Photoelectric conversion element, imaging element, optical sensor, and method for producing imaging element

Abstract

Provided is a photoelectric conversion element having excellent durability of response speed under repeated operation. Also provided are an imaging element, an optical sensor, and a method for manufacturing an imaging element relating to the photoelectric conversion element. A photoelectric conversion element according to the present invention comprises a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains at least one compound selected from the group consisting of compounds represented by formula (N-1) and compounds represented by any one of formulas (1) to (3).

Description

Photoelectric conversion element, image sensor, light sensor, method for manufacturing an image sensor

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

[0002] In recent years, the development of devices having photoelectric conversion films (for example, image sensors) has progressed. For example, Patent Document 1 discloses a photoelectric conversion device having low electric field strength dependence of response speed when receiving blue-green light, which comprises a conductive film, a photoelectric conversion film, and a transparent conductive film in that order, wherein the photoelectric conversion film contains a compound represented by formula (1).

[0003] International Publication No. 2021-221108

[0004] With the increasing demand for improved performance in image sensors and optical sensors, there is a need for photoelectric conversion elements that exhibit superior characteristics. Characteristics required of photoelectric conversion elements include, for example, excellent durability when used repeatedly, and in particular, excellent repeatability of response speed. Specifically, excellent repeatability of response speed means that the response speed does not decrease significantly even when the photoelectric conversion element is used repeatedly. Under these requirements, the present inventors fabricated and investigated a photoelectric conversion element containing the compound disclosed in Patent Document 1, and found that the above-mentioned repeatability of response speed was not always sufficient, indicating room for improvement.

[0005] Therefore, the present invention aims to provide a photoelectric conversion element with excellent repeatability in response speed. Furthermore, the present invention also aims to provide an image sensor, an optical sensor, and a method for manufacturing the image sensor related to the above-mentioned photoelectric conversion element.

[0006] As a result of diligent research to solve the above problems, the inventors have found that the problems can be solved by the following configuration.

[0007] A photoelectric conversion element comprising a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film comprises a compound represented by formula (N-1) described below and at least one selected from the group consisting of compounds represented by any one of formula (1) to formula (3) described below. Ｎ１ The photoelectric conversion element according to [1], wherein the photoelectric conversion film contains two or more compounds represented by any one of formula (1) to formula (3). Ｎ１ The photoelectric conversion element according to [1] or [2], wherein the photoelectric conversion film contains at least one compound represented by formula (1). Ｎ２ The photoelectric conversion element according to any one of [1] to [3], wherein X is an oxygen atom or -NR-. Ｗ１ The photoelectric conversion element according to any one of [1] to [4], wherein both Y and Y are an oxygen atom or =NR. Ｗ１ R has the same definition as R in formula (N-1) described above. Ｗ１ The photoelectric conversion element according to any one of [1] to [5], wherein the compound represented by formula (N-1) is a compound represented by any one of formulas (N-11) to (N-13) described below. Ｗ１ The photoelectric conversion element according to any one of [1] to [6], wherein the compound represented by formula (N-1) is a compound represented by any one of formulas (N-21) to (N-26) described below. １１ The photoelectric conversion element according to [7], wherein in formulas (N-21) to (N-26), each X is independently an oxygen atom or -NR-. １１ The photoelectric conversion element according to [7] or [8], wherein in formulas (N-21) to (N-26), each Y is independently an oxygen atom or =NR. １１ The photoelectric conversion element according to any one of [1] to [9], wherein in formula (1), A is a group represented by formula (A-1) or formula (A-2), n11 is 0, and D is a group represented by formula (D-1). １１ In formula (1), A is a hydrogen atom, n11 is 0 or 1, and DA photoelectric conversion element according to any one of [1] to [9], wherein is a base represented by the above formula (D-1).

[12] In the above formula (2), X ２１ ga-NR １ｓ - or -CR ２ｓ ２ - A photoelectric conversion element according to any one of [1] to

[11] .

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

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

[14] A photoelectric conversion element according to any one of [1] to

[13] , wherein the photoelectric conversion film further comprises fullerenes selected from the group consisting of fullerenes and their derivatives.

[15] A photoelectric conversion element according to any one of [1] to

[14] , wherein the photoelectric conversion film further comprises a p-type organic semiconductor.

[16] A photoelectric conversion element according to any one of [1] to

[15] , wherein there is one or more intermediate layers between the conductive film and the transparent conductive film in addition to the photoelectric conversion film.

[17] A photoelectric conversion element according to

[16] , wherein the intermediate layer is an electron blocking film or a hole blocking film.

[18] An image sensor having a photoelectric conversion element as described in any one of [1] to

[17] .

[19] A light sensor having a photoelectric conversion element as described in any one of [1] to

[17] .

[20] A method for manufacturing an image sensor, comprising a step of manufacturing a photoelectric conversion element as described in any one of [1] to

[17] .

[0008] According to the present invention, a photoelectric conversion element with excellent repeatability in response speed can be provided. Furthermore, according to the present invention, an image sensor, an optical sensor, and a method for manufacturing the image sensor can also be provided, relating to the above-mentioned photoelectric conversion element.

[0009] This is a schematic cross-sectional diagram showing one example of the configuration of a photoelectric conversion element.

[0010] The present invention will now be described in detail. The following descriptions of constituent elements may be based on typical embodiments of the present invention, but the present invention is not limited to such embodiments.

[0011] The following is a definition of each description in this specification. In this specification, a numerical range indicated by "~" means a range that includes the numbers indicated before and after "~" as the lower and upper limits. In this specification, in numerical ranges described in steps, the upper or lower limit indicated in one numerical range may be replaced with the upper or lower limit of another numerical range described in steps. Also, in numerical ranges described in this specification, the upper or lower limit indicated in one numerical range may be replaced with the values ​​shown in the examples. In this specification, a combination of two or more preferred embodiments is a more preferred embodiment.

[0012] In this specification, hydrogen atoms may be light hydrogen atoms (ordinary hydrogen atoms) and deuterium atoms (e.g., dihydrogen atoms). In this specification, with respect to compounds that may have geometric isomers (cis-trans isomers), the general formula or structural formula representing the above compound may, for convenience, be described in only one of the cis or trans forms. Even in such cases, unless otherwise specified, the form of the above compound is not limited to either the cis or trans form, and the above compound may be in either the cis or trans form. Furthermore, in this specification, with respect to compounds having a chiral atom, the general formula or structural formula representing the above compound may, for convenience, be described without distinguishing between stereoisomers. Even in such cases, unless otherwise specified, the form of the above compound is not limited to either, and may be in either form or a mixture thereof. For example, a compound having a chiral carbon atom may, unless otherwise specified, be either the S-form or the R-form, or a mixture thereof.

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

[0014] The symbol "*" in a chemical formula indicates a bond position unless otherwise specified. In this specification, when there are multiple substituents and linking groups etc. (hereinafter also referred to as "substituents etc.") indicated by a specific symbol, or when multiple substituents etc. are specified simultaneously, it means that each substituent etc. may be identical or different from the others. The same applies to the specification of the number of substituents etc. In this specification, unless otherwise specified, "substituent" refers to the group exemplified by substituent W described later.

[0015] (Substituent W) The substituent W used herein is described below. Substituent W is, for example, a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, and iodine atom), an alkyl group (including cycloalkyl groups, bicycloalkyl groups, and tricycloalkyl groups), an alkenyl group (including cycloalkenyl groups and bicycloalkenyl groups), an alkynyl group, an aryl group, a heterocyclic group (heteroaryl group, or 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, or an alkoxycarbonyloxy group. Examples of substituents include aryloxycarbonyloxy groups, primary, secondary, or tertiary amino groups (including anilino groups), alkylthio groups, arylthio groups, heterocyclic thio groups, alkyl or arylsulfinyl groups, alkyl or arylsulfonyl groups, acyl groups, aryloxycarbonyl groups, alkoxycarbonyl groups, aryl or heterocyclic azo groups, imide groups, phosphino groups, phosphinyl groups, phosphinyloxy groups, phosphinylamino groups, phosphono groups, hydroxyl groups, thiol groups, acylamino groups, carbamoyl groups, and ureido groups. Furthermore, each of the above groups may have further substituents (for example, one or more of the above groups) if possible. For example, alkyl groups that may have substituents are also included as one form of substituent W. When substituent W has carbon atoms, the number of carbon atoms in substituent W is, for example, 1 to 20. The number of atoms other than hydrogen atoms in substituent W is, for example, 1 to 30. The specific compounds described later may have substituents such as carboxyl group, salt of carboxyl group, salt of phosphate group, sulfonic acid group, salt of sulfonic acid group, hydroxyl group, thiol group, acylamino group, carbamoyl group, ureido group, or boronic acid group (-B(OH)). ２ ) and / or the absence of a primary amino group is also preferable.

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

[0017] In this specification, unless otherwise specified, the alkyl group portion of an alkoxy group is preferably the alkyl group described above. The alkyl group portion of an alkylthio group is preferably the alkyl group described above. In an alkoxy group which may have substituents, examples of substituents that the alkoxy group may have are the same as those for substituents in an alkyl group which may have substituents. In an alkylthio group which may have substituents, examples of substituents that the alkylthio group may have are the same as those for substituents in an alkyl group which may have substituents.

[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 an alkenyl group which may have substituents, examples of substituents that the alkenyl group may have are the same as examples of substituents in an alkyl group which may have substituents. 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 an alkynyl group which may have substituents, examples of substituents that the alkynyl group may have are the same as examples of substituents in an alkyl group which may have substituents.

[0019] In this specification, unless otherwise specified, aromatic rings constituting an aromatic ring or aromatic ring group may be monocyclic or polycyclic (e.g., 2 to 6 rings). A monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as its ring structure. A polycyclic (e.g., 2 to 6 rings) aromatic ring is an aromatic ring in which multiple (e.g., 2 to 6) aromatic ring structures are fused together as its ring structure. The number of ring member atoms of the above aromatic ring is preferably 4 to 15. The above aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring. If the above aromatic ring is an aromatic heterocyclic ring, the number of heteroatoms having as ring member atoms is, for example, 1 to 10. Examples of the above heteroatoms include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron. Examples of the above aromatic hydrocarbon ring include a benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring.Examples of the above aromatic heterocycles include pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings (e.g., 1,2,3-triazine rings, 1,2,4-triazine rings, and 1,3,5-triazine rings), tetrazine rings (e.g., 1,2,4,5-tetrazine rings), quinoxaline rings, pyrrole rings, furan rings, thiophene rings, imidazole rings, oxazole rings, thiazole rings, benzopyrrole rings, benzofuran rings, benzothiophene rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, naphthopyrrole rings, naphthofuran rings, naphthothiophene rings, naphtoimidazole rings, naphthoxazole rings, pyrroloimidazole rings (e.g., 5H-pyrrolo[1,2-a]imidazole rings), and imidazoxazole rings (e.g., imidazo[2,1-b]oxazole rings). , thienothiazole ring (e.g., thieno[2,3-d]thiazole ring, etc.), benzothiadiazole ring, benzodithiophene ring (e.g., benzo[1,2-b:4,5-b']dithiophene ring, etc.), thienothiophene ring (e.g., thieno[3,2-b]thiophene ring, etc.), thiazolothiazole ring (e.g., thiazolo[5,4-d]thiazole ring, etc.), naphthodithiophene ring (e.g., naphtho[2,3 Examples include the -b:6,7-b']dithiophene ring, naphtho[2,1-b:6,5-b']dithiophene ring, naphtho[1,2-b:5,6-b']dithiophene ring and 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. In an aromatic ring which may have substituents, examples of substituents that the aromatic ring may have include the group exemplified by substituent W. If the aromatic ring has substituents, the number of substituents may be one or more (for example, 1 to 4). In this specification, when referring to an aromatic ring group, examples include a group obtained by removing one or more hydrogen atoms (for example, 1 to 5) from the above aromatic ring. In this specification, when referring to an aryl group, examples include a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic hydrocarbon ring among the aromatic rings mentioned above.In this specification, when referring to a heteroaryl group, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above aromatic rings. In this specification, when referring to an arylene group, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings. In this specification, when referring to a heteroarylene group, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above aromatic rings. In the 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 groups may have include, for example, the group exemplified by substituent W. When these optionally substituted groups have substituents, the number of substituents may be one or more (for example, 1 to 4).

[0020] In this specification, the number of ring members of the aliphatic heterocyclic group is preferably 5 to 20, more preferably 5 to 12, and even more preferably 6 to 8. Examples of heteroatoms that the aliphatic heterocyclic group has include sulfur, oxygen, nitrogen, selenium, tellurium, phosphorus, silicon, and boron atoms, with sulfur, oxygen, or nitrogen atoms being preferred. Examples of aliphatic heterorings that constitute the aliphatic heterocyclic group include pyrrolidine rings, oxolane rings, thiolane rings, piperidine rings, tetrahydropyran rings, thiane rings, piperazine rings, morpholine rings, quinuclidine rings, azetidine rings, oxetane rings, aziridine rings, dioxane rings, and γ-butyrolactone.

[0021] In this specification, unless otherwise specified, if there are two or more bond positions represented by * in a formula, the direction of the bond is not particularly limited. For example, in a compound represented by the formula "X-Y-Z", if Y is a group represented by *-A-B-*, the compound may be either "X-A-B-Z" or "X-B-A-Z". Also, for example, a structure in which a ring represented by formula (X1) and a ring represented by formula (X2) are fused at a bond position represented by * may be either the structure represented by formula (X3) or the structure represented by formula (X4).

[0022]

[0023] [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, wherein the photoelectric conversion film includes a compound represented by formula (N-1) and at least one compound selected from the group consisting of compounds represented by any of formulas (1) to (3) (hereinafter also simply referred to as "specific compounds"). The mechanism by which the above configuration of the photoelectric conversion element of the present invention can solve the problems of the present invention is not necessarily clear, but the inventors have speculated as follows. However, the following speculation does not limit the mechanism by which the effect is obtained. That is, even if the effect is obtained by a mechanism other than the one described below, it is included in the scope of the present invention.

[0024] Conventional technology uses fullerene C as an n-type semiconductor. ６０ Many photoelectric conversion elements using fullerenes such as C have been reported, ６０ In photoelectric conversion elements using materials such as fullerene C, it became clear that the degradation of the photoelectric conversion characteristics was significant when the characteristics were repeatedly evaluated. For example, when the response speed was repeatedly evaluated, a decrease in the response speed was observed. Therefore, the inventors developed fullerene C ６０ When a specific compound represented by formula (N-1) was used as an n-type semiconductor other than the one specified above, and further, when a specific compound represented by any of formulas (1) to (3) was used in combination, it was surprisingly confirmed that the change in response speed was small even when repeated evaluations were performed. Although the detailed mechanism is unknown, it is presumed that the combination of the two compounds above successfully suppressed the aggregation of the compounds in the photoelectric conversion film and allowed them to be well dispersed in the photoelectric conversion film. Hereafter, the improved repeated durability of the response speed of the photoelectric conversion element will also be referred to as the improved effect of the present invention. The configuration of the photoelectric conversion element of the present invention will be described in detail below.

[0025] Figure 1 shows a schematic cross-sectional view of one embodiment of the photoelectric conversion element of the present invention. The photoelectric conversion element 10a shown in Figure 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 that functions 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 that functions as an upper electrode are stacked in this order. Figure 2 shows an example of the configuration of another photoelectric conversion element. The photoelectric conversion element 10b shown in Figure 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 on the lower electrode 11 in this order. Note that the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in Figures 1 and 2 may be appropriately changed depending on the application and characteristics.

[0026] In the photoelectric conversion element 10a (or 10b), it is preferable that light is incident on the photoelectric conversion film 12 via the upper electrode 15. Furthermore, when using the photoelectric conversion element 10a (or 10b), a voltage can be applied. In this case, the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and between this pair of electrodes, 1 × 10⁻¹⁰ －５ ~1 x 10 ７ It is preferable to apply a voltage of V / cm. In terms of performance and power consumption, the applied voltage should be 1 × 10⁻⁶. －４ ~1 x 10 ７ V / cm is more preferable, 1 × 10 －３ ~5 x 10 ６ A voltage of V / cm is even more preferable. Regarding the voltage application method, it is preferable to apply the voltage so that the electron blocking film 16A side becomes the cathode and the photoelectric conversion film 12 side becomes the anode, as shown in Figures 1 and 2. The same method can be used to apply the voltage when the photoelectric conversion element 10a (or 10b) is used as a light sensor or when it is incorporated into an image sensor. As will be described in detail later, the photoelectric conversion element 10a (or 10b) is suitably applicable to image sensor applications. The configuration of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.

[0027] [Photoelectric Conversion Film] The photoelectric conversion element of the present invention has a photoelectric conversion film containing a compound represented by formula (N-1) and at least one selected from the group consisting of compounds represented by any one of formulas (1) to (3). Hereinafter, each of these compounds will be described in detail.

[0028] <Compound Represented by Formula (N-1)> Hereinafter, the compound represented by formula (N-1) (hereinafter sometimes simply referred to as "compound N-1") will be described in detail. Note that compound N-1 can function as an n-type organic semiconductor. An n-type organic semiconductor is an acceptor-type organic semiconductor material (compound), and refers to an organic compound having a property of easily accepting electrons. That is, an n-type organic semiconductor refers to the organic compound having higher electron affinity when two organic compounds are used in contact with each other.

[0029]

[0030] In formula (N-1), Ar Ｎ１represents a condensed polycyclic aromatic ring, which may have substituents. The number of ring structures in the condensed polycyclic aromatic ring is preferably 2 to 10, more preferably 2 to 8, and even more preferably 2 to 6. The condensed polycyclic aromatic ring may be either an aromatic hydrocarbon or an aromatic heterocycle. Specific examples of condensed polycyclic aromatic rings include naphthalene, acenaphthylene, acenaphthene, phenalene, pyrene, quinoline, isoquinoline, quinoxaline, indene, azulene, fluorene, phenanthrene, anthracene, tetracene, pentacene, hexacene, heptacene, fluoranthene, carbazole, dibenzofuran, dibenzothiophene, acridine, xanthene, thioxanthene, benzo[c]fluorene, benzo[a]anthracene, pyrene, triphenylene, chrysene, tetracene, Examples of rings selected from the group consisting of pentacene, benzo[a]pyrene, benzo[e]acephenanthrylene, benzo[k]fluorantene, benzo[j]fluorantene, dibenzo[a,h]anthracene, dibenzo[g,p]chrysene, perylene, 1,7-diazaperylene, coronene, ovalene, corannulene, benzo[ghi]perylene, dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, dibenzo[a,l]pyrene, indeno[1,2,2-c,d]pyrene, and porphyrins. Ｎ１ Among the condensed polycyclic aromatic rings represented by , rings selected from naphthalene, corannarene, pyrene, and 1,7-diazaperylene are preferred.

[0031] Ar Ｎ１ Examples of substituents that the condensed polycyclic aromatic ring represented by may have include the groups exemplified by substituent W, and preferred substituents are an aliphatic hydrocarbon group, an aromatic ring group, an aliphatic heterocyclic group, an alkoxy group, an aryloxy group, an acyl group, a silyl group, a halogen atom, a cyano group, or a nitro group. Ｎ１ When a condensed polycyclic aromatic ring represented by has substituents, the number of substituents can be one or more (for example, 1 to 4), but Ar Ｎ１ The condensed polycyclic aromatic ring represented by is preferably without substituents.

[0032] In the above formula (N-1), n represents an integer of 1 or more. n is preferably 1 to 6, more preferably 1 to 4, and still more preferably 2 to 4.

[0033] In the above formula (N-1), X Ｎ１ represents an oxygen atom, -NR-, -C(R) ２ -, or a sulfur atom. R represents a hydrogen atom or a substituent. X Ｎ１ is preferably an oxygen atom, -NR-, or -C(R) ２ -, more preferably an oxygen atom or -NR-, and still more preferably an oxygen atom. R is preferably a substituent, and specific examples thereof include groups exemplified as the substituent W. Among these, an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group is preferred, and an optionally substituted aliphatic hydrocarbon group or an optionally substituted aromatic ring group is more preferred.

[0034] The above aliphatic hydrocarbon group may be linear, branched or cyclic. Examples of the above aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group, with an alkyl group being preferred. The number of carbon atoms in the linear aliphatic hydrocarbon group is preferably 1 to 20, more preferably 1 to 10, still more preferably 1 to 4, and particularly preferably 1 or 2. The number of carbon atoms in the branched aliphatic hydrocarbon group is preferably 3 to 20, more preferably 3 to 10, still more preferably 3 to 7, and particularly preferably 3 to 5. The cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic. The number of carbon atoms in the cyclic aliphatic hydrocarbon group is preferably 3 to 20, more preferably 3 to 10, and still more preferably 3 to 6.

[0035] The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group. If the aromatic ring group has substituents, the number is not particularly limited, but 1 to 3 is preferred. The above aromatic ring group may be either monocyclic or polycyclic, with monocyclic being preferred. The number of ring members of the above aromatic ring group is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. The definition and specific examples of the above aromatic hydrocarbon group are as described above, with a phenyl group or a naphthyl group being preferred, and a phenyl group being more preferred. Examples of heteroatoms that the above aromatic heterocyclic group may have 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, with a nitrogen atom, a sulfur atom, or an oxygen atom being preferred. The definition and specific examples of the above aromatic heterocyclic group are as described above, with a pyridine ring group, a furan ring group, or a thiophene ring group being preferred.

[0036] The definition of an aliphatic heterocyclic group is as described above. In an aliphatic heterocyclic group that may have substituents, the number of ring members of the aliphatic heterocyclic group is preferably 5 to 20, more preferably 5 to 12, and even more preferably 5 to 8. The number of carbon atoms in the aliphatic heterocyclic group is preferably 1 to 20. Examples of heteroatoms that the aliphatic heterocyclic group may have include sulfur, oxygen, nitrogen, selenium, tellurium, phosphorus, silicon, and boron atoms, with sulfur, oxygen, or nitrogen atoms being preferred.

[0037] In the above formula (N-1), Y Ｎ１ and Y Ｎ２ These are, independently, an oxygen atom, a sulfur atom, and =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ Represents R Ｗ１ R represents a hydrogen atom or substituent. Ｗ２ and R Ｗ３ These are, independently, a cyano group and a -COOR group. Ｗ４ , -COR Ｗ５ , or -SO ２ R Ｗ６ Represents R Ｗ４ ~R Ｗ６Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. Ｎ１ and Y Ｎ２ As for each, independently, oxygen atom, sulfur atom, or =NR Ｗ１ Preferably, an oxygen atom, or =NR Ｗ１ More preferable, Y Ｎ１ and Y Ｎ２ However, all of them are (Y Ｎ１ and Y Ｎ２ Both are oxygen atoms, or =NR Ｗ１ It is even more preferable that this be the case.

[0038] R Ｗ１ A substituent is preferred, and specific examples include the group exemplified by substituent W, among which optionally substituted aliphatic hydrocarbon groups, optionally substituted aromatic ring groups, or optionally substituted aliphatic heterocyclic groups are preferred, and optionally substituted aliphatic hydrocarbon groups or optionally substituted aromatic ring groups are more preferred. The definitions and preferred embodiments of optionally substituted aliphatic hydrocarbon groups, optionally substituted aromatic ring groups, and optionally substituted aliphatic heterocyclic groups are the same as those of the substituent represented by R. Ｗ２ and R Ｗ３ A cyano group is preferred as the component. Also, R Ｗ４ ~R Ｗ６ The definitions and preferred embodiments of the optionally substituted aliphatic hydrocarbon group, optionally substituted aromatic ring group, and optionally substituted aliphatic heterocyclic group are the same as those of the substituent represented by R.

[0039] Note, X Ｎ１ is -NR- and Y Ｎ１ and Y Ｎ２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１These may bond to each other to form a ring. The ring is not particularly limited as long as it contains two nitrogen atoms, and may be either an aromatic ring or a non-aromatic ring, but an aromatic ring is preferred. The number of members of the ring is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. Among these, X Ｎ１ is -NR- and Y Ｎ１ ga = NR Ｗ１ And R and R Ｗ１ When the two elements are bonded to each other to form a ring, formula (N-1) is preferably formula (N-1n).

[0040]

[0041] In formula (N-1n), Ar Ｎ１ , C １ , Y Ｎ１ and n are Ar in formula (N-1) above. Ｎ１ , C １ , Y Ｎ１ And is synonymous with n, and the preferred embodiment is also the same. Ar ＸＹ The symbol (N-1n) represents an aromatic ring fused with the imidazole ring as explicitly shown in the formula. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, but an aromatic heterocycle is preferred. The aromatic ring may also be monocyclic or polycyclic, but a monocyclic ring is preferred. The number of members in the aromatic ring is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. The definition and specific examples of an aromatic hydrocarbon ring are as described above, with a benzene ring being particularly preferred. Examples of heteroatoms in an aromatic heterocycle include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron atoms, with nitrogen, sulfur, or oxygen atoms being preferred, and nitrogen atoms being more preferred. The definition and specific examples of the aromatic heterocyclic group are as described above, with a pyridine ring, pyridazine ring, or pyrazine ring being preferred.

[0042] In the above formula (N-1), C １ is, X Ｎ１ Includes the above Ar Ｎ１ This represents a fused polycyclic aromatic ring and a fused ring. １ The ring represented by Ar Ｎ１The mode of condensation with the fused polycyclic aromatic ring represented by is not particularly limited, and may be ortho-fused or ortho-peri-fused. In addition, C １ The number of ring members of the ring represented by is preferably 5 to 18, more preferably 5 to 10, and still more preferably 5 to 6. The above number of ring members refers to two carbon atoms in formula (N-1), and X Ｎ１ is a number including.

[0043] From the viewpoint that the effect of the present invention is more excellent, C １ As the ring represented by, a ring represented by the following formula (C-1) or the following formula (C-2) is preferable.

[0044]

[0045] In formula (C-1) and formula (C-2), X Ｎ１ , Y Ｎ１ and Y Ｎ２ have the same meanings as X Ｎ１ , Y Ｎ１ and Y Ｎ２ in the above formula (N-1), and preferred embodiments are also the same. * and *p each represent a ring fusion position. Specifically, the ring represented by formula (C-1) shares bonds at two carbon atoms which are the ring fusion position marked with *, thereby Ar Ｎ１ is ortho-fused with the fused polycyclic aromatic ring represented by; the ring represented by formula (C-2) shares bonds at three carbon atoms which are the ring fusion position marked with *p, thereby Ar Ｎ１ is ortho-peri-fused with the fused polycyclic aromatic ring represented by.

[0046] From the viewpoint that the effect of the present invention is more excellent, the compound N-1 is preferably a compound represented by any one of formulas (N-11) to (N-13), and more preferably a compound represented by formula (N-11) or (N-12). Among these, the compound N-1 is preferably a compound represented by any one of formulas (N-21) to (N-26), and more preferably a compound represented by any one of formulas (N-22) to (N-26).

[0047]

[0048] In formulas (N-11) to (N-13), X Ｎ２１ , X Ｎ２２ , XＮ３１ , X Ｎ３２ and X Ｎ４１ have the same definitions as X in Formula (N-1) above Ｎ１ , and preferred embodiments thereof are also the same. Among them, X Ｎ２１ , X Ｎ２２ , X Ｎ３１ , X Ｎ３２ and X Ｎ４１ are each independently preferably an oxygen atom or -NR-. Y Ｎ２１ to Y Ｎ２４ , Y Ｎ３１ to Y Ｎ３４ , Y Ｎ４１ and Y Ｎ４２ have the same definitions as Y in Formula (N-1) above Ｎ１ , and preferred embodiments thereof are also the same. m7 and m9 each independently represent an integer of 1 or greater, and m8 represents an integer of 0 or greater. m7 is preferably 1 to 5, more preferably 1 to 4, still more preferably 1 to 3, and particularly preferably 1. m8 is preferably 0 to 3, more preferably 0 to 2, and still more preferably 0 to 1. m9 is preferably 2 to 5, more preferably 2 to 4, and still more preferably 2 to 3.

[0049] In the above Formulas (N-11) to (N-13), each Z independently represents =CR Ｚ - or a nitrogen atom. R Ｚ represents a hydrogen atom or a substituent. In each of the above Formulas (N-11) to (N-13), the number of nitrogen atoms among the plurality of Z present is preferably 2 or less, more preferably 1 or less, and it is preferable that all Z in each formula are =CR Ｚ -. R Ｚ is preferably a hydrogen atom. R ＺWhen is a substituent, specific examples include the groups exemplified by substituent W, among which optionally substituted aliphatic hydrocarbon groups, optionally substituted aromatic ring groups, or optionally substituted aliphatic heterocyclic groups are preferred, and optionally substituted aliphatic hydrocarbon groups or optionally substituted aromatic ring groups are more preferred. The definitions and preferred embodiments of optionally substituted aliphatic hydrocarbon groups, optionally substituted aromatic ring groups, and optionally substituted aliphatic heterocyclic groups are the same as those of substituents represented by R. Also, when both Zs are R Ｚ is a substituent = CR Ｚ - If R Ｚ The substituents represented by may bond to each other to form a ring. The above ring is not particularly limited and may be either an aromatic ring or a non-aromatic ring, but an aromatic ring is preferred. The number of members of the above ring is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. If the above ring is an aromatic ring, it may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but an aromatic hydrocarbon ring is preferred. Furthermore, the aromatic ring may be either a monocyclic or polycyclic ring, but a monocyclic ring is preferred. The definition and specific examples of an aromatic hydrocarbon ring are as described above, but among them, a benzene ring is preferred. Examples of heteroatoms that the aromatic heterocyclic ring has include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron atoms, with nitrogen, sulfur, or oxygen atoms being preferred. The definition and specific examples of the above aromatic heterocyclic group are as described above, and a pyridine ring, pyridazine ring, or pyrazine ring is preferred.

[0050] In addition, in the above formula (N-11), X Ｎ２１ is -NR- and Y Ｎ２１ and Y Ｎ２２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ These may combine with each other to form a ring (hereinafter also simply referred to as "ring n11a"), X Ｎ２２ is -NR- and Y Ｎ２３ and Y Ｎ２４ At least one of them is = NR Ｗ１If so, R and R Ｗ１ The two may bond with each other to form a ring (hereinafter also simply referred to as "ring n11b"). Also, in the above formula (N-12), X Ｎ３１ is -NR- and Y Ｎ３１ and Y Ｎ３２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ These may combine with each other to form a ring (hereinafter also simply referred to as "ring n12a"), X Ｎ３２ is -NR- and Y Ｎ３３ and Y Ｎ３４ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ The two may bond with each other to form a ring (hereinafter also simply referred to as "ring n12b"). Also, in the above formula (N-13), X Ｎ４１ is -NR- and Y Ｎ４１ and Y Ｎ４２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ These may bond with each other to form a ring (hereinafter also simply referred to as "ring n13"). The rings n11a, n11b, n12a, n12b, and n13 are not particularly limited as long as they contain two nitrogen atoms, and may be either aromatic rings or non-aromatic rings, but aromatic rings are preferred. The number of members in the ring is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. In particular, in the above formula (N-11), R and R Ｗ１ When R and R are bonded to each other to form ring n11a and ring n11b, the compound represented by formula (N-11) is preferably the compound represented by formula (N-11n), where R and R Ｗ１ When R and R are bonded to each other to form a ring n12a, the compound represented by formula (N-12) is preferably the compound represented by formula (N-12n), where R and R Ｗ１ When these elements bond to each other to form rings n13a and n13b, the compound represented by formula (N-13) is preferably the compound represented by formula (N-13n).

[0051]

[0052] In formula (N-11n), Y Ｎ２２ , Y Ｎ２３ And m7 is Y in the above formula (N-11) Ｎ２２ , Y Ｎ２３ And is synonymous with m7, and the preferred embodiment is the same. In formula (N-12n), Y Ｎ３２ , Y Ｎ３３ And m8 is Y in the above formula (N-12) Ｎ３２ , Y Ｎ３３ And is synonymous with m8, and the preferred embodiment is the same. In formula (N-13n), Y Ｎ４１ And m9 is Y in the above formula (N-13). Ｎ４１ And is synonymous with m9, and the preferred embodiment is the same. In formulas (N-11n) to (N-13n), Z is synonymous with Z in the above formulas (N-11) to (N-13), and the preferred embodiment is the same. Ar ＸＹ This is Ar in the above formula (N-1n). ＸＹ This is synonymous with the above, and the preferred embodiments are the same, but among them, aromatic heterocycles are preferred, nitrogen-containing aromatic heterocycles are more preferred, and pyridine rings, pyridazine rings, or pyrazine rings are even more preferred.

[0053]

[0054] In equations (N-21) to (N-26), X is the same as X in equation (N-1) above. Ｎ１ This is synonymous with the above, and the preferred embodiment is also the same. In particular, in each of the above formulas (N-21) to (N-26), it is preferable that X is independently an oxygen atom or -NR-. R is synonymous with R in the above formula (N-1). Y is the same as Y in the above formula (N-1). Ｎ１ This is synonymous with the same as the preferred embodiment. In particular, in each of the above formulas (N-21) to (N-26), Y is independently an oxygen atom or =NR Ｗ１ It is preferable that this is the case. Ｗ１ This is R in the above formula (N-1). Ｗ１ This is equivalent to: Z is independently =CR Ｚ- represents a nitrogen atom. In each of the above formulas (N-21) to (N-26), the number of nitrogen atoms among the multiple Zs is preferably 2 or less, preferably 1 or less, and in each formula, Z is always = CR Ｚ - is preferable. R Ｚ This is R in the above equations (N-11) to (N-13). Ｚ This is synonymous with the same as the preferred embodiment. Also, both Zs are R Ｚ is a substituent = CR Ｚ - If R Ｚ The substituents represented by may bond to each other to form a ring. Specific examples and preferred embodiments of the above ring are those in formulas (N-11) to (N-13) where both Zs are equal to CR. Ｚ - If this is the case, R Ｚ This is the same as the specific examples and preferred embodiments of rings formed by the bonding of substituents represented by to one another.

[0055] Furthermore, in each of the above equations (N-21) to (N-26), X is -NR-, and at least one of the two Y adjacent to X is =NR. Ｗ１ If so, R and R Ｗ１ The two atoms may bond to each other to form a ring. The ring is not particularly limited as long as it contains two nitrogen atoms, and may be either an aromatic ring or a non-aromatic ring, but an aromatic ring is preferred. The number of members of the ring is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. In particular, in formulas (N-21) to (N-26), R and R Ｗ１ When the elements are bonded to each other to form a ring, each of the formulas (N-21) to (N-26) is preferably represented by the formulas (N-21n) to (N-26n) below.

[0056]

[0057] In formulas (N-21n) to (N-26n), Y and Z are the same as Y and Z in formulas (N-21) to (N-26) above, and the preferred embodiments are also the same. ＸＹ This is Ar in the above formula (N-1n). ＸＹhas the same definition and the same preferred embodiments; among these, an aromatic heterocyclic ring is preferred, a nitrogen-containing aromatic heterocyclic ring is more preferred, and a pyridine ring, a pyridazine ring, or a pyrazine ring is still more preferred.

[0058] Examples of compound N-1 include the compounds described in paragraphs

[0045] to

[0047] of Japanese Unexamined Patent Publication No. 2007-013123, the compounds described in paragraphs

[0094] to

[0105] of Japanese Unexamined Patent Publication No. 2020-188260, and the compounds described in paragraphs

[0154] to

[0156] of US Patent Application Publication No. 2024 / 0101565, the contents of which are incorporated herein by reference.

[0059] The molecular weight of compound N-1 is preferably 200 to 1,200, more preferably 200 to 900, and still more preferably 250 to 500.

[0060] The maximum absorption wavelength of compound N-1 is preferably in a wavelength range of 700 nm or less.

[0061] The photoelectric conversion film preferably has a bulk heterostructure formed in a state where compound N-1 and a compound represented by any one of formulas (1) to (3) are mixed. The bulk heterostructure is a layer in which compound N-1 and the compound represented by any one of formulas (1) to (3) are mixed and dispersed within the photoelectric conversion film. A 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 Japanese Unexamined Patent Publication No. 2005-303266.

[0062] The difference in electron affinity between compound N-1 and a compound represented by any one of formulas (1) to (3) is preferably 0.1 eV or more.

[0063] Compound N-1 may be used alone or in combination of two or more kinds. When the photoelectric conversion film contains compound N-1, the content of compound N-1 in the photoelectric conversion film (film thickness in terms of single layer of compound N-1 / film thickness of photoelectric conversion film × 100) is preferably 5 to 75% by volume, more preferably 10 to 50% by volume, and still more preferably 15 to 45% by volume.

[0064] For the effects of the present invention to be more superior, the content of compound N-1 relative to the total content of compound N-1 and any of the compounds represented by formulas (1) to (3) (film thickness of compound N-1 on a single-layer basis / (film thickness of compound N-1 on a single-layer basis + film thickness of any of the compounds represented by formulas (1) to (3) on a single-layer basis) × 100) is preferably 10 to 60 volume%, and more preferably 15 to 50 volume%. Furthermore, if the photoelectric conversion film further contains fullerenes selected from the group consisting of fullerenes and their derivatives, which will be described in detail later, the content of compound N-1 relative to the total content of compound N-1 and the fullerenes (film thickness of compound N-1 on a single-layer basis / (film thickness of compound N-1 on a single-layer basis + film thickness of the fullerenes on a single-layer basis) × 100) is preferably 5 to 90 volume%, and more preferably 5 to 60 volume%.

[0065] <Compounds represented by any of formulas (1) to (3)> Compounds represented by any of formulas (1) to (3) are often compounds having an absorption wavelength in the visible light region. In particular, it is preferable that the maximum absorption wavelength is in the visible light region, more preferably in the 400 to 700 nm range, and even more preferably in the 450 to 650 nm range. The above maximum absorption wavelength is the value measured in solution (solvent: chloroform) after adjusting the absorption spectrum of the dye to a concentration such that the absorbance is 0.5 to 1.0. However, if the dye does not dissolve in chloroform, the maximum absorption wavelength of the dye is measured using the dye in the form of a film after deposition.

[0066] The above photoelectric conversion film may contain at least one compound selected from the group consisting of compounds represented by any of formulas (1) to (3), but it is preferable to contain two or more compounds represented by any of formulas (1) to (3), more preferably two or three, and even more preferably two. Furthermore, the photoelectric conversion film preferably contains at least a compound represented by formula (1) or a compound represented by formula (2), and more preferably at least a compound represented by formula (1). In particular, in terms of achieving superior effects of the present invention, it is preferable that the above photoelectric conversion film contains two or more compounds represented by any of formulas (1) to (3), and further preferably at least one of them is one of compound 1A, compound 1B, and compound (2-1) described later. Formulas (1) to (3) will be described in detail below.

[0067] [Compound represented by formula (1)]

[0068]

[0069] In formula (1), D １１ Each of these independently represents a base that can be expressed by one of the formulas (D-1) to (D-3). １１ These are, independently, single bonds and -CR bonds. Ｂ =CR Ｂ R represents -, or -C≡C-. Ｂ Each of these independently represents a hydrogen atom or a substituent. １１ A represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, an optionally substituted aromatic ring group, a group represented by formula (A-1), or a group represented by formula (A-2). １２ represents the base represented by formula (A-1) or formula (A-2) above. n11 represents an integer from 0 to 2. In formula (D-1), k represents an integer from 0 to 4. A and C each independently represent a ring represented by formula (d1) or formula (d2). B each independently represents a ring represented by any of formulas (d3) to (d7). In formulas (d1) to (d7), Z １ａ Each of these is independently -CR Ａ = or represents a nitrogen atom. R ＡX represents a hydrogen atom or substituent. １ａ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents X ２ａ is an oxygen atom, a sulfur atom, or -NR Ａ１ Represents -. R Ａ１ ~R Ａ６ Each of these independently represents a hydrogen atom or a substituent. Ａ２ Allies, R Ａ３ Allies, R Ａ４ Allies, R Ａ５ Allies, and R Ａ６ Each of them may be bonded to each other to form a ring which may have substituents. ３ａ represents an oxygen atom or a sulfur atom. * represents a bond position. The rings represented by formulas (d1) and (d2) above are fused at the two fused ring positions represented by *1. The rings represented by formulas (d3) to (d7) above are fused with one adjacent ring at the two fused ring positions represented by *2, and with the other adjacent ring at the two fused ring positions represented by *3. In formula (D-2), Z １１ａ ~Z １６ａ Two of them represent -C(*) = and the other four are independently -CR Ａ = or represents a nitrogen atom. R Ａ represents a hydrogen atom or substituent. * represents a bond position. In formula (D-3), X １１ａ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents R Ａ１ ~R Ａ５ Each of these independently represents a hydrogen atom or a substituent.２１ａ ~Z ２４ａ Two of them represent -C(*) = and the other two independently represent -CR Ａ = or represents a nitrogen atom. R Ａ represents a hydrogen atom or substituent. * represents a bond position. In formula (A-1), R １１ ~R １３ Each of these independently represents a hydrogen atom or a substituent. m1 represents 0 or 1. C １１ This represents a ring containing two or more carbon atoms, which may have substituents. １ This consists of an oxygen atom, a sulfur atom, and =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ Represents R Ｗ１ R represents a hydrogen atom or substituent. Ｗ２ and R Ｗ３ These are, independently, a cyano group and a -COOR group. Ｗ４ , -COR Ｗ５ , or -SO ２ R Ｗ６ Represents R Ｗ４ ~R Ｗ６ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. * indicates the bond position. In formula (A-2), R １４ ~R １６ Each of these independently represents a hydrogen atom or a substituent. m2 represents 0 or 1. W ２ and W ３ These are, independently, a cyano group and a -COOR group. Ｗ１１ , -COR Ｗ１２ , -SOR Ｗ１３ , or -SO ２ R Ｗ１４ Represents R Ｗ１１ ~R Ｗ１４ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. * indicates the bond position.

[0070] The compound represented by formula (1) (hereinafter also referred to as "Specific Compound 1") will be described in detail below. In formula (1), D １１Each of these independently represents a base that can be expressed by one of the formulas (D-1) to (D-3). In particular, n¹¹+1 D １１ Preferably, at least one of them is a group represented by formula (D-1). １１ These are, independently, single bonds and -CR bonds. Ｂ =CR Ｂ - or -C≡C- represents a single bond, and R is preferred. Ｂ Each of these independently represents a hydrogen atom or a substituent, with hydrogen atoms being preferred. Ｂ Examples of substituents represented by the above-mentioned substituent W include the group exemplified above. １１ Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, an optionally substituted aromatic ring group, a group represented by formula (A-1), or a group represented by formula (A-2), with a hydrogen atom or a group represented by formula (A-1) being preferred, and a group represented by formula (A-1) being more preferred. １２ Each independently represents either the base represented by formula (A-1) or the base represented by formula (A-2), with the base represented by formula (A-1) being preferred. n11 represents an integer from 0 to 2, preferably 0 or 1, and more preferably 0. A １１ The number of carbon atoms in the alkyl group represented above may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1 to 6, and more preferably 1 to 3. １１The aromatic ring group represented above may be either an aromatic hydrocarbon ring group or an aromatic heterocyclic group. The aromatic ring group may be monocyclic or polycyclic, with monocyclic being preferred. The number of members in the aromatic ring group is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 6. The definition and specific examples of the aromatic hydrocarbon group are as described above. Examples of heteroatoms in the aromatic heterocyclic group include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron atoms, with nitrogen, sulfur, or oxygen atoms being preferred. The definition and specific examples of the aromatic heterocyclic group are as described above. Examples of substituents that the alkyl group and aromatic ring group may have include the substituent W described above, with alkyl groups, aryl groups, or halogen atoms being preferred.

[0071] In terms of achieving superior effects of the present invention, the specific compound 1 is preferably in one of the following embodiments: Embodiment 1: A １１ However, the group is represented by formula (A-1) or formula (A-2), n11+1 is 1 or 2, and n11 D １１ At least one of them is a group represented by formula (D-2) or a group represented by formula (D-3). Embodiment 2: A １１ The group is represented by formula (A-1) or formula (A-2), and n¹¹ + 1 D １１ At least one of them is a group represented by formula (D-1). Embodiment 3: A １１ These are hydrogen atoms, and n¹¹+1 D １１ At least one of these is a group represented by formula (D-1). When specific compound 1 is embodiment 2 or embodiment 3, it is also preferable that n11 is 1. Furthermore, it is also preferable that n11 is 0, in which case specific compound 1 is more preferably embodiment 4 or embodiment 5 below. Embodiment 4: A １１ is a group represented by formula (A-1) or formula (A-2), n11 is 0, and D １１ However, it is a base represented by formula (D-1). Appearance 5: A １１ is a hydrogen atom, n11 is 0, and D １１However, this is the base represented by formula (D-1).

[0072] In particular, in terms of the superior effects of the present invention, the specific compound is A in formula (1). １１ is a group represented by the above formula (A-1) or the above formula (A-2), n11 is 0, and D １１ Compound 1A is a group represented by the above formula (D-1), or in formula (1), A １１ is a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, or an optionally substituted aromatic ring group, and n11 is 0, D １１ It is preferable that the compound is compound 1B, and more preferably compound 1A, where the group is represented by the above formula (D-1).

[0073] The bases represented by formulas (D-1) to (D-3), formula (A-1), and formula (A-2) will be described in detail below.

[0074] In formula (D-1), k represents an integer from 0 to 4, and an integer from 0 to 2 is preferred in that the effects of the present invention are superior. Also, if the photoelectric conversion film is D １ When the compound contains two or more compounds represented by formula (1) above, the group represented by formula (D-1) described later is preferably different from each other, preferably the k value of at least one of the two or more compounds is 3, and more preferably the k value of one is 3 and the k value of the other is 2 or 4.

[0075] In formula (D-1), A and C each independently represent a ring represented by formula (d1) or formula (d2). B each independently represents a ring represented by any of formulas (d3) to (d7). For B, the ring represented by formula (d3) or formula (d4) is preferred, and the ring represented by formula (d4) is more preferred. In formula (D-1), adjacent rings represented by A to C are fused at the fused ring positions indicated by *1 to *3 in formulas (d1) to (d7), which will be described later. That is, the group represented by formula (D-1) is a divalent fused ring group consisting of rings represented by A, k B, and C. For example, when k=0, A and C are fused; when k=1, A and B, and B and C are fused; and when k=2, A and B, two adjacent Bs, and B and C are fused.

[0076] In formulas (d1) to (d7), Z １ａ Each of these is independently -CR Ａ = or represents a nitrogen atom. R Ａ R represents a hydrogen atom or substituent. Ａ Examples of substituents represented by include the substituent W described above, and preferably are an aliphatic hydrocarbon group which may have substituents, an aromatic ring group which may have substituents, an aliphatic heterocyclic group which may have substituents, an alkoxy group, an aryloxy group, an acyl group, a silyl group, a halogen atom, a cyano group, or a nitro group, and more preferably an aliphatic hydrocarbon group which may have substituents, an aromatic ring group which may have substituents, an aliphatic heterocyclic group which may have substituents, a silyl group, an alkoxy group, or a halogen atom. Examples of substituents which each of the above-mentioned groups which may have substituents include the substituents exemplified by substituent W described above, and substituents selected from the substituent group S described later are preferred.

[0077] The above aliphatic hydrocarbon group may be linear, branched, or cyclic. Examples of the above aliphatic hydrocarbon group include alkyl groups, alkenyl groups, and alkynyl groups, with alkyl groups being preferred. The number of carbon atoms in a linear aliphatic hydrocarbon group is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 4, and particularly preferably 1 or 2. The number of carbon atoms in a branched aliphatic hydrocarbon group is preferably 3 to 20, more preferably 3 to 10, even more preferably 3 to 7, and particularly preferably 3 to 5. The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. The number of carbon atoms in a cyclic aliphatic hydrocarbon group is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 6.

[0078] The above aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group. The above aromatic ring group may be monocyclic or polycyclic, with monocyclic being preferred. The number of ring member atoms of the above aromatic ring group is preferably 5 to 18, more preferably 5 to 10, and even more preferably 5 to 8. The definition and specific examples of an aromatic hydrocarbon group are as described above, with a phenyl group or a naphthyl group being preferred, and a phenyl group being more preferred. Examples of heteroatoms that the above aromatic heterocyclic group may have are as described above, with sulfur atoms, oxygen atoms, or nitrogen atoms being preferred. The definition and specific examples of an aromatic heterocyclic group are as described above, with a thiophene ring group, a furan ring group, a pyrrole ring, a thiazole ring, or a pyridine ring group being preferred. The above aromatic ring group may have substituents as described above. If the above aromatic ring group has substituents, the number is not particularly limited, but 1 to 3 is preferred.

[0079] The above aliphatic heterocyclic group may be monocyclic or polycyclic, with monocyclic being preferred. The number of ring member atoms of the above aliphatic heterocyclic group is preferably 3 to 18, more preferably 5 to 10, and even more preferably 5 to 8. Examples of heteroatoms of the above aliphatic heterocyclic group are as described above, with sulfur atoms, oxygen atoms, or nitrogen atoms being preferred. The definition and specific examples of the aliphatic heterocyclic group are as described above, with thiolane ring groups, piperidine ring groups, tetrahydrofuran ring groups, or tetrahydropyran ring groups being preferred. As described above, the above aliphatic heterocyclic group may have substituents. If the above aliphatic heterocyclic group has substituents, the number is not particularly limited, but 1 to 3 is preferred.

[0080] The alkyl group of the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 5, and particularly preferably 1 to 3.

[0081] The aryl group in the above aryloxy group may be monocyclic or polycyclic, with monocyclic being preferred. The number of carbon atoms in the above aryloxy group is preferably 5 to 18, more preferably 6 to 10, and even more preferably 6 to 8.

[0082] The hydrocarbon group of the above acyl group may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred. Preferred embodiments of the aliphatic hydrocarbon group and aromatic hydrocarbon group of the above acyl group are R Ａ The substituents represented are the same as those exemplified. The number of carbon atoms in the above acyl group is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0083] The above silyl group is -SiR Ｓｉ ３ It is a group represented by R. Ｓｉ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. Ｓｉ The definitions and preferred embodiments of each group exemplified as a substituent represented by R ＡThese are the same groups as the substituents exemplified by the formulas.

[0084] Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred.

[0085] In formulas (d1) to (d7), X １ａ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ )- represents, and in terms of the superior effect of the present invention, oxygen atom, sulfur atom, -NR Ａ１ -, -SiR Ａ２ ２ - or -CR Ａ４ ２ - Preferably an oxygen atom, a sulfur atom, -NR Ａ１ - or -CR Ａ４ ２ This is more preferable. In particular, the present invention is more effective in that at least one of the k B groups is a group represented by formula (d4), and X １ａ ga-NR Ａ１ - or -CR Ａ４ ２ It is preferable that this is the case. ２ａ is an oxygen atom, a sulfur atom, or -NR Ａ１ Represents -. X ３ａ R represents an oxygen atom or a sulfur atom. Ａ１ ~R Ａ６ Each of these independently represents a hydrogen atom or a substituent. Ａ１ ~R Ａ６ The substituents represented by the above-mentioned substituent W include the substituents exemplified above, and preferably are an aliphatic hydrocarbon group which may have substituents, an aromatic ring group which may have substituents, or an aliphatic heterocyclic group which may have substituents, more preferably an aliphatic hydrocarbon group which may have substituents or an aromatic ring group which may have substituents, and even more preferably an aliphatic hydrocarbon group which may have substituents. Ａ１ ~RＡ６ The definitions and preferred embodiments of each group exemplified as substituents represented by the above R Ａ The substituents represented are the same as those exemplified, but among them, aliphatic hydrocarbon groups having 1 to 3 carbon atoms are preferred, and aliphatic hydrocarbon groups having 1 or 2 carbon atoms are more preferred.

[0086] R Ａ２ Allies, R Ａ３ Allies, R Ａ４ Allies, R Ａ５ , and R Ａ６ These elements may be bonded to each other to form a ring which may have substituents. That is, R Ａ２ They may be bonded to each other to form a ring which may have substituents, R Ａ３ They may be bonded to each other to form a ring which may have substituents, R Ａ４ They may be bonded to each other to form a ring which may have substituents, R Ａ５ They may be bonded to each other to form a ring which may have substituents, R Ａ６ The elements may be bonded to each other to form a ring which may have substituents. The ring may be either an aromatic ring or an aliphatic ring, with an aliphatic ring being preferred. The ring may be either a monocyclic or polycyclic ring. The number of ring member atoms in the ring is preferably 3 to 20, more preferably 5 to 12, and even more preferably 5 to 10. The ring may have heteroatoms. The heteroatoms are preferably sulfur atoms, nitrogen atoms, or oxygen atoms. The substituents that the ring may have include the substituent W mentioned above, and alkyl groups, aryl groups, or halogen atoms are preferred.

[0087] In equations (d1) to (d7), * represents a bond position. The bond positions represented by * in equations (d1) to (d7) correspond to the bond positions represented by * in equation (D-1). The rings represented in equations (d1) and (d2) are fused at the two fused ring positions represented by *1. The rings represented in equations (d3) to (d7) are fused with one adjacent ring at the two fused ring positions represented by *2, and with the other adjacent ring at the two fused ring positions represented by *3. For example, if A is a group represented by formula (d1), k is 1, B is a group represented by formula (d3), and C is a group represented by formula (d2), then A and B are fused at the fused ring position represented by *1 in formula (d1) and the fused ring position represented by *2 in formula (d3), and B and C are fused at the fused ring position represented by *3 in formula (d3) and the fused ring position represented by *1 in formula (d2), or A and B are fused at the fused ring position represented by *1 in formula (d1) and the fused ring position represented by *3 in formula (d3), and B and C are fused at the fused ring position represented by *2 in formula (d3) and the fused ring position represented by *1 in formula (d2).

[0088] In formula (D-2), Z １１ａ ~Z １６ａ Two of them represent -C(*) = and the other four are independently -CR Ａ = or represents a nitrogen atom. In particular, Z １１ａ ~Z １６ａ Two of them represent -C(*) = and the other four are independently -CR Ａ It is preferable to represent it as =. R Ａ R represents a hydrogen atom or substituent. Ａ This is as described above in equation (D-1).

[0089] In formula (D-3), X １１ａ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ )- represents the effect of the present invention, and in terms of superiority, oxygen atoms, sulfur atoms, or -NRＡ１ - is preferred, and an oxygen atom or a sulfur atom is more preferred. ２１ａ ~Z ２４ａ Two of them represent -C(*) = and the other two independently represent -CR Ａ = or represents a nitrogen atom. R Ａ１ ~R Ａ５ Each of these independently represents a hydrogen atom or a substituent. Ａ R represents a hydrogen atom or substituent. Ａ and R Ａ１ ~R Ａ５ This is as described above in equation (D-1).

[0090] The group represented by formula (D-1) is preferably a group represented by any of formulas (B1) to (B17), more preferably a group represented by any of formulas (B2) to (B6), (B8), (B10), (B12) to (B14), (B16), and (B17), and even more preferably a group represented by any of formulas (B3) to (B6), (B8), (B10), (B12) to (B14), and (B16). The group represented by formula (D-2) is preferably a group represented by any of formulas (A1) to (A3), more preferably a group represented by formula (A1) or (A2), and even more preferably a group represented by formula (A1). The group represented by formula (D-3) is preferably a group represented by formula (A4).

[0091]

[0092]

[0093] In the above formulas (A1) to (A4) and (B1) to (B17), Z is independently -CR Ａ = or represents a nitrogen atom, -CR Ａ = is preferable. X is independently an oxygen atom, a sulfur atom, a selenium atom, or -NR Ａ１ - represents an oxygen atom, a sulfur atom, or -NR Ａ１ - is preferred, and an oxygen atom or a sulfur atom is more preferred. Ｉ These are, independently, an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) - represents oxygen atom, sulfur atom, -NR Ａ１ -, -SiR Ａ２ ２ - or -CR Ａ４ ２ - is preferable. R Ａ and R Ａ１ ~R Ａ５ As described above in equation (D-1). Also, R Ａ２ Allies, R Ａ３ Allies, R Ａ４ Allies, and R Ａ５ These elements may be bonded to each other to form a ring which may have substituents. Details of the ring which may have substituents are as described above in formula (D-1).

[0094]

[0095] In formula (A-1), R １１ ~R １３ Each of these independently represents a hydrogen atom or a substituent, with hydrogen atoms being preferred. １１ ~R １３ Examples of substituents represented by the above-mentioned substituent W include the substituents exemplified by substituent W.

[0096] In formula (A-1), m1 represents 0 or 1, and 0 is preferred in that the effects of the present invention are superior.

[0097] In formula (A-1), C １１ C represents a ring containing two or more carbon atoms, which may have substituents. １１The two carbon atoms included are the two carbon atoms explicitly shown in formula (A-1). The number of carbon atoms in the above 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 above ring is the number including the two carbon atoms explicitly shown in the formula. The above ring may be either an aromatic ring or an aliphatic ring. The above ring may be either a monocyclic or polycyclic ring, and 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 is preferred. 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 above ring may have heteroatoms. Examples of the above heteroatoms include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron, with sulfur, nitrogen, or oxygen being preferred. The number of heteroatoms in the above ring is preferably 0 to 10, and more preferably 0 to 5. １１ Among the carbon atoms constituting the ring represented by (A-1), carbon atoms other than those explicitly shown in formula (A-1) may be substituted with carbonyl carbons (>C=O) and thiocarbonyl carbons (>C=S), etc.

[0098] Examples of substituents that the above ring may have include the group exemplified by substituent W, and preferably a halogen atom, an optionally substituted alkyl group, an optionally substituted aromatic ring group, or a silyl group, more preferably a halogen atom or an alkyl group, and even more preferably an alkyl group. The alkyl group may be linear, branched, or cyclic, and linear is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 3, and even more preferably 1 or 2. Preferred substituents that the alkyl group may have include a halogen atom, an aromatic ring group, or a silyl group. Preferred substituents that the aromatic ring group may have include a halogen atom, an alkyl group, or a silyl group.

[0099] In formula (A-1), W １ This consists of an oxygen atom, a sulfur atom, and =NR Ｗ１ , or =CR Ｗ２ R Ｗ３In terms of exhibiting superior effects of the present invention, an oxygen atom or a sulfur atom is preferred, and an oxygen atom is more preferred. Ｗ１ R represents a hydrogen atom or substituent. Ｗ１ Examples of substituents represented by the above-mentioned substituent W include R. Ｗ２ and R Ｗ３ These are, independently, a cyano group and a -COOR group. Ｗ４ , -COR Ｗ５ , or -SO ２ R Ｗ６ Represents R Ｗ４ ~R Ｗ６ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. The definition of an aliphatic hydrocarbon group is as described above, and an aliphatic hydrocarbon group having 1 to 4 carbon atoms is preferred. The definition of an aromatic ring group is as described above, and an aromatic hydrocarbon group is preferred, with a phenyl group being more preferred. The definition of an aliphatic heterocyclic group is as described above, and the heteroatom of the above aliphatic heterocyclic group is preferably a sulfur atom, an oxygen atom, or a nitrogen atom. Ｗ４ ~R Ｗ６ Examples of substituents that each group represented by the above-mentioned substituent W may have include alkyl groups, alkoxy groups, aromatic ring groups, or halogen atoms.

[0100] C １１The rings represented by are preferably rings used as acidic nuclei (for example, acidic nuclei of merocyanine dyes), and examples of nuclei include the following: (a) 1,3-dicarbonyl nuclei: for example, 1,3-indanedione nuclei, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, and 1,3-dioxane-4,6-dione. (b) Pyrazolinone nuclei: 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 nuclei: for example, 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one. (d) Oxindole nuclei: for example, 1-alkyl-2,3-dihydro-2-oxindole. (e) 2,4,6-trioxohexahydropyrimidine core: for example, barbituric acid, 2-thiobarbituric acid, and its derivatives. Examples of the above 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 core: for example, rhodanine and its derivatives. Examples of the above 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 core (2-thio-2,4-(3H,5H)-oxazoledione core): For example, 3-ethyl-2-thio-2,4-oxazolidinedione. (h) thianaphthenone core: For example, 3(2H)-thianaphthenone-1,1-dioxide. (i) 2-thio-2,5-thiazolidinedione core: For example, 3-ethyl-2-thio-2,5-thiazolidinedione.(j) 2,4-thiazolidinedione nuclei: e.g., 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione, etc. (k) thiazolin-4-one nuclei: e.g., 4-thiazolinone and 2-ethyl-4-thiazolinone, etc. (l) 2,4-imidazolidinedione (hydantoin) nuclei: e.g., 2,4-imidazolidinedione and 3-ethyl-2,4-imidazolidinedione, etc. (m) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nuclei: e.g., 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidinedione, etc. (n) Imidazolin-5-one core: e.g., 2-propylmercapto-2-imidazolin-5-one. (o) 3,5-pyrazolidinedione core: e.g., 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione. (p) Benzothiophen-3(2H)-one core: e.g., benzothiophen-3(2H)-one, oxobenzothiophen-3(2H)-one, and dioxobenzothiophen-3(2H)-one. (q) Indanone core: e.g., 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone, and 3,3-dimethyl-1-indanone. (r) Benzofuran-3-(2H)-one nucleus: e.g., benzofuran-3-(2H)-one. (s) 2,2-dihydrophenalen-1,3-dione nucleus, etc.

[0101] The group represented by formula (A-1) is preferred over the group represented by formula (A-11) in that it exhibits superior effects of the present invention.

[0102]

[0103] In formula (A-11), R １１ ~R １３ and m1 are, respectively, R in equation (A-1) １１ ~R １３ And it is the same as m1.

[0104] In formula (A-11), C １２ This represents a ring containing at least three carbon atoms, which may have substituents. １２The three carbon atoms included are the three carbon atoms explicitly shown in formula (A-11). The number of carbon atoms in the above 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 above ring is the number including the three carbon atoms explicitly shown in the formula. The above ring may be either an aromatic ring or an aliphatic ring. The above ring may be either a monocyclic or polycyclic ring, and 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 is preferred. 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 above ring may have heteroatoms. Examples of the above heteroatoms include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron, with sulfur, nitrogen, or oxygen being preferred. The number of heteroatoms in the above ring is preferably 0 to 10, and more preferably 0 to 5. The above CC １２ Of the carbon atoms constituting the ring represented by (A-11), carbon atoms other than those explicitly shown in formula (A-11) may be substituted with carbonyl carbons (>C=O) and thiocarbonyl carbons (>C=S), etc. Preferred embodiments of substituents that the above ring may have are the above-mentioned ring C １２ This is similar to the substituents that may be present.

[0105] In formula (A-11), W １１ and W １２ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ In terms of exhibiting superior effects of the present invention, an oxygen atom or a sulfur atom is preferred, and an oxygen atom is more preferred. Ｗ１ ~R Ｗ３ This is as described above in equation (A-1).

[0106] The group represented by formula (A-1) is more preferably the group represented by formula (A-12) or the group represented by formula (A-13).

[0107]

[0108] In equations (A-12) and (A-13), R １１~R １３ and m1 are, respectively, R in equation (A-1) １１ ~R １３ And it is the same as m1.

[0109] In formula (A-12), X ｃ１ and X ｃ２ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ In terms of exhibiting superior effects of the present invention, an oxygen atom or a sulfur atom is preferred, and an oxygen atom is more preferred. Ｗ１ ~R Ｗ３ As described above in formula (A-1). In terms of the superior effects of the present invention, X ｃ１ and X ｃ２ Preferably, one of them is an oxygen atom, X ｃ１ and X ｃ２ It is more preferable that it be an oxygen atom.

[0110] In formula (A-12), C １３ represents an aromatic ring which may have substituents. The aromatic ring may be monocyclic or polycyclic. The number of member atoms of the aromatic ring is preferably 4 to 30, more preferably 5 to 12, and even more preferably 5 to 8. The number of member atoms of the aromatic ring is the number including the two carbon atoms explicitly shown in the formula. The aromatic ring may also be an aromatic hydrocarbon ring or an aromatic heterocyclic ring, with an aromatic hydrocarbon ring being preferred. Specific examples of the aromatic ring are as described above, and are preferably a benzene ring, naphthalene ring, anthracene ring, pyrene ring, thiophene ring, furan ring, thiazole ring, oxazole ring, pyridine ring, thienothiophene cyclic ring, benzothiophene ring, benzofuran ring, pyrazine ring, pyrimidine ring, or pyridazine ring, more preferably a benzene ring, naphthalene ring, or thiophene ring, and even more preferably a benzene ring. Examples of substituents which the aromatic ring may have include the group exemplified by substituent W, and alkyl groups or halogen atoms are preferred. The number of substituents that the above aromatic ring may have is not particularly limited, but is preferably 0 to 8, and more preferably 0 to 4.

[0111] In formula (A-13), Xｃ３ ~X ｃ５ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ In terms of exhibiting superior effects of the present invention, an oxygen atom or a sulfur atom is preferred, and an oxygen atom is more preferred. Ｗ１ ~R Ｗ３ As described above in formula (A-1). In terms of the superior effects of the present invention, X ｃ３ and X ｃ４ It is preferable that X is an oxygen atom. ｃ３ ~X ｃ５ It is more preferable that it be an oxygen atom.

[0112] In formula (A-13), Z ｃ１ and Z ｃ２ Each of these is independently -NR ｃ１ - or -CR ｃ２ ２ - indicates that the effects of the present invention are superior, and -NR ｃ１ - is preferable. R ｃ１ and R ｃ２ Each of these independently represents a hydrogen atom or a substituent. Examples of the substituent include the group exemplified by substituent W, and alkyl groups or aryl groups are preferred, with alkyl groups being more preferred. The alkyl group may be linear, branched, or cyclic, with linear being preferred. The number of carbon atoms in the alkyl group is preferably 1 to 20, 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 phenyl groups being preferred. The aryl group may have further substituents, and examples of substituents include the group exemplified by substituent W.

[0113] In formula (A-2), R １４ ~R １６ Each of these independently represents a hydrogen atom or a substituent, with hydrogen atoms being preferred. １４ ~R １６ Examples of substituents represented by the above-mentioned substituent W include the substituents exemplified by substituent W.

[0114] In formula (A-2), m² represents 0 or 1, and 0 is preferred in that the effects of the present invention are superior.

[0115] In formula (A-2), W ２ and W ３ These are, independently, a cyano group and a -COOR group. Ｗ１１ , -COR Ｗ１２ , -SOR Ｗ１３ , or -SO ２ R Ｗ１４ Represents R Ｗ１１ ~R Ｗ１４ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. Ｗ１１ ~R Ｗ１４ The definitions and preferred embodiments of each group represented by formula (A-1) are as follows: Ｗ４ ~R Ｗ６ Each of the groups represented is the same as R. Ｗ１１ ~R Ｗ１４ Among these, aliphatic hydrocarbon groups or phenyl groups having 1 to 4 carbon atoms are preferred.

[0116] The substituent group S is described in detail below. Substituent group S: linear aliphatic hydrocarbon groups having 1 to 3 carbon atoms, branched aliphatic hydrocarbon groups having 3 to 7 carbon atoms, cyclic aliphatic hydrocarbon groups having 3 to 6 carbon atoms, aromatic ring groups having 5 to 12 ring member atoms which may have substituents, alkoxy groups having 1 to 5 carbon atoms, acyl groups having 2 to 6 carbon atoms, silyl groups, and halogen atoms.

[0117] The number of carbon atoms in the linear aliphatic hydrocarbon group in the substituent group S is 1 to 3, more preferably 1 or 2. The number of carbon atoms in the branched aliphatic hydrocarbon group in the substituent group S is 3 to 7, more preferably 3 or 4. The cyclic aliphatic hydrocarbon group in the substituent group S is preferably monocyclic.

[0118] The aromatic ring group in the substituent group S may be monocyclic or polycyclic, with monocyclic being preferred. The aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group, with aromatic hydrocarbon groups being preferred. The heteroatoms of the aromatic heterocyclic group are preferably oxygen atoms, nitrogen atoms, or sulfur atoms. The number of ring member atoms of the aromatic ring group is 5 to 12, preferably 5 to 10, and more preferably 5 or 6. Examples of substituents that the aromatic ring group may have are the substituents exemplified by substituent W described above, with substituents selected from substituent group S being preferred, and more preferably linear aliphatic hydrocarbon groups having 1 to 3 carbon atoms, branched aliphatic hydrocarbon groups having 3 to 7 carbon atoms, silyl groups, alkoxy groups having 1 to 5 carbon atoms, or halogen atoms. If the aromatic ring group has substituents, the number of substituents is preferably 1 to 3.

[0119] The number of carbon atoms in the alkoxy group in the above substituent group S is 1 to 5, more preferably 1 to 4, and even more preferably 1 or 2. The number of carbon atoms in the acyl group in the above substituent group S is 2 to 6, more preferably 2 to 5, and even more preferably 2 or 3.

[0120] The definition and preferred embodiment of the silyl group in the above substituent group S is as described above in R Ａ The substituent represented by is the same as the silyl group exemplified. In particular, R Ｓｉ However, each is independently a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 7 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 6 carbon atoms, or an aromatic ring group having 5 to 12 ring member atoms, which may have substituents, -SiR Ｓｉ ３ A base represented by is preferred.

[0121] Examples of halogen atoms in the above substituent group S include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred.

[0122] A １１ Specific examples of specific compound 1, in which is a group represented by formula (A-1) or a group represented by formula (A-2), include the following compounds.

[0123]

[0124] A １１ The following are specific examples of specific compound 1 when the group is not represented by formula (A-1) or formula (A-2).

[0125]

[0126]

[0127] A above １１ In specific examples of compound 1, A is not a group represented by formula (A-1) or a group represented by formula (A-2). １１ This represents a hydrogen atom, a halogen atom, a cyano group, or a group represented as follows:

[0128]

[0129] In the above compound examples, R independently represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-propyl group, a neopentyl group, an n-hexyl group, a 2-ethylhexyl group, a phenyl group, a 2,6-dimethylphenyl group, a 2,6-diisopropylphenyl group, a fluorine atom, a chlorine atom, or a cyano group. X and X Ｉ These are X and X in equations (A1) to (A4) and equations (B1) to (B17), respectively. Ｉ It is the same as above. Each A independently represents one of the following groups. Note that Ph represents a phenyl group and Me represents a methyl group.

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] A １１Specific examples of specific compound 1 when is not a group represented by formula (A-1) or formula (A-2) include the compounds described in brochures WO2025 / 052923, WO2025 / 164513, WO2025 / 164330, and WO2025 / 192225.

[0136] A １１ Specific examples of specific compound 1 when is a group represented by formula (A-1) or formula (A-2) include WO2023 / 171788, WO2023 / 210772, WO2023 / 219042, WO2023 / 219033, WO2023 / 218933, WO2024 / 062871, and WO2024 / 071143. Brochures, WO2024 / 071188, WO2024 / 135443, WO2024 / 122301, WO2024 / 224979, WO2024 / 185744, WO2024 / 185467, WO2024 / 185812, WO2024 / 185418, WO2024 / 185810 Brochures, WO2024 / 202762, WO2024 / 203704, WO2024 / 262173, WO2024 / 262179, WO2025 / 069836, WO2025 / 028340, WO2025 / 063058, WO2025 / 063074, WO2024 / 262486 Examples of compounds described in the brochure, WO2024 / 262437, WO2025 / 041541, WO2025 / 041538, WO2025 / 169686, WO2025 / 142297, WO2025 / 204627, WO2025 / 253926, and WO2025 / 258354.

[0137] Specific examples of specific compound 2 include the compounds described in Japanese Patent Publication No. 2023-118497, Japanese Patent Publication No. 2023-113357, Brochure WO2024 / 203386, Brochure WO2025 / 033197, and Brochure WO2025 / 192257.

[0138] [Compound represented by formula (2)] Next, we will describe in detail the compound represented by formula (2).

[0139]

[0140] In formula (2), R ２１ represents a hydrogen atom or substituent. A ２１ Ar represents the group represented by the above formula (A-1) or the group represented by the above formula (A-2). ２１ R represents an aromatic ring group which may have substituents. ２２ This is an aryl group which may have a substituent, -C(R Ｌ１ ) (Caution Ｌ２ ) (Caution Ｌ３ R represents a heteroaryl group which may have substituents. Ｌ１ ~R Ｌ３ Each independently represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, or a hydrogen atom, R Ｌ１ ~R Ｌ３ Of these, at least two independently represent an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. Ｌ１ ~R Ｌ３ The optionally substituted alkyl group, optionally substituted aryl group, and optionally substituted heteroaryl group represented by the above may be bonded to each other via single bonds or divalent linking groups to form an optionally substituted ring. ２１ -NR １ｓ -, -CR ２ｓ ２ - represents a sulfur atom, oxygen atom, or selenium atom. １ｓ and R ２ｓEach of these independently represents a substituent. ２ｓ These elements may be bonded to each other to form a ring that may have substituents.

[0141] In formula (2), R ２１ R represents a hydrogen atom or a substituent, with a hydrogen atom being preferred. ２１ Examples of substituents represented by the above-mentioned substituent W include the substituents exemplified by substituent W.

[0142] In formula (2), A ２１ This represents the group represented by formula (A-1) or the group represented by formula (A-2). Details of the group represented by formula (A-1) and the group represented by formula (A-2) are as described above in formula (1).

[0143] In formula (2), Ar ２１ represents an aromatic ring which may have substituents. The aromatic ring may be monocyclic or polycyclic, and polycyclic is preferred in that it provides superior effects of the present invention. The number of ring fusions of the polycyclic is preferably 2 to 4, and more preferably 2. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic, and an aromatic heterocyclic is preferred. Examples of heteroatoms of the aromatic heterocyclic are as described above, and oxygen, nitrogen, or sulfur atoms are preferred, with nitrogen atoms being more preferred. The number of ring member atoms of the aromatic ring group is preferably 5 to 20, more preferably 6 to 14, and even more preferably 8 to 10. Among the aromatic rings, polycyclic rings including nitrogen-containing aromatic rings are preferred. Examples of substituents that the aromatic ring may have include the substituent W described above, and preferably a substituted aliphatic hydrocarbon group, a substituted aromatic ring group, a substituted aliphatic heterocyclic group, a substituted alkoxy group, a halogen atom, a silyl group, or a cyano group, and more preferably a substituted aliphatic hydrocarbon group, a substituted alkoxy group, or a halogen atom. The definitions and preferred embodiments of each of the groups exemplified as substituents are described above in R. Ａ These are the same groups as the substituents exemplified by the formulas.

[0144] In formula (2), R ２２This is an aryl group which may have a substituent, -C(R Ｌ１ ) (Caution Ｌ２ ) (Caution Ｌ３ ), or a heteroaryl group which may have a substituent, and an aryl group which may have a substituent or -C (R Ｌ１ ) (Caution Ｌ２ ) (Caution Ｌ３ ) is preferred, and a substituted aryl group is more preferred.

[0145] R ２２ The aryl group represented by may be monocyclic or polycyclic. The number of carbon atoms in the aryl group is preferably 6 to 12, more preferably 6 to 10. The aryl group is preferably a phenyl group, naphthyl group, anthryl group, or fluorenyl group, more preferably a phenyl group. The substituent that the aryl group may have is the substituent W mentioned above, which is preferably an alkyl group, an aryl group which may have a substituent, an aryl group which may have a substituent, a cyano group, an alkoxy group, or a halogen atom, more preferably an alkyl group, an aryl group which may have an alkyl group, or a halogen atom, and even more preferably a phenyl group which may have an alkyl group or an alkyl group having 2 or more carbon atoms. The alkyl group exemplified as a substituent that the aryl group may have may be linear, branched, or cyclic, and is preferably branched in that it provides better effects of the present invention. The number of carbon atoms in the alkyl group is preferably 2 or more in that it provides better effects of the present invention. The upper limit is preferably 8 or less, more preferably 6 or less, and even more preferably 4 or less. The number of substituents on the aryl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 2 or 3.

[0146] -C(R Ｌ１ ) (Caution Ｌ２ ) (Caution Ｌ３ ) Medium, R Ｌ１ ~R Ｌ３ Each independently represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, or a hydrogen atom, R Ｌ１ ~R Ｌ３Of these, at least two independently represent an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. Examples of substituents that each of the above groups may have include the substituent W described above, and alkyl groups, aryl groups, or halogen atoms are preferred. Ｌ１１ ~R Ｌ１３ The alkyl group represented by may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1 to 6, and more preferably 1 to 3. Ｌ１１ ~R Ｌ１３ The definitions and preferred embodiments of the aryl group and heteroaryl group represented by R ２２ These are the same as the aryl and heteroaryl groups represented by .

[0147] R Ｌ１１ ~R Ｌ１３ The optionally substituted alkyl group, optionally substituted aryl group, and optionally substituted heteroaryl group represented by may be bonded to each other via single bonds or divalent linking groups to form a ring. For example, R Ｌ１１ and R Ｌ１２ Alkyl groups that may have substituents represented by R may be bonded to each other via single bonds or divalent linking groups to form a ring that may have substituents, Ｌ１１ An aryl group which may have a substituent represented by R Ｌ１２ An alkyl group which may have substituents represented by can be bonded to each other via a single bond or a divalent linking group to form a ring which may have substituents. Examples of divalent linking groups include a divalent hydrocarbon group (e.g., an alkylene group or an arylene group), -O-, -CO-, -SO ２Examples include -, -NH-, and groups formed by combining these. The ring is preferably an aliphatic ring. The number of ring member atoms in the ring is preferably 3 to 20, more preferably 3 to 12, and even more preferably 3 to 6. The ring may have heteroatoms. Examples of heteroatoms include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron atoms, with sulfur, nitrogen, or oxygen atoms being preferred. Substituents that the ring may have include the substituent W mentioned above, with alkyl groups, aryl groups, or halogen atoms being preferred.

[0148] R ２２ The heteroaryl group represented by may be monocyclic or polycyclic. Examples of heteroatoms of the heteroaryl group are as described above, with nitrogen, sulfur, or oxygen atoms being preferred. The number of ring member atoms of the heteroaryl group is preferably 5 to 20, and more preferably 5 to 12. The definitions and preferred embodiments of substituents that the heteroaryl group may have are given above. ２２ The definition of substituents that the aryl group represented by may have and preferred embodiments are the same as those defined above.

[0149] In formula (2), X ２１ -NR １ｓ -, -CR ２ｓ ２ - represents a sulfur atom, an oxygen atom, or a selenium atom, and -NR is used in terms of having superior effects of the present invention. １ｓ - or -CR ２ｓ ２ - is preferable. R １ｓ and R ２ｓ Each of these independently represents a hydrogen atom or a substituent. １ｓ Examples of substituents represented by include the substituent W mentioned above, and may have substituents, such as an aryl group, -C(R Ｌ１ ) (Caution Ｌ２ ) (Caution Ｌ３ A heteroaryl group, which may have substituents, is preferred. １ｓ The definitions and preferred embodiments of each group exemplified as substituents represented by the above R ２２ It is the same as the group represented by R. ２ｓThe substituents represented are preferably an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group, with an optionally substituted aliphatic hydrocarbon group being more preferred. ２ｓ The definitions and preferred embodiments of each group exemplified as substituents represented by the above R Ａ１ ~R Ａ６ These are the same groups as the substituents exemplified by the formulas.

[0150] R ２ｓ These elements may be bonded to each other to form a ring that may have substituents. ２ｓ A preferred embodiment of the ring, which may have substituents that may be formed by bonding with each other, is the R described above. Ａ２ Allies, R Ａ３ Allies, R Ａ４ Allies, R Ａ５ Allies, and R Ａ６ This is the same as a ring which may have substituents that can be formed by bonding with each other.

[0151] Of the compounds represented by formula (2), the compound represented by formula (2-1) is preferred.

[0152]

[0153] In formula (2-1), R ２１ , R ２２ A ２１ , and X ２１ These are R in equation (2), respectively. ２１ , R ２２ A ２１ , and X ２１ It is the same as this.

[0154] In formula (2-1), R ２１ｔ and R ２２ｔ Each of these independently represents a hydrogen atom or a substituent. ２１ｔ and R ２２ｔ The definition and preferred embodiment of the substituent represented by the above formula (2) is Ar ２１ The substituents that may be present on the aromatic ring represented by R are the same. ２１ｔ and R ２２ｔThese atoms may be bonded to each other to form a ring which may have substituents. The ring may be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring, with an aromatic ring being preferred. The ring may be monocyclic or polycyclic, with a monocyclic ring being preferred. The number of ring member atoms of the ring is preferably 5 to 14, more preferably 6 to 10, and even more preferably 6. The ring may have heteroatoms. Examples of heteroatoms include nitrogen, sulfur, oxygen, selenium, tellurium, phosphorus, silicon, and boron, with sulfur, nitrogen, or oxygen being preferred. Examples of substituents that the ring may have and preferred embodiments are shown in the above formula (2) Ar ２１ These are the same substituents that the aromatic ring represented by may have.

[0155] Specific examples of compounds represented by formula (2) include the following compounds.

[0156]

[0157] In the above compound, A represents any of the groups exemplified as A in the first compound described above.

[0158] [Compound represented by formula (3)] Next, we will describe in detail the compound represented by formula (3).

[0159]

[0160] In formula (3), R ３１ and R ３２ Each of these independently represents a hydrogen atom or a substituent. ３１ and D ３２ Each of these independently represents a group that can be expressed in one of the formulas (D-11) to (D-13). ３１ and L ３２ Each of these independently represents a base represented by any of the above formulas (D-1) to (D-3). n31 and n32 each independently represent an integer from 0 to 2. A ３１represents a base represented by formula (A-3) or formula (A-4). In formula (D-11), k represents an integer from 0 to 4. A represents a ring represented by formula (d1) or formula (d2). B independently represents a ring represented by any of the formulas (d3) to (d7). D represents a ring represented by any of the formulas (d8) to (d10). In formulas (d8) to (d10), Z １ｂ Each of these is independently -CR Ａ = or represents a nitrogen atom. R Ａ X represents a hydrogen atom or substituent. １ｂ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents R Ａ１ ~R Ａ５ Each of these independently represents a hydrogen atom or a substituent. Ａ If there are two or more, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. * indicates a bond position. The rings represented by formulas (d8) to (d10) are fused at the two fused ring positions represented by *4. In formula (D-12), Z １１ｂ ~Z １６ｂ One of them represents -C(*) =, and the five independently represent -CR Ａ = or represents a nitrogen atom. R Ａ R represents a hydrogen atom or substituent. Ａ If there are two or more, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. * indicates a bond position. In formula (D-13), X １１ｂ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４２ -, or -C (=CR) Ａ５ ２ ) represents R Ａ１ ~R Ａ５ Each of these independently represents a hydrogen atom or a substituent. ２１ｂ ~Z ２４ｂ One of them represents -C(*) =, and the three independently represent -CR Ａ = or represents a nitrogen atom. R Ａ R represents a hydrogen atom or substituent. Ａ If there are two or more, R Ａ They may be bonded to each other to form a non-aromatic ring which may have substituents. * indicates a bond position. In formula (A-3), R ３３ ~R ３６ Each independently represents a hydrogen atom or a substituent. m3 and m4 independently represent 0 or 1. Ar ３１ V represents an aromatic ring which may have substituents. ３１ and V ３２ One of them is -C (=Y Ｘ ) represents -, and the other represents a sulfur atom, an oxygen atom, -NR Ｘ１ -, -CR Ｘ２ ２ -, or -C (=Y Ｘ ) represents V ３３ and V ３４ One of them is -C (=Y Ｘ ) represents -, and the other represents a sulfur atom, an oxygen atom, -NR Ｘ１ -, -CR Ｘ２ ２ -, or -C (=Y Ｘ ) represents Y Ｘ This consists of a sulfur atom, an oxygen atom, and =NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents R Ｙ１ R represents a hydrogen atom or substituent. Ｙ２ and R Ｙ３ These are, independently, a cyano group and -SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents R Ｙ４ ~R Ｙ６Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. Ｘ１ and R Ｘ２ Each of these independently represents a hydrogen atom or a substituent. * represents a bond position. In formula (A-4), R ３７ ~R ４０ Each independently represents a hydrogen atom or a substituent. m5 and m6 independently represent 0 or 1. Y ３１ ~Y ３４ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents R Ｙ１ R represents a hydrogen atom or substituent. Ｙ２ and R Ｙ３ These are, independently, a cyano group and -SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents R Ｙ４ ~R Ｙ６ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. * indicates the bond position.

[0161] In formula (3), R ３１ and R ３２ Each of these independently represents a hydrogen atom or a substituent, with hydrogen atoms being preferred. ３１ and R ３２ Examples of substituents represented by the above-mentioned substituent W include the substituents exemplified by D. ３１ and D ３２ Each of these independently represents a group represented by any of formulas (D-11) to (D-13), and in terms of superior effects of the present invention, a group represented by any of formulas (D-11) to (D-13) is preferred, and a group represented by either formula (D-11) or formula (D-13) is more preferred. ３１ and L ３２Each of these independently represents a base represented by one of the formulas (D-1) to (D-3). The details of formulas (D-1) to (D-3) are as described above. Each of n31 and n32 independently represents an integer from 0 to 2, preferably 0 or 1, and more preferably 0. In particular, it is preferable that both n31 and n32 are 0. A ３１ This represents a group represented by formula (A-3) or a group represented by formula (A-4).

[0162] The groups represented by formulas (D-11) to (D-13), formula (A-3), and formula (A-4) will be described in detail below. In formula (D-11), the definitions and preferred embodiments of k, A, and B are the same as those of k, A, and B in formula (D-1), respectively. The bond positions represented by * in formulas (d1) to (d7) correspond to the bond positions represented by * in formula (D-11). D represents a ring represented by any of formulas (d8) to (d10). In formula (D-11), adjacent rings represented by A, B, and D are fused at the fused ring positions indicated by *1 to *4 in formulas (d1) to (d10). That is, the group represented by formula (D-11) is a monovalent fused ring group consisting of rings represented by A, k B, and D. For example, when k=0, A and D are fused; when k=1, A and B, and B and D are fused; and when k=2, A and B, two adjacent Bs, and B and D are fused.

[0163] In formulas (d8) to (d10), Z １ｂ Each of these is independently -CR Ａ = or represents a nitrogen atom. X １ｂ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents an oxygen atom, sulfur atom, selenium atom, or -NR Ａ１ - is preferred, and is an oxygen atom, a sulfur atom, or -NR Ａ１ - is preferable. R Ａ and RＡ１ ~R Ａ５ This is as described above in equation (D-1).

[0164] R Ａ If there are two or more (in other words, Z １ｂ Two or more of these are -CR Ａ If =, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. In this case, two adjacent Z elements １ｂ ga-CR Ａ = and adjacent R Ａ It is preferable that they bond with each other. The non-aromatic ring may be either an aliphatic hydrocarbon ring or an aliphatic heterocycle, with an aliphatic hydrocarbon ring being preferred. The non-aromatic ring may be either a monocyclic or polycyclic ring, with a monocyclic ring being preferred. The number of member atoms of the non-aromatic ring is preferably 3 to 20, more preferably 5 to 12, and even more preferably 5 to 10. Examples of substituents that the non-aromatic ring may have include the substituent W mentioned above, and halogen atoms, alkyl groups which may have substituents, or silyl groups are preferred.

[0165] The rings represented by formulas (d8) to (d10) above are fused at two fused ring positions represented by *4. For example, if A is a group represented by formula (d1), k is 1, B is a group represented by formula (d3), and D is a group represented by formula (d8), then A and B are fused at the fused ring position represented by *1 in formula (d1) and the fused ring position represented by *2 in formula (d3), and B and D are fused at the fused ring position represented by *3 in formula (d3) and the fused ring position represented by *4 in formula (d8), or A and B are fused at the fused ring position represented by *1 in formula (d1) and the fused ring position represented by *3 in formula (d3), and B and D are fused at the fused ring position represented by *2 in formula (d3) and the fused ring position represented by *4 in formula (d8).

[0166] In formula (D-12), Z １１ｂ ~Z １６ｂ One of them represents -C(*) =, and the five independently represent -CR Ａ = or represents a nitrogen atom. R Ａ This is as described above in equation (D-1). RＡ If there are two or more (in other words, Z １１ｂ ~Z １６ｂ Two or more of these are -CR Ａ If =, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. In this case, Z １１ｂ ~Z １６ｂ Two of the adjacent ones are -CR Ａ = and adjacent R Ａ It is preferable that they bond with each other. The definition and preferred embodiment of the non-aromatic ring which may have the above substituents are given by formulas (d8) to (d10) R Ａ It is the same as a non-aromatic ring which may have substituents that can be formed by bonding with each other.

[0167] In formula (D-13), X １１ｂ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents an oxygen atom, a sulfur atom, or -NR Ａ１ - is preferred, and an oxygen atom or a sulfur atom is more preferred. ２１ｂ ~Z ２４ｂ One of them represents -C(*) =, and the three independently represent -CR Ａ = or represents a nitrogen atom. R Ａ１ ~R Ａ５ and R Ａ This is as described above in equation (D-1). R Ａ If there are two or more (in other words, Z ２１ｂ ~Z ２４ｂ Two or more of these are -CR Ａ If =, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. In this case, Z ２１ｂ ~Z ２４ｂ Two of the adjacent ones are -CR Ａ = and adjacent R ＡIt is preferable that they bond with each other. The definition and preferred embodiment of the non-aromatic ring which may have the above substituents are given by formulas (d8) to (d10) R Ａ It is the same as a non-aromatic ring which may have substituents that can be formed by bonding with each other.

[0168] The group represented by formula (D-11) is preferably a group represented by any of formulas (D1) to (D7), and more preferably a group represented by any of formulas (D1) to (D3). The group represented by formula (D-12) is preferably a group represented by formula (C1). The group represented by formula (D-13) is preferably a group represented by formula (C2) or formula (C3), and more preferably a group represented by formula (C3).

[0169]

[0170]

[0171] In the above formulas (C1) to (C3) and (D1) to (D7), Z, X and X Ｉ These are Z, X, and X in equations (A1) to (A4) and equations (B1) to (B17), respectively. Ｉ This is the same as above. One side of Y represents X, and the other side represents Z. Ar independently represents a ring represented by equations (d8) to (d10) and a contracted ring consisting of one to three equations (d3) to (d7), or a ring represented by equations (d8) to (d10).

[0172] In formula (A-3), R ３３ ~R ３６ Each of these independently represents a hydrogen atom or a substituent, with hydrogen atoms being preferred. ３３ ~R ３６ Examples of substituents represented by the above-mentioned substituent W include the substituents exemplified by substituent W.

[0173] In formula (A-3), m3 and m4 each independently represent 0 or 1, and 0 is preferred in that the effects of the present invention are superior.

[0174] In equation (A-3), Ar ３１Ar represents an aromatic ring which may have substituents. The aromatic ring may be monocyclic or polycyclic. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, with an aromatic hydrocarbon ring being preferred. Among the aromatic rings, a benzene ring or a naphthalene ring is preferred. ３１ The substituents that the aromatic ring represented by the above-mentioned substituent W may have include the substituents exemplified by the above-mentioned substituent W, and the preferred embodiment is the above-mentioned R Ａ This is the same as the substituent represented by .

[0175] In formula (A-3), V ３１ and V ３２ One of them is -C (=Y Ｘ ) represents -, and the other represents a sulfur atom, an oxygen atom, -NR Ｘ１ -, -CR Ｘ２ ２ -, or -C (=Y Ｘ ) represents V ３３ and V ３４ One of them is -C (=Y Ｘ ) represents -, and the other represents a sulfur atom, an oxygen atom, -NR Ｘ１ -, -CR Ｘ２ ２ -, or -C (=Y Ｘ ) represents V ３１ and V ３２ Both of them are -C (=Y Ｘ It is preferable to represent ) and also V ３３ and V ３４ Both of them are -C (=Y Ｘ ) - is preferable, V ３１ ~V ３４ Both are -C (=Y Ｘ It is preferable to represent it as ).

[0176] Y Ｘ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents an oxygen atom or =CR Ｙ２ R Ｙ３ This is preferable. Ｙ１ R represents a hydrogen atom or substituent. Ｙ１Examples of substituents represented by include those exemplified by substituent W described above, and alkyl groups or aryl groups are preferred. Ｙ２ and R Ｙ３ These are, independently, a cyano group and -SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents a cyano group or -COR Ｙ６ This is preferred, and a cyano group is more preferred. Among them, R Ｙ２ and R Ｙ３ It is preferable that all of them are cyano groups. Ｙ４ ~R Ｙ６ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. The definition of an aliphatic hydrocarbon group is as described above, with a preference for aliphatic hydrocarbon groups having 1 to 3 carbon atoms. The definition of an aromatic ring group is as described above, with a preference for aromatic hydrocarbon groups, and a preference for phenyl groups. The definition of an aliphatic heterocyclic group is as described above, with a preference for oxygen atoms, sulfur atoms, or nitrogen atoms as heteroatoms of the aliphatic heterocyclic group. Ｙ４ ~R Ｙ６ Examples of substituents that each represented group may have include the substituents exemplified by substituent W above.

[0177] R Ｘ１ and R Ｘ２ Each of these independently represents a hydrogen atom or a substituent. Ｘ１ and R Ｘ２ Examples of substituents represented by include the group exemplified by substituent W, and alkyl groups or aryl groups are preferred, with alkyl groups being more preferred. The alkyl group may be linear, branched, or cyclic, with linear being preferred. The number of carbon atoms in the alkyl group is preferably 1 to 20, 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 phenyl groups being preferred. The aryl group may have further substituents, and examples of substituents include the group exemplified by substituent W.

[0178] In formula (A-4), R ３７ ~R ４０ Each of these independently represents a hydrogen atom or a substituent, with hydrogen atoms being preferred. ３７ ~R ４０ Examples of substituents represented by the above-mentioned substituent W include the substituents exemplified by substituent W.

[0179] In formula (A-4), m5 and m6 each independently represent 0 or 1, and 0 is preferred in that the effects of the present invention are superior.

[0180] In formula (A-4), Y ３１ ~Y ３４ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents an oxygen atom or =CR Ｙ２ R Ｙ３ This is preferable. Ｙ１ ~R Ｙ３ This is as described above in equation (A-3).

[0181] Specific examples of compounds represented by formula (3) include the following compounds.

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] In the above compound, A exhibits one of the following structures.

[0190]

[0191]

[0192]

[0193] Compounds represented by any of formulas (1) to (3) (hereinafter also simply referred to as "specific compounds") may be purified as necessary. Examples of methods for purifying specific compounds include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, slurry washing, reprecipitation purification, and purification and recrystallization using adsorbents such as activated carbon.

[0194] The content of the specific compound in the photoelectric conversion film (= film thickness of the specific compound on a single-layer basis / film thickness of the photoelectric conversion film × 100) is not particularly limited, but is preferably 15 to 75 volume%, more preferably 20 to 60 volume%, and even more preferably 20 to 50 volume%. As described above, only one specific compound may be used, or two or more may be used. When two or more are used, it is preferable that their total amount be within the above range.

[0195] <n-type organic semiconductor> In terms of superior effects of the present invention, it is preferable that the photoelectric conversion film contains an n-type organic semiconductor other than compound N-1 described above. The n-type organic semiconductor is a compound different from the specific compound described above. There are no particular limitations on the n-type organic semiconductor other than compound N-1, but among them, fullerenes selected from the group consisting of fullerenes and their derivatives are preferred. Examples of fullerenes include fullerene C60, fullerene C70, fullerene C76, fullerene C78, ​​fullerene C80, fullerene C82, fullerene C84, fullerene C90, fullerene C96, fullerene C240, fullerene C540, and mixed fullerenes. Examples of fullerene derivatives include compounds in which substituents are added to the above fullerenes. The substituents are preferably alkyl groups, aryl groups, or heterocyclic groups. As fullerene derivatives, the compounds described in Japanese Patent Application Publication No. 2007-123707 are preferred.

[0196] The molecular weight of the n-type organic semiconductor other than compound N-1 is preferably 200 to 1,200, and more preferably 200 to 900.

[0197] The maximum absorption wavelength of n-type organic semiconductors other than compound N-1 is preferably in the range of 400 nm or less, or 500 to 600 nm.

[0198] The difference in electron affinity between the specific compound and the n-type organic semiconductor other than compound N-1 is preferably 0.1 eV or greater.

[0199] Other n-type organic semiconductors besides compound N-1 may be used individually or in combination of two or more. When the photoelectric conversion film contains n-type organic semiconductors other than compound N-1, the content of n-type organic semiconductors in the photoelectric conversion film (film thickness of n-type organic semiconductors other than compound N-1 on a single-layer basis / film thickness of the photoelectric conversion film × 100) is preferably 5 to 75 volume%, more preferably 10 to 50 volume%, and even more preferably 15 to 45 volume%.

[0200] <p-type organic semiconductor> The photoelectric conversion film preferably further contains a p-type organic semiconductor. The p-type organic semiconductor is a compound different from the specified compound mentioned above. A p-type organic semiconductor is a donor organic semiconductor material (compound), which is an organic compound that readily donates electrons. In other words, a p-type organic semiconductor is the organic compound with the smaller ionization potential when two organic compounds are brought into contact. The p-type organic semiconductor may be used alone or in combination of two or more types.

[0201] Examples of p-type organic semiconductors include triarylamine compounds (for example, 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 Japanese Patent Application Publication No. 2011-228614, compounds described in paragraphs

[0052] to

[0063] of Japanese Patent Application Publication No. 2011-176259, and compounds described in paragraphs

[0119] to

[0158] of Japanese Patent Application Publication No. 2011-225544) Compounds, compounds described in paragraphs

[0044] to

[0051] of Japanese Patent Publication No. 2015-153910 and compounds described in paragraphs

[0086] to

[0090] of Japanese Patent Publication 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]be Nzothiophene (TBBT) derivatives, compounds described in paragraphs

[0031] to

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

[0043] to

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

[0025] to

[0037] and

[0099] to

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

[0029] to

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

[0015] to

[0025] of WO 2018 / 207722, and compounds described in paragraph

[004] of JP 2019-054228. Compounds described in paragraphs [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 JP 2019-080052, 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 JP 2019-050398,The compounds described in paragraphs

[0033] to

[0036] of Japanese Patent Publication No. 2018-206878, the compounds described in paragraph

[0038] of Japanese Patent Publication No. 2018-190755, the compounds described in paragraphs

[0019] to

[0021] of Japanese Patent Publication No. 2018-026559, the compounds described in paragraphs

[0031] to

[0056] of Japanese Patent Publication No. 2018-170487, the compounds described in paragraphs

[0036] to

[0041] of Japanese Patent Publication No. 2018-078270, and Japanese Patent Publication No. 2018-16620 The compounds described in paragraphs

[0055] to

[0082] of Patent Publication No. 0, the compounds described in paragraphs

[0041] to

[0050] of Japanese Patent Application Publication No. 2018-113425, the compounds described in paragraphs

[0044] to

[0048] of Japanese Patent Application Publication No. 2018-085430, the compounds described in paragraphs

[0041] to

[0045] of Japanese Patent Application Publication No. 2018-056546, the compounds described in paragraphs

[0042] to

[0049] of Japanese Patent Application Publication No. 2018-046267, paragraphs

[0042] to

[0049] of Japanese Patent Application Publication No. 2018-014474 Examples include compounds described in paragraphs

[0031] to

[0036] , compounds described in paragraphs

[0036] to

[0046] of WO2018 / 016465, compounds described in paragraphs

[0045] to

[0048] of Japanese Patent Application Publication No. 2020-010024, etc.), cyanine compounds, oxonol compounds, polyamine compounds, indole compounds, pyrrole compounds, pyrazole compounds, polyarylene compounds, condensed aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives and fluorantene derivatives, etc.), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyarylalkane compounds, pyrazolone compounds, aminosubstituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having nitrogen-containing heterocyclic compounds as ligands. Examples of p-type organic semiconductors include compounds with a lower ionization potential than n-type organic semiconductors. 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 semiconductors are given below.

[0202]

[0203]

[0204]

[0205]

[0206] The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or greater.

[0207] The p-type semiconductor material may be used alone or in combination of two or more types. When the photoelectric conversion film contains a p-type organic semiconductor, the content of the p-type organic semiconductor in the photoelectric conversion film (film thickness of the p-type organic semiconductor on a single-layer basis / film thickness of the photoelectric conversion film × 100) is preferably 15 to 75 volume%, more preferably 20 to 60 volume%, and even more preferably 25 to 50 volume%. It is preferable that the photoelectric conversion film is substantially composed of compound N-1, a specific compound, fullerenes selected from the group consisting of fullerenes and their derivatives, and a p-type organic semiconductor included as desired. Substantially, the total content of compound N-1, the specific compound, the above fullerenes, and the p-type organic semiconductor relative to the total mass of the photoelectric conversion film is 90 to 100 volume%, preferably 95 to 100 volume%, and more preferably 99 to 100 volume%.

[0208] Photoelectric conversion films containing specific compounds are non-luminescent films and have characteristics different from organic light-emitting diodes (OLEDs). A non-luminescent film is defined as a film with a luminescence quantum efficiency of 1% or less, preferably 0.5% or less, and more preferably 0.1% or less. The lower limit is often 0% or more.

[0209] <Dye> The photoelectric conversion film may contain a dye in addition to the specified compound mentioned above. The dye is a compound different from the specified compound mentioned above. Organic dyes are preferred as the dye. Examples of organic pigments include cyanine pigments, styryl pigments, hemicyanine pigments, merocyanine pigments (including zeromethine merocyanine (simple merocyanine)), rhodacyanine pigments, allopolar pigments, oxonol pigments, hemioxonol pigments, squarylium pigments, croconium pigments, azametine pigments, coumarin pigments, allylidene pigments, anthraquinone pigments, triphenylmethane pigments, azo pigments, azomethine pigments, metallocene pigments, fluorenone pigments, fulgide pigments, perylene pigments, phenazine pigments, phenothiazine pigments, quinone pigments, diphenylmethane pigments, polyene pigments, acridine pigments, acridinone pigments, diphenylamine pigments, quinophthalone pigments, phenoxazine pigments, phthaloperylene pigments, dioxane pigments, porphyrin pigments, chlorophyll pigments, phthalocyanine pigments, subphthalocyanine pigments, and metal complex pigments.

[0210] The maximum absorption wavelength of the dye is preferably in the visible light region, more preferably 400 to 650 nm, and even more preferably 450 to 650 nm.

[0211] The dye may be used alone or in combination of two or more types. 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 on a single-layer basis / (film thickness of the specific compound on a single-layer basis + film thickness of the dye on a single-layer basis) × 100)) is preferably 15 to 75 volume%, more preferably 20 to 60 volume%, and even more preferably 20 to 50 volume%.

[0212] <Method of Film Formation> As a method for forming the above-mentioned photoelectric conversion film, for example, a dry film formation method can be used. Examples of dry film formation methods include physical vapor deposition methods such as evaporation (especially vacuum evaporation), sputtering, ion plating, and MBE (Molecular Beam Epitaxy), as well as CVD (Chemical Vapor Deposition) methods such as plasma polymerization, with vacuum evaporation being preferred. When forming a photoelectric conversion film by vacuum evaporation, manufacturing conditions such as the degree of vacuum and evaporation temperature can be set according to conventional methods.

[0213] The film thickness of the photoelectric conversion film is preferably 10 to 1000 nm, more preferably 50 to 800 nm, and even more preferably 50 to 500 nm.

[0214] [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 from 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 antimony tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); thin metal films of gold, silver, chromium, and nickel; mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, as well as nanocarbon materials such as carbon nanotubes and graphene. Conductive metal oxides are preferred in terms of high conductivity and transparency.

[0215] Typically, when a conductive film is made thinner than a certain range, its resistance often increases sharply. In the solid-state image sensor incorporating the photoelectric conversion element according to this embodiment, the sheet resistance may be 100 to 10000 Ω / □, and there is a great degree of freedom in the range of film thickness that can be thinned. Also, the thinner the upper electrode (transparent conductive film) 15, the less light it absorbs, and generally the light transmittance increases. An increase in light transmittance is desirable because it increases light absorption in the photoelectric conversion film and increases the photoelectric conversion ability. Considering the suppression of leakage current, the increase in the resistance of the thin film, and the increase in transmittance associated with thinning, the thickness of the upper electrode 15 is preferably 5 to 100 nm, and more preferably 5 to 20 nm.

[0216] The lower electrode 11 may be made transparent or opaque to reflect light, depending on the application. Examples of materials that make up the lower electrode 11 include conductive metal oxides such as tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide (IZO); metals such as gold, silver, 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 grampene.

[0217] The method for forming electrodes can be appropriately selected depending on the electrode material. Specifically, 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 (sol-gel method, etc.), and coating of indium tin oxide dispersions.

[0218] [Charge-blocking films: electron-blocking films, hole-blocking films] It is preferable that the photoelectric conversion element has one or more intermediate layers between the conductive film and the transparent conductive film, in addition to the photoelectric conversion film. An example of the above intermediate layer is a charge-blocking film. When the photoelectric conversion element has this film, the characteristics of the resulting photoelectric conversion element (quantum efficiency, response speed, etc.) are better. Examples of charge-blocking films include electron-blocking films and hole-blocking films.

[0219] [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 electron blocking films. Examples of polymer materials include polymers such as phenylenevinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, as well as their derivatives.

[0220] Furthermore, the electron blocking film may be composed of multiple films. The electron blocking film may also be composed of inorganic materials. Generally, inorganic materials have a higher dielectric constant than organic materials, so when inorganic materials are 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 as electron blocking films 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.

[0221] [Hole Blocking Film] The hole blocking film is an acceptor-type organic semiconductor material (compound), and the above-mentioned n-type organic semiconductor can be used. The hole blocking film may also be composed of multiple films.

[0222] Examples of methods for manufacturing charge-blocking films include dry deposition and wet deposition. Examples of dry deposition methods include vapor deposition and sputtering. Vapor deposition can be either physical vapor deposition (PVD) or chemical vapor deposition (CVD), with physical vapor deposition methods such as vacuum deposition being preferred. Examples of wet deposition methods include inkjet, spray, nozzle printing, spin coating, dip coating, casting, die coating, roll coating, bar coating, and gravure coating, with inkjet being preferred in terms of high-precision patterning.

[0223] The thickness of the charge blocking film (electron blocking film and hole blocking film) is preferably 3 to 200 nm, more preferably 5 to 100 nm, and even more preferably 5 to 30 nm, respectively.

[0224] [Substrate] The photoelectric conversion element may further have a substrate. Examples of substrates include semiconductor substrates, glass substrates, and plastic substrates. Typically, the substrates are layered on the substrate in the following order: conductive film, photoelectric conversion film, and transparent conductive film.

[0225] [Sealing Layer] The photoelectric conversion element may further have a sealing layer. Photoelectric conversion materials can be significantly degraded in performance due to the presence of degradation factors such as water molecules. Therefore, the entire photoelectric conversion film can be sealed by covering it with a sealing layer made of a dense metal oxide, metal nitride or metal nitride oxide ceramic, or diamond-like carbon (DLC), which does not allow water molecules to penetrate, thereby preventing the above-mentioned degradation. Examples of sealing layers include those described in paragraphs

[0210] to

[0215] of Japanese Patent Application Publication No. 2011-082508, and these contents are incorporated herein by reference.

[0226] [Image Sensor] One example of an application of the photoelectric conversion element is an image sensor. An image sensor is an element that converts the optical information of an image into an electrical signal. Typically, multiple photoelectric conversion elements are arranged in a matrix on the same plane, and each photoelectric conversion element (pixel) converts the optical signal into an electrical signal, and these electrical signals can be output sequentially to the outside of the image sensor for each pixel. For this purpose, each pixel is composed of one or more photoelectric conversion elements and one or more transistors. As for the manufacturing method of the image sensor, one example is a method that includes a process for manufacturing the photoelectric conversion element of the present invention.

[0227] [Optical Sensor] Other applications of the photoelectric conversion element include, for example, photocells and optical sensors, 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 it may be used as a line sensor in which the photoelectric conversion elements are arranged in a straight line or as a two-dimensional sensor arranged on a plane.

[0228] [Compounds] This invention also includes the invention of compounds. The compounds of this invention are the specified compounds described above.

[0229] The present invention will be described in more detail below based on the following examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples.

[0230] [Compounds used in photoelectric conversion films] The following lists the materials used in the photoelectric conversion films.

[0231] [n-type organic semiconductor] ・C ６０ : Fullerene C ６０

[0232]

[0233] [A compound (pigment B) represented by any of the formulas (1) to (3)]

[0234]

[0235] [A compound (dye R) represented by any of the formulas (1) to (3)]

[0236]

[0237] [p-type organic semiconductor]

[0238]

[0239] [Compounds other than those listed above]

[0240] [Evaluation] Using the above materials, photoelectric conversion elements for each example and comparative example are fabricated according to the procedure shown below. Subsequently, the responsiveness (response rate reduction rate) of each photoelectric conversion element when receiving light of a wavelength of 450 nm (blue-green light) during repeated evaluations, and the quantum efficiency when receiving light of each wavelength are evaluated using the following method.

[0241] 〔test〕

[0242] <Fabrication of Photoelectric Conversion Element> A photoelectric conversion element in the form shown in Figure 2 is fabricated using the various components shown above. Here, the photoelectric conversion element consists of 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 is deposited on a glass substrate by sputtering to form the lower electrode 11 (thickness: 30 nm), and then a compound (EB-1) is deposited on the lower electrode 11 by vacuum heating deposition to form an electron blocking film 16A (thickness: 30 nm). Subsequently, with the temperature of the glass substrate controlled to 25°C, each compound is co-deposited on the electron blocking film 16A by vacuum deposition in the composition ratios shown in the table below. This forms a photoelectric conversion film 12 having a bulk heterostructure of 240 nm. At this time, the deposition rate of the photoelectric conversion film 12 is set to 1.0 Å / second. Furthermore, a compound (EB-2) is deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). Amorphous ITO is deposited on the hole blocking film 16B by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm). An SiO film is formed on the upper electrode 15 as a sealing layer by vacuum deposition, and then aluminum oxide (Al) is deposited thereon by ALCVD (Atomic Layer Chemical Vapor Deposition). ２ O ３ A layer is formed, and the resulting laminate is heated in a glove box at 150°C for 30 minutes to obtain a photoelectric conversion element.

[0243]

[0244] <Evaluation of Dark Current> The dark current of each obtained photoelectric conversion element is measured using the following method. 2.5 × 10⁻¹⁶ ５ A voltage is applied to achieve an electric field strength of V / cm, and the current value in the dark (dark current) is measured. As a result, the dark current for all photoelectric conversion elements was 50 nA / cm. ２ The following confirms that it exhibits a sufficiently low dark current.

[0245] <Responsiveness during repeated evaluation (response speed reduction rate)> For each photoelectric conversion element, the responsiveness (response speed reduction rate) during repeated evaluation when receiving blue-green light will be evaluated using the following method. 2.0 × 10⁻¹⁶ ５ A voltage is applied to achieve an intensity of V / cm. Then, an LED (light emitting diode) is set to 1 Hz, with a duty cycle of 50% and an illumination intensity of 50 μW / cm². ２ The device is turned on, and light is shone from the upper electrode (transparent conductive film) side. The photocurrent at a wavelength of 450 nm is measured with an oscilloscope, and the rise time from 0% signal intensity (when no light is shone) to 97% signal intensity is measured every 30 minutes. The above evaluation is repeated 10 times, and the response speed reduction rate is calculated from the rise time of the 1st time and the rise time of the 10th time based on the following formula, and evaluated according to the following classification. A response speed reduction rate of B or higher is preferable, and A is most preferable. ・Response speed reduction rate (%) = [(Rise time of the 10th time - Rise time of the 1st time) / Rise time of the 1st time] × 100

[0246] A: Less than 1% B: 1% or more but less than 2% C: 2% or more

[0247] <Photoelectric Conversion Efficiency (External Quantum Efficiency)> For each photoelectric conversion element, the photoelectric conversion efficiency when receiving light of each wavelength is evaluated using the following method. 2.0 × 10⁻¹⁶ for each photoelectric conversion element. ５ After applying a voltage to achieve an electric field strength of V / cm, a light intensity of 50 μW / cm is applied from the upper electrode (transparent conductive film) side. ２ The photoelectric conversion efficiencies (external quantum efficiencies) are extracted at wavelengths of 450 nm, 530 nm, and 610 nm by irradiating with light and performing IPCE (Incident photon-to-current conversion efficiency) measurements using an Optel constant-energy quantum efficiency measuring device. Based on the photoelectric conversion efficiencies of each photoelectric conversion element when the photoelectric conversion efficiency of the photoelectric conversion element in Example 1-1 is normalized to 1, the following classifications are used for evaluation.

[0248] A: 0.9 or higher B: 0.8 or higher but less than 0.9 C: Less than 0.8

[0249] [Results] The evaluation results are shown in the table below. In the table, the ratios listed in the "Composition Ratio" column represent the volume ratio of n-type organic semiconductor, dye B, dye R, and p-type organic semiconductor (n-type organic semiconductor: dye B: dye R: p-type organic semiconductor).

[0250]

[0251] The results shown in the table demonstrate that the photoelectric conversion element of the present invention exhibits excellent responsiveness (response speed reduction rate) during repeated evaluations, and furthermore, excellent quantum efficiency. In addition, for Examples 1-1, 1-2, and 1-4 to 1-13, even when the measurement wavelength in the evaluation of the above-mentioned <response speed reduction rate during repeated evaluations> is changed from 450 nm to 530 nm or 610 nm, the same results as the response speed reduction rate shown in the table can be obtained. A comparison between Example 1-1 and Example 1-2 shows that when the photoelectric conversion film further contains fullerenes selected from the group consisting of fullerenes and their derivatives, the responsiveness during repeated evaluations is even better. A comparison between Example 1-1 and Example 1-3 shows that when the photoelectric conversion film contains two or more compounds represented by any of formulas (1) to (3), the responsiveness during repeated evaluations is even better. A comparison between Example 1-1 and Example 1-4 shows that when the photoelectric conversion film further contains a p-type organic semiconductor, at least one of the effects of quantum efficiency and responsiveness during repeated evaluation is superior. A comparison between Example 1-1 and Examples 1-5 to 1-8 and Example 1-9 shows that when the photoelectric conversion film contains two or more compounds represented by any of formulas (1) to (3), and at least one of them is one of the aforementioned compound 1A, compound 1B, and compound represented by formula (2-1), the responsiveness during repeated evaluation is superior.

[0252] 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 (N-1) and at least one selected from the group consisting of compounds represented by any one of formula (1) to formula (3). In formula (N-1), Ar Ｎ１ represents a fused polycyclic aromatic ring which may have a substituent. C １ contains X Ｎ１ and represents a ring that is fused with the fused polycyclic aromatic ring. X Ｎ１ represents an oxygen atom, -NR-, -C(R) ２ -, or a sulfur atom. R represents a hydrogen atom or a substituent. Y Ｎ１ and Y Ｎ２ each independently represent an oxygen atom, a sulfur atom, =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ . R Ｗ１ represents a hydrogen atom or a substituent. R Ｗ２ and R Ｗ３ each independently represent a cyano group, -COOR Ｗ４ , -COR Ｗ５ , or -SO ２ R Ｗ６ . R Ｗ４ to R Ｗ６ 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. When X Ｎ１ is -NR- and at least one of Y Ｎ１ and Y Ｎ２ is =NR Ｗ１ , R and R Ｗ１ may be bonded to each other to form a ring. n represents an integer of 1 or more. In formula (1), D １１ each independently represent a group represented by any one of formula (D-1) to formula (D-3). L １１ each independently represent a single bond, -CR Ｂ =CR Ｂ -, or -C≡C-. R Ｂ each independently represent a hydrogen atom or a substituent. A １１ A represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, an optionally substituted aromatic ring group, a group represented by formula (A-1), or a group represented by formula (A-2). １２ represents the base represented by formula (A-1) or the base represented by formula (A-2). n11 represents an integer from 0 to 2. In formula (D-1), k represents an integer from 0 to 4. A and C each independently represent a ring represented by formula (d1) or formula (d2). B each independently represents a ring represented by any of formulas (d3) to (d7). In formulas (d1) to (d7), Z １ａ Each of these is independently -CR Ａ = or represents a nitrogen atom. R Ａ X represents a hydrogen atom or substituent. １ａ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents X ２ａ is an oxygen atom, a sulfur atom, or -NR Ａ１ Represents -. R Ａ１ ~R Ａ６ Each of these independently represents a hydrogen atom or a substituent. Ａ２ Allies, R Ａ３ Allies, R Ａ４ Allies, R Ａ５ Allies, and R Ａ６ Each of them may be bonded to each other to form a ring which may have substituents. ３ａ represents an oxygen atom or a sulfur atom. * represents a bonding position. The rings represented by formulas (d1) and (d2) are fused at the two fused ring positions represented by *1. The rings represented by formulas (d3) to (d7) are fused with one adjacent ring at the two fused ring positions represented by *2, and with the other adjacent ring at the two fused ring positions represented by *3. In formula (D-2), Z １１ａ ~Z １６ａ two of which represent -C(*)=, and four of which each independently represent -CR Ａ = or a nitrogen atom. R Ａ represents a hydrogen atom or a substituent. * represents a bonding position. In formula (D-3), X １１ａ represents 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 )-. R Ａ１ to R Ａ５ each independently represent a hydrogen atom or a substituent. Z ２１ａ to Z ２４ａ two of which represent -C(*)=, and two of which each independently represent -CR Ａ = or a nitrogen atom. R Ａ represents a hydrogen atom or a substituent. * represents a bonding position. In formula (A-1), R １１ to R １３ each independently represent a hydrogen atom or a substituent. m1 represents 0 or 1. C １１ represents a ring containing two or more carbon atoms and optionally having a substituent. W １ represents an oxygen atom, a sulfur atom, =NR Ｗ１ , or =CR Ｗ２ R Ｗ３ . R Ｗ１ represents a hydrogen atom or a substituent. R Ｗ２ and R Ｗ３ each independently represent a cyano group, -COOR Ｗ４ , -COR Ｗ５ , or -SO ２ R Ｗ６ . R Ｗ４ to R Ｗ６ each independently represent an aliphatic hydrocarbon group optionally having a substituent, an aromatic ring group optionally having a substituent, or an aliphatic heterocyclic group optionally having a substituent. * represents a bonding position. In formula (A-2), R １４ to R １６ each independently represent a hydrogen atom or a substituent. m2 represents 0 or 1. W ２ and W ３ each independently represent a cyano group, -COOR Ｗ１１ , -COR Ｗ１２ , -SOR Ｗ１３ , or -SO ２ R Ｗ１４ . R Ｗ１１ to R Ｗ１４ 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. * represents a bonding position. In formula (2), R ２１ represents a hydrogen atom or a substituent. A ２１ represents a group represented by the aforementioned formula (A-1) or a group represented by the aforementioned formula (A-2). Ar ２１ represents an aromatic ring which may have a substituent. R ２２ represents an aryl group which may have a substituent, -C(R Ｌ１ )(R Ｌ２ )(R Ｌ３ ), or a heteroaryl group which may have a substituent. R Ｌ１ to R Ｌ３ each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or a hydrogen atom, and among R Ｌ１ to R Ｌ３ , at least two each independently represent the alkyl group which may have a substituent, the aryl group which may have a substituent, or the heteroaryl group which may have a substituent. The alkyl group which may have a substituent, the aryl group which may have a substituent, and the heteroaryl group which may have a substituent, which are represented by R Ｌ１ to R Ｌ３ , may be bonded to each other via a single bond or a divalent linking group to form a ring which may have a substituent. X ２１ represents -NR １ｓ -, -CR ２ｓ ２ -, a sulfur atom, an oxygen atom, or a selenium atom. R １ｓ and R ２ｓ Each of these independently represents a hydrogen atom or a substituent. ２ｓ They may be bonded to each other to form a ring which may have substituents. In formula (3), R ３１ and R ３２ Each of these independently represents a hydrogen atom or a substituent. ３１ and D ３２ Each of these independently represents a group that can be expressed in one of the formulas (D-11) to (D-13). ３１ and L ３２ Each of these independently represents a base represented by any of the above formulas (D-1) to (D-3). n31 and n32 each independently represent an integer from 0 to 2. A ３１ represents a base represented by formula (A-3) or formula (A-4). In formula (D-11), k represents an integer from 0 to 4. A represents a ring represented by formula (d1) or formula (d2). B independently represents a ring represented by any of formulas (d3) to (d7). D represents a ring represented by any of formulas (d8) to (d10). In formulas (d8) to (d10), Z １ｂ Each of these is independently -CR Ａ = or represents a nitrogen atom. R Ａ X represents a hydrogen atom or substituent. １ｂ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents R Ａ１ ~R Ａ５ Each of these independently represents a hydrogen atom or a substituent. Ａ If there are two or more, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. * indicates a bonding position. The rings represented by formulas (d8) to (d10) are fused at the two fused ring positions represented by *4. In formula (D-12), Z １１ｂ ~Z １６ｂ One of them represents -C(*) =, and the five independently represent -CR Ａ = or represents a nitrogen atom. R Ａ R represents a hydrogen atom or substituent. Ａ If there are two or more, R Ａ These elements may be bonded to each other to form a non-aromatic ring which may have substituents. * indicates a bond position. In formula (D-13), X １１ｂ It consists of an oxygen atom, a sulfur atom, a selenium atom, and -NR Ａ１ -, -SiR Ａ２ ２ -, -GeR Ａ３ ２ -, -CR Ａ４ ２ -, or -C (=CR) Ａ５ ２ ) represents R Ａ１ ~R Ａ５ Each of these independently represents a hydrogen atom or a substituent. ２１ｂ ~Z ２４ｂ One of them represents -C(*) =, and the three independently represent -CR Ａ = or represents a nitrogen atom. R Ａ R represents a hydrogen atom or substituent. Ａ If there are two or more, R Ａ They may be bonded to each other to form a non-aromatic ring which may have substituents. * indicates a bond position. In formula (A-3), R ３３ ~R ３６ Each independently represents a hydrogen atom or a substituent. m3 and m4 independently represent 0 or 1. Ar ３１ V represents an aromatic ring which may have substituents. ３１ and V ３２ One of them is -C (=Y Ｘ ) represents -, and the other represents a sulfur atom, an oxygen atom, -NR Ｘ１ -, -CR Ｘ２ ２ -, or -C (=Y Ｘ ) represents V ３３ and V ３４ One of them is -C (=Y Ｘ ) represents -, and the other represents a sulfur atom, an oxygen atom, -NR Ｘ１ -, -CR Ｘ２ ２ -, or -C (=Y Ｘ ) represents Y Ｘ This consists of a sulfur atom, an oxygen atom, and =NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents R Ｙ１ R represents a hydrogen atom or substituent. Ｙ２ and R Ｙ３ These are, independently, a cyano group and -SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents R Ｙ４ ~R Ｙ６ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. Ｘ１ and R Ｘ２ Each of these independently represents a hydrogen atom or a substituent. * represents a bond position. In formula (A-4), R ３７ ~R ４０ Each independently represents a hydrogen atom or a substituent. m5 and m6 independently represent 0 or 1. Y ３１ ~Y ３４ These are, independently, a sulfur atom, an oxygen atom, and =NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents R Ｙ１ R represents a hydrogen atom or substituent. Ｙ２ and R Ｙ３ These are, independently, a cyano group and -SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents R Ｙ４ ~R Ｙ６ Each of these independently represents an optionally substituted aliphatic hydrocarbon group, an optionally substituted aromatic ring group, or an optionally substituted aliphatic heterocyclic group. * indicates the bond position.

2. The photoelectric conversion element according to claim 1, wherein the photoelectric conversion film contains two or more compounds represented by any one of formulas (1) to (3).

3. The photoelectric conversion element according to claim 1, wherein the photoelectric conversion film contains at least one compound represented by formula (1).

4. X Ｎ１ The photoelectric conversion element according to claim 1, wherein the atom is an oxygen atom or -NR-.

5. Y Ｎ１ and Y Ｎ２ Both are oxygen atoms, or =NR Ｗ１ The photoelectric conversion element according to claim 1.

6. The photoelectric conversion element according to claim 1, wherein the compound represented by formula (N-1) is a compound represented by any of formulas (N-11) to (N-13). In formulas (N-11) to (N-13), X Ｎ２１ , X Ｎ２２ , X Ｎ３１ , X Ｎ３２ and X Ｎ４１ X in the above formula (N-1) Ｎ１ This is synonymous with Y. Ｎ２１ ~Y Ｎ２４ , Y Ｎ３１ ~Y Ｎ３４ , Y Ｎ４１ and Y Ｎ４２ This is Y in the above formula (N-1). Ｎ１ This is equivalent to: Z is independently =CR Ｚ - or represents a nitrogen atom. R Ｚ represents a hydrogen atom or substituent. Both Zs are R Ｚ is a substituent = CR Ｚ - If R Ｚ The substituents represented by may bond to each other to form a ring. m7 and m9 each independently represent an integer of 1 or more. m8 represents an integer of 0 or more. In the above formula (N-11), X Ｎ２１ is -NR- and Y Ｎ２１ and Y Ｎ２２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ They may be joined to each other to form a ring, X Ｎ２２ is -NR- and Y Ｎ２３ and Y Ｎ２４ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ They may combine with each other to form a ring. In formula (N-12), X Ｎ３１ is -NR- and Y Ｎ３１ and Y Ｎ３２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ They may be joined to each other to form a ring, X Ｎ３２ is -NR- and Y Ｎ３３ and Y Ｎ３４ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ They may be joined to each other to form a ring. In formula (N-13), X Ｎ４１ is -NR- and Y Ｎ４１ and Y Ｎ４２ At least one of them is = NR Ｗ１ If so, R and R Ｗ１ These two elements may join together to form a ring.

7. The photoelectric conversion element according to claim 1, wherein the compound represented by formula (N-1) is a compound represented by any of formulas (N-21) to (N-26). In equations (N-21) to (N-26), X is the same as X in equation (N-1). Ｎ１ This is equivalent to Y in the above formula (N-1). Ｎ１ This is equivalent to: Z is independently =CR Ｚ - or represents a nitrogen atom. R Ｚ represents a hydrogen atom or substituent. Both Zs are R Ｚ is a substituent = CR Ｚ - If R Ｚ The substituents represented by may bond to each other to form a ring. Also, if X is -NR- and at least one of the two Y adjacent to X is =NR Ｗ１ If so, R and R Ｗ１ These two elements may join together to form a ring.

8. The photoelectric conversion element according to claim 7, wherein in formulas (N-21) to (N-26), X is independently an oxygen atom or -NR-.

9. In formulas (N-21) to (N-26), Y is independently an oxygen atom or =NR Ｗ１ The photoelectric conversion element according to claim 7.

10. In the above formula (1), A １１ is a group represented by the above formula (A-1) or the above formula (A-2), n11 is 0, and D １１ The photoelectric conversion element according to claim 1, wherein the base is represented by the formula (D-1).

11. In formula (1) above, A １１ is a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, or an optionally substituted aromatic ring group, and n11 is 0 or 1, D １１ The photoelectric conversion element according to claim 1, wherein the base is represented by the formula (D-1).

12. In equation (2) above, X ２１ ga-NR １ｓ - or -CR ２ｓ ２ - The photoelectric conversion element according to claim 1.

13. The photoelectric conversion element according to claim 1, wherein the compound represented by formula (2) is the compound represented by formula (2-1). In formula (2-1), R ２１ , R ２２ A ２１ , and X ２１ These are, respectively, R in formula (2) above. ２１ , R ２２ A ２１ , and X ２１ It is the same as R ２１ｔ and R ２２ｔ Each of these independently represents a hydrogen atom or a substituent. ２１ｔ and R ２２ｔ These elements may be bonded to each other to form a ring which may have substituents.

14. The photoelectric conversion element according to any one of claims 1 to 13, wherein the photoelectric conversion film further comprises fullerenes selected from the group consisting of fullerenes and derivatives thereof.

15. The photoelectric conversion element according to any one of claims 1 to 13, wherein the photoelectric conversion film further comprises a p-type organic semiconductor.

16. A photoelectric conversion element according to any one of claims 1 to 13, wherein one or more intermediate layers are provided between the conductive film and the transparent conductive film, in addition to the photoelectric conversion film.

17. The photoelectric conversion element according to claim 16, wherein the intermediate layer is an electron blocking film or a hole blocking film.

18. An image sensor having a photoelectric conversion element according to any one of claims 1 to 13.

19. A light sensor having a photoelectric conversion element according to any one of claims 1 to 13.

20. A method for manufacturing an image sensor, comprising a step of manufacturing a photoelectric conversion element according to any one of claims 1 to 13.

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