Hydrazone derivative of triphenylamine and electrophotographic photosensitive member
US-2015378269-A1 · Dec 31, 2015 · US
US2024411237A1 · US · A1
| Field | Value |
|---|---|
| Publication number | US-2024411237-A1 |
| Application number | US-202418434864-A |
| Country | US |
| Kind code | A1 |
| Filing date | Feb 7, 2024 |
| Priority date | Jun 9, 2023 |
| Publication date | Dec 12, 2024 |
| Grant date | — |
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An electrophotographic photoreceptor includes a conductive substrate, an undercoat layer disposed on the conductive substrate, and a photosensitive layer disposed on the undercoat layer, in which the undercoat layer contains a binder resin and at least one perinone compound selected from the group consisting of a compound represented by Formula (1) and a compound represented by Formula (2), the photosensitive layer contains a polyester resin (1) having at least one dicarboxylic acid unit (A) selected from the group consisting of a dicarboxylic acid unit (A2) represented by Formula (A2), a dicarboxylic acid unit (A3) represented by Formula (A3), and a dicarboxylic acid unit (A4) represented by Formula (A4), and a diol unit (B) represented by Formula (B), and a mass proportion of the polyester resin (1) in the photosensitive layer is 15% by mass or greater, in Formula (1), R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , and R 18 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryl group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, or a halogen atom, R 11 and R 12 , R 12 and R 13 , and R 13 and R 14 may be each independently linked to each other to form a ring, and R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may be each independently linked to each other to form a ring, in Formula (2), R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , and R 28 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryl group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, or a halogen atom, R 21 and R 22 , R 22 and R 23 , and R 23 and R 24 may be each independently linked to each other to form a ring, and R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 may be each independently linked to each other to form a ring, in Formula (A2), n 201 and n 202 each independently represent an integer of 0 or greater and 4 or less, and n 201 pieces of Ra 201 's and n 202 pieces of Ra 202 's each independently represent an alkyl group having 1 or more and 10 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an alkoxy group having 1 or more and 6 or less carbon atoms, in Formula (A3), n 301 and n 302 each independently represent an integer of 0 or greater and 4 or less, and n 301 pieces of Ra 301 's and n 302 pieces of Ra 302 's each independently represent an alkyl group having 1 or more and 10 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an alkoxy group having 1 or more and 6 or less carbon atoms, in Formula (A4), n 401 represents an integer of 0 or greater and 6 or less, and n 401 pieces of Ra 401 's each independently represent an alkyl group having 1 or more and 10 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an alkoxy group having 1 or more and 6 or less carbon atoms, in Formula (B), Ar B1 and Ar B2 each independently represent an aromatic ring that may have a substituent, L B represents a single bond, an oxygen atom, a sulfur atom, or —C(Rb 1 )(Rb 2 )—, and n B1 represents 0, 1, or 2. Rb 1 and Rb 2 each independently represent a hydrogen atom, an alkyl group having 1 or more and 20 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an aralkyl group having 7 or more and 20 or less carbon atoms, and Rb 1 and Rb 2 may be bonded to each other to form a cyclic alkyl group.
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What is claimed is: 1 . An electrophotographic photoreceptor comprising: a conductive substrate; an undercoat layer disposed on the conductive substrate; and a photosensitive layer disposed on the undercoat layer, wherein the undercoat layer contains a binder resin and at least one perinone compound selected from the group consisting of a compound represented by Formula (1) and a compound represented by Formula (2), the photosensitive layer contains a polyester resin (1) having at least one dicarboxylic acid unit (A) selected from the group consisting of a dicarboxylic acid unit (A2) represented by Formula (A2), a dicarboxylic acid unit (A3) represented by Formula (A3), and a dicarboxylic acid unit (A4) represented by Formula (A4), and a diol unit (B) represented by Formula (B), and a mass proportion of the polyester resin (1) in the photosensitive layer is 15% by mass or greater, in Formula (1), R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , and R 18 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryl group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, or a halogen atom, R 11 and R 12 , R 12 and R 13 , and R 13 and R 14 may be each independently linked to each other to form a ring, and R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may be each independently linked to each other to form a ring, in Formula (2), R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , and R 28 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryl group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkoxycarbonylalkyl group, an aryloxycarbonylalkyl group, or a halogen atom, R 21 and R 22 , R 22 and R 23 , and R 23 and R 24 may be each independently linked to each other to form a ring, and R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 may be each independently linked to each other to form a ring, in Formula (A2), n 201 and n 202 each independently represent an integer of 0 or greater and 4 or less, and n 201 pieces of Ra 201 's and n 202 pieces of Ra 202 's each independently represent an alkyl group having 1 or more and 10 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an alkoxy group having 1 or more and 6 or less carbon atoms, in Formula (A3), n 301 and n 302 each independently represent an integer of 0 or greater and 4 or less, and n 301 pieces of Ra 301 's and n 302 pieces of Ra 302 's each independently represent an alkyl group having 1 or more and 10 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an alkoxy group having 1 or more and 6 or less carbon atoms, in Formula (A4), n 401 represents an integer of 0 or greater and 6 or less, and n 401 pieces of Ra 401 's each independently represent an alkyl group having 1 or more and 10 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an alkoxy group having 1 or more and 6 or less carbon atoms, in Formula (B), Ar B1 and Ar B2 each independently represent an aromatic ring that may have a substituent, L B represents a single bond, an oxygen atom, a sulfur atom, or —C(Rb 1 )(Rb 2 )—, and n B1 represents 0, 1, or 2, Rb 1 and Rb 2 each independently represent a hydrogen atom, an alkyl group having 1 or more and 20 or less carbon atoms, an aryl group having 6 or more and 12 or less carbon atoms, or an aralkyl group having 7 or more and 20 or less carbon atoms, and Rb 1 and Rb 2 may be bonded to each other to form a cyclic alkyl group. 2 . The electrophotographic photoreceptor according to claim 1 , wherein a mass proportion of the perinone compound in the undercoat layer is 30% by mass or greater and 90% by mass or less. 3 . The electrophotographic photoreceptor according to claim 1 , wherein the undercoat layer contains polyurethane. 4 . The electrophotographic photoreceptor according to claim 1 , wherein the undercoat layer has an average thickness of 5 μm or greater and 30 μm or less. 5 . The electrophotographic photoreceptor according to claim 1 , wherein the photosensitive layer further contains a polycarbonate resin. 6 . The electrophotographic photoreceptor according to claim 1 , wherein the polyester resin (1) has the diol unit (B) including at least one selected from the group consisting of a diol unit (B1) represented by Formula (B1), a diol unit (B2) represented by Formula (B2), a diol unit (B3) represented by Formula (B3), a diol unit (B4) represented by Formula (B4), a diol unit (B5) represented by Formula (B5), a diol unit (B6) represented by Formula (B6), a diol unit (B7) represented by Formula (B7), and a diol unit (B8) represented by Formula (B8), in Formula (B1), Rb 101 represents a branched alkyl group having 4 or more and 20 or less carbon atoms, Rb 201 represents a hydrogen atom or an alkyl group having 1 or more and 3 or less carbon atoms, and Rb 401 , Rb 501 , Rb 801 , and Rb 901 each independently represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an alkoxy group having 1 or more and 6 or less carbon atoms, or a halogen atom, in Formula (B2), Rb 102 represents a linear alkyl group having 4 or more and 20 or less carbon atoms, Rb 202 represents a hydrogen atom or an alkyl group having 1 or more and 3 or less carbon atoms, and Rb 402 , Rb 502 , Rb 802 , and Rb 902 each independently represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an alkoxy group having 1 or more and 6 or less carbon atoms, or a halogen atom, in Formula (B3), Rb 113 and Rb 213 each independently represent a hydrogen atom, a linear alkyl group having 1 or more and 3 or less carbon atoms, an alkoxy group having 1 or more and 4 or less carbon atoms, or a halogen atom, d represents an integer of 7 or greater and 15 or less, and Rb 403 , Rb 503 , Rb 803 , and Rb 903 each independently represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an alkoxy group having 1 or more and 6 or less carbon atoms, or a halogen atom, in Formula (B4), Rb 104 and Rb 204 each independently represent a hydrogen atom, an alkyl group having 1 or more and 3 or less carbon atoms, and Rb 404 , Rb 504 , Rb 804 , and Rb 904 each independently represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an alkoxy group having 1 or more and 6 or less carbon atoms, or a halogen atom, in Formula (B5), Ar 105 represents an aryl group having 6 or more and 12 or less carbon atoms or an aralkyl group having 7 or more and 20 or less carbon atoms, Rb 205 represents a hydrogen atom or an alkyl group having 1 or more and 3 or less carbon atoms, and Rb 405 , Rb 505 , Rb 805 , and Rb 905 each independently represent a hydrogen atom, an alkyl group having 1 or more and 4 or less carbon atoms, an alkoxy group having 1 or more and 6 or less carbon atoms, or a halogen atom, in Formula (B6), Rb 116 and Rb 216 each independently represent a hydrogen atom, a linear alkyl group having 1 or more and 3 or less carbon atoms, an alkoxy group having 1 or more and 4 or less carbon atoms, or a halogen atom, e represents an integer of 4 or g
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