecular charge transport material used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 56 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 57 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 58 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 59 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular charge transport material used in Example 11 was added to the coating solution for the eutectic complex photosensitive layer of Example 49. Example 60 A photoconductor was prepared by the same way as that of Example 49 except that one part of the low-molecular-weight charge transporting substance used in Example 12 was added to the eutectic complex photosensitive layer coating solution of Example 49.

Example 61 Example 1 was repeated except that the polymer charge transporting material in the coating solution for the eutectic complex photosensitive layer in Example 1 was changed to one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0230]

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Example 62 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. did. Example 63 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular-weight charge transport material used in Example 3 was added to the eutectic complex photosensitive layer coating solution of Example 61. Example 64 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 4 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. Example 65 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 5 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. Example 66 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 6 was added to the eutectic complex photosensitive layer coating solution of Example 61. Example 67 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. Example 68 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular-weight charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. Example 69 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. Example 70 A photoconductor was prepared by the same way as that of Example 61 except that one part of the low-molecular-weight charge transporting substance used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 61. Example 71 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular charge transport material used in Example 11 was added to the eutectic complex photosensitive layer coating solution of Example 61. Example 72 A photoconductor was prepared in the same manner as that of Example 61 except that one part of the low-molecular-weight charge transport material used in Example 12 was added to the eutectic complex photosensitive layer coating solution of Example 61.

Example 73 Example 1 was repeated except that the polymer charge transporting material in the coating liquid for the eutectic complex photosensitive layer in Example 1 was changed to one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0233]

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Example 74 A photoconductor was prepared in the same manner as that of Example 73 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. did. Example 75 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular-weight charge transporting substance used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 76 A photoconductor was prepared in the same manner as that of Example 73 except that one part of the low-molecular charge transport material used in Example 4 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 77 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular-weight charge transporting substance used in Example 5 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 78 A photoconductor was prepared in the same manner as that of Example 73 except that one part of the low-molecular charge transport material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 79 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular-weight charge transporting substance used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 80 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 81 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 73. Example 82 A photoconductor was prepared in the same manner as that of Example 73 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating liquid for the eutectic complex photosensitive layer of Example 73. Example 83 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular charge transporting substance used in Example 11 was added to the coating liquid for the eutectic complex photosensitive layer of Example 73. Example 84 A photoconductor was prepared by the same way as that of Example 73 except that one part of the low-molecular-weight charge transport material used in Example 12 was added to the eutectic complex photosensitive layer coating solution of Example 73.

Example 85 Example 1 was repeated except that the polymer charge transporting material in the coating liquid for the eutectic complex photosensitive layer in Example 1 was changed to one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0236]

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Example 86 A photoconductor was prepared in the same manner as that of Example 85 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. did. Example 87 A photoconductor was prepared by the same way as that of Example 85 except that one part of the low-molecular charge transport material used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 88 A photoconductor was prepared by the same way as that of Example 85 except that one part of the low-molecular charge transporting material used in Example 4 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 89 A photoconductor was prepared by the same way as that of Example 85 except that one part of the low-molecular-weight charge transport material used in Example 5 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 90 A photoconductor was prepared in the same manner as that of Example 85 except that one part of the low-molecular charge transport material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 91 A photoconductor was prepared in the same manner as that of Example 85 except that one part of the low-molecular charge transporting substance used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 92 A photoconductor was prepared in the same manner as that of Example 85 except that one part of the low-molecular charge transport material used in Example 8 was added to the eutectic complex photosensitive layer coating liquid of Example 85. Example 93 A photoconductor was prepared by the same way as that of Example 85 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 94 A photoconductor was prepared in the same manner as that of Example 85 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 95 A photoconductor was prepared by the same way as that of Example 85 except that one part of the low-molecular charge transport material used in Example 11 was added to the coating solution for the eutectic complex photosensitive layer of Example 85. Example 96 A photoconductor was prepared by the same way as that of Example 85 except that one part of the low-molecular-weight charge transporting substance used in Example 12 was added to the coating solution for the eutectic complex photosensitive layer of Example 85.

Example 97 Example 97 was repeated except that the polymer charge transporting material in the coating solution for the eutectic complex photosensitive layer in Example 1 was changed to the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0239]

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Example 98 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 97. did. Example 99 A photoconductor was prepared by the same way as that of Example 97 except that one part of the low-molecular charge transport material used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 97. Example 100 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular-weight charge transporting substance used in Example 4 was added to the coating solution for the eutectic complex photosensitive layer of Example 97. Example 101 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transport material used in Example 5 was added to the eutectic complex photosensitive layer coating liquid of Example 97. Example 102 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transport material used in Example 6 was added to the eutectic complex photosensitive layer coating solution of Example 97. Example 103 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transport material used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 97. Example 104 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular-weight charge transporting substance used in Example 8 was added to the eutectic complex photosensitive layer coating liquid of Example 97. Example 105 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transporting substance used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 97. Example 106 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transport material used in Example 10 was added to the eutectic complex photosensitive layer coating liquid of Example 97. Example 107 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular charge transport material used in Example 11 was added to the coating solution for the eutectic complex photosensitive layer of Example 97. Example 108 A photoconductor was prepared in the same manner as that of Example 97 except that one part of the low-molecular-weight charge transporting substance used in Example 12 was added to the coating solution for the eutectic complex photosensitive layer of Example 97.

Example 109 Example 1 was repeated except that the polymer charge transporting material in the coating solution for the eutectic complex photosensitive layer in Example 1 was changed to one having the following structure.
A photoreceptor was produced in exactly the same manner as described above.

[0242]

Embedded image

Example 110 A photoconductor was prepared in the same manner as that of Example 109 except that one part of the low-molecular charge transporting substance used in Example 2 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. did. Example 111 A photoconductor was prepared by the same way as that of Example 109 except that one part of the low-molecular charge transport material used in Example 3 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 112 A photoconductor was prepared in the same manner as that of Example 109 except that one part of the low-molecular charge transporting substance used in Example 4 was added to the eutectic complex photosensitive layer coating solution of Example 109. Example 113 A photoconductor was prepared in the same manner as that of Example 109 except that one part of the low-molecular charge transporting material used in Example 5 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 114 A photoconductor was prepared by the same way as that of Example 109 except that one part of the low-molecular charge transport material used in Example 6 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 115 A photoconductor was prepared in the same manner as that of Example 109 except that one part of the low-molecular charge transporting substance used in Example 7 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 116 A photoconductor was prepared by the same way as that of Example 109 except that one part of the low-molecular-weight charge transport material used in Example 8 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 117 A photoconductor was prepared in the same manner as that of Example 109 except that one part of the low-molecular charge transport material used in Example 9 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 118 A photoconductor was prepared by the same way as that of Example 109 except that one part of the low-molecular charge transport material used in Example 10 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 119 A photoconductor was prepared in the same manner as that of Example 109 except that one part of the low-molecular charge transporting substance used in Example 11 was added to the coating solution for the eutectic complex photosensitive layer of Example 109. Example 120 A photoconductor was prepared by the same way as that of Example 109 except that one part of the low-molecular charge transporting substance used in Example 12 was added to the coating solution for the eutectic complex photosensitive layer of Example 109.

Comparative Example 1 A photoconductor was prepared in the same manner as in Example 1 except that the coating solution for the eutectic complex photosensitive layer in Example 1 was changed to the one having the following composition.

Polycarbonate (Teijin: Panlite C1400) 2.1 parts 24 parts of methylene chloride 16 parts of chloroform 0.2 parts of a pyrylium-based dye having the following structure

[0246]

Embedded image 1.9 parts of a low molecular charge transport material having the following structure

[0247]

Embedded image

Comparative Example 2 A photoconductor was prepared in the same manner as in Example 1, except that the coating solution for the eutectic complex photosensitive layer in Example 1 was changed to the one having the following composition.

Polycarbonate (Mitsubishi Gas Chemical: Iupilon Z-200) 2.1 parts Methylene chloride 24 parts Chloroform 16 parts A pyrylium-based dye having the following structure 0.2 parts

[0250]

Embedded image 1.9 parts of a low molecular charge transport material having the following structure

[0251]

Embedded image

The electrophotographic photoreceptors of Examples 1-120 and Comparative Examples 1 and 2 produced as described above were evaluated for photoreceptor characteristics using an electrostatic copying paper test apparatus (Kawaguchi Electric: EPA SP-428). . First, the photoreceptor is charged at a charging voltage of 6.0 kV until the surface potential of the photoreceptor becomes 800 V, irradiated with tungsten light (61 ux), and the exposure amount (E _1/2 ) required to attenuate to 400 V is measured. did. Table 2 shows the results.

[0253]

[Table 2-1]

[0254]

[Table 2-2]

[0255]

[Table 2-3]

[0256]

[Table 2-4]

[0257]

[Table 2-5]

[0258]

[Table 2-6]

Example 121 On the same support as in Example 1, a coating liquid for an undercoat layer having the following composition and a coating liquid for a eutectic complex photosensitive layer having the same composition as in Example 1 were successively applied and dried to about 0 An electrophotographic photosensitive member of the present invention was prepared by forming a 0.3 μm undercoat layer and a eutectic complex photosensitive layer of about 20 μm. Alcohol-soluble nylon (Toray: CM-8000) 3 parts Methanol 70 parts Butanol 30 parts

Example 122 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 13.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 123 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 25.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 124 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 37.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 125 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 49.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 126 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 61.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 127 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 73.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 128 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 85.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 129 Example 12 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Example 97.
An electrophotographic photosensitive member was produced in exactly the same manner as in Example 1. Example 130 The coating solution for the eutectic complex photosensitive layer of Example 121 was prepared in Example 109.
Example 1 except that the coating liquid for the eutectic complex photosensitive layer was changed to
An electrophotographic photoreceptor was produced in exactly the same manner as in No. 21.

Comparative Example 3 Example 121 was repeated except that the coating solution for the eutectic complex photosensitive layer in Example 121 was changed to the coating solution for the eutectic complex photosensitive layer in Comparative Example 1.
An electrophotographic photoreceptor was produced in exactly the same manner as described above. Comparative Example 4 Example 121 was repeated except that the coating solution for the eutectic complex photosensitive layer of Example 121 was changed to the coating solution for the eutectic complex photosensitive layer of Comparative Example 2.
An electrophotographic photoreceptor was produced in exactly the same manner as in

Examples 121 to 13 produced as described above
The electrophotographic photoreceptors of Comparative Example Nos. 0 and Comparative Examples 3 and 4 used an abrasion tester (Toyo Seiki Co., Ltd.) to perform 1500 rotations with a wear wheel CS-10 (load 250
The wear amount according to g) was evaluated. Table 3 shows the results.

[0263]

[Table 3]

[0264]

As described above in detail and specifically, the electrophotographic photoreceptor of the present invention has a high sensitivity, a high mechanical durability (abrasion resistance) when used repeatedly, and a high repetition rate. In use, a stable image can be obtained.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view illustrating a configuration example of an electrophotographic photosensitive member of the present invention.

FIG. 2 is a cross-sectional view showing another example of the configuration of the electrophotographic photosensitive member of the present invention.

FIG. 3 is a cross-sectional view showing still another configuration example of the electrophotographic photosensitive member of the present invention.

FIG. 4 is a cross-sectional view of a composite photoconductor for electrophotography as an application of the present invention.

[Explanation of symbols]

 Reference Signs List 21 conductive support 25 undercoat layer 31 eutectic complex photosensitive layer 33 charge transport layer 35 second photosensitive layer

────────────────────────────────────────────────── ─── front page continued (51) Int.Cl. ⁶ identifications FI C08L 69/00 C08L 69/00 G03G 5/06 312 G03G 5/06 312 313 313 314 314B 316 316A 322 322 5/09 103 5 / 09 103

Claims (23)

[Claims] 1. A photoconductive layer including a eutectic complex containing a pyrylium dye and a polycarbonate containing a triarylamine structure in a main chain and / or a side chain as a main component is provided on a conductive support. An electrophotographic photosensitive member characterized by the following. 2. A photoconductive layer comprising a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (1) as a main component is provided on a conductive support. Electrophotographic photoreceptor. Embedded image In the formula, R ₁ , R ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group or a halogen atom, R ₄ is a hydrogen atom or a substituted or unsubstituted alkyl group, and R ₅ and R ₆ are substituted or unsubstituted. A substituted aryl group, o, p, and q each independently represent an integer of 0 to 4, k and j each represent a composition, and 0.1 ≦
k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units and is an integer of 5 to 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula. Embedded image In the formula, R ₁₀₁ and R ₁₀₂ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom.
l and m are integers from 0 to 4, Y is a single bond, and has 1 to 1 carbon atoms.
2 linear, branched or cyclic alkylene groups, -O
-, - S -, - SO -, - SO 2 -, - CO -, - CO
—O—Z—O—CO— (wherein Z represents an aliphatic divalent group) or (In the formula, a represents an integer of 1 to 20, b represents an integer of 1 to 2,000, and R ₁₀₃ and R ₁₀₄ represent a substituted or unsubstituted alkyl group or aryl group.) Here, R ₁₀₁ and R ₁₀₂ and R ₁₀₃ and R ₁₀₄ may be the same or different. 3. A photoconductive layer comprising a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (2) as a main component is provided on a conductive support. Electrophotographic photoreceptor. Embedded image In the formula, R ₇ and R ₈ represent a substituted or unsubstituted aryl group, A
r ₁ , Ar ₂ and Ar ₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). 4. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (3) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₉ and R ₁₀ are a substituted or unsubstituted aryl group,
Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). 5. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (4) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₁₁ and R ₁₂ are a substituted or unsubstituted aryl group,
Ar ₇ , Ar ₈ and Ar ₉ are the same or different arylene groups, p
Represents an integer of 1 to 5. X, k, j and n are the same as in the case of the above equation (1). 6. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (5) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₁₃ and R ₁₄ are a substituted or unsubstituted aryl group,
Ar ₁₀ , Ar ₁₁ and Ar ₁₂ are the same or different arylene groups,
X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group. X, k, j and n are the same as in the case of the above equation (1). 7. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (6) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₁₅ , R ₁₆ , R ₁₇ and R ₁₈ are a substituted or unsubstituted aryl group, Ar ₁₃ , Ar ₁₄ , Ar ₁₅ and Ar ₁₆ are the same or different arylene groups, Y ₁ , Y ₂ and Y ₃ are A single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom, and a vinylene group may be the same or different. X, k, j and n are the same as in the case of the above equation (1). 8. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (7) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₁₉ and R ₂₀ represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₉ and R ₂₀ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). 9. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (8) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₂₁ is a substituted or unsubstituted aryl group, A
r ₂₀ , Ar ₂₁ , Ar ₂₂ and Ar ₂₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). 10. A photoconductive layer comprising, on a conductive support, a eutectic complex containing a pyrylium dye and a polymer charge transporting material represented by the following formula (9) as a main component: Electrophotographic photoreceptor. Embedded image In the formula, R ₂₂ , R ₂₃ , R ₂₄ , and R ₂₅ are a substituted or unsubstituted aryl group, Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ , Ar ₂₈
Represents the same or different arylene groups. X, k, j and n are the same as in the case of the above equation (1). 11. A pyrylium-based dye on a conductive support.
A polymer charge transport material represented by the following formula (10)
That a photoconductive layer containing a eutectic complex is provided
An electrophotographic photosensitive member characterized by the following. Embedded imageWhere R₂₆, R₂₇Is a substituted or unsubstituted aryl group,
Ar₂₉, Ar₃₀, Ar ₃₁Represents the same or different arylene groups
Express. X, k, j and n are the same as in the case of the above equation (1).
The same. 12. The electrophotographic photoreceptor according to claim 1, wherein the photoconductive layer contains a low-molecular charge transport material. 13. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transporting material represented by the following formula (11). Embedded image In the formula, R ₂₀₁ , R ₂₀₂ , R ₂₀₃ and R ₂₀₄ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted aryl group, and Ar ₁₀₁ represents a substituted or unsubstituted aryl group, Ar ₁₀₂ represents a substituted or unsubstituted arylene group, Ar ₁₀₁ and R ₂₀₁ may jointly form a ring, and n ₁ is an integer of 0 or 1. 14. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transporting material represented by the following formula (12). Embedded image In the formula, R ₂₀₅ represents a lower alkyl group, a lower alkoxy group or a halogen atom, n ₂ represents an integer of 0 to 4,
R ₂₀₆ and R ₂₀₇ may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. 15. The electrophotographic photoconductor according to claim 12, wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (13). Embedded image In the formula, R ₂₀₈ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group or a heterocyclic group;
₂₀₉ and R ₂₁₀ may be the same or different and include a hydrogen atom,
Lower alkyl group, a hydroxyalkyl group C ₁ -C _4, C
₁ -C ₄ a chloroalkyl group, or a substituted or unsubstituted aralkyl group, also, R ₂₀₉ and R ₂₁₀ may form a heterocyclic ring containing a nitrogen jointly, R _211, R ₂₁₂ are each the same And may be different, and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. 16. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transporting material represented by the following formula (14). Embedded image In the formula, R ₂₁₃ represents a hydrogen atom or a halogen atom;
₂₁₄ is a substituted or unsubstituted aromatic residue or heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, Selected from the group consisting of an alkoxy group and a nitro group). 17. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transporting material represented by the following formula (15). Embedded image In the formula, R ₂₁₅ , R ₂₁₆ and R ₂₁₇ each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a heterocyclic group, and at least two of R ₂₁₅ , R ₂₁₆ and R ₂₁₇ are aryl. Represents a group or a heterocyclic group. 18. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transport material represented by the following formula (16). Embedded image In the formula, Ar ₁₀₃ and Ar ₁₀₄ each represent a substituted or unsubstituted aryl group or a heteroaromatic ring. 19. The electrophotographic photosensitive member according to claim 12, wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (17). Embedded image In the formula, Ar ₁₀₅ represents a substituted or unsubstituted aryl group or a heteroaromatic ring, and R ₂₁₈ and R ₂₁₉ are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a heterocyclic group, respectively. _At least one of ₂₁₈ and R ₂₁₉ comprises an aryl group or a heterocyclic group. 20. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transporting material represented by the following formula (18). Embedded image In the formula, R ₂₂₀ and R ₂₂₂ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group,
R ₂₂₁ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group, and n ₃ represents an integer of 0 or 1. 21. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transport material represented by the following formula (19). Embedded image In the formula, R ₂₂₃ represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, or a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group (provided that the substituent is a di-lower alkyl group). Amino group, lower alkyl group, lower alkoxy group, halogen atom, aralkylamino group or amino group). 22. The electrophotographic photoconductor according to claim 12, wherein the photoconductive layer contains a low-molecular charge transporting material represented by the following formula (20). Embedded image In the formula, Ar ₁₀₆ represents a substituted or unsubstituted biphenylene group, and R ₂₂₄ , R ₂₂₅ and R _{226 each} represent a hydrogen atom, a halogen atom, a cyano group, or an alkyl group, an alkoxy group which may have a substituent, Aryloxy group, alkyl mercapto group, methylenedioxy group, methylenedithio group,
Represents an aryl group, and R ₂₂₄ , R ₂₂₅ and R ₂₂₆ may be the same or different. U, v, and w each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₂₂₄ , R ₂₂₅ and R ₂₂₆ may be the same or different. 23. The electrophotographic photoreceptor according to claim 12, wherein the photoconductive layer contains a low molecular charge transporting material represented by the following formula (21). Embedded image Wherein, R ₂₂₇ and R ₂₂₈ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, R ₂₂₇
And at least one of R ₂₂₈ represents a substituted or unsubstituted aryl group.