Resin, resin composition, coating liquid composition, film, coating film, electrophotographic photoreceptor, insulating material, molded article, electronic device, and method for producing resin

Abstract

To provide a resin which is capable of polymer reaction and has an anthracene structure to be a reactive group.SOLUTION: The resin is at least one resin selected from the group consisting of aromatic polycarbonates and polyarylates, and comprises a structure represented by the general formula (DE1) in the figure.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a resin, a resin composition, a coating liquid composition, a film, a coating film, an electrophotographic photoreceptor, an insulating material, a molded article, an electronic device, and a method for producing a resin.

Background Art

[0002] Polycarbonate resins have been used as materials for molded products in various industrial fields because of their excellent mechanical, thermal, and electrical properties. In recent years, polycarbonate resins have also been widely used in the field of functional products that utilize their optical properties and the like. With the expansion of such application fields, the required performance for polycarbonate resins has diversified, and polycarbonate resins having various chemical structures have been proposed, not only the conventionally used polycarbonate resins.

[0003] As an example of a functional product, there is an organic electrophotographic photoreceptor that uses a polycarbonate resin as a binder resin for functional materials such as a charge generation material and a charge transport material. This organic electrophotographic photoreceptor is required to have predetermined sensitivity, electrical characteristics, and optical characteristics according to the electrophotographic process to be applied. Since operations such as corona charging, toner development, transfer to paper, and cleaning treatment are repeatedly performed on the surface of the photosensitive layer of the electrophotographic photoreceptor, an electrical or mechanical external force is applied each time these operations are performed. Therefore, in order to maintain the image quality of electrophotography over a long period of time, the photosensitive layer provided on the surface of the electrophotographic photoreceptor is required to have durability against these external forces. In addition, since an organic electrophotographic photoreceptor is usually produced by dissolving a binder resin together with a functional material in an organic solvent and casting and forming it on a conductive substrate or the like, solubility and stability in the organic solvent are required.

[0004] Conventionally, polycarbonate resins using 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)cyclohexane, etc. as raw materials have been used as binder resins for photoreceptors, but they have not been fully satisfactory in terms of durability. As one of the measures to improve durability, it is conceivable to improve the abrasion resistance of the photosensitive layer. As an effective technique for improving the abrasion resistance of the photosensitive layer, a technique of introducing a reactive functional group into polycarbonate and modifying it by a polymer reaction is known.

[0005] As an example of a polymer reaction, in the resin described in Patent Document 1, a technique of crosslinking a PC having an allyl group using a radical initiator is disclosed, and results showing better mechanical strength (such as tensile strength) than bisphenol A type polycarbonate resin have been obtained.

[0006] Also, Patent Document 2 describes a resin crosslinked by an ionic mechanism such as an epoxy group in a polycarbonate copolymer. Further, Patent Document 3 describes crosslinking by reacting a polycarbonate having a double bond with a compound having a plurality of silicon-hydrogen bonds in the presence of a platinum catalyst, and crosslinking technology by reacting a polycarbonate having a double bond with a compound having an alkoxy group and hydrogen on a silicon atom in the presence of a platinum catalyst, followed by hydrolysis and condensation reaction.

[0007] Also, Patent Document 4 discloses a crosslinking technique by irradiating an electron beam to a polycarbonate having an allyl group while heating it from 120°C to 260°C. Patent Document 5 discloses a method of crosslinking a polycarbonate having an allyl group without a catalyst by heating using a triarylamine having a specific structure and a radical polymerizable compound having no triarylamine structure.

[0008] Patent Document 6 reports a resin in which a resin having an anthracene skeleton at the end of an aliphatic-aromatic polyester is chain-extended with bismaleimide. In addition, Patent Document 7 discloses a crosslinked resin obtained by reacting an aliphatic polyester, polyamide, or polyurea having a furan structure with a polyfunctional maleimide. Patent Document 8 discloses a curable composition in which a polymerizable functional group such as an acrylic group is introduced into an anthracene skeleton, and a crosslinking reaction is carried out at the portion of the functional group. Patent Document 9 discloses a resin obtained by bonding a composition containing a resin such as polyaryl ether sulfone (PAES) containing an anthracene structure and a resin such as PAES having a maleimide structure by a Diels-Alder reaction. Non-Patent Document 1 discloses a resin obtained by crosslinking a resin in which an anthracene dicarboxylic acid skeleton is introduced into a part of an aliphatic-aromatic polyester with a bifunctional maleimide compound.

Prior Art Documents

Patent Documents

[0009]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Patent Document 6

Patent Document 7

Patent Document 8

Patent Document 9

Non-Patent Documents

[0010]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0011] However, in the polycarbonate described in Patent Document 1, there is a problem that the charge transport material (CTM) is deteriorated by using a radical initiator, and the residual potential increases when used as a photoreceptor because the added initiator remains in the photoreceptor.

[0012] In addition, in the polycarbonate described in Patent Document 2, since a compound having a nucleophilic group such as an amino group or an acidic group such as a carboxylic anhydride group is used in the initiation reaction, there is a problem that the CTM is deteriorated and the residual potential increases when used as a photoreceptor because the added compound remains in the photoreceptor. In addition, there is no description confirming that the disclosed resin is crosslinked, and it is unclear whether the disclosed effect of improving physical properties is derived from the crosslinked structure.

[0013] In addition, in the polycarbonate described in Patent Document 3, since a platinum catalyst is used, there is a problem that the CTM is deteriorated and the residual potential increases when used as a photoreceptor because the added catalyst remains in the photoreceptor. In addition, it is difficult to suppress the reaction in the coating solution, and there are problems such as an increase in viscosity and gelation during storage of the coating solution.

[0014] In addition, in the polycarbonate described in Patent Document 4, there is a problem that the CTM is deteriorated when irradiated with an electron beam, and the residual potential increases when used as a photoreceptor.

[0015] As described above, there are also examples in which crosslinked polycarbonate and crosslinked polyarylate can be obtained without including a radical initiator or a reaction catalyst that causes deterioration of electrical properties, and without using UV, electron beams, etc. that alter CTM. As an example of this, Patent Document 5 reports a technique in which a monomer having high radical polymerization activity and undergoing radical polymerization simply by heating without using an initiator or irradiating with UV is used, and a polycarbonate having an allyl group is allowed to coexist therewith. However, since a monomer that undergoes radical polymerization even without an initiator or light irradiation is used, a polymer of the polymerizable monomer alone is mainly produced, and the reaction probability between the polycarbonate having an allyl group with relatively low radical polymerization activity and the polymerizable monomer is considered to be low. Therefore, it is considered that the obtained composition does not have a dense three-dimensional network structure of the polymer, but is a composition in which a cross-linked polymer of a polycarbonate resin and a radical polymerization monomer exists separately and only a part thereof is bonded. And, the effect of improving physical properties due to the increase in molecular weight of the charge transport material, which usually exists as a low molecule, is dominant, and the improvement in physical properties due to cross-linking of the polycarbonate portion is insufficient. In addition, since a highly active compound that allows radical polymerization to proceed even without an initiator is used, it is difficult to suppress the progress of polymerization at the stage of the coating liquid composition, and there are problems such as an increase in viscosity and gelation during storage of the coating liquid.

[0016] As a cross-linking technique that can satisfy these requirements, Patent Document 6 discloses, as an example using a resin other than polycarbonate, a linear polymer by a molecular weight extension reaction of an aliphatic-aromatic polyester by a Diels-Alder reaction. However, Patent Document 6 neither describes nor suggests applying the technique described in Patent Document 6 to an aromatic polycarbonate or an all-aromatic polyester.

[0017] In addition, Patent Document 7 describes an example of crosslinking an aliphatic polyester, polyamide, or polyurea by a Diels-Alder reaction. However, these examples aim to impart solvent resistance by crosslinking a soft aliphatic resin and to obtain an elastomer applicable to a diaphragm seal or an adhesive for the intended use. The technical idea of these examples is different from the idea of the present invention, which further enhances the functionality of an aromatic polycarbonate or wholly aromatic polyester having high mechanical strength through a reaction with a modifying component. Also, Patent Document 7 neither describes nor suggests applying the technology described in Patent Document 7 to an aromatic polycarbonate or wholly aromatic polyester. Non-Patent Document 1 describes an example of introducing an anthracene dicarboxylic acid skeleton into polyethylene terephthalate (PET) and crosslinking it with a bifunctional maleimide compound. The purpose of this example is similar to that of the present invention in terms of improving mechanical properties by heat crosslinking. However, Non-Patent Document 1 neither describes nor suggests an example of applying it to a polycarbonate or polyarylate. In addition, considering its use in an electrophotographic photoreceptor, PET has low solubility in organic solvents such as THF, which are usually used as coating solvents, and poor compatibility with charge transport materials such as triarylamine, and thus cannot be used for this purpose.

[0018] Patent Document 8 discloses an example of introducing a polymerizable functional group such as an acrylic group into an anthracene skeleton and performing a crosslinking reaction at the portion of the functional group. However, Patent Document 8 neither describes nor suggests using the anthracene portion for a crosslinking reaction. In addition, the invention described in Patent Document 8 aims to retain the function of the anthracene skeleton, and the technology of the present invention applying a Diels-Alder reaction that causes the anthracene skeleton to disappear by the reaction is contrary to this purpose. Patent Document 9 shows an example in which a PAES having an anthracene skeleton reacts with a PAES having a maleimide terminal to increase the molecular weight. The claims also disclose that it is applicable to polycarbonate. However, the specific structure of the polycarbonate is not shown, and a polycarbonate having an amino group is required to apply the exemplified method. The synthesis of a polycarbonate having an amino group: (i) Since the amino group acts as a trifunctional reactive group, a gel is formed by generating a multi-branched structure in the polymerization process. (ii) During the polymerization process, the hydrophilic amino terminal acts similarly to a surfactant, significantly deteriorating the liquid separation of the organic layer and the aqueous layer in the washing process during production. For the above reasons, it is considered difficult, and it cannot be said that the invention can be sufficiently implemented even with polycarbonate, nor can it be said that the invention is sufficiently disclosed.

[0019] The first object of the present invention is to provide a resin having an anthracene structure that can undergo a polymer reaction and serves as a reactive group. The second object of the present invention is to polymer-react without including a radical initiator or reaction catalyst that causes deterioration of electrical properties, and without using UV or electron beams that alter the charge transport material (CTM), thereby enabling cross-linking, polymer elongation, grafting, loading of functional components, synthesis of block copolymers of different polymers, or a polymer brush, etc. It is to provide at least one of an aromatic polycarbonate and a polyarylate resin having an anthracene structure, which is a reactive group applicable to various purposes. The third object of the present invention is to provide a resin composition and a coating liquid composition having the characteristic of less characteristic change because the reaction at the stage of the coating liquid composition hardly occurs. Further, the fourth object of the present invention is to provide an electrophotographic photoreceptor that is excellent in solvent resistance and abrasion resistance, hardly undergoes mechanical deterioration, and has no deterioration of residual potential by including the above resin.

Means for Solving the Problems

[0020] According to one aspect of the present invention, there is provided at least one resin selected from the group consisting of an aromatic polycarbonate and a polyarylate, wherein the resin has a component having a specific anthracene structure.

[0021] According to one aspect of the present invention, there is provided a resin composition containing the resin according to one aspect of the present invention described above.

[0022] According to one aspect of the present invention, there is provided a coating liquid composition containing the resin composition according to one aspect of the present invention described above and an organic solvent.

[0023] According to one aspect of the present invention, there is provided an electrophotographic photoreceptor having a layer containing the resin according to one aspect of the present invention described above.

[0024] According to one aspect of the present invention, there is provided a molded article containing the resin according to one aspect of the present invention described above.

[0025] According to one aspect of the present invention, there is provided a film containing the resin according to one aspect of the present invention described above.

[0026] According to one aspect of the present invention, there is provided a coating film containing the resin according to one aspect of the present invention described above.

[0027] According to one aspect of the present invention, there is provided an insulating material containing the resin according to one aspect of the present invention described above.

[0028] According to one aspect of the present invention, there is provided an electronic device containing the resin according to one aspect of the present invention described above.

[0029] According to one aspect of the present invention, there is provided a method for producing a resin, which includes a step of performing a polymer reaction of the resin composition by heating the resin composition according to one aspect of the present invention described above.

Advantages of the Invention

[0030] According to one aspect of the present invention, a resin having an anthracene structure that can undergo a polymer reaction and serve as a reactive group can be provided. According to one aspect of the present invention, in at least one of the resins of aromatic polycarbonate and polyarylate, it does not contain a radical initiator or a reaction catalyst that causes deterioration of electrical properties, and can be manufactured without using UV or an electron beam that alters a charge transport material (CTM), and a resin having a novel structure that substantially does not contain a homopolymer of a polymerizable component can be provided. Further, according to one aspect of the present invention, a resin composition and a coating liquid composition having a characteristic of less characteristic change due to the reaction being unlikely to occur at the stage of the coating liquid composition can be provided. Further, according to one aspect of the present invention, by including the resin, an electrophotographic photoreceptor excellent in solvent resistance, excellent in abrasion resistance, unlikely to undergo mechanical deterioration, and having no deterioration of residual potential can be provided.

Brief Description of the Drawings

[0031]

Figure 1

Figure 2

Figure 3

Embodiments for Carrying Out the Invention

[0032] [Resin] The resin according to the present embodiment is at least one resin selected from the group consisting of aromatic polycarbonate and polyarylate. Specific resins include aromatic polycarbonate, polyarylate, and an aromatic polycarbonate-polyarylate copolymer (hereinafter, these are also simply referred to as "PCs").

[0033] The resin according to this embodiment exhibits the property of causing a polymer reaction by the Diels-Alder reaction. When a polymer reaction occurs, among the structures represented by the general formula (DE1) described later, the anthracene structure becomes a reactive group. The resin having the structure represented by the general formula (DE1) and obtained by polymer reaction has the structure represented by the following general formula (S1). In the following general formula (S1), * represents the bonding position.

[0034] [Chemical formula]

[0035] The resin according to this embodiment can be applied to various purposes (such as crosslinking, grafting, polymer brushes, loading of functional components, block copolymerization of different polymers, and molecular chain extension, etc.) by the polymer reaction by the Diels-Alder reaction. And the structure of the crosslinking site that binds between polymer chains becomes a bonding mode as shown by the following general formula (P1), for example.

[0036] [Chemical formula]

[0037] In the above general formula (P1), *PC represents the polymer chain of PCs. The elliptical part represents crosslinking, grafting, resin brushes, loading of functional components, molecular weight extension, etc. The elliptical part shown by the general formula (P1) may be any of crosslinking, graft polymer synthesis, resin brushes, loading of functional components, molecular chain extension, synthesis of block copolymers with different polymers, etc., and can be appropriately selected according to the purpose. In Patent Document 9, anthracene, which is a reactive group, is introduced by a high molecular weight reaction. However, the reaction yield is as low as about 22%, resulting in a structure where "high molecular weight by reaction" hardly occurs. The reason is that for high molecular weight formation, "both ends need to react". However, even when the anthracene end reacts, the end on the opposite side of the molecule is likely to be an end other than anthracene, which accounts for 78%, and in most cases, a single molecule will stop after binding to a maleimide group. Therefore, an efficient introduction method with an efficiency close to 100% for the anthracene structure is required. In contrast, the resin according to this embodiment can improve the reaction yield by having a specific anthracene structure. The inventors of the present invention have conducted intensive research to solve the above-described problems of the present invention. As a result, it has been found that PCs that undergo a polymer reaction by the Diels - Alder reaction have excellent solution stability, react at the current photoreceptor manufacturing process temperature, and no deterioration in the electrical properties of the obtained resin is observed. The present invention has been completed based on such findings.

[0038] The resin according to this embodiment is a polymer having a specific anthracene structure with Diels - Alder reactivity, that is, a structure represented by the following general formula (DE1).

[0039]

Chemical formula

[0040] In the general formula (DE1), R is, independently of each other, an aliphatic hydrocarbon group having 1 or more and 12 or less carbon atoms, an aromatic hydrocarbon group having 6 or more and 12 or less ring - forming carbon atoms, an alkoxy group having 1 or more and 10 or less carbon atoms, or a halogen atom. Also, a cyclic structure (including an aromatic ring and a heterocyclic ring) formed by linking a plurality of Rs may be formed. Also, when there are a plurality of Rs, the Rs may be the same or different. n represents an integer of 0 or more and 4 or less, m represents an integer of 0 or more and 9 or less.

[0041] In the general formula (DE1), the aliphatic hydrocarbon group having 1 or more and 12 or less carbon atoms represented by R includes a saturated or unsaturated aliphatic hydrocarbon group (alkyl group, alkenyl group, alkynyl group). Examples of the alkyl group as the aliphatic hydrocarbon group having 1 or more and 12 or less carbon atoms include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. Examples of the alkenyl group as the aliphatic hydrocarbon group having 1 or more and 12 or less carbon atoms include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 1-butenyl group, a 1-hexenyl group, an octenyl group, a decenyl group, and a dodecenyl group. Examples of the alkynyl group as the aliphatic hydrocarbon group having 1 or more and 12 or less carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 3-hexynyl group, an octynyl group, a decynyl group, and a dodecynyl group.

[0042] In the general formula (DE1), the aromatic hydrocarbon group having 6 or more and 12 or less ring-forming carbon atoms represented by R includes, for example, a phenyl group, a naphthyl group, and a biphenyl group.

[0043] In the general formula (DE1), the alkoxy group having 1 to 10 carbon atoms represented by R includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an isopentyloxy group, a neopentyloxy group, a tert-pentyloxy group, an isohexyloxy group, a sec-hexyloxy group, a tert-hexyloxy group, an isoheptyloxy group, a sec-heptyloxy group, a tert-heptyloxy group, an isooctyloxy group, a sec-octyloxy group, a tert-octyloxy group, an isononyloxy group, a sec-nonyloxy group, a tert-nonyloxy group, an isodecyloxy group, a sec-decyloxy group, and a tert-decyloxy group, etc.

[0044] In the general formula (DE1), the halogen atom represented by R includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, etc.

[0045] As the dienophile structure to be subjected to a polymer reaction with the resin according to the present embodiment, any structure that can cause a Diels-Alder reaction can be applied, but due to its high reactivity, those having a maleimide skeleton are preferably used. Examples of dienophile structures include 4,4'-diphenylmethanebismaleimide, m-phenylenebismaleimide, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyl ether bismaleimide, 4,4'-diphenyl sulfone bismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, diphenylmethane-4,4'-bismaleimide polymer having 4,4'-methylenedianiline, N,N'-(2,2'-diethyl-6,6'-dimethylene diphenylene)bismaleimide, N,N'-(4-methyl-m-phenylene)bismaleimide, N,N'-m-phenylenedimaleimide, N,N'-m-phenylenebismaleimide, bismaleimides such as polyphenylmethanebismaleimide, monomer maleimides such as N-phenylmaleimide, and PCs having a structure in which the molecular terminals are terminated with the following compounds.

[0046]

Chemical formula

[0047] In the present embodiment, the dienophile structure or dienophile group (hereinafter, these are also simply referred to as "dienophile") preferably includes a structure represented by the following general formula (DP1).

[0048]

Chemical formula

[0049] In the general formula (DP1), X2 is a single bond or a linking group with another skeleton, X2 as the linking group contains at least any one atom selected from the group consisting of a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom, and the bonding modes between the atoms constituting the linking group are all covalent bonds. * indicates the bonding position.

[0050] In the present embodiment, it is particularly preferable that the dienophile structure or the dienophile group contains a structure represented by the following general formula (DP2). In the following general formula (DP2), * indicates the bonding position.

[0051] [Chemical formula]

[0052] When imparting functions by a polymer reaction in the present embodiment, the ratio of anthracene to the dienophile can be appropriately set according to the target physical properties and the intended use. The molar ratio of anthracene to the dienophile (anthracene / dienophile) is preferably 0.01 or more and 100 or less, more preferably 0.1 or more and 10 or less, still more preferably 0.2 or more and 5 or less, and particularly preferably 0.5 or more and 1.5 or less. When the molar ratio of anthracene to the dienophile is less than 0.01 or exceeds 100, since the structure introduced by the polymer reaction is small, there is a possibility that a sufficient modification effect cannot be obtained.

[0053] The resin according to the present embodiment preferably contains at least any one of the structures represented by the following general formula (UN1) and general formula (UN2).

[0054] [Chemical formula]

[0055] In the general formula (UN1) and the general formula (UN2), Ar3, Ar 31 and Ar 32Each is independently a group represented by the following general formula (UN11). * indicates the bonding position.

[0056]

Chemical formula

[0057] In the general formula (UN11), m3 is 0, 1 or 2, n3 is 4, A plurality of R3s are each independently a hydrogen atom, a halogen atom, an alkyl having 1 to 10 carbon atoms, an aryl having 6 to 12 ring-forming carbon atoms, or a fluorinated alkyl having 1 to 10 carbon atoms, and when there are a plurality of R3s, they may be the same or different. X3s are each independently a single bond, -C(-R 31 )2-, -O-, -S-, -SO-, -SO2-, -N(-R 32 )-, -P(-R 33 )-, -P=O(-R 34 )-, carbonyl, ester, amide, an alkylene having 2 to 20 carbon atoms, an alkylidene having 2 to 20 carbon atoms, a cycloalkylene having 3 to 20 ring-forming carbon atoms, a cycloalkylidene having 3 to 20 ring-forming carbon atoms, an arylene having 6 to 20 ring-forming carbon atoms, a bicycloalkanediyl having 4 to 20 ring-forming carbon atoms, A tricycloalkanediyl having 5 to 20 ring-forming carbon atoms, a bicycloalkylidene having 4 to 20 ring-forming carbon atoms, and a group consisting of one or more selected from the group consisting of tricycloalkylidenes having 5 to 20 ring-forming carbon atoms, R 31 to R 34 are each independently a hydrogen atom, a halogen atom, an alkyl having 1 to 10 carbon atoms, an aryl having 6 to 12 ring-forming carbon atoms, or a fluorinated alkyl having 1 to 10 carbon atoms. * indicates the bonding position.

[0058] In the general formula (UN11), examples of the halogen atom represented by R3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0059] In the general formula (UN11), examples of the alkyl having 1 to 10 carbon atoms represented by R3 include groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl, sec-hexyl, tert-hexyl, isoheptyl, sec-heptyl, tert-heptyl, isooctyl, sec-octyl, tert-octyl, isononyl, sec-nonyl, tert-nonyl, isodecyl, sec-decyl, and tert-decyl.

[0060] In the general formula (UN11), examples of the aryl having 6 to 12 ring-forming carbon atoms represented by R3 include groups such as phenyl, naphthyl, and biphenyl.

[0061] In the general formula (UN11), the alkyl fluoride having 1 to 10 carbon atoms represented by R3 includes, for example, an alkyl group in which at least one hydrogen atom of the alkyl group exemplified by the alkyl having 1 to 10 carbon atoms represented by R3 in the general formula (UN11) described above is substituted with a fluorine atom.

[0062] In the general formula (UN11), the alkylene having 2 to 20 carbon atoms represented by X3 includes a linear or branched alkylene group, and examples thereof include groups such as ethylene, propylene, isopropylene, butylene, hexylene, octylene, and decylene. In the general formula (UN11), the alkylidene having 2 to 20 carbon atoms represented by X3 includes groups such as ethylidene, propylidene, butylidene, hexylidene, octylidene, decylidene, pentadecylidene, and icosylidene. In the general formula (UN11), the cycloalkylene having 3 to 20 carbon atoms represented by X3 includes a linear or branched alkylene group, and examples thereof include groups such as cyclopropylene, cyclobutylene, cyclohexylene, cyclooctylene, cyclodecylene, cyclododecylene, cyclopentadecylene, and cyclicosylene. In the general formula (UN11), the cycloalkylidene having 3 to 20 carbon atoms represented by X3 includes groups such as cyclopropylidene, cyclobutylidene, cyclohexylidene, cyclooctylidene, cyclodecylidene, cyclododecylidene, cyclopentadecylidene, and cyclicosylidene. In the general formula (UN11), the arylene having 6 to 20 ring-forming carbon atoms represented by X3 includes groups such as phenylene, naphthylene, and biphenylene.

[0063] In the general formula (UN11), the bicycloalkanediyl having 4 to 20 ring-forming carbon atoms represented by X3 is exemplified by, for example, a bicyclic compound of the above-mentioned cycloalkylene, and the tricycloalkanediyl having 5 to 20 ring-forming carbon atoms is exemplified by a tricyclic compound of the above-mentioned cycloalkylene, such as adamantanediyl and tricyclodecanediyl. In the general formula (UN11), the bicycloalkylidene having 4 or more and 20 or less ring-forming carbon atoms represented by X3 is exemplified by the bicyclic compounds of the cycloalkylidene described above, and the tricycloalkylidene having 5 or more and 20 or less ring-forming carbon atoms is exemplified by the tricyclic compounds of the cycloalkylidene described above, such as adamantylidene and tricyclodecylidene.

[0064] In the general formula (UN11), R of X3 31 to R 34 The halogen atom, alkyl having 1 or more and 10 or less carbon atoms, aryl having 6 or more and 12 or less ring-forming carbon atoms, and alkyl fluoride having 1 or more and 10 or less carbon atoms represented by are exemplified by the same groups as those represented by R3 in the general formula (UN11) described above.

[0065] [Method for producing a resin obtained by a polymer reaction] In the resin of the present embodiment, the method for producing a resin obtained by a polymer reaction includes a step of performing a polymer reaction of the resin composition by heating the resin composition according to the present embodiment described below. In the step of performing the polymer reaction of the resin composition, the heating temperature may be determined according to the intended properties, uses, etc. The heating temperature for performing the polymer reaction may be, for example, 60°C or higher and 250°C or lower. The method for producing a resin obtained by a polymer reaction may be a method including a step of applying a coating liquid composition described below to an object by a wet forming method, a step of removing an organic solvent in the coating liquid composition by heating, and a step of performing a polymer reaction of the resin composition in the coating liquid composition by heating simultaneously or subsequently with the heating in the step of removing the organic solvent. Further, a method of modifying a resin by a polymer reaction in advance and obtaining a molded article using the obtained resin may also be used.

[0066] [Resin composition] The resin composition according to the present embodiment includes the resin according to the present embodiment described above. That is, the resin composition according to the present embodiment includes a resin having a specific anthracene structure and a compound or resin containing a dienophile structure. The resin composition according to the present embodiment may be capable of producing the resin according to the present embodiment obtained by a polymer reaction. That is, the resin composition according to the present embodiment may contain, in combination, a polymer having a specific anthracene structure having Diels-Alder reactivity in the structure, and a reactant or polymer having a dienophile group or dienophile structure. Further, the resin composition according to the present embodiment may contain a polymer having a specific anthracene structure having Diels-Alder reactivity and a dienophile structure before the polymer reaction. When a single polymer has a specific anthracene structure and a dienophile structure, the dienophile structure in the molecule serves as a reactant having a dienophile structure.

[0067] Further, the resin composition according to the present embodiment may contain a resin after the polymer reaction of a polymer having a specific anthracene structure and a reactant having a dienophile structure.

[0068] In the resin composition according to the present embodiment, the ratios of anthracene, dienophile, and anthracene and dienophile are the same as those of the resin according to the present embodiment.

[0069] In addition, the concentrations of anthracene and dienophile in the resin composition according to the present embodiment can be appropriately set according to the target physical properties and intended uses. When the number of moles of anthracene is taken as the functional group concentration with respect to the total amount of the composition having the Diels - Alder reactive group, this functional group concentration is preferably 0.01 mmol / g or more and 10 mmol / g or less, more preferably 0.03 mmol / g or more and 7 mmol / g or less, still more preferably 0.1 mmol / g or more and 5 mmol / g or less, even more preferably 0.3 mmol / g or more and 5 mmol / g or less, and particularly preferably 0.5 mmol / g or more and 2 mmol / g or less. When the functional group concentration is less than 0.01 mmol / g, the modification effect by the polymer reaction may be insufficient. When the functional group concentration exceeds 10 mmol / g, since the proportion of the terminal - type anthracene structure is too large, a decrease in mechanical strength due to a low molecular weight occurs, which is not preferable.

[0070] Examples of the resin composition according to the present embodiment include the following components (i) to (iii). (i) A polymer having a structure represented by the general formula (DE1) in the polymer chain and a compound having a dienophile group (ii) A polymer having a structure represented by the general formula (DE1) in the polymer chain and a polymer having a dienophile structure in the polymer chain (iii) A polymer having both a structure represented by the general formula (DE1) and a dienophile structure in one polymer chain

[0071] In the case of the composition containing the component (i), at least either the total number of the structures represented by the general formula (DE1) present at the terminals of the polymer or the number of dienophile groups present in the compound having a difunctional or higher dienophile structure may be a number exceeding 2. Also, at this time, one structure represented by the general formula (DE1) may be provided at each of both terminals of the polymer chain.

[0072] For example, in the case of a composition containing the component (ii), in a polymer having a structure represented by one or more of the general formulas (DE1), the structure represented by the general formula (DE1) is bonded to at least one of one end and the other end of the polymer chain, and in a polymer having two or more dienophile structures, a dienophile structure may be bonded to at least one of one end and the other end of the polymer chain. Further, at least one of the total number of the structures represented by the general formula (DE1) present in the main chain and the ends of the polymer, and the total number of dienophile groups present in the main chain and the ends of the polymer having a dienophile structure may be a number exceeding 2.

[0073] The bond between polymer chains that can be formed by reacting the composition containing the component (ii) can be formed, for example, by reactions of the following combinations.

[0074] (ii-1) A polymer having two dienophile structures, wherein each end of the polymer chain has one of the dienophile structures, and a polymer having one or more structures represented by the general formula (DE1) in the polymer chain (at this time, each end of the polymer chain may have one structure represented by the general formula (DE1)).

[0075] (ii-2) A polymer having two dienophile structures, wherein one end of the polymer chain has one dienophile structure, the other end has no dienophile structure, and the main chain has one dienophile structure, and a polymer having one or more structures represented by the general formula (DE1) in the polymer chain (at this time, each end of the polymer chain may have one structure represented by the general formula (DE1)).

[0076] (ii-3) A polymer having one or more dienophile structures, and Reaction of a polymer having one or more structures represented by the general formula (DE1) above with a polymer (at this time, the polymer may have one structure represented by the general formula (DE1) at each of both ends of the polymer chain).

[0077] Next, the polycarbonate polymer according to the present embodiment will be described. The first form of the polycarbonate polymer (hereinafter also referred to as a PC polymer) according to the present embodiment has at least a repeating unit selected from the repeating unit A represented by the following general formula (1) and the repeating unit B represented by the following general formula (2), and is obtained using at least any one of the bischloroformate oligomers represented by the following general formula (1A), the bischloroformate oligomers represented by the following general formula (2A), and the bischloroformate oligomers represented by the following general formula (2C) as a raw material. Note that the raw material used in the present embodiment is not limited to the raw material used in this first form. For example, a bischloroformate oligomer represented by the following general formula (2A) having a repeating unit selected from the repeating units B represented by the following general formula (2) may be used as a raw material.

[0078]

Chemical formula

[0079]

Chemical formula

[0080] In the general formula (1) and the general formula (1A), Ar 33 is a group represented by the general formula (UN11), and n 31 represents the average degree of polymerization. Also, the average degree of polymerization n 31 is 1.0 or more and 10 or less. In the general formula (2) and the general formula (2A), Ar 34 is a group represented by the general formula (UN11), and n 32 represents the average degree of polymerization. Also, the average degree of polymerization n 32 is 1.0 or more and 10 or less. In the general formula (2C), Ar 33 is a group represented by the general formula (UN11), and Ar 34 is a group represented by the general formula (UN11). Also, n 33 and n 34 each represent the average degree of polymerization. Also, the sum of the average degrees of polymerization n 33 and n 34 is 1.0 or more and 10 or less. * indicates the bonding position. However, Ar 33 and Ar 34 are different from each other. In the general formula (2C), each repeating unit does not necessarily have to be continuous. Examples of the method for calculating the average degree of polymerization include the method described in the examples below.

[0081] As the PC polymer having the repeating unit A alone represented by the general formula (1) and the PC polymer having the repeating unit A represented by the general formula (1) and the repeating unit B represented by the general formula (2), those represented by the following general formula (100) are preferable.

[0082]

Chemical formula

[0083] In the general formula (100), a represents the molar copolymerization ratio in the repeating unit A, and b represents the molar copolymerization ratio in the repeating unit B. a is [Ar 33 / ([Ar 33 +[Ar 34 ), and b is [Ar 34 / ([Ar 33 +[Ar 34 ), including the case where b is 0. [Ar 33 represents the number of moles of the repeating unit A containing the group represented by Ar 33 in the PC polymer, and [Ar 34 represents the number of moles of the repeating unit B containing the group represented by Ar 34 in the PC polymer.

[0084] In the general formula (100), each repeating unit is not necessarily continuous. The PC polymer represented by the general formula (100) may be any of a block copolymer, an alternating copolymer, a random copolymer, and the like. In the first form of the PC polymer according to the present embodiment, as the chain end of the above-described PC polymer, it has a structure represented by the general formula (DE1). Therefore, it becomes a polymer having a conjugated diene structure in the polymer chain.

[0085] The chain end of the PC polymer according to the present embodiment may be sealed with a monovalent aromatic group or a monovalent fluorine-containing aliphatic group within a range satisfying the requirements of the present application, in addition to the above specific end groups. The monovalent aromatic group may be a group containing an aliphatic group. The monovalent fluorine-containing aliphatic group may be a group containing an aromatic group. Further, at least one substituent selected from the group consisting of an alkyl group, a halogen atom, and an aryl group may be added to the monovalent aromatic group and the monovalent fluorine-containing aliphatic group. At least one substituent selected from the group consisting of an alkyl group, a halogen atom, and an aryl group may be further added to these substituents. When there are a plurality of substituents, these substituents may be bonded to each other to form a ring.

[0086] The monovalent aromatic group constituting the chain end preferably includes an aryl group having 6 to 12 ring-forming carbon atoms. Examples of such an aryl group include a phenyl group and a biphenyl group. Examples of the substituent added to the aromatic group and the substituent added to the alkyl group added to the aromatic group include halogen atoms such as a fluorine atom, a chlorine atom, and a bromine atom. Examples of the substituent added to the aromatic group also include an alkyl group having 1 to 20 carbon atoms. This alkyl group may be a group to which a halogen atom is added as described above, or a group to which an aryl group is added.

[0087] Examples of the monovalent fluorine-containing aliphatic group constituting the chain end include monovalent groups derived from fluorine-containing alcohols.

[0088] As the fluorine-containing alcohol, it is preferable that a plurality of fluoroalkyl chains having 2 to 6 carbon atoms are linked via an ether bond and the total number of fluorine atoms is 13 to 19. If the total number of fluorine atoms is 13 or more, sufficient water repellency and oil repellency can be exhibited. On the other hand, if the total number of fluorine atoms is 19 or less, a decrease in reactivity during polymerization can be suppressed, and at least one of the mechanical strength, surface hardness, and heat resistance of the obtained PC polymer can be improved. Furthermore, as the monovalent fluorine-containing aliphatic group, a monovalent group derived from a fluorine-containing alcohol having two or more ether bonds is also preferable. By using such a fluorine-containing alcohol, the dispersibility of the PC polymer in the coating liquid composition is improved, the abrasion resistance in the molded body and the electrophotographic photoreceptor is improved, and the surface lubricity, water repellency, and oil repellency after abrasion can be maintained.

[0089] Alternatively, as the fluorine-containing alcohol, a fluorine-containing alcohol represented by the following general formula (30) or (31), a fluorine-containing alcohol such as 1,1,1,3,3,3-hexafluoro-2-propanol, or a fluorine-containing alcohol via an ether bond represented by the following general formula (32), (33), or (34) is also preferable.

[0090] H(CF2) n1 CH2OH···(30) F(CF2) m1 CH2OH···(31)

[0091] In the general formula (30), n1 is an integer from 1 to 12, and in the general formula (31), m1 is an integer from 1 to 12.

[0092] F-(CF2) n 31 -OCF2CH2-OH···(32) F-(CF2CF2) n 32 -(CF2CF2O) n 33 -CF2CH2OH···(33) CR3-(CF2) n 35 -O-(CF2CF2O) n 34 -CF2CH2OH···(34)

[0093] In the general formula (32), n 31 is an integer from 1 to 10, preferably an integer from 5 to 8. In the general formula (33), n 32 is an integer from 0 to 5, preferably an integer from 0 to 3. n 33 is an integer from 1 to 5, preferably an integer from 1 to 3. In the general formula (34), n 34 is an integer from 1 to 5, preferably an integer from 1 to 3. n 35 is an integer from 0 to 5, preferably an integer from 0 to 3. R is CF3 or F.

[0094] In this embodiment, from the viewpoint of improving electrical properties and wear resistance, the chain ends of the PC polymer are preferably blocked by a monovalent group derived from a phenol represented by the following general formula (35) or a monovalent group derived from a fluorine-containing alcohol represented by the following general formula (36).

[0095]

Chemical formula

[0096] In the general formula (35), R 30 represents an alkyl group having 1 to 10 carbon atoms or a fluoroalkyl group having 1 to 10 carbon atoms, and p is an integer from 1 to 3. In the general formula (36), R frepresents a perfluoroalkyl group having 5 or more carbon atoms and 11 or more fluorine atoms, or a perfluoroalkyloxy group represented by the following general formula (37).

[0097] [Chemical formula]

[0098] In the general formula (37), R f2 is a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms. mx is an integer from 1 to 3.

[0099] As one aspect of the method for producing a PC polymer according to this embodiment, there is a production method in which at least one of the bischloroformate oligomer compound represented by the general formula (1A) and the bischloroformate oligomer compound represented by the general formula (2A), an organic solvent, an aqueous alkali solution, and a monomer such as a bisphenol compound are used, and the organic layer and the aqueous layer are mixed to carry out an interfacial polycondensation reaction.

[0100] In the method for producing a PC polymer according to this embodiment, as a terminal capping agent for generating a chain end, a monovalent carboxylic acid and its derivatives, or a monovalent phenol can be used. For example, p-tert-butyl-phenol, p-phenylphenol, p-cumylphenol, p-perfluorononylphenol, p-(perfluorononylphenyl)phenol, p-(perfluorohexyl)phenol, p-tert-perfluorobutylphenol, p-perfluorooctylphenol, 1-(p-hydroxybenzyl)perfluorodecane, p-[2-(1H,1H-perfluorotridecyloxy)-1,1,1,3,3,3-hexafluoropropyl]phenol, 3,5-bis(perfluorohexyloxycarbonyl)phenol, p-hydroxybenzoic acid perfluorododecyl, p-(1H,1H-perfluorooctyloxy)phenol, 2H,2H,9H-perfluorononanoic acid, etc. are preferably used.

[0101] Alternatively, as the end-capping agent for generating the chain ends, a fluorine-containing alcohol represented by the general formula (30) or (31), or a monovalent fluorine-containing alcohol such as 1,1,1,3,3,3-hexafluoro-2-propanol is also preferably used. Further, as the end-capping agent for generating the chain ends, it is also preferable to use a fluorine-containing alcohol via an ether bond represented by the general formula (32), (33), or (34).

[0102] Among these, as the end-capping agent for generating the chain ends, from the viewpoint of improving electrical properties and wear resistance, it is preferable to use a monovalent phenol represented by the general formula (35) or a monovalent fluorine-containing alcohol represented by the general formula (36).

[0103] As the monovalent phenol represented by the general formula (35), for example, p-tert-butyl-phenol, p-perfluorononylphenol, p-perfluorohexylphenol, p-tert-perfluorobutylphenol, p-perfluorooctylphenol, etc. are preferably used. That is, in the present embodiment, it is preferable that the chain ends are sealed with an end-capping agent selected from the group consisting of p-tert-butyl-phenol, p-perfluorononylphenol, p-perfluorohexylphenol, p-tert-perfluorobutylphenol, and p-perfluorooctylphenol.

[0104] Examples of the fluorine-containing alcohol via an ether bond represented by the general formula (36) include the following compounds. That is, it is also preferable that the chain ends in the present embodiment are sealed with an end-capping agent selected from any of the following fluorine-containing alcohols.

[0105]

Chemical formula

[0106] The addition ratio of the end-capping agent changes in conjunction with the concentration of the crosslinkable reactive group and the molecular weight according to the fraction at the end. It is preferably 0.1 mol% or more and 67 mol% or less, more preferably 0.5 mol% or more and 50 mol% or less, as the molar percentage of the copolymer composition of the structure represented by the general formula (DE1) with respect to the total of the main chain and the repeating units at the end. When the addition ratio of the end-capping agent is 67 mol% or less, a decrease in mechanical strength can be suppressed, and when it is 0.1 mol% or more, the effect of improving properties by crosslinking can be obtained. The ratio of the structure represented by the general formula (DE1) in all the ends of the resin according to this embodiment is 50% or more in molar ratio, preferably 70% or more, more preferably 80% or more, even more preferably 90% or more, and particularly preferably 95% or more. By this ratio being 50% or more, the modification effect by the polymer reaction can be efficiently exhibited.

[0107] In addition, the branching agent that can be used in the method for producing a PC polymer according to this embodiment is not particularly limited. Specific examples of the branching agent include phloroglucinol, pyrogallol, 4,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-2-heptene, 2,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-3-heptene, 2,4-dimethyl-2,4,6-tris(4-hydroxyphenyl)heptane, 1,3,5-tris(2-hydroxyphenyl)benzene, 1,3,5-tris(4-hydroxyphenyl)benzene, 1,1,1-tris(4-hydroxyphenyl)ethane, tris(4-hydroxyphenyl)phenylmethane, 2,2-bis[4,4-bis(4-hydroxyphenyl)cyclohexyl]propane, 2,4-bis[2-bis(4-hydroxyphenyl)-2-propyl]phenol, 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol, 2-(4-hydroxyphenyl)-2-(2,4-dihydroxyphenyl)propane, tetrakis(4-hydroxyphenyl)methane, tetrakis[4-(4-hydroxyphenylisopropyl)phenoxy]methane, 2,4-dihydroxybenzoic acid, trimesic acid, cyanuric acid, 3,3-bis(3-methyl-4-hydroxyphenyl)-2-oxo-2,3-dihydroindole, 3,3-bis(4-hydroxyaryl)oxindole, 5-chloro isatin, 5,7-dichloro isatin, 5-bromo isatin, and the like. The addition ratio of these branching agents is preferably 30 mol% or less, more preferably 5 mol% or less, in terms of the molar percentages of the repeating unit A, the repeating unit B, and the copolymer composition at the chain ends, or in terms of the molar percentages of the repeating unit A and the copolymer composition at the chain ends. When the addition ratio of the branching agent is 30 mol% or less, a decrease in moldability can be suppressed.

[0108] When performing interfacial polycondensation, examples of the acid binder include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and cesium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; alkali metal weak acid salts such as sodium carbonate, potassium carbonate, and calcium acetate; alkaline earth metal weak acid salts; and organic bases such as pyridine. Preferred acid binders for performing interfacial polycondensation are alkali metal hydroxides and alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, and calcium hydroxide. These acid binders can also be used as a mixture. The usage ratio of the acid binder may be appropriately adjusted in consideration of the stoichiometric ratio (equivalent) of the reaction. Specifically, 1 equivalent or an excess amount of the acid binder may be used per 1 mole of the total hydroxyl groups of the divalent phenol as the raw material, and preferably 1 to 10 equivalents of the acid binder may be used.

[0109] As the solvent used in the method for producing the PC polymer according to this embodiment, there is no problem as long as it exhibits a certain degree or more of solubility in the obtained copolymer. Examples of the solvent include aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,1,2-tetrachloroethane, 1,1,2,2-tetrachloroethane, pentachloroethane, and chlorobenzene; ketones such as cyclohexanone, acetone, and acetophenone; and ethers such as tetrahydrofuran and 1,4-dioxane. These solvents may be used alone or in combination of two or more. Further, the interfacial polycondensation reaction may be carried out using two solvents that do not mix with each other.

[0110] As the organic solvent used in the method for producing a PC polymer according to this embodiment, it is preferable to use an organic solvent that is substantially immiscible with water and can dissolve 5% by mass or more of the finally obtained polycarbonate copolymer. The organic solvent is preferably an organic solvent that is substantially immiscible with water and can dissolve 5% by mass or more of the finally obtained polycarbonate copolymer. Here, the organic solvent that is "substantially immiscible with water" means that when water and the organic solvent are mixed in a composition range of 1:9 to 9:1 under normal temperature and pressure conditions, a solution consisting of a uniform layer (a solution in which neither a gelled product nor an insoluble substance is observed) cannot be obtained. Further, that the organic solvent is "capable of dissolving 5% by mass or more of the finally obtained polycarbonate copolymer" refers to the solubility of the polycarbonate copolymer measured under the conditions of a temperature of 20 to 30 °C and normal pressure. Also, the "finally obtained polycarbonate polymer" refers to the polymer obtained through the polymerization step in the method for producing a polycarbonate polymer of this embodiment, and it is the one before crosslinking. Examples of such organic solvents include aromatic hydrocarbons such as toluene, ketones such as cyclohexanone, and halogenated hydrocarbons such as methylene chloride. Among them, methylene chloride is preferable because of its high solubility.

[0111] Also, the catalyst used in the method for producing a PC polymer of this embodiment is not particularly limited. For example, tertiary amines such as trimethylamine, triethylamine, tributylamine, N,N-dimethylcyclohexylamine, pyridine, N,N-diethylaniline, N,N-dimethylaniline, quaternary ammonium salts such as trimethylbenzylammonium chloride, triethylbenzylammonium chloride, tributylbenzylammonium chloride, trioctylmethylammonium chloride, tetrabutylammonium chloride, tetrabutylammonium bromide, and quaternary phosphonium salts such as tetrabutylphosphonium chloride, tetrabutylphosphonium bromide are suitable. Furthermore, if necessary, a small amount of an antioxidant such as sodium sulfite or hydrosulfite salt may be added to the reaction system of the PC polymer of the present embodiment.

[0112] [Coating liquid composition] The coating liquid composition according to the present embodiment includes the resin composition according to the present embodiment and an organic solvent. That is, the coating liquid composition according to the present embodiment includes the resin according to the present embodiment and an organic solvent.

[0113] As the organic solvent according to the present embodiment, it can be appropriately selected in consideration of the solubility of materials such as the resin composition, the drying rate after molding, the influence during residual in the molded article, and the risk (fire or health hazard). Examples of the organic solvent according to the present embodiment include cyclic ethers (such as tetrahydrofuran (THF), dioxane, and dioxolane), cyclic ketones (such as cyclohexanone, cyclopentanone, and cycloheptanone), aromatic hydrocarbons (such as toluene, xylene, and chlorobenzene), ketones (such as methyl ethyl ketone (MEK) and methyl isobutyl ketone (MIBK)), halogenated hydrocarbons (such as dichloromethane and chloroform), esters (such as ethyl acetate, isopropyl acetate, isobutyl acetate, and butyl acetate), ethers (such as ethylene glycol dimethyl ether and ethylene glycol monoethyl ether), amides (such as dimethyl fumarate (DMF) and dimethylacetamide (DMAc)), and aprotic polar solvents (such as dimethyl sulfoxide (DMSO)).

[0114] In the coating liquid composition according to this embodiment, the concentration of the resin composition according to this embodiment may be any concentration that results in an appropriate viscosity according to the usage method of the coating liquid composition, and is preferably 0.1% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 35% by mass or less, and even more preferably 5% by mass or more and 30% by mass or less. If it is 40% by mass or less, the viscosity will not become too high and the coatability will be good. If it is 0.1% by mass or more, an appropriate viscosity can be maintained, and a homogeneous film can be obtained. In addition, the drying time after coating is shortened, and the concentration is appropriate for easily achieving the target film thickness.

[0115] In addition to the resin composition and the organic solvent according to this embodiment, the coating liquid composition may contain additives. Examples of the additives include low molecular compounds, colorants (such as dyes and pigments), functional compounds (such as charge transport materials, electron transport materials, hole transport materials, and charge generation materials), fillers (such as inorganic or organic fillers, fibers, cloths, and fine particles), antioxidants, ultraviolet absorbers, and acid scavengers. Further, the coating liquid composition may contain other resins other than the resin composition according to one embodiment of the present invention. As these additives and other resins, known substances that can be blended with the resin composition can be used.

[0116] When a charge transport substance is included, from the viewpoint of product performance, the ratio of the resin composition to the charge transport substance in the coating liquid composition according to this embodiment is preferably in the range of 20:80 to 80:20 by mass ratio, and more preferably in the range of 30:70 to 70:30. In the coating liquid composition according to this embodiment, the resin composition according to this embodiment may be used alone or in combination of two or more.

[0117] The coating liquid composition according to this embodiment is usually suitably used for forming a photosensitive layer of a laminated electrophotographic photoreceptor. The photosensitive layer of the laminated electrophotographic photoreceptor preferably includes at least a charge generation layer and a charge transport layer, and the coating liquid composition according to this embodiment is suitably used for forming the charge transport layer. Further, by further containing the above charge generating substance in the coating liquid composition according to this embodiment, it is also possible to use it for forming a photosensitive layer of a single-layer electrophotographic photoreceptor. It is also possible to use it for forming a protective layer of the photoreceptor.

[0118] [Molded article] The molded article according to this embodiment contains the resin according to this embodiment. The molded article according to this embodiment can be used for various applications in addition to the applications of the electrophotographic photoreceptor described later. For example, it can be suitably used for applications such as substrates, insulating layers, protective layers, adhesive layers, conductive layers, and structural materials of electronic devices. Further, the molded article according to this embodiment can also be applied to films, coating films, insulating materials, etc. The molded articles exemplified here only need to contain at least the resin according to this embodiment. In the molded article containing the resin according to this embodiment, the resin containing at least the structure represented by the above general formula (DE1) and the compound containing a dienophile structure or the resin containing a dienophile structure may be contained in the same layer or in different layers. When the resin containing at least the structure represented by the above general formula (DE1) and the compound containing a dienophile structure or the resin containing a dienophile structure are contained in different layers, the resin containing at least the structure represented by the general formula (DE1) and the compound containing a dienophile structure or the resin containing a dienophile structure may be contained in adjacent layers, respectively.

[0119] Here, in this specification, the film containing the resin according to this embodiment and the coating film containing the resin according to this embodiment are clearly distinguished. The film containing the resin according to this embodiment is a resin body formed from the resin according to this embodiment, and refers to a resin body having a thickness smaller than its length and width. For example, when the film according to this embodiment is a resin body formed by applying the coating composition according to this embodiment to an object and peeling it off from the object, this resin body is a film. The coating film containing the resin according to this embodiment refers to a layer formed by coating the object with the coating composition according to this embodiment. Generally, the coating film remains on the object as it is and constitutes a part of the finished product.

[0120] Also, the molded article according to this embodiment can be produced using the resin composition according to this embodiment. When using the resin composition according to this embodiment, either a wet molding method or a melt molding method can be applied as the molding method.

[0121] When obtaining a molded article by the wet molding method, (i) a method of molding at a temperature at which the polymer reaction proceeds, (ii) after obtaining a wet molded article at a temperature at which the polymer reaction does not substantially proceed, raising the temperature to a temperature at which the polymer reaction proceeds during the step of removing the solvent, and performing drying and the polymer reaction simultaneously, (iii) a method of obtaining a dry molded article by wet molding and drying at a temperature at which the polymer reaction does not substantially proceed, and then raising the temperature of the molded article to a temperature at which the polymer reaction proceeds and allowing the polymer reaction to occur can be adopted. Any of these methods may be used. Also, a method in which a resin modified by a polymer reaction is obtained in advance, and then a coating solution is prepared using the same resin to obtain a molded article may be used. In the wet molding method, the coating solution composition according to the above-described embodiment can be used.

[0122] When performing a melt forming method, it is usually carried out at a temperature equal to or higher than the temperature at which the Diels - Alder reaction proceeds. On the other hand, a method of reducing the melt viscosity and improving the fluidity by raising the forming temperature until the retro - Diels - Alder reaction occurs can also be suitably carried out. When forming under the conditions where the retro - Diels - Alder reaction occurs, by controlling the cooling rate and temperature of the formed article, the progress of the Diels - Alder reaction can be appropriately controlled again. Thereby, a molded article made of a resin with good forming fluidity and improved resin physical properties due to having a structure obtained by a polymer reaction can be obtained.

[0123] The temperature of the polymer reaction can be appropriately set according to the target physical properties and the intended use. In accordance with this reaction temperature, the type of functional group for the polymer reaction, the ratio of anthracene to dienophile, and the functional group concentration, etc. can be adjusted to set the cross - linking method.

[0124] As an example, for the polymer reaction temperature for an electrophotographic photoreceptor, it is preferably carried out by polymer reaction in a drying process after obtaining a wet - formed product by normal wet forming, and the temperature should be such that the functional low - molecular - weight compound does not deteriorate. For example, the polymer reaction temperature for an electrophotographic photoreceptor is preferably 60°C or higher and 170°C or lower, more preferably 80°C or higher and 160°C or lower, still more preferably 100°C or higher and 150°C or lower. It may also be 110°C or higher and 140°C or lower. When the reaction temperature exceeds 170°C, functional low - molecular - weight compounds such as charge - transporting substances may deteriorate. When the reaction temperature is less than 60°C, drying may not proceed sufficiently or may require a long time, which is not preferable.

[0125] On the other hand, in the applications of electronic devices, there are some processes that require high temperatures to adjust the film physical properties according to the drying and curing speeds during coating film formation. Therefore, the reaction temperature for electronic devices is preferably 60°C or higher and 250°C or lower, more preferably 100°C or higher and 200°C or lower, and even more preferably 110°C or higher and 180°C or lower. When the reaction temperature exceeds 250°C, there is a risk of failure of electronic components and decomposition of other organic materials. When the reaction temperature is less than 60°C, the polymer reaction may not proceed sufficiently, or for materials that react at such low temperatures, part of the reaction may proceed in the coating liquid composition, resulting in an increase in viscosity and other problems with the stability of the coating liquid.

[0126] In this embodiment, the polymer reaction of the resin composition can be carried out without adding a catalyst, a polymerization initiator, or the like. However, as long as the effects of this embodiment are not inhibited, substances such as a catalyst or a polymerization initiator may be added for the purpose of using in combination with other polymer reaction systems.

[0127] [Electrophotographic photoreceptor] The electrophotographic photoreceptor according to this embodiment has a layer containing the resin according to this embodiment. The resin according to this embodiment is preferably included in the outermost layer of the electrophotographic photoreceptor according to this embodiment. The electrophotographic photoreceptor according to this embodiment has a substrate and a photosensitive layer provided on the substrate, and the photosensitive layer contains the resin according to this embodiment. As long as the resin according to this embodiment is used in the photosensitive layer, the electrophotographic photoreceptor of this embodiment can be any type of electrophotographic photoreceptor, including various known types of electrophotographic photoreceptors. However, it is preferable that the photosensitive layer is a laminated electrophotographic photoreceptor having at least one charge generation layer and at least one charge transport layer, or a single-layer electrophotographic photoreceptor having a charge generating substance and a charge transport substance in one layer.

[0128] The resin according to this embodiment may be used in any part of the photosensitive layer. However, in order to fully exhibit the effects of this embodiment, it is desirable to use it as a binder resin for the charge transporting material in the charge transport layer or as a binder resin for a single photosensitive layer. Further, it is desirable to use it not only for the photosensitive layer but also for the surface protective layer. In the case of a multilayer electrophotographic photoreceptor having two charge transport layers, it is preferably used for either of the charge transport layers. In the electrophotographic photoreceptor of this embodiment, the resin according to this embodiment may be used alone or in combination of two or more. Further, binder resin components such as other polycarbonates may be contained within a range that does not inhibit the object of this embodiment as desired. Furthermore, additives such as antioxidants may be contained.

[0129] The electrophotographic photoreceptor of this embodiment has a photosensitive layer on a conductive substrate. When the photosensitive layer has a charge generation layer and a charge transport layer, the charge transport layer may be laminated on the charge generation layer, or conversely, the charge generation layer may be laminated on the charge transport layer. Further, a photosensitive layer containing a charge generating substance and a charge transporting substance simultaneously in one layer may also be used. Furthermore, a conductive or insulating protective film may be formed on the surface layer as necessary. By using the resin according to this embodiment for the outermost layer, an electrophotographic photoreceptor excellent in solvent resistance and abrasion resistance can be obtained. Furthermore, an intermediate layer such as an adhesive layer for improving the adhesiveness between layers or a blocking layer serving as a charge blocking function may be formed.

[0130] As the conductive substrate material used for the electrophotographic photoreceptor of this embodiment, various known materials can be used. Specifically, aluminum, nickel, chromium, palladium, titanium, molybdenum, indium, gold, platinum, silver, copper, zinc, brass, stainless steel, lead oxide, tin oxide, indium oxide, ITO (indium tin oxide: tin-doped indium oxide), or graphite, in the form of plates, drums, and sheets, can be used. Conductive treatment can be performed by coating through vapor deposition, sputtering, or coating, etc. Glass, cloth, paper, and plastic films, sheets, or seamless belts, as well as metal drums subjected to metal oxidation treatment such as electrode oxidation, can be used.

[0131] The charge generation layer has at least a charge generation material. This charge generation layer can be obtained by forming a layer of the charge generation material on the substrate serving as its base by vacuum deposition or sputtering, etc., or by forming a layer in which the charge generation material is bound using a binder resin on the substrate serving as its base. As the method for forming the charge generation layer using a binder resin, various known methods can be used. Usually, for example, a coating liquid composition in which the charge generation material is dispersed or dissolved together with a binder resin in an appropriate solvent is applied onto a predetermined base substrate and dried to obtain a wet molded body, which is a preferred method.

[0132] As the charge generation material in the charge generation layer, various known materials can be used. Specific compounds include elemental selenium (e.g., amorphous selenium, trigonal selenium, etc.), selenium alloys (e.g., selenium-tellurium, etc.), selenium compounds or selenium-containing compositions (e.g., As2Se3, etc.), inorganic materials composed of Group 12 and Group 16 elements of the periodic table (e.g., zinc oxide, CdS-Se, etc.), oxide-based semiconductors (e.g., titanium oxide, etc.), silicon-based materials (e.g., amorphous silicon, etc.), metal-free phthalocyanine pigments (e.g., τ-type metal-free phthalocyanine, χ-type metal-free phthalocyanine, etc.), metal phthalocyanine pigments (e.g., α-type copper phthalocyanine, β-type copper phthalocyanine, γ-type copper phthalocyanine, ε-type copper phthalocyanine, X-type copper phthalocyanine, A-type titanyl phthalocyanine, B-type titanyl phthalocyanine, C-type titanyl phthalocyanine, D-type titanyl phthalocyanine, E-type titanyl phthalocyanine, F-type titanyl phthalocyanine, G-type titanyl phthalocyanine, H-type titanyl phthalocyanine, K-type titanyl phthalocyanine, L-type titanyl phthalocyanine, M-type titanyl phthalocyanine, N-type titanyl phthalocyanine, Y-type titanyl phthalocyanine, Y-type oxotitanium phthalocyanine, α-type oxotitanium phthalocyanine, β-type oxotitanium phthalocyanine, titanyl phthalocyanine showing a strong diffraction peak at a black angle 2θ of 27.3 ± 0.2 degrees in the X-ray diffraction pattern, and gallium phthalocyanine, etc.), cyanine dyes, anthracene pigments, bisazo pigments, pyrene pigments, polycyclic quinone pigments, quinacridone pigments, indigo pigments, perylene pigments, pyrylium dyes, squarium pigments, anthraanthrone pigments, benzimidazole pigments, azo pigments, thioindigo pigments, quinoline pigments, lake pigments, oxazine pigments, dioxazine pigments, triphenylmethane pigments, azulenium dyes, triarylmethane dyes, xanthine dyes, thiazine dyes, thiapyrylium dyes, polyvinylcarbazole, and bisbenzimidazole pigments, etc. These compounds can be used alone or in combination of two or more compounds as the charge generation substance.Among these charge generating materials, preferred charge generating materials include those specifically described in JP-A-11-172003.

[0133] The charge transport layer can be obtained as a wet molded body by forming, on a substrate serving as a base, a layer formed by binding a charge transport material with a binder resin. There is no particular limitation on the binder resin for the charge generation layer and the charge transport layer described above, and various known resins can be used. Specifically, for example, polystyrene, polyvinyl chloride, polyvinyl acetate, vinyl chloride-vinyl acetate copolymer, polyvinyl acetal, alkyd resin, acrylic resin, polyacrylonitrile, polycarbonate, polyurethane, epoxy resin, phenol resin, polyamide, polyketone, polyacrylamide, butyral resin, polyester resin, vinylidene chloride-vinyl chloride copolymer, methacrylic resin, styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone alkyd resin, phenol-formaldehyde resin, styrene-alkyd resin, melamine resin, polyether resin, benzoguanamine resin, epoxy acrylate resin, urethane acrylate resin, poly-N-vinylcarbazole, polyvinyl butyral, polyvinyl formal, polysulfone, casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, carboxy-methyl cellulose, vinylidene chloride-based polymer latex, acrylonitrile-butadiene copolymer, vinyl toluene-styrene copolymer, soybean oil-modified alkyd resin, nitrated polystyrene, polymethylstyrene, polyisoprene, polythiocarbonate, polyarylate, polyhaloarylate, polyallyl ether, polyvinyl acrylate, and polyester acrylate, etc. can be mentioned. These can be used singly or in combination of two or more. Note that as the binder resin in the charge generation layer and / or the charge transport layer, it is preferable to use the PC polymer of the present embodiment described above.

[0134] As a method for forming the charge transport layer, various known methods can be used. However, a method in which a coating liquid composition obtained by dispersing or dissolving a charge transport material together with the PC polymer of the present embodiment in a suitable solvent is applied onto a substrate serving as a predetermined base and dried to obtain a wet molded body is preferable. The mixing ratio of the charge transport material and the PC polymer used for forming the charge transport layer is preferably in the range of 20:80 to 80:20 by mass ratio, more preferably in the range of 30:70 to 70:30. In this charge transport layer, the PC polymer of the present embodiment can be used alone or in combination of two or more. Also, within a range not inhibiting the object of the present invention, it is possible to use another binder resin in combination with the PC polymer of the present embodiment.

[0135] The thickness of the charge transport layer formed in this way is usually about 5 μm or more and 100 μm or less, preferably 10 μm or more and 50 μm or less, more preferably 15 μm or more and 40 μm or less. If this thickness is 5 μm or more, the initial potential will not decrease, and if it is 100 μm or less, deterioration of electrophotographic characteristics can be prevented. As the charge transport material that can be used together with the PC polymer of this embodiment, various known compounds can be used. Examples of such compounds include, for example, carbazole compounds, indole compounds, imidazole compounds, oxazole compounds, pyrazole compounds, oxadiazole compounds, pyrazoline compounds, thiadiazole compounds, aniline compounds, hydrazone compounds, aromatic amine compounds, aliphatic amine compounds, stilbene compounds, fluorenone compounds, butadiene compounds, quinone compounds, quinodimethane compounds, thiazole compounds, triazole compounds, imidazolone compounds, imidazolidine compounds, bisimidazolidine compounds, oxazolone compounds, benzothiazole compounds, benzimidazole compounds, quinazoline compounds, benzofuran compounds, acridine compounds, phenazine compounds, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, ethylcarbazole resin, or polymers having these structures in the main chain or side chain, etc. are preferably used. These compounds may be used alone or in combination of two or more. Among these charge transport materials, the compounds specifically exemplified in JP-A-11-172003 and the charge transport materials represented by the following structures are particularly preferably used.

[0136]

Chemical formula

[0137]

Chemical formula

[0138]

Chemical formula

[0139]

Chemical formula

[0140]

Chem.

[0141]

Chem.

[0142]

Chem.

[0143]

Chem.

[0144]

Chem.

[0145]

Chem.

[0146]

Chem.

[0147]

Chem.

[0148]

Chem.

[0149]

Chem.

[0150] In the electrophotographic photoreceptor according to this embodiment, it is preferable to use the resin composition according to this embodiment as a binder resin in at least one of the charge generation layer, the charge transport layer, and the surface protective layer.

[0151] In the electrophotographic photoreceptor according to this embodiment, an undercoat layer such as is usually used can be provided between the conductive substrate and the photosensitive layer. As this undercoat layer, for example, components such as fine particles (for example, titanium oxide, aluminum oxide, zirconia, titanic acid, zirconic acid, lead lanthanum, titanium black, silica, lead titanate, barium titanate, tin oxide, indium oxide, and silicon oxide), polyamide resin, phenol resin, casein, melamine resin, benzoguanamine resin, polyurethane resin, epoxy resin, cellulose, nitrocellulose, polyvinyl alcohol, and polyvinyl butyral resin can be used. Further, as the resin used for this undercoat layer, the binder resin may be used, or the resin composition according to this embodiment may be used. These fine particles and resins can be used alone or in various mixtures. When used as these mixtures, it is preferable to use inorganic fine particles and resin in combination because a film with good smoothness is formed.

[0152] The thickness of this undercoat layer is 0.01 μm or more and 10 μm or less, preferably 0.1 μm or more and 7 μm or less. When this thickness is 0.01 μm or more, it becomes possible to form the undercoat layer uniformly, and when it is 10 μm or less, it is possible to suppress a decrease in electrophotographic characteristics. Also, a known blocking layer such as is usually used can be provided between the conductive substrate and the photosensitive layer. As this blocking layer, a resin of the same type as the above binder resin can be used. Also, the resin composition according to this embodiment may be used. The thickness of this blocking layer is 0.01 μm or more and 20 μm or less, preferably 0.1 μm or more and 10 μm or less. When this thickness is 0.01 μm or more, it becomes possible to form the blocking layer uniformly, and when it is 20 μm or less, it is possible to suppress a decrease in electrophotographic characteristics.

[0153] Furthermore, a protective layer may be laminated on the photosensitive layer of the electrophotographic photoreceptor according to this embodiment. For this protective layer, a resin of the same type as the above binder resin can be used. In particular, it is preferable to use the resin composition according to this embodiment. The thickness of this protective layer is 0.01 μm or more and 20 μm or less, preferably 0.1 μm or more and 10 μm or less. And this protective layer may contain a conductive material such as the above charge generating substance, charge transporting substance, additive, metal and its oxide, nitride, or salt, alloy, carbon black, and organic conductive compound.

[0154] Furthermore, in order to improve the performance of this electrophotographic photoreceptor, within a range that does not lose the effects of the present invention, a binder, plasticizer, curing catalyst, fluidity imparting agent, pinhole controller, and spectral sensitivity sensitizer (sensitizing dye), etc. may be added to the charge generation layer and charge transport layer. Also, for the purpose of preventing an increase in residual potential, a decrease in charging potential, and a decrease in sensitivity with repeated use, additives such as various chemical substances, antioxidants, surfactants, curl preventers, and leveling agents can be added.

[0155] Examples of the binder include silicone resin, polyamide resin, polyurethane resin, polyester resin, epoxy resin, polyketone resin, polycarbonate copolymer, polystyrene resin, polymethacrylate resin, polyacrylamide resin, polybutadiene resin, polyisoprene resin, melamine resin, benzoguanamine resin, polychloroprene resin, polyacrylonitrile resin, ethyl cellulose resin, nitrocellulose resin, urea resin, phenol resin, phenoxy resin, polyvinyl butyral resin, formal resin, vinyl acetate resin, vinyl acetate / vinyl chloride copolymer resin, and polyester carbonate resin, etc. Also, at least one of a thermosetting resin and a photocurable resin can be used. In any case, it is a resin that is electrically insulating and can form a film in a normal state, and there is no particular limitation as long as the effects of this embodiment are not impaired.

[0156] Specific examples of the plasticizer include, for example, biphenyl, chlorinated biphenyl, o - terphenyl, halogenated paraffin, dimethylnaphthalene, dimethyl phthalate, dibutyl phthalate, dioctyl phthalate, diethylene glycol phthalate, triphenyl phosphate, diisobutyl adipate, dimethyl sebacate, dibutyl sebacate, butyl laurate, methyl phthalyl ethyl glycolate, dimethyl glycol phthalate, methylnaphthalene, benzophenone, polypropylene, polystyrene, and fluorohydrocarbon, etc.

[0157] Specific examples of the curing catalyst include, for example, methanesulfonic acid, dodecylbenzenesulfonic acid, and dinonylnaphthalenedisulfonic acid, etc. Examples of the fluidity - imparting agent include, for example, modaflo, and acronal 4F, etc. Examples of the pinhole controller include, for example, benzoin, and dimethyl phthalate. These plasticizer, curing catalyst, fluidity - imparting agent, and pinhole controller are preferably used at 5 mass% or less with respect to the charge - transporting material as long as the effects of the present invention are not lost.

[0158] In addition, as the spectral - sensitivity sensitizer, when using a sensitizing dye, for example, triphenylmethane - type dyes (for example, methyl violet, crystal violet, night blue, and victoria blue, etc.), acridine dyes (for example, erythrosine, rhodamine B, rhodamine 3R, acridine orange, and flupheosine, etc.), thiazine dyes (for example, methylene blue, and methylene green, etc.), oxazine dyes (capri blue, and meldola blue, etc.), cyanine dyes, merocyanine dyes, styryl dyes, pyrylium - salt dyes, and thiapyrylium - salt dyes, etc. are suitable.

[0159] In the photosensitive layer, for the purposes of improving sensitivity, reducing residual potential, and reducing fatigue during repeated use, an electron-accepting substance can be added within a range that does not lose the effects of the present invention. Specific examples thereof include, for example, succinic anhydride, maleic anhydride, dibromo maleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride, 4-nitrophthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, o-dinitrobenzene, m-dinitrobenzene, 1,3,5-trinitrobenzene, p-nitrobenzonitrile, picryl chloride, quinone chloroimide, chloranil, bromanil, benzoquinone, 2,3-dichlorobenzoquinone, dichlorodicyanoparabenzoquinone, naphthoquinone, diphenoquinone, tropoquinone, anthraquinone, 1-chloroanthraquinone, dinitroanthraquinone, 4-nitrobenzophenone, 4,4'-dinitrobenzophenone, 4-nitrobenzalmalononitrile, ethyl α-cyano-β-(p-cyanophenyl)acrylate, 9-anthracenylmethylmalononitrile, 1-cyano-(p-nitrophenyl)-2-(p-chlorophenyl)ethylene, 2,7-dinitrofluorenone, 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, 9-fluorenylidene-(dicyanomethylene malononitrile), polynitro-9-fluorenylidene-(dicyanomethylene malonodinitrile), picric acid, o-nitrobenzoic acid, p-nitrobenzoic acid, 3,5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, phthalic acid, and mellitic acid. Compounds with a large electron affinity are preferred. These compounds may be added to either the charge generation layer or the charge transport layer, and the blending ratio is 0.01 parts by mass or more and 200 parts by mass or less, preferably 0.1 parts by mass or more and 50 parts by mass or less, when the amount of the charge generation substance or the charge transport substance is 100 parts by mass within a range that does not lose the effects of the present invention.

[0160] Also, for surface improvement, ethylene tetrafluoride resin, vinylidene chloride fluoride resin, ethylene tetrafluoride hexafluoropropylene resin, vinyl fluoride resin, vinylidene fluoride resin, dichloroethylene difluoride resin, their copolymers, and fluorine-based graft polymers may be used within the range that does not impair the effects of the present invention. The blending ratio of these surface modifiers is 0.1% by mass or more and 60% by mass or less, preferably 5% by mass or more and 40% by mass or less, with respect to the binder resin, within the range that does not impair the effects of the present invention. If this blending ratio is 0.1% by mass or more, surface modification such as surface durability and reduction of surface energy becomes sufficient, and if it is 60% by mass or less, the electrophotographic characteristics will not deteriorate.

[0161] As the antioxidant, for example, hindered phenol-based antioxidants, aromatic amine-based antioxidants, hindered amine-based antioxidants, sulfide-based antioxidants, and organic phosphate-based antioxidants are preferable. The blending ratio of these antioxidants is usually 0.01% by mass or more and 10% by mass or less, preferably 0.1% by mass or more and 2% by mass or less, with respect to the charge transport material, within the range that does not impair the effects of the present invention. Specific examples of such antioxidants include the compounds of chemical general formulas [Chemical Formula 94] to [Chemical Formula 101] described in the specification of JP-A-11-172003. These antioxidants may be used alone or in combination of two or more, and in addition to the photosensitive layer, they may be added to the surface protection layer, the undercoat layer, or the blocking layer.

[0162] Specific examples of the solvent used in forming at least one of the charge generation layer and the charge transport layer include, for example, aromatic solvents (such as benzene, toluene, xylene, and chlorobenzene), ketones (such as acetone, methyl ethyl ketone, and cyclohexanone), alcohols (such as methanol, ethanol, and isopropanol), esters (such as ethyl acetate and ethyl cellosolve), halogenated hydrocarbons (such as carbon tetrachloride, carbon tetrabromide, chloroform, dichloromethane, and tetrachloroethane), ethers (such as tetrahydrofuran, dioxolane, and dioxane), sulfoxides (such as dimethyl sulfoxide), and amides (such as dimethylformamide and diethylformamide). These solvents may be used alone or in combination of two or more as a mixed solvent.

[0163] The photosensitive layer of the single-layer type electrophotographic photoreceptor can be easily formed by using the above-described charge generating substance, charge transporting substance, and additive, and applying the resin composition according to the present embodiment as a binder resin. Further, it is preferable to add at least one of the hole transporting substance and the electron transporting substance described above as the charge transporting substance. As the electron transporting substance, the electron transporting substances exemplified in JP-A-2005-139339 can be preferably applied. Coating of each layer can be performed using various coating apparatuses such as known apparatuses. Specifically, for example, it can be performed using an applicator, a spray coater, a bar coater, a chip coater, a roll coater, a dip coater, and a doctor blade.

[0164] The thickness of the photosensitive layer in the electrophotographic photoreceptor is 5 μm or more and 100 μm or less, preferably 8 μm or more and 50 μm or less. When it is 5 μm or more, it is possible to prevent the initial potential from becoming low, and when it is 100 μm or less, it is possible to suppress the deterioration of electrophotographic characteristics. The ratio of the charge generating substance to the resin composition used in the production of the electrophotographic photoreceptor is preferably in the range of 20:80 to 80:20 by mass ratio, and more preferably in the range of 30:70 to 70:30.

[0165] The electrophotographic photoreceptor thus obtained has, as a binder resin, a resin modified by a polymer reaction of the resin composition according to the present embodiment in the photosensitive layer. Therefore, it is excellent in characteristics such as durability, has excellent electrical characteristics (electrophotographic characteristics), and is a photoreceptor that maintains excellent electrophotographic characteristics over a long period of time. The electrophotographic photoreceptor is suitably used in various electrophotographic fields such as copiers (monochrome, multi-color, full-color, analog, digital), printers (laser, LED, liquid crystal shutter), facsimiles, plate-making machines, and devices having a plurality of these functions.

[0166] [Method for manufacturing electrophotographic photoreceptor] The method for manufacturing an electrophotographic photoreceptor according to the present embodiment includes a step of applying the coating liquid composition according to the present embodiment to a conductive substrate by a wet forming method, a step of removing the organic solvent in the coating liquid composition by heating, and a step of performing a polymer reaction of the resin composition in the coating liquid composition by heating simultaneously with or subsequent to the heating in the step of removing the organic solvent.

[0167] In the step of applying to the conductive substrate, the coating thickness of the coating liquid composition can be appropriately set according to the thickness of the photosensitive layer of the electrophotographic photoreceptor according to the present embodiment. In the step of removing the organic solvent, it can be appropriately set according to the type of the organic solvent in the coating liquid composition according to the present embodiment. In the step of performing the polymer reaction of the resin composition, the heating temperature is the same as the reaction temperature for the electrophotographic photoreceptor in the molded product according to the present embodiment.

Example

[0168] Next, the present invention will be described in more detail by way of examples and comparative examples. However, the present invention is not limited to these examples, and various modifications and applications are possible without departing from the spirit of the present invention.

[0169] [Production Example: Preparation of Monomer] <Production Example 1: Synthesis of 9-(4-Hydroxyphenyl)Anthracene> A reaction vessel equipped with a mechanical stirrer, stirring blades, baffle plates, and a reflux tube was purged with Ar, charged with 9-bromoanthracene (117 g), 4-methoxyphenylboronic acid (117 g), and a toluene / ethanol mixed solvent (3.0 L), and stirred at room temperature for 10 minutes. Subsequently, 2N aqueous K2CO3 solution (875 mL) was added, and argon was bubbled into the reaction solution for 30 minutes. After degassing, tetrakistriphenylphosphine palladium (32.4 g) was added, and the mixture was stirred under heating reflux for 18 hours. Ethyl acetate was added to the reaction solution for extraction. The organic layer was washed with saturated brine, dehydrated with sodium sulfate, and concentrated to obtain a crude product (360 g). Subsequently, impurities were removed by column chromatography using toluene as the developing solvent, and recrystallization was performed with a toluene / hexane mixed solvent to obtain 9-(4-methoxyphenyl)anthracene (145 g). A reaction vessel equipped with a mechanical stirrer, stirring blades, and baffle plates was purged with Ar, charged with 9-(4-methoxyphenyl)anthracene (97 g) obtained above and dichloromethane (1.2 L), and cooled to -75°C. A dichloromethane solution (0.5 L) of boron tribromide (98 g) was added dropwise thereto over 3 hours. After completion of the dropwise addition, the temperature was gradually raised to room temperature, and stirring was continued for 24 hours. Thereafter, the reaction solution was poured into ice water and extracted three times with ethyl acetate. Ion-exchanged water (1 L) was added, and extraction was performed twice with ethyl acetate (1 L). The organic layer was washed with saturated brine, dehydrated with sodium sulfate, and concentrated to obtain a crude product (120 g). Subsequently, impurities were removed by column chromatography using ethyl acetate / hexane as the developing solvent, recrystallized with an ethyl acetate / hexane mixed solvent, and then reprecipitated with chloroform / hexane to obtain 9-(4-hydroxyphenyl)anthracene (66 g).

[0170] [Production Example: Preparation of Oligomer] <Production Example 2: Synthesis of Bisphenol CZ Oligomer (Bischloroformate)> 66.3 g (224 mmol) of 1,1-bis(3-methyl-4-hydroxyphenyl)cyclohexane (bisphenol Z) was suspended in 1080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution prepared by dissolving 44.0 g (435 mmol) of triethylamine in 120 mL of methylene chloride was added dropwise in the temperature range of 5°C to 15°C. Next, after stirring for 30 minutes, methylene chloride was distilled off until a predetermined concentration was reached. To the remaining liquid, 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added for washing. Thereafter, washing was repeated 5 times with 210 mL of pure water to obtain a methylene chloride solution of bisphenol CZ oligomer having a chloroformate group at the molecular terminal. The chloroformate concentration of the obtained solution was 1.13 mol / L, the solid concentration was 0.247 kg / L, and the average degree of polymerization was 1.05. Hereinafter, this obtained raw material is referred to as CZ-CF.

[0171] The average degree of polymerization (n X ) of the bischloroformate compound represented by the following general formula (X1) was determined using the following mathematical formula (Formula 1). Average degree of polymerization (n X ) = 1 + (Mav - M1) / M2 ··· (Formula 1) (In the above mathematical formula (Formula 1), Mav is (2 × 1000 / (CF value)), M2 is (M1 - 98.92), and M1 is, in the following general formula (X1), n Xis the molecular weight of the bis(chloroformate) compound when = 1, the CF value (N / kg) is (CF value / concentration), the CF value (N) is the number of chlorine atoms in the bis(chloroformate) compound represented by the following general formula (X1) contained in 1 L of the reaction solution, and the concentration (kg / L) is the amount of solid content obtained by concentrating 1 L of the reaction solution. Here, 98.92 is the total atomic weight of 2 chlorine atoms, 1 oxygen atom, and 1 carbon atom eliminated by polycondensation of bis(chloroformate) compounds with each other.) When calculating the average degree of polymerization in the case of synthesizing bis(chloroformate) using two or more raw materials, M1 is calculated and obtained based on the molecular weight obtained by averaging the molecular weights of the raw materials used in the molar ratio. As an example, when synthesizing using 366 moles of a monomer with a molecular weight of 268 and 108 moles of a monomer with a molecular weight of 214, M1 is calculated by the following calculation formula. M1=(268×(366÷(366 + 108)))+214×(108÷(366 + 108))+124.9 "124.9" in the calculation formula of this M1 is the molecular weight increment when two hydrogen atoms of the monomer used are lost and two carbon atoms, two oxygen atoms, and two chlorine atoms are each increased.

[0172] [Chemical formula]

[0173] In the general formula (X1), Ar X1 is a divalent group. For example, in the case of the bis(chloroformate) compound (bisphenol CZ oligomer) according to Production Example 2, the divalent group represented by the following general formula (10) corresponds to Ar X1 .

[0174] [Chemical formula]

[0175] In the case of the bis(chloroformate) oligomer represented by the general formula (1A), Ar 33 corresponds to Ar X1 and n31 corresponds to n X In the case of the bischloroformate oligomer represented by the general formula (2A), Ar 34 corresponds to Ar X1 and n 32 corresponds to n X

[0176] <Production Example 3: Synthesis of Bisphenol C Oligomer (Bischloroformate)> 57.3 g (224 mmol) of 2,2-bis(3-methyl-4-hydroxyphenyl)propane (bisphenol C) was suspended in 1080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto and dissolved. A solution prepared by dissolving 44.0 g (435 mmol) of triethylamine in 120 mL of methylene chloride was added dropwise thereto in the temperature range of 5°C to 15°C. Next, after stirring for 30 minutes, methylene chloride was distilled off until a predetermined concentration was reached. To the residue, 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added for washing. Thereafter, washing was repeated 5 times with 210 mL of pure water to obtain a methylene chloride solution of bisphenol CZ oligomer having a chloroformate group at the molecular terminal. The chloroformate concentration of the obtained solution was 1.13 mol / L, the solid concentration was 0.215 kg / L, and the average degree of polymerization was 1.00. Hereinafter, this obtained raw material is referred to as C-CF.

[0177] [Synthesis Example 1] (Production of PC Polymer) ​​A mechanical stirrer, a stirring blade, and a reaction vessel equipped with a baffle were charged with CZ-CF (69 mL) of Production Example 2 and methylene chloride (121 mL). To this, 9-(4-hydroxyphenyl)anthracene (0.637 g) of Production Example 1 was added as a terminal terminator, and the mixture was stirred well to be thoroughly mixed. After cooling the temperature inside the reactor to 10 °C, the prepared potassium hydroxide solution of 1,1-bis(3-methyl-4-hydroxyphenyl)cyclohexane (solution preparation method: 63 mL of 1.8N aqueous potassium hydroxide solution (7.3 g of potassium hydroxide) was prepared, cooled to room temperature or below, and then 100 mg of hydrosulfite was added as an antioxidant and completely dissolved to prepare) was added in its entirety, and while stirring, 1.0 mL of an aqueous triethylamine solution (7 vol%) was added, and stirring was continued for 1 hour. The obtained reaction mixture was diluted with 300 mL of methylene chloride and 50 mL of water, and washed. The lower layer was separated and further washed successively with 100 mL of water once, 100 mL of 0.03N hydrochloric acid once, and 100 mL of water three times. The obtained methylene chloride solution was dropped into methanol with stirring, and the obtained reprecipitate was filtered and dried to obtain a PC polymer (PC-1) having the following structure.

[0178] (Specification of PC polymer) The PC polymer (PC-1) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and when the reduced viscosity [ηsp / C] at 20 °C was measured, it was 1.06 dL / g. The structure and composition of the obtained PC-1 1 When analyzed by 1H-NMR spectrum, it was confirmed to be a PC polymer composed of the following repeating unit, number of repeating units, composition, and terminal composition. In the following description, "DE1" is a structure represented by the general formula (DE1). The reduced viscosity was measured using an automatic viscosity measuring device VMR-042 manufactured by a separate company and an Ubbelohde modified viscometer (RM type) for automatic viscosity. 1 The 1H-NMR spectrum was measured using a nuclear magnetic resonance apparatus JNM-ECZ400S manufactured by JEOL Ltd. Also, 1 The measurement conditions of the 1H-NMR spectrum are as follows.

[0179] ( 1 (Measurement conditions of 1H-NMR spectrum) · Solvent: CD2Cl2 · Measurement concentration (sample amount / solvent amount): 10 mg / mL · Number of integrations: 16 times

[0180]

Chemical formula

[0181] The composition ratio (mol%) is BisCZ:DE1 = 97:3. Also, the molar composition of the DE1 component with respect to all terminals is 98.7%, and the remaining 1.3% is the OH group remaining unreacted from 1,1-bis(3-methyl-4-hydroxyphenyl)cyclohexane. The anthracene concentration is 0.09 mmol / g.

[0182] [Synthesis Example 2] (Production of PC polymer) To a reaction vessel equipped with a mechanical stirrer, stirring blades, and a baffle, C-CF (109 mL) and methylene chloride (91 mL) from Production Example 3 were injected. To this, N-(4-hydroxyphenyl)maleimide (hereinafter referred to as Male1) (2.87 g) as a terminal terminator was dissolved in 40 mL of acetone and added, and the mixture was stirred well to be thoroughly mixed. After cooling until the temperature inside the reactor reached 10°C, 10 mL of a 2.4 mol / L aqueous potassium carbonate solution (3.3 g of potassium carbonate and 0.1 g of hydrosulfite as an antioxidant) was added, and while stirring, 2.0 mL of a triethylamine aqueous solution (7 vol%) was added, and the mixture was stirred for 30 minutes. To this solution, a prepared solution of 2,2-bis(3-methyl-4-hydroxyphenyl)propane (BisC) (solution preparation method: 57 mL of a 2.0 mol / L aqueous potassium hydroxide solution (prepared by preparing 6.3 g of potassium hydroxide and cooling it to room temperature or below, and then adding 8.1 g of BisC) was added in its entirety, and stirring was continued for another 30 minutes. The resulting reaction mixture was diluted with 0.5 L of methylene chloride and 0.1 L of water, and washed. The lower layer was separated and further washed successively with 0.15 L of water once, 0.15 L of 0.03 N hydrochloric acid once, and 0.15 L of water three times. The resulting methylene chloride solution was added dropwise to methanol with stirring, and the obtained reprecipitate was filtered and dried to obtain a PC polymer (PC-2) having the following structure.

[0183] (Specification of PC Polymer) The PC polymer (PC-2) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20 °C was measured, and it was 0.19 dL / g. The structure and composition of the obtained PC-2 1 When analyzed by 1H-NMR spectrum, it was confirmed that it was a PC polymer composed of the following repeating unit, number of repeating units, and composition.

[0184] [Chemical formula]

[0185] The composition ratio (mol%) is BisC:Male1 = 86:14. The dienophile group (maleimide group) concentration is 0.50 mmol / g.

[0186] [Example 1] [Preparation 1] Confirmation of Polymer Reaction 2.97 g of PC-1 and 0.53 g of PC-2 were weighed into a sample tube with a screw cap, dissolved in 15 mL of dichloromethane to obtain a coating solution composition. The obtained coating solution composition was cast and formed into a film on a smooth glass plate using an applicator with a gap of 500 μm. After air-drying for 1 hour, the film was peeled off from the glass plate and treated at 50 °C for 16 hours in a vacuum dryer (degree of vacuum: 1 - 100 Pa) to remove the solvent, and a resin film with a film thickness of 70 μm at the coated portion was obtained. Using the obtained resin film as a sample, heat treatment was carried out in a vacuum dryer under the following heat treatment conditions, and the change in the molecular weight distribution was confirmed by gel permeation chromatography (GPC) under the following conditions. For the sample, 10 mg of the sample is weighed accurately with a precision balance into a 20 mL sample bottle, 10 mL of THF is added and dissolved, and it is collected into a vial through a 0.45 μm cartridge type filter. (GPC conditions) SEC apparatus: HLC - 8420 GPC manufactured by Tosoh Corporation Column: 1 TSKguardcolumn HXL - H + 2 TSKgel GMH - XL + 1 G2000H - XL manufactured by Tosoh Corporation Mobile solvent: THF (special grade without stabilizer manufactured by Wako Pure Chemical Industries, Ltd.) Detector: Differential refractive index (RI) detector Concentration: 0.1 w / v% Injection volume: 100 μL Flow rate: 1.0 mL / min Column temperature: 40 °C Standard sample for calibration curve: TSK standard polystyrene manufactured by Tosoh Corporation The obtained molecular weight distribution is shown in Figure 1. Also, a graph showing the relationship between the molecular weight and the heating temperature and heating time for each heat treatment condition is shown in Figure 2. (Heat treatment conditions) (i) Temperature 150 °C, 1 hour (ii) Temperature 150 °C, 2 hours (iii) Temperature 150 °C, 3 hours (iv) Temperature 200 °C, 1 hour

[0187] [Example 2] (Preparation of a coating liquid for coating an electrophotographic photoreceptor photosensitive layer containing a copolymer and a reactive substance, and production of a laminated electrophotographic photoreceptor) An aluminum plate with a thickness of 100 μm was used as the conductive substrate, and a charge generation layer and a charge transport layer were sequentially laminated on its surface to manufacture an electrophotographic photoreceptor having a laminated photosensitive layer. 0.5 parts by mass of Y-type oxotitanium phthalocyanine was used as the charge generating substance, and 0.5 parts by mass of butyral resin was used as the binder resin. These were added to 19 parts by mass of THF as a solvent and dispersed by a ball mill. This dispersion was coated on the surface of the conductive substrate film using a bar coater and dried at 70 °C for 30 minutes to form a charge generation layer with a thickness of about 0.5 μm. Next, as a coating liquid composition for the charge transport layer, PC-1 (2.97 g: 0.27 mmol of anthracene group), PC-2 (0.53 g: 0.27 mmol of maleimide group), and a charge transport substance (CTM-1 (2.34 g)) having the following structure were weighed into a sample tube with a screw cap and dissolved in 30 mL of dichloromethane to obtain a coating liquid composition for the charge transport layer. It was confirmed that the resin coating liquid did not gel or the like for more than one week at room temperature and was stable as a coating liquid.

[0188]

Chemical formula

[0189] The obtained coating liquid composition was cast and formed on the charge generation layer obtained above using an applicator with a gap of 375 μm. After air drying for 1 hour, it was treated at a temperature of 50 °C for 16 hours in a vacuum dryer (the degree of vacuum was from 1 Pa to 100 Pa) to remove the solvent and obtain a resin film with a film thickness of 30 μm at the coated portion. Regarding the laminated electrophotographic photoreceptor obtained above and the one obtained by further treating the electrophotographic photoreceptor in a vacuum dryer at a temperature of 150 °C for 1 hour, they were attached to an aluminum drum with a diameter of φ60 mm, and the photoelectric charging characteristics were evaluated in the EV mode for the light attenuation characteristics of the surface potential using a static charging test apparatus CYNTHIA54IM (manufactured by Gentec Co., Ltd.). It was confirmed that the obtained photoreceptor had its surface potential attenuated according to the light amount and the surface potential was reduced to 1 / 2 or less of the initial charging amount, and it was confirmed that the same composition functioned as an electrophotographic photoreceptor. The obtained results are shown in Figure 3. Next, in order to confirm the abrasion resistance of the electrophotographic photoreceptor, a coating liquid having the same composition as the outermost charge transport layer was prepared, and using an applicator with a gap of 250 μm, it was cast and formed on a commercially available 200-μm-thick polyethylene terephthalate (PET) film. After air drying for 1 hour, it was treated at a temperature of 50 °C for 16 hours in a vacuum dryer (degree of vacuum: 1 Pa to 100 Pa) to remove the solvent, and a resin film with a film thickness of 20 μm in the coated portion was obtained. Regarding the charge transport composition film obtained above and the film obtained by further treating the same film in a vacuum dryer at a temperature of 150 °C for 1 hour, the abrasion resistance of the cast surface of the resin film was evaluated using a Suga Abrasion Tester NUS-ISO-3 type (manufactured by Suga Test Instruments Co., Ltd.). The test conditions were to bring an abrasive paper (containing alumina particles with a particle size of 3 μm) with a load of 4.9 N into contact with the cast surface (the surface simulating the photoreceptor layer surface) and perform 800 reciprocating motions, and measure the mass reduction amount (abrasion amount, unit: mg). The results obtained are shown in Table 1.

[0190] [Comparative Example 1] Instead of PC-1 and PC-2 in Example 2, a polycarbonate (PCA) having the following structure and a solution with a concentration of 0.5 g / dL was prepared, and a charge transport layer composition film was prepared using a polycarbonate (PCA) with a reduced viscosity [ηsp / C] of 1.19 dL / g at 20 °C, and the abrasion resistance was evaluated in the same manner as above. The results obtained are shown in Table 1.

[0191] [Chemical Formula]

[0192] [Table 1]

[0193] From the results shown in Table 1, it was confirmed that in Example 2, due to the polymerization reaction of PC-1 and PC-2 proceeding and the molecular weight increasing by heating at 150 °C, the abrasion amount was reduced by 47%, and the abrasion resistance of the reactive resin was excellent. In addition, since the wear amount of Example 2 is 9% smaller than that of Comparative Example 1, it was confirmed that this resin is excellent in wear resistance.

Claims

1. At least one resin selected from the group consisting of an aromatic polycarbonate and a polyarylate, comprising a structure represented by the following general formula (DE1): Resin. 【Chemical 1】 (In the general formula (DE1), R is, independently of each other, an aliphatic hydrocarbon group having 1 or more and 12 or less carbon atoms, an aromatic hydrocarbon group having 6 or more and 12 or less ring-forming carbon atoms, an alkoxy group having 1 or more and 10 or less carbon atoms, or a halogen atom, and a plurality of Rs may form a cyclic structure (including an aromatic ring and a heterocyclic ring) connected to each other, n represents an integer of 0 or more and 4 or less, m represents an integer of 0 or more and 9 or less.)

2. The resin according to claim 1, comprising a structure represented by the following general formula (S1): Resin. [Chemical 2]

3. A resin composition comprising the resin according to claim 1 and a compound or resin containing a dienophile structure. Resin composition.

4. In the resin composition according to claim 3, the dienophile structure comprises a structure represented by the following general formula (DP1): Resin composition. 【Chemical Formula 3】 (In the general formula (DP1), X ２ is a single bond or a linking group to another skeleton, X as the linking group ２ includes at least any one atom selected from the group consisting of a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom, and is a group in which all the bonding modes between the atoms constituting the linking group are covalent bonds.)

5. In the resin composition according to claim 3 or claim 4, the resin composition contains any one of the following components (i), the following component (ii), and the following component (iii): Resin composition. (i) A polymer having a structure represented by the general formula (DE1) in the polymer chain and a compound having a dienophile group (ii) A polymer having a structure represented by the general formula (DE1) in the polymer chain and a polymer having a dienophile structure in the polymer chain (iii) A polymer having both a structure represented by the general formula (DE1) and a dienophile structure in one polymer chain

6. A coating liquid composition comprising the resin composition according to any one of claims 3 to 5 and an organic solvent. Coating liquid composition.

7. A film comprising the resin according to claim 1 or claim 2. Film.

8. A coating film comprising the resin according to claim 1 or claim 2. Coating film.

9. An electrophotographic photoreceptor having a layer containing the resin according to claim 1 or claim 2. Electrophotographic photoreceptor.

10. An insulating material comprising the resin according to claim 1 or claim 2. Insulating material.

11. A molded article comprising the resin according to claim 1 or claim 2. Molded article.

12. An electronic device comprising the resin according to claim 1 or claim 2. Electronic device.

13. A step of performing a polymer reaction of the resin composition by heating the resin composition according to any one of claims 3 to 5, Method for producing resin.

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