Photoelectric conversion element, imaging element, optical sensor, and compound
AssigneeFUJIFILM Corporation
InventorsHiroki Sugiura, Yasunori Yonekuta
Life of this patent
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Abstract
A first object of the present invention is to provide a photoelectric conversion element having a high external quantum efficiency and small variation in response. A second object of the present invention is to provide an imaging element, an optical sensor, and a compound related to the photoelectric conversion element. The photoelectric conversion element includes, in the following order, a conductive film, a photoelectric conversion film, and a transparent conductive film, in which the photoelectric conversion film contains a compound represented by Formula (1).
Claims18
A photoelectric conversion element comprising, in the following order:
- a conductive film;
- a photoelectric conversion film;
- and
- a transparent conductive film,
- wherein the photoelectric conversion film contains a compound represented by Formula (1),
- in Formula (1), A11 represents a divalent conjugate group having a cyclic structure,
- R11 and R12 each independently represent a hydrogen atom or a monovalent substituent,
- T11 and T12 each independently represent a group represented by any of Formulae (T1) to (T3),
- in Formula (T1), X11 and X12 each independently represent-CN, —S(═O)2R13, —S(═O) R13, —C(═O) R14, —C(═O) OR14, —C(═S) R14, —C(═S) OR14, —C(═O) SR14, —C(═O) N(R15)2, —C(═S) N(R15)2, or —S(═O)2N(R15)2, R13 and R14 each independently represent a monovalent substituent, R15 represents a hydrogen atom or a monovalent substituent,
- in Formula (T2) and Formula (T3), Zx1 and Zx2 each independently represent >C═O, >C═S, >C═C(CN)2, >S(═O)2, >S(═O), >C═C[S(═O)2R15]2, >C═C[S(═O) R15]2, >C═C[C(═O) R15]2, >C═C[CN][S(═O)2R15], >C═C[CN][S(═O) R15], >C═C[CN][C(═O) R15], >C═C[C(═O) R15] [S(═O)2R15], or >C═C[C(═O) R15] [S(═O) R15], R15 represents a monovalent substituent,
- in Formula (T2), Cyx1 represents a ring containing at least one carbon atom and a ring-constituting atom in Zx1, which may have a substituent,
- in Formula (T3), Cyx2 represents a ring containing at least three carbon atoms and a ring-constituting atom in Zx2, which may have a substituent,
- in Formula (T3), Rx1 and Rx2 each independently represent a hydrogen atom or a monovalent substituent,
- in Formulae (T1) to (T3), * represents a bonding position,
- Q11 and Q12 each independently represent a quinoid-type conjugate linking group represented by Formula (Q),
- in Formula (Q), Cyx3 represents a 5- to 10-membered ring containing at least one or more double bonds, * represents a bonding position, s represents an integer of 1 to 10,
- where, in a case where s Cyx3's in Formula (Q) are represented as N1 to Ns from one double bond toward the other double bond, Formula (Q) satisfies conditions (A) to (D) as follows:
- (A) in a case where s represents 1, Cyx3 of N1 forms a quinoid structure together with two double bonds bonded to Cyx3 of N1;
- (B) in a case where s represents 2, Cyx3 of N1 and Cyx3 of N2 are fused with each other, Cyx3 of N1 forms a quinoid structure together with a double bond bonded to Cyx3 of N1 and a double bond contained in Cyx3 of N2, and Cyx3 of N2 forms a quinoid structure together with a double bond contained in Cyx3 of N1 and contributing to the formation of the quinoid structure by Cyx3 of N1, and a double bond bonded to Cyx3 of N2;
- (C) in a case where s represents an integer of 3 or more, Cyx3's of N1 to Ns are fused with each other, Cyx3 of N1 forms a quinoid structure together with a double bond bonded to Cyx3 of N1 and a double bond contained in Cyx3 of N2, in a case where t is an integer of 2 to (s−1), Cyx3's of Nt each form a quinoid structure together with a double bond contained in Cyx3 of Nt−1 and contributing to a formation of a quinoid structure by Cyx3 of Nt−1 and a double bond contained in Cyx3 of Nt+1, and Cyx3 of Ns forms a quinoid structure together with a double bond contained in Cyx3 of Ns-1 and contributing to a formation of a quinoid structure by Cyx3 of Ns-1, and a double bond bonded to Cyx3 of Ns;
- and
- (D) Formula (Q) does not contain the following structures,
- in Formulae, R represents an organic group, *1 represents a bonding position with T11 or T12, * represents another bonding position, and
- n11 and n12 each independently represent an integer of 1 or more,
- where the compound represented by Formula (1) does not contain a carboxy group, a sulfonic acid group, and a phosphoric acid group, and salts thereof.
A compound represented by Formula (1),
- in Formula (1), A11 represents a divalent conjugate group having a cyclic structure,
- R11 and R12 each independently represent a hydrogen atom or a monovalent substituent,
- T11 and T12 each independently represent a group represented by any of Formulae (T1) to (T3),
- in Formula (T1), X11 and X12 each independently represent-CN, —S(═O)2R13, —S(═O) R13, —C(═O) R14, —C(═O) OR14, —C(═S) R14, —C(═S) OR14, —C(═O) SR14, —C(═O) N(R15)2, —C(═S) N(R15)2, or —S(═O)2N(R15)2, R13 and R14 each independently represent a monovalent substituent, R15 represents a hydrogen atom or a monovalent substituent,
- in Formula (T2) and Formula (T3), Zx1 and Zx2 each independently represent >C═O, >C═S, >C═C(CN)2, >S(═O)2, >S(═O), >C═C[S(═O)2R15]2, >C═C[S(═O) R15]2, >C═C[C(═O) R15]2, >C═C[CN][S(═O)2R15], >C═C[CN][S(═O) R15], >C═C[CN][C(═O) R15], >C═C[C(═O) R15] [S(═O)2R15], or >C═C[C(═O) R15] [S(═O) R15], R15 represents a monovalent substituent,
- in Formula (T2), Cyx1 represents a ring containing at least one carbon atom and a ring-constituting atom in Zx1, which may have a substituent,
- in Formula (T3), Cyx2 represents a ring containing at least three carbon atoms and a ring-constituting atom in Zx2, which may have a substituent,
- in Formula (T3), Rx1 and Rx2 each independently represent a hydrogen atom or a monovalent substituent,
- in Formulae (T1) to (T3), * represents a bonding position,
- Q11 and Q12 each independently represent a quinoid-type conjugate linking group represented by Formula (Q),
- in Formula (Q), Cyx3 represents a 5- to 10-membered ring containing at least one or more double bonds, * represents a bonding position, s represents an integer of 1 to 10,
- where, in a case where s Cyx3's in Formula (Q) are represented as N1 to Ns numbers from one double bond toward the other double bond, Formula (Q) satisfies conditions (A) to (D) as follows:
- (A) in a case where s represents 1, Cyx3 of N1 forms a quinoid structure together with two double bonds bonded to Cyx3 of N1;
- (B) in a case where s represents 2, Cyx3 of N1 and Cyx3 of N2 are fused with each other, Cyx3 of N1 forms a quinoid structure together with a double bond bonded to Cyx3 of N1 and a double bond contained in Cyx3 of N2, Cyx3 of N2 forms a quinoid structure together with a double bond contained in Cyx3 of N1 and contributing to the formation of the quinoid structure by Cyx3 of N1, and a double bond bonded to Cyx3 of N2;
- (C) in a case where s represents an integer of 3 or more, Cyx3's of N1 to Ns are fused with each other, Cyx3 of N1 forms a quinoid structure together with a double bond bonded to Cyx3 of N1 and a double bond contained in Cyx3 of N2, in a case where t is an integer of 2 to (s−1), Cyx3's of Nt each form a quinoid structure together with a double bond contained in Cyx3 of Nt−1 and contributing to a formation of a quinoid structure by Cyx3 of Nt−1 and a double bond contained in Cyx3 of Nt+1, and Cyx3 of Ns forms a quinoid structure together with a double bond contained in Cyx3 of Ns-1 and contributing to a formation of a quinoid structure by Cyx3 of Ns-1, and a double bond bonded to Cyx3 of Ns;
- and
- (D) Formula (Q) does not contain the following structures,
- in Formulae, R represents an organic group, *1 represents a bonding position with T11 or T12, * Represents another bonding position,
- n11 and n12 each independently represent an integer of 1 or more, and
- where the compound represented by Formula (1) does not contain a carboxy group, a sulfonic acid group, and a phosphoric acid group, and salts thereof.
Dependencies are inferred from the claim text.