Photoelectric conversion element, imaging element, imaging element production method, optical sensor, and compound

Abstract

The present invention provides a photoelectric conversion element which has excellent sensitivity with respect to blue / green light, and an imaging element, an imaging element production method, an optical sensor, and a compound which relate to the photoelectric conversion element. A photoelectric conversion element according to the present invention comprises a photoelectric conversion element conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains a compound represented by formula (1).

Description

Photoelectric conversion element, imaging element, imaging element manufacturing method, optical sensor, compound

[0001] The present invention relates to a photoelectric conversion element, an imaging element, a method for manufacturing an imaging element, an optical sensor, and a compound.

[0002] In recent years, development of organic electronic devices, such as elements having a photoelectric conversion film and organic electroluminescence (EL) elements, has progressed. For example, Patent Document 1 discloses a photoelectric conversion element, an imaging element, and an electronic device that contain a compound having a specific structure represented by formula (1) as a photoelectric conversion element that selectively absorbs light in the green wavelength region and has excellent photoelectric conversion efficiency.

[0003] European Patent No. 3252051

[0004] On the other hand, with the demand for improved performance of image sensors, optical sensors, and the like, there is a demand for photoelectric conversion elements that exhibit excellent characteristics. One of the characteristics required for a photoelectric conversion element is, for example, excellent sensitivity to blue-green light. In response to this demand, the present inventors prepared and investigated a photoelectric conversion element using the compound disclosed in Patent Document 1, and found that the sensitivity to blue-green light needed to be improved. The blue-green light referred to above refers to light with a wavelength of 450 to 560 nm.

[0005] Therefore, an object of the present invention is to provide a photoelectric conversion element having excellent sensitivity to blue-green light. Another object of the present invention is to provide an imaging element, a method for manufacturing an imaging element, an optical sensor, and a compound related to the photoelectric conversion element.

[0006] As a result of extensive research into solving the above problems, the present inventors have found that the problems can be solved by the following configuration.

[0007] [1] A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains a compound represented by formula (1) described later. [2] The photoelectric conversion element according to [1], wherein the group represented by formula (A-1) is a group represented by formula (A-3) described later or formula (A-4) described later, and the group represented by formula (A-2) is a group represented by formula (A-5) described later. [3] The photoelectric conversion element according to [2], wherein the group represented by formula (A-3) is a group represented by formula (C-1) described later or formula (C-2) described later, the group represented by formula (A-4) is a group represented by formula (C-3) described later, and the group represented by formula (A-5) is a group represented by formula (C-4) described later. [4] In formula (1), B １ is a group represented by any one of formula (B1-1) described later, formula (B2-1) described later, formula (B3-1) described later, formula (B4-1) to formula (B4-3) described later, formula (B5-1) to formula (B5-3) described later, and formula (B6) above. [5] The photoelectric conversion element according to any one of [1] to [4], wherein the compound represented by formula (1) above is a compound represented by formula (2) described later. [6] In formula (1) above, X １ and Z １ is a sulfur atom, and R Ｚ１ and R Ｚ２is the aromatic ring group which may have a substituent. [7] The photoelectric conversion element according to any one of [1] to [5], wherein in the formula (2), the aromatic ring group which may have a substituent is a group represented by formula (S1) described below. [8] The photoelectric conversion element according to any one of [1] to [7], wherein the photoelectric conversion film further contains an n-type organic semiconductor, and the photoelectric conversion film has a bulk heterostructure formed by mixing a compound represented by formula (1) described below with the n-type organic semiconductor. [9] The photoelectric conversion element according to [8], wherein the n-type organic semiconductor contains fullerenes selected from the group consisting of fullerenes and derivatives thereof.

[10] The photoelectric conversion element according to any one of [1] to [9], wherein the photoelectric conversion film further contains a p-type organic semiconductor.

[11] The photoelectric conversion element according to any one of [1] to

[10] , wherein the photoelectric conversion film further contains a dye.

[12] The photoelectric conversion element according to

[11] , wherein the dye is a compound represented by formula (D1) described later.

[13] The photoelectric conversion element according to any one of [1] to

[12] , wherein one or more intermediate layers are provided between the conductive film and the transparent conductive film in addition to the photoelectric conversion film.

[14] An imaging element comprising the photoelectric conversion element according to any one of [1] to

[13] .

[15] An optical sensor comprising the photoelectric conversion element according to any one of [1] to

[13] .

[16] A method for manufacturing an imaging element, comprising a step of manufacturing the photoelectric conversion element according to any one of [1] to

[13] .

[17] A compound represented by formula (1) described later.

[18] The compound according to

[17] , wherein the group represented by formula (A-1) is a group represented by formula (A-3) described later or formula (A-4) described later, and the group represented by formula (A-2) is a group represented by formula (A-5) described later.

[19] The compound according to

[18] , wherein the group represented by the formula (A-3) is a group represented by the formula (C-1) or the formula (C-2) described later, the group represented by the formula (A-4) is a group represented by the formula (C-3) described later, and the group represented by the formula (A-5) is a group represented by the formula (C-4) described later.

[20] In the formula (1), B １is a group represented by any one of formula (B1-1) described later, formula (B2-1) described later, formula (B3-1) described later, formula (B4-1) to formula (B4-3) described later, formula (B5-1) to formula (B5-3) described later, and formula (B6) above.

[21] The compound according to any one of

[17] to

[20] above, wherein the compound represented by formula (1) is a compound represented by formula (2) described later.

[22] In formula (1), X １ and Z １ is a sulfur atom, and R Ｚ１ and R Ｚ２

[23] The compound according to

[21] or

[22] , wherein in the formula (2), the aromatic ring group which may have a substituent is a group represented by formula (S1) described below.

[0008] According to the present invention, a photoelectric conversion element having excellent sensitivity to blue-green light can be provided. Furthermore, according to the present invention, an imaging element, a manufacturing method of an imaging element, an optical sensor, and a compound related to the photoelectric conversion element can also be provided.

[0009] 1 is a schematic cross-sectional view illustrating an example of the configuration of a photoelectric conversion element.

[0010] The present invention will be described in detail below. The following description of the components may be based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.

[0011] The meaning of each description in this specification is as follows. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the lower and upper limits. In this specification, a hydrogen atom may be a protist atom (a normal hydrogen atom) or a deuterium atom (for example, a deuterium atom, etc.).

[0012] In this specification, with respect to compounds that may have geometric isomers (cis-trans isomers), the general formula or structural formula representing the compound may be described in only one of the cis and trans forms for convenience. Even in such cases, unless otherwise specified, the form of the compound is not limited to either the cis or trans form, and the compound may be in either the cis or trans form.

[0013] Unless otherwise specified, the bonding direction of a divalent group (e.g., -CO-O-) represented in this specification is not limited. For example, when Y is -CO-O- in a compound represented by the formula "X-Y-Z," the compound may be either "X-O-CO-Z" or "X-CO-O-Z."

[0014] The symbol "*" shown in a chemical formula represents a bonding position unless otherwise specified. In this specification, when there are multiple substituents and linking groups, etc. (hereinafter also referred to as "substituents, etc.") represented by a specific symbol, or when multiple substituents, etc. are specified at the same time, it means that the respective substituents, etc. may be the same or different from each other. This also applies to the specification of the number of substituents, etc. In this specification, unless otherwise specified, "substituents" include, for example, groups exemplified as the substituent W described below.

[0015] (Substituent W) The substituent W in this specification will be described. Examples of the substituent W include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, an aryl group, a heterocyclic group (a heteroaryl group, or an aliphatic heterocyclic group), a cyano group, a nitro group, an alkoxy group, an aryloxy group, a silyl group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryl ... Examples of the substituent W include an alkyloxy group, a primary, secondary, or tertiary amino group (including an anilino group), an alkylthio group, an arylthio group, a heterocyclic thio group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a phosphono group, a carboxy group, a phosphate group, a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, and a boronic acid group. Furthermore, each of the above groups may further have a substituent (e.g., one or more of the above groups, etc.), if possible. For example, an alkyl group which may have a substituent is also included as one form of the substituent W. Furthermore, when the substituent W has a carbon atom, the number of carbon atoms contained in the substituent W is, for example, 1 to 20. The number of atoms other than hydrogen atoms contained in the substituent W is, for example, 1 to 30. The specific compounds described below may have, as a substituent, a carboxy group, a salt of a carboxy group, a salt of a phosphate group, a sulfonic acid group, a salt of a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, a boronic acid group (-B(OH) ２ ) and / or has no primary amino groups.

[0016] In this specification, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group. Furthermore, in this specification, unless otherwise specified, the number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6. The alkyl group may be linear, branched, or cyclic. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclopropyl group, and a cyclopentyl group. Furthermore, the alkyl group may be a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have these ring structures as partial structures. In the alkyl group that may have a substituent, examples of the substituent that the alkyl group may have include the groups exemplified for the substituent W. Of these, an aryl group (preferably having 6 to 18 carbon atoms, more preferably having 6 carbon atoms), a heteroaryl group (preferably having 4 to 18 carbon atoms, more preferably having 5 to 6 carbon atoms), or a halogen atom (preferably a fluorine atom or a chlorine atom) is preferred.

[0017] In this specification, unless otherwise specified, the alkyl group moiety in the alkoxy group is preferably the above-mentioned alkyl group. The alkyl group moiety in the alkylthio group is preferably the above-mentioned alkyl group. In the alkoxy group which may have a substituent, examples of the substituent that the alkoxy group may have include the same as the substituent in the alkyl group which may have a substituent. In the alkylthio group which may have a substituent, examples of the substituent that the alkylthio group may have include the same as the substituent in the alkyl group which may have a substituent.

[0018] In this specification, unless otherwise specified, the alkenyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkenyl group is preferably 2 to 20. In the alkenyl group which may have a substituent, examples of the substituent that the alkenyl group may have include the same as the substituents in the alkyl group which may have a substituent. In this specification, unless otherwise specified, the alkynyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkynyl group is preferably 2 to 20. In the alkynyl group which may have a substituent, examples of the substituent that the alkynyl group may have include the same as the substituents in the alkyl group which may have a substituent.

[0019] In this specification, unless otherwise specified, an aromatic ring or an aromatic ring constituting an aromatic ring group may be either a monocyclic ring or a polycyclic ring (e.g., 2 to 6 rings, etc.). A monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as a ring structure. A polycyclic (e.g., 2 to 6 rings, etc.) aromatic ring is an aromatic ring having a plurality of (e.g., 2 to 6, etc.) condensed aromatic ring structures as a ring structure. The number of ring members in the aromatic ring is preferably 5 to 15. The aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring. When the aromatic ring is an aromatic heterocyclic ring, the number of heteroatoms contained as ring member atoms is, for example, 1 to 10. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, and a fluorene ring.Examples of the aromatic heterocycle include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring (e.g., a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring), a tetrazine ring (e.g., a 1,2,4,5-tetrazine ring), a quinoxaline ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a naphthopyrrole ring, a naphthofuran ring, a naphthothiophene ring, a naphthoimidazole ring, a naphthoxazole ring, a pyrroloimidazole ring (e.g., a 5H-pyrrolo[1,2-a]imidazole ring), an imidazooxazole ring (e.g., an imidazo[2,1-b]oxazole ring), Thienothiazole rings (for example, thieno[2,3-d]thiazole rings, etc.), benzothiadiazole rings, benzodithiophene rings (for example, benzo[1,2-b:4,5-b']dithiophene rings, etc.), thienothiophene rings (for example, thieno[3,2-b]thiophene rings, etc.), thiazolothiazole rings (for example, thiazolo[5,4-d]thiazole rings, etc.), naphthodithiophene rings (for example, naphtho[2,3 [2,1-b:6,7-b']dithiophene ring, naphtho[2,1-b:6,5-b']dithiophene ring, naphtho[1,2-b:5,6-b']dithiophene ring, 1,8-dithiadicyclopenta[b,g]naphthalene ring, etc.), benzothienobenzothiophene ring, dithieno[3,2-b:2',3'-d]thiophene ring, and 3,4,7,8-tetrathiadicyclopenta[a,e]pentalene ring.

[0020] As used herein, the term "aromatic ring group" includes, for example, a group obtained by removing one or more hydrogen atoms (e.g., 1 to 5) from the above-mentioned aromatic ring. As used herein, the term "aryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic hydrocarbon ring among the above-mentioned aromatic rings. As used herein, the term "heteroaryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings. As used herein, the term "arylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above-mentioned aromatic rings. As used herein, the term "heteroarylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings. In the optionally substituted aromatic ring, optionally substituted aromatic ring group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted arylene group, and optionally substituted heteroarylene group, the types of substituents that these may have include, for example, the groups exemplified for the substituent W. When these groups which may have a substituent have a substituent, the number of the substituents may be one or more (for example, 1 to 4, etc.).

[0021] As used herein, the term "non-aromatic ring" refers to a ring structure that is not aromatic, and examples thereof include an aliphatic hydrocarbon ring and an aliphatic heterocycle. Examples of the aliphatic hydrocarbon ring include cycloalkane, cycloalkene, and cycloalkyne. As used herein, the term "aliphatic heterocyclic group" refers to, for example, a group obtained by removing one hydrogen atom from the aliphatic heterocycle. As used herein, the number of ring members in the aliphatic heterocyclic group is preferably 5 to 20, more preferably 5 to 12, and even more preferably 6 to 8. Examples of heteroatoms contained in the aliphatic heterocyclic group include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, with a sulfur atom, an oxygen atom, or a nitrogen atom being preferred. Examples of the aliphatic heterocycle constituting the aliphatic heterocyclic group include a pyrrolidine ring, an oxolane ring (tetrahydrofuran ring), a thiolane ring, a piperidine ring, a tetrahydropyran ring, a thiane ring (pentamethylene sulfide ring), a piperazine ring, a morpholine ring, a quinuclidine ring, an azetidine ring, an oxetane ring, an aziridine ring, a dioxane ring, and a γ-butyrolactone ring.

[0022] [Photoelectric conversion element] The photoelectric conversion element of the present invention is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film contains a compound represented by formula (1) (hereinafter also referred to as a "specific compound").

[0023] Although the reason why the photoelectric conversion element having the above configuration can solve the problem of the present invention is not entirely clear, the inventors speculate as follows. Note that the following speculation does not limit the mechanism by which the effect is obtained. In other words, even if the effect is obtained by a mechanism other than the one described below, it is still included in the scope of the present invention. The specific compound is a so-called donor-acceptor type compound having a donor moiety and an acceptor moiety. The photoelectric conversion element of the present invention has excellent sensitivity to blue-green light, which is the problem of the present invention, because the specific compound has the characteristics described below. It is believed that in the photoelectric conversion film, the specific compound absorbs light, generates excitons, and then undergoes charge separation, resulting in the generation of holes and electrons. Light is converted into electricity by the transport of the holes and electrons, but if the specific compound aggregates at this time, charge separation becomes less likely to occur. Therefore, it is believed that the specific compound can achieve high sensitivity due to its strong light absorption (generating more excitons) and reduced intermolecular aggregation. More specifically, the specific compound is a compound having a structure such as B １ The structure shown by R Ｚ１ and R Ｚ２ It is presumed that the problem of the present invention has been solved by specifying at least one of the substituents represented by the formula (I) to a structure selected from the substituent group S, thereby forming a structure that suppresses aggregation of the specific compounds. Hereinafter, superior sensitivity to blue-green light is also referred to as "superior effect of the present invention."

[0024] FIG. 1 shows a cross-sectional schematic diagram of one embodiment of the photoelectric conversion element of the present invention. The photoelectric conversion element 10a shown in FIG. 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 functioning as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and a transparent conductive film (hereinafter also referred to as the "upper electrode") 15 functioning as an upper electrode are stacked in this order. FIG. 2 shows an example of the configuration of another photoelectric conversion element. The photoelectric conversion element 10b shown in FIG. 2 has a configuration in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are stacked in this order on a lower electrode 11. Note that the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in FIGS. 1 and 2 may be changed as appropriate depending on the application and characteristics.

[0025] In the photoelectric conversion element 10a (or 10b), it is preferable that light is incident on the photoelectric conversion film 12 through the upper electrode 15. When the photoelectric conversion element 10a (or 10b) is used, a voltage can be applied. In this case, the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and a voltage of 1×10 is applied between the pair of electrodes. －５ ~1 x 10 ７ In terms of performance and power consumption, it is preferable to apply a voltage of 1×10 V / cm. －４ ~1 x 10 ７ V / cm is more preferable, and 1×10 －３ ~5 x 10 ６ V / cm is more preferable. Regarding the voltage application method, it is preferable to apply the voltage so that the electron blocking film 16A side serves as the cathode and the photoelectric conversion film 12 side serves as the anode in FIGS. 1 and 2. When the photoelectric conversion element 10a (or 10b) is used as a photosensor or incorporated into an imaging element, a voltage can be applied in a similar manner. As will be described in detail later, the photoelectric conversion element 10a (or 10b) can be suitably used as an imaging element. The configuration of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.

[0026] [Photoelectric Conversion Film] The photoelectric conversion element has a photoelectric conversion film.

[0027] <Specific Compound> The photoelectric conversion film contains a compound (specific compound) represented by formula (1).

[0028]

[0029] In formula (1), R １ represents a hydrogen atom or a substituent. １ represents a sulfur atom, an oxygen atom, or a selenium atom. １ and Z ２ one of which represents a sulfur atom, an oxygen atom, or a selenium atom, and the other represents -CR Ｚ２ = represents. R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a substituent. Ｚ１ and R Ｚ２ At least one of the groups represents a group selected from the group S of substituents. The group S of substituents includes an aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, and —Si(R Ｓｉ１ ) ３ .R Ｓｉ１ represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. １ represents a group represented by formula (A-1) or formula (A-2). １ is a group represented by any one of formulas (B1) to (B12). The groups represented by formula (A-1), formula (A-2), and formula (B1) to formula (B12) will be described in detail later.

[0030] The groups or structures represented by the symbols in formula (1) are explained below. １ represents a hydrogen atom or a substituent. １ Examples of the substituent represented by R include the groups exemplified as the substituent W. １ is preferably a hydrogen atom. １ represents a sulfur atom, an oxygen atom, or a selenium atom. １ is preferably a sulfur atom or an oxygen atom, more preferably a sulfur atom. １ and Z ２one of which represents a sulfur atom, an oxygen atom, or a selenium atom, and the other represents -CR Ｚ２ = represents Z １ and Z ２ As for Z, １ is a sulfur atom or an oxygen atom, and Z ２ Ga-CR Ｚ２ Preferably, Z １ is a sulfur atom, and Z ２ Ga-CR Ｚ２ It is more preferable that R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a substituent. Ｚ１ and R Ｚ２ At least one of R represents a group selected from the substituent group S. Examples of the substituent include the groups exemplified as the substituent W above. Ｚ１ and R Ｚ２ It is preferred that one of R represents a hydrogen atom and the other represents a group selected from the substituent group S; Ｚ１ and R Ｚ２ and R preferably represent a group selected from the substituent group S. Ｚ１ and R Ｚ２ It is preferred that the substituent represented by the formula (A-1) does not have either a group represented by the formula (A-2) described later or a group represented by the formula (A-1) described later.

[0031] Groups Selected from Substituent Group S Groups selected from the above-mentioned Substituent Group S are shown below. Substituent Group S: An aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, and —Si(R Ｓｉ１ ) ３ .

[0032] Among the groups selected from the substituent group S, R Ｚ１ and R Ｚ２ At least one of R is preferably an aromatic ring group which may have a substituent, or an aliphatic hydrocarbon group which may have a substituent, Ｚ１ and R Ｚ２ It is more preferable that at least one of R is an aromatic ring group which may have a substituent, Ｚ１and R Ｚ２ and (b) are each an aromatic ring group which may have a substituent. In the substituent group S, examples of the substituent which the aromatic ring group, the aliphatic hydrocarbon group, the aliphatic heterocyclic group, and the acyl group may have include the groups exemplified as the substituent W. Hereinafter, specific embodiments and preferred embodiments of the groups selected from the substituent group S will be described in detail.

[0033] The aromatic ring group in the aromatic ring group which may have a substituent may be either an aromatic hydrocarbon group or an aromatic heterocyclic group, with an aromatic hydrocarbon group being preferred. The aromatic ring group may be either a monocyclic or polycyclic ring. The number of ring members in the aromatic ring group is preferably 5 to 15, more preferably 5 to 10, and even more preferably 5 to 6. The number of carbon atoms in the aromatic ring group (the number of carbon atoms including the carbon atoms in the substituent) is preferably 1 to 30, more preferably 3 to 20, and even more preferably 4 to 10. Examples of heteroatoms contained in the aromatic heterocyclic group include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, with a sulfur atom, an oxygen atom, or a nitrogen atom being preferred. Specific examples of the aromatic ring group are as described above, and are preferably a phenyl group, a naphthyl group, a thiophene ring group, a furan ring group, a thiazole ring group, an oxazole ring group, a benzofuran ring group, a pyridine ring group, or a pyrimidine ring group, more preferably a phenyl group or a thiophene ring group, and even more preferably a phenyl group. The aromatic ring group preferably has a substituent. The number of substituents that the aromatic ring group may have is preferably 1 to 6, more preferably 1 to 3. The aromatic ring group that may have a substituent is preferably a group represented by formula (S1), and more preferably a group represented by formula (S2).

[0034]

[0035] In formula (S1), C ｍrepresents a monocyclic aromatic ring which may have a substituent. The monocyclic aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, and is preferably an aromatic hydrocarbon ring. Specific examples of the aromatic hydrocarbon ring and the aromatic heterocycle are as described above. Examples of the substituent which the aromatic ring may have include the groups exemplified for the substituent W described above, and among these, a group selected from the substituent group T described below is preferred. As the monocyclic aromatic ring which may have a substituent, a benzene ring which may have a substituent is preferred, and a benzene ring which may have a group selected from the substituent group T is more preferred.

[0036] In formulas (S1) and (S2), Rs represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, a halogen atom, a cyano group, or —Si(R Ｓｉ２ ) ３ Represents R Ｓｉ２ represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent.

[0037] Examples of the substituent that the aliphatic hydrocarbon group, aromatic cyclic group, and aliphatic heterocyclic group may have include the groups exemplified for the substituent W. The definition and preferred embodiments of the aliphatic hydrocarbon group are as described above. The aliphatic hydrocarbon group represented by Rs may have at least one of an ethereal oxygen atom (—O—) and a thioethereal sulfur atom (—S—). As the aliphatic hydrocarbon group represented by Rs, a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms is preferred, and a linear alkyl group having 1 to 2 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms is more preferred. The definition and preferred embodiments of the aromatic cyclic group are as described above. As the aromatic cyclic group represented by Rs, a phenyl group is preferred. The definition and preferred embodiments of the aliphatic heterocyclic group are as described above. As the halogen atom, a fluorine atom or a chlorine atom is preferred.

[0038] R Ｓｉ２The definitions of the optionally substituted aliphatic hydrocarbon group, the optionally substituted aromatic ring group, and the optionally substituted aliphatic heterocyclic group represented by Rs are as described above, and preferred embodiments are the same as the optionally substituted aliphatic hydrocarbon group, the optionally substituted aromatic ring group, and the optionally substituted aliphatic heterocyclic group represented by Rs. Ｓｉ２ The aliphatic hydrocarbon group represented by the formula (I) may have at least one of an etheric oxygen atom and a thioetheric sulfur atom.

[0039] Rs may be, among others, an alkyl group, an alkoxy group, a halogen atom, -Si(R Ｓｉ２ ) ３ , cyano group, alkylthio group, aryl group, heteroaryl group, alkenyl group, or alkynyl group (hereinafter, these groups are also collectively referred to as "substituent group T") are preferred, alkyl group, alkoxy group, or halogen atom are more preferred, and alkyl group is even more preferred. The alkyl group, alkenyl group, alkynyl group, alkoxy group, and alkylthio group may have a halogen atom. The aryl group and heteroaryl group may have a halogen atom or alkyl group (preferably an alkyl group having 1 to 4 carbon atoms).

[0040] In the substituent group T, the alkyl group, alkoxy group, alkylthio group, alkenyl group, and alkynyl group preferably have 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms. The aryl group and heteroaryl group preferably have 4 to 10 carbon atoms (including the number of carbon atoms in the substituents). As the alkyl group, a linear or branched alkyl group is preferable, a linear or branched alkyl group having 1 to 5 carbon atoms is more preferable, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a tert-butyl group is even more preferable, and a methyl group or an isopropyl group is particularly preferable. As the alkoxy group, an alkoxy group having 1 to 3 carbon atoms is preferable, and a methoxy group is more preferable.

[0041] In formulas (S1) and (S2), C ｍThe substituents that R may have and Rs may be bonded to each other to form one or more non-aromatic rings. Specific examples of the non-aromatic ring are as described above, but among them, an aliphatic hydrocarbon ring is preferable, a cycloalkane or cycloalkene is more preferable, and a 5- or 6-membered cycloalkane or cycloalkene is even more preferable.

[0042] In the substituent group S, examples of the aliphatic hydrocarbon group in the aliphatic hydrocarbon group which may have a substituent include a straight-chain aliphatic hydrocarbon group, a branched-chain aliphatic hydrocarbon group, and a cyclic aliphatic hydrocarbon group. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 20. The number of carbon atoms in the straight-chain aliphatic hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3. The number of carbon atoms in the branched-chain aliphatic hydrocarbon group is preferably 3 to 20, more preferably 3 to 7, and even more preferably 3 to 5. The cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic, but is preferably monocyclic. The number of carbon atoms in the cyclic aliphatic hydrocarbon group is preferably 3 to 20, more preferably 3 to 8, and even more preferably 3 to 6.

[0043] The number of ring members in the aliphatic heterocyclic group which may have a substituent is preferably 5 to 20, more preferably 5 to 12, and still more preferably 5 to 8. The number of carbon atoms in the aliphatic heterocyclic group is preferably 1 to 20. Examples of heteroatoms contained in the aliphatic heterocyclic group include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, an oxygen atom, or a nitrogen atom is preferred.

[0044] In the substituent group S, the acyl group preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 5 carbon atoms.

[0045] -Si(R Ｓｉ１ ) ３ In this case, R Ｓｉ１ represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Examples of the substituent which the aliphatic hydrocarbon group, aromatic ring group, and aliphatic heterocyclic group may have include the groups exemplified for the substituent W. Ｓｉ１The optionally substituted aliphatic hydrocarbon group, the optionally substituted aromatic ring group, and the optionally substituted aliphatic heterocyclic group represented by the following formula (I) have the same meaning as the optionally substituted aliphatic hydrocarbon group, the optionally substituted aromatic ring group, and the optionally substituted aliphatic heterocyclic group in the substituent group S. Ｓｉ１ Among these, an aliphatic hydrocarbon group is preferable, and an alkyl group having 1 to 4 carbon atoms is more preferable.

[0046] The compound represented by formula (1) (specific compound) is preferably a compound represented by formula (2).

[0047]

[0048] In formula (2), R １ , X １ , A １ and B １ is R in formula (1). １ , X １ , A １ and B １ The preferred embodiments are the same as those described in detail for formula (1). １ and B １ This will be explained in detail later. １１ represents a sulfur atom, an oxygen atom, or a selenium atom, preferably a sulfur atom or an oxygen atom, and more preferably a sulfur atom. Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a group selected from the above-mentioned substituent group S. Ｚ１ and R Ｚ２ At least one of R represents an aromatic ring group which may have a substituent. Ｚ１ and R Ｚ２ Preferably, one of R represents an aromatic ring group which may have a substituent, and the other represents a hydrogen atom or a group selected from the substituent group S; Ｚ１ and R Ｚ２and (B) represent an aromatic ring group which may have a substituent. The definitions and preferred embodiments of the groups selected from the substituent group S are as described above. In particular, in formula (2), the aromatic ring group which may have a substituent is preferably a group represented by the above formula (S1), and more preferably a group represented by the above formula (S2).

[0049] A group represented by any one of formulas (B1) to (B12) As described above, in formula (1) and formula (2), B １ is represented by any one of formulas (B1) to (B12). １ is preferably a group represented by any one of formulas (B1-1), (B2-1), (B3-1), (B4-1) to (B4-3), (B5-1) to (B5-3), and (B6). These formulas are described in detail below.

[0050]

[0051] In formula (B1), Ar １ represents an aromatic ring group which may have a substituent. ２ and R ３ each independently represents a hydrogen atom or a substituent. ２ represents an aromatic ring group which may have a substituent.

[0052] Ar １ and an aromatic ring group represented by Ar ２ The aromatic ring group represented by Ar may be either a monocyclic or polycyclic group, but is preferably a monocyclic aromatic ring group. １ and an aromatic ring group represented by Ar ２ The number of ring members of the aromatic ring group represented by Ar is preferably 5 to 15, more preferably 5 to 10, and even more preferably 5 to 6. １ and an aromatic ring group represented by Ar ２ The number of carbon atoms in the aromatic ring group represented by the formula (the number of carbon atoms including the carbon atoms in the substituent) is preferably 1 to 30, more preferably 3 to 20, and even more preferably 4 to 10. １ and an aromatic ring group represented by Ar ２The aromatic ring group represented by the formula (I) may be either an aromatic hydrocarbon group or an aromatic heterocyclic group, but is preferably an aromatic hydrocarbon group. Examples of heteroatoms contained in the aromatic heterocyclic group include sulfur atom, oxygen atom, nitrogen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom, and boron atom, and sulfur atom, oxygen atom, or nitrogen atom is preferred. Specific examples of the aromatic ring group are as described above, and are preferably a phenyl group, a naphthyl group, a thiophene ring group, a furan ring group, a benzothiophene ring group, a benzofuran ring group, a benzothiazole ring group, a benzoxazole ring group, or a pyrimidine ring group, more preferably a phenyl group, a pyrimidine ring group, or a thiophene ring group, and even more preferably a phenyl group.

[0053] The group represented by formula (B1) is preferably a group represented by formula (B1-1), and the group represented by formula (B2) is preferably a group represented by formula (B2-1).

[0054] In formula (B1-1), Ar １１ represents a monocyclic aromatic ring group which may have a substituent. ２ and R ３ is R in the above formula (B1). ２ and R ３ In formula (B2-1), Ar １２ represents a monocyclic aromatic ring group which may have a substituent.

[0055] In the above formula (B3) and formula (B10), C ２ represents an aromatic ring which may have a substituent. The definition and preferred embodiments of the aromatic ring are as described above. ２ Among these, the aromatic ring represented by the formula (I) is preferably a benzene ring which may have a substituent, a thiophene ring which may have a substituent, or a furan ring which may have a substituent.

[0056] In formula (B3) and formula (B10), V １ is -C(R Ｃ１ ) (R Ｃ２ )-. Ｃ１ and R Ｃ２ R each independently represents a hydrogen atom or a substituent. Ｃ１ and R Ｃ２may be bonded to each other to form a ring. Examples of the substituent include the groups exemplified for the substituent W described above, and among these, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent is preferred. The definitions and preferred embodiments of the aliphatic hydrocarbon group which may have a substituent, the aromatic ring group which may have a substituent, and the aliphatic heterocyclic group which may have a substituent are the same as those of the aliphatic hydrocarbon group which may have a substituent, the aromatic ring group which may have a substituent, and the aliphatic heterocyclic group which may have a substituent in the substituent group S.

[0057] In formula (B3) and formula (B10), n represents an integer of 0 to 4, preferably 1. １ is -CR Ｃ３ = or a nitrogen atom, -CR Ｃ３ = is preferred. Ｃ３ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom, and still more preferably a hydrogen atom.

[0058] The group represented by formula (B3) is preferably a group represented by formula (B3-1).

[0059]

[0060] In formula (B3-1), R Ｂ１ and R Ｂ２ R each independently represents a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ｂ１ and R Ｂ２ may be bonded to each other to form a ring. Preferred embodiments of the optionally substituted aliphatic hydrocarbon group, the optionally substituted aromatic ring group, and the optionally substituted aliphatic heterocyclic group include preferred embodiments of the optionally substituted aliphatic hydrocarbon group, the optionally substituted aromatic ring group, and the optionally substituted aliphatic heterocyclic group selected from the above-mentioned substituent group S. Ｂ１ and R Ｂ２Among these, an aliphatic hydrocarbon group which may have a substituent is preferred.

[0061] In formula (B3-1), Q １ is -CR Ｃ３ = or represents a nitrogen atom. Ｃ３ is R in the above formula (B3). Ｃ３ It is synonymous with: ３０ ~Q ３３ are each independently -CR Ｃ３ '= or a nitrogen atom. Ｃ３ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom.

[0062] In the above formula (B4) and formula (B11), C ３ represents an aromatic ring or a non-aromatic ring in which at least one ring atom is substituted with >C=M. ３ The aromatic ring and the non-aromatic ring represented by the formula (I) may have a substituent. Examples of the substituent include the substituents exemplified for the substituent W, and preferred are an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, or a cyano group. However, C ３ The substituents that may be possessed by the aromatic ring and non-aromatic ring represented by the formula (A-2) described below do not have a group represented by the formula (A-2). The definition and preferred embodiments of the aromatic ring are as described above. ３ Among these, the aromatic ring represented by the formula (I) is preferably a benzene ring which may have a substituent, a thiophene ring which may have a substituent, or a furan ring which may have a substituent.

[0063] The non-aromatic ring in which at least one ring atom is substituted with >C=M refers to ring structures such as cyclic esters and cyclic amides. M is an oxygen atom, a sulfur atom, or ═NR Ｍ１ or =CR Ｍ２ R Ｍ３ M is preferably an oxygen atom or a sulfur atom. Ｍ１ represents a hydrogen atom or a substituent. Examples of the substituent include the substituents exemplified above for the substituent W.Ｍ２ and R Ｍ３ each independently represents a cyano group, —SO ２ R Ｍ４ , -COOR Ｍ５ or -COR Ｍ６ Represents R Ｍ４ ~R Ｍ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. As the non-aromatic ring in which at least one ring atom is substituted with >C=M, a cyclic imide, a cyclic 1,3-diketone, or a cyclic carbonate is preferred, and a cyclic imide, a cyclic 1,3-diketone, or a cyclic carbonate having 5 or 6 ring atoms is more preferred.

[0064] In formula (B4) and formula (B11), V ２ represents a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom, and a sulfur atom or an oxygen atom is preferred. Ｎ represents a hydrogen atom or a substituent. Ｎ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W described above, and an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, and an aliphatic heterocyclic group which may have a substituent are preferred. Preferred embodiments of the aliphatic hydrocarbon group which may have a substituent, the aromatic ring group which may have a substituent, and the aliphatic heterocyclic group which may have a substituent are preferred embodiments of the aliphatic hydrocarbon group which may have a substituent, the aromatic ring group which may have a substituent, and the aliphatic heterocyclic group which may have a substituent selected from the above substituent group S. Q ２ is -CR Ｃ４ = or a nitrogen atom, -CR Ｃ４ = is preferred. Ｃ４ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom, and still more preferably a hydrogen atom.

[0065] The group represented by formula (B4) is preferably a group represented by any one of formulas (B4-1) to (B4-3).

[0066]

[0067] In formula (B4-1), V ２ is V in the above formula (B4). ２ It is synonymous with: ２ are each independently -CR Ｃ４ = or represents a nitrogen atom. Ｃ４ is R in the above formula (B4). Ｃ４ It is synonymous with: ４０ ~Q ４３ are each independently -CR Ｃ４ '= or a nitrogen atom. Ｃ４ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom.

[0068] In formula (B4-2), V ２ and V ４ are each independently a sulfur atom, an oxygen atom, or —NR Ｎ - or a selenium atom, and a sulfur atom or an oxygen atom is preferred. Ｎ The definition and preferred embodiments of Q are as described above. ２ is -CR Ｃ４ = or represents a nitrogen atom. Ｃ４ is R in the above formula (B4). Ｃ４ It is synonymous with: ４４ ~Q ４５ are each independently -CR Ｃ４ '= or a nitrogen atom. Ｃ４ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom.

[0069] In formula (B4-3), V ２ and Q ２ is V in the above formula (B4).２ and Q ２ It is synonymous with X. ｂ１ and X ｂ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｘ１ or =CR Ｘ２ R Ｘ３ R represents an oxygen atom. Ｘ１ represents a hydrogen atom or a substituent. Ｘ２ and R Ｘ３ each independently represents a cyano group, —SO ２ R Ｘ４ , -COOR Ｘ５ or -COR Ｘ６ Represents R Ｘ４ ~R Ｘ６ X each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ３ is -NR Ｎ -, -C(R Ｂ３ ) (R Ｂ４ ) represents -, an oxygen atom or a sulfur atom, -NR Ｎ -, or -C(R Ｂ３ ) (R Ｂ４ )- is preferred. Ｎ The definition and preferred embodiments of R are as described above. Ｂ３ and R Ｂ４ each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified for the substituent W described above, and among these, an aliphatic hydrocarbon group which may have a substituent is preferred. The definition and preferred embodiments of the aliphatic hydrocarbon group which may have a substituent are the same as those of the aliphatic hydrocarbon group which may have a substituent in the substituent group S.

[0070] In formula (B5) and formula (B12), C ４ represents an aromatic ring or a non-aromatic ring in which at least one ring atom is substituted with >C=M. ４ Preferred embodiments of the aromatic ring and non-aromatic ring represented by C ３ The same applies to the aromatic ring and non-aromatic ring represented by the formula:

[0071] In formula (B5), Q ３ and Q ５ are each independently -CRＣ５ = or a nitrogen atom, -CR Ｃ５ = is preferred. Ｃ５ represents a hydrogen atom or a substituent, and a hydrogen atom is preferred. ４ is -CR Ｃ５ '= or a nitrogen atom. Ｃ５ represents a hydrogen atom or a substituent, and is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom. ５ is -CR Ｃ５ = or a nitrogen atom, -CR Ｃ５ = is preferred. Ｃ５ represents a hydrogen atom or a substituent, and a hydrogen atom is preferred. ３ and Q ４ is -CR Ｃ５ '= or a nitrogen atom. Ｃ５ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom.

[0072] The group represented by formula (B5) is preferably a group represented by any one of formulas (B5-1) to (B5-3).

[0073]

[0074] In formula (B5-1), Q ３ and Q ５ are each independently -CR Ｃ５ = or represents a nitrogen atom. Ｃ５ is R in the above formula (B5). Ｃ５ It is synonymous with: ４ and Q ５０ ~Q ５３ is -CR Ｃ５ '= or a nitrogen atom. Ｃ５ ' is R in the above formula (B5). Ｃ５ ' is synonymous with '.

[0075] In formula (B5-2), Q ３ and Q５ are each independently -CR Ｃ５ = or a nitrogen atom. Ｃ５ is R in the above formula (B5). Ｃ５ It is synonymous with: ４ and Q ５４ is -CR Ｃ５ '= or a nitrogen atom. Ｃ５ ' is R in the above formula (B5). Ｃ５ ' is synonymous with Z. ３ and Z ４ one of which is a sulfur atom, an oxygen atom, or —NR Ｎ - or a selenium atom, and the other is -CR Ｃ５ '= or a nitrogen atom. Z ３ is a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom; Z ４ Ga-CR Ｃ５ preferably represents a nitrogen atom, and Z ３ represents a sulfur atom or an oxygen atom, Z ４ Ga-CR Ｃ５ It is more preferable to represent '='.

[0076] In formula (B5-3), Q ３ ~Q ５ is Q in the above formula (B5) ３ ~Q ５ It is synonymous with X. ｂ４ and X ｂ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｘ１ or =CR Ｘ２ R Ｘ３ R represents an oxygen atom. Ｘ１ represents a hydrogen atom or a substituent. Ｘ２ and R Ｘ３ each independently represents a cyano group, —SO ２ R Ｘ４ , -COOR Ｘ５ or -COR Ｘ６ Represents R Ｘ４ ~R Ｘ６ X each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ６ is -NRＮ -, -C(R Ｂ５ ) (R Ｂ６ ) represents -, an oxygen atom or a sulfur atom, -NR Ｎ -, or -C(R Ｂ５ ) (R Ｂ６ )- is preferred. Ｎ The definition and preferred embodiments of R are as described above. Ｂ５ and R Ｂ６ each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified for the substituent W described above, and among these, an aliphatic hydrocarbon group which may have a substituent is preferred. The definition and preferred embodiments of the aliphatic hydrocarbon group which may have a substituent are the same as those of the aliphatic hydrocarbon group which may have a substituent in the substituent group S.

[0077] In formula (B6), Q ６ and Q １２ are each independently -CR Ｃ６ = or a nitrogen atom, -CR Ｃ６ It is preferable that R Ｃ６ represents a hydrogen atom or a substituent, and is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom, and even more preferably a hydrogen atom. ７ ~Q １１ are each independently -CR Ｃ６ '= or a nitrogen atom. Ｃ６ represents a hydrogen atom or a substituent, preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom.

[0078] In formula (B7), V ３ represents a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom, and a sulfur atom or an oxygen atom is preferred. Ｎ The definition and preferred embodiments of Q are as described above. １３ is -CR Ｃ７ = or a nitrogen atom, -CR Ｃ７It is preferable that R Ｃ７ represents a hydrogen atom or a substituent, and is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom, and even more preferably a hydrogen atom. １４ and Q １５ are each independently -CR Ｃ７ '= or a nitrogen atom. Ｃ７ Q′ represents a hydrogen atom or a substituent, and is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom. １６ and Q ２０ are each independently -CR Ｃ８ = or a nitrogen atom, -CR Ｃ８ It is preferable that R Ｃ８ represents a hydrogen atom or a substituent, and is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom, and even more preferably a hydrogen atom. １７ ~Q １９ are each independently -CR Ｃ８ '= or a nitrogen atom. Ｃ８ represents a hydrogen atom or a substituent, and is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom. Ｃ８ The substituent represented by ' does not have either a group represented by formula (A-1) described below or a group represented by formula (A-2) described below.

[0079] In formula (B9), W ５ and W ６ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ Represents R Ｗ１ ~RＷ３ represents R in formula (A-1) described below. Ｗ１ ~R Ｗ３ It is synonymous with W. ５ and W ６ are each independently preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom. ４ is -NR Ｎ -, or -C(R Ｃ１ ) (R Ｃ２ )-. V ４ As the Ｎ - is preferred. Ｎ The definition and preferred embodiments of R are as described above. Ｃ１ and R Ｃ２ each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified for the substituent W described above, and among these, an aromatic ring group which may have a substituent or an aliphatic hydrocarbon group which may have a substituent is preferred, and an aliphatic hydrocarbon group which may have a substituent is more preferred. The definitions and preferred embodiments of the aromatic ring group which may have a substituent and the aliphatic hydrocarbon group which may have a substituent are the same as those of the aromatic ring group which may have a substituent and the aliphatic hydrocarbon group which may have a substituent in the substituent group S. Q ２１ is -CR Ｃ９ = or a nitrogen atom, -CR Ｃ９ = is preferred. Ｃ９ represents a hydrogen atom or a substituent, R Ｃ９ The substituent represented by the formula (A-1) does not have a group represented by the formula (A-1) described below. Ｃ９ is preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, an alkoxy group, a halogen atom, or a cyano group, more preferably a hydrogen atom, an aliphatic hydrocarbon group which may have a halogen atom, an alkoxy group, a halogen atom, or a cyano group, and more preferably a hydrogen atom, an aliphatic hydrocarbon group, an alkoxy group, or a halogen atom.

[0080] It is preferable that the groups represented by formulae (B1) to (B12) do not each have a group represented by formula (A-1) or a group represented by formula (A-2) described below.

[0081] A group represented by formula (A-1) or formula (A-2) In formula (1) and formula (2), A １ represents a group represented by formula (A-1) or formula (A-2). The group represented by formula (A-1) or formula (A-2) will be described in detail below.

[0082]

[0083] In formula (A-1), C １ represents a ring containing two or more carbon atoms which may have a substituent. １ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ Represents R Ｗ１ represents a hydrogen atom or a substituent. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ or -COR Ｗ６ Represents R Ｗ４ ~R Ｗ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ａ１ and R ａ２ each independently represents a cyano group, —COOR ｂ１ , -COR ｂ２ , -SOR ｂ３ , or -SO ２ R ｂ４ Represents R ｂ１ ~R ｂ４ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent.

[0084] In formula (A-1), C １ represents a ring containing two or more carbon atoms and which may have a substituent. １The two carbon atoms contained in are the two carbon atoms specified in formula (A-1). The number of carbon atoms in the ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10. The number of carbon atoms in the ring is the number including the two carbon atoms specified in the formula. The ring may be either an aromatic ring or a non-aromatic ring. The ring may be either a monocyclic or polycyclic ring, and is preferably a 5-membered ring, a 6-membered ring, or a fused ring containing at least one of a 5-membered ring and a 6-membered ring. The number of carbon atoms in the fused ring containing at least one of a 5-membered ring and a 6-membered ring is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 10.

[0085] The ring may have a heteroatom. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, a nitrogen atom, or an oxygen atom is preferred. The number of heteroatoms in the ring is preferably 0 to 10, and more preferably 0 to 5. １ Among the carbon atoms constituting the ring represented by the formula (A-1), the carbon atom at the bonding position marked with * and W １ Carbon atoms other than the carbon atom bonded to may be substituted with a carbonyl carbon (>C=O) or a thiocarbonyl carbon (>C=S).

[0086] Above C １The ring represented by the formula (I) is preferably a ring used as an acidic nucleus (for example, the acidic nucleus in a merocyanine dye), and examples thereof include the following nuclei: (a) 1,3-dicarbonyl nucleus: for example, a 1,3-indandione nucleus, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, and 1,3-dioxane-4,6-dione; (b) pyrazolinone nucleus: for example, 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, and 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one; (c) isoxazolinone nucleus: for example, 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one; (d) oxindole nucleus: for example, 1-alkyl-2,3-dihydro-2-oxindole; (e) 2,4,6-trioxohexahydropyrimidine nucleus: for example, barbituric acid, 2-thiobarbituric acid, and derivatives thereof. Examples of the derivatives include 1-alkyl compounds such as 1-methyl and 1-ethyl, 1,3-dialkyl compounds such as 1,3-dimethyl, 1,3-diethyl, and 1,3-dibutyl, 1,3-diaryl compounds such as 1,3-diphenyl, 1,3-di(p-chlorophenyl), and 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1-aryl compounds such as 1-ethyl-3-phenyl, and 1,3-diheteroaryl compounds such as 1,3-di(2-pyridyl). (f) 2-thio-2,4-thiazolidinedione nucleus: for example, rhodanine and derivatives thereof. Examples of the derivatives include 3-alkylrhodanines such as 3-methylrhodanine, 3-ethylrhodanine, and 3-allylrhodanine, 3-arylrhodanines such as 3-phenylrhodanine, and 3-heteroarylrhodanines such as 3-(2-pyridyl)rhodanine. (g) 2-thio-2,4-oxazolidinedione nucleus (2-thio-2,4-(3H,5H)-oxazoledione nucleus): for example, 3-ethyl-2-thio-2,4-oxazolidinedione. (h) thianaphthenone nucleus: for example, 3(2H)-thianaphthenone-1,1-dioxide. (i) 2-thio-2,5-thiazolidinedione nucleus: for example, 3-ethyl-2-thio-2,5-thiazolidinedione.(j) 2,4-thiazolidinedione nucleus: for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione. (k) thiazolin-4-one nucleus: for example, 4-thiazolinone and 2-ethyl-4-thiazolinone. (l) 2,4-imidazolidinedione (hydantoin) nucleus: for example, 2,4-imidazolidinedione and 3-ethyl-2,4-imidazolidinedione. (m) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus: for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidinedione. (n) Imidazolin-5-one nucleus: for example, 2-propylmercapto-2-imidazolin-5-one, etc. (o) 3,5-pyrazolidinedione nucleus: for example, 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione, etc. (p) Benzothiophen-3(2H)-one nucleus: for example, benzothiophen-3(2H)-one, oxobenzothiophen-3(2H)-one, and dioxobenzothiophen-3(2H)-one, etc. (q) Indanone nucleus: for example, 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone, and 3,3-dimethyl-1-indanone, etc. (r) Benzofuran-3-(2H)-one nucleus: for example, benzofuran-3-(2H)-one, etc. (s) 2,2-dihydrophenalene-1,3-dione nucleus, etc.

[0087] In formula (A-1), W １ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ Represents W. １ is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom, in that the effects of the present invention are more excellent. Ｗ１ represents a hydrogen atom or a substituent. Examples of the substituent include the substituents exemplified above for the substituent W. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ or -CORＷ６ Represents R Ｗ４ ~R Ｗ６ R each independently represent an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. The definition of the aliphatic hydrocarbon group is as described above, and an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred. The definition of the aromatic ring group is as described above, and an aromatic hydrocarbon group is preferred, and a phenyl group is more preferred. The definition of the aliphatic heterocyclic group is as described above, and the heteroatom contained in the aliphatic heterocyclic group is preferably an oxygen atom, a sulfur atom, or a nitrogen atom. R Ｗ４ ~R Ｗ６ Examples of the substituent that each group represented by the following formula may have include the substituents exemplified for the substituent W above.

[0088] In formula (A-2), R ａ１ and R ａ２ each independently represents a cyano group, —COOR ｂ１ , -COR ｂ２ , -SOR ｂ３ , or -SO ２ R ｂ４ represents a cyano group or —COR ｂ４ is preferred. ｂ１ ~R ｂ４ R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ１ ~R ｂ４ The definitions and preferred embodiments of each group represented by R Ｗ４ ~R Ｗ６ Among these, an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a phenyl group is preferred.

[0089] The group represented by the formula (A-1) is preferably a group represented by the formula (A-3) or (A-4) in terms of achieving better effects of the present invention.

[0090]

[0091] In formula (A-3), C ５ represents a ring containing 3 or more carbon atoms which may have a substituent.２ and W ３ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ In formula (A-4), C ６ represents a ring containing 3 or more carbon atoms which may have a substituent. ４ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ Represents R ｄ１ represents a hydrogen atom or a substituent. Ｗ１ , R Ｗ２ and R Ｗ３ represents R in formula (A-1). Ｗ１ , R Ｗ２ and R Ｗ３ is synonymous with.

[0092] In formula (A-3), C ５ represents a ring containing 3 or more carbon atoms and which may have a substituent. ５ The three carbon atoms contained in are the three carbon atoms specified in formula (A-3). The number of carbon atoms in the ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10. The number of carbon atoms in the ring is the number including the three carbon atoms specified in the formula. The ring may be either an aromatic ring or a non-aromatic ring. The ring may be either a monocyclic or polycyclic ring, and is preferably a 5-membered ring, a 6-membered ring, or a fused ring containing at least one of a 5-membered ring and a 6-membered ring. The number of carbon atoms in the fused ring containing at least one of a 5-membered ring and a 6-membered ring is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 10. The ring may have a heteroatom. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, a nitrogen atom, or an oxygen atom is preferred. The number of heteroatoms contained in the ring is preferably 0 to 10, and more preferably 0 to 5. ５ Among the carbon atoms constituting the ring represented by the formula (A-3), the carbon atom at the bonding position marked with * and W ２ Or W ３Carbon atoms other than the carbon atom bonded to may be substituted with a carbonyl carbon (>C=O) or a thiocarbonyl carbon (>C=S). ５ The ring represented by the formula (I) is preferably a ring used as the acidic nucleus. １ The substituents are the same as those that may be possessed by the group.

[0093] In formula (A-3), W ２ and W ３ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ The effect of the invention is more excellent. ２ and W ３ is preferably an oxygen atom.

[0094] In formula (A-4), C ６ represents a ring containing 3 or more carbon atoms which may have a substituent, C ６ A preferred embodiment of the formula (A-3) is C ５ This is the same as the preferred embodiment of W. ４ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ The effect of the invention is more excellent. ２ and W ３ is preferably an oxygen atom. ｄ１ represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified for the substituent W described above.

[0095] Furthermore, the group represented by formula (A-3) is preferably a group represented by formula (C-1) or formula (C-2), and the group represented by formula (A-4) is preferably a group represented by formula (C-3). １ Among these, groups represented by formula (C-1) or formula (C-2) are preferred.

[0096]

[0097] In formula (C-1), C ７ represents an aromatic ring which may have a substituent. ｃ１and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ In formula (C-2), R ｄ２ and R ｄ３ each independently represents a hydrogen atom or a substituent. ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ In formula (C-3), X ｃ６ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ Represents R ｄ１ and R ｄ４ R each independently represents a hydrogen atom or a substituent. Ｗ１ , R Ｗ２ and R Ｗ３ is R in formula (A-3) or formula (A-4). Ｗ１ , R Ｗ２ and R Ｗ３ is synonymous with.

[0098] In formula (C-1), X ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ The effect of the present invention is more excellent, and therefore, X ｃ１ and X ｃ２ Preferably, at least one of X is an oxygen atom, ｃ１ and X ｃ２ is more preferably an oxygen atom.

[0099] In formula (C-1), C ７represents an aromatic ring which may have a substituent. The aromatic ring may be either a monocyclic or polycyclic ring, but a monocyclic ring is preferred. The number of ring members in the aromatic ring is preferably 4 to 30, more preferably 5 to 12, and even more preferably 5 to 8. The number of ring members in the aromatic ring is the number including the two carbon atoms specified in the formula. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but an aromatic hydrocarbon ring is preferred. The above C ７ The aromatic ring represented by the formula (I) is as described above, and is preferably a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a thiophene ring, a furan ring, a thiazole ring, an oxazole ring, a pyridine ring, a thienothiophene ring, a benzothiophene ring, a benzofuran ring, a pyrazine ring, a pyrimidine ring, a thienothiophene ring, or a pyridazine ring, more preferably a benzene ring, a naphthalene ring, or a thiophene ring, and even more preferably a benzene ring. Examples of the substituent that the aromatic ring may have include the groups exemplified by the substituent W, and an alkyl group or a halogen atom is preferred. The number of substituents that the aromatic ring may have is not particularly limited, but is preferably 0 to 8, and more preferably 0 to 4.

[0100] In formula (C-2), X ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ The effect of the present invention is more excellent, and therefore, X ｃ３ and X ｃ４ is preferably an oxygen atom, and X ｃ３ ~X ｃ５ is more preferably an oxygen atom.

[0101] In formula (C-2), R ｄ２ and R ｄ３each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified by the substituent W above, with an alkyl group or an aryl group being preferred, and an alkyl group being more preferred. The alkyl group may be linear, branched, or cyclic, with a linear group being preferred. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 6, even more preferably 1 to 3, and particularly preferably 1 or 2. The aryl group may be monocyclic or polycyclic, with a phenyl group being preferred. The aryl group may further have a substituent, and examples of the substituent include the groups exemplified by the substituent W above.

[0102] In formula (C-3), X ｃ６ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ or =CR Ｗ２ R Ｗ３ The effect of the present invention is more excellent, and therefore, X ｃ６ is preferably an oxygen atom. ｄ１ and R ｄ４ R each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified for the substituent W. ｄ１ Among these, R is preferably an optionally halogenated alkyl group or a cyano group, and more preferably a cyano group. ｄ４ Among these, an aryl group is preferable, and a phenyl group is more preferable.

[0103] The group represented by formula (A-2) is preferably a group represented by formula (A-5), and more preferably a group represented by formula (C-4), in terms of better effects of the present invention.

[0104]

[0105] In formula (A-5), R ａ３ is a cyano group or -COR ｂ２ Represents R ｂ２ is R in formula (A-2) ｂ２ is synonymous with.

[0106] A １is preferably a group represented by formula (A-3) or a group represented by formula (A-5), more preferably a group represented by formula (C-1), a group represented by formula (C-2), or a group represented by formula (C-4), and still more preferably a group represented by formula (C-1) or a group represented by formula (C-2).

[0107] Specific examples of the specific compounds are shown below, but the present invention is not limited to these.

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] In the specific compounds exemplified above, A represents any of the following groups.

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] The molecular weight of the specific compound is preferably 400 to 1000, more preferably 450 to 900, and even more preferably 450 to 800. When the molecular weight is within the above range, the sublimation temperature of the specific compound is lowered, and it is presumed that the specific compound has excellent suitability for production.

[0128] The specific compound preferably has an ionization potential of −5.0 to −6.5 eV in a single film from the viewpoints of stability when used as a p-type organic semiconductor and matching of the energy level with an n-type organic semiconductor.

[0129] The maximum absorption wavelength of the specific compound is preferably in the wavelength range of 400 to 650 nm, more preferably in the range of 450 to 600 nm. The maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) after adjusting the absorption spectrum of the specific compound to a concentration such that the absorbance is 0.5 to 1.0. However, if the specific compound is insoluble in chloroform, the maximum absorption wavelength of the specific compound is determined by evaporating the specific compound and measuring the value using the specific compound in a film state.

[0130] The specific compound is particularly useful as a material for a photoelectric conversion film used in an imaging device, an optical sensor, or a photovoltaic cell. The specific compound often functions as a dye in the photoelectric conversion film. The specific compound can also be used as a coloring material, a liquid crystal material, an organic semiconductor material, a charge transport material, a pharmaceutical material, and a fluorescent diagnostic material.

[0131] The specific compound may be purified as necessary. Examples of methods for purifying the specific compound include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, reslurry washing, reprecipitation purification, and purification using an adsorbent such as activated carbon and recrystallization purification.

[0132] The content of the specific compound in the photoelectric conversion film (=film thickness of the specific compound in terms of a single layer / film thickness of the photoelectric conversion film × 100) is not particularly limited, but is preferably 15 to 75% by volume, more preferably 20 to 60% by volume, and even more preferably 20 to 50% by volume. Only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is in the above range.

[0133] <n-Type Organic Semiconductor> The photoelectric conversion film preferably further contains an n-type organic semiconductor in addition to the specific compound. The n-type organic semiconductor is a compound different from the specific compound. The n-type organic semiconductor is an acceptor organic semiconductor material (compound) and refers to an organic compound that has the property of easily accepting electrons. In other words, the n-type organic semiconductor refers to the organic compound that has a larger electron affinity when two organic compounds are used in contact with each other. In other words, any organic compound can be used as the acceptor organic semiconductor as long as it is an organic compound with electron-accepting properties. Examples of n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof; fused aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); and 5- to 7-membered heterocyclic compounds having at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole, and thiazole). polyarylene compounds; fluorene compounds; cyclopentadiene compounds; silyl compounds; 1,4,5,8-naphthalenetetracarboxylic acid anhydride; 1,4,5,8-naphthalenetetracarboxylic acid diimide derivatives; anthraquinodimethane derivatives; diphenylquinone derivatives; bathocuproine, bathophenanthroline, and derivatives thereof; triazole compounds; distyrylarylene derivatives; metal complexes having a nitrogen-containing heterocyclic compound as a ligand; silole compounds; 3,4,9,10-perylenetetracarboxylic acid dianhydride; 3,4,9,10-perylenetetracarboxylic acid diimide derivatives; and the compounds described in paragraphs

[0056] to

[0057] of JP-A No. 2006-100767.

[0134] As the n-type organic semiconductor (compound), fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred. For example, fullerene C ６０ , fullerene C ７０, fullerene C ７６ , fullerene C ７８ , fullerene C ８０ , fullerene C ８２ , fullerene C ８４ , fullerene C ９０ , fullerene C ９６ , fullerene C ２４０ , fullerene C ５４０ and mixed fullerenes. Examples of fullerene derivatives include compounds in which a substituent is added to the above-mentioned fullerenes. The substituent is preferably an alkyl group, an aryl group, or a heterocyclic group. Preferred fullerene derivatives are the compounds described in JP-A-2007-123707.

[0135] The n-type organic semiconductor may be an organic dye. Examples of the organic dye include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarylium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, acridine dyes, acridinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes, and metal complex dyes.

[0136] The molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.

[0137] The maximum absorption wavelength of the n-type organic semiconductor is preferably 400 nm or less, or in the range of more than 400 nm and 600 nm or less.

[0138] The photoelectric conversion film preferably has a bulk heterostructure formed by mixing a specific compound and an n-type organic semiconductor. The bulk heterostructure is a layer in the photoelectric conversion film in which the specific compound and the n-type organic semiconductor are mixed and dispersed. The photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. The bulk heterostructure is described in detail in paragraphs

[0013] to

[0014] of JP 2005-303266 A.

[0139] The difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.

[0140] When the photoelectric conversion film contains an n-type organic semiconductor, the content of the n-type organic semiconductor in the photoelectric conversion film (thickness of the n-type organic semiconductor in terms of a single layer / thickness of the photoelectric conversion film × 100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 20 to 50 vol%.

[0141] When the n-type organic semiconductor contains fullerenes, the content of the fullerenes relative to the total content of the n-type organic semiconductors (film thickness of fullerenes converted into a single layer / total film thickness of each n-type organic semiconductor converted into a single layer × 100) is preferably 50 to 100% by volume, more preferably 80 to 100% by volume. Fullerenes may be used singly or in combination of two or more types.

[0142] In terms of the response speed of the photoelectric conversion element, the content of the specific compound relative to the total content of the specific compound and the n-type organic semiconductor (film thickness in monolayer equivalent of the specific compound / (film thickness in monolayer equivalent of the specific compound + film thickness in monolayer equivalent of the n-type organic semiconductor) x 100) is preferably 20 to 80% by volume, more preferably 40 to 80% by volume. When the photoelectric conversion film contains an n-type organic semiconductor and a p-type organic semiconductor, the content of the specific compound (film thickness in monolayer equivalent of the specific compound / (film thickness in monolayer equivalent of the specific compound + film thickness in monolayer equivalent of the n-type organic semiconductor + film thickness in monolayer equivalent of the p-type organic semiconductor) x 100) is preferably 15 to 75% by volume, more preferably 30 to 75% by volume. It is preferable that the photoelectric conversion film is substantially composed of the specific compound, the n-type organic semiconductor, and a p-type organic semiconductor that is included as desired. "Substantially" means that the total content of the specific compound, n-type organic semiconductor, and p-type organic semiconductor relative to the total mass of the photoelectric conversion film is 90 to 100% by volume, preferably 95 to 100% by volume, and more preferably 99 to 100% by volume.

[0143] <p-Type Organic Semiconductor> The photoelectric conversion film preferably further contains a p-type organic semiconductor in addition to the specific compound. The p-type organic semiconductor is a compound different from the specific compound. The p-type organic semiconductor is a donor organic semiconductor material (compound) and refers to an organic compound that has the property of easily donating electrons. In other words, the p-type organic semiconductor refers to the organic compound that has a smaller ionization potential when two organic compounds are used in contact with each other. The p-type organic semiconductor may be used alone or in combination of two or more types.

[0144] Examples of p-type organic semiconductors include triarylamine compounds (e.g., N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), compounds described in paragraphs

[0128] to

[0148] of JP-A No. 2011-228614, compounds described in paragraphs

[0052] to

[0063] of JP-A No. 2011-176259, compounds described in paragraphs

[0119] to

[0158] of JP-A No. 2011-225544, compounds, compounds described in paragraphs

[0044] to

[0051] of JP-A No. 2015-153910 and compounds described in paragraphs

[0086] to

[0090] of JP-A No. 2012-094660, etc.), pyrazoline compounds, styrylamine compounds, hydrazone compounds, polysilane compounds, thiophene compounds (for example, thienothiophene derivatives, dibenzothiophene derivatives, benzodithiophene derivatives, dithienothiophene derivatives, [1]benzothieno[3,2-b][1]benzothiophene (BTBT) derivatives, thieno[3,2-f:4,5-f']bis[1]benzthiophene benzothiophene (TBBT) derivatives, compounds described in paragraphs

[0031] to

[0036] of JP 2018-014474 A, compounds described in paragraphs

[0043] to

[0045] of WO 2016 / 194630 A, compounds described in paragraphs

[0025] to

[0037] and

[0099] to

[0109] of WO 2017 / 159684 A, compounds described in paragraphs

[0029] to

[0034] of JP 2017-076766 A, compounds described in paragraphs

[0015] to

[0025] of WO 2018 / 207722 A, compounds described in paragraph [004 5] to

[0053] , compounds described in paragraphs

[0045] to

[0055] of WO2019 / 058995, compounds described in paragraphs

[0063] to

[0089] of WO2019 / 081416, compounds described in paragraphs

[0033] to

[0036] of JP2019-080052A, compounds described in paragraphs

[0044] to

[0054] of WO2019 / 054125, compounds described in paragraphs

[0041] to

[0046] of WO2019 / 093188, compounds described in paragraphs

[0034] to

[0037] of JP2019-050398A,The compounds described in paragraphs

[0033] to

[0036] of JP-A No. 2018-206878, the compounds described in paragraph

[0038] of JP-A No. 2018-190755, the compounds described in paragraphs

[0019] to

[0021] of JP-A No. 2018-026559, the compounds described in paragraphs

[0031] to

[0056] of JP-A No. 2018-170487, the compounds described in paragraphs

[0036] to

[0041] of JP-A No. 2018-16620 Compounds described in paragraphs

[0055] to

[0082] of JP-A No. 2018-113425, compounds described in paragraphs

[0041] to

[0050] of JP-A No. 2018-113425, compounds described in paragraphs

[0044] to

[0048] of JP-A No. 2018-085430, compounds described in paragraphs

[0041] to

[0045] of JP-A No. 2018-056546, compounds described in paragraphs

[0042] to

[0049] of JP-A No. 2018-046267, compounds described in paragraphs

[0043] to

[0044] of JP-A No. 2018-014474 Compounds described in paragraphs

[0031] to

[0036] of WO2018 / 016465, compounds described in paragraphs

[0036] to

[0046] of JP2020-016465A, compounds described in paragraphs

[0045] to

[0048] of JP2020-010024A, etc.), cyanine compounds, oxonol compounds, polyamine compounds, indole compounds, pyrrole compounds, pyrazole compounds, polyarylene compounds, fused aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyarylalkane compounds, pyrazolone compounds, amino-substituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having a nitrogen-containing heterocyclic compound as a ligand. As p-type organic semiconductors, in addition to the above-mentioned compounds, JP 2021-163968 A, JP 2022-027575 A, JP 2022-123944 A, JP 2022-122839 A, JP 2022-120323 A, JP 2022-120273 A, JP 2022-115832 A, JP 2022-108268 A, JP 2022-100258 A,Compounds described in JP-A-2022-181226 and JP-A-2023-005703 can also be used, and these compounds are incorporated herein. Examples of p-type organic semiconductors include compounds with a smaller ionization potential than n-type organic semiconductors, and if this condition is met, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of compounds that can be used as p-type organic semiconductor compounds are listed below.

[0145]

[0146]

[0147]

[0148]

[0149] The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.

[0150] When the photoelectric conversion film contains a p-type organic semiconductor, the content of the p-type organic semiconductor in the photoelectric conversion film (thickness of the p-type organic semiconductor in terms of a single layer / thickness of the photoelectric conversion film × 100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 25 to 50 vol%.

[0151] The photoelectric conversion film containing the specific compound is a non-luminescent film and has characteristics different from those of an organic electroluminescent device (OLED: Organic Light Emitting Diode). A non-luminescent film means a film having a luminescence quantum efficiency of 1% or less, preferably 0.5% or less, more preferably 0.1% or less. The lower limit is often 0% or more.

[0152] <Dye> The photoelectric conversion film may further contain a dye in addition to the specific compound. The dye is a compound different from the specific compound. The dye is preferably an organic dye. Examples of the organic dye include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarylium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, acridine dyes, Examples of the organic dye include acridinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes and metal complex dyes, imidazoquinoxaline dyes described in WO 2020 / 013246, WO 2022 / 168856, JP 2023-10305 A, and JP 2023-10299 A, acceptor-donor-acceptor type dyes in which two acidic nuclei are bonded to a donor, and donor-acceptor-donor type dyes in which two donors are bonded to an acceptor. Among these, cyanine dyes, imidazoquinoxaline dyes, or acceptor-donor-acceptor type dyes are preferred as organic dyes, as they have a maximum absorption wavelength in the preferred range described below.

[0153] The dye is also preferably a compound represented by the following formula (D1).

[0154]

[0155] In formula (D1), k represents an integer of 0 to 3. k is preferably 1 or 2. W １ａ and W ２ａ are each independently -Z ａ =Z ａ −C(A)=Z ａ - or -Z ａ = C(A) - Xａ - represents Z ａ are each independently -CR Ａ = or a nitrogen atom. Ａ represents a hydrogen atom or a substituent. ａ As for -CR Ａ In addition, R Ａ Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W above, and among these, groups selected from the substituent group U are preferred. Ｓｉ１ ) ３ R in Ｓｉ１ is —Si(R Ｓｉ１ ) ３ R Ｓｉ１ Substituent group U: an aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, a halogen atom, an alkoxy group which may have a substituent, and —Si(R Ｓｉ１ ) ３ .

[0156] A is -C(R ２ ) = A ２ R represents a group represented by the formula: ２ represents a hydrogen atom or a substituent, A ２ represents a group represented by the above formula (A-1) or (A-2). ２ Examples of the substituent represented by R include the groups exemplified as the substituent W. ２ is preferably a hydrogen atom. ２ represents a group represented by the above formula (A-1) or (A-2). ２ As the alkyl group, a group represented by the above formula (A-1) is preferable, a group represented by the above formula (A-3) is more preferable, and a group represented by the above formula (C-1) or formula (C-2) is even more preferable.

[0157] X ａ represents an oxygen atom, a sulfur atom, a selenium atom, -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CRＡ４ ２ -, or -C(=CR Ａ５ ２ )-. Ａ１ ~R Ａ５ each independently represents a hydrogen atom or a substituent. ａ is preferably an oxygen atom or a sulfur atom. Ａ１ ~R Ａ５ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above, and among these, an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group is preferred. Specific examples and preferred embodiments of each group are as described in detail for the substituent group S above.

[0158] In the above formula (3a), Y １ａ and Y ２ａ The combination is any one of the following combinations 1 to 4. Combination 1: Y １ａ and Y ２ａ are each independently -Z ａ = Combination 2: Y １ａ and Y ２ａ One of them is -Z ａ =Z ａ - and the other represents a single bond. １ａ and Y ２ａ One of them is -X ａ - and the other represents a single bond. １ａ and Y ２ａ One of the two is -C(T １ａ ) (T ２ａ )-Y ａ -, or -C(=X ｂ )-Y ａ -, and the other represents a single bond.

[0159] In combination 1 and combination 2, Z ａ The definition and preferred embodiments of X are as described above. ａ The definition and preferred embodiments of are as described above. １ａ and T ２ａ each independently represents a hydrogen atom or a substituent. １ａand T ２ａ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above, and among these, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent is preferred. ａ represents an oxygen atom, a sulfur atom, or —NR Ａ８ - represents. Ａ８ represents a hydrogen atom or a substituent. ａ is preferably an oxygen atom. Ａ８ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above, and among these, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent is preferred. ｂ represents an oxygen atom or a sulfur atom. ｂ is preferably an oxygen atom.

[0160] The compound represented by the above formula (D1) is preferably a compound represented by the following formula (D-1) or formula (D-2).

[0161]

[0162] In formula (D-1) and formula (D-2), D １ ~D ５ are each independently a sulfur atom, an oxygen atom, a selenium atom, or —NR Ｄ - represents. Ｄ represents a hydrogen atom or a substituent. １ ~D ５ is preferably an oxygen atom or a sulfur atom. １ and E ２ are each independently -CR Ｅ１ ２ -, -NR Ｅ２ -, -SiR Ｅ３ ２ -, -GeR Ｅ４ ２ represents a sulfur atom, an oxygen atom, or a selenium atom. Ｅ１ ~R Ｅ４ R each independently represents a hydrogen atom or a substituent. Ｄor R Ｅ１ ~R Ｅ４ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above, and among these, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent is preferred. Specific examples and preferred embodiments of each group are as detailed for the substituent group S above. １ ~F ４ are each independently -CR Ｆ = or a nitrogen atom. Ｆ represents a hydrogen atom or a substituent. １ ~F ４ As for -CR Ｆ In addition, R Ｆ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above, and among these, groups selected from the above-mentioned substituent group S are preferred. ３ ~A ６ each independently represents a group represented by the above formula (A-1). ３ ~A ６ As the group represented by the formula (A-3), the group represented by the formula (C-1) or (C-2) is more preferable.

[0163] The maximum absorption wavelength of the dye is preferably in the visible light region, more preferably from 400 to 700 nm, and even more preferably from 400 to 650 nm.

[0164] The content of the dye in the photoelectric conversion film relative to the total content of the specific compound and the dye (=(film thickness of the dye in terms of a single layer / (film thickness of the specific compound in terms of a single layer+film thickness of the dye in terms of a single layer)×100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 20 to 50 vol%.

[0165] In addition to the components described above, the photoelectric conversion film may further contain optional components. Examples of optional components include antioxidants, dispersants, and ultraviolet absorbers. The optional components may also be impurities derived from specific compounds, n-type organic semiconductors, p-type organic semiconductors, or dyes. When the photoelectric conversion film contains optional components, the content of the optional components in the photoelectric conversion film (film thickness of the optional components in terms of a single layer / film thickness of the photoelectric conversion film × 100) is preferably 0.01 to 10% by volume, and more preferably 0.01 to 1% by volume.

[0166] <Film formation method> Examples of the film formation method for the photoelectric conversion film include dry film formation methods. Examples of dry film formation methods include physical vapor deposition methods such as vapor deposition (particularly vacuum deposition), sputtering, ion plating, and MBE (Molecular Beam Epitaxy), as well as CVD (Chemical Vapor Deposition) methods such as plasma polymerization, and vacuum deposition methods are preferred. When forming the photoelectric conversion film by vacuum deposition, manufacturing conditions such as the degree of vacuum and deposition temperature can be set according to conventional methods.

[0167] The thickness of the photoelectric conversion film is preferably from 10 to 1,000 nm, more preferably from 50 to 800 nm, and even more preferably from 50 to 500 nm.

[0168] [Electrodes] The photoelectric conversion element preferably has electrodes. The electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Examples of conductive materials include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident through the upper electrode 15, it is preferable that the upper electrode 15 is transparent to the light to be detected. Examples of materials constituting the upper electrode 15 include conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO: Antimony Tin Oxide, FTO: Fluorine-doped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO: Indium Tin Oxide), and indium zinc oxide (IZO); thin metal films such as gold, silver, copper, chromium, aluminum, and nickel; mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and nanocarbon materials such as carbon nanotubes and graphene. Of these, conductive metal oxides are preferred in terms of high conductivity and transparency.

[0169] Typically, when the conductive film is made thinner than a certain range, the resistance value often increases rapidly. In a solid-state imaging device incorporating a photoelectric conversion element according to this embodiment, the sheet resistance may be 100 to 10,000 Ω / □, and there is a wide degree of freedom in the range of film thickness that can be reduced. Furthermore, the thinner the film thickness of the upper electrode (transparent conductive film) 15, the less light it absorbs, and generally the higher the light transmittance. An increase in light transmittance is desirable because it increases light absorption in the photoelectric conversion film and enhances photoelectric conversion performance. Considering the suppression of leakage current, the increase in the resistance value of the thin film, and the increase in transmittance that accompany a reduction in film thickness, the thickness of the upper electrode 15 is preferably 5 to 100 nm, and more preferably 5 to 20 nm.

[0170] Depending on the application, the lower electrode 11 may be transparent or non-transparent and light-reflecting. Examples of materials constituting the lower electrode 11 include conductive metal oxides such as antimony- or fluorine-doped tin oxide (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metals such as gold, silver, copper, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and carbon materials such as carbon nanotubes and granphenes.

[0171] The method for forming the electrodes can be appropriately selected depending on the electrode material. Specific examples include wet methods such as printing and coating; physical methods such as vacuum deposition, sputtering, and ion plating; and chemical methods such as CVD and plasma CVD. When the electrode material is ITO, examples include electron beam methods, sputtering, resistance heating deposition, chemical reaction methods (such as the sol-gel method), and coating of a dispersion of indium tin oxide.

[0172] [Charge-blocking film: electron-blocking film, hole-blocking film] The photoelectric conversion element preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film. Examples of the intermediate layer include a charge-blocking film. When the photoelectric conversion element has this film, the properties (quantum efficiency, response speed, etc.) of the resulting photoelectric conversion element are more excellent. Examples of the charge-blocking film include an electron-blocking film and a hole-blocking film.

[0173] [Electron Blocking Film] The electron blocking film is a donor organic semiconductor material (compound), and the above-mentioned p-type organic semiconductor can be used. Polymer materials can also be used as the electron blocking film. Examples of polymer materials include polymers of phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, diacetylene, and the like, and derivatives thereof.

[0174] The electron blocking film may be composed of multiple films. The electron blocking film may be composed of an inorganic material. In general, inorganic materials have a higher dielectric constant than organic materials, so when an inorganic material is used for the electron blocking film, a higher voltage is applied to the photoelectric conversion film, resulting in higher quantum efficiency. Examples of inorganic materials that can be used for the electron blocking film include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, indium copper oxide, indium silver oxide, and iridium oxide.

[0175] [Hole-Blocking Film] The hole-blocking film is an acceptor organic semiconductor material (compound), and the n-type organic semiconductors described above can be used. The hole-blocking film may be composed of multiple films.

[0176] Examples of methods for producing a charge blocking film include dry film formation and wet film formation. Examples of dry film formation include vapor deposition and sputtering. Vapor deposition may be either physical vapor deposition (PVD) or chemical vapor deposition (CVD), with physical vapor deposition such as vacuum deposition being preferred. Examples of wet film formation include inkjet printing, spray printing, nozzle printing, spin coating, dip coating, casting, die coating, roll coating, bar coating, and gravure coating, with the inkjet method being preferred in terms of high-precision patterning.

[0177] The thickness of each of the charge blocking films (electron blocking film and hole blocking film) is preferably from 3 to 200 nm, more preferably from 5 to 100 nm, and even more preferably from 5 to 30 nm.

[0178] [Substrate] The photoelectric conversion element may further include a substrate. Examples of the substrate include a semiconductor substrate, a glass substrate, and a plastic substrate. The substrate is usually positioned such that a conductive film, a photoelectric conversion film, and a transparent conductive film are stacked in this order on the substrate.

[0179] [Sealing Layer] The photoelectric conversion element may further have a sealing layer. The performance of photoelectric conversion materials may be significantly degraded in the presence of degrading factors such as water molecules. Therefore, the degradation can be prevented by covering and sealing the entire photoelectric conversion film with a sealing layer made of ceramics such as dense metal oxides, metal nitrides, or metal nitride oxides, or diamond-like carbon (DLC), which do not allow water molecules to penetrate. Examples of sealing layers include those described in paragraphs

[0210] to

[0215] of JP 2011-082508 A, the contents of which are incorporated herein by reference.

[0180] [Method for manufacturing photoelectric conversion element] Examples of methods for manufacturing photoelectric conversion elements include known manufacturing methods. Specifically, for example, methods for manufacturing photoelectric conversion elements include a step of forming a conductive film on a substrate, a step of forming a photoelectric conversion film, and a step of forming a transparent conductive film. The method for manufacturing a photoelectric conversion element may include other steps (for example, a step of forming a charge blocking film and a step of forming a sealing layer) in addition to the above. The method for forming each layer is as described above.

[0181] [Imaging element] An example of an application of a photoelectric conversion element is an imaging element. An imaging element is an element that converts the optical information of an image into an electrical signal, and typically has multiple photoelectric conversion elements arranged in a matrix on the same plane, with each photoelectric conversion element (pixel) converting the optical signal into an electrical signal and outputting the electrical signal pixel by pixel from the imaging element. For this reason, each pixel is composed of one or more photoelectric conversion elements and one or more transistors. The manufacturing method of an imaging element is not particularly limited, but examples include a method including the step of manufacturing the photoelectric conversion element described above.

[0182] [Optical Sensor] Other applications of the photoelectric conversion element include, for example, a photocell and an optical sensor, and the photoelectric conversion element of the present invention is preferably used as an optical sensor. As an optical sensor, the photoelectric conversion element may be used alone, or may be used as a line sensor in which the photoelectric conversion elements are arranged linearly or as a two-dimensional sensor in which the photoelectric conversion elements are arranged on a plane.

[0183] [Compound] The present invention also includes the invention of a compound. The compound of the present invention is the above-mentioned specific compound.

[0184] The present invention will be described in more detail below with reference to the following examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the following examples.

[0185] [Compounds used in photoelectric conversion film] The materials used in the photoelectric conversion film are listed below.

[0186] [Synthesis of Compound (2-1)] Compound (2-1) was synthesized according to the following scheme.

[0187]

[0188] <Synthesis of Compound (2-1-2)> 20 g (67.1 mmol) of compound (2-1-1), 20.2 g (201 mmol) of 2,6-dimethylphenylboronic acid, 72.7 g (336 mmol) of tripotassium phosphate, 2.70 g (3.36 mmol) of SPhos Pd G3 ((2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate), 600 mL of tetrahydrofuran (THF), and 120 mL of water were placed in a glass reaction vessel and heated to reflux under a nitrogen atmosphere for 4 hours. 3.33 g (33.5 mmol) of 2,6-dimethylphenylboronic acid, 14.5 g (67.2 mmol) of tripotassium phosphate, and 0.540 g (0.672 mmol) of SPhos Pd G3 were added to the reaction solution, and the mixture was heated under reflux for an additional 3 hours. After allowing the reaction solution to cool, the layers were separated, and the organic layer was washed with saturated brine. The organic layer was dried over sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The concentrate was suspended in 100 mL of dichloromethane and filtered. The collected solid was suspended in methanol, filtered, and dried under reduced pressure to obtain 15.5 g (44.6 mmol, yield 66.4%) of compound (2-1-2).

[0189] <Synthesis of Compound (2-1-3)> 4.00 g (11.0 mmol) of compound (2-1-2) and 110 mL of THF were placed in a glass reaction vessel and cooled to an internal temperature of −60 to −70°C under a nitrogen atmosphere. 15.1 mL (40.0 mmol) of n-butyllithium (2.66 mol / L) was added dropwise to the mixture at an internal temperature of −60 to −70°C. After stirring the reaction solution for 30 minutes, 7.1 mL (92.0 mmol) of N,N-dimethylformamide (DMF) was added dropwise at an internal temperature of −60 to −70°C. The reaction solution was warmed to room temperature, and saturated aqueous ammonium chloride and ethyl acetate were added, followed by phase separation. The organic layer was washed with saturated saline, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography (hexane / toluene), then dissolved in a mixed solvent of dichloromethane and methanol, and the dichloromethane was distilled off under reduced pressure. The precipitated solid was collected by filtration and dried under reduced pressure to obtain 3.36 g (8.92 mmol, yield 78.0%) of compound (2-1-3).

[0190] <Synthesis of Compound (2-1-4)> 13.0 g (34.5 mmol) of compound (2-1-3) and 260 mL of DMF were placed in a glass reaction vessel, and 18.4 g (104 mmol) of N-bromosuccinimide (NBS) was added, followed by a reaction at 50°C for 3.5 hours. 60 mL of water was added to the reaction solution, and the solid was collected by filtration. The obtained solid was dried under reduced pressure and then dissolved in a mixed solvent of dichloromethane and methanol, and the dichloromethane was distilled off under reduced pressure. The precipitated solid was collected by filtration and then dried under reduced pressure, yielding 13.2 g (29.0 mmol, yield 83.9%) of compound (2-1-4).

[0191] Synthesis of Compound (2-1-5) Compound (2-1-4), 0.538 g (5.27 mmol) of phenylacetylene, 0.0836 g (0.439 mmol) of copper iodide, 0.254 g (0.220 mmol) of tetrakis(triphenylphosphine)palladium, and 40 mL of triethylamine were placed in a glass reaction vessel and heated to reflux under a nitrogen atmosphere for 30 minutes. After allowing the reaction solution to cool, the solvent was distilled off under reduced pressure, and the concentrate was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain 0.350 g (0.734 mmol, yield 16.7%) of compound (2-1-5).

[0192] <Synthesis of Compound (2-1)> 0.300 g (0.630 mmol) of compound (2-1-5), 0.118 g (0.755 mmol) of 1,3-dimethylbarbituric acid, 4.5 mL of toluene, and 12.5 μL (0.127 mmol) of piperidine were placed in a glass reaction vessel and reacted at 80°C for 5 hours under a nitrogen atmosphere. After the reaction solution was allowed to cool, 18 mL of methanol was added, and the solid was collected by filtration. The obtained solid was purified by silica gel column chromatography and then dissolved in a mixed solvent of dichloromethane and methanol. Dichloromethane was distilled off under reduced pressure, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure and purified by sublimation to obtain 0.231 g (0.376 mmol, yield 59.7%) of compound (2-1). １ The H-NMR (Nuclear Magnetic Resonance) data is shown below.１ H-NMR (CDCl ３ ): δ (ppm) = 2.07 (6H, s), 2.20 (6H, s), 3.32 (3H, s), 3.38 (3H, s), 7.18-7.36 (11H, m), 8.35 (1H, s).

[0193] [Synthesis of Compound (4-7)] Compound (4-7) was synthesized according to the following scheme.

[0194]

[0195] In a glass reaction vessel, 0.240 g (0.618 mmol) of compound (4-7-1), 0.116 g (0.741 mmol) of 1,3-dimethylbarbituric acid, 3.6 mL of toluene, and 12.2 μL (0.124 mmol) of piperidine were placed and reacted at 80°C for 1 hour under a nitrogen atmosphere. After the reaction solution was allowed to cool, 18 mL of methanol was added and the solid was collected by filtration. The obtained solid was dissolved in a mixed solvent of dichloromethane and methanol. Dichloromethane was distilled off under reduced pressure, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure and purified by sublimation to obtain 0.197 g (0.374 mmol, yield 60.5%) of compound (4-7). The obtained compound (4-7) １ The H-NMR data is shown below. １ H-NMR (CD ２ Cl ２ ): δ (ppm) = 2.11 (6H, s), 3.36 (3H, s), 3.41 (3H, s), 6.04 (1H, s), 7.23 (1H, t), 7.33-7.37 (3H, m), 7.43-7.47 (2H, m), 7.54 (1H, d), 8.21 (1H, s), 8.78 (1H, s).

[0196] [Synthesis of Compound (7-5)] Compound (7-5) was synthesized according to the following scheme.

[0197]

[0198] Compound (7-5) was synthesized in the same manner as compound (4-7), except that compound (4-7-1) was replaced with compound (7-5-1) and 1,3-dimethylbarbituric acid was replaced with malononitrile.１ The H-NMR data is shown below. １ H-NMR (CD ２ Cl ２ ): δ (ppm) = 2.04 (6H, s), 5.93 (1H, s), 7.19 (1H, t), 7.25-7.27 (2H, m), 7 .31 (1H, t), 7.37-7.41 (2H, m), 7.50 (1H, d), 7.83 (1H, s), 7.99 (1H, s).

[0199] Of the specific compounds and comparative compounds used in the examples and comparative examples, those for which no synthesis examples are given were synthesized according to the above synthesis methods.

[0200] [Specific Compounds] The specific compounds used in the photoelectric conversion film and comparative compounds for comparison are listed below. Note that compounds (C-1) to (C-13) are comparative compounds, and the other compounds are specific compounds.

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] [n-type organic semiconductor] Fullerene (C ６０ )

[0208] [p-type organic semiconductor]

[0209]

[0210] [Evaluation] - Test X - The quantum efficiency (sensitivity), the electric field strength dependence of the quantum efficiency, the response speed, and the electric field strength dependence of the response speed when the photoelectric conversion element received blue-green light were evaluated by the following methods.

[0211] [Fabrication of Photoelectric Conversion Element] A photoelectric conversion element having the configuration shown in FIG. 2 was fabricated using the various components shown above. Here, the photoelectric conversion element comprises a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15. Specifically, amorphous ITO was formed on a glass substrate by sputtering to form a lower electrode 11 (thickness: 30 nm), and compound (EB-1) was further formed on the lower electrode 11 by vacuum heating deposition to form an electron blocking film 16A (thickness: 30 nm). Next, with the glass substrate at room temperature, each specific compound or each comparative compound shown in Tables 1 to 3 and an n-type organic semiconductor (fullerene (C ６０ )) and a p-type organic semiconductor (D-1) were co-deposited by vacuum deposition to form a film having a thickness of 133 nm in terms of a single layer. This resulted in a photoelectric conversion film 12 having a bulk heterostructure of 400 nm. At this time, the film formation rate of the photoelectric conversion film 12 was 1.0 Å / sec. Furthermore, a compound (EB-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). Amorphous ITO was deposited on the hole blocking film 16B by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm). After a SiO film was formed as a sealing layer on the upper electrode 15 by vacuum deposition, aluminum oxide (Al ２ O ３ The resulting laminate was heated in a glove box at 150° C. for 30 minutes to obtain a photoelectric conversion element.

[0212]

[0213] [Dark Current] The dark current of each of the obtained photoelectric conversion elements was measured by the following method. ５ A voltage was applied so as to give an electric field strength of 50 nA / cm, and the current value in a dark place (dark current) was measured. As a result, the dark current was 50 nA / cm for all the photoelectric conversion elements. ２ It was confirmed that the dark current was sufficiently low.

[0214] [Quantum Efficiency (Sensitivity)] The quantum efficiency of each photoelectric conversion element was measured when blue-green light was received by the following method. ５ After applying a voltage to achieve an electric field strength of 100 V / cm, light was irradiated from the upper electrode (transparent conductive film) side to evaluate the quantum efficiency (photoelectric conversion efficiency) at a wavelength of 500 nm, and the quantum efficiency (relative ratio) was calculated according to formula (S1). From the obtained value, the quantum efficiency was evaluated according to the following evaluation criteria. The quantum efficiency is preferably rated C or higher. Formula (S1): Quantum efficiency (relative ratio) = (photoelectric conversion efficiency of each photoelectric conversion element) / (photoelectric conversion efficiency of the photoelectric conversion element of Example 42)

[0215] A: Quantum efficiency (relative ratio) is 1.4 or more. B: Quantum efficiency (relative ratio) is 1.2 or more and less than 1.4. C: Quantum efficiency (relative ratio) is 1.0 or more and less than 1.2. D: Quantum efficiency (relative ratio) is 0.8 or more and less than 1.0. E: Quantum efficiency (relative ratio) is less than 0.8.

[0216] [Dependence of Quantum Efficiency (Sensitivity) on Electric Field Strength] For each photoelectric conversion element, the dependence of quantum efficiency on electric field strength when blue-green light was received was evaluated by the following method. ４ The quantum efficiency at 7.0 V / cm was measured. The electric field strength dependency of the quantum efficiency was calculated according to formula (S2), and the electric field strength dependency of the quantum efficiency was evaluated according to the following evaluation criteria. In formula (S2), the numerator and denominator are values ​​measured for the photoelectric conversion element of the same Example or Comparative Example. The electric field strength dependency of the quantum efficiency is preferably rated C or higher. Formula (S2): Electric field strength dependency of quantum efficiency = (electric field strength of each photoelectric conversion element 7.0 × 10 ４ V / cm) / (electric field strength of each photoelectric conversion element 2.0×10 ５ Quantum efficiency in V / cm

[0217] A: The electric field strength dependency of quantum efficiency is 0.9 or more. B: The electric field strength dependency of quantum efficiency is 0.8 or more and less than 0.9. C: The electric field strength dependency of quantum efficiency is 0.7 or more and less than 0.8. D: The electric field strength dependency of quantum efficiency is 0.6 or more and less than 0.7. E: The electric field strength dependency of quantum efficiency is less than 0.6.

[0218] [Response Speed] The response speed of each photoelectric conversion element when receiving blue-green light was evaluated by the following method. ５ A voltage was applied so that the intensity was 1000 V / cm. Thereafter, the LED (light emitting diode) was momentarily turned on to irradiate light from the upper electrode (transparent conductive film) side, and the photocurrent at a wavelength of 500 nm at that time was measured with an oscilloscope to measure the rise time from 0% signal intensity to 97% signal intensity, and the relative response speed was calculated according to formula (S3). From the obtained value, the response speed was evaluated according to the following evaluation criteria. The response speed is preferably rated C or higher. Formula (S3): Relative response speed = (rise time of each photoelectric conversion element) / rise time of the photoelectric conversion element of Example 42

[0219] A: Relative response speed is less than 0.5 B: Relative response speed is 0.5 or more and less than 1.0 C: Relative response speed is 1.0 or more and less than 2.0 D: Relative response speed is 2.0 or more and less than 3.0 E: Relative response speed is 3.0 or more

[0220] [Dependence of response speed on electric field strength] For each photoelectric conversion element, the dependence of the response speed on electric field strength when blue-green light was received was evaluated by the following method. ４ The rise time at 7.0 V / cm was measured. The electric field strength dependency of the response speed was calculated according to formula (S4), and the electric field strength dependency of the response speed was evaluated according to the following evaluation criteria. In formula (S4), the numerator and denominator are values ​​measured for the photoelectric conversion element of the same Example or Comparative Example. The electric field strength dependency of the response speed is preferably rated C or higher. Formula (S4): Electric field strength dependency of response speed = (electric field strength of each photoelectric conversion element 7.0 × 10 ４ V / cm) / (electric field strength of each photoelectric conversion element 2.0×10 ５ rise time in V / cm)

[0221] A: The electric field strength dependency of the response speed is less than 3.0. B: The electric field strength dependency of the response speed is 3.0 or more and less than 4.0. C: The electric field strength dependency of the response speed is 4.0 or more and less than 5.0. D: The electric field strength dependency of the response speed is 5.0 or more and less than 6.0. E: The electric field strength dependency of the response speed is 6.0 or more.

[0222] [result]

[0223] The evaluation results are shown in Tables 1 to 3 below. The explanation of the structure of the specific compound shown in the "Specific Compound" column in the tables is as follows. １ is a group represented by formula (A-3), formula (A-4) or formula (A-5), it is marked as "A", and in other cases it is marked as "B". １ is a group represented by formula (C-1), formula (C-2), formula (C-3) or formula (C-4), it is designated as "A", and other cases are designated as "B". １ is a group represented by any one of formulas (B1-1), (B2-1), (B3-1), (B4-1) to (B4-3), (B5-1) to (B5-3), and (B6), it is marked as "A", and in other cases it is marked as "B". In the table, in the "Formula (2)" column, if the specific compound is a compound represented by formula (2), it is marked as "A", and in other cases it is marked as "B". In the table, "X １ , Z １ = S R Ｚ１ , R Ｚ２ The "=Ar" column indicates the value of X in formula (1). １ and Z １ is a sulfur atom, and R Ｚ１ and R Ｚ２ is an aromatic ring group which may have a substituent, it is designated as "A", and in other cases it is designated as "B". In the table, in the column "Formula (S1)", when the aromatic ring group which may have a substituent in formula (2) is a group represented by formula (S1), it is designated as "A", and in other cases it is designated as "B".

[0224]

[0225]

[0226]

[0227] From the results shown in Tables 1 to 3, it was confirmed that the photoelectric conversion element of the present invention has excellent sensitivity to blue-green light. Furthermore, from a comparison between Examples 55 and 56, it was confirmed that when the group represented by formula (A-2) in formula (1) is a group represented by formula (A-5), the response speed when blue-green light is received is superior. From a comparison between Examples 54 and 55, it was confirmed that when the group represented by formula (A-5) in formula (1) is a group represented by formula (C-4), the sensitivity is superior. From a comparison between Examples 16 to 35, it was confirmed that when the group represented by formula (A-5) in formula (1) is a group represented by formula (C-4), the sensitivity is superior. １ is a group represented by any one of formula (B1-1), formula (B2-1), formula (B3-1), formula (B4-1) to formula (B4-3), formula (B5-1) to formula (B5-3), and formula (B6), it has been confirmed that at least one of the sensitivity, the electric field strength dependency of the sensitivity, and the electric field strength dependency of the response speed is more excellent. １ and Z １ is a sulfur atom, and R Ｚ１ and R Ｚ２ It was confirmed that when the aromatic ring group which may have a substituent is a group represented by formula (S1) in formula (2), the electric field strength dependence of the sensitivity and the electric field strength dependence of the response speed were more excellent.

[0228] - Test Y - Subsequently, in addition to the specific compound or the comparative compound, photoelectric conversion elements were prepared using the dyes (B-1) to (B-8) shown below other than the specific compound, and the quantum efficiency (sensitivity), the electric field strength dependence of the quantum efficiency, the response speed, and the electric field strength dependence of the response speed at wavelengths of 500 nm and 600 nm of the photoelectric conversion elements were evaluated by the following methods.

[0229]

[0230] <Preparation of Photoelectric Conversion Element> Any of the specific compounds or comparative compounds used in [Preparation of Photoelectric Conversion Element] in the above -Test X-, n-type organic semiconductor (fullerene (C ６０)), a p-type organic semiconductor (compound (D-1)), and any dye selected from dyes (B-1) to (B-8) were co-deposited by vacuum deposition to form a film in a ratio of specific compound (comparative compound):dye:p-type organic semiconductor:n-type organic semiconductor=1:1:2:2 in terms of a single film, and the other procedures were the same as in -Test X- to prepare photoelectric conversion elements for each Example and Comparative Example. As a result, even when a dye other than the specific compound was used in combination, similar results were obtained for the quantum efficiency (sensitivity), the electric field strength dependence of the quantum efficiency, the response speed, and the electric field strength dependence of the response speed shown in Tables 1 to 3.

[0231] 10a, 10b Photoelectric conversion element 11 Conductive film (lower electrode) 12 Photoelectric conversion film 15 Transparent conductive film (upper electrode) 16A Electron blocking film 16B Hole blocking film

Claims

1. A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains a compound represented by formula (1). In formula (1), X １ represents a sulfur atom, an oxygen atom, or a selenium atom. １ and Z ２ one represents a sulfur atom, an oxygen atom, or a selenium atom, and the other represents -CR Ｚ２ = R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a substituent. Ｚ１ and R Ｚ２ At least one of the groups represents a group selected from the substituent group S. The substituent group S includes an aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, and -Si(R Ｓｉ１ ) ３ .R Ｓｉ１ R represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. １ represents a hydrogen atom or a substituent. １ represents a group represented by formula (A-1) or formula (A-2). １ represents a group represented by any one of formulas (B1) to (B12). １ represents a ring containing two or more carbon atoms and which may have a substituent. １ is an oxygen atom, a sulfur atom, ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents R Ｗ１ represents a hydrogen atom or a substituent. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ or -COR Ｗ６ Represents R Ｗ４ ~R Ｗ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ａ１ and R ａ２ each independently represents a cyano group, -COOR ｂ１ , -COR ｂ２ , -SOR ｂ３ , or -SO ２ R ｂ４ Represents R ｂ１ ~R ｂ４ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. １ R represents an aromatic ring group which may have a substituent. ２ and R ３ each independently represents a hydrogen atom or a substituent. ２ represents an aromatic ring group which may have a substituent. ２ represents an aromatic ring which may have a substituent. １ is -C(R Ｃ１ ) (R Ｃ２ )-. Ｃ１ and R Ｃ２ may be bonded to each other to form a ring. n represents an integer of 0 to 4. １ is -CR Ｃ３ In formula (B4) and formula (B11), C represents a nitrogen atom. ３ represents an aromatic ring or a non-aromatic ring in which at least one ring atom is substituted with >C=M. ３ The aromatic ring and the non-aromatic ring represented by the formula (I) may have a substituent. ２ represents a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom. ２ is -CR Ｃ４ = or a nitrogen atom, provided that C ３ The substituents which the aromatic ring and the non-aromatic ring may have do not have a group represented by formula (A-2). ４ represents an aromatic ring or a non-aromatic ring in which at least one ring atom is substituted with >C=M. ４ The aromatic ring and the non-aromatic ring represented by the formula (I) may have a substituent. ３ and Q. ５ Each independently represents -CR Ｃ５ = or a nitrogen atom, Q ４ is -CR Ｃ５ In formula (B6), Q′= or a nitrogen atom. ６ and Q. １２ Each independently represents -CR Ｃ６ = or a nitrogen atom, Q ７ ~Q １１ Each independently represents -CR Ｃ６ In formula (B7), V′= or a nitrogen atom. ３ represents a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom. １３ is -CR Ｃ７ = or a nitrogen atom, Q １４ and Q. １５ Each independently represents -CR Ｃ７ R′= or a nitrogen atom. Ｃ７ In formula (B8), Q′ represents a hydrogen atom or a substituent. １６ and Q. ２０ Each independently represents -CR Ｃ８ = or a nitrogen atom, Q １７ ~Q １９ Each independently represents -CR Ｃ８ In formula (B9), W′= or a nitrogen atom. ５ and W ６ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents R Ｗ１ ~R Ｗ３ is R in the formula (A-1). Ｗ１ ~R Ｗ３ It is the same as V. ４ is -NR Ｎ -, or -C(R Ｃ１ ) (R Ｃ２ )- represents Q ２１ is -CR Ｃ９ = or a nitrogen atom. Ｃ１ ~R Ｃ９ , R Ｃ５ '~R Ｃ８ ' and R Ｎ each independently represents a hydrogen atom or a substituent. Ｃ８ The substituent represented by R′ does not have any of the groups represented by the formula (A-1) and the groups represented by the formula (A-2). Ｃ９ The substituent represented by the formula (A-1) does not have a group represented by the formula (A-1). M is an oxygen atom, a sulfur atom, ═NR Ｍ１ Or = CR Ｍ２ R Ｍ３ Represents R Ｍ１ , R Ｍ２ and R Ｍ３ are R Ｗ１ , R Ｗ２ and R Ｗ３ * indicates the bond position.

2. The photoelectric conversion element according to claim 1, wherein the group represented by formula (A-1) is a group represented by formula (A-3) or formula (A-4), and the group represented by formula (A-2) is a group represented by formula (A-5). In formula (A-3), C ５ represents a ring containing 3 or more carbon atoms which may have a substituent. ２ and W ３ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ In formula (A-4), C ６ represents a ring containing 3 or more carbon atoms which may have a substituent. ４ is an oxygen atom, a sulfur atom, ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents ｄ１ represents a hydrogen atom or a substituent. Ｗ１ , R Ｗ２ and R Ｗ３ is R in the formula (A-1). Ｗ１ , R Ｗ２ and R Ｗ３ In formula (A-5), R ａ３ is a cyano group or -COR ｂ２ Represents R ｂ２ is R in the formula (A-2). ｂ２ * indicates the bond position.

3. The photoelectric conversion element according to claim 2, wherein the group represented by formula (A-3) is a group represented by formula (C-1) or formula (C-2), the group represented by formula (A-4) is a group represented by formula (C-3), and the group represented by formula (A-5) is a group represented by formula (C-4). In formula (C-1), C ７ represents an aromatic ring which may have a substituent. ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ In formula (C-2), R ｄ２ and R ｄ３ Each of X independently represents a hydrogen atom or a substituent. ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ In formula (C-3), X ｃ６ is an oxygen atom, a sulfur atom, ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents Ｗ１ , R Ｗ２ and R Ｗ３ R in the formula (A-3) or (A-4) Ｗ１ , R Ｗ２ and R Ｗ３ It is the same as R. ｄ１ and R ｄ４ each independently represents a hydrogen atom or a substituent. * represents a bonding position.

4. In the formula (1), B １ is a group represented by any one of formulas (B1-1), (B2-1), (B3-1), (B4-1) to (B4-3), (B5-1) to (B5-3), and (B6). The photoelectric conversion element according to claim 1, In formula (B1-1), Ar １１ R represents a monocyclic aromatic ring group which may have a substituent. ２ and R ３ is R in the formula (B1). ２ and R ３ In formula (B2-1), Ar １２ In formula (B3-1), R represents a monocyclic aromatic ring group which may have a substituent. Ｂ１ and R Ｂ２ R each independently represents a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ｂ１ and R Ｂ２ may be bonded to each other to form a ring. １ is -CR Ｃ３ = or a nitrogen atom. Ｃ３ is R in the formula (B3). Ｃ３ It is synonymous with. ３０ ~Q ３３ Each independently represents -CR Ｃ３ R′= or a nitrogen atom. Ｃ３ In formula (B4-1), V′ represents a hydrogen atom or a substituent. ２ is V in the formula (B4). ２ It is synonymous with. ２ is -CR Ｃ４ = or a nitrogen atom. Ｃ４ is R in the formula (B4). Ｃ４ It is synonymous with. ４０ ~Q ４３ Each independently represents -CR Ｃ４ R′= or a nitrogen atom. Ｃ４ In formula (B4-2), V′ represents a hydrogen atom or a substituent. ２ and V ４ each independently represents a sulfur atom, an oxygen atom, or -NR Ｎ - or a selenium atom. ２ is -CR Ｃ４ = or a nitrogen atom. Ｃ４ is R in the formula (B4). Ｃ４ It is synonymous with. ４４ ~Q ４５ Each independently represents -CR Ｃ４ R′= or a nitrogen atom. Ｃ４ In formula (B4-3), V′ represents a hydrogen atom or a substituent. ２ and Q. ２ is V in the formula (B4). ２ and Q. ２ It is the same as: ｂ１ and X ｂ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｘ１ Or = CR Ｘ２ R Ｘ３ Represents R Ｘ１ represents a hydrogen atom or a substituent. Ｘ２ and R Ｘ３ each independently represents a cyano group, —SO ２ R Ｘ４ , -COOR Ｘ５ or -COR Ｘ６ Represents R Ｘ４ ~R Ｘ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ３ is -NR Ｎ -, -C(R Ｂ３ ) (R Ｂ４ In formula (B5-1), Q represents an oxygen atom or a sulfur atom. ３ and Q. ５ Each independently represents -CR Ｃ５ = or a nitrogen atom. Ｃ５ is R in the formula (B5). Ｃ５ It is synonymous with. ４ and Q. ５０ ~Q ５３ is -CR Ｃ５ R′= or a nitrogen atom. Ｃ５ ' is R in the formula (B5). Ｃ５ In formula (B5-2), Q ３ and Q. ５ Each independently represents -CR Ｃ５ = or a nitrogen atom. Ｃ５ is R in the formula (B5). Ｃ５ It is synonymous with. ４ and Q. ５４ is -CR Ｃ５ R′= or a nitrogen atom. Ｃ５ ' is R in the formula (B5). Ｃ５ '. ３ and Z ４ one of which is a sulfur atom, an oxygen atom, or -NR Ｎ - or a selenium atom, and the other is -CR Ｃ５ In formula (B5-3), Q represents a nitrogen atom. ３ ~Q ５ is Q in the formula (B5). ３ ~Q ５ It is the same as: ｂ４ and X ｂ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｘ１ Or = CR Ｘ２ R Ｘ３ Represents R Ｘ１ represents a hydrogen atom or a substituent. Ｘ２ and R Ｘ３ each independently represents a cyano group, —SO ２ R Ｘ４ , -COOR Ｘ５ or -COR Ｘ６ Represents R Ｘ４ ~R Ｘ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ６ is -NR Ｎ -, -C(R Ｂ５ ) (R Ｂ６ )-, an oxygen atom, or a sulfur atom. Ｂ３ ~R Ｂ６ and R Ｎ each independently represents a hydrogen atom or a substituent.

5. The photoelectric conversion element according to any one of claims 1 to 4, wherein the compound represented by formula (1) is a compound represented by formula (2). In formula (2), X １ , R １ , A １ and B １ is X in the formula (1). １ , R １ , A １ and B １ It is synonymous with Z. １１ represents a sulfur atom, an oxygen atom, or a selenium atom. Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a group selected from the above-mentioned substituent group S. Ｚ１ and R Ｚ２ At least one of these represents an aromatic ring group which may have a substituent.

6. In the formula (1), X １ and Z １ is a sulfur atom, R Ｚ１ and R Ｚ２ The photoelectric conversion element according to any one of claims 1 to 4, wherein is an aromatic ring group which may have a substituent.

7. The photoelectric conversion element according to claim 5, wherein in said formula (2), said aromatic ring group which may have a substituent is a group represented by formula (S1). In formula (S1), C ｍ represents an optionally substituted monocyclic aromatic ring. Rs represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group, a halogen atom, a cyano group, or -Si(R Ｓｉ２ ) ３ Represents Ｓｉ２ represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ｓｉ２ The aliphatic hydrocarbon group represented by the formula (I) may have at least one of an ether oxygen atom and a thioether sulfur atom. ｍ The substituent that may be possessed by Rs may be bonded to each other to form a non-aromatic ring. * represents the bonding position.

8. The photoelectric conversion element according to any one of claims 1 to 4, wherein the photoelectric conversion film further contains an n-type organic semiconductor, and the photoelectric conversion film has a bulk heterostructure formed in a state in which the compound represented by formula (1) and the n-type organic semiconductor are mixed.

9. The photoelectric conversion element according to claim 8, wherein the n-type organic semiconductor contains a fullerene selected from the group consisting of fullerene and derivatives thereof.

10. The photoelectric conversion element according to any one of claims 1 to 4, wherein the photoelectric conversion film further contains a p-type organic semiconductor.

11. The photoelectric conversion element according to any one of claims 1 to 4, wherein the photoelectric conversion film further contains a dye.

12. The photoelectric conversion element according to claim 11, wherein the dye is a compound represented by formula (D1). In formula (D1), k represents an integer of 0 to 3. １ａ and W ２ａ Each independently represents -Z ａ =Z ａ -C(A)=Z ａ - or -Z ａ = C(A) - X ａ A represents -C(R ２ ) = A ２ R represents a group represented by the formula: ２ represents a hydrogen atom or a substituent; A ２ represents a group represented by the formula (A-1) or the formula (A-2). １ａ and Y ２ａ The combination is any one of the following combinations 1 to 4. Combination 1: Y １ａ and Y ２ａ Each independently represents -Z ａ = Combination 2: Y １ａ and Y ２ａ One of them is -Z ａ =Z ａ - and the other represents a single bond. １ａ and Y ２ａ One of them is -X ａ - and the other represents a single bond. １ａ and Y ２ａ One of the two is -C(T １ａ ) (T ２ａ ) -Y ａ - or -C (=X ｂ ) -Y ａ - and the other represents a single bond. ａ Each independently represents -CR Ａ = or a nitrogen atom. Ａ represents a hydrogen atom or a substituent. ａ is an oxygen atom, a sulfur atom, a selenium atom, -NR Ａ１ --, --SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ - or -C (=CR Ａ５ ２ )-. Ａ１ ~R Ａ５ Each of T independently represents a hydrogen atom or a substituent. １ａ and T ２ａ Each of Y independently represents a hydrogen atom or a substituent. ａ is an oxygen atom, a sulfur atom, or -NR Ａ８ - represents. Ａ８ represents a hydrogen atom or a substituent. ｂ represents an oxygen atom or a sulfur atom.

13. The photoelectric conversion element according to any one of claims 1 to 4, further comprising one or more intermediate layers between the conductive film and the transparent conductive film in addition to the photoelectric conversion film.

14. An imaging device comprising the photoelectric conversion element according to any one of claims 1 to 4.

15. An optical sensor comprising the photoelectric conversion element according to any one of claims 1 to 4.

16. A method for manufacturing an imaging element, comprising the step of manufacturing a photoelectric conversion element according to any one of claims 1 to 4.

17. A compound represented by formula (1). In formula (1), X １ represents a sulfur atom, an oxygen atom, or a selenium atom. １ and Z ２ one represents a sulfur atom, an oxygen atom, or a selenium atom, and the other represents -CR Ｚ２ = R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a substituent. Ｚ１ and R Ｚ２ At least one of the groups represents a group selected from the substituent group S. The substituent group S includes an aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, and -Si(R Ｓｉ１ ) ３ .R Ｓｉ１ R represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. １ represents a hydrogen atom or a substituent. １ represents a group represented by formula (A-1) or formula (A-2). １ represents a group represented by any one of formulas (B1) to (B12). １ represents a ring containing two or more carbon atoms and which may have a substituent. １ is an oxygen atom, a sulfur atom, ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents R Ｗ１ represents a hydrogen atom or a substituent. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ or -COR Ｗ６ Represents R Ｗ４ ~R Ｗ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ａ１ and R ａ２ each independently represents a cyano group, -COOR ｂ１ , -COR ｂ２ , -SOR ｂ３ , or -SO ２ R ｂ４ Represents R ｂ１ ~R ｂ４ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. １ R represents an aromatic ring group which may have a substituent. ２ and R ３ each independently represents a hydrogen atom or a substituent. ２ represents an aromatic ring group which may have a substituent. ２ represents an aromatic ring which may have a substituent. １ is -C(R Ｃ１ ) (R Ｃ２ )-. Ｃ１ and R Ｃ２ may be bonded to each other to form a ring. n represents an integer of 0 to 4. １ is -CR Ｃ３ In formula (B4) and formula (B11), C represents a nitrogen atom. ３ represents an aromatic ring or a non-aromatic ring in which at least one ring atom is substituted with >C=M. ３ The aromatic ring and the non-aromatic ring represented by the formula (I) may have a substituent. ２ represents a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom. ２ is -CR Ｃ４ = or a nitrogen atom, provided that C ３ The substituents which the aromatic ring and the non-aromatic ring may have do not have a group represented by formula (A-2). ４ represents an aromatic ring or a non-aromatic ring in which at least one ring atom is substituted with >C=M. ４ The aromatic ring and the non-aromatic ring represented by the formula (I) may have a substituent. ３ and Q. ５ Each independently represents -CR Ｃ５ = or a nitrogen atom, Q ４ is -CR Ｃ５ In formula (B6), Q′= or a nitrogen atom. ６ and Q. １２ Each independently represents -CR Ｃ６ = or a nitrogen atom, Q ７ ~Q １１ Each independently represents -CR Ｃ６ In formula (B7), V′= or a nitrogen atom. ３ represents a sulfur atom, an oxygen atom, -NR Ｎ - or a selenium atom. １３ is -CR Ｃ７ = or a nitrogen atom, Q １４ and Q. １５ Each independently represents -CR Ｃ７ R′= or a nitrogen atom. Ｃ７ In formula (B8), Q′ represents a hydrogen atom or a substituent. １６ and Q. ２０ Each independently represents -CR Ｃ８ = or a nitrogen atom, Q １７ ~Q １９ Each independently represents -CR Ｃ８ In formula (B9), W′= or a nitrogen atom. ５ and W ６ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents R Ｗ１ ~R Ｗ３ is R in the formula (A-1). Ｗ１ ~R Ｗ３ It is the same as V. ４ is -NR Ｎ -, or -C(R Ｃ１ ) (R Ｃ２ )- represents Q ２１ is -CR Ｃ９ = or a nitrogen atom. Ｃ１ ~R Ｃ９ , R Ｃ５ '~R Ｃ８ ' and R Ｎ each independently represents a hydrogen atom or a substituent. Ｃ８ The substituent represented by R′ does not have any of the groups represented by the formula (A-1) and the groups represented by the formula (A-2). Ｃ９ The substituent represented by the formula (A-1) does not have a group represented by the formula (A-1). M is an oxygen atom, a sulfur atom, ═NR Ｍ１ Or = CR Ｍ２ R Ｍ３ Represents R Ｍ１ , R Ｍ２ and R Ｍ３ are R Ｗ１ , R Ｗ２ and R Ｗ３ * indicates the bond position.

18. The compound according to claim 17, wherein the group represented by formula (A-1) is a group represented by formula (A-3) or formula (A-4), and the group represented by formula (A-2) is a group represented by formula (A-5). In formula (A-3), C ５ represents a ring containing 3 or more carbon atoms which may have a substituent. ２ and W ３ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ In formula (A-4), C ６ represents a ring containing 3 or more carbon atoms which may have a substituent. ４ is an oxygen atom, a sulfur atom, ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents ｄ１ represents a hydrogen atom or a substituent. Ｗ１ , R Ｗ２ and R Ｗ３ is R in the formula (A-1). Ｗ１ , R Ｗ２ and R Ｗ３ In formula (A-5), R ａ３ is a cyano group or -COR ｂ２ Represents R ｂ２ is R in the formula (A-2). ｂ２ * indicates the bond position.

19. The compound according to claim 18, wherein the group represented by formula (A-3) is a group represented by formula (C-1) or formula (C-2), the group represented by formula (A-4) is a group represented by formula (C-3), and the group represented by formula (A-5) is a group represented by formula (C-4). In formula (C-1), C ７ represents an aromatic ring which may have a substituent. ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ In formula (C-2), R ｄ２ and R ｄ３ Each of X independently represents a hydrogen atom or a substituent. ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ In formula (C-3), X ｃ６ is an oxygen atom, a sulfur atom, ═NR Ｗ１ Or = CR Ｗ２ R Ｗ３ Represents Ｗ１ , R Ｗ２ and R Ｗ３ R in the formula (A-3) or (A-4) Ｗ１ , R Ｗ２ and R Ｗ３ It is the same as R. ｄ１ and R ｄ４ each independently represents a hydrogen atom or a substituent. * represents a bonding position.

20. In the formula (1), B １ is a group represented by any one of formulas (B1-1), (B2-1), (B3-1), (B4-1) to (B4-3), (B5-1) to (B5-3), and formula (B6). In formula (B1-1), Ar １１ R represents a monocyclic aromatic ring group which may have a substituent. ２ and R ３ is R in the formula (B1). ２ and R ３ In formula (B2-1), Ar １２ In formula (B3-1), R represents a monocyclic aromatic ring group which may have a substituent. Ｂ１ and R Ｂ２ R each independently represents a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ｂ１ and R Ｂ２ may be bonded to each other to form a ring. １ is -CR Ｃ３ = or a nitrogen atom. Ｃ３ is R in the formula (B3). Ｃ３ It is synonymous with. ３０ ~Q ３３ Each independently represents -CR Ｃ３ R′= or a nitrogen atom. Ｃ３ In formula (B4-1), V′ represents a hydrogen atom or a substituent. ２ is V in the formula (B4). ２ It is synonymous with. ２ is -CR Ｃ４ = or a nitrogen atom. Ｃ４ is R in the formula (B4). Ｃ４ It is synonymous with. ４０ ~Q ４３ Each independently represents -CR Ｃ４ R′= or a nitrogen atom. Ｃ４ In formula (B4-2), V′ represents a hydrogen atom or a substituent. ２ and V ４ each independently represents a sulfur atom, an oxygen atom, or -NR Ｎ - or a selenium atom. ２ is -CR Ｃ４ = or a nitrogen atom. Ｃ４ is R in the formula (B4). Ｃ４ It is synonymous with. ４４ ~Q ４５ Each independently represents -CR Ｃ４ R′= or a nitrogen atom. Ｃ４ In formula (B4-3), V′ represents a hydrogen atom or a substituent. ２ and Q. ２ is V in the formula (B4). ２ and Q. ２ It is the same as: ｂ１ and X ｂ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｘ１ Or = CR Ｘ２ R Ｘ３ Represents R Ｘ１ represents a hydrogen atom or a substituent. Ｘ２ and R Ｘ３ each independently represents a cyano group, —SO ２ R Ｘ４ , -COOR Ｘ５ or -COR Ｘ６ Represents R Ｘ４ ~R Ｘ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ３ is -NR Ｎ -, -C(R Ｂ３ ) (R Ｂ４ In formula (B5-1), Q represents an oxygen atom or a sulfur atom. ３ and Q. ５ Each independently represents -CR Ｃ５ = or a nitrogen atom. Ｃ５ is R in the formula (B5). Ｃ５ It is synonymous with. ４ and Q. ５０ ~Q ５３ is -CR Ｃ５ R′= or a nitrogen atom. Ｃ５ ' is R in the formula (B5). Ｃ５ In formula (B5-2), Q ３ and Q. ５ Each independently represents -CR Ｃ５ = or a nitrogen atom. Ｃ５ is R in the formula (B5). Ｃ５ It is synonymous with. ４ and Q. ５４ is -CR Ｃ５ R′= or a nitrogen atom. Ｃ５ ' is R in the formula (B5). Ｃ５ '. ３ and Z ４ one of which is a sulfur atom, an oxygen atom, or -NR Ｎ - or a selenium atom, and the other is -CR Ｃ５ In formula (B5-3), Q represents a nitrogen atom. ３ ~Q ５ is Q in the formula (B5). ３ ~Q ５ It is the same as: ｂ４ and X ｂ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｘ１ Or = CR Ｘ２ R Ｘ３ Represents R Ｘ１ represents a hydrogen atom or a substituent. Ｘ２ and R Ｘ３ each independently represents a cyano group, —SO ２ R Ｘ４ , -COOR Ｘ５ or -COR Ｘ６ Represents R Ｘ４ ~R Ｘ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｂ６ is -NR Ｎ -, -C(R Ｂ５ ) (R Ｂ６ )-, an oxygen atom, or a sulfur atom. Ｂ３ ~R Ｂ６ and R Ｎ each independently represents a hydrogen atom or a substituent.

21. The compound according to any one of claims 17 to 20, wherein the compound represented by formula (1) is a compound represented by formula (2). In formula (2), X １ , R １ , A １ and B １ is X in the formula (1). １ , R １ , A １ and B １ It is synonymous with Z. １１ represents a sulfur atom, an oxygen atom, or a selenium atom. Ｚ１ and R Ｚ２ each independently represents a hydrogen atom or a group selected from the above-mentioned substituent group S. Ｚ１ and R Ｚ２ At least one of these represents an aromatic ring group which may have a substituent.

22. In the formula (1), X １ and Z １ is a sulfur atom, R Ｚ１ and R Ｚ２ The compound according to claim 21 , wherein is an aromatic ring group which may have a substituent.

23. The compound according to claim 21, wherein in said formula (2), the aromatic ring group which may have a substituent is a group represented by formula (S1). In formula (S1), C ｍ represents an optionally substituted monocyclic aromatic ring. Rs represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, an optionally substituted aliphatic heterocyclic group, a halogen atom, a cyano group, or -Si(R Ｓｉ２ ) ３ Represents Ｓｉ２ represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ｓｉ２ The aliphatic hydrocarbon group represented by the formula (I) may have at least one of an ether oxygen atom and a thioether sulfur atom. ｍ The substituent that may be possessed by Rs may be bonded to each other to form a non-aromatic ring. * represents the bonding position.

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