JP2020034618A - Charge transporting resin, and method for manufacturing charge transporting resin - Google Patents

Abstract

To provide a new charge transporting resin.SOLUTION: A charge transporting resin has a structure represented by a general formula (1-1) and a structure represented by a general formula (1-2), and has a weight average molecular weight of 200,000 or less. In the general formula (1-1) and the general formula (1-2), Aand Aeach independently represent a divalent organic group having charge transporting property, Tand Teach independently represent a linear or branched divalent hydrocarbon group having 1 to 10 carbon atoms, Yand Yeach independently represent a hydrogen atom, a polymerizable functional group or a group having a polymerizable functional group, and p and q each independently represent 0 or 1. The number of the structure represented by the general formula (1-1) contained in the charge transporting resin is 5 or more, and the number of the structure represented by the general formula (1-2) contained in the charge transporting resin is 5 or more.SELECTED DRAWING: None

Description

  The present invention relates to a charge transporting resin and a method for producing the charge transporting resin.

In recent years, electronic devices using organic compounds, such as electrophotographic photoreceptors, organic EL devices, organic transistors, and organic solar cells, have been actively developed.
In particular, in terms of heat resistance and strength, a crosslinked structure is effective. For example, an organic EL device using a thermosetting or photocured film (for example, see Patent Document 1), containing a charge transporting group (For example, see Patent Documents 2 to 4) and an electrophotographic photosensitive member in which an acrylic polymer containing a charge transporting group and a reactive group is crosslinked after forming a film (for example, see Patent Document 5) ), And a film cured by applying a liquid containing a photocurable acrylic monomer (see, for example, Patent Document 6). In addition, a mixture of a monomer having a carbon-carbon double bond, a charge transfer material having a carbon-carbon double bond, and a binder resin may be prepared by heating the carbon-carbon double bond of the monomer and the charge transfer material by energy of heat or light. A film formed by reacting a carbon-carbon double bond is disclosed. In particular, a monofunctional methacryl-modified charge transfer material, a methacryl monomer having no charge transport property, and a polycarbonate resin are disclosed. One cured using an oxide is disclosed (for example, see Patent Document 7). Further, a charge transporting polyester resin having a polymerizable functional group in a polymer main chain is also disclosed (for example, see Patent Document 8).

  Further, an organic semiconductor film and an electrophotographic photoreceptor (see, for example, Patent Document 9) formed by curing a film by introducing a functional group into the terminal of a charge transporting resin are disclosed.

WO 1997/033193 JP-A-5-202135 JP-A-6-256428 JP-A-9-12630 JP 2005-2291 A JP-A-5-40360 JP-A-5-216249 JP 2013-73015 A JP 2001-117252 A

  An object of the present invention is to provide a novel charge transporting resin.

The above problem is solved by the following means. That is,
<1>
A charge transporting resin having a structure represented by the following general formula (1-1) and a structure represented by the following general formula (1-2), and having a weight average molecular weight of 200,000 or less.

In the general formulas (1-1) and (1-2), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent A linear or branched divalent hydrocarbon group having 1 to 10 carbon atoms, Y ¹ and Y ² each independently represent a hydrogen atom, a polymerizable functional group, or a group having a polymerizable functional group; , P and q each independently represent 0 or 1. The number of the structures represented by the general formula (1-1) contained in the charge transporting resin is 5 or more, and the number of the structures represented by the general formula (1-2) contained in the charge transporting resin is five or more. The number of structures is 5 or more.
<2>
The total number of hydroxyl groups contained in the entire charge transport resin and M _H, when the total number of polymerizable functional groups contained in the entire charge transporting resin was M _P, satisfies the following formula (A1) according to <1> Charge transporting resin.
Formula (A1): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.9
<3>
Wherein _{M H} and the _{M P} is a charge-transporting resin according to the following formula satisfies the (A2) <2>.
Formula (A2): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.6
<4>
The polymerizable functional group includes a group represented by the following general formula (P1), a group represented by the following general formula (P2), a group represented by the following general formula (P3), and a group represented by the following general formula (P4). The charge-transporting resin according to any one of <1> to <3>, which is at least one selected from a group represented by the following general formula (P5) and a group represented by the following general formula (P5).

In the general formulas (P1) to (P5), R ^{3 to} R ⁶ each independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and * indicates a bonding position.
<5>
A ¹ and A ² in the general formulas (1-1) and (1-2) represent any one of <1> to <4>, which represents a divalent organic group having a hole transporting ability. 3. The charge transporting resin according to item 1.
<6>
A ¹ and A ² in the general formulas (1-1) and (1-2) each independently represent a divalent organic group represented by the following general formula (2). The charge transporting resin according to the above.

In the general formula (2), R ¹ and R ² each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a substituted or unsubstituted aryl group, and X represents a substituted or unsubstituted divalent. Represents an organic group, and k and m each independently represent 0 or 1.
<7>
The charge transporting resin according to any one of <1> to <6>, having a weight average molecular weight of 2,000 to 500,000.
<8>
The charge transporting resin according to <7>, wherein the weight average molecular weight is from 3,000 to 200,000.
<9>
T ¹ and T ² in the general formulas (1-1) and (1-2) each independently represent a linear or branched divalent hydrocarbon group having 1 to 8 carbon atoms. The charge transporting resin according to any one of <1> to <8>.
<10>
The charge transport according to any one of <1> to <9>, including a polymerization step of polymerizing a compound represented by the following general formula (3) and a compound represented by the following general formula (4). Production method of conductive resin.

In the general formulas (3) and (4), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent a group having 1 to 10 carbon atoms. It represents a linear or branched divalent hydrocarbon group, and p and q each independently represent 0 or 1.
<11>
<10> The charge transporting property according to <10>, further comprising: introducing a polymerizable functional group into the polymer by reacting a compound having a polymerizable functional group with the polymer obtained in the polymerization step. Method of manufacturing resin.

According to the invention according to <1>, <4>, <5>, <6>, <7>, <8>, or <9>, a novel charge transporting resin is provided.
According to the invention according to <2>, a charge transporting resin having high mechanical strength is provided as compared with a case where the formula (A1) is not satisfied.
According to the invention according to <3>, a charge transporting resin having higher mechanical strength is provided as compared with a case where the formula (A2) is not satisfied.
According to the invention according to <10> or <11>, a method for producing a charge transporting resin from which a novel charge transporting resin is obtained is provided.

3 is a graph showing an IR spectrum of a resin (1-1) synthesized in an example. 3 is a graph showing an IR spectrum of a resin (1-2) synthesized in an example. The graph which shows the IR spectrum of the resin (1-6) synthesize | combined in the Example. The graph which shows the IR spectrum of the resin (1-7) synthesize | combined in the Example. The graph which shows the IR spectrum of the resin (1-9) synthesize | combined in the Example. The graph which shows the IR spectrum of the resin (1-10) synthesize | combined in the Example. The graph which shows the IR spectrum of the resin (1-19) synthesize | combined in the Example. The graph which shows the IR spectrum of the resin (1-20) synthesize | combined in the Example. (A), (B), and (C) are explanatory diagrams each showing a ghost evaluation standard.

  Hereinafter, embodiments of the present invention will be described in detail. These descriptions and examples illustrate the embodiments and do not limit the scope of the invention.

<Charge transport resin>
The charge transporting resin according to this embodiment has at least a structure represented by the following general formula (1-1) and a structure represented by the following general formula (1-2), and has a weight average molecular weight of 200,000 or less. It is.

In the general formulas (1-1) and (1-2), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent A linear or branched divalent hydrocarbon group having 1 to 10 carbon atoms, Y ¹ and Y ² each independently represent a hydrogen atom, a polymerizable functional group, or a group having a polymerizable functional group; , P and q each independently represent 0 or 1. The number of the structures represented by the general formula (1-1) contained in the charge transporting resin is 5 or more, and the number of the structures represented by the general formula (1-2) contained in the charge transporting resin is five or more. The number of structures is 5 or more.

The charge transporting resin having a structure represented by the general formula (1-1) and the general formula (1-2) and having a weight average molecular weight of 200,000 or less (hereinafter also referred to as “specific charge transporting resin”) is Since it has at least one of a group having a polymerizable functional group and a hydroxyl group, it is considered that the solvent resistance and the mechanical strength of a film formed using the group are increased. In particular, when at least a part of the plurality of Y ¹ and Y ² present in the specific charge transporting resin is a polymerizable functional group or a group having a polymerizable functional group, after forming a film, energy such as heat or light is obtained. To give a cross-linking reaction, it is possible to obtain a film having excellent film-forming properties and having higher solvent resistance and higher mechanical strength.
Therefore, for example, when a specific charge transporting resin is used as the resin of the surface layer of the electrophotographic photoreceptor, the mechanical strength of the surface layer is high, and the resistance to film reduction due to rubbing with a blade or the like is high, Long life can be achieved. When a specific charge transporting resin is used as the resin contained in each layer of the organic EL element (that is, the organic electroluminescent element), the solvent containing the specific charge transporting resin has high solvent resistance. By forming an upper layer by coating with a coating solution containing the composition, lamination by a coating method with excellent productivity is realized.

In order to increase the strength of the formed film, the specific charge transporting resin is mixed with a monomer having a polyfunctional polymerizable functional group to form a film, thereby further increasing the crosslink density and increasing the mechanical strength. A film having higher solvent resistance can be obtained. This is because at least one of the hydroxyl group and the polymerizable functional group contained in the specific charge transporting resin exists in a state branched from the main chain (that is, a state having a high degree of freedom of movement), and thus is efficiently crosslinked. It is inferred that
As described above, by forming a crosslinked structure, a film having higher heat resistance and solvent resistance can be obtained. In an organic device using the film (for example, an electrophotographic photosensitive member, an organic EL element, etc.), Stable performance can be obtained over a long period.

-Description of each group in general formula (1-1) and general formula (1-2)-
A ¹ and A ² in the general formulas (1-1) and (1-2) each independently represent a divalent organic group having a charge transporting property, and specifically, a phthalocyanine compound, From porphyrin compounds, azobenzene compounds, triarylamine compounds, benzidine compounds, arylalkane compounds, aryl-substituted ethylene compounds, stilbene compounds, anthracene compounds, hydrazone compounds, quinone compounds, fluorenone compounds, etc. Derived divalent organic groups are mentioned.
A ¹ and A ² in the general formula (1-1) and the general formula (1-2) are preferably an organic group having a hole transporting ability among these, and among them, triarylamine More preferably, it is an organic group having at least one selected from a skeleton, a benzidine skeleton, and a stilbene skeleton.

Preferably, A ¹ and A ² in the general formulas (1-1) and (1-2) are each independently a divalent organic group represented by the following general formula (2).

In the general formula (2), R ¹ and R ² each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a substituted or unsubstituted aryl group, and X represents a substituted or unsubstituted divalent group. And k and m each independently represent 0 or 1.

  X in the general formula (2) represents a substituted or unsubstituted divalent organic group, and may be a group having or not having an aromatic ring. X in the general formula (2) is more preferably a group having an aromatic ring, and among them, a substituted or unsubstituted divalent aromatic group or a substituted or unsubstituted aromatic ring having 2 to 10 aromatic rings. The following divalent polynuclear aromatic hydrocarbon groups, substituted or unsubstituted divalent fused aromatic hydrocarbon groups having 2 to 10 aromatic rings, or substituted or unsubstituted divalent aromatic heterocyclic groups More preferably, there is.

“Polynuclear aromatic hydrocarbon group” refers to a hydrocarbon group in which two or more aromatic rings composed of carbon and hydrogen exist, and the rings are bonded to each other by a carbon-carbon bond. Specifically, a hydrocarbon group in which carbons constituting an aromatic ring are directly bonded to each other by a carbon-carbon bond, or a hydrocarbon group in which the aromatic rings have 1 to 18 carbon atoms (an alkyl chain or an alkylene chain). And a linked hydrocarbon group.
Specific examples of the polynuclear aromatic hydrocarbon group include divalent groups from which two hydrogen atoms have been removed, such as biphenyl, terphenyl, stilbene, and triphenylethylene.
Note that the aromatic ring constituting the polynuclear aromatic hydrocarbon group may be a condensed aromatic hydrocarbon group described later or an aromatic heterocyclic ring. Specific examples of the condensed aromatic hydrocarbon group and the aromatic heterocyclic ring constituting the polynuclear aromatic hydrocarbon group include, for example, those similar to the compounds of the specific examples of the condensed aromatic hydrocarbon group and the aromatic heterocyclic ring described below. No.

  A “condensed aromatic hydrocarbon group” is a hydrocarbon in which two or more aromatic rings composed of carbon and hydrogen exist, and these aromatic rings share a pair of carbon atoms that are adjacently bonded to each other. Represents a group. Specifically, a divalent group from which two hydrogen atoms have been removed, such as naphthalene, anthracene, phenanthrene, pyrene, perylene, and fluorene, may be mentioned.

“Aromatic heterocycle” refers to an aromatic ring that also contains elements other than carbon and hydrogen.
Examples of the number of atoms (Nr) constituting the ring skeleton of the aromatic heterocycle include Nr = 5, Nr = 6, and the like. The type and number of atoms (heteroatoms) other than carbon atoms constituting the ring skeleton are not limited. Examples of the type of the hetero atom include a sulfur atom, a nitrogen atom, and an oxygen atom. Further, the aromatic heterocyclic ring may include two or more hetero atoms in the ring skeleton, or may include two or more hetero atoms.

  In particular, examples of the heterocycle having a ring skeleton structure of Nr = 5 (that is, a 5-membered ring structure) include, for example, thiophene, thiofin, pyrrole, furan, or a heterocycle obtained by further substituting the carbon at the 3- and 4-positions with nitrogen. And the like. Examples of the heterocyclic ring having a ring skeleton structure of Nr = 6 (that is, a 6-membered ring structure) include a pyridine ring and the like.

Examples of the substituent for the aromatic ring, the polynuclear aromatic ring, and the condensed aromatic ring include an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a substituted amino group, and a halogen atom.
The alkyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
The alkoxyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
The aryl group preferably has 6 to 20 carbon atoms, and examples thereof include a phenyl group and a toluyl group.
The aralkyl group preferably has 7 to 20 carbon atoms, and examples thereof include a benzyl group and a phenethyl group.
Examples of the substituent of the substituted amino group include an alkyl group, an aryl group, and an aralkyl group, and specific examples are as described above.
Examples of the substituent of the substituted aryl group and the substituted aralkyl group include a hydrogen atom, an alkyl group, an alkoxy group, a substituted amino group, and a halogen atom.

  Preferred examples of X in the general formula (2) include groups selected from the following formulas (X1) to (X7).

Formula (X1) in ~ ^{(X7), R 13} is a hydrogen atom, 1 or more and 4 or less carbon atoms alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aralkyl ^{group, R} 14 to R ^{And 19} independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted aralkyl group, or a halogen atom. , A represents 0 or 1, and V represents at least one group selected from the following formulas (V8) to (V17).

  In the above formulas (V8) to (V17), b represents an integer of 1 or more and 10 or less, and c represents an integer of 1 or more and 3 or less.

  X in the general formula (2) is preferably a divalent organic group selected from the group (A) shown below, and more preferably a divalent organic group selected from the group (B) shown below. Particularly preferred.

R ¹ and R ² in the general formula (2) each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a substituted or unsubstituted aryl group.
The alkyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
The alkoxyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
The aryl group preferably has 6 to 20 carbon atoms, and examples thereof include a phenyl group and a toluyl group.
Examples of the substituent of the substituted aryl group include an alkyl group, an alkoxy group, a substituted amino group, and a halogen atom.

Among the above R ¹ and R ² , a hydrogen atom, a methyl group, an ethyl group, and a phenyl group are particularly preferable.
The position where R ¹ and R ² are substituted is preferably a meta position or a para position with respect to the position where nitrogen (N) is bonded.

Note that the ^{A 2} in ^{A 1} of the general formula in formula (1-1) (1-2), may be different even in the same. Further, a plurality of A ¹ in the specific charge transporting resins may be different from each other in the same part in all the same, it is preferred that all are identical. Similarly, a plurality of A ² in the specific charge transporting resin may be all the same, partially the same, or different from each other, but are preferably all the same.

T ¹ and T ² in the general formula (1-1) and the general formula (1-2) each independently represent a linear or branched divalent hydrocarbon group having 1 to 10 carbon atoms. T ¹ and T ² in the general formula (1-1) and the general formula (1-2) are each independently a straight-chain or branched divalent hydrocarbon group having 1 to 8 carbon atoms. Is preferred. When the divalent hydrocarbon group is linear, the number of carbon atoms is more preferably in the range of 1 or more and 6 or less, and further preferably in the range of 2 or more and 6 or less. When the divalent hydrocarbon group is branched, the number of carbon atoms is more preferably in the range of 2 or more and 10 or less, and further preferably in the range of 3 or more and 7 or less.
The following are examples of specific structure of the group represented by group and T ² is represented by T ¹ (hydrocarbon group T-. 1 to hydrocarbon radicals T-32). However, A ¹ or A ² in the general formula (1-1) and the general formula (1-2) may be bonded to either side of the following hydrocarbon group. on the right side of -5, the left side of the structure T-5 if referred to as T-5l, indicating that ^{the a 1} or ^{a 2} is bonded in the formula (1-1) and the general formula (1-2).

In Formula (1-1), when p is 1, T ¹ adjacent to the carbonyl group is preferably the above-mentioned structures T-1, T-2, and T-4. Similarly, in the general formula (1-2), when q is 1, the ^{T 2} adjacent to the carbonyl group, the structure T-1, T-2, and T-4 is preferred.

Note that the ^{T 2} in ^{T 1} and the general formula in formula (1-1) (1-2), may be different even in the same. Further, a plurality of T ¹ during a specific charge transporting resins may be different from each other in the same part in all the same, it is preferred that all are identical. Similarly, a plurality of T ² in the specific charge transporting resins may be different from each other in the same part in all the same, it is preferred that all are identical.

Hereinafter, A ¹ and T ¹ in the case where A ¹ and A ^{2 in the} general formulas (1-1) and (1-2) represent the divalent organic group represented by the general formula (2). (Ie, X, R ¹ , R ² , k, and m in the general formula (2), and T ¹ and p in the general formula (1-1)) or A ² and T combination of ² and q (i.e., the general formula (2) in the ^X, R ^{1, R} 2, k, and m, and the general formula (a combination of ^{T 2} and q in 1-2)) specific examples of Although shown, the present invention is not limited to these specific examples.
In addition, in the following table, the numbers described in the columns of “R ¹ ” and “R ² ” represent the positions of the bonds. Also, the number that is listed in the "T ¹ or T ^2" is above specifically indicated structural formulas given number of hydrocarbon group (T-1) means - a (T-32). Incidentally, in the column of "T ¹ or T ^2", for example, the right-hand structure T-5 if referred to as "T-5r", the left side of the structure T-5 if referred to as "T-5l" aryl This indicates that an amine skeleton (that is, A ¹ or A ² in the general formulas (1-1) and (1-2)) is bonded. Further, in the following table, the value shown in the “bonding position” indicates that the bond is at the position of the numerical value described in the benzene ring in the general formula (2), and when k is 1, when (k) is 1, The benzene ring in parentheses indicates that it is bonded to the same position as the benzene ring in which the number is described.

In formulas (1-1) and (1-2), Y ¹ and Y ² each independently represent a hydrogen atom, a polymerizable functional group, or a group having a polymerizable functional group.
Examples of the polymerizable functional group include a group containing at least one selected from a carbon-carbon double bond, an epoxy group, and an oxetane group. Specific examples of the polymerizable functional group include, for example, a vinyl group, a vinyl ether group, a group represented by the following general formula (P1), a group represented by the following general formula (P2), and a group represented by the following general formula (P3). A group represented by the following general formula (P4), a group represented by the following general formula (P5), and the like.
Among these, the polymerizable functional group includes a group represented by the following general formula (P1), a group represented by the following general formula (P2), a group represented by the following general formula (P3), and a group represented by the following general formula (P3). It is preferably at least one selected from the group represented by P4) and the group represented by the following general formula (P5).

In the general formulas (P1) to (P5), R ^{3 to} R ⁶ each independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and * indicates a bonding position.
The alkyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and an isopropyl group. The alkyl group preferably has 1 to 5 carbon atoms, more preferably has 1 to 3 carbon atoms, and particularly preferably has 1 to 2 carbon atoms.
The alkoxyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group. The alkoxy group preferably has 1 to 5 carbon atoms, more preferably has 1 to 3 carbon atoms, and particularly preferably has 1 to 2 carbon atoms.
The substitution position of the group represented by the general formula (P3) may be any of the ortho position, the meta position, and the para position, and among them, at least one selected from the meta position and the para position is preferable, and the para position is preferable. Is more preferred. In the case where the specific charge transporting resin has a plurality of groups represented by the general formula (P3), at least two of the substitution positions selected from the ortho, meta, and para positions are mixed. You may.

When Y ¹ and Y ² in the general formulas (1-1) and (1-2) represent a group having a polymerizable functional group, for example, the polymerizable functional group further having a substituent may be an oxygen atom And the case where the substituted or unsubstituted polymerizable functional group is bonded to an oxygen atom via a linking group.

Examples of the substituent further included in the polymerizable functional group include a hydroxyl group, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a substituted amino group, and a halogen atom.
The alkyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and an isopropyl group. The alkyl group preferably has 1 to 5 carbon atoms, more preferably has 1 to 3 carbon atoms, and particularly preferably has 1 to 2 carbon atoms.
The alkoxyl group preferably has 1 to 10 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group. The alkoxy group preferably has 1 to 5 carbon atoms, more preferably has 1 to 3 carbon atoms, and particularly preferably has 1 to 2 carbon atoms.
The aryl group preferably has 6 to 20 carbon atoms, and examples thereof include a phenyl group and a toluyl group.
The aralkyl group preferably has 7 to 20 carbon atoms, and examples thereof include a benzyl group and a phenethyl group.
Examples of the substituent of the substituted amino group include an alkyl group, an aryl group, and an aralkyl group, and specific examples are as described above.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and the like.

  Examples of the linking group linking the polymerizable functional group and the oxygen atom include, for example, a divalent linking group composed of at least one atom selected from a carbon atom and an oxygen atom (hereinafter, also referred to as L1). ). Examples of L1 include a group formed by arbitrarily combining alkylene, -O-, and -C (= O)-. The total number of atoms other than hydrogen atoms constituting L1 is, for example, 1 or more and 15 or less, preferably 1 or more, and more preferably 1 or more and 6 or less. When the total number of atoms other than the hydrogen atoms constituting L1 is in the above range, the ratio of the charge transporting skeleton is higher than in the case where the number is more than the above range, and the electric characteristics are improved.

The following, among the groups represented by group and Y ² is expressed by Y ^1, examples of the specific structure of the group having a polymerizable functional group or a polymerizable functional group (group Y-. 1 to group Y-22 ). However, in the following formula, Me means a methyl group and Et means an ethyl group.

Note that the ^{Y 2} in ^{Y 1} and formula in the general formula (1-1) (1-2), may be different even in the same. Further, a plurality of Y ¹ in the specific charge transporting resin may be all the same, partly the same, or different from each other. Similarly, the plurality of Y ² in the specific charge transporting resin may be all the same, partially the same, or different from each other.
That is, in the molecule of the specific charge transporting resin, a group having a hydrogen atom, a polymerizable functional group, and a polymerizable functional group as Y ¹ and Y ² in the general formulas (1-1) and (1-2). And at least one group selected from the following. Further, all of the plurality of Y ¹ and the plurality of Y ² may be hydrogen atoms, and all of the plurality of Y ¹ and the plurality of Y ² are selected from a polymerizable functional group and a group having a polymerizable functional group. At least one type may be used.

The number of the structures represented by the general formula (1-1) and the number of the structures represented by the general formula (1-2) contained in the specific charge transporting resin are each independently 5 or more, preferably It is 5 or more and 5000 or less, more preferably 5 or more and 2000 or less, and further preferably 10 or more and 1000 or less.
Note that a plurality of structures represented by the general formula (1-1) may not be adjacent to each other. Similarly, a plurality of structures represented by the general formula (1-2) may not be adjacent to each other.

  The specific charge transporting resin has, for example, a region where the structure represented by the general formula (1-1) and the structure represented by the general formula (1-2) are alternately adjacently bonded. You may. That is, the specific charge transporting resin may be a resin having a structure represented by the following general formula (1-3). The number of structures represented by the following general formula (1-3) contained in the specific charge transporting resin is, for example, 5 or more and 5000 or less, preferably 5 or more and 2000 or less, more preferably 10 or more and 1000 or less. Further, the proportion of the structure represented by the following general formula (1-3) to the entire specific charge transporting resin is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more.

In the general formula (1-3), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent a straight chain having 1 to 10 carbon atoms. Jo or shows a branched divalent hydrocarbon group, Y ¹ and Y ² each independently represent a hydrogen atom, polymerizable functional group, or a group having a polymerizable functional group, p and q are each independently 0 Or 1 is shown.
That is, in the general formula (1-3), A ¹ , A ² , T ¹ , T ² , Y ¹ , Y ² , p, and q represent the general formula (1-1) and the general formula (1), respectively. The same as A ¹ , A ² , T ¹ , T ² , Y ¹ , Y ² , p and q in -2).

-Description of specific charge transporting resin-
The specific charge transporting resin only needs to have at least the structure represented by the general formula (1-1) and the structure represented by the general formula (1-2) in the molecule. ) And the structure represented by the general formula (1-2), and may have another structure in the molecule. For example, a form in which a monovalent substituent or another monovalent structural unit is bonded to the terminal of the structure represented by the general formula (1-1), or the terminal of the structure represented by the general formula (1-2) Examples include a form in which a monovalent substituent or another monovalent structural unit is bonded. Examples of the form having a structure other than the structure represented by the general formula (1-1) and the structure represented by the general formula (1-2) in the main chain of the specific charge transporting resin include, for example, A form in which the unit of the structure represented by the general formula (1-1) and the unit of the structure represented by the general formula (1-2) are bonded via another structure is exemplified.
When the specific charge transporting resin has another structure in the molecule, the total of the structure represented by the general formula (1-1) and the structure represented by the general formula (1-2) with respect to the entire specific charge transporting resin Is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more.
Note that the total ratio of the structure represented by the general formula (1-1) and the structure represented by the general formula (1-2) is calculated from an area ratio of each peak in an NMR spectrum or an infrared absorption spectrum. Is done. Alternatively, it may be calculated by quantifying the amount of a monomer remaining without polymerization (for example, a compound represented by the following general formula (3) and a compound represented by the general formula (4)).

The total number of hydroxyl groups contained in the entire specific charge transporting resin and M _H, when the total number of polymerizable functional groups contained in the entire specific charge transporting resin was M _P, preferably satisfies the following formula (A1), It is more preferable that the following formula (A2) is satisfied, and it is more preferable that the following formula (A3) is satisfied.
Formula (A1): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.9
Formula (A2): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.6
Formula (A3): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.3
The value of M _H / (M _H + M _P ) is calculated from the area ratio of each peak in the NMR spectrum or infrared absorption spectrum.

The weight average molecular weight of the specific charge transporting resin is, for example, from 2,000 to 500,000, preferably from 3,000 to 200,000, more preferably from 4,000 to 100,000.
The weight-average molecular weight is measured by preparing a 0.1% by mass THF (tetrahydrofuran) solution of a compound to be measured and using a differential refractive index detector (RI) to perform gel permeation chromatography (GPC) on a standard sample. Using a styrene polymer.

Hereinafter, specific examples of the specific charge transporting resin in which A ¹ in the above general formula (1-1) and A ² in the above general formula (1-2) are the above general formula (2) are shown. It is not limited.
In the following table, the numbers described in the columns of “A ¹ , T ¹ , p” and “A ² , T ² , q” correspond to A ¹ , T ^1, and p in the general formula (1-1). Or the numbers (2-1) to (2-102) given to specific examples of the combination of A ² , T ² and q in the general formula (1-2). In addition, among the numbers described in the column of “Y ¹ or Y ² ”, H means a hydrogen atom, and the other numbers indicate specific structures of the polymerizable functional group or the group having a polymerizable functional group. The numbers (Y-1) to (Y-22) attached to the examples are meant. In the following table, “n1” means the number of structures represented by the general formula (1-1) possessed by the specific charge transporting resin, and “n2” represents the general formula possessed by the specific charge transporting resin It means the number of structures represented by (1-2).

-Synthesis method (Production method of specific charge transporting resin)-
Next, the synthesis method will be described.
Among the specific charge transporting resins, a charge transporting resin in which all of a plurality of Y ¹ and a plurality of Y ² are hydrogen atoms (hereinafter, also referred to as “first specific charge transporting resin”) has, for example, the following general formula: It is obtained by polymerization of a compound represented by (3) and a compound represented by the following general formula (4) (polymerization step).
Specifically, for example, a compound represented by the following general formula (3) and a compound represented by the following general formula (4) are used in an equivalent amount, and the synthesis is performed using a catalyst in a solvent.

In the general formulas (3) and (4), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent a group having 1 to 10 carbon atoms. It represents a linear or branched divalent hydrocarbon group, and p and q each independently represent 0 or 1.
Note that A ¹ and A ² , T ¹ and T ² , and p and q in the general formulas (3) and (4) are the same as those in the general formulas (1-1) and (1-2). Same as A ¹ and A ² , T ¹ and T ² , and p and q.

The synthesis of the first specific charge transporting resin is performed, for example, by using an equivalent amount of the compound represented by the general formula (3) and the compound represented by the general formula (4) and using a catalyst in a solvent.
Examples of the solvent include toluene, xylene, tetrahydrofuran, monochlorobenzene and the like. These may be used alone or in combination of two or more.
Examples of the solvent include toluene, xylene, tetrahydrofuran, monochlorobenzene and the like. These may be used alone or in combination of two or more.
Examples of the catalyst include quaternary ammonium salts, tertiary amines, tertiary phosphines, quaternary phosphonium salts, lithium halides, trifluoroboron complex salts and the like. These may be used alone or in combination of two or more.

  As the quaternary ammonium salt, for example, tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium hydroxide, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium hydroxide, methyltributylammonium chloride, tetramethylammonium chloride Propyl ammonium bromide, tetrabutyl ammonium chloride, tetrabutyl ammonium bromide, tetrabutyl ammonium iodide, tetrabutyl ammonium hydroxide, tetrabutyl ammonium hydrogen sulfate, methyl trioctyl ammonium chloride, methyl trioctyl ammonium bromide, ethyl trioct Ammonium chloride, ethyltrioctylammonium bromide, dilauryldimethylammonium chloride, distearyldimethylammonium chloride, stearyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium hydroxide, benzyl Triethylammonium chloride, benzyltriethylammonium bromide, benzyltriethylammonium hydroxide and the like.

Examples of the tertiary amine include triethylamine, tributylamine, dimethylethanolamine, tris (N, N-dimethylaminomethyl) phenol, tris (N, N-diethylaminomethyl) phenol, N, N-dimethylaminomethylphenol, N , N-dimethylbenzylamine and the like.
As the tertiary phosphine, for example, triphenylphosphine and the like can be mentioned.
As the quaternary phosphonium salt, for example, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, tetrabutylphosphonium iodide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, methyltributylphosphonium iodide, methyltrioctylphosphonium chloride, methyltrioctyl Examples thereof include phosphonium bromide, ethyltrioctylphosphonium chloride, ethyltrioctylphosphonium bromide, decyltributylphosphonium chloride, hexadecyltributylphosphonium chloride, and ethyltrioctylphosphonium chloride.
Examples of the lithium halide include lithium chloride and lithium bromide.
Examples of the trifluoroboron complex salt include boron trifluoride diethyl ether complex.

The amount of the catalyst to be added is, for example, based on 1 part by mass of the total monomer mass (that is, the sum of the mass of the compound represented by the general formula (3) and the mass of the compound represented by the general formula (4)). , 1 / 10,000 to 1/10 parts by mass, preferably 1/1000 to 1/50 parts by mass.
The amount of the solvent to be added is, for example, 1 part by mass or more and 100 parts by mass or less, preferably 2 parts by mass or more and 50 parts by mass or less based on 1 part by mass of the first specific charge transporting resin to be produced. is there.
The reaction temperature (that is, the polymerization temperature of the compound represented by the general formula (3) and the compound represented by the general formula (4)) is not particularly limited, and may be, for example, in the range of 30 ° C to 100 ° C. No.

After the polymerization reaction between the compound represented by the general formula (3) and the compound represented by the general formula (4) is completed, for example, a poor solvent (for example, methanol) in which the obtained charge transporting resin is difficult to dissolve. , An alcohol such as ethanol, acetone, etc.) to precipitate the charge transporting resin, separate it, wash it with water, an organic solvent or the like, and dry it.
Further, if necessary, the re-precipitation treatment of dissolving in an organic solvent, dropping it into a poor solvent, and depositing a charge transporting resin may be repeated. The reprecipitation treatment is preferably performed while stirring with a mechanical stirrer or the like. The amount of the solvent for dissolving the charge transporting resin during the reprecipitation treatment is, for example, in the range of 1 part by weight or more and 100 parts by weight or less based on 3 parts by weight of the charge transporting compound, preferably 2 parts by weight. It is not less than 50 parts by mass and not more than 50 parts by mass. The amount of the poor solvent is, for example, 1 part by mass or more and 1000 parts by mass or less, preferably 10 parts by mass or more and 500 parts by mass or less based on 1 part by mass of the charge transporting resin.
After the polymerization reaction between the compound represented by the general formula (3) and the compound represented by the general formula (4) is completed, for example, the reaction solution is poured into water and a solvent such as toluene, hexane, or ethyl acetate is added. , And may be further washed with an adsorbent such as activated carbon, silica gel, porous alumina, or activated clay if necessary.
Thus, by polymerizing the compound represented by the general formula (3) and the compound represented by the general formula (4), the structure represented by the general formula (1-1) and the general formula (1) Among the specific charge transporting resins having the structure represented by -2), a specific charge transporting resin having the structure represented by the general formula (1-3) is obtained.

Charge transfer resin having at least one selected from a polymerizable functional group and a group having a polymerizable functional group as at least a part of a plurality of Y ¹ and a plurality of Y ² among the specific charge transport resin. (Hereinafter also referred to as “second specific charge transporting resin”), for example, after polymerizing the compound represented by the general formula (3) and the compound represented by the general formula (4) (ie, After the polymerization step), the polymer is obtained by reacting the obtained polymer with a compound having a polymerizable functional group to introduce a polymerizable functional group into the polymer.
Thus, the compound represented by the general formula (1-1) is obtained by polymerizing the compound represented by the general formula (3) and the compound represented by the general formula (4) and then reacting with the compound having a polymerizable functional group. ) And the specific charge transporting resin having the structure represented by the general formula (1-2), a specific charge transporting resin having a structure represented by the general formula (1-3) is obtained. Can be
The step of polymerizing the compound represented by the general formula (3) and the compound represented by the following general formula (4) (polymerization step) is described in the first method for synthesizing the specific charge transporting resin. As you did.
In the step of introducing a polymerizable functional group into the obtained polymer (that is, the introduction step), specifically, for example, the obtained polymer and a compound having a polymerizable functional group are added to a solvent, and The reaction is carried out using a catalyst according to.

  Examples of the compound having a polymerizable functional group include, for example, leaving groups (for example, an OH group, a halogen atom, or a leaving group) at Y-1 to Y-4, Y-13 to Y-14, and Y-16 to Y-18. A carboxylic acid derivative substituted with another carboxylic acid or the like, or a leaving group (for example, a halogen atom, a trifluoromethanesulfonyloxy group, or a trifluoromethanesulfonyloxy group) on Y-5 to Y-12, Y-15, and Y-19 to Y-22; or (p-toluenesulfonyloxy group, etc.). A polymerizable functional group is introduced by adding a known catalyst or a condensing agent or the like as necessary to the reaction.

Examples of the solvent used in the step of introducing a polymerizable functional group into the obtained polymer include methylene chloride, diethyl ether, tetrahydrofuran (THF), toluene, chlorobenzene, 1-chloronaphthalene, acetone, methyl ethyl ketone, N, N- Examples include dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide and the like.
The amount of the solvent to be added is, for example, 1 part by mass or more and 100 parts by mass or less, preferably 2 parts by mass or more and 50 parts by mass or less based on 1 part by mass of the obtained charge transporting resin.

When a compound having a carboxy group is used as the compound having a polymerizable functional group, for example, sulfuric acid, p-toluenesulfonic acid, or the like may be used as a catalyst.
When at least one of a carboxylic anhydride and a halide is used as the compound having a polymerizable functional group, for example, pyridine, piperidine, dimethylaminopyridine, trimethylamine, 1,8-diazabicyclo [5.4. 0] -7-undecene (DBU), triethylamine and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydride, sodium hydroxide and potassium hydroxide; and the like.
The addition amount of the catalyst is, for example, 1 equivalent to 10 equivalents, preferably 2 equivalents to 5 equivalents, based on the compound having a polymerizable functional group.
The reaction temperature (that is, the reaction temperature between the polymer and the compound having a polymerizable functional group) is not particularly limited, and may be, for example, in a range of 30 ° C or more and 100 ° C or less.

  After the reaction between the polymer and the compound having a polymerizable functional group is completed, similarly to the case where the compound represented by the general formula (3) and the compound represented by the general formula (4) are polymerized, Reprecipitation treatment and purification may be performed.

-Applications-
The specific charge transporting resin may be used, for example, as a resin contained in each layer in an organic electronic device such as an electrophotographic photosensitive member and an organic electroluminescent element. The specific charge transporting resin may be used alone or in combination with an insulating polymer compatible with the specific charge transporting resin.
Specifically, for example, a device having a structure in which a layer containing a specific charge transporting resin is provided on a support is used as an organic electronic device. Representative examples of the organic electronic device include, for example, an electrophotographic photoreceptor having a photosensitive layer, among which, in particular, those containing a specific charge transporting resin in the surface layer of the electrophotographic photoreceptor. . Further, as the charge transporting material in the photosensitive layer, an electrophotographic photosensitive member containing a specific charge transporting resin and a known charge generating material, an electrophotographic photosensitive member further containing a phthalocyanine compound crystal in the photosensitive layer, and the like are also preferable. No.

  In the above electrophotographic photoreceptor, examples of the phthalocyanine crystal used in combination with the specific charge transporting resin include, for example, a halogenated gallium phthalocyanine crystal disclosed in JP-A-5-98181 and JP-A-5-140472. And halogenated tin phthalocyanine crystals disclosed in JP-A-5-140473, hydroxygallium phthalocyanine crystals disclosed in JP-A-5-263007 and JP-A-5-279951, and JP-A-4-189873. And oxytitanium phthalocyanine hydrate crystals disclosed in JP-A-5-43813. By using the phthalocyanine crystal, an electrophotographic photoreceptor having particularly high sensitivity and excellent repetition stability can be obtained.

-Specific charge transporting resin solution-
The specific charge transporting resin solution is obtained by dissolving a charge transporting resin having a structure represented by the general formula (1-1) and a structure represented by the general formula (1-2) in a solvent.

  Examples of the solvent include aromatic solvents such as toluene and xylene; ketones such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; esters such as ethyl acetate and butyl acetate; ethers such as tetrahydrofuran and dioxane; and cellosolves such as ethylene glycol monomethyl ether. Solvents such as alcohols such as isopropyl alcohol and butanol may be used alone or as a mixed solvent.

  As a method for dissolving the specific charge transporting resin in these solvents, for example, stirring and mixing with the solvent at a temperature of 10 ° C. to 150 ° C., preferably 15 ° C. to 120 ° C. (for example, stirring and mixing while irradiating ultrasonic waves) )).

  The specific charge transporting resin solution is used, for example, for forming a film in an organic electronic device (organic EL device, electrophotographic photoreceptor, etc.), and also for forming a solar cell, an organic transistor, and the like.

-Crosslinked specific charge transporting resin-
The crosslinked specific charge transportable resin is obtained by further crosslinking the above specific charge transportable resin. Specifically, for example, a crosslinked body of the specific charge transporting resin is obtained by applying heat, light, radiation, or the like to the solution of the specific charge transporting resin. By the crosslinking, the strength and solvent resistance of the film are further improved.
When crosslinking is performed by at least one of heat and light, a polymerization initiator is not necessarily required, but at least one of a photocuring catalyst and a thermal polymerization initiator may be used. As the photo-curing catalyst and the thermal polymerization initiator, known photo-curing catalysts and thermal polymerization initiators are used. The radiation is preferably an electron beam.

  Hereinafter, Examples and Comparative Examples will be described, but the present invention is not limited to the following Examples. In the following, “parts” are based on mass unless otherwise specified.

<Synthesis example 1>
As compounds 3-2, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-2).
A 500 ml flask was charged with 80 g of the compound 3-2, 230 g of epichlorohydrin, 26.8 g of sodium hydroxide, and 3 g of triethylamine. After the atmosphere was replaced with nitrogen, the mixture was stirred at room temperature (25 ° C.) for 24 hours. After the reaction, the resultant was washed with a dilute hydrochloric acid aqueous solution and then with water. After concentration, the residue was purified by silica gel chromatography to obtain 64 g of compound 4-2.
The compound 4-2 is represented by the general formula (4), and the combination of A ² , T ² and q is the specific example number (2-2) described above.

<Synthesis Example 2>
As compounds 3-6, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-6).
110 g of compound 3-6, 60 g of epichlorohydrin, 65 g of potassium carbonate, and 300 ml of N, N-dimethylformamide were placed in a 1000 ml flask, and the mixture was purged with nitrogen and reacted at 90 ° C. for 10 hours. After the reaction, 300 ml of toluene was added, and the mixture was washed with a dilute aqueous hydrochloric acid solution and then with water. After concentration, the residue was purified by silica gel chromatography to obtain 50 g of compound 4-6.
The compound 4-6, wherein is represented by the general formula (4), and the combination of ^{A 2} and ^{T 2} and q is a preceding example number (2-6).

<Synthesis Example 3>
As compounds 3-17, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-17).
A 500 ml flask was charged with 60 g of compound 3-17, 200 g of epichlorohydrin, 17.6 g of sodium hydroxide, and 2 g of triethylamine, and the mixture was purged with nitrogen, followed by stirring at room temperature (25 ° C.) for 24 hours. After the reaction, the resultant was washed with a dilute hydrochloric acid aqueous solution and then with water. After concentration, the residue was purified by silica gel chromatography to obtain 74.5 g of compound 4-17.
The compound 4-17 is represented by the general formula (4), and the combination of A ² , T ² and q is the specific example number (2-17) described above.

Compound 4-5, compound 4-17, compound 4-83, compound 4-86, compound 4-98, compound 4-57, and compound 4-44 were obtained in the same manner as in Synthesis Example 1.
In addition, the compound 4-5, the compound 4-17, the compound 4-83, the compound 4-86, the compound 4-98, the compound 4-57, and the compound 4-44 are represented by the general formula (4). and the combination of ^{a 2} and ^{T 2} and q are each embodiment number (2-5), specific examples numbers (2-17), specific examples numbers (2-83), specific examples numbers (2-86 ), A specific example number (2-98), a specific example number (2-57), and a specific example number (2-44).

Compound 4-25 and compound 4-92 were obtained in the same manner as in Synthesis Example 2.
In addition, the compound 4-25 and the compound 4-92 are represented by the general formula (4), and the combination of A ² , T ^2, and q is the specific example number (2-25) and the specific example, respectively. Example number (2-92).

<Example 1: Synthesis of resin (1-1)>
As compounds 3-29, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-29).
In a 2000 ml flask, 79.8 g of compound 3-29, 700 ml of tetrahydrofuran, and 1.8 g of boron trifluoride diethyl ether complex were placed, and the mixture was purged with nitrogen and heated to 50 ° C. A solution in which 50.0 g of the compound 4-5 was dissolved in 200 ml of tetrahydrofuran was dropped into this solution over 30 minutes. After completion of the dropping, the mixture was reacted for 2 hours, and then dropped into 10 L of methanol to precipitate a polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 107.0 g of a resin (1-1) which is a resin of the number (1-1) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 60000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 1.0.
FIG. 1 shows an IR spectrum of the obtained resin (1-1).

<Example 2: Synthesis of resin (1-2)>
10 g of the resin (1-1) obtained in Example 1 was placed in a 300 ml flask, 18 g of 4-iodomethylstyrene and 0.1 g of nitrobenzene were placed in the flask, and 100 ml of tetrahydrofuran was added and dissolved. To this was added 5.8 g of sodium t-butoxy at room temperature (25 ° C.) over 2 hours, and the mixture was reacted at 50 ° C. for 3 hours. After completion of the reaction, 100 ml of toluene was added, washed with dilute hydrochloric acid and then with water, and dropped into 500 ml of methanol to precipitate a polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 10.1 g of a resin (1-2) which is a resin of the number (1-2) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 61,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.
FIG. 2 shows the IR spectrum of the obtained resin (1-2).

<Example 3: Synthesis of resin (1-3)>
The numbers shown as specific examples of the specific charge transporting resin were the same as in Example 2 except that the amount of 4-iodomethylstyrene added was 1.0 g and the amount of sodium t-butoxide was 0.3 g. 9.9 g of resin (1-3), which is the resin of 1-3), was obtained.
The molecular weight measured by GPC was 60000 in terms of polystyrene. The value of the _{M H / (M H + M} P) was 0.95.

<Example 4: Synthesis of resin (1-4)>
In the same manner as in Example 2 except that the amount of 4-iodomethylstyrene added was 1.8 g and the amount of sodium t-butoxy added was 0.5 g, the numbers shown as specific examples of the specific charge transporting resin ( 9.9 g of resin (1-4), which is the resin of 1-4), was obtained.
The molecular weight measured by GPC was 60000 in terms of polystyrene. The value of the _{M H / (M H + M} P) was 0.85.

<Example 5: Synthesis of resin (1-5)>
In the same manner as in Example 2 except that the amount of 4-iodomethylstyrene added was 9.0 g and the amount of sodium t-butoxide was 2.9 g, the numbers shown as specific examples of the specific charge transporting resin ( 9.9 g of resin (1-5), which is the resin of 1-5), was obtained.
The molecular weight measured by GPC was 60000 in terms of polystyrene. The value of the _{M H / (M H + M} P) was 0.45.

<Example 6: Synthesis of resin (1-6)>
As compounds 3-17, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-17).
In a 1000 ml flask, 39.4 g of compound 3-17, 700 ml of tetrahydrofuran, and 1.0 g of boron trifluoride diethyl ether complex were placed, and the mixture was purged with nitrogen and heated to 50 ° C. To this solution, a solution of 45.2 g of compound 4-17 dissolved in 200 ml of tetrahydrofuran was added dropwise over 30 minutes. After completion of the dropping, the mixture was reacted for 2 hours, and then dropped into 10 L of methanol to precipitate a polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 75.0 g of a resin (1-6) which is a resin of the number (1-6) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 40,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 1.0.
FIG. 3 shows the IR spectrum of the obtained resin (1-6).

<Example 7: Synthesis of resin (1-7)>
A 200 ml flask was charged with 8.0 g of the resin (1-6) obtained in Example 6, 100 ml of tetrahydrofuran, 52.0 g of methacrylic acid chloride, and 50.0 of triethylamine, and reacted at room temperature (25 ° C.) for 24 hours. did. After completion of the reaction, the polymer was dropped into 1 L of methanol to precipitate the polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 7.1 g of a resin (1-7) which is a resin of the number (1-7) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 41,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.
FIG. 4 shows the IR spectrum of the obtained resin (1-7).

<Example 8: Synthesis of resin (1-8)>
A 500 ml flask was charged with 8.0 g of the resin (1-6) obtained in Example 6, 100 ml of tetrahydrofuran, 1.0 g of methacrylic acid chloride and 1.0 of triethylamine, and reacted at room temperature (25 ° C.) for 24 hours. did. After completion of the reaction, the polymer was dropped into 1 L of methanol to precipitate the polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 7.4 g of a resin (1-8) which is a resin of the number (1-8) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 40,000 in terms of polystyrene. The value of the _{M H / (M H + M} P) was 0.95.

<Example 9: Synthesis of resin (1-9)>
As compounds 3-29, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-29).
A 1000 ml flask was charged with 30.0 g of compound 3-29, 300 ml of tetrahydrofuran, and 0.5 g of boron trifluoride diethyl ether complex, and the mixture was purged with nitrogen and then heated to 50 ° C. To this solution, a solution in which 37.8 g of the compound 4-17 was dissolved in 200 ml of tetrahydrofuran was dropped over 30 minutes. After completion of the dropping, the mixture was reacted for 2 hours, and then dropped into 10 L of methanol to precipitate a polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 55.0 g of a resin (1-9) which is a resin of the number (1-9) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 30,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 1.0.
FIG. 5 shows the IR spectrum of the obtained resin (1-9).

<Example 10: Synthesis of resin (1-10)>
8.0 g of the resin (1-9) obtained in Example 9, 100 ml of tetrahydrofuran, 52.0 g of methacrylic acid chloride, and 50.0 of triethylamine are placed in a 500 ml flask, and reacted at room temperature (25 ° C.) for 24 hours. did. After completion of the reaction, the polymer was dropped into 1 L of methanol to precipitate the polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 6.9 g of a resin (1-10) which is a resin of the number (1-10) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 31,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.
FIG. 6 shows the IR spectrum of the obtained resin (1-10).

<Example 11: Synthesis of resin (1-11)>
In place of the compound 3-29, a compound 3-44 represented by the general formula (3), wherein the combination of A ¹ , T ^1, and p is the specific example number (2-44) described above, Instead of the compound 4-17, a compound 4-83 represented by the general formula (4) and having a combination of A ² , T ^2, and q with the specific example number (2-83) described above was used. Except for the above, a resin (1-21) which is a resin with a number (1-21) shown as a specific example of the specific charge transporting resin is obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-21) was used instead of the resin (1-9), the resin of the number (1-11) shown as a specific example of the specific charge transporting resin was used. (1-11) was obtained.
The molecular weight measured by GPC was 35,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 12: Synthesis of resin (1-12)>
In place of the compound 3-29, a compound 3-67 represented by the general formula (3), wherein the combination of A ¹ , T ^1, and p is the specific example number (2-67) described above, Instead of the compound 4-17, a compound 4-86 represented by the general formula (4) and having a combination of A ² , T ² and q of the specific example number (2-86) was used. Except for the above, a resin (1-22) which is a resin of a number (1-22) shown as a specific example of the specific charge-transport resin is obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-22) was used instead of the resin (1-9), the resin of the number (1-12) shown as a specific example of the specific charge transporting resin was used. (1-12) was obtained.
The molecular weight measured by GPC was 45,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 13: Synthesis of resin (1-13)>
Instead of the compound 3-29, a compound 3-92 represented by the general formula (3) and in which the combination of A ¹ , T ^1, and p is the specific example number (2-92) described above, Instead of the compound 4-17, a compound 4-98 represented by the general formula (4) and having a combination of A ² , T ^2, and q with the specific example number (2-98) was used. Except for the above, a resin (1-23) which is a resin of a number (1-23) shown as a specific example of the specific charge-transport resin is obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-23) was used instead of the resin (1-9), the resin of the number (1-13) shown as a specific example of the specific charge transporting resin was used. (1-13) was obtained.
The molecular weight measured by GPC was 46,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 14: Synthesis of resin (1-14)>
In place of the compound 3-29, a compound 3-44 represented by the general formula (3), wherein the combination of A ¹ , T ^1, and p is the specific example number (2-44) described above, Instead of the compound 4-17, a compound 4-57 represented by the general formula (4) and having a combination of A ² , T ² and q of the specific example number (2-57) described above was used. Except for the above, a resin (1-24) which is a resin of a number (1-24) shown as a specific example of the specific charge-transporting resin is obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-24) was used instead of the resin (1-9), the resin of the number (1-14) shown as a specific example of the specific charge transporting resin was used. (1-14) was obtained.
The molecular weight measured by GPC was 28,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 15: Synthesis of resin (1-15)>
In place of the compound 3-29, a compound 3-25 represented by the general formula (3), and in which the combination of A ¹ , T ^1, and p is the specific example number (2-25) described above, Instead of the compound 4-17, a compound 4-44 represented by the general formula (4) and having a combination of A ² , T ² and q of the specific example number (2-44) described above was used. Except for the above, a resin (1-25) which is a resin of a number (1-25) shown as a specific example of the specific charge-transporting resin is obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-25) was used instead of the resin (1-9), the resin of the number (1-15) shown as a specific example of the specific charge transporting resin was used. (1-15) was obtained.
The molecular weight measured by GPC was 50,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 16: Synthesis of resin (1-16)>
In place of the compound 3-29, a compound 3-5 represented by the general formula (3) and in which A ¹ , T ^1, and p are the specific example number (2-5) described above is used, Instead of the compound 4-17, a compound 4-25 represented by the general formula (4) and having a combination of A ² , T ² and q of the specific example number (2-25) described above was used. Except for the above, a resin (1-26) which is a resin of a number (1-26) shown as a specific example of the specific charge-transport resin is obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-26) was used instead of the resin (1-9), the resin of the number (1-16) shown as a specific example of the specific charge transporting resin was used. (1-16) was obtained.
The molecular weight measured by GPC was 30,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 17: Synthesis of resin (1-17)>
In place of the compound 3-29, a compound 3-25 represented by the general formula (3), and in which the combination of A ¹ , T ^1, and p is the specific example number (2-25) described above, Instead of the compound 4-17, a compound 4-92 represented by the general formula (4) and having a combination of A ² , T ^2, and q corresponding to the specific example number (2-92) described above was used. Except for the above, a resin (1-27) which is a resin of a number (1-27) shown as a specific example of the specific charge-transport resin is obtained in the same manner as in Example 9.
Also, in the same manner as in Example 10 except that the resin (1-27) was used instead of the resin (1-9), the resin of the number (1-17) shown as a specific example of the specific charge transporting resin (1-17) was obtained.
The molecular weight measured by GPC was 42,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 18: Synthesis of resin (1-18)>
In place of the compound 3-29, a compound 3-25 represented by the general formula (3), and in which the combination of A ¹ , T ^1, and p is the specific example number (2-25) described above, Instead of the compound 4-17, a compound 4-25 represented by the general formula (4) and having a combination of A ² , T ² and q of the specific example number (2-25) described above was used. Except for the above, a resin (1-28) having a number (1-28) shown as a specific example of the specific charge-transporting resin was obtained in the same manner as in Example 9.
Further, in the same manner as in Example 10 except that the resin (1-28) was used instead of the resin (1-9), the resin of the number (1-18) shown as a specific example of the specific charge transporting resin was used. (1-18) was obtained.
The molecular weight measured by GPC was 38,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 0.

<Example 19: Synthesis of resin (1-19)>
As compounds 3-18, wherein is represented by the general formula (3), and the combination of ^{A 1} and ^{T 1} and p has prepared compound is a preceding example number (2-18).
5.0 g of compound 3-18, 5.5 g of compound 4-17, 100 ml of toluene, and 0.5 g of tetrabutylammonium bromide were placed in a 500 ml flask, and heated and refluxed for 10 hours to react. After completion of the reaction, the polymer was dropped into 1 L of methanol to precipitate the polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 9.1 g of a resin (1-19) which is a resin of the number (1-19) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 38,000 in terms of polystyrene. The value of _MH / ( _MH + _MP ) was 1.0.
FIG. 7 shows the IR spectrum of the obtained resin (1-19).

<Example 20: Synthesis of resin (1-20)>
A 500 ml flask was charged with 8.0 g of the resin (1-19) obtained in Example 19, 100 ml of tetrahydrofuran, 52.0 g of methacrylic acid chloride, and 50.0 of triethylamine, and reacted at room temperature (25 ° C.) for 24 hours. did. After completion of the reaction, the polymer was dropped into 1 L of methanol to precipitate the polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 6.9 g of a resin (1-20) which is a resin of the number (1-20) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 38,000 in terms of polystyrene. Further, the value of _MH / ( _MH + _MP ) was 0.2.
FIG. 8 shows the IR spectrum of the obtained resin (1-20).

<Example 21: Synthesis of resin (1-29)>
10 g of the resin (1-19) obtained in Example 19 was placed in a 300 ml flask, and 14.8 g of a mixture of 4-iodomethylstyrene and 3-iodomethylstyrene (molar ratio 50/50) and 0.1 g of nitrobenzene were added. The mixture was placed in a flask, and 100 ml of tetrahydrofuran was added and dissolved. To this, 4.6 g of sodium t-butoxy was added over 2 hours at room temperature (25 ° C.), and the mixture was reacted at 50 ° C. for 3 hours. After completion of the reaction, 100 ml of toluene was added, washed with dilute hydrochloric acid and then with water, and dropped into 500 ml of methanol to precipitate a polymer. The obtained polymer was sufficiently washed with methanol and dried to obtain 10.5 g of a resin (1-29) which is a resin of the number (1-29) shown as a specific example of the specific charge transporting resin.
The molecular weight measured by GPC was 38,000 in terms of polystyrene. The value of MH / (MH + MP) was 0.

<Reference example>
Hereinafter, as a reference example, an example in which the resin obtained in the example is used for an electrophotographic photosensitive member will be described.

-Reference Example 1: Preparation of Photoconductor 1-
(Preparation of undercoat layer)
100 parts of zinc oxide (average particle diameter: 70 nm, manufactured by Teica: specific surface area: 15 m ² / g) is stirred and mixed with 500 parts of tetrahydrofuran, and 1.3 parts of a silane coupling agent (KBM503: manufactured by Shin-Etsu Chemical Co., Ltd.) is added. And stirred for 2 hours. Thereafter, toluene was distilled off by distillation under reduced pressure, and baking was performed at 120 ° C. for 3 hours to obtain a silane coupling agent surface-treated zinc oxide.
110 parts of the surface-treated zinc oxide was mixed with 500 parts of tetrahydrofuran with stirring, a solution of 1.0 part of alizarin dissolved in 50 parts of tetrahydrofuran was added, and the mixture was stirred at 50 ° C. for 5 hours. Thereafter, the zinc oxide to which alizarin had been applied was filtered off under reduced pressure, and further dried at 60 ° C. under reduced pressure to obtain alizarin-added zinc oxide.
85 parts of methyl ethyl ketone was obtained by mixing 60 parts of this alizarin-added zinc oxide, 13.5 parts of a curing agent (blocked isocyanate, Sumidur 3175, manufactured by Sumitomo Bayern Urethane Co., Ltd.) and 15 parts of a butyral resin (Eslec BM-1, manufactured by Sekisui Chemical Co., Ltd.). 38 parts of a solution dissolved in water and 25 parts of methyl ethyl ketone were mixed and dispersed for 2 hours by a sand mill using 1 mmφ glass beads to obtain a dispersion.
To the obtained dispersion, 0.005 part of dioctyltin dilaurate as a catalyst and 45 parts of silicone resin particles (Tospearl 145, manufactured by Momentive Performance Materials) were added to obtain a coating liquid for an undercoat layer. This coating solution was applied on an aluminum substrate having a diameter of 30 mm, a length of 340 mm and a thickness of 1 mm by a dip coating method, and dried and cured at 170 ° C. for 40 minutes to obtain an undercoat layer having a thickness of 18 μm.

(Preparation of charge generation layer)
The position where the Bragg angle (2θ ± 0.2 °) of the X-ray diffraction spectrum using the Cukα characteristic X-ray as the charge generating substance is at least 7.3 °, 16.0 °, 24.9 °, 28.0 ° A mixture of 15 parts of hydroxygallium phthalocyanine having a diffraction peak, 10 parts of a vinyl chloride / vinyl acetate copolymer resin (VMCH, manufactured by NUC Corporation) as a binder resin, and 200 parts of n-butyl acetate And dispersed in a sand mill for 4 hours using glass beads having a diameter of 1 mmφ. 175 parts of n-butyl acetate and 180 parts of methyl ethyl ketone were added to the obtained dispersion and stirred to obtain a charge generating layer coating liquid. This coating solution for a charge generation layer was applied onto the undercoat layer by dip coating, and dried at normal temperature (20 ° C.) to form a charge generation layer having a thickness of 0.2 μm.

(Preparation of charge transport layer)
10 parts of the resin (1-1) was added to and dissolved in 40 parts of chlorobenzene to obtain a coating solution for a charge transport layer. This coating solution was applied on the charge generation layer by push-up coating, air-dried at room temperature (20 ° C.) for 30 minutes, and dried by heating at 150 ° C. for 1 hour to form a charge transport layer having a thickness of 18 μm. The electrophotographic photoreceptor 1 of Example 1 was produced.

-Reference Example 2: Production of photoconductor 2-
The preparation of the undercoat layer and the preparation of the charge generation layer were performed in the same manner as in Reference Example 1.
10 parts of Resin (1-2) and 0.2 part of OTazo-15 (manufactured by Otsuka Chemical Co., Ltd., molecular weight 354.4) were added to 40 parts of chlorobenzene and dissolved to obtain a coating solution for a charge transport layer. This coating solution was applied on the charge generation layer by push-up coating, air-dried at room temperature (20 ° C.) for 30 minutes, and then heated from room temperature (20 ° C.) at a rate of 10 ° C./min. The mixture was heated to 150 ° C., cured by heating at 150 ° C. for 1 hour, and a charge transport layer having a thickness of 18 μm was formed. Thus, an electrophotographic photosensitive member 2 of Reference Example 2 was produced.

-Reference Examples 3 to 5: Production of Photoconductors 3 to 5-
The electrophotographic photoreceptors of Reference Examples 3 to 5, respectively, in the same manner as Reference Example 2 except that Resins (1-3) to (1-5) were used instead of Resin (1-2). 3 to 5 were produced.

-Reference Example 6: Preparation of Photoconductor 6-
An electrophotographic photoreceptor 6 of Reference Example 6 was produced in the same manner as in Reference Example 1, except that the resin (1-6) was used instead of the resin (1-1).

-Reference Examples 7 and 8: Preparation of Photoconductors 7 and 8-
The electrophotographic photoreceptors of Reference Examples 7 to 8 in the same manner as in Reference Example 2 except that Resins (1-7) to (1-8) were used instead of Resin (1-2). Nos. 7 to 8 were produced.

-Reference Example 9: Preparation of Photoconductor 9-
An electrophotographic photosensitive member 9 of Reference Example 9 was produced in the same manner as in Reference Example 1, except that the resin (1-9) was used instead of the resin (1-1).

-Reference Examples 10 to 18: Production of Photoconductors 10 to 18-
The electrophotographic photoreceptors of Reference Examples 10 to 18 in the same manner as in Reference Example 2 except that Resins (1-10) to (1-18) were used instead of Resin (1-2). 10 to 18 were produced.

-Comparative Reference Example 1: Preparation of photoconductor C1-
In the same manner as in Reference Example 1, except that 4 parts of CTM1 having the following structure and 6 parts of CTB1 (viscosity average molecular weight: 40,000) having the following structure were used instead of 10 parts of the resin (1-1). Thus, a photoreceptor C1 of Comparative Reference Example 1 was produced.

-Evaluation of image quality-
The electrophotographic photosensitive member manufactured as described above was mounted on ApeosPort-IV C4470 manufactured by Fuji Xerox Co., Ltd., and an image forming test was continuously performed on 10,000 sheets at 8 ° C. and 20% RH. The evaluation (specifically, the following ghost, fog, streak, and image deletion) was performed. Further, after the above-mentioned continuous image forming test of 10,000 sheets was performed, the apparatus was allowed to stand in an environment of a temperature of 8 ° C. and a humidity of 20% RH for 24 hours, and further continuously performed the image forming test of 10,000 sheets. The image quality evaluation (image deletion) of the second sheet (20,000 sheets in total) was performed. The evaluation criteria are as follows. Table 1 shows the results.

(Ghost evaluation)
The ghost formed a chart of G and a pattern having a gray area with an image density of 50% shown in FIG. 9A, and visually evaluated the appearance of the letter G in the 50% gray area.
A: Good or slight as shown in FIG.
B: Somewhat noticeable as shown in FIG. 9 (B).
C: It is clearly confirmed as shown in FIG.

(Fog evaluation)
The fog evaluation was performed by visually observing the degree of adhesion of the toner on the white background using the same sample as the above-mentioned ghost evaluation.
A: Good.
B: There is slight fog.
C: There is fog which is a problem in image quality.

(Streak evaluation)
The streak evaluation was visually determined using the same sample as the ghost evaluation described above.
A: Good.
B: Streaks are partially generated.
C: Streak which causes a problem in image quality.

(Image deletion evaluation)
The image deletion was visually determined using the same sample as the ghost evaluation described above.
A: Good.
B: There is no problem in the image evaluation in the continuous image formation test of 10,000 sheets before leaving, but the image deletion occurs in the image evaluation in the continuous 10,000 sheets image formation test after standing for one day (24 hours).
C: Image deletion occurred in image evaluation in a continuous 10,000-sheet image forming test before leaving.

−Evaluation of rise in residual potential−
The residual potential was measured by the following method, and the increase in the residual potential before and after the image forming test was evaluated.
Specifically, a potential sensor was attached to a modified ApeosPort-IV C4470 manufactured by Fuji Xerox Co., Ltd., and the residual potential before the image forming test was measured at 8 ° C. and 20% RH. Then, immediately after the image forming test of 10,000 sheets was performed at 8 ° C. and 20% RH, the residual potential on the surface of the electrophotographic photosensitive member was measured. The difference between the initial potential and the residual potential after the 10,000-sheet image forming test (the residual potential after the 10,000-sheet image forming test minus the initial residual potential) was defined as the increase. Table 1 shows the results.

-Evaluation of the amount of wear of the charge transport layer-
The initial photoreceptor film thickness (ie, the total thickness of the undercoat layer, the charge generation layer, and the charge transport layer) before performing the image forming test for 10,000 sheets continuously before leaving in the evaluation of the image quality, After completion of the image forming test for 10,000 sheets, the thickness of the photoreceptor was measured with an eddy current measuring device (Fisher scope MMS) to evaluate the amount of abrasion. Table 1 shows the results.

  As shown in Table 1 above, the electrophotographic photoreceptor of the reference example has excellent electric characteristics and particularly excellent abrasion resistance, so that the specific charge transporting resin in the examples is useful. I understand.

Claims (11)

A charge transporting resin having a structure represented by the following general formula (1-1) and a structure represented by the following general formula (1-2), and having a weight average molecular weight of 200,000 or less.

(In the general formulas (1-1) and (1-2), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent Represents a linear or branched divalent hydrocarbon group having 1 to 10 carbon atoms, and Y ¹ and Y ² each independently represent a hydrogen atom, a polymerizable functional group, or a group having a polymerizable functional group. And p and q each independently represent 0 or 1. The number of the structures represented by the general formula (1-1) contained in the charge transporting resin is 5 or more, and the charge transporting property is 5 or more. (The number of structures represented by the general formula (1-2) contained in the resin is 5 or more.) The total number of hydroxyl groups contained in the entire charge transport resin and M _H, the total number of polymerizable functional groups contained in the entire charge transporting resins when the M _P, according to claim 1 which satisfies the following formula (A1) Charge transporting resin.
Formula (A1): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.9 Wherein _{M H} and the _{M P} is a charge-transporting resin of claim 2 satisfies the following formula (A2).
Formula (A2): 0 ≦ _MH / ( _MH + _MP ) ≦ 0.6 The polymerizable functional group includes a group represented by the following general formula (P1), a group represented by the following general formula (P2), a group represented by the following general formula (P3), and a group represented by the following general formula (P4). The charge transporting resin according to any one of claims 1 to 3, wherein the charge transporting resin is at least one selected from a group represented by the following general formula (P5) and a group represented by the following general formula (P5).

(In the general formulas (P1) to (P5), R ^{3 to} R ⁶ each independently represent a hydrogen atom, an alkyl group, or an alkoxy group, and * indicates a bonding position.) A ¹ and A ² in the general formulas (1-1) and (1-2) each represent a divalent organic group having a hole transporting ability. 3. The charge transporting resin according to item 1. A ¹ and A ² in the general formula (1-1) and the general formula (1-2) each independently represent a divalent organic group represented by the following general formula (2). The charge transporting resin according to the above.

(In the general formula (2), R ¹ and R ² each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a substituted or unsubstituted aryl group, and X represents a substituted or unsubstituted divalent. Wherein k and m each independently represent 0 or 1.)   The charge transporting resin according to any one of claims 1 to 6, having a weight average molecular weight of 2,000 to 500,000.   The charge transporting resin according to claim 7, wherein the weight average molecular weight is 3,000 or more and 200,000 or less. T ¹ and T ² in the general formulas (1-1) and (1-2) each independently represent a linear or branched divalent hydrocarbon group having 1 to 8 carbon atoms. The charge transporting resin according to claim 1. The charge transport according to any one of claims 1 to 9, comprising a polymerization step of polymerizing a compound represented by the following general formula (3) and a compound represented by the following general formula (4). Production method of conductive resin.

(In the general formulas (3) and (4), A ¹ and A ² each independently represent a divalent organic group having a charge transporting property, and T ¹ and T ² each independently represent a carbon atom of 1 or more and 10 or less. Represents a linear or branched divalent hydrocarbon group, and p and q each independently represent 0 or 1.)   The charge transport property according to claim 10, further comprising an introduction step of introducing a polymerizable functional group into the polymer by reacting a compound having a polymerizable functional group with the polymer obtained in the polymerization step. Method of manufacturing resin.