Polycarbonate-polyarylate resin, coating composition, molded body, and electrophotographic photoreceptor

Abstract

Provided is a polycarbonate-polyarylate resin including at least one of structural units represented by general formulae (A1) and (A2), a structural unit represented by general formula (B1), and a structural unit represented by general formula (C1), the polycarbonate-polyarylate resin being such that the molar fraction ax of structural units represented by general formula (A1), the molar fraction ay of structural units represented by general formula (A2), and the molar fraction c of structural units represented by general formula (C1) satisfy the following mathematical formula (formula 1).　(Formula 1) 0.1 ≤ {(ax_ay) / (ax+ay+c)} ×100 < 50

Description

Polycarbonate polyarylate resin, coating composition, molded article, and electrophotographic photoreceptor

[0001] The present invention relates to a polycarbonate polyarylate resin, a coating composition, a molded article, and an electrophotographic photoreceptor.

[0002] Polycarbonate resins have been used in a variety of industrial fields due to their excellent mechanical and electrical properties. Various improvement techniques have been used to improve the properties of polycarbonate resins, broadening the range of applications for polycarbonate resins. One such improvement technique is block copolymerization. Block copolymerization is a method of chemically linking polymers with different structures, which can achieve higher performance than simple blends of polymers.

[0003] A known method for producing a block copolymer based on a polycarbonate resin is the transesterification method (Patent Document 1). The transesterification method involves melt-kneading different polycarbonates or a polycarbonate and a polyester in the presence of a transesterification catalyst to obtain a block copolymer. Patent Document 2 also proposes a method in which a phosphoric acid compound is added in the final stage of melt-kneading in the transesterification method.

[0004] JP 2012-158652 A JP 2011-074342 A

[0005] An example of a product utilizing the electrical and optical properties of polycarbonate resin is an electrophotographic photoreceptor that uses polycarbonate resin as a binder resin for functional materials such as charge-generating materials and charge-transporting materials. Electrophotographic photoreceptors are required to have predetermined sensitivity, electrical properties, and optical properties depending on the electrophotographic process. Furthermore, since various operations (e.g., corona charging, toner development, paper transfer, cleaning, etc.) are repeatedly performed on the surface of the photosensitive layer of an electrophotographic photoreceptor, at least one of electrical and mechanical external forces 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 must be wear-resistant to withstand these external forces. Furthermore, since electrophotographic photoreceptors are typically manufactured by dissolving a binder resin together with the charge-generating material and the like in an organic solvent and casting the resulting mixture on a conductive substrate, the polycarbonate resin must also be soluble in the organic solvent. In view of this, there is a demand for resins that have excellent solubility in organic solvents and also exhibit good abrasion resistance.

[0006] An object of the present invention is to provide a polycarbonate polyarylate resin that has excellent solubility in organic solvents and good abrasion resistance. Another object of the present invention is to provide a coating composition, a molded article, and an electrophotographic photoreceptor that contain the polycarbonate polyarylate resin.

[0007] As a result of extensive research, the present inventors have found that polycarbonate polyarylate resins having specific structural units have excellent solubility in organic solvents and also exhibit good abrasion resistance. That is, the gist of the present invention resides in the following [Configuration 1] to [Configuration 17].

[0008] [Configuration 1] A polycarbonate polyarylate resin containing at least one of structural units represented by the following general formulas (A1) and (A2), a structural unit represented by the following general formula (B1), and a structural unit represented by the following general formula (C1), wherein the molar fraction ax of the structural unit represented by the following general formula (A1), the molar fraction ay of the structural unit represented by the following general formula (A2), and the molar fraction c of the structural unit represented by the following general formula (C1) satisfy the following formula (1): 0.1≦{(ax+ay) / (ax+ay+c)}×100<50 ... (1)

[0009]

[0010] (In the general formulae (A1) and (A2), R １３ and R １４ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group; n represents 0, 1, 2, or 3; １３ are the same or different from each other, m represents 0, 1, 2, 3 or 4, and a plurality of R １４are the same or different from each other, in the general formula (B1), b is the mole fraction of the structural unit represented by the general formula (B1), the structural unit represented by the general formula (B1) is different from the carbonyl group in the general formulas (A1) and (A2), in the general formula (C1), Cx is a divalent group containing a substituted or unsubstituted divalent aromatic hydrocarbon group, with the proviso that Cx in the structural unit represented by the general formula (C1) does not consist solely of the divalent group represented by the following general formula (C3), * in the general formulas (A1), (A2), (B1) and (C1) represents a bond, when the polycarbonate polyarylate resin contains a plurality of structural units represented by the general formula (A1), the plurality of structural units represented by the general formula (A1) are the same or different from each other, when the polycarbonate polyarylate resin contains a plurality of structural units represented by the general formula (A2), the plurality of structural units represented by the general formula (A2) are the same or different from each other, When a plurality of structural units represented by the general formula (C1) are contained, the plurality of structural units represented by the general formula (C1) may be the same or different from each other.

[0011]

[0012] (In the general formula (C3), R １６１ ~R １６８are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, a cyano group, and a carboxy group; * represents a bond; and when a plurality of divalent groups represented by general formula (C3) are present, the plurality of divalent groups represented by general formula (C3) are the same or different. )

[0013] [Configuration 2] The polycarbonate polyarylate resin according to [Configuration 1], which contains a structural unit represented by the general formula (A1).

[0014] [Configuration 3] The polycarbonate polyarylate resin according to [Configuration 1] or [Configuration 2], which does not contain a structural unit represented by the general formula (A2).

[0015] [Configuration 4] The polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 3], wherein the structural unit represented by general formula (A1) includes at least one of structural units represented by the following general formulas (A11) and (A12):

[0016]

[0017] (R in the general formula (A11) １３１ ~R １３６ and R in the general formula (A12) １５１ ~R １５６are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group, In the general formula (A12), at represents the molar fraction of the structural unit represented by the general formula (A12), and * in the general formulas (A11) and (A12) represents a bond.

[0018] [Configuration 5] The polycarbonate polyarylate resin according to [Configuration 4], wherein the structural unit represented by the general formula (A1) includes a structural unit represented by the general formula (A11).

[0019] [Configuration 6] The polycarbonate polyarylate resin according to [Configuration 4] or [Configuration 5], wherein the molar fraction as of the structural unit represented by the general formula (A11) and the molar fraction at of the structural unit represented by the general formula (A12) satisfy the following mathematical formula (1B): 10≦{as / (as+at)}×100≦100 (Mathematical formula 1B).

[0020] [Configuration 7] The polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 6], wherein the structural unit represented by the general formula (C1) includes at least one of structural units represented by the following general formulas (C11) and (C12):

[0021]

[0022] (R in the general formula (C11) １７１ ~R １７８ and R in the general formula (C12) １７９ ~R １８２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; R １７１ ~R １７８ and R １７９ ~R １８２ are the same or different, X is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), cx in the general formula (C11) is the molar fraction of the structural unit represented by the general formula (C11), cy in the general formula (C12) is the molar fraction of the structural unit represented by the general formula (C12), and * in the general formulas (C11) and (C12) represents a bond.

[0023] [Configuration 8] The polycarbonate polyarylate resin according to [Configuration 7], wherein the structural unit represented by the general formula (C1) includes a structural unit represented by the general formula (C11).

[0024] [Configuration 9] The polycarbonate polyarylate resin according to [Configuration 7] or [Configuration 8], wherein the structural unit represented by the general formula (C1) includes a structural unit represented by the following general formula (C111):

[0025]

[0026] (In the general formula (C111), R １７１ ~R １７８ , cx, and * respectively represent R in the general formula (C11). １７１ ~R １７８ , cx and *, R １２１ ~R １３０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * represents a bond.

[0027] [Configuration 10] The polycarbonate polyarylate resin according to [Configuration 1], wherein the structural unit represented by general formula (A1) includes a structural unit represented by the following general formula (A11), and the structural unit represented by general formula (C1) includes a structural unit represented by the following general formula (C111).

[0028]

[0029] (R in the general formula (A11) １３１ ~R １３６are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group, in general formula (A11) as is the mole fraction of the structural unit represented by general formula (A11), * in general formula (A11) represents a bond, １７１ ~R １７８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, cx in general formula (C111) is the mole fraction of the structural unit represented by general formula (C111), and R １２１ ~R １３０ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * in general formula (C111) represents a bond.

[0030] [Configuration 11] The polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 10], wherein the reduced viscosity [ηsp / C] is 0.15 dL / g or more and 5.75 dL / g or less.

[0031] [Configuration 12] A coating composition containing the polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 11] and an organic solvent.

[0032] [Configuration 13] The coating composition according to [Configuration 12], further comprising a charge transport material.

[0033] [Configuration 14] A molded article comprising the polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 11].

[0034] [Configuration 15] An electrophotographic photoreceptor comprising the polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 11] in its outermost layer.

[0035] [Configuration 16] An electrophotographic photoreceptor comprising a conductive substrate and a photosensitive layer provided on the conductive substrate, the photosensitive layer containing the polycarbonate polyarylate resin according to any one of [Configuration 1] to [Configuration 11].

[0036] [Configuration 17] The electrophotographic photoreceptor according to [Configuration 16], wherein the photosensitive layer has a charge transport layer and a charge generation layer disposed between the charge transport layer and the conductive substrate, and the charge transport layer contains the polycarbonate polyarylate resin.

[0037] According to one aspect of the present invention, it is possible to provide a polycarbonate polyarylate resin that has excellent solubility in organic solvents and good abrasion resistance. According to one aspect of the present invention, it is possible to provide a coating composition, a molded article, and an electrophotographic photoreceptor that contain the polycarbonate polyarylate resin according to one aspect of the present invention.

[0038] [First Embodiment] [Polycarbonate Polyarylate Resin] The polycarbonate polyarylate resin according to this embodiment contains at least one of structural units represented by the following general formulas (A1) and (A2), a structural unit represented by the following general formula (B1), and a structural unit represented by the following general formula (C1). In this specification, the polycarbonate polyarylate resin may be abbreviated as PC-PAR resin. In the PC-PAR resin according to this embodiment, the molar fraction ax of the structural unit represented by the following general formula (A1), the molar fraction ay of the structural unit represented by the following general formula (A2), and the molar fraction c of the structural unit represented by the following general formula (C1) preferably satisfy the following mathematical formula (1): 0.1≦{(ax+ay) / (ax+ay+c)}×100<50 (Math 1)

[0039]

[0040] (In the general formulae (A1) and (A2), R １３ and R １４ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group; n represents 0, 1, 2, or 3; １３ are the same or different from each other, m represents 0, 1, 2, 3 or 4, and a plurality of R １４are the same or different from each other, in the general formula (B1), b is the mole fraction of the structural unit represented by the general formula (B1), the structural unit represented by the general formula (B1) is different from the carbonyl group in the general formulas (A1) and (A2), in the general formula (C1), Cx is a divalent group containing a substituted or unsubstituted divalent aromatic hydrocarbon group, with the proviso that Cx in the structural unit represented by the general formula (C1) does not consist solely of the divalent group represented by the following general formula (C3), * in the general formulas (A1), (A2), (B1) and (C1) represents a bond, when the polycarbonate polyarylate resin contains a plurality of structural units represented by the general formula (A1), the plurality of structural units represented by the general formula (A1) are the same or different from each other, when the polycarbonate polyarylate resin contains a plurality of structural units represented by the general formula (A2), the plurality of structural units represented by the general formula (A2) are the same or different from each other, When a plurality of structural units represented by the general formula (C1) are contained, the plurality of structural units represented by the general formula (C1) may be the same or different from each other.

[0041]

[0042] (In the general formula (C3), R １６１ ~R １６８are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, a cyano group, and a carboxy group; * represents a bond; and when a plurality of divalent groups represented by general formula (C3) are present, the plurality of divalent groups represented by general formula (C3) are the same or different. )

[0043] In the PC-PAR resin according to this embodiment, the structures of structural units that have the same general formula are different from each other, meaning that the structures are different due to, for example, differences in constituent atoms, bonding sites, ring structures, linking groups, and substituents.

[0044] In the resin according to this embodiment, the structural units represented by the general formula (A1) are not bonded to each other in succession, the structural units represented by the general formula (A2) are not bonded to each other in succession, the structural units represented by the general formula (B1) are not bonded to each other in succession, and the structural units represented by the general formula (C1) are not bonded to each other in succession.

[0045] From the viewpoint of improving abrasion resistance, the PC-PAR resin according to this embodiment preferably satisfies the following mathematical formula (Mathematical Formula 2), more preferably satisfies mathematical formula (Mathematical Formula 3), even more preferably satisfies mathematical formula (Mathematical Formula 4), even more preferably satisfies mathematical formula (Mathematical Formula 5), ​​and even more preferably satisfies mathematical formula (Mathematical Formula 6). 10≦{(ax+ay) / (ax+ay+c)}×100≦48…(Math. 2) 15≦{(ax+ay) / (ax+ay+c)}×100≦45…(Math. 3) 20≦{(ax+ay) / (ax+ay+c)}×100≦43…(Math. 4) 20<{(ax+ay) / (ax+ay+c)}×100≦43…(Math. 5) 30≦{(ax+ay) / (ax+ay+c)}×100≦43…(Math. 6)

[0046] The molar fraction of each structural unit or repeating unit in the PC-PAR resin according to this embodiment is calculated by nuclear magnetic resonance (NMR) measurement. １ H NMR measurement is carried out, and the value is calculated from the peak integral value derived from each structural unit or repeating unit.

[0047] The PC-PAR resin according to this embodiment preferably contains a structural unit represented by the general formula (A1).

[0048] The PC-PAR resin according to this embodiment preferably contains a repeating unit represented by the following general formula (PAR-AC1).

[0049]

[0050] (In the general formula (PAR-AC1), R １３ and n are each R in the general formula (A1). １３ and n, and a plurality of R １３ are the same or different from each other, Cx has the same meaning as Cx in the general formula (C1), and * represents a bond.

[0051] The PC-PAR resin according to this embodiment also preferably contains a repeating unit represented by the following general formula (PAR-AC2).

[0052]

[0053] (In the general formula (PAR-AC2), R １４ and m are each R in the general formula (A2). １４ and m, and a plurality of R １４ are the same or different from each other, Cx has the same meaning as Cx in the general formula (C1), and * represents a bond.

[0054] In the PC-PAR resin according to this embodiment, R in the general formulas (A1) and (A2) １３ and R １４ are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and more preferably a hydrogen atom.

[0055] The PC-PAR resin according to this embodiment preferably contains a repeating unit represented by the following general formula (PC-BC1).

[0056]

[0057] (In the general formula (PC-BC1), Cx has the same meaning as Cx in the general formula (C1), and * represents a bond.)

[0058] The PC-PAR resin according to this embodiment preferably contains a repeating unit represented by the following general formula (PC-BC2).

[0059]

[0060] (In the general formula (PC-BC2), Cx １ and Cx ２ are each independently defined as Cx in formula (C1), and * represents a bond.

[0061] In the general formula (PC-BC2), Cx １ and Cx ２ are the same as or different from each other, and are preferably the same as each other.

[0062] It is also preferable that the PC-PAR resin according to this embodiment does not contain a structural unit represented by the general formula (A2), i.e., the molar fraction ay is 0 (zero).

[0063] In the PC-PAR resin according to this embodiment, the structural unit represented by the general formula (A1) preferably includes at least one of structural units represented by the following general formulas (A11) and (A12).

[0064]

[0065] (R in the general formula (A11) １３１ ~R １３６ and R in the general formula (A12) １５１ ~R １５６ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group, In the general formula (A12), at represents the molar fraction of the structural unit represented by the general formula (A12), and * in the general formulas (A11) and (A12) represents a bond.

[0066] When the PC-PAR resin according to this embodiment contains at least one of the structural units represented by general formulas (A11) and (A12), from the viewpoint of improving abrasion resistance, the PC-PAR resin according to this embodiment preferably satisfies any one of the following formulas (1A) to (4A), more preferably satisfies formula (5A), and even more preferably satisfies formula (6A). 0.1≦{(as+at+ay) / (as+at+ay+c)}×100<50…(Math 1A) 10≦{(as+at+ay) / (as+at+ay+c)}×100≦48…(Math 2A) 15≦{(as+at+ay) / (as+at+ay+c)}×100≦45…(Math 3A) 20≦{(as+at+ay) / (as+at+ay+c)}×100≦43…(Math 4A) 20<{(as+at+ay) / (as+at+ay+c)}×100≦43…(Math. 5A) 30≦{(as+at+ay) / (as+at+ay+c)}×100≦43…(Math. 6A)

[0067] When the PC-PAR resin according to this embodiment contains at least one of the structural units represented by general formula (A11) and (A12), the PC-PAR resin according to this embodiment preferably satisfies any one of the following mathematical formulas (1B) to (4B): 10≦{as / (as+at)}×100≦100 (Mathematical Formula 1B) 80≦{as / (as+at)}×100≦100 (Mathematical Formula 2B) 30≦{as / (as+at)}×100≦80 (Mathematical Formula 3B) 40≦{as / (as+at)}×100≦60 (Mathematical Formula 4B) In the PC-PAR resin according to this embodiment, the more structural units represented by general formula (A11) there are, the more excellent the abrasion resistance becomes. In the PC-PAR resin according to this embodiment, the more structural units represented by general formula (A12) there are, the more excellent the solubility and elongation at break become.

[0068] In the PC-PAR resin according to this embodiment, it is preferable that the molar fraction as and the molar fraction at do not become 0 (zero) at the same time.

[0069] In the PC-PAR resin according to this embodiment, the structural unit represented by the general formula (A1) preferably includes a structural unit represented by the general formula (A11).

[0070] The PC-PAR resin according to this embodiment preferably contains a repeating unit represented by the following general formula (PAR-AC11).

[0071]

[0072] (In the general formula (PAR-AC11), R １３１ ~R １３６ are R in the general formula (A11), respectively. １３１ ~R １３６ Cx has the same meaning as Cx in general formula (C1), and * represents a bond.

[0073] The PC-PAR resin according to this embodiment preferably contains a repeating unit represented by the following general formula (PAR-AC12).

[0074]

[0075] (In the general formula (PAR-AC12), R １５１ ~R １５６ are R in the general formula (A12), respectively. １５１ ~R １５６ Cx has the same meaning as Cx in general formula (C1), and * represents a bond.

[0076] In the PC-PAR resin according to this embodiment, R １３１ ~R １３６ and R in (A12) １５１ ~R １５６ are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and more preferably a hydrogen atom.

[0077] In the PC-PAR resin according to this embodiment, it is also preferable that the structural unit represented by general formula (A1) does not include the structural unit represented by general formula (A12), i.e., the molar fraction at is 0 (zero).

[0078] In the PC-PAR resin according to this embodiment, it is also preferable that the structural unit represented by general formula (A1) includes both the structural unit represented by general formula (A11) and the structural unit represented by general formula (A12).

[0079] In the PC-PAR resin according to this embodiment, the structural unit represented by the general formula (C1) preferably includes at least one of structural units represented by the following general formulas (C11) and (C12).

[0080]

[0081] (R in the general formula (C11) １７１ ~R １７８ and R in the general formula (C12) １７９ ~R １８２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; R １７１ ~R １７８ and R １７９ ~R １８２ are the same or different, X is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２(iii) a divalent group formed by linking two or more groups selected from the group (ii), cx in the general formula (C11) is the molar fraction of the structural unit represented by the general formula (C11), cy in the general formula (C12) is the molar fraction of the structural unit represented by the general formula (C12), and * in the general formulas (C11) and (C12) represents a bond.

[0082] In one aspect of the PC-PAR resin according to this embodiment, the structural unit represented by the general formula (B1) is different from the carbonyl groups in the general formulae (A1), (A2), and (C1).

[0083] In the PC-PAR resin according to this embodiment, the structural unit represented by the general formula (C1) preferably includes a structural unit represented by the general formula (C11).

[0084] In the PC-PAR resin according to this embodiment, Cx is preferably a divalent group represented by the following general formula (CX101) or (CX102).

[0085]

[0086] (R in the general formula (CX101) １７１ ~R １７８ and X are each R in the general formula (C11). １７１ ~R １７８ and X, and R in general formula (CX102) １７９ ~R １８２ are R in the general formula (C12), respectively. １７９ ~R １８２ and * represents a bond.)

[0087] In the PC-PAR resin according to this embodiment, Cx is preferably a divalent group represented by the general formula (CX101) above.

[0088] In the PC-PAR resin according to this embodiment, the structural unit represented by general formula (C1) preferably includes a structural unit represented by the following general formula (C111):

[0089]

[0090] (In the general formula (C111), R １７１ ~R １７８ , cx, and * respectively represent R in the general formula (C11). １７１ ~R １７８ , cx and *, R １２１ ~R １３０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * represents a bond.

[0091] In the PC-PAR resin according to this embodiment, it is preferable that the structural unit represented by general formula (A1) includes a structural unit represented by general formula (A11), and the structural unit represented by general formula (C1) includes a structural unit represented by general formula (C111).

[0092] In the PC-PAR resin according to this embodiment, Cx is preferably a divalent group represented by the following general formula (CX111).

[0093]

[0094] (In the general formula (CX111), R １７１ ~R １７８ are R in the general formula (C11), respectively. １７１ ~R １７８ is synonymous with R １２１ ~R １３０ are R in the general formula (C111), respectively. １２１ ~R １３０ and * represents a bond.)

[0095] In the PC-PAR resin according to this embodiment, R １７１ ~R １７８ and R in the general formula (C12) １７９~R １８２ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms.

[0096] In the PC-PAR resin according to this embodiment, R １７１ , R １７４ , R １７６ and R １７７ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms.

[0097] In the PC-PAR resin according to this embodiment, R １７１ , R １７４ , R １７６ and R １７７ are preferably each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0098] In the PC-PAR resin according to this embodiment, R １７１ and R １７４ is a hydrogen atom, and R １７１ and R １７４ the other is a substituent other than a hydrogen atom, and R １７６ and R １７７ is a hydrogen atom, and R １７６ and R １７７ The other is preferably a substituent other than a hydrogen atom.

[0099] In the PC-PAR resin according to this embodiment, R １７１ and R １７４ is a hydrogen atom, and R １７１ and R １７４ the other is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and R １７６ and R １７７ is a hydrogen atom, and R １７６and R １７７ The other is preferably a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0100] In the PC-PAR resin according to this embodiment, R １７２ , R １７３ , R １７５ and R １７８ is preferably a hydrogen atom.

[0101] The PC-PAR resin according to this embodiment may contain structural units other than the structural units described above. Examples of such structural units include a terminal structure derived from a terminal terminator described below and a structural unit containing a silicon atom. Furthermore, the PC-PAR resin according to this embodiment may contain the structural units described above and a terminal structure derived from a terminal terminator described below, and may not contain other structural units.

[0102] The reduced viscosity [ηsp / C] of the PC-PAR resin according to this embodiment is preferably 0.15 dL / g or more and 5.75 dL / g or less. The reduced viscosity [ηsp / C] of the PC-PAR resin according to this embodiment is preferably 0.27 dL / g or more, and more preferably 1.20 dL / g or more. The reduced viscosity [ηsp / C] of the PC-PAR resin according to this embodiment is preferably 5.20 dL / g or less, and more preferably 3.00 dL / g or less. In this specification, the reduced viscosity is measured as follows: A methylene chloride solution containing the resin to be measured at a concentration of 0.5 g / dL is prepared, and the reduced viscosity of this methylene chloride solution at 20.0°C is measured using an Ubbelohde viscometer.

[0103] (Explanation of Substituents, etc.) In the PC-PAR resin according to this embodiment, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0104] In the PC-PAR resin according to this embodiment, examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, butyl, sec-butyl, tert-butyl, various pentyl groups, and various hexyl groups. In this specification, when the term "various" is used in conjunction with the name of a substituent, this term includes linear and branched groups, and the same applies hereinafter. In the PC-PAR resin according to this embodiment, examples of the substituted alkyl group include trifluoromethyl. In the PC-PAR resin according to this embodiment, the alkyl group preferably has, for example, 1 to 28 carbon atoms, 1 to 20 carbon atoms, 1 to 18 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms.

[0105] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0106] In the PC-PAR resin according to this embodiment, examples of the alkylene group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a hexamethylene group. In the PC-PAR resin according to this embodiment, the number of carbon atoms in the alkylene group is preferably, for example, 1 to 28, 1 to 20, 1 to 18, 1 to 10, or 1 to 5.

[0107] In the PC-PAR resin according to this embodiment, examples of the alkylidene group include an ethylidene group and an isopropylidene group. In the PC-PAR resin according to this embodiment, the alkylidene group preferably has 2 to 28, 2 to 20, 2 to 18, 2 to 10, or 2 to 5 carbon atoms.

[0108] In the PC-PAR resin according to this embodiment, examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, various pentyloxy groups, and various hexyloxy groups. In the PC-PAR resin according to this embodiment, the alkoxy group has, for example, 1 to 18 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms.

[0109] In the PC-PAR resin according to this embodiment, examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, and a norbornyl group. In the PC-PAR resin according to this embodiment, the cycloalkyl group preferably has, for example, 3 to 26 ring carbon atoms, 3 to 20 ring carbon atoms, or 6 to 20 ring carbon atoms.

[0110] In the PC-PAR resin according to this embodiment, examples of the cycloalkylene group include a cyclopentanediyl group, a cyclohexanediyl group, and a cyclooctanediyl group. In the PC-PAR resin according to this embodiment, the cycloalkylene group preferably has, for example, 5 to 15 ring carbon atoms, or 5 to 10 ring carbon atoms.

[0111] In the PC-PAR resin according to this embodiment, examples of the cycloalkylidene group include a cyclohexylidene group, a 3,5,5-trimethylcyclohexylidene group, and a 2-adamantylidene group. In the PC-PAR resin according to this embodiment, the number of ring carbon atoms of the cycloalkylidene group is preferably, for example, 3 to 26, 5 to 15, or 5 to 10.

[0112] In the PC-PAR resin according to this embodiment, the cycloalkoxy group may be, for example, a group in which the cycloalkyl group moiety is the cycloalkyl group described above, i.e., a group in which Arx of the group represented by -O-Arx is the cycloalkyl group described above. In the PC-PAR resin according to this embodiment, the cycloalkoxy group preferably has 3 to 20 ring carbon atoms or 6 to 20 ring carbon atoms.

[0113] In the PC-PAR resin according to this embodiment, examples of the alkenyl group include ethenyl (vinyl), 1-propenyl, 2-propenyl (allyl), butenyl, pentenyl, and hexenyl groups. In the PC-PAR resin according to this embodiment, the number of carbon atoms in the alkenyl group is preferably, for example, 2 to 10, or 2 to 6.

[0114] In the PC-PAR resin according to this embodiment, examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, and a 3-hexynyl group. In the PC-PAR resin according to this embodiment, the number of carbon atoms in the alkynyl group is preferably, for example, 2 to 10 or 2 to 6.

[0115] In the PC-PAR resin according to this embodiment, examples of the aryl group include a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. In the PC-PAR resin according to this embodiment, examples of the substituted aryl group include a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a dichlorophenyl group, and a methylnaphthyl group. In the PC-PAR resin according to this embodiment, the number of ring carbon atoms of the aryl group is preferably 6 to 20, for example, 6 to 14, or 6 to 10.

[0116] In the PC-PAR resin according to this embodiment, examples of the arylene group include a phenylene group, a naphthylene group, an anthracenediyl group, a biphenylene group, and a terphenyldiyl group. In one aspect of the PC-PAR resin according to this embodiment, the number of ring carbon atoms of the arylene group is preferably, for example, 6 to 20, 6 to 14, or 6 to 10.

[0117] In the PC-PAR resin according to this embodiment, examples of the aryloxy group include a phenoxy group and a naphthyloxy group. In the PC-PAR resin according to this embodiment, examples of the substituted aryloxy group include a tolyloxy group. In the PC-PAR resin according to this embodiment, the number of ring carbon atoms of the aryloxy group is, for example, preferably 6 to 14, or 6 to 10.

[0118] In the PC-PAR resin according to this embodiment, examples of the aralkyl group include a phenylmethyl group and a phenylethyl group. In the PC-PAR resin according to this embodiment, the number of carbon atoms in the aralkyl group is preferably, for example, 7 to 20 or 7 to 15.

[0119] In the PC-PAR resin according to this embodiment, the aralkyloxy group may be, for example, an aralkyl group moiety, i.e., an aralkyl group in the group represented by -O-Ary, where Ary is the aralkyl group. In the PC-PAR resin according to this embodiment, the number of carbon atoms in the aralkyloxy group is preferably, for example, 7 to 20 or 7 to 15.

[0120] In the PC-PAR resin according to this embodiment, examples of the monovalent aromatic hydrocarbon group include the aryl group described above. In the PC-PAR resin according to this embodiment, examples of the divalent aromatic hydrocarbon group include a divalent group derived by removing one hydrogen atom from the aryl ring of the aryl group described above.

[0121] In the PC-PAR resin according to this embodiment, the monovalent cycloaliphatic hydrocarbon group may be, for example, a saturated or unsaturated alicyclic group. The alicyclic group may have, for example, 3 to 20 carbon atoms, preferably 3 to 12 carbon atoms, and more preferably 4 to 8 carbon atoms. Specific examples of the saturated or unsaturated alicyclic group include cycloalkyl groups, which are saturated alicyclic groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl, and cycloalkenyl groups, which are unsaturated alicyclic groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl. Note that the unsaturated alicyclic group does not contain an aromatic group. In the PC-PAR resin according to this embodiment, the divalent cycloaliphatic hydrocarbon group may be, for example, a divalent group derived by removing one hydrogen atom from the ring of the saturated or unsaturated alicyclic group.

[0122] In the PC-PAR resin according to this embodiment, examples of the monovalent chain aliphatic hydrocarbon group include the alkyl groups described above.

[0123] In the PC-PAR resin according to this embodiment, the divalent chain aliphatic hydrocarbon group is, for example, a divalent group derived by removing one hydrogen atom from the alkyl chain of the alkyl group.

[0124] In this specification, when referring to "substituted or unsubstituted," the substituents may bond to each other to form a monocycle, a fused ring, or not bond to each other. Here, when referring to "substituted or unsubstituted," the substituents may bond to each other to form a monocycle or a fused ring, and this also includes cases where the substituents bond to each other to form a multi-membered ring. This multi-membered ring is preferably a two-membered ring (bicyclo), a three-membered ring (tricyclo), or a four-membered ring (tetracyclo). For example, when referring to a "substituted or unsubstituted" group (a cycloalkyl group, a cycloalkylene group, a cycloalkylidene group) derived from a cycloalkane, examples of when the substituents bond to each other to form a multi-membered ring include monovalent or divalent groups derived from a bicycloalkane, a tricycloalkane, and a tetracycloalkane.

[0125] In this specification, the substituents in the "substituted" part of "substituted or unsubstituted" are preferably at least one substituent selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, an aryloxy group, and a halogen atom, each independently. Specific examples of these substituents include the same groups as the specific examples described above. Furthermore, in this specification, "unsubstituted" in the "substituted or unsubstituted" part means that the group is not substituted with the substituent and is bonded to a hydrogen atom.

[0126] In the present specification, in specific examples of compounds, D may represent a deuterium atom, Me may represent a methyl group, Ph may represent a phenyl group, and tBu may represent a tert-butyl group.

[0127] In this specification, the preferred definitions can be adopted arbitrarily, and it can be said that a combination of preferred definitions is more preferred.

[0128] [Method for producing polycarbonate polyarylate resin] A method for producing a polycarbonate polyarylate resin according to this embodiment will be described. The PC-PAR resin according to this embodiment contains a polyarylate-based repeating unit and a polycarbonate-based repeating unit. The polyarylate-based repeating unit contains at least one of the structural units represented by the general formulas (A1) and (A2). The polycarbonate-based repeating unit contains a structural unit represented by the general formula (C1).

[0129] The PC-PAR resin according to this embodiment can be produced by a known method for producing a polyester polycarbonate resin, using, for example, at least one of dicarboxylic acid compounds (ma) represented by the following general formulas (MA1) and (MA2) and a dihydric phenol compound (mc) represented by the following general formula (MC1). The PC-PAR resin according to this embodiment can be produced, if necessary, in the presence of at least one additive component selected from the group consisting of an acid binder, a catalyst, a molecular weight modifier (such as a terminal capping agent or a branching agent), and a solvent.

[0130] Examples of methods for producing the PC-PAR resin according to this embodiment include a melt polymerization method in which bisphenol, dicarboxylic acid, and diphenyl carbonate are subjected to a transesterification reaction in the presence of a non-solvent and a basic catalyst, and an interfacial polymerization method in which bisphenol, dicarboxylic acid, and phosgene are reacted in the presence of an organic solvent inert to the reaction and an aqueous basic solution, and then a polymerization catalyst such as a tertiary amine or a quaternary ammonium salt is added to polymerize the resulting mixture. Another example of a method for producing the PC-PAR resin according to this embodiment is a method in which bisphenol, dicarboxylic acid chloride, and a polycarbonate oligomer are subjected to interfacial polycondensation in the presence of a water-insoluble organic solvent and an aqueous basic compound solution. This method is preferred because it is simple, does not cause side reactions, and allows for easy molecular weight control.

[0131] In the method for producing a PC-PAR resin according to this embodiment, in the case of interfacial polymerization, a pre-prepared polycarbonate oligomer (described below) is dissolved in a water-insoluble organic solvent (e.g., methylene chloride), and an alkaline compound aqueous solution of a dihydric phenol compound (e.g., sodium hydroxide aqueous solution) and a solution or suspension of a dicarboxylic acid compound or a derivative of a dicarboxylic acid compound dissolved in a water-insoluble organic solvent (e.g., methylene chloride) are added. The resulting mixture is then subjected to interfacial polycondensation using a tertiary amine (e.g., triethylamine) or a quaternary ammonium salt (e.g., trimethylbenzylammonium chloride) as a polymerization catalyst, and optionally in the presence of a terminal terminator (a monohydric phenol such as p-tert-butylphenol). Alternatively, in the case of the interfacial polymerization method, a PC-PAR resin according to this embodiment can be produced by copolymerizing a dihydric phenol compound, a dicarboxylic acid compound, and phosgene, a carbonate ester, or a chloroformate.

[0132] Polycarbonate oligomers can be produced by reacting a dihydric phenol compound with a carbonate precursor (e.g., phosgene, triphosgene, etc.) in an organic solvent such as methylene chloride, chlorobenzene, chloroform, etc. When producing a polycarbonate oligomer using the transesterification method, it can also be produced by reacting a dihydric phenol compound with a carbonate precursor such as diphenyl carbonate.

[0133] (Dicarboxylic acid compound (ma)) In the method for producing a PC-PAR resin according to this embodiment, dicarboxylic acid compounds (ma) represented by the following general formulae (MA1) and (MA2) can be used as dicarboxylic acid compounds for constituting repeating units derived from dicarboxylic acids.

[0134]

[0135] (In the general formula (MA1), R １３ and n are each R in the general formula (A1). １３ and n, and a plurality of R １３ are the same or different from each other, and in the general formula (MA2), R１４ and m are each R in the general formula (A2). １４ and m, and a plurality of R １４ are the same or different from each other.)

[0136] In the method for producing a PC-PAR resin according to this embodiment, it is preferable to use at least one selected from the group consisting of dicarboxylic acid compounds represented by the following general formulas (MA11) and (MA12) as the dicarboxylic acid compound (ma) for constituting a repeating unit derived from a dicarboxylic acid.

[0137]

[0138] (In the general formula (MA11), R １３１ ~R １３６ are R in the general formula (A11), respectively. １３１ ~R １３６ and in the general formula (MA12), R １５１ ~R １５６ are R in the general formula (A12), respectively. １５１ ~R １５６ is synonymous with

[0139] In the method for producing a PC-PAR resin according to this embodiment, the dicarboxylic acid compound (ma) may be used in combination with another dicarboxylic acid compound (mb). For example, as the dicarboxylic acid compound (mb), a known dicarboxylic acid compound or a dicarboxylic acid compound represented by the following general formula (MA3) may be used.

[0140]

[0141] (In the general formula (MA3), R ２１１ ~R ２１８are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, a cyano group, and a carboxy group; ２ is (i) a single bond, or (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii) above.

[0142] In the method for producing a PC-PAR resin according to this embodiment, the dicarboxylic acid may be derivatized before use. Examples of derivatives of the dicarboxylic acid compound (ma) and the dicarboxylic acid compound (mb) include, for example, dicarboxylic acid dichloride, dicarboxylic acid dimethyl ester, dicarboxylic acid diethyl ester, and dicarboxylic acid anhydride. A dicarboxylic acid dichloride is a compound in which two "-C(=O)-OH" groups in a dicarboxylic acid are substituted with "-C(=O)-Cl" groups. For example, the dichlorides of the dicarboxylic acid compounds (ma) represented by the general formulae (MA1) and (MA2) are represented by the following general formulae (MA1-CL) and (MA2-CL), respectively.

[0143]

[0144] (In the general formula (MA1-CL), R １３ and n are each R in the general formula (A1). １３ and n, and a plurality of R １３ are the same or different, and in the general formula (MA2-CL), R １４ and m are each R in the general formula (A2). １４ and m, and a plurality of R １４ are the same or different from each other.)

[0145] (Dihydric phenol compound (mc)) In the method for producing a PC-PAR resin according to this embodiment, the dihydric phenol includes a dihydric phenol compound (mc) represented by the general formula (MC1) from which a structural unit represented by the following general formula (C1) is derived.

[0146]

[0147] (In the general formula (MC1), Cx has the same meaning as Cx in the general formula (C1).)

[0148] Examples of the dihydric phenol compound (mc) include bis(hydroxyphenyl)alkane dihydric phenols, bis(hydroxyphenyl)cycloalkane dihydric phenols, dihydroxybiphenyl compounds, dihydroxybenzene compounds, dihydroxynaphthalene compounds, bis(4-hydroxyphenyl)oxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-methylphenyl)sulfide, bis(4-hydroxyphenyl)ether, bis(3-fluoro-4-hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxy-3-methylphenyl)sulfone, bis(4-hydroxyphenyl)sulfoxide, and 4,4'-dihydroxybenzophenone.

[0149] (Bis(hydroxyphenyl)alkane-based dihydric phenols) Examples of bis(hydroxyphenyl)alkane-based dihydric phenols include bis(4-hydroxyphenyl)methane, bis(4-hydroxy-3-methylphenyl)methane, 1,1-bis(4-hydroxyphenyl)-1,1-diphenylmethane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)-1-phenylmethane, 1,1-bis(4-hydroxyphenyl)-1-phenylmethane, bis(3-chloro-4-hydroxyphenyl)methane, bis(3,5-dibromo-4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)-1-phenylmethane, bis(3-chloro-4-hydroxyphenyl)methane, bis(3,5-dibromo-4-hydroxyphenyl)methane, bis( ... , 1-bis(4-hydroxyphenyl)ethane, 1,2-bis(4-hydroxyphenyl)ethane, 2-(4-hydroxy-3-methylphenyl)-2-(4-hydroxyphenyl)-1-phenylethane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 1,1-bis(2-tert-butyl-4-hydroxy-3-methylphenyl)ethane, 1-phenyl-1,1-bis(3-fluoro-4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane [bisphenol A (BPA)], 2,2- Bis(4-hydroxy-3,5-dimethylphenyl)propane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)propane, 1,1-bis(4-hydroxy-3-phenylphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-2-methylphenyl)propane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)propane, 2,2-bis(3-chloro-4-hydroxyphenyl)propane, 2,2-bis(3-fluoro-4-hydroxyphenyl)propane 2,2-bis(3-bromo-4-hydroxyphenyl)propane, 2,2-bis(3,5-difluoro-4-hydroxyphenyl)propane, 2,2-bis(3,5-dichloro-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(3-bromo-4-hydroxy-5-chlorophenyl)propane, 2,2-bis(3-hydroxyphenyl)hexafluoropropane, 2,2-bis(3-phenyl-4-hydroxyphenyl)propane, 1,Examples of such hydroxyphenyl esters include 1-bis(2-butyl-4-hydroxy-5-methylphenyl)butane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)butane, 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)isobutane, 1,1-bis(2-tert-amyl-4-hydroxy-5-methylphenyl)butane, 2,2-bis(4-hydroxy-3-methylphenyl)butane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(3,5-dichloro-4-hydroxyphenyl)butane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 4,4-bis(4-hydroxyphenyl)heptane, and 1,1-bis(2-tert-butyl-4-hydroxy-5-methylphenyl)heptane.

[0150] (Bis(hydroxyphenyl)cycloalkane dihydric phenol) Examples of bis(hydroxyphenyl)cycloalkane dihydric phenols include 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3-phenyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxy-3-phenylphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)cyclododecane, 1,1-bis(4-hydroxy-3-methylphenyl)cyclododecane, and 1,1-bis(4-hydroxy-3,5-dimethylphenyl)cyclododecane.

[0151] (Dihydroxybiphenyl Compound) Examples of dihydroxybiphenyl compounds include 4,4'-dihydroxybiphenyl, 3,3'-difluoro-4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-3,3'-dimethylbiphenyl, 4,4'-dihydroxy-2,2'-dimethylbiphenyl, 4,4'-dihydroxy-2,2',5,5'-dimethylbiphenyl, and 4,4'-dihydroxy-3,3'-dicyclohexylbiphenyl.

[0152] (Dihydroxybenzene Compound) Examples of dihydroxybenzene compounds include hydroquinone, resorcinol, and catechol.

[0153] (Dihydroxynaphthalene Compound) Examples of the dihydroxynaphthalene compound include 2,6-dihydroxynaphthalene and 1,4-dihydroxynaphthalene.

[0154] These dihydric phenol compounds (mc) may be used singly or in combination of two or more.

[0155] A specific example of a reaction type suitable for producing the PC-PAR resin according to this embodiment is two-stage polymerization in which the following steps (P3-1) and (P3-2) are carried out.

[0156] <Step (P3-1)> The first step (P3-1) is a step of synthesizing a polycarbonate oligomer using a part of the dihydric phenol compound (mc) and a carbonate ester-forming compound.

[0157] <Step (P3-2)> The second step, step (P3-2), is a step of mixing the polycarbonate oligomer synthesized in step (P3-1) with a reaction system comprising the remainder of the dihydric phenol compound (mc) and the dicarboxylic acid compound (ma) or a derivative thereof to carry out a polycondensation reaction.

[0158] In the method for producing a PC-PAR resin according to this embodiment, the polycarbonate oligomer can be synthesized in the first step (P3-1) by the following synthesis methods (P3-1a) and (P3-1b).

[0159] <Synthesis Method (P3-1a)> Synthesis Method (P3-1a) is a method of carrying out a polycondensation reaction in the presence of a suitable acid binder using a carbonyl dihalide, a haloformate, a carbonate ester compound, or the like as a carbonate ester-forming compound. Examples of the carbonyl dihalide include phosgene, and examples of the haloformates include chloroformate compounds.

[0160] The polycondensation reaction using the carbonyl dihalide, haloformates, or carbonate compounds as the carbonate-forming compound in the presence of an acid binder is usually carried out in a solvent. The proportion of the carbonate-forming compound used may be appropriately adjusted taking into account the stoichiometric ratio (equivalents) of the reaction. When a gaseous carbonate-forming compound such as phosgene is used, it is preferable to blow it into the reaction system.

[0161] Examples of the acid binder used in the synthesis method (P3-1a) include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, organic bases such as pyridine, and mixtures thereof. The proportion of the acid binder used may also be determined appropriately taking into account the stoichiometric ratio (equivalents) of the reaction. Specifically, it is preferable to use 2 equivalents or a slight excess of the acid binder per mole of the dihydric phenol compound (mc) used.

[0162] The solvent used in the synthesis method (P3-1a) may be a solvent used in the production of known polycarbonates, either singly or as a mixture of solvents. Examples of the solvent include hydrocarbon solvents (e.g., xylene) and halogenated hydrocarbon solvents (e.g., methylene chloride and chlorobenzene). In the synthesis method (P3-1a), the interfacial polycondensation reaction may be carried out using two mutually immiscible solvents.

[0163] In the synthesis method (P3-1a), a small amount of an antioxidant may be added, if desired. Examples of antioxidants include sodium sulfite and hydrosulfite. The reaction in the synthesis method (P3-1a) is usually carried out at a temperature in the range of 0 to 50°C, preferably 10 to 30°C. The reaction pressure can be reduced, normal pressure, or increased pressure, but is usually preferably carried out at normal pressure or the pressure of the reaction system. The reaction time depends on the reaction temperature and other factors, but is usually about 10 to 60 minutes, preferably about 15 to 30 minutes.

[0164] <Synthesis Method (P3-1b)> The synthesis method (P3-1b) is a method in which a transesterification reaction is carried out using a bisaryl carbonate as a carbonate ester-forming compound.

[0165] When a polycarbonate oligomer is synthesized by transesterification using a bisarylcarbonate as the carbonate ester-forming compound, suitable reaction methods include melt polycondensation and solid-phase polycondensation. Examples of bisarylcarbonate include di-p-tolylcarbonate, phenyl-p-tolylcarbonate, di-p-chlorophenylcarbonate, and dinaphthylcarbonate. When melt polycondensation is used in synthesis method (P3-1b), the dihydric phenol compound (mc) and the bisarylcarbonate are mixed and reacted in a molten state at a high temperature under reduced pressure. The reaction is typically carried out at a temperature in the range of 150 to 350°C, preferably 200 to 300°C. When solid-phase polycondensation is performed in synthesis method (P3-1b), the dihydric phenol compound (mc) and bisaryl carbonate are mixed and heated in the solid state to a temperature below the melting point of the resulting polycarbonate oligomer to carry out polycondensation. The reaction time depends on the reaction temperature and the degree of vacuum, but is usually about 30 minutes to 2 hours. The reaction is preferably carried out in an inert gas atmosphere such as nitrogen or argon, and the reaction may be carried out by adding the above-mentioned antioxidant, etc., as desired.

[0166] Next, the second step (P3-2) in the method for producing a PC-PAR resin according to this embodiment will be described. In the second step (P3-2), the ratio of the dicarboxylic acid compound (ma) or a derivative thereof used in preparing the reaction system may be appropriately selected in consideration of the stoichiometric ratio of the polycondensation reaction, and is not particularly limited. However, it is generally appropriate to use about 1 mole of the dicarboxylic acid compound (ma) or a derivative thereof per mole of the dicarboxylic acid compound (mc). The reaction system consisting of the dicarboxylic acid compound (ma) or a derivative thereof and the remaining dicarboxylic acid compound (mc) is typically prepared by mixing and stirring an aqueous solution of the dicarboxylic acid compound (mc) obtained by dissolving the remaining dicarboxylic acid compound (mc) in an aqueous solution of the alkali metal hydroxide or alkali metal carbonate, and a solution or suspension obtained by dissolving the dicarboxylic acid compound (ma) or a derivative thereof in the water-immiscible organic solvent. In this reaction system, a condensation reaction between the remainder of the dihydric phenol compound (mc) and the dicarboxylic acid compound (ma) or a derivative thereof proceeds, producing a polyester oligomer.

[0167] Next, in the second-stage reaction of step (P3-2), the polycarbonate oligomer synthesized in step (P3-1), preferably a solution of the polycarbonate oligomer in methylene chloride, is mixed with the system in which the polyester oligomer is produced, and a polycondensation reaction is carried out. The reaction temperature for this polycondensation reaction is typically in the range of about 0 to 50°C, preferably about 5 to 20°C. A reaction time of about 5 minutes to 3 hours, preferably about 10 minutes to 1.5 hours, is generally sufficient. The reaction pressure is not particularly limited, but is typically suitably carried out under normal pressure or slightly elevated pressure. When carrying out this polycondensation reaction, at least one additive component selected from the group consisting of a suitable molecular weight modifier, catalyst, solvent, etc., can be added to the reaction system as needed. In this manner, the PC-PAR resin according to this embodiment can be obtained.

[0168] As another example of the two-stage polymerization method for the PC-PAR resin according to this embodiment, a polycarbonate oligomer may be synthesized in the first stage in the same manner as in the step (P3-1) described above, and then the following step (P3-3) or step (P3-4) may be carried out in the second stage.

[0169] <Step (P3-3)> Step (P3-3) is a step of adding a solution of the dicarboxylic acid compound (ma) or a derivative thereof dissolved in the aqueous solution of the alkali metal hydroxide or the aqueous solution of the alkali metal carbonate to a solution of the polycarbonate oligomer synthesized in the step (P3-1) in a water-insoluble organic solvent, and carrying out a reaction in the presence of at least one of a terminal terminator and a catalyst.

[0170] <Step (P3-4)> Step (P3-4) is a step in which a reaction is carried out as follows. First, a solution (M1a) in which the remainder of the dihydric phenol compound (mc) is dissolved in an aqueous solution of an alkali metal hydroxide or an aqueous solution of an alkali metal carbonate is added to a solution (M1) in which the polycarbonate oligomer synthesized in step (P3-1) is dissolved in a water-insoluble organic solvent. To this solution ((M1) + (M1a)), a solution or suspension (M2) in which a dicarboxylic acid compound (ma) or a derivative thereof is dissolved or suspended in a water-immiscible, water-insoluble organic solvent (e.g., methylene chloride) is further added, and a polycondensation reaction is carried out in the presence of at least one of a terminal terminator and a catalyst.

[0171] Further, as yet another example of the two-stage polymerization method for the PC-PAR resin according to this embodiment, two-stage polymerization in which the following steps (P3-5) and (P3-6) are carried out can be mentioned.

[0172] <Step (P3-5)> The first step, step (P3-5), is a step of synthesizing a polyester oligomer from a part of the dihydric phenol compound (mc) and a dicarboxylic acid compound (ma) or a derivative thereof in the same manner as in step (P3-2).

[0173] <Step (P3-6)> The second step, step (P3-6), is a step in which a solution of the remainder of the dihydric phenol compound (mc) dissolved in the aqueous solution of the alkali metal hydroxide or the aqueous solution of the alkali metal carbonate is added to a solution of the polyester oligomer synthesized in step (P3-5) dissolved in an organic solvent, and the reaction is carried out in the presence of the carbonate ester-forming compound and at least one of a terminal terminator and a catalyst.

[0174] As a method for producing the PC-PAR resin according to this embodiment, a synthesis method may be selected depending on the structure and composition of the desired polyester polycarbonate.

[0175] In the method for producing a PC-PAR resin according to this embodiment, examples of the catalyst that can be used include tertiary amines such as triethylamine, and quaternary ammonium salts.

[0176] Examples of the branching agent that can be used in the method for producing a PC-PAR resin according to this embodiment include phloroglucin, pyrogallol, 1,1,1-tris(4-hydroxyphenyl)methane, 1,1,1-tris(4-hydroxyphenyl)ethane, 1,1,1-tris(4-hydroxyphenyl)propane, 1,1,1-tris(3-methyl-4-hydroxyphenyl)ethane, 4,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-2-heptene, 4,6-dimethyl-2,4, 6-tris(4-hydroxyphenyl)heptane, 2,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)-3-heptene, 1,3,5-tris(2-hydroxyphenyl)benzene, 1,3,5-tris(4-hydroxyphenyl)benzene, tris(4-hydroxyphenyl)-phenylmethane, 2,2-bis[4,4-bis(4-hydroxyphenyl)cyclohexyl]propane, 2,4-bis(4-hydroxyphenylisopropyl)phenol, 2,6-bis(2-hydroxy- 5-methylbenzyl)-4-methylphenol, 2-(4-hydroxyphenyl)-2-(2,4-dihydroxyphenyl)propane, α,α',α"-tris(4-hydroxyphenyl)-1,3,5-triisopropylbenzene, 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol, hexakis[4-(4-hydroxyphenylisopropyl)phenyl]-o-terephthalic acid ester, tetrakis(4-hydroxyphenyl)methane, tetrakis[4-(4-hydroxyphenylisopropyl)phenyl]-o-terephthalic acid ester [phenylisopropyl)phenoxy]methane, 1,4-bis[(4',4"-dihydroxytriphenyl)methyl]benzene, 2,4-dihydroxybenzoic acid, trimesic acid, cyanuric acid chloride, 3,3-bis(3-methyl-4-hydroxyphenyl)-2-oxo-2,3-dihydroindole, 3,3-bis(4-hydroxyaryl)oxindole [=isatin bisphenol], 5-chloroisatin, 5,7-dichloroisatin, 5-bromoisatin, and phloroglyside.

[0177] In order to adjust the molecular weight of the PC-PAR resin according to this embodiment, a terminal terminator (molecular weight regulator) can be used. Examples of the terminal terminator that can be used in the method for producing the PC-PAR resin according to this embodiment include monohydric phenols. More specific examples of the end terminator that can be used in the method for producing a PC-PAR resin according to this embodiment include phenol, α-naphthol, β-naphthol, o-cresol, m-cresol, p-cresol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, p-ethylphenol, p-propylphenol, p-butylphenol, p-pentylphenol, p-hexylphenol, p-heptylphenol, p-octylphenol, p-nonylphenol, p-decylphenol, p-undecylphenol, p-dodecylphenol, m-pentadecylphenol, p-isopropylphenol, p-tert-butylphenol, 2,6-dimethyl-p-tert-butylphenol, p-tert-octylphenol, 2-tert-amyl-4-methylphenol, 3-methyl-6-tert-butylphenol, Examples of such an amine include phenol, 2-methyl-4,6-di-tert-butylphenol, 2,4-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, 4-tert-octylphenol, 4-tert-amylphenol (p-tert-amylphenol), 2,4,6-tri-tert-butylphenol, p-phenylphenol, 2,6-di-tert-butyl-4-phenylphenol, 2,6-di-sec-butyl-4-methylphenol, o-anisole, m-anisole, p-anisole, o-chlorophenol, m-chlorophenol, p-chlorophenol, o-bromophenol, m-bromophenol, p-bromophenol, p-ethoxyphenol, o-aminophenol, m-aminophenol, p-aminophenol, p-cyanophenol, p-nitrophenol, 3-methyl-6-isopropylphenol, and 2-methyl-5-isopropylphenol.Preferred end terminators are p-tert-butylphenol and p-phenylphenol. In the method for producing a PC-PAR resin according to this embodiment, the end terminators may be used alone or in combination of two or more. In this embodiment, by using p-tert-butylphenol as the end terminator, a PC-PAR resin having an end group represented by the following general formula (T1) can be produced.

[0178]

[0179] (In the general formula (T1), * represents a bond to the repeating unit located at the terminal of the PC-PAR resin.)

[0180] The reduced viscosity of the PC-PAR resin according to this embodiment can be adjusted to a predetermined range by various methods, such as selecting the reaction conditions and adjusting the amounts of the end-capping agent and branching agent used. Furthermore, the obtained PC-PAR resin can be subjected to at least one of physical and chemical treatments, as appropriate, to obtain a PC-PAR resin with a predetermined reduced viscosity. Examples of physical treatments include mixing and fractionation. Examples of chemical treatments include polymer reaction, crosslinking, and partial decomposition.

[0181] According to the present embodiment, it is possible to provide a polycarbonate polyarylate resin that has excellent solubility in organic solvents and good abrasion resistance. According to one aspect of the polycarbonate polyarylate resin according to the present embodiment, the elastic power, elongation at break, and strength at break, which contribute to abrasion resistance, are improved.

[0182] Second Embodiment Resin Composition The resin composition according to this embodiment contains the polycarbonate polyarylate resin (PC-PAR resin) according to the first embodiment and additives as needed.

[0183] Examples of additives that may be contained in the resin composition according to this embodiment include functional compounds (e.g., charge transport materials, electron transport materials, hole transport materials, and charge generation materials), fillers (e.g., inorganic or organic fillers, fibers, cloths, and fine particles), colorants (e.g., dyes and pigments), low-molecular-weight compounds, reinforcing materials, elastomers for improving impact resistance, hydrolysis stabilizers, antioxidants, UV absorbers, flame retardants, flame retardant aids, and acid scavengers. The resin composition according to this embodiment may also contain a resin other than the PC-PAR resin according to the first embodiment. Examples of these additives and other resins that can be used include additives and resins known to be blendable with PC-PAR resins.

[0184] One embodiment of the resin composition according to this embodiment is a coating composition containing the PC-PAR resin according to the first embodiment and an organic solvent. The coating composition may be referred to as a varnish.

[0185] The organic solvent used in the coating liquid composition according to this embodiment can be appropriately selected taking into consideration the solubility of materials such as the PC-PAR resin according to the first embodiment, the drying speed after molding, the effect of the solvent remaining on the molded body, and hazards (fire or health hazards).

[0186] Examples of organic solvents used in the coating composition according to this 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 N,N-dimethylformamide (DMF) and dimethylacetamide (DMAc)), and aprotic polar solvents (such as dimethyl sulfoxide (DMSO)).

[0187] In the coating liquid composition of the present embodiment, in consideration of the environment and safety, the organic solvent is preferably an organic solvent other than halogenated hydrocarbons, i.e., a non-halogenated solvent, and more preferably at least one solvent selected from the group consisting of toluene, cyclohexanone, methyl ethyl ketone, tetrahydrofuran, dioxolane, and cyclopentanone.

[0188] The concentration of the PC-PAR resin according to the first embodiment in the coating composition according to this embodiment may be any concentration that provides an appropriate viscosity for the intended use of the coating composition, and is preferably 0.1% by mass or more and 40% by mass or less. The concentration of the PC-PAR resin according to the first embodiment in the coating composition according to this embodiment is more preferably 1% by mass or more, and even more preferably 5% by mass or more. The concentration of the PC-PAR resin according to the first embodiment in the coating composition according to this embodiment is more preferably 35% by mass or less, and even more preferably 30% by mass or less. When the concentration of the PC-PAR resin according to the first embodiment in the coating composition according to this embodiment is 40% by mass or less, the viscosity does not become too high and the coatability is good. When the concentration of the PC-PAR resin according to the first embodiment in the coating composition according to this embodiment is 0.1% by mass or more, the viscosity can be maintained at an appropriate level, and a homogeneous film can be obtained. Furthermore, when the concentration is 0.1% by mass or more, the drying time after application of the coating composition can be shortened and a film of the desired thickness can be easily formed.

[0189] The coating composition according to this embodiment may contain the above-mentioned additives in addition to the PC-PAR resin according to the first embodiment and the organic solvent. The coating composition according to this embodiment may contain one type of PC-PAR resin according to the first embodiment alone, or two or more types of PC-PAR resins according to the first embodiment.

[0190] The resin composition according to this embodiment may further contain a charge transport material. Furthermore, the coating composition according to this embodiment may further contain a charge transport material. When the coating composition according to this embodiment contains a charge transport material, from the viewpoint of product performance, the ratio of the resin composition to the charge transport material in the coating composition according to this embodiment is preferably in the range of 20:80 to 80:20 by mass, more preferably in the range of 30:70 to 70:30.

[0191] Examples of fillers that may be contained in the resin composition according to this embodiment include inorganic fillers. In this embodiment, the inorganic filler is preferably at least one filler selected from the group consisting of silica, boron nitride, aluminum nitride, silicon nitride, silicon carbide, zinc oxide, titanium oxide, aluminum oxide, magnesium oxide, aluminum hydroxide, and magnesium hydroxide. The silica as the inorganic filler is preferably at least one silica selected from the group consisting of spherical silica, pulverized silica, hollow silica, and fumed silica.

[0192] The coating composition according to this embodiment is usually suitable for use in forming a photosensitive layer of a laminated electrophotographic photoreceptor. The photosensitive layer of a laminated electrophotographic photoreceptor preferably includes at least a charge generation layer and a charge transport layer, and the coating composition according to this embodiment is suitable for use in forming a charge transport layer. Furthermore, by further incorporating the charge generation material into the coating composition according to this embodiment, it is also possible to use the coating composition according to this embodiment in forming a photosensitive layer of a single-layer electrophotographic photoreceptor. Furthermore, the coating composition according to this embodiment can also be used in forming a protective layer of the photoreceptor.

[0193] Since the resin composition according to this embodiment contains the polycarbonate polyarylate resin according to the first embodiment, a molded article or the like molded using the resin composition has excellent abrasion resistance. Moreover, since the polycarbonate polyarylate resin according to the first embodiment has excellent solubility in organic solvents, this embodiment can also provide a coating liquid composition that is unlikely to become cloudy even when the concentration of the polycarbonate polyarylate resin is increased.

[0194] [Third Embodiment] [Molded Article] The molded article according to this embodiment contains the polycarbonate polyarylate resin (PC-PAR resin) according to the first embodiment. The molded article according to this embodiment can be used for various applications in addition to the application of the electrophotographic photoreceptor described below. For example, the molded article according to this embodiment can be suitably used for applications such as substrates, insulating layers, protective layers, adhesive layers, conductive layers, and structural materials for electronic devices. Furthermore, the molded article according to this embodiment can also be applied to films, coating films, sheets, insulating materials, and the like. The molded articles exemplified here may contain at least the PC-PAR resin according to the first embodiment.

[0195] The film according to this embodiment contains the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment. The film according to this embodiment can be produced by thermoforming (e.g., melt extrusion molding) the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment into a film, or by wet molding (e.g., a method of forming a film by solution casting). When a thin film (e.g., a film thickness of several μm to several tens of μm) is desired for the film according to this embodiment, solution casting is preferred. Furthermore, for the purpose of reducing thermal expansion, the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment may be impregnated into glass cloth, or the resin composition according to the second embodiment may be formed into a film in which an inorganic filler such as silica is dispersed.

[0196] The sheet according to this embodiment contains the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment. When the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment is used as a sheet, the sheet can be formed by impregnating a substrate or the like with the above-mentioned coating liquid composition (varnish).

[0197] Herein, a film containing the PC-PAR resin according to the first embodiment and a coating film containing the PC-PAR resin according to the first embodiment are clearly distinguished from each other. The film containing the PC-PAR resin according to the first embodiment refers to a resin body formed from the PC-PAR resin according to the first embodiment, which has a thickness smaller than its length and width. For example, when the film according to the present embodiment is a resin body formed by applying the coating composition according to the second embodiment to an object and peeling it off from the object, this resin body is a film. The coating film containing the PC-PAR resin according to the first embodiment refers to a layer formed by coating the coating composition according to the second embodiment on an object. Generally, the coating film remains on the object as is and constitutes part of the finished product.

[0198] The molded article according to this embodiment can be produced using the resin composition according to the second embodiment. When a molded article is produced using the resin composition according to the second embodiment, either a wet molding method or a melt molding method can be used as the molding method.

[0199] The molded article according to this embodiment has excellent abrasion resistance because it contains the polycarbonate polyarylate resin according to the first embodiment.

[0200] [Fourth embodiment] [Electrophotographic photoreceptor] The electrophotographic photoreceptor according to this embodiment has a layer containing the polycarbonate polyarylate resin (PC-PAR resin) according to the first embodiment or the resin composition according to the second embodiment. The electrophotographic photoreceptor according to this embodiment preferably contains the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment in the outermost layer of the electrophotographic photoreceptor. By using the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment in the outermost layer of the electrophotographic photoreceptor according to this embodiment, an electrophotographic photoreceptor with excellent abrasion resistance can be obtained.

[0201] The electrophotographic photoreceptor according to this embodiment includes a substrate (preferably a conductive substrate) and a photosensitive layer provided on the substrate. In the electrophotographic photoreceptor according to this embodiment, the photosensitive layer preferably contains the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment.

[0202] The electrophotographic photoreceptor according to this embodiment may be any of various known types of electrophotographic photoreceptors or other types of electrophotographic photoreceptors, as long as it has a layer containing the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment. The electrophotographic photoreceptor according to this embodiment is preferably a multi-layer electrophotographic photoreceptor or a single-layer electrophotographic photoreceptor. The photosensitive layer in the multi-layer electrophotographic photoreceptor has at least one charge generation layer and at least one charge transport layer. The photosensitive layer in the single-layer electrophotographic photoreceptor contains a charge generation material and a charge transport material in one layer. A photosensitive layer containing a charge generation material and a charge transport material in one layer may be referred to as a charge generation / transport layer.

[0203] Examples of the layer structure of the electrophotographic photoreceptor according to this embodiment include the following structures: Substrate / charge generation layer / charge transport layer Substrate / charge transport layer / charge generation layer Substrate / charge generation and transport layer Substrate / charge generation layer / charge transport layer / surface protective layer Substrate / charge transport layer / charge generation layer / surface protective layer Substrate / charge generation and transport layer / surface protective layer

[0204] In the electrophotographic photoreceptor according to this exemplary embodiment, the photosensitive layer preferably has a charge transport layer and a charge generation layer included between the charge transport layer and the conductive substrate.

[0205] The PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment may be used in any part of the photosensitive layer.

[0206] In the electrophotographic photoreceptor according to this embodiment, it is preferable to use the PC-PAR resin according to the first embodiment as a binder resin in at least one of the charge generation layer, the charge transport layer, and the surface protective layer.

[0207] In the electrophotographic photoreceptor according to this embodiment, the charge transport layer preferably contains the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment. For example, in order to fully exhibit the effects of this embodiment, the charge transport layer preferably contains the PC-PAR resin according to the first embodiment as a binder resin for the charge transport material in the charge transport layer, or as a binder resin in a single photosensitive layer. When the electrophotographic photoreceptor according to this embodiment is a multilayer electrophotographic photoreceptor having two or more charge transport layers, it is preferable that any one of the charge transport layers contains the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment.

[0208] The electrophotographic photoreceptor according to this embodiment may contain one type of PC-PAR resin according to the first embodiment alone, or may contain a combination of two or more types of PC-PAR resins according to the first embodiment. Furthermore, the electrophotographic photoreceptor according to this embodiment may contain other binder resin components such as polycarbonates, as desired, and may further contain additives such as antioxidants, within a range that does not impair the object of this embodiment.

[0209] 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. Alternatively, the photosensitive layer may contain both a charge generation material and a charge transport material in one layer. Furthermore, if necessary, a conductive or insulating protective film may be formed on the surface protective layer. In the electrophotographic photoreceptor of this embodiment, it is also preferable that the surface protective layer contains the PC-PAR resin of the first embodiment or the resin composition of the second embodiment. The electrophotographic photoreceptor of this embodiment may have an adhesive layer to improve adhesion between each layer. The electrophotographic photoreceptor of this embodiment may have an intermediate layer, such as a blocking layer that serves to block charges, between each layer.

[0210] The conductive substrate, charge generation layer, charge transport layer, undercoat layer, blocking layer, and surface protection layer of the electrophotographic photoreceptor according to this embodiment may be formed using known structures, materials, compositions, and the like. For example, the description of JP-A-2022-159231 is incorporated herein by reference.

[0211] <Conductive Substrate> As the conductive substrate material used in the electrophotographic photoreceptor of the present embodiment, various materials such as known materials can be used. Specifically, the following can be used: a plate, drum, and sheet made of 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; a film, sheet, or seamless belt made of glass, cloth, paper, or plastic that has been treated to be conductive by coating by vapor deposition, sputtering, painting, or the like; and a metal drum that has been treated to be metal-oxidized by electrode oxidation or the like.

[0212] <Charge Generation Layer> In the electrophotographic photoreceptor according to this embodiment, the charge generation layer contains at least a charge generation material. This charge generation layer can be obtained by forming a layer of the charge generation material on the underlying substrate by vacuum deposition or sputtering, or by forming a layer of the charge generation material on the underlying substrate by binding it with a binder resin. Various methods, including known methods, can be used to form a charge generation layer using a binder resin. Typically, a suitable method involves, for example, applying a coating composition in which the charge generation material is dispersed or dissolved together with the binder resin in an appropriate solvent onto a predetermined underlying substrate, and drying the coating to obtain a wet-formed body.

[0213] (Charge Generation Material) In the electrophotographic photoreceptor according to the present embodiment, various known materials can be used as the charge generation material in the charge generation layer. Specific compounds as the charge generation material include selenium alone (e.g., amorphous selenium and trigonal selenium), selenium alloys (e.g., selenium-tellurium), selenium compounds or selenium-containing compositions (e.g., As ２Se ３ and the like), inorganic materials consisting of elements of Groups 12 and 16 of the periodic table (for example, zinc oxide and CdS—Se), oxide-based semiconductors (for example, titanium oxide), silicon-based materials (for example, amorphous silicon), metal-free phthalocyanine pigments (for example, τ-type metal-free phthalocyanine and χ-type metal-free phthalocyanine), metal phthalocyanine pigments (for example, 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, Examples of suitable pigments include phthalocyanine, Y-type titanyl phthalocyanine, Y-type oxo-titanyl phthalocyanine, α-type oxo-titanyl phthalocyanine, β-type oxo-titanyl phthalocyanine, titanyl phthalocyanine that exhibits a strong diffraction peak at a Bragg angle 2θ of 27.3±0.2 degrees in an X-ray diffraction diagram, and gallium phthalocyanine), cyanine dyes, anthracene pigments, bisazo pigments, pyrene pigments, polycyclic quinone pigments, quinacridone pigments, indigo pigments, perylene pigments, pyrylium dyes, squalium pigments, anthanthrone 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. These compounds can be used alone or in combination as a charge generating material. Among these charge generating materials, the charge generating materials specifically described in JP-A-11-172003 are preferred.

[0214] <Charge Transport Layer> In the electrophotographic photoreceptor according to this embodiment, the charge transport layer can be obtained as a wet-molded body by forming a layer of a charge transport material bound with a binder resin on a substrate serving as a base.

[0215] (Charge Transporting Material) As the charge transporting material that can be used together with the PC-PAR resin according to the first embodiment, various known compounds can be used. Suitable examples of such compounds include 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, and polymers having these structures in the main chain or side chain. 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 No. 11-172003 and the charge transport materials represented by the following structures are particularly suitable.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] (Binder Resin) The binder resin for the charge generating layer or charge transport layer is not particularly limited, and various known resins can be used. Specific examples include 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, and polyether resin. , benzoguanamine resin, epoxy acrylate resin, urethane acrylate resin, poly-N-vinyl carbazole, polyvinyl butyral, polyvinyl formal, polysulfone, casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, carboxymethyl cellulose, vinylidene chloride polymer latex, acrylonitrile-butadiene copolymer, vinyltoluene-styrene copolymer, soybean oil-modified alkyd resin, nitrated polystyrene, polymethylstyrene, polyisoprene, polythiocarbonate, polyarylate, polyhaloarylate, polyallyl ether, polyvinyl acrylate, and polyester acrylate. These binder resins can be used alone or in combination of two or more. It is preferable to use the PC-PAR resin according to the first embodiment as the binder resin in at least one of the charge generation layer and the charge transport layer.

[0231] Although various known methods can be used to form the charge transport layer, a preferred method involves applying a coating composition (preferably a coating composition according to the second embodiment) prepared by dispersing or dissolving a charge transport material together with the PC-PAR resin according to the first embodiment in an appropriate solvent onto a substrate, and drying the resulting coating to obtain a wet-molded body. The blending ratio of the charge transport material to the PC-PAR resin according to the first embodiment used to form the charge transport layer is preferably in the range of 20:80 to 80:20 by mass, more preferably in the range of 30:70 to 70:30. In this charge transport layer, the PC-PAR resin according to the first embodiment can be used alone or in combination with two or more different resins. Furthermore, other binder resins can also be used in combination with the PC-PAR resin according to the first embodiment, as long as the object of the present invention is not impaired.

[0232] The thickness of the charge transport layer thus formed is usually about 5 μm to 100 μm, preferably 10 μm to 50 μm, and more preferably 15 μm to 40 μm. If the thickness of this charge transport layer is 5 μm or more, the initial potential does not decrease, and if the thickness of the charge transport layer is 100 μm or less, deterioration of electrophotographic properties can be prevented.

[0233] An electron-accepting substance can be added to the photosensitive layer to the extent that the effects of the present invention are not lost, for the purposes of improving sensitivity, reducing residual potential, reducing fatigue during repeated use, etc. Specific examples of such an electron-accepting substance include succinic anhydride, maleic anhydride, dibromomaleic 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 chlorimide, chloranil, bromanil, benzoquinone, 2,3-dichlorobenzoquinone, dichlorodicyanoparabenzoquinone, naphthoquinone, diphenoquinone, tropoquinone, anthraquinone, 1-chloroanthraquinone, dinitroanthraquinone, 4-nitrobenzophenone, 4,4'-dinitro Compounds having a large electron affinity, such as benzophenone, 4-nitrobenzalmalondinitrile, α-cyano-β-(p-cyanophenyl)ethyl acrylate, 9-anthracenylmethylmalondinitrile, 1-cyano-(p-nitrophenyl)-2-(p-chlorophenyl)ethylene, 2,7-dinitrofluorenone, 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, 9-fluorenylidene-(dicyanomethylenemalononitrile), polynitro-9-fluorenylidene-(dicyanomethylenemalonodinitrile), 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, are preferred. These compounds as electron accepting substances may be added to either the charge generating layer or the charge transporting layer, and the blending ratio of the electron accepting substance 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, per 100 parts by mass of the charge generating substance or the charge transporting substance, within a range that does not impair the effects of the present invention.

[0234] In addition, to improve the surface properties, a surface modifier can be added to the photosensitive layer within a range that does not impair the effects of the present invention. Specific examples of surface modifiers include tetrafluoroethylene resin, trifluorochloroethylene resin, tetrafluoroethylene hexafluoropropylene resin, vinyl fluoride resin, vinylidene fluoride resin, difluorodichloroethylene resin, and copolymers thereof, as well as fluorine-based graft polymers. The blending ratio of these surface modifiers relative to the binder resin 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, within a range that does not impair the effects of the present invention. If the blending ratio of the surface modifier is 0.1% by mass or more, surface modification such as surface durability and surface energy reduction is sufficient, and if it is 60% by mass or less, there is no deterioration in electrophotographic properties.

[0235] Specific examples of the solvent used in forming at least one of the charge generating layer and the charge transport layer include aromatic solvents (e.g., benzene, toluene, xylene, and chlorobenzene), ketones (e.g., acetone, methyl ethyl ketone, and cyclohexanone), alcohols (e.g., methanol, ethanol, and isopropanol), esters (e.g., ethyl acetate and ethyl cellosolve), halogenated hydrocarbons (e.g., carbon tetrachloride, carbon tetrabromide, chloroform, dichloromethane, and tetrachloroethane), ethers (e.g., tetrahydrofuran, dioxolane, and dioxane), sulfoxides (e.g., dimethyl sulfoxide), and amides (e.g., dimethylformamide and diethylformamide). These solvents may be used alone or in combination of two or more.

[0236] The photosensitive layer of the single-layer electrophotographic photoreceptor can be easily formed by using the charge generating material, charge transport material, and additives described above, and applying the PC-PAR resin according to the first embodiment as a binder resin. Furthermore, it is preferable to add at least one of a hole transport material and an electron transport material as the charge transport material. The electron transport material exemplified in JP-A-2005-139339 can be preferably used.

[0237] Each layer of the electrophotographic photoreceptor can also be formed by a coating method using various coating devices such as known devices, specifically, for example, an applicator, a spray coater, a bar coater, a tip coater, a roll coater, a dip coater, and a doctor blade.

[0238] The thickness of the photosensitive layer in the electrophotographic photoreceptor is, for example, 5 μm to 100 μm, preferably 8 μm to 50 μm. When the thickness of the photosensitive layer is 5 μm or more, it is possible to prevent the initial potential from decreasing, and when the thickness of the photosensitive layer is 100 μm or less, it is possible to suppress the deterioration of electrophotographic characteristics.

[0239] The ratio of the charge generating material used in the production of the electrophotographic photoreceptor to the PC-PAR resin according to the first embodiment is preferably in the range of 20:80 to 80:20 by mass, and more preferably in the range of 30:70 to 70:30.

[0240] The electrophotographic photoreceptor obtained in this manner has the PC-PAR resin according to the first embodiment as a binder resin in the photosensitive layer, and therefore has excellent properties such as durability, as well as excellent electrical properties (electrophotographic properties), and is a photoreceptor that maintains excellent electrophotographic properties over a long period of time. The electrophotographic photoreceptor is suitable for use in various electrophotographic fields, such as copiers (monochrome, multicolor, full-color, analog, digital), printers (laser, LED, liquid crystal shutter), facsimiles, platemaking machines, and devices having multiple functions thereof. The electrophotographic photoreceptor of this embodiment can be suitable for use in electrophotographic devices.

[0241] [Method for manufacturing electrophotographic photoreceptor] Examples of the method for manufacturing an electrophotographic photoreceptor according to this embodiment include a method (cast film-forming method) comprising the steps of applying the coating composition according to the second embodiment to a conductive substrate by a wet molding method and removing the organic solvent in the coating composition by heating. In the cast film-forming method, the functional material and the binder resin are required to have solubility and stability in organic solvents. The PC-PAR resin according to the first embodiment has excellent solubility in organic solvents, and is therefore preferably used as the binder resin.

[0242] The electrophotographic photoreceptor according to this embodiment has a layer containing the PC-PAR resin according to the first embodiment or the resin composition according to the second embodiment, and thus has excellent abrasion resistance and suppresses a decrease in residual potential.

[0243] Next, the present invention will be described in more detail with reference to examples and comparative examples. However, the present invention is not limited to these examples, and various modifications and applications are possible within the scope of the present invention.

[0244] [Production Examples: Preparation of Oligomers] <Production Example 1: Synthesis of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane oligomer (bischloroformate)> 66.4 g (224 mmol) of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane was suspended in 1,080 mL of methylene chloride, and 66.0 g (667 mmol) of phosgene was added thereto. A solution of 44.0 g (435 mmol) of triethylamine dissolved in 120 mL of methylene chloride was added dropwise thereto at a temperature in the range of 5°C to 15°C. After stirring for 30 minutes, the methylene chloride was distilled off until the predetermined concentration was reached. The remaining liquid was washed with 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite. The oligomer was then washed five times with 210 mL of pure water to obtain a methylene chloride solution of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane oligomer having chloroformate groups at the molecular terminals. The resulting solution had a chloroformate concentration of 1.07 mol / L, a solids concentration of 0.232 kg / L, and an average number of monomers of 1.04. Hereinafter, the resulting oligomer according to Production Example 1 will be referred to as CZ-CF. Hereinafter, 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane may be abbreviated as CZ.

[0245] <Production Example 2: Synthesis of 1,1-bis-(4-hydroxyphenyl)cyclohexane oligomer (bischloroformate)> The oligomer according to Production Example 2 was produced in the same manner as in Production Example 1, except that 60.1 g (224 mmol) of 1,1-bis-(4-hydroxyphenyl)cyclohexane was used instead of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane. The chloroformate concentration of the resulting solution was 1.10 mol / L, the solid concentration was 0.222 kg / L, and the average number of monomers was 1.04. Hereinafter, the obtained oligomer according to Production Example 2 will be referred to as Z-CF. Hereinafter, 1,1-bis-(4-hydroxyphenyl)cyclohexane will sometimes be abbreviated as Z.

[0246] [Production Example: Production of PC-PAR Resin, etc.] Next, the production of a polycarbonate polyarylate polymer (PC-PAR polymer) as a polycarbonate polyarylate resin (PC-PAR resin), a polyarylate polymer (PAR polymer) as a polyarylate resin (PAR resin), and a polycarbonate polymer (PC polymer) as a polycarbonate resin (PC resin) will be described.

[0247] Example 1 (Production of PC-PAR Polymer) 21.6 mL of CZ-CF from Production Example 1, 164 mL of methylene chloride, and 0.143 g of p-tert-butylphenol were added to a reaction vessel equipped with a mechanical stirrer, stirring blades, and baffles, and the mixture was stirred to ensure thorough mixing. The mixture was then cooled to 10°C to obtain a methylene chloride solution (M1). Hereinafter, p-tert-butylphenol may be abbreviated as PTBP. Furthermore, 11.7 g of 2,6-naphthalenedicarboxylic acid dichloride and 93 mL of methylene chloride were added to a separate vessel, and the mixture was stirred and suspended at room temperature to obtain a methylene chloride suspension (M2). Hereinafter, 2,6-naphthalenedicarboxylic acid dichloride may be abbreviated as 26NP. To the methylene chloride solution (M1) in the reaction vessel, the entire amount of an aqueous sodium hydroxide solution (an aqueous solution prepared by cooling 648 mL of 2.0 N aqueous potassium hydroxide solution (13.5 g of potassium hydroxide) to below room temperature, adding 17.1 g of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane, 0.15 g of sodium hydrosulfite, and 0.12 g of benzyltripropylammonium chloride and completely dissolving the solution) was added, and an aqueous triethylamine solution (7% by volume, 1.2 mL) was added with stirring. Next, the methylene chloride suspension (M2) was added dropwise over 30 minutes while maintaining the temperature in the reaction vessel at 10°C, and stirring was continued for 1 hour. The resulting reaction mixture was diluted with 0.57 L of methylene chloride and washed. The lower layer was separated and further washed once with 0.15 L of water, once with 0.15 L of 0.03 N hydrochloric acid, and three times with 0.15 L of water, in that order. The resulting methylene chloride solution was added dropwise to methanol under stirring, and the resulting reprecipitate was filtered and dried to obtain a PC-PAR polymer (PC-PAR-1) having the following structure.

[0248] (Identification of PC-PAR Polymer) The PC-PAR polymer (PC-PAR-1) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL. The reduced viscosity [ηsp / C] at 20°C was measured and found to be 1.30 dL / g. The structure and composition of the obtained PC-PAR polymer (PC-PAR-1) were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC-PAR polymer having the following repeating units and composition:

[0249]

[0250] In the PC-PAR polymer (PC-PAR-1), the repeating unit [CZ] derived from the raw material monomer CZ contained a structural unit represented by the general formula (C1) above, and the repeating unit [26NP] derived from the raw material monomer 26NP contained a structural unit represented by the general formula (A1) or (A11) above, and the molar fraction c was 55 mol %, the molar fraction b was 9 mol %, and the molar fraction ax was 36 mol %. The composition ratio (mol %) of the repeating units in the PC-PAR polymer (PC-PAR-1) was [CZ]:[26NP]=60:40.

[0251] Example 2 Production of PC-PAR Polymer A PC-PAR polymer (PC-PAR-2) having the following structure was obtained in the same manner as in Example 1, except that 5.9 g of 2,6-naphthalenedicarboxylic acid dichloride and 5.9 g of 1,4-naphthalenedicarboxylic acid dichloride were used instead of 11.7 g of 2,6-naphthalenedicarboxylic acid dichloride. Hereinafter, 1,4-naphthalenedicarboxylic acid dichloride may be abbreviated as 14NP.

[0252] (Identification of PC-PAR Polymer) The PC polymer (PC-PAR-2) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL. The reduced viscosity [ηsp / C] at 20°C was measured and found to be 1.25 dL / g. The structure and composition of the PC polymer (PC-PAR-2) obtained were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC-PAR polymer having the following repeating units and composition:

[0253]

[0254] In the PC-PAR polymer (PC-PAR-2), the repeating unit [CZ] derived from the raw material monomer CZ contained a structural unit represented by the general formula (C1), the repeating unit [26NP] derived from the raw material monomer 26NP contained a structural unit represented by the general formula (A1) or (A11), and the repeating unit [14NP] derived from the raw material monomer 14NP contained a structural unit represented by the general formula (A1) or (A12), and the molar fraction c was 55 mol%, the molar fraction b was 9 mol%, and the molar fraction ax was 36 mol%. In the PC-PAR polymer (PC-PAR-2), the molar fraction ax corresponded to the sum of the molar fraction as in the structural unit represented by the general formula (A11) and the molar fraction at in the structural unit represented by the general formula (A12) (ax = as + at), and the molar fraction as was 18 mol%, and the molar fraction at was 18 mol%. The composition ratio (mol %) of the repeating units in the PC-PAR polymer (PC-PAR-2) was [CZ]:[26NP]:[14NP]=60:20:20.

[0255] Example 3 Production of PC-PAR Polymer A PC-PAR polymer (PC-PAR-3) having the following structure was obtained in the same manner as in Example 1, except that 41.9 mL of Z-CF obtained in Production Example 2 and 180 mL of methylene chloride were used instead of 164 mL of methylene chloride in preparing the methylene chloride solution (M1), and that 5.83 g of 26NP and 122 mL of methylene chloride were used to prepare the methylene chloride suspension (M2).

[0256] (Identification of PC-PAR Polymer) The PC-PAR polymer (PC-PAR-3) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL. The reduced viscosity [ηsp / C] at 20°C was measured and found to be 1.32 dL / g. The structure and composition of the obtained PC-PAR polymer (PC-PAR-3) were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC-PAR polymer having the following repeating units and composition:

[0257]

[0258] In the PC-PAR polymer (PC-PAR-3), the repeating unit [CZ] derived from the raw material monomer CZ contained a structural unit represented by the general formula (C1), the repeating unit [26NP] derived from the raw material monomer 26NP contained a structural unit represented by the general formula (A1) or (A11), and the repeating unit [Z] derived from the raw material monomer Z contained a structural unit represented by the general formula (C1), and the molar fraction c(CZ) of the structural unit represented by the general formula (C1) corresponding to the repeating unit [CZ] was 47 mol%, and the molar fraction c(Z) of the structural unit represented by the general formula (C1) corresponding to the repeating unit [Z] was 15 mol%. The composition ratio (mol %) of the repeating units in the PC-PAR polymer (PC-PAR-3) was [CZ]:[Z]:[26NP]=60:20:20.

[0259] Comparative Example 1 (Production of Polyarylate Polymer (PAR Polymer)) First, 711 mL of 2.0 N aqueous sodium hydroxide solution (14.9 g of sodium hydroxide) was cooled to room temperature or below, and then 618.3 g of 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane, 0.040 g of PTBP, 0.15 g of sodium hydrosulfite, and 0.10 g of benzyltripropylammonium chloride were added and completely dissolved to prepare an aqueous sodium hydroxide solution (M3). Also, 15.2 g of 26NP was suspended in 104 mL of methylene chloride and cooled to 10°C to prepare a methylene chloride suspension (M4). The aqueous sodium hydroxide solution (M3) was added to a reaction vessel equipped with a mechanical stirrer, stirring blades, and baffles, and the mixture was cooled to 10°C. To the aqueous sodium hydroxide solution (M3) in this reaction vessel, the methylene chloride suspension (M4) cooled to 10°C was added dropwise over 30 minutes, and stirring was then continued for 1 hour. The resulting reaction mixture was diluted with 0.54 L of methylene chloride and washed. The lower layer was separated and further washed once with 0.15 L of water, once with 0.15 L of 0.03 N hydrochloric acid, and three times with 0.15 L of water, in that order. The resulting methylene chloride solution was added dropwise to methanol with stirring, and the resulting reprecipitate was filtered and dried to obtain a PAR polymer (PAR-1) having the following structure.

[0260] (Identification of PAR polymer) The PAR polymer (PAR-1) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 1.24 dL / g. The structure and composition of the obtained PAR polymer (PAR-1) were １ Analysis by H-NMR spectrum confirmed that the polymer was a PAR polymer having the following repeating units and composition: This PAR polymer (PAR-1) did not contain any polycarbonate-based repeating units.

[0261]

[0262] In the PAR polymer (PAR-1), the repeating unit [CZ] derived from the raw material monomer CZ contained a structural unit represented by the general formula (C1) above, and the repeating unit [26NP] derived from the raw material monomer 26NP contained a structural unit represented by the general formula (A1) or (A11) above, and the molar fraction c was 50 mol %, the molar fraction b was 0 mol %, and the molar fraction ax was 50 mol %. The composition ratio (mol %) of the repeating units in the PC-PAR polymer (PAR-1) was [CZ]:[26NP]=50:50.

[0263] Comparative Example 2 (Production of PAR Polymer) A PAR polymer (PAR-2) having the following structure was obtained in the same manner as in Comparative Example 1, except that 7.6 g of 26NP and 7.6 g of 14NP were used instead of 15.2 g of 26NP in the methylene chloride suspension (M4) of Comparative Example 1.

[0264] (Identification of PAR polymer) The PAR polymer (PAR-2) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 1.10 dL / g. The structure and composition of the obtained PAR polymer (PAR-2) were １ Analysis by H-NMR spectrum confirmed that this PAR polymer had the following repeating units and composition: This PAR polymer (PAR-2) did not have any polycarbonate-based repeating units.

[0265]

[0266] In the PAR polymer (PAR-2), the repeating unit [CZ] derived from CZ as a raw material monomer contained a structural unit represented by the general formula (C1), the repeating unit [26NP] derived from 26NP as a raw material monomer contained a structural unit represented by the general formula (A1), and the repeating unit [14NP] derived from 14NP as a raw material monomer contained a structural unit represented by the general formula (A2), and the molar fraction c was 50 mol%, the molar fraction b was 0 mol%, and the molar fraction ax was 50 mol%. In the PAR polymer (PAR-2), the molar fraction ax corresponded to the sum of the molar fraction as in the structural unit represented by the general formula (A11) and the molar fraction at in the structural unit represented by the general formula (A12) (ax = as + at), and the molar fraction as was 25 mol%, and the molar fraction at was 25 mol%. The composition ratio (mol %) of the repeating units in the PAR polymer (PAR-2) was [CZ]:[26NP]:[14NP]=50:25:25.

[0267] Comparative Example 3 (Production of PC Polymer) 216 mL of CZ-CF from Production Example 1, 340 mL of methylene chloride, and 0.362 g of PTBP were added to a reaction vessel equipped with a mechanical stirrer, stirring blades, and baffles, and the mixture was stirred to ensure thorough mixing. The mixture was then cooled to 10°C to obtain a methylene chloride solution (M5). Furthermore, 185 mL of 2.0 N aqueous sodium hydroxide solution (17.1 g of sodium hydroxide) was cooled to below room temperature, and then 18.5 g of 2,6-dihydroxynaphthalene and 0.23 g of sodium hydrosulfite were added and completely dissolved to obtain an aqueous sodium hydroxide solution (M6). Hereinafter, 2,6-dihydroxynaphthalene may be abbreviated as 26DON. The entire amount of the aqueous sodium hydroxide solution (M6) was added to the methylene chloride solution (M5) in the reaction vessel. A triethylamine aqueous solution (7% by volume, 2.3 mL) was added with stirring, and stirring was continued for 1 hour. The resulting reaction mixture was diluted with 1.14 L of methylene chloride and 0.11 L of water and washed. The lower layer was separated and further washed once with 0.30 L of water, once with 0.30 L of 0.03 N hydrochloric acid, and three times with 0.30 L of water, in that order. The resulting methylene chloride solution was added dropwise to methanol with stirring, and the resulting reprecipitate was filtered and dried to obtain a PC polymer (PC-1) having the following structure.

[0268] (Identification of PC polymer) The PC polymer (PC-1) thus obtained was dissolved in methylene chloride to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] at 20°C was measured to be 1.00 dL / g. The structure and composition of the obtained PC polymer (PC-1) were as follows: １ Analysis by H-NMR spectrum confirmed that the polymer was a PC polymer having the following repeating units and composition: This PC polymer (PC-1) did not contain any polyarylate-based repeating units.

[0269]

[0270] In the PC polymer (PC-1), the repeating unit [CZ] derived from CZ as a raw material monomer contained a structural unit represented by the general formula (C1), and the repeating unit [26DON] derived from 26DON as a raw material monomer contained a structural unit represented by the general formula (C1), with a molar fraction c of 50 mol%, a molar fraction b of 50 mol%, a molar fraction ax of 0 mol%, and a molar fraction ay of 0 mol%. The molar fraction c(CZ) of the structural unit represented by general formula (C1) corresponding to the repeating unit [CZ] was 30 mol%, and the molar fraction c(26DON) of the structural unit represented by general formula (C1) corresponding to the repeating unit [26DON] was 20 mol%. The composition ratio (mol%) of the repeating units in the PC polymer (PC-1) was [CZ]:[26DON]=60:40.

[0271] <Evaluation of Polymers> The polymers (PC-PAR polymer, PAR polymer, and PC polymer) produced in the above Examples and Comparative Examples were evaluated as follows. The evaluation results are shown in Table 1.

[0272] (Reduced Viscosity: [ηsp / C]) Each polymer was dissolved in methylene chloride as a solvent to prepare a solution with a concentration of 0.5 g / dL, and the reduced viscosity [ηsp / C] of this solution was measured using an Ubbelohde viscometer at a temperature of 20° C.±0.01° C. The flow time of the solvent alone was 72.4 seconds.

[0273] (Polymer solubility) The solubility of each polymer was confirmed by adding 1 g of the polymer to tetrahydrofuran so that the polymer concentration was adjusted to 5 to 13% by mass, stirring with a shaker for 30 minutes, and visually observing any undissolved parts in the liquid, and evaluating the solubility based on the following solubility evaluation criteria. -Solubility evaluation criteria A: Completely dissolved at a polymer concentration of 13% by mass B: Completely dissolved at a polymer concentration of 5% by mass and becoming cloudy at a polymer concentration of 13% by mass C: Cloudy at a polymer concentration of 5% by mass

[0274] (Tensile Properties of Polymers) The tensile properties of the polymers produced in the above Examples and Comparative Examples, namely, the breaking strength (unit: MPa) and breaking elongation (unit: %), were measured as follows. First, each polymer (2 g) was added to methylene chloride (10 g) and stirred for 30 minutes with a shaker to obtain a coating composition. The obtained coating composition was cast onto a glass plate using an applicator with a gap of 500 μm to form a film. After air-drying for 1 hour, the film was dried under reduced pressure in a vacuum dryer at 50°C for 8 hours and at 110°C for 8 hours to remove the solvent, yielding a resin film with a thickness of 50 μm to 100 μm. A film sample measuring 40 mm in length and 6 mm in width (with a 2 mm width at the neck) was prepared from the dried resin film using a punching tool for tensile testing. Using this film sample, the breaking strength and breaking elongation of each polymer were measured. The breaking strength and breaking elongation were measured using a tabletop tensile tester (manufactured by Shimadzu Corporation, product name "EZgraph") at a tension speed of 1 mm / min.

[0275] (Elastic Power of Polymer) The elastic power (unit: %) of each polymer produced in the above Examples and Comparative Examples was measured as follows. First, each polymer (2 g) was dissolved in methylene chloride (12 mL) and cast onto a commercially available polyethylene terephthalate film (PET film) using an applicator to form a film. This film was heated under reduced pressure to remove the solvent, and a film sample with a polymer film formed thereon measuring 100 mm x 100 mm x approximately 30 μm thick was obtained. The elastic power was evaluated using the cast surface of the prepared film sample. A nanoindentation tester (manufactured by Elionix Co., Ltd., product name "ENT-1100a") was used to evaluate the elastic power. The conditions for measuring the elastic power were as follows: Measurement temperature: 28°C Indenter: Vickers indenter Test load: 0.6 mN

[0276] (Abrasion Resistance of Polymer) The abrasion resistance of each polymer produced in the above Examples and Comparative Examples was measured as follows. Each polymer (2 g) was dissolved in methylene chloride (12 mL) and cast onto a commercially available PET film using an applicator. The film was heated under reduced pressure to remove the solvent, yielding a film sample with a 100 mm x 100 mm x approximately 30 μm thick polymer film formed thereon. Abrasion resistance was evaluated using the cast surface of the prepared film sample. Using a Suga abrasion tester (manufactured by Suga Test Instruments Co., Ltd., product name "NUS-ISO3"), an abrasion wheel (the surface of which was coated with aluminum oxide having a particle size of 3 μm) was brought into contact with the film sample under a load of 50 g as the evaluation condition, and the mass loss (unit: mg) was measured after 2,000 revolutions.

[0277] (Production of Coating Solution and Electrophotographic Photoreceptor) An electrophotographic photoreceptor was produced using a PET film vapor-deposited with aluminum metal as the conductive substrate. A charge generation layer and a charge transport layer were sequentially laminated on the surface of the aluminum metal layer to form a laminated photosensitive layer. 0.5 parts by mass of oxotitanium phthalocyanine was used as the charge generation material, and 0.5 parts by mass of butyral resin was used as the binder resin. These charge generation material and binder resin were added to 19 parts by mass of methylene chloride as the solvent and dispersed using an ultrasonic vibrator. This dispersion was applied to the film surface of the conductive substrate using a bar coater, and the coating was dried to form a charge generation layer with a thickness of approximately 0.5 μm. Next, 0.5 g of the following compound (CTM-1) as the charge transport material and 0.5 g of each polymer were dispersed in 10 mL of methylene chloride to prepare a coating solution. This coating liquid was applied onto the charge generating layer using an applicator, and the coating was dried to form a charge transport layer having a thickness of about 20 μm.

[0278]

[0279] (Charging Characteristics of PC-PAR Copolymer) The electrophotographic characteristics of the electrophotographic photoreceptor manufactured as described above were measured using an electrostatic charging tester (manufactured by Gentec Co., Ltd., product name "CYNTHIA54IM"). The initial surface potential V ０(unit: V), and residual potential after 5 seconds of light irradiation (10 Lux) (initial residual potential V Ｒ (unit: V)) was measured. ０ and initial residual potential V Ｒ The initial surface potential V ０ The electrophotographic photosensitive member having an initial residual potential V of −600 V or less was evaluated as A, and the electrophotographic photosensitive member having an initial residual potential V of more than −600 V was evaluated as C. Ｒ The electrophotographic photosensitive member having a voltage of −60 V or more (an absolute value of 60 V or less) was evaluated as A, and the electrophotographic photosensitive member having a voltage of less than −60 V (an electrophotographic photosensitive member having an absolute value of more than 60 V) was evaluated as C.

[0280]

[0281] [Evaluation Results] Comparing the PC-PAR polymers of Examples 1 to 3 with the PAR polymers of Comparative Examples 1 and 2 and the PC polymer of Comparative Example 3, the PC-PAR polymers of Examples 1 to 3 exhibited excellent solubility in tetrahydrofuran (THF) and good abrasion resistance. For example, the PC-PAR polymer of Example 1, by using a bischloroformate oligomer having 1,1-bis-(4-hydroxy-3-methylphenyl)cyclohexane in combination with 2,6-naphthalenedicarboxylic acid dichloride, not only improved solubility compared to the PAR polymer of Comparative Example 1, but also improved breaking strength, which is related to abrasion resistance. Furthermore, the PC-PAR polymer of Example 2, by using 26NP and 14NP in combination as dicarboxylic acid dichloride components, improved solubility while maintaining a good level of abrasion resistance. Comparing the PC-PAR polymer of Example 1 with the PC polymer of Comparative Example 3, the types of bonding sites on the naphthalene skeleton differ. The type of bonding site on the naphthalene skeleton was a carbonate bond in Comparative Example 3, whereas it was an arylate bond in Example 1. As a result, the elastic power, elongation at break, and strength at break, which contribute to the abrasion resistance of the PC-PAR polymer of Example 1, were all improved, and the abrasion resistance was significantly improved. From the above, it was shown that the PC-PAR polymer according to the present invention has significantly improved abrasion resistance and various properties contributing to the abrasion resistance, without impairing solubility in solvents, compared to the PAR copolymer and PC copolymer.

[0282] The polycarbonate polyarylate polymer of the present invention can be suitably used as a binder resin for the photosensitive layer of an electrophotographic photoreceptor. Furthermore, a photoreceptor drum made using the electrophotographic photoreceptor of the present invention can be suitably used in electrical equipment such as copiers and laser printers.

Claims

1. A polycarbonate polyarylate resin comprising at least one of structural units represented by the following general formulas (A1) and (A2), a structural unit represented by the following general formula (B1), and a structural unit represented by the following general formula (C1), wherein the molar fraction ax of the structural unit represented by the following general formula (A1), the molar fraction ay of the structural unit represented by the following general formula (A2), and the molar fraction c of the structural unit represented by the following general formula (C1) satisfy the following formula (1): 0.1≦{(ax+ay) / (ax+ay+c)}×100<50 ... (1) (In the above general formulae (A1) and (A2), R １３ and R １４ each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group; n represents 0, 1, 2, or 3, and １３ are the same or different from each other, m represents 0, 1, 2, 3 or 4, and a plurality of R １４ are the same or different from each other, in the general formula (B1), b is a mole fraction of the structural unit represented by the general formula (B1), the structural unit represented by the general formula (B1) is different from the carbonyl group in the general formulas (A1) and (A2), in the general formula (C1), Cx is a divalent group containing a substituted or unsubstituted divalent aromatic hydrocarbon group, with the proviso that Cx in the structural unit represented by the general formula (C1) does not consist solely of a divalent group represented by the following general formula (C3), in the general formulas (A1), (A2), (B1) and (C1), * represents a bond, when the polycarbonate polyarylate resin contains a plurality of structural units represented by the general formula (A1), the plurality of structural units represented by the general formula (A1) are the same or different from each other, and when the polycarbonate polyarylate resin contains a plurality of structural units represented by the general formula (A2), the plurality of structural units represented by the general formula (A2) are the same or different from each other, When the compound contains a plurality of structural units represented by the general formula (C1), the plurality of structural units represented by the general formula (C1) are the same or different from each other. (In the general formula (C3), R １６１ ~R １６８ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, a cyano group, and a carboxy group; * represents a bond; and when a plurality of divalent groups represented by general formula (C3) are present, the plurality of divalent groups represented by general formula (C3) are the same or different from each other. ) 2. The polycarbonate polyarylate resin according to claim 1, comprising a structural unit represented by the general formula (A1).

3. The polycarbonate polyarylate resin according to claim 1 or 2, which does not contain a structural unit represented by the general formula (A2).

4. A polycarbonate polyarylate resin according to any one of claims 1 to 3, wherein the structural unit represented by the general formula (A1) includes at least one structural unit represented by the following general formulas (A11) and (A12): (R in the general formula (A11) １３１ ~R １３６ and R in the general formula (A12) １５１ ~R １５６ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group, In the general formula (A12), at is the molar fraction of the structural unit represented by the general formula (A12), and * in the general formulas (A11) and (A12) represents a bond.

5. A polycarbonate polyarylate resin according to claim 4, wherein the structural unit represented by the general formula (A1) includes a structural unit represented by the general formula (A11).

6. The polycarbonate polyarylate resin according to claim 4 or 5, wherein the molar fraction as of the structural unit represented by the general formula (A11) and the molar fraction at of the structural unit represented by the general formula (A12) satisfy the following formula (Mathematical formula 1B): 10≦{as / (as+at)}×100≦100 ... (Mathematical formula 1B).

7. A polycarbonate polyarylate resin according to any one of claims 1 to 6, wherein the structural unit represented by the general formula (C1) includes at least one structural unit represented by the following general formulas (C11) and (C12): (R in the general formula (C11) １７１ ~R １７８ and R in the general formula (C12) １７９ ~R １８２ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms; R １７１ ~R １７８ and R １７９ ~R １８２ are the same or different, X is (i) a single bond, (ii) a substituted or unsubstituted alkylene group having 1 to 28 carbon atoms, a substituted or unsubstituted alkylidene group having 2 to 28 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 15 ring carbon atoms, a substituted or unsubstituted cycloalkylidene group having 3 to 26 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 ring carbon atoms, -S-, -SO-, -SO ２ (iii) a divalent group formed by linking two or more groups selected from the group (ii), cx in the general formula (C11) is the molar fraction of the structural unit represented by the general formula (C11), cy in the general formula (C12) is the molar fraction of the structural unit represented by the general formula (C12), and * in the general formulas (C11) and (C12) represents a bond.

8. A polycarbonate polyarylate resin according to claim 7, wherein the structural unit represented by the general formula (C1) includes a structural unit represented by the general formula (C11).

9. The polycarbonate polyarylate resin according to claim 7 or 8, wherein the structural unit represented by general formula (C1) includes a structural unit represented by the following general formula (C111): (In the above general formula (C111), R １７１ ~R １７８ , cx and * each represent R in the general formula (C11). １７１ ~R １７８ , cx and * are synonymous, R １２１ ~R １３０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * represents a bond.

10. A polycarbonate polyarylate resin according to claim 1, wherein the structural unit represented by general formula (A1) includes a structural unit represented by the following general formula (A11), and the structural unit represented by general formula (C1) includes a structural unit represented by the following general formula (C111): (R in the general formula (A11) １３１ ~R １３６ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aralkyloxy group having 7 to 20 carbon atoms, a nitro group, an aldehyde group, or a cyano group, in which as in general formula (A11) represents a mole fraction of the structural unit represented by general formula (A11), * in general formula (A11) represents a bond, and R in general formula (C111) represents a hydrogen atom, １７１ ~R １７８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, cx in general formula (C111) represents a molar fraction of the structural unit represented by general formula (C111), R １２１ ~R １３０ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted cycloalkoxy group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, and * in formula (C111) represents a bond.

11. The polycarbonate polyarylate resin according to any one of claims 1 to 10, having a reduced viscosity [ηsp / C] of 0.15 dL / g or more and 5.75 dL / g or less.

12. A coating composition comprising the polycarbonate polyarylate resin according to any one of claims 1 to 11 and an organic solvent.

13. The coating composition according to claim 12, further comprising a charge transport material.

14. A molded article comprising the polycarbonate polyarylate resin according to any one of claims 1 to 11.

15. An electrophotographic photoreceptor comprising the polycarbonate polyarylate resin according to any one of claims 1 to 11 in its outermost layer.

16. An electrophotographic photoreceptor comprising: a conductive substrate; and a photosensitive layer provided on the conductive substrate, the photosensitive layer containing the polycarbonate polyarylate resin according to any one of claims 1 to 11.

17. An electrophotographic photoreceptor according to claim 16, wherein the photosensitive layer has a charge transport layer and a charge generation layer included between the charge transport layer and the conductive substrate, and the charge transport layer contains the polycarbonate polyarylate resin.

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