Composition

Abstract

The present invention provides a composition that enables the achievement of a compound with which it is possible to produce a photoelectric conversion element that has small electric field intensity dependence of the response speed. A composition according to the present invention contains: a compound that is selected from the group consisting of a compound represented by formula (1) and a compound represented by formula (2); and an alcohol that has an acid dissociation constant pKa of 13.0 or less.

Description

composition

[0001] The present invention relates to a composition.

[0002] The compound is used in a wide range of fields, for example, in an element having a photoelectric conversion film as an organic electronics device. For example, Patent Document 1 discloses a photoelectric conversion element having a photoelectric conversion film containing a compound having a specific structure represented by formula (1).

[0003] International Publication No. 2023 / 042878

[0004] For example, with the demand for improved performance of image sensors, optical sensors, etc., there is a demand for photoelectric conversion elements that exhibit excellent characteristics. When manufacturing a photoelectric conversion element, a composition containing a compound is often used. When a composition containing the compound described in Patent Document 1 was studied, it was found that the electric field strength dependency of the response speed of the obtained photoelectric conversion element needed to be improved.

[0005] Therefore, an object of the present invention is to provide a composition from which a compound capable of producing a photoelectric conversion element having a response speed with little dependence on electric field strength can be obtained.

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

[0007] [1] A composition comprising a compound selected from the group consisting of a compound represented by formula (1) described later and a compound represented by formula (2) described later, and an alcohol having an acid dissociation constant pKa of 13.0 or less. [2] The composition according to [1], wherein the alcohol is an alcohol represented by formula (S1) described later. [3] The composition according to [1] or [2], wherein the alcohol has an acid dissociation constant pKa of 10.0 or less. [4] The composition according to any one of [1] to [3], wherein n1 represents 2 and n2 represents 1 or 2. [5] The composition according to any one of [1] to [4], wherein the compound represented by formula (1) is a compound represented by formula (1-1) described later, and the compound represented by formula (2) is a compound represented by formula (2-1) described later. [6] The monocycle having a conjugated structure is an aromatic 6-membered ring having an atom selected from the group consisting of carbon atoms and nitrogen atoms as ring member atoms, or an oxygen atom, a sulfur atom, a selenium atom, -NR Ｄ１ -, -SiR Ｄ２ ２ -, -GeR Ｄ３ ２ -, -CR Ｄ４ ２ - and >C=CR Ｄ５ ２ is a conjugated five-membered ring in which an atom or structure selected from the group consisting of Ｄ１ ~R Ｄ５ each independently represents a hydrogen atom or a substituent, or -Y Ｄ１ -Y Ｄ２ - is a non-aromatic conjugated six-membered ring constituting a ring, and Y Ｄ１ and Y Ｄ２ one of which is an oxygen atom, a sulfur atom, a selenium atom, or -NR Ｄ６ -, and the other is -CR ｃ２ ２ represents -, and R Ｄ６ represents a hydrogen atom or a substituent, R ｃ２ represents a hydrogen atom or a substituent, and the fused ring having a conjugated structure is formed by condensing a plurality of rings selected from the group consisting of the aromatic six-membered ring, the conjugated five-membered ring, and the non-aromatic conjugated six-membered ring. １ and A ２[8] The composition according to any one of [1] to [6], wherein each of A is independently a group represented by the above formula (A-1). １ and A ２ is a group represented by the formula (A-1) above, and the group represented by the formula (A-1) is a group represented by the formula (C-1) described later or a group represented by the formula (C-2) described later. [9] The composition according to any one of [1] to [8], comprising a compound represented by the formula (1) above and an alcohol represented by the formula (S1) described later.

[10] The composition according to any one of [1] to [9], further comprising an organic solvent other than the alcohol.

[11] The composition according to

[10] , wherein the organic solvent is composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, and halogen atoms.

[12] The composition according to

[10] or

[11] , wherein the content of the alcohol relative to the total content of the alcohol and the organic solvent is 10% by volume or more.

[13] The composition according to any one of [1] to

[12] , wherein the alcohol is an alcohol represented by the formula (S2) described later.

[14] The composition according to any one of [1] to

[13] , wherein the alcohol is an alcohol represented by formula (S3) described below.

[0008] According to the present invention, it is possible to provide a composition from which a compound that can be used to produce a photoelectric conversion element having a response speed that is less dependent on electric field strength can be obtained.

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

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

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

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

[0013] In this specification, with respect to a compound having an asymmetric atom, the general formula or structural formula representing the compound may be described without distinguishing between stereoisomers for convenience. Even in such a case, unless otherwise specified, the form of the compound is not limited to any one form, and may be any one form or a mixture. For example, unless otherwise specified, a compound having an asymmetric carbon atom may be either an S-form or an R-form, or a mixture thereof.

[0014] In this specification, unless otherwise specified, * in a formula represents a bonding position. The bonding direction of a divalent group (e.g., -CO-O-, etc.) in this specification is not limited unless otherwise specified. For example, when Y is -CO-O- in a compound represented by the formula "X-Y-Z", the compound may be either "X-O-CO-Z" or "X-CO-O-Z".

[0015] In this specification, when there are multiple substituents, linking groups, etc. (hereinafter also referred to as "substituents, etc.") represented by specific symbols, or when multiple substituents, etc. are specified at the same time, it means that the respective substituents, etc. may be the same or different from each other. This also applies to the specification of the number of substituents, etc. In this specification, unless otherwise specified, "substituents" include, for example, groups exemplified as the substituent W described below.

[0016] (Substituent W) The substituent W in this specification will be described. Examples of the substituent W include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, an aryl group, a heterocyclic group (a heteroaryl group or an aliphatic heterocyclic group), a cyano group, a nitro group, an alkoxy group, an aryloxy group, a silyl group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyl Examples of the substituent W include an oxy group, a primary, secondary, or tertiary amino group (including an anilino group), an alkylthio group, an arylthio group, a heterocyclic thio group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a phosphono group, a carboxy group, a phosphate group, a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, and a boronic acid group. Furthermore, each of the above groups may further have a substituent (e.g., one or more of the above groups, etc.), if possible. For example, an alkyl group which may have a substituent is also included as one form of the substituent W. Furthermore, when the substituent W has a carbon atom, the number of carbon atoms contained in the substituent W is, for example, 1 to 20. The number of atoms other than hydrogen atoms contained in the substituent W is, for example, 1 to 30. The compounds described below may have, as substituents, a carboxy group, a salt of a carboxy group, a salt of a phosphate group, a sulfonic acid group, a salt of a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, a boronic acid group (-B(OH) ２ ) and / or has no primary amino groups.

[0017] In this specification, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group. Furthermore, in this specification, unless otherwise specified, the number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6. The alkyl group may be linear, branched, or cyclic. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclopropyl group, and a cyclopentyl group. Furthermore, the alkyl group may be a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have these ring structures as partial structures. In the alkyl group that may have a substituent, examples of the substituent that the alkyl group may have include the groups exemplified for the substituent W. Of these, an aryl group (preferably having 6 to 18 carbon atoms, more preferably having 6 carbon atoms), a heteroaryl group (preferably having 3 to 18 carbon atoms, more preferably having 4 to 6 carbon atoms), or a halogen atom (preferably a fluorine atom or a chlorine atom) is preferred.

[0018] In this specification, unless otherwise specified, the alkyl group moiety in the alkoxy group is preferably the above-mentioned alkyl group. The alkyl group moiety in the alkylthio group is preferably the above-mentioned alkyl group. In the alkoxy group which may have a substituent, examples of the substituent that the alkoxy group may have include the same as the substituent in the alkyl group which may have a substituent. In the alkylthio group which may have a substituent, examples of the substituent that the alkylthio group may have include the same as the substituent in the alkyl group which may have a substituent.

[0019] In this specification, unless otherwise specified, the alkenyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkenyl group is preferably 2 to 20. In the alkenyl group which may have a substituent, examples of the substituent that the alkenyl group may have include the same as the substituents in the alkyl group which may have a substituent. In this specification, unless otherwise specified, the alkynyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkynyl group is preferably 2 to 20. In the alkynyl group which may have a substituent, examples of the substituent that the alkynyl group may have include the same as the substituents in the alkyl group which may have a substituent.

[0020] In this specification, unless otherwise specified, an aromatic ring or an aromatic ring constituting an aromatic ring group may be either a monocyclic ring or a polycyclic ring (e.g., 2 to 6 rings, etc.). A monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as a ring structure. A polycyclic (e.g., 2 to 6 rings, etc.) aromatic ring is an aromatic ring having a plurality of (e.g., 2 to 6, etc.) condensed aromatic ring structures as a ring structure. The number of ring members in the aromatic ring is preferably 5 to 15. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring. When the aromatic ring is an aromatic heterocyclic ring, the number of heteroatoms contained as ring member atoms is, for example, 1 to 10. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, and a fluorene ring.Examples of the aromatic heterocycle include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring (e.g., a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring), a tetrazine ring (e.g., a 1,2,4,5-tetrazine ring), a quinoxaline ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a naphthopyrrole ring, a naphthofuran ring, a naphthothiophene ring, a naphthoimidazole ring, a naphthoxazole ring, a pyrroloimidazole ring (e.g., a 5H-pyrrolo[1,2-a]imidazole ring), an imidazooxazole ring (e.g., an imidazo[2,1-b]oxazole ring), Thienothiazole rings (for example, thieno[2,3-d]thiazole rings, etc.), benzothiadiazole rings, benzodithiophene rings (for example, benzo[1,2-b:4,5-b']dithiophene rings, etc.), thienothiophene rings (for example, thieno[3,2-b]thiophene rings, etc.), thiazolothiazole rings (for example, thiazolo[5,4-d]thiazole rings, etc.), naphthodithiophene rings (for example, naphtho[2,3 [2,1-b:6,7-b']dithiophene ring, naphtho[2,1-b:6,5-b']dithiophene ring, naphtho[1,2-b:5,6-b']dithiophene ring, 1,8-dithiadicyclopenta[b,g]naphthalene ring, etc.), benzothienobenzothiophene ring, dithieno[3,2-b:2',3'-d]thiophene ring, and 3,4,7,8-tetrathiadicyclopenta[a,e]pentalene ring.

[0021] As used herein, the term "aromatic ring group" includes, for example, a group obtained by removing one or more hydrogen atoms (e.g., 1 to 5) from the above-mentioned aromatic ring. As used herein, the term "aryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic hydrocarbon ring among the above-mentioned aromatic rings. As used herein, the term "heteroaryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings. As used herein, the term "arylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above-mentioned aromatic rings. As used herein, the term "heteroarylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings. In the optionally substituted aromatic ring, optionally substituted aromatic ring group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted arylene group, and optionally substituted heteroarylene group, the types of substituents that these may have include, for example, the groups exemplified for the substituent W. When these groups which may have a substituent have a substituent, the number of the substituents may be one or more (for example, 1 to 4, etc.).

[0022] As used herein, the term "non-aromatic ring" refers to a ring structure that is not aromatic, and examples thereof include an aliphatic hydrocarbon ring and an aliphatic heterocycle. Examples of the aliphatic hydrocarbon ring include cycloalkane, cycloalkene, and cycloalkyne. As used herein, the term "aliphatic heterocyclic group" refers to, for example, a group obtained by removing one hydrogen atom from the aliphatic heterocycle. As used herein, the number of ring members in the aliphatic heterocyclic group is preferably 5 to 20, more preferably 5 to 12, and even more preferably 6 to 8. Examples of heteroatoms contained in the aliphatic heterocyclic group include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, with a sulfur atom, an oxygen atom, or a nitrogen atom being preferred. Examples of the aliphatic heterocycle constituting the aliphatic heterocyclic group include a pyrrolidine ring, an oxolane ring (tetrahydrofuran ring), a thiolane ring, a piperidine ring, a tetrahydropyran ring, a thiane ring (pentamethylene sulfide ring), a piperazine ring, a morpholine ring, a quinuclidine ring, an azetidine ring, an oxetane ring, an aziridine ring, a dioxane ring, and a γ-butyrolactone ring.

[0023] [Composition] The composition of the present invention comprises a compound selected from the group consisting of a compound represented by formula (1) and a compound represented by formula (2) (hereinafter also referred to as a "specific compound"), and an alcohol having an acid dissociation constant pKa of 13.0 or less (hereinafter also referred to as a "specific alcohol"). The composition comprises both the specific compound and the specific alcohol, and the specific compound comprises one or both of the compound represented by formula (1) and the compound represented by formula (2).

[0024] Although the reason why the composition having the above configuration can solve the problems of the present invention is not entirely clear, the inventors speculate as follows. Note that the following speculation does not limit the mechanism by which the effect is obtained. In other words, even if the effect is obtained by a mechanism other than the one described below, it is still within the scope of the present invention. The specific alcohol has an acid dissociation constant pKa of 13.0 or less, and protons are likely to dissociate from functional groups such as hydroxyl groups. The protons interact with the specific compound, which can improve the solubility of the specific compound. In such cases, it is speculated that the specific compound, which was previously difficult to purify, can be purified, resulting in excellent electric field strength dependence of the response speed of the resulting photoelectric conversion element. Hereinafter, a superior effect on the electric field strength dependence of the response speed of a photoelectric conversion element obtained using the composition of the present invention is also referred to as "excellent effect of the present invention."

[0025] <Specific Compound> The composition contains a specific compound. The specific compound is a compound selected from the group consisting of a compound represented by formula (1) and a compound represented by formula (2). The composition may contain both the compound represented by formula (1) and the compound represented by formula (2).

[0026] (Compound represented by formula (1))

[0027]

[0028] In formula (1), D １ represents a conjugated structure having at least one ring structure. １ The conjugated structure represented by the formula (1) is a structure in which a conjugated system is connected from one bonding position to the other bonding position. Specifically, when n1 is 2, the group in the square brackets in formula (1) is D １ From one of the positions where it is bonded to, the group in the other bracket is D １ In addition, when n1 is 3, the group in the square brackets in formula (1) is D １ This means that a conjugated system is connected between at least two of the three positions bonded to the above, as in the case of n1.

[0029] D １The conjugated structure represented by the formula (I) is not particularly limited as long as it is the above-mentioned conjugated structure. １ The conjugated structure represented by the formula (I) is preferably a monocyclic ring having a conjugated structure (hereinafter also simply referred to as a "conjugated monocyclic ring"), a fused ring having a conjugated structure (hereinafter also simply referred to as a "conjugated fused ring"), or two rings connected by a chain-like conjugated linking group (hereinafter also simply referred to as a "linked ring"), which will be described later. In addition, it may be a ring formed by combining two or more rings selected from the group consisting of a conjugated monocyclic ring, a conjugated fused ring, and a linked ring. Examples of the ring formed by combining two or more rings include -(Ar ｋ１ ) ｋ１ - is preferred. ｋ１ represents a conjugated monocyclic ring, a conjugated fused ring, or a linked ring. k1 represents an integer of 2 or more (preferably an integer of 2 to 6). Ar ｋ They may be the same or different.

[0030] The conjugated monocyclic ring, the conjugated fused ring, and the linked ring may have a substituent. Examples of the substituent include the groups exemplified for the substituent W above, and preferred are an alkyl group having 1 to 6 carbon atoms which may have a substituent, an alkoxy group having 1 to 6 carbon atoms which may have a substituent, an aryl group which may have a substituent, a halogen atom, a cyano group, or a primary, secondary, or tertiary amino group. The number of substituents that the conjugated monocyclic ring, the conjugated fused ring, and the linked ring may have is preferably 1 to 6, and more preferably 1 to 3.

[0031] Examples of conjugated monocycles include monocyclic aromatic rings. The conjugated monocycles may be either monocyclic aromatic hydrocarbon rings or monocyclic aromatic heterocycles. The number of ring atoms in the monocyclic aromatic ring is preferably 5 to 10, more preferably 5 or 6. The number of carbon atoms in the monocyclic aromatic ring is preferably 1 to 30, more preferably 3 to 20, and even more preferably 4 to 12. Examples of heteroatoms contained in the monocyclic aromatic heterocycles include sulfur atoms, oxygen atoms, nitrogen atoms, selenium atoms, tellurium atoms, phosphorus atoms, silicon atoms, boron atoms, and germanium atoms, with sulfur atoms, oxygen atoms, or nitrogen atoms being preferred. Examples of the monocyclic aromatic ring include a monocyclic aromatic hydrocarbon ring such as a benzene ring; and a monocyclic aromatic heterocycle such as a furan ring, a thiophene ring, a selenophene ring, a pyrrole ring, a thiazole ring, an isothiazole ring, a germole ring, a silole ring, an oxazole ring, an isoxazole ring, a thiadiazole ring, an oxadiazole ring, an imidazole ring, a pyrazole ring, an imidazole ring, a triazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, and a tetrazine ring; and a benzene ring, a furan ring, a thiophene ring, a selenophene ring, a germole ring, a silole ring, or a pyrrole ring is preferred.

[0032] Examples of the conjugated fused ring include a fused ring formed by combining two or more monocyclic rings. Two rings linked by a chain-like conjugated linking group are rings formed by linking two rings together via a chain-like conjugated linking group. The conjugated fused ring itself may or may not exhibit aromaticity. Examples of the monocyclic ring constituting the conjugated fused ring include a monocyclic aromatic ring and a monocyclic ring other than a monocyclic aromatic ring. Examples of the monocyclic aromatic ring include the monocyclic aromatic ring constituting the above-mentioned conjugated monocyclic ring. Examples of the other monocyclic ring include a non-aromatic ring and an anti-aromatic ring, and a cyclopentadiene ring, a cyclohexadiene ring, a cycloheptadiene ring, a cyclooctadiene ring, a silacyclopentadiene ring, a germacyclopentadiene ring, or a cyclopentane-1,3-dione ring are preferred. An aromatic ring is a ring having a π-electron system with 4n+2 electrons (n ​​is an integer of 0 or more), an anti-aromatic ring is a ring having a π-electron system with 4n electrons (n ​​is an integer of 1 or more), and a non-aromatic ring is a ring that does not satisfy the requirements of an aromatic ring or an anti-aromatic ring. Examples of conjugated fused rings having other monocyclic rings include fluorene rings and dibenzopentalene rings. Preferred conjugated fused rings include fused rings obtained by combining two or more (preferably, 2 to 4) monocyclic aromatic rings, fused rings obtained by combining one or more (preferably, 1 to 3) monocyclic aromatic rings with one or more (preferably, 1 to 3) rings other than monocyclic aromatic rings, and fused rings obtained by combining two or more (preferably, 2 to 4) rings other than monocyclic aromatic rings. In addition, the conjugated fused rings are those in which the atoms constituting the rings satisfy the relationship >C=P. Ｓ１ It may be: P Ｓ１ is an oxygen atom, a sulfur atom, =C(CN) ２ , =C[S(=O) ２ R ３Ｓ ] ２ , =C[S(=O)R ３Ｓ ] ２ ,=C[C(=O)R ３Ｓ ] ２ ,=C[CN][S(=O) ２ R ３Ｓ ], =C[CN][S(=O)R ３Ｓ ], =C[CN][C(=O)R ３Ｓ ], =C[C(=O)R３Ｓ ][S(=O) ２ R ３Ｓ ], =C[C(=O)R ３Ｓ ], or [S(=O)R ３Ｓ ]. ３Ｓ represents a substituent. ３Ｓ Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W.

[0033] As described above, the linked ring is a ring formed by linking two rings together with a chain-like conjugated linking group, and has a conjugated structure in which a conjugated system is connected from one bonding position to the other bonding position. Examples of the linked ring include -conjugated monocycle-chain-like conjugated linking group-conjugated monocycle-, -conjugated monocycle-chain-like conjugated linking group-conjugated fused ring-, and -conjugated fused ring-chain-like conjugated linking group-conjugated fused ring-. The definitions and preferred embodiments of the conjugated monocycle and conjugated fused ring contained in the linked ring are as described above. The chain-like conjugated linking group is a chain-like linking group that does not have a ring structure and has a conjugated structure in which a conjugated system is connected from one bonding position to the other bonding position. Examples of the chain-like conjugated linking group include chain-like linking groups having π electrons that can contribute to the conjugated system, such as alkenylene (-CR ｒ =CR ｒ -) group, an alkynylene group (-C≡C-), an azo group (-N=N-) or an imino group (-CR ｒ R is preferably an alkenylene group or an alkynylene group (—C≡C—), and more preferably an alkenylene group or an alkynylene group (—C≡C—). ｒ each independently represents a hydrogen atom or a substituent.

[0034] D １Examples of conjugated structures having at least one ring structure represented by the formula (a1) include the following structures. Examples of conjugated monocycles include monocycles represented by any of formulas (a1) to (a3). Examples of conjugated fused rings include fused rings formed by combining two or more monocycles selected from the group consisting of formulas (a1) to (a3); and fused rings formed by combining a monocycle selected from the group consisting of formulas (a1) to (a3) ​​with a fused ring represented by formula (a4). Examples of linked rings include rings formed by linking two rings selected from the above-mentioned conjugated monocycles and the above-mentioned conjugated fused rings with a chain-like conjugated linking group. In addition, in the monocycle represented by any of formulas (a1) to (a3), R Ｏ In the monocyclic ring represented by formula (a4), n1 represents a bonding position. Ｐ In the formula (a1), n1 represents a bonding position. In addition, in a fused ring formed by combining two or more monocycles selected from the group consisting of monocycles represented by any one of formulas (a1) to (a3), and in a fused ring formed by combining a monocycle selected from the group consisting of monocycles represented by any one of formulas (a1) to (a3) ​​with a fused ring of formula (a4), at least two or more =CR are present on an edge that is not shared by adjacent monocycles. Ｏ - is present and R Ｏ Among these, n1 represent bonding positions.

[0035] In addition, in a fused ring formed by combining two or more monocycles selected from the group consisting of formulas (a1) to (a3), and in a fused ring formed by combining a monocycle selected from the group consisting of formulas (a1) to (a3) ​​with a fused ring represented by formula (a4), adjacent rings are bonded to each other so as to share one side of each ring. For example, when the ring represented by formula (a1) is a benzene ring and the ring represented by formula (a2) is a thiophene ring, examples of the fused ring formed by combining one benzene ring and one thiophene ring are as follows:

[0036]

[0037]

[0038] In formulas (a1) to (a3), Y １６１ ~Y １６６ , Y １７１ ~Y １７４ , and Y １８１ ~Y １８４ are each independently: =CR Ｏ - or a nitrogen atom. Ｏ represents a hydrogen atom or a substituent. Ｏ The type of the substituent represented by is not particularly limited, and examples thereof include the groups exemplified for the substituent W described above, and a halogen atom, or an optionally substituted alkyl group, aryl group, or heteroaryl group is preferred.

[0039] In formula (a2), W １７１ represents an oxygen atom, a sulfur atom, a selenium atom, -NR Ｄ１ -, -SiR Ｄ２ ２ -, -GeR Ｄ３ ２ -, -CR Ｄ４ ２ - or > C=CR Ｄ５ ２ Represents R Ｄ１ ~R Ｄ５ R each independently represents a hydrogen atom or a substituent. Ｄ１ ~R Ｄ５ The type of the substituent represented by is not particularly limited, and examples thereof include the groups exemplified as the substituent W described later, and a halogen atom, or an optionally substituted alkyl group, aryl group, or heteroaryl group is preferred.

[0040] In formula (a3), V １８１ and V １８２ one of which is an oxygen atom, a sulfur atom, a selenium atom, or -NR Ｄ６ -, and the other is -CR ｃ２ ２ - represents. Ｄ６ The type of the substituent represented by R is not particularly limited, and examples thereof include the groups exemplified as the substituent W described below, and an alkyl group, an aryl group, or a heteroaryl group, which may have a substituent, is preferred. ｃ２ R each independently represents a hydrogen atom or a substituent. ｃ２The type of the substituent represented by is not particularly limited, and examples thereof include the groups exemplified as the substituent W described below, and an optionally substituted alkyl group, aryl group, or heteroaryl group is preferred.

[0041] In formula (a4), Y ２３１ ~Y ２３６ are each independently: =CR Ｐ - or a nitrogen atom. Ｐ represents a hydrogen atom or a substituent. Ｐ The type of the substituent represented by is not particularly limited, and examples thereof include the groups exemplified for the substituent W above, and a halogen atom, or an optionally substituted alkyl group, aryl group, or heteroaryl group is preferred.

[0042] D １ Specific examples of the conjugated structure represented by the formula are shown below. * represents a bonding position. Note that all of the groups shown below are divalent groups, and when n1 is 2, D １ On the other hand, when n1 is 3, １ Specific examples of this aspect include trivalent groups formed by removing one hydrogen atom from the divalent groups exemplified below. In the following formulae, each 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 １ each independently represents an oxygen atom, a sulfur atom, a selenium atom, or —NR Ｄ１ -, -SiR Ｄ２ ２ -, -GeR Ｄ３ ２ -, -CR Ｄ４ ２ - or > C=CR Ｄ５ ２ Represents R Ｄ１ ~R Ｄ５ The definition of is as described above.

[0043]

[0044]

[0045]

[0046]

[0047] In formula (1), n1 represents 2 or 3. n1 is preferably 2.

[0048] In formula (1), m1 represents 0 or 1. Each m1 may be the same or different.

[0049] In formula (1), A １ represents a group represented by formula (A-1) or a group represented by formula (A-2). １ They may be the same or different.

[0050]

[0051] In formula (A-1), * represents a bonding position.

[0052] In formula (A-1), C １ is one or more carbon atoms and X Ｙ The above C represents a ring containing the above C １ The one carbon atom contained in the ring is one carbon atom specified in formula (A-1). The number of carbon atoms in the ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10. The number of carbon atoms in the ring is the number including one carbon atom specified in the formula, and X Ｙ GA>C=Y １ In the case where C is a carbon atom, the number includes one carbon atom specified in the formula and the carbon atom in >C=. The ring may be either an aromatic ring or a non-aromatic ring. The ring may be either a monocyclic or polycyclic ring, and is preferably a 5-membered ring, a 6-membered ring, or a fused ring containing at least one of a 5-membered ring and a 6-membered ring. The number of carbon atoms in the fused ring containing at least one of a 5-membered ring and a 6-membered ring is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 10.

[0053] Examples of the substituent that the ring may have include the groups exemplified by the substituent W. The ring may also have a heteroatom. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, with a sulfur atom, a nitrogen atom, or an oxygen atom being preferred. The number of heteroatoms in the ring is preferably 0 to 10, and more preferably 0 to 5. The C １ Among the carbon atoms constituting the ring represented by the formula (A-1), the carbon atom at the bonding position marked with * and Y １ The carbon atom other than the carbon atom bonded to may be a carbonyl carbon or a thiocarbonyl carbon. Note that a "carbonyl carbon" refers to a carbon atom in a carbonyl group (-C=O), and a "thiocarbonyl carbon" refers to a carbon atom in a thiocarbonyl group (-C=S).

[0054] Above C １The ring represented by the formula (I) is preferably a ring used as an acidic nucleus (for example, the acidic nucleus in a merocyanine dye), and examples thereof include the following nuclei: (a) 1,3-dicarbonyl nucleus: for example, a 1,3-indandione nucleus, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, and 1,3-dioxane-4,6-dione; (b) pyrazolinone nucleus: for example, 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, and 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one; (c) isoxazolinone nucleus: for example, 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one; (d) oxindole nucleus: for example, 1-alkyl-2,3-dihydro-2-oxindole; (e) 2,4,6-trioxohexahydropyrimidine nucleus: for example, barbituric acid, 2-thiobarbituric acid, and derivatives thereof. Examples of the derivatives include 1-alkyl compounds such as 1-methyl and 1-ethyl, 1,3-dialkyl compounds such as 1,3-dimethyl, 1,3-diethyl, and 1,3-dibutyl, 1,3-diaryl compounds such as 1,3-diphenyl, 1,3-di(p-chlorophenyl), and 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1-aryl compounds such as 1-ethyl-3-phenyl, and 1,3-diheteroaryl compounds such as 1,3-di(2-pyridyl). (f) 2-thio-2,4-thiazolidinedione nucleus: for example, rhodanine and derivatives thereof. Examples of the derivatives include 3-alkylrhodanines such as 3-methylrhodanine, 3-ethylrhodanine, and 3-allylrhodanine, 3-arylrhodanines such as 3-phenylrhodanine, and 3-heteroarylrhodanines such as 3-(2-pyridyl)rhodanine. (g) 2-thio-2,4-oxazolidinedione nucleus (2-thio-2,4-(3H,5H)-oxazoledione nucleus): for example, 3-ethyl-2-thio-2,4-oxazolidinedione. (h) thianaphthenone nucleus: for example, 3(2H)-thianaphthenone-1,1-dioxide. (i) 2-thio-2,5-thiazolidinedione nucleus: for example, 3-ethyl-2-thio-2,5-thiazolidinedione.(j) 2,4-thiazolidinedione nucleus: for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione. (k) thiazolin-4-one nucleus: for example, 4-thiazolinone and 2-ethyl-4-thiazolinone. (l) 2,4-imidazolidinedione (hydantoin) nucleus: for example, 2,4-imidazolidinedione and 3-ethyl-2,4-imidazolidinedione. (m) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus: for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidinedione. (n) Imidazolin-5-one nucleus: for example, 2-propylmercapto-2-imidazolin-5-one, etc. (o) 3,5-pyrazolidinedione nucleus: for example, 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione, etc. (p) Benzothiophen-3(2H)-one nucleus: for example, benzothiophen-3(2H)-one, oxobenzothiophen-3(2H)-one, and dioxobenzothiophen-3(2H)-one, etc. (q) Indanone nucleus: for example, 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone, and 3,3-dimethyl-1-indanone, etc. (r) Benzofuran-3-(2H)-one nucleus: for example, benzofuran-3-(2H)-one, etc. (s) 2,2-dihydrophenalene-1,3-dione nucleus, etc.

[0055] In formula (A-1), X Ｙ is >C=Y １ Or > N-Y ２ Represents Y. ２ represents a hydrogen atom or a substituent. Examples of the substituent include the substituents exemplified for the substituent W, and an alkyl group, an aryl group, or a heteroaryl group, which may have a substituent, is preferred. X Ｙ As such, >C=Y １ is preferred.

[0056] In formula (A-1), Y １ represents an oxygen atom, a sulfur atom, and ═NR Ｙ１ , or =CR Ｙ２ RＹ３ Represents Y. １ is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom. Ｙ１ represents a hydrogen atom or a substituent. １ Ga = NR Ｙ１ represents C １ represents a ring containing one or more carbon atoms and having a substituent, R Ｙ１ And, C １ and the substituents of the ring represented by R may be bonded to each other to form a ring. Examples of the substituent include the substituents exemplified for the substituent W above. Ｙ１ And, C １ The ring formed by bonding together with the substituents of the ring represented by R may be either a monocyclic ring or a polycyclic ring. Ｙ１ And, C １ When the group represented by formula (A-1) is formed by bonding with a substituent carried by a ring represented by formula (A-2), the group represented by formula (A-1) is preferably a fused ring of 2 to 5 rings, more preferably a fused ring of 2 or 3 rings. The fused ring is preferably a fused ring formed by condensing a plurality of rings selected from aromatic rings and non-aromatic rings, more preferably a fused ring formed by condensing an aromatic ring with one or more rings selected from aromatic rings and non-aromatic rings. R Ｙ１ And, C １ When the substituents on the ring represented by the formula (A-1) are bonded to each other to form a ring, the group represented by the formula (A-1) is preferably a group represented by the formula (Q1).

[0057]

[0058] In formula (Q1), * represents a bonding position. Ｂ is -N<, >C=, or -CQ Ｙ < represents. Q Ｙ represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified as the substituent W. Ｂ is preferably -N< or >C=, and more preferably -N<.

[0059] In formula (Q1), B ２ is composed of two carbon atoms and Q ＢThe two carbon atoms represent the two carbon atoms specified in the formula. ２ For example, C １ Examples of the ring include those represented by the following formula:

[0060] In formula (A-1), R Ｙ２ and R Ｙ３ each independently represents a cyano group, —SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents R Ｙ４ ~R Ｙ６ R each independently represent an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. The definition of the aliphatic hydrocarbon group is as described above, and an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred. The definition of the aromatic ring group is as described above, and an aromatic hydrocarbon group is preferred, and a phenyl group is more preferred. The definition of the aliphatic heterocyclic group is as described above, and the heteroatom contained in the aliphatic heterocyclic group is preferably an oxygen atom, a sulfur atom, or a nitrogen atom. R Ｙ４ ~R Ｙ６ Examples of the substituent that each group represented by the following formula may have include the substituents exemplified for the substituent W above.

[0061] In formula (A-2), * represents a bonding position. Ａ１ and R Ａ２ each independently represents a cyano group, —SO ２ R Ｘ１ , -COOR Ｘ２ , or -COR Ｘ３ Represents R Ｘ１ ~R Ｘ３ R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ａ１ and R Ａ２ The group may be a cyano group or -COR Ｘ３ is preferred. Ｘ１ ~R Ｘ３ The definitions and preferred embodiments of each group represented by R Ｙ４ ~RＹ６ and an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a phenyl group is preferred.

[0062] In formula (1), A １ As the alkyl group, a group represented by the above formula (A-1) is preferable, a group represented by the formula (A-3) is more preferable, and a group represented by the formula (C-1) or a group represented by the formula (C-2) is even more preferable.

[0063]

[0064] In formula (A-3), * represents a bonding position. ２ represents a ring containing 3 or more carbon atoms and which may have a substituent. ２ The three carbon atoms contained in the formula (A-3) are the three carbon atoms specified in the formula (A-3), and C ２ may further contain carbon atoms other than the three carbon atoms. The number of carbon atoms in the ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10. The number of carbon atoms in the ring is the number including the three carbon atoms specified in the formula. The ring may be either an aromatic ring or a non-aromatic ring. The ring may be either a monocyclic or polycyclic ring, and is preferably a 5-membered ring, a 6-membered ring, or a fused ring containing at least one of a 5-membered ring and a 6-membered ring. The number of carbon atoms in the fused ring containing at least one of a 5-membered ring and a 6-membered ring is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 10. The ring may contain a heteroatom. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, a nitrogen atom, or an oxygen atom is preferred. The number of heteroatoms in the ring is preferably 0 to 10, and more preferably 0 to 5. The C ２ Among the carbon atoms constituting the ring represented by the formula (A-3), the carbon atom at the bonding position marked with * and W ２ Or W ３ The carbon atom other than the carbon atom bonded to may be a carbonyl carbon or a thiocarbonyl carbon. １ The substituents are the same as those that may be possessed by the group.

[0065] In formula (A-3), W ２ and W ３ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents R Ｙ１ ~R Ｙ３ represents R in formula (A-1). Ｙ１ ~R Ｙ３ The preferred embodiments are also the same as those of the above. ２ and W ３ are each independently preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0066]

[0067] In formula (C-1), * represents a bonding position. ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｃ１ or =CR Ｃ２ R Ｃ３ The effect of the present invention is more excellent, and therefore, X ｃ１ and X ｃ２ Preferably, at least one of X is an oxygen atom, ｃ１ and X ｃ２ It is more preferable that R is an oxygen atom. Ｃ１ represents a hydrogen atom or a substituent. Examples of the substituent include the substituents exemplified above for the substituent W. Ｃ２ and R Ｃ３ each independently represents a cyano group, —SO ２ R Ｃ４ , -COOR Ｃ５ , or -COR Ｃ６ Represents R Ｃ４ ~R Ｃ６ R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. Ｃ４ ~R Ｃ６ The definitions and preferred embodiments of each group represented by R Ｙ４ ~R Ｙ６Among these, an aliphatic hydrocarbon group having 1 to 4 carbon atoms or a phenyl group is preferred.

[0068] In formula (C-1), C ３ represents an aromatic ring containing two or more carbon atoms and which may have a substituent. The aromatic ring may be either a monocyclic or polycyclic ring, but a monocyclic ring is preferred. The number of ring members in the aromatic ring is preferably 4 to 30, more preferably 5 to 12, and even more preferably 5 to 8. The number of ring members in the aromatic ring is the number including the two carbon atoms specified in the formula. Furthermore, the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but an aromatic hydrocarbon ring is preferred. C ３ The aromatic ring represented by the formula (I) is preferably a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a thiophene ring, a furan ring, a thiazole ring, an oxazole ring, a pyridine ring, a thienothiophene ring, a benzothiophene ring, a benzofuran ring, a pyrazine ring, a pyrimidine ring, a thienothiophene ring, or a pyridazine ring, more preferably a benzene ring, a naphthalene ring, or a thiophene ring, and even more preferably a benzene ring. Examples of the substituent that the aromatic ring may have include the groups exemplified by the substituent W, and an alkyl group or a halogen atom is preferred. The number of substituents that the aromatic ring may have is not particularly limited, but is preferably 0 to 8, and more preferably 0 to 4.

[0069] In the above formula (C-2), X ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｃ１ or =CR Ｃ２ R Ｃ３ The effect of the present invention is more excellent, and therefore, X ｃ３ and X ｃ４ is preferably an oxygen atom, and X ｃ３ ~X ｃ５ It is more preferable that R is an oxygen atom. Ｃ１ ~R Ｃ３ The definition and preferred embodiments of are as described above.

[0070] In the above formula (C-2), Z ｃ１ and Z ｃ２ are each independently -NR Ｃ７ -or-CRＣ８ ２ - represents. Ｃ７ and R Ｃ８ each independently represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified by the substituent W above, with an alkyl group or an aryl group being preferred, and an alkyl group being more preferred. The alkyl group may be linear, branched, or cyclic, with a linear group being preferred. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 6, even more preferably 1 to 3, and particularly preferably 1 or 2. The aryl group may be monocyclic or polycyclic, with a phenyl group being preferred. The aryl group may further have a substituent, and examples of the substituent include the groups exemplified by the substituent W above.

[0071] Specific examples of the group represented by formula (A-1) are shown below, where * indicates the bonding position.

[0072]

[0073]

[0074]

[0075] Specific examples of the group represented by formula (A-2) are shown below, where * indicates the bonding position.

[0076]

[0077]

[0078] The compound represented by formula (1) is preferably a compound represented by formula (1-1).

[0079]

[0080] In formula (1-1), ring A and ring B each independently represent a conjugated monocyclic ring, a conjugated fused ring, or a linked ring. １Examples of the conjugated monocyclic ring include a conjugated monocyclic ring and a conjugated fused ring which form a conjugated structure represented by the formula: The conjugated monocyclic ring is preferably an aromatic six-membered ring, a conjugated five-membered ring, or a non-aromatic conjugated six-membered ring. The conjugated five-membered ring is a five-membered ring having a conjugated structure, and the non-aromatic conjugated six-membered ring is a non-aromatic six-membered ring having a conjugated structure. Examples of the aromatic six-membered ring include D １ Among the conjugated monocyclic rings constituting the conjugated structure represented by the formula (a1), a six-membered ring exhibiting aromaticity is preferred, and an aromatic six-membered ring having an atom selected from the group consisting of carbon atoms and nitrogen atoms as a ring member atom is more preferred. When the aromatic six-membered ring has a nitrogen atom, the number of nitrogen atoms is preferably 1 to 5, more preferably 1 to 3. A more specific structure of the aromatic six-membered ring includes a monocyclic ring represented by the formula (a1). Examples of the conjugated five-membered ring include D １ Among the conjugated monocyclic rings constituting the conjugated structure represented by the formula: Ｄ１ -, -SiR Ｄ２ ２ -, -GeR Ｄ３ ２ -, -CR Ｄ４ ２ - and >C=CR Ｄ５ ２ More preferably, the ring is an aromatic five-membered ring in which an atom or structure selected from the group consisting of R Ｄ１ ~R Ｄ５ R each independently represents a hydrogen atom or a substituent. Ｄ１ ~R Ｄ５ is R in formula (a2). Ｄ１ ~R Ｄ５ The preferred embodiments are also the same. A more specific structure of the conjugated five-membered ring is a monocycle represented by formula (a2). Examples of the non-aromatic conjugated six-membered ring include D １ Among the conjugated monocyclic rings constituting the conjugated structure represented by the formula: Ｄ１ -Y Ｄ２ A non-aromatic conjugated 6-membered ring in which - constitutes a ring is more preferred. Ｄ１ and Y Ｄ２ one of which is an oxygen atom, a sulfur atom, a selenium atom, or -NR Ｄ６ -, and the other is -CR ｃ２ ２ represents -, and RＤ６ represents a hydrogen atom or a substituent, R ｃ２ represents a hydrogen atom or a substituent. Ｄ１ , Y Ｄ２ , R Ｄ６ and R ｃ２ are V in formula (a3), respectively. １８１ , V １８２ , R Ｄ６ and R ｃ２ The same applies to the preferred embodiments. When a plurality of rings B are present, the rings B may be the same or different. A more specific structure of the non-aromatic conjugated 6-membered ring is a monocycle represented by formula (a3).

[0081] The conjugated fused rings include D １ and more preferably a fused ring formed by condensing a plurality of rings selected from the group consisting of the above-mentioned aromatic six-membered ring, the above-mentioned aromatic five-membered ring, and the above-mentioned non-aromatic six-membered ring.

[0082] The connecting ring is D １ Preferably, the linked ring forming the conjugated structure represented by the following formula is used.

[0083] In formula (1-1), A １ each independently represents a group represented by formula (A-1) or a group represented by formula (A-2). １ is A in formula (1) １ Each m1 independently represents 0 or 1. o1 represents an integer of 0 to 2. o1 is preferably 0 or 1.

[0084] (Compound represented by formula (2))

[0085]

[0086] In formula (2), D ２ represents a structure having at least one ring structure. ２ The structure represented by the formula (I) may be either a conjugated structure or a non-conjugated structure, and a conjugated structure is preferred. ２ As the conjugated structure represented by １ When n2 is 2 or 3, D２ The conjugated structure represented by D １ On the other hand, when n2 is 1, the group in the square brackets in formula (2) is bonded to D ２ and a ring atom D adjacent to the adjacent ring atom is further adjacent to the ring atom D to which the group in the square brackets in formula (2) is bonded. ２ It is preferable that the conjugated system extends to the ring atom on the opposite side of the ring atom of D ２ It is more preferable that the conjugated system is connected to the entire ring structure of D. ２ The non-conjugated structure represented by the formula (I) is not particularly limited as long as it has at least one ring structure and is a structure other than a conjugated structure. １ Examples of the monocyclic ring having a non-conjugated structure include a non-conjugated structure formed by combining rings constituting a conjugated structure represented by the formula: １ Examples of the fused ring having a non-conjugated structure include other single rings that can form a conjugated structure represented by the formula: １ Examples of the aromatic ring include a fused ring formed by combining other monocyclic rings and monocyclic aromatic rings, which can form a conjugated structure represented by the following formula:

[0087] D ２ Specific examples of the structure represented by the formula (I) include the above-mentioned D １ and the following structure: * represents a bonding position.

[0088]

[0089] In formula (2), n2 represents an integer of 1 to 3. n2 is preferably 1 or 2. m2 represents 0 or 1. m2 is preferably 0. m2 may be the same or different from each other. A ２ represents a group represented by formula (A-1) or a group represented by formula (A-2). ２ A １ The same definition and preferred embodiments are also the same. ２ They may be the same or different.

[0090] The compound represented by formula (2) is preferably a compound represented by formula (2-1).

[0091]

[0092] In formula (2-1), ring C represents a conjugated monocyclic ring or a conjugated fused ring. Examples of ring C include the above-mentioned ring A and ring B, and a conjugated fused ring is preferable, and a conjugated fused ring formed by condensing a plurality of rings selected from the group consisting of the above-mentioned aromatic six-membered ring and the above-mentioned non-aromatic conjugated six-membered ring is more preferable. Ring C is also preferably a benzene ring, a naphthalene ring, a quinoxaline ring, or a pyrazine ring.

[0093] In formula (2-1), A ２ represents a group represented by formula (A-1) or a group represented by formula (A-2). ２ A １ m2 represents 0 or 1. X １ and X ２ One of them is -NR Ｎ -, and the other represents a sulfur atom, an oxygen atom, a selenium atom, or -NR Ｎ -or-CR ｃ１ ２ - represents. Ｎ represents a hydrogen atom or a substituent. ｃ１ represents a hydrogen atom or a substituent. １ and X ２ One of them is -NR Ｎ -, and the other represents -NR Ｎ -or-CR ｃ１ ２ -, and X １ and X ２ Ga-NR Ｎ It is more preferable that R represents -. Ｎ and R ｃ１ Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W, and an alkyl group which may have a substituent or an aryl group which may have a substituent is preferred, and an alkyl group having 1 to 5 carbon atoms or an aryl group which may have an alkyl group having 1 to 5 carbon atoms is more preferred.

[0094] Examples of the specific compound include the following compounds. Specific examples of the specific compound other than the following compounds include the above-mentioned D １ and D ２ * (bonding position) in the groups shown as specific examples of A １ and A ２ Also included are compounds in which * (bonding position) in the groups shown as specific examples is bonded via *1-CH=*2. １ or D ２ *2 is combined with * on the side １ or A ２ Combine with the * on the side.

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] The molecular weight of the specific compound is preferably 300 to 1200, more preferably 350 to 1000, and even more preferably 400 to 800. When the molecular weight is within the above range, the sublimation temperature of the specific compound is lowered, and it is presumed that the specific compound has excellent suitability for production.

[0105] The maximum absorption wavelength of the specific compound is preferably in the wavelength range of 400 to 600 nm, more preferably in the range of 450 to 600 nm. The maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) after adjusting the absorption spectrum of the specific compound to a concentration such that the absorbance is 0.5 to 1.0. However, if the specific compound is insoluble in chloroform, the maximum absorption wavelength of the specific compound is determined by evaporating the specific compound and measuring the value using the specific compound in a film state.

[0106] The specific compound is particularly useful as a material for a photoelectric conversion film used in an imaging device, an optical sensor, or a photovoltaic cell. The specific compound often functions as a dye in the photoelectric conversion film. The specific compound can also be used as a coloring material, a liquid crystal material, an organic semiconductor material, a charge transport material, a pharmaceutical material, and a fluorescent diagnostic material.

[0107] The content of the specific compound in the composition of the present invention is preferably from 0.1 to 30% by mass, more preferably from 0.3 to 25% by mass, based on the total mass of the composition.

[0108] <Specific Alcohol> The composition contains a specific alcohol. The specific alcohol is an alcohol having an acid dissociation constant pKa of 13.0 or less. The acid dissociation constant pKa of the specific alcohol is 13.0 or less, and is preferably 10.0 or less in terms of better effects of the present invention. The lower limit of the acid dissociation constant pKa of the specific alcohol is preferably 0 or more, more preferably 4.0 or more, even more preferably 5.0 or more, and particularly preferably 6.0 or more. Note that, when one functional group (e.g., an acidic functional group such as a hydroxyl group) in the specific alcohol has multiple acid dissociation constants pKa, the lowest acid dissociation constant pKa among the multiple acid dissociation constants pKa may be 13.0 or less. Specifically, when one functional group in a certain alcohol has three acid dissociation constants pKa: a first acid dissociation constant pKa of 1.0, a second acid dissociation constant pKa of 5.0, and a third acid dissociation constant pKa of 15.0, the alcohol is classified as a specific alcohol because the lowest first acid dissociation constant pKa is 13.0 or less. Furthermore, when a specific alcohol has multiple functional groups, if the acid dissociation constant pKa of at least one of the multiple functional groups is 13.0 or less, the alcohol is classified as a specific alcohol. The acid dissociation constant pKa is preferably the acid dissociation constant pKa of the hydroxy group in the specific alcohol. The acid dissociation constant pKa is not particularly limited and can be measured by a known method. For example, it can be measured by the values ​​or methods described in Chemical Support Series, Acids and Bases (Shokabo), J. Am. Chem. Soc. 1936, 58, 7, 1124-1129, J. Am. Chem. Soc. 1952, 74, 21, 5266-5271, J. Am. Chem. Soc. 1960, 82, 4, 795-798, J. Am. Chem. Soc. 1959, 81, 5, 1050-1053.

[0109] The specific alcohol is a compound having a hydroxy group. The number of hydroxy groups contained in the specific alcohol is not particularly limited and may be 1 or 2 or more, preferably 1 to 3, and more preferably 1. The specific alcohol may have a substituent other than a hydroxy group. The number of substituents (preferably the number of halogen atoms) other than the hydroxy group that the specific alcohol may have is not particularly limited and may be 1 or 2 or more, preferably 1 to 15, and more preferably 3 to 10. Examples of the substituent include the groups exemplified for the substituent W above. An alkyl group, an alkenyl group, a halogen atom, a carboxy group, an aryl group, or a cyano group is preferred, an aryl group or a halogen atom is preferred, a fluorine atom or a chlorine atom is more preferred, and a fluorine atom is even more preferred. In particular, it is preferable that the specific alcohol has a halogen atom, as this makes it easier to adjust the acid dissociation constant pKa to 13 or less, and it is more preferable that at least one carbon atom at the β-position of the hydroxy group contained in the specific alcohol has a halogen atom. The specific alcohol preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 3 to 10 carbon atoms, in terms of achieving better effects of the present invention.

[0110] In terms of obtaining better effects of the present invention, the specific alcohol is preferably an alcohol represented by formula (S1), more preferably an alcohol represented by formula (S2), and even more preferably an alcohol represented by formula (S3).

[0111]

[0112] In formula (S1), R Ｓ１ ~R Ｓ６ each independently represents a hydrogen atom or a substituent, R Ｓ１ ~R Ｓ６ At least one of R represents a fluorine atom. Ｓ７ represents a hydrogen atom or a substituent.

[0113] R Ｓ１ ~R Ｓ６ Examples of the substituent represented by R include the groups exemplified as the substituent W above, and a halogen atom is preferred, with a chlorine atom or a fluorine atom being more preferred. Ｓ１ ~R Ｓ３At least one (preferably two or three) of R represents a fluorine atom, and Ｓ４ ~R Ｓ６ Preferably, at least one (preferably, two or three) of R represents a fluorine atom, Ｓ１ ~R Ｓ６ More preferably, all of R represent a fluorine atom. Ｓ７ Examples of the substituent represented by R include the groups exemplified as the substituent W above, and an alkyl group, an alkenyl group, a carboxy group, an aryl group, or a hydroxy group is preferred, and an alkyl group which may have a halogen atom, or an aryl group is more preferred. Ｓ７ is preferably a hydrogen atom, an alkyl group which may have a halogen atom, or an aryl group.

[0114]

[0115] In formula (S2), R Ｓ１ ~R Ｓ３ each independently represents a hydrogen atom or a substituent, R Ｓ１ ~R Ｓ３ At least one of R represents a fluorine atom. Ｓ７ represents a hydrogen atom or a substituent.

[0116] R in formula (S2) Ｓ１ ~R Ｓ３ are R in formula (S1), respectively. Ｓ１ ~R Ｓ３ The meaning and preferred embodiments are also the same. Ｓ７ is R in formula (S1) Ｓ７ The same definition and preferred embodiments are also the same.

[0117]

[0118] In formula (S3), R Ｓ７ represents a hydrogen atom or a substituent. Ｓ７ is R in formula (S1) Ｓ７ The same definition and preferred embodiments are also the same.

[0119] Examples of the specific alcohol include hexafluoroisopropanol, 2,2,2-trifluoroethanol, 2,2,2-trichloroethanol, 1,1,1,3,3,3-hexafluoro-2-methyl-2-propanol, nonafluoro-tert-butyl alcohol, and 1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanol.

[0120] The specific alcohols also include the following alcohols:

[0121]

[0122]

[0123] The specific alcohol may be used alone or in combination of two or more. The content of the specific alcohol is preferably 0.01 to 99% by mass, more preferably 0.1 to 90% by mass, and even more preferably 1 to 50% by mass, based on the total mass of the composition.

[0124] <Organic Solvent> The composition may contain an organic solvent other than the specific alcohol described above.

[0125] The organic solvent is preferably a hydrocarbon which may have a substituent. The hydrocarbon may be either an aliphatic hydrocarbon or an aromatic hydrocarbon. The hydrocarbon preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 1 to 10 carbon atoms. Examples of the substituent that the hydrocarbon may have include the groups exemplified for the substituent W above, and a halogen atom or an alkoxy group is preferable, and a halogen atom is more preferable. The number of substituents is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.

[0126] Examples of hydrocarbons which may have a substituent include halogenated aliphatic hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, tetrachloroethane, pentachloroethane, hexachloroethane, hexachloropropane, bromomethane, dibromomethane, tribromomethane, tetrabromoethane, pentabromoethane, and hexabromoethane; halogenated aromatic hydrocarbons such as chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, dichlorotoluene, trichlorobenzene, ethylchlorobenzene, and 1-tert-butoxy-4-chlorobenzene; pentane, cyclopentane, hexane, cyclohexyl hexane, and cyclohexyl hexane. saturated aliphatic hydrocarbons such as hexane, methylcyclohexane, octane, nonane, decane, undecane, dodecane, hexadecane, 2,2,4-trimethylpentane, 2,2,3-trimethylhexane, and decahydronaphthalene; aromatic hydrocarbon solvents such as mesitylene, cumene, pseudocumene, 1,2,4,5-tetramethylbenzene, p-cymene, toluene, xylene, ethylbenzene, propylbenzene, 1-methylpropylbenzene, 2-methylpropylbenzene, dimethylbenzene, diethylbenzene, ethylmethylbenzene, trimethylbenzene, ethyldimethylbenzene, dipropylbenzene, 1-chloronaphthalene, and 1-methylnaphthalene; benzothiophene and benzofuran.

[0127] The organic solvent is preferably composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, oxygen atoms, and halogen atoms, and more preferably composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, and halogen atoms, in terms of better effects of the present invention.

[0128] The organic solvent may be used alone or in combination of two or more. The content of the organic solvent is preferably 0 to 99% by mass, more preferably 1 to 90% by mass, and even more preferably 10 to 80% by mass, relative to the total mass of the composition. The content of the specific alcohol relative to the total content of the specific alcohol and the organic solvent (specific alcohol content / total content of the specific alcohol and the organic solvent) is preferably 0.01% by volume or more, more preferably 1% by volume or more, and from the viewpoint of more excellent effects of the present invention, more preferably 10% by volume, and particularly preferably 15% by volume or more. The upper limit is preferably less than 100% by volume, more preferably 99% by volume or less, and even more preferably 95% by volume or less.

[0129] The total content of the specific alcohol and the organic solvent other than the specific alcohol in the composition of the present invention is preferably 70 to 99.9 mass %, more preferably 75 to 99.7 mass %, based on the total mass of the composition.

[0130] <Other Components> The composition may contain other components in addition to the various components described above. Examples of other components include known additives.

[0131] The composition of the present invention is preferably used for producing a photoelectric conversion element, and more preferably used for forming a photoelectric conversion film included in the photoelectric conversion element.

[0132] [Photoelectric Conversion Element] The photoelectric conversion element of the present invention is preferably a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order. FIG. 1 shows a cross-sectional schematic diagram of one embodiment of the photoelectric conversion element of the present invention. The photoelectric conversion element 10a shown in FIG. 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 functioning as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and a transparent conductive film (hereinafter also referred to as the "upper electrode") 15 functioning as an upper electrode are stacked in this order. FIG. 2 shows an example of the configuration of another photoelectric conversion element. The photoelectric conversion element 10b shown in FIG. 2 has a configuration in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are stacked in this order on the lower electrode 11. The stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in FIGS. 1 and 2 may be changed as appropriate depending on the application and characteristics.

[0133] In the photoelectric conversion element 10a (or 10b), it is preferable that light is incident on the photoelectric conversion film 12 through the upper electrode 15. When the photoelectric conversion element 10a (or 10b) is used, a voltage can be applied. In this case, the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and a voltage of 1×10 is applied between the pair of electrodes. －５ ~1 x 10 ７ In terms of performance and power consumption, it is preferable to apply a voltage of 1×10 V / cm. －４ ~1 x 10 ７ V / cm is more preferable, and 1×10 －３ ~5 x 10 ６ V / cm is more preferable. Regarding the voltage application method, it is preferable to apply the voltage so that the electron blocking film 16A side serves as the cathode and the photoelectric conversion film 12 side serves as the anode in FIGS. 1 and 2. When the photoelectric conversion element 10a (or 10b) is used as a photosensor or incorporated into an imaging element, a voltage can be applied in a similar manner. As will be described in detail later, the photoelectric conversion element 10a (or 10b) can be suitably used as an imaging element. The configuration of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.

[0134] [Photoelectric Conversion Film] The photoelectric conversion element preferably has a photoelectric conversion film. The photoelectric conversion film is preferably formed using the specific compound obtained from the composition of the present invention. The photoelectric conversion film contains the specific compound described above, and may also contain at least one selected from the group consisting of the specific alcohol described above, the organic solvent described above, and the other components described above.

[0135] The content of the specific compound in the photoelectric conversion film (=film thickness of the specific compound in terms of a single layer / film thickness of the photoelectric conversion film × 100) is not particularly limited, but is preferably 15 to 75% by volume, more preferably 20 to 60% by volume, and even more preferably 20 to 50% by volume. Only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is in the above range.

[0136] <n-Type Organic Semiconductor> The photoelectric conversion film preferably further contains an n-type organic semiconductor in addition to the specific compound. The n-type organic semiconductor is a compound different from the specific compound. The n-type organic semiconductor is an acceptor organic semiconductor material (compound) and refers to an organic compound that has the property of easily accepting electrons. In other words, the n-type organic semiconductor refers to the organic compound that has a larger electron affinity when two organic compounds are used in contact with each other. In other words, any organic compound can be used as the acceptor organic semiconductor as long as it is an organic compound with electron-accepting properties. Examples of n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof; fused aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); and 5- to 7-membered heterocyclic compounds having at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole, and thiazole). polyarylene compounds; fluorene compounds; cyclopentadiene compounds; silyl compounds; 1,4,5,8-naphthalenetetracarboxylic acid anhydride; 1,4,5,8-naphthalenetetracarboxylic acid diimide derivatives; anthraquinodimethane derivatives; diphenylquinone derivatives; bathocuproine, bathophenanthroline, and derivatives thereof; triazole compounds; distyrylarylene derivatives; metal complexes having a nitrogen-containing heterocyclic compound as a ligand; silole compounds; 3,4,9,10-perylenetetracarboxylic acid dianhydride; 3,4,9,10-perylenetetracarboxylic acid diimide derivatives; and the compounds described in paragraphs

[0056] to

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

[0137] As the n-type organic semiconductor (compound), fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred. For example, fullerene C ６０ , fullerene C ７０, fullerene C ７６ , fullerene C ７８ , fullerene C ８０ , fullerene C ８２ , fullerene C ８４ , fullerene C ９０ , fullerene C ９６ , fullerene C ２４０ , fullerene C ５４０ and mixed fullerenes. Examples of fullerene derivatives include compounds in which a substituent is added to the above-mentioned fullerenes. The substituent is preferably an alkyl group, an aryl group, or a heterocyclic group. Preferred fullerene derivatives are the compounds described in JP-A-2007-123707.

[0138] The n-type organic semiconductor may be an organic dye. Examples of the organic dye include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarylium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, acridine dyes, acridinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes, and metal complex dyes.

[0139] The molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.

[0140] The maximum absorption wavelength of the n-type organic semiconductor is preferably in the range of 400 nm to 600 nm.

[0141] The photoelectric conversion film preferably has a bulk heterostructure formed by mixing a specific compound and an n-type organic semiconductor. The bulk heterostructure is a layer in the photoelectric conversion film in which the specific compound and the n-type organic semiconductor are mixed and dispersed. The photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. The bulk heterostructure is described in detail in paragraphs

[0013] to

[0014] of JP 2005-303266 A.

[0142] The difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.

[0143] When the photoelectric conversion film contains an n-type organic semiconductor, the content of the n-type organic semiconductor in the photoelectric conversion film (thickness of the n-type organic semiconductor in terms of a single layer / thickness of the photoelectric conversion film × 100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 20 to 50 vol%.

[0144] When the n-type organic semiconductor contains fullerenes, the content of the fullerenes relative to the total content of the n-type organic semiconductors (film thickness of fullerenes converted into a single layer / total film thickness of each n-type organic semiconductor converted into a single layer × 100) is preferably 50 to 100% by volume, more preferably 80 to 100% by volume. Fullerenes may be used singly or in combination of two or more types.

[0145] In terms of the response speed of the photoelectric conversion element, the content of the specific compound relative to the total content of the specific compound and the n-type organic semiconductor (film thickness in monolayer equivalent of the specific compound / (film thickness in monolayer equivalent of the specific compound + film thickness in monolayer equivalent of the n-type organic semiconductor) x 100) is preferably 20 to 80% by volume, more preferably 40 to 80% by volume. When the photoelectric conversion film contains an n-type organic semiconductor and a p-type organic semiconductor, the content of the specific compound (film thickness in monolayer equivalent of the specific compound / (film thickness in monolayer equivalent of the specific compound + film thickness in monolayer equivalent of the n-type organic semiconductor + film thickness in monolayer equivalent of the p-type organic semiconductor) x 100) is preferably 15 to 75% by volume, more preferably 30 to 75% by volume. It is preferable that the photoelectric conversion film is substantially composed of the specific compound, the n-type organic semiconductor, and a p-type organic semiconductor that is included as desired. "Substantially" means that the total content of the specific compound, n-type organic semiconductor, and p-type organic semiconductor is 90 to 100% by volume, preferably 95 to 100% by volume, and more preferably 99 to 100% by volume, relative to the total mass of the photoelectric conversion film.

[0146] <p-Type Organic Semiconductor> The photoelectric conversion film preferably further contains a p-type organic semiconductor in addition to the specific compound. The p-type organic semiconductor is a compound different from the specific compound. The p-type organic semiconductor is a donor organic semiconductor material (compound) and refers to an organic compound that has the property of easily donating electrons. In other words, the p-type organic semiconductor refers to the organic compound that has a smaller ionization potential when two organic compounds are used in contact with each other. The p-type organic semiconductor may be used alone or in combination of two or more types.

[0147] Examples of p-type organic semiconductors include triarylamine compounds (e.g., N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), compounds described in paragraphs

[0128] to

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

[0052] to

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

[0119] to

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

[0044] to

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

[0086] to

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

[0031] to

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

[0043] to

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

[0025] to

[0037] and

[0099] to

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

[0029] to

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

[0015] to

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

[0053] , compounds described in paragraphs

[0045] to

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

[0063] to

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

[0033] to

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

[0044] to

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

[0041] to

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

[0034] to

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

[0033] to

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

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

[0019] to

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

[0031] to

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

[0036] to

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

[0055] to

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

[0041] to

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

[0044] to

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

[0041] to

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

[0042] to

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

[0043] to

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

[0031] to

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

[0036] to

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

[0045] to

[0048] of JP2020-010024A, etc.), cyanine compounds, oxonol compounds, polyamine compounds, indole compounds, pyrrole compounds, pyrazole compounds, polyarylene compounds, fused aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyarylalkane compounds, pyrazolone compounds, amino-substituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having a nitrogen-containing heterocyclic compound as a ligand. Examples of p-type organic semiconductors include benzoxazole compounds (for example, compounds described in Figures 3 to 7 of JP-A No. 2022-123944), dicarbazole compounds (for example, compounds described in Figures 2 to 5 of JP-A No. 2022-122839), benzoquinazoline compounds (for example, compounds described in paragraphs

[0053] to

[0056] of JP-A No. 2022-120323), and azine compounds (for example,compounds described in paragraphs

[0041] to

[0042] of JP-A No. 2022-120273), compounds described in Figures 2 to 10 of JP-A No. 2022-115832, indolotriphenylene compounds (for example, compounds described in paragraphs

[0065] to

[0072] of JP-A No. 2022-108268), indolocarbazole compounds (for example, compounds described in paragraphs

[0052] to

[0073] of JP-A No. 2023-005703, Examples of p-type organic semiconductors include compounds having a lower ionization potential than n-type organic semiconductors, and if this condition is met, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of compounds that can be used as p-type organic semiconductors include: triscarbazolylphenyl compounds (for example, compounds described in paragraphs

[0038] to

[0040] of JP-A No. 2022-181226); compounds described in paragraphs

[0070] to

[0082] of JP-A No. 2022-027575; and compounds described in paragraphs

[0051] to

[0064] of JP-A No. 2021-163968. Examples of p-type organic semiconductors include compounds having a lower ionization potential than n-type organic semiconductors, and if this condition is met, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of compounds that can be used as p-type organic semiconductors are listed below.

[0148]

[0149]

[0150]

[0151]

[0152] The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.

[0153] When the photoelectric conversion film contains a p-type organic semiconductor, the content of the p-type organic semiconductor in the photoelectric conversion film (thickness of the p-type organic semiconductor in terms of a single layer / thickness of the photoelectric conversion film × 100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 25 to 50 vol%.

[0154] The photoelectric conversion film containing the specific compound is a non-luminescent film and has characteristics different from those of an organic electroluminescent device (OLED: Organic Light Emitting Diode). A non-luminescent film means a film having a luminescence quantum efficiency of 1% or less, preferably 0.5% or less, more preferably 0.1% or less. The lower limit is often 0% or more.

[0155] <Dye> The photoelectric conversion film may further contain a dye in addition to the specific compound. The dye is a compound different from the specific compound. The dye is preferably an organic dye. Examples of the organic dye include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarylium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, acridine dyes, Examples of the organic dye include acridinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes and metal complex dyes, imidazoquinoxaline dyes described in WO 2020 / 013246, WO 2022 / 168856, JP 2023-10305 A, and JP 2023-10299 A, acceptor-donor-acceptor type dyes in which two acidic nuclei are bonded to a donor, and donor-acceptor-donor type dyes in which two donors are bonded to an acceptor. Among these, cyanine dyes, imidazoquinoxaline dyes, or acceptor-donor-acceptor type dyes are preferred as organic dyes, as they have a maximum absorption wavelength in the preferred range described below.

[0156] The maximum absorption wavelength of the dye is preferably in the visible light region, more preferably from 400 to 700 nm, and even more preferably from 400 to 650 nm.

[0157] The content of the dye in the photoelectric conversion film relative to the total content of the specific compound and the dye (=(film thickness of the dye in terms of a single layer / (film thickness of the specific compound in terms of a single layer+film thickness of the dye in terms of a single layer)×100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 20 to 50 vol%.

[0158] In addition to the components described above, the photoelectric conversion film may further contain optional components. Examples of optional components include antioxidants, dispersants, and ultraviolet absorbers. The optional components may also be impurities derived from specific compounds, n-type organic semiconductors, p-type organic semiconductors, or dyes. When the photoelectric conversion film contains optional components, the content of the optional components in the photoelectric conversion film (film thickness of the optional components in terms of a single layer / film thickness of the photoelectric conversion film × 100) is preferably 0.01 to 10% by volume, and more preferably 0.01 to 1% by volume.

[0159] <Film formation method> Examples of the film formation method for the photoelectric conversion film include a dry film formation method and a coating film formation method. Examples of dry film formation methods include physical vapor deposition methods such as vapor deposition (particularly vacuum deposition), sputtering, ion plating, and MBE (Molecular Beam Epitaxy), as well as CVD (Chemical Vapor Deposition) methods such as plasma polymerization, and vacuum deposition is preferred. When forming a photoelectric conversion film by vacuum deposition, manufacturing conditions such as the degree of vacuum and deposition temperature can be set according to conventional methods. Alternatively, a photoelectric conversion film may be formed by a dry film formation method using a specific compound obtained by recrystallization treatment using the composition of the present invention. Alternatively, a photoelectric conversion film may be formed by a coating film formation method in which the composition of the present invention is applied.

[0160] The thickness of the photoelectric conversion film is preferably from 10 to 1,000 nm, more preferably from 50 to 800 nm, and even more preferably from 50 to 500 nm.

[0161] [Electrodes] The photoelectric conversion element preferably has electrodes. The electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Examples of conductive materials include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident through the upper electrode 15, it is preferable that the upper electrode 15 is transparent to the light to be detected. Examples of materials constituting the upper electrode 15 include conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO: Antimony Tin Oxide, FTO: Fluorine-doped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO: Indium Tin Oxide), and indium zinc oxide (IZO); thin metal films such as gold, silver, copper, chromium, aluminum, and nickel; mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and nanocarbon materials such as carbon nanotubes and graphene. Of these, conductive metal oxides are preferred in terms of high conductivity and transparency.

[0162] Typically, when the conductive film is made thinner than a certain range, the resistance value often increases rapidly. In a solid-state imaging device incorporating a photoelectric conversion element according to this embodiment, the sheet resistance may be 100 to 10,000 Ω / □, and there is a wide degree of freedom in the range of film thickness that can be reduced. Furthermore, the thinner the film thickness of the upper electrode (transparent conductive film) 15, the less light it absorbs, and generally the higher the light transmittance. An increase in light transmittance is desirable because it increases light absorption in the photoelectric conversion film and enhances photoelectric conversion performance. Considering the suppression of leakage current, the increase in the resistance value of the thin film, and the increase in transmittance that accompany a reduction in film thickness, the thickness of the upper electrode 15 is preferably 5 to 100 nm, and more preferably 5 to 20 nm.

[0163] Depending on the application, the lower electrode 11 may be made transparent or may be made non-transparent and reflect light. Examples of materials constituting the lower electrode 11 include conductive metal oxides such as tin oxide (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO) doped with antimony or fluorine, etc.; metals such as gold, silver, copper, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and carbon materials such as carbon nanotubes and graphene.

[0164] The method for forming the electrodes can be appropriately selected depending on the electrode material. Specific examples include wet methods such as printing and coating; physical methods such as vacuum deposition, sputtering, and ion plating; and chemical methods such as CVD and plasma CVD. When the electrode material is ITO, examples include electron beam methods, sputtering, resistance heating deposition, chemical reaction methods (such as the sol-gel method), and coating of a dispersion of indium tin oxide.

[0165] [Charge-blocking film: electron-blocking film, hole-blocking film] The photoelectric conversion element preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film. Examples of the intermediate layer include a charge-blocking film. When the photoelectric conversion element has this film, the properties (quantum efficiency, response speed, etc.) of the resulting photoelectric conversion element are more excellent. Examples of the charge-blocking film include an electron-blocking film and a hole-blocking film.

[0166] [Electron Blocking Film] The electron blocking film is a donor organic semiconductor material (compound), and the above-mentioned p-type organic semiconductor can be used. Polymer materials can also be used as the electron blocking film. Examples of polymer materials include polymers of phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, diacetylene, and the like, and derivatives thereof.

[0167] The electron blocking film may be composed of multiple films. The electron blocking film may be composed of an inorganic material. In general, inorganic materials have a higher dielectric constant than organic materials, so when an inorganic material is used for the electron blocking film, a higher voltage is applied to the photoelectric conversion film, resulting in higher quantum efficiency. Examples of inorganic materials that can be used for the electron blocking film include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, indium copper oxide, indium silver oxide, and iridium oxide.

[0168] [Hole-Blocking Film] The hole-blocking film is an acceptor organic semiconductor material (compound), and the n-type organic semiconductors described above can be used. The hole-blocking film may be composed of multiple films.

[0169] Examples of methods for producing a charge blocking film include dry film formation and wet film formation. Examples of dry film formation include vapor deposition and sputtering. Vapor deposition may be either physical vapor deposition (PVD) or chemical vapor deposition (CVD), with physical vapor deposition such as vacuum deposition being preferred. Examples of wet film formation include inkjet printing, spray printing, nozzle printing, spin coating, dip coating, casting, die coating, roll coating, bar coating, and gravure coating, with the inkjet method being preferred in terms of high-precision patterning.

[0170] The thickness of each of the charge blocking films (electron blocking film and hole blocking film) is preferably from 3 to 200 nm, more preferably from 5 to 100 nm, and even more preferably from 5 to 30 nm.

[0171] [Substrate] The photoelectric conversion element may further include a substrate. Examples of the substrate include a semiconductor substrate, a glass substrate, and a plastic substrate. The substrate is usually positioned such that a conductive film, a photoelectric conversion film, and a transparent conductive film are stacked in this order on the substrate.

[0172] [Sealing Layer] The photoelectric conversion element may further have a sealing layer. The performance of photoelectric conversion materials may be significantly degraded in the presence of degrading factors such as water molecules. Therefore, the degradation can be prevented by covering and sealing the entire photoelectric conversion film with a sealing layer made of ceramics such as dense metal oxides, metal nitrides, or metal nitride oxides, or diamond-like carbon (DLC), which do not allow water molecules to penetrate. Examples of sealing layers include those described in paragraphs

[0210] to

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

[0173] [Method for manufacturing photoelectric conversion element] Examples of methods for manufacturing photoelectric conversion elements include known manufacturing methods. Specifically, for example, methods for manufacturing photoelectric conversion elements include a step of forming a conductive film on a substrate, a step of forming a photoelectric conversion film, and a step of forming a transparent conductive film. The method for manufacturing a photoelectric conversion element may include other steps (for example, a step of forming a charge blocking film and a step of forming a sealing layer) in addition to the above. The method for forming each layer is as described above.

[0174] [Imaging element] An example of an application of a photoelectric conversion element is an imaging element. An imaging element is an element that converts the optical information of an image into an electrical signal, and typically has multiple photoelectric conversion elements arranged in a matrix on the same plane, with each photoelectric conversion element (pixel) converting the optical signal into an electrical signal and outputting the electrical signal pixel by pixel from the imaging element. For this reason, each pixel is composed of one or more photoelectric conversion elements and one or more transistors. The manufacturing method of an imaging element is not particularly limited, but examples include a method including the step of manufacturing the photoelectric conversion element described above.

[0175] [Optical Sensor] Other applications of the photoelectric conversion element include, for example, a photocell and an optical sensor, and the photoelectric conversion element of the present invention is preferably used as an optical sensor. As an optical sensor, the photoelectric conversion element may be used alone, or may be used as a line sensor in which the photoelectric conversion elements are arranged linearly or as a two-dimensional sensor in which the photoelectric conversion elements are arranged on a plane.

[0176] The present invention will be described in more detail below with reference to the following examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the following examples.

[0177] [Compounds used in photoelectric conversion film] [Synthesis of compound (D-1)] Compound (D-1) was synthesized according to the following scheme.

[0178]

[0179] Compound (D-1-1) (2.0 mmol), compound (D-1-2) (5.0 mmol), toluene (60 mL), and piperidine (0.02 mmol) were placed in a glass reaction vessel and reacted at 100°C for 2 hours under a nitrogen atmosphere. After cooling to room temperature, methanol was added, and the precipitated solid was filtered. The obtained solid was dissolved in chloroform: 1,1,1,3,3,3-hexafluoroisopropanol (HFIP): toluene (4:1:1 volume ratio) to prepare a composition containing a specific compound (corresponding to the composition of the present invention). The obtained composition was recrystallized by distilling off chloroform and HFIP under reduced pressure. The precipitated crystals were collected by filtration, dried under reduced pressure, and purified by sublimation to obtain 0.90 mmol of compound (D-1) (yield 45%). The structure of compound (D-1) was confirmed by LDI-MS. LDI-MS (compound (D-1)): 594 (M ＋ )

[0180] Compounds (D-2) to (D-20) were synthesized with reference to the synthesis method for compound D-1 described above. In the synthesis of compounds (D-2) to (D-20), predetermined amounts of "alcohol" and "organic solvent other than alcohol" shown in Table 1 below were used instead of the chloroform:1,1,1,3,3,3-hexafluoroisopropanol (HFIP):toluene (4:1:1 volume ratio) used in the synthesis of compound (D-1). More specifically, in the synthesis of compounds (D-2) to (D-20), compositions containing each of compounds (D-2) to (D-20), the "alcohol" shown in Table 1, and the "organic solvent other than alcohol" shown in Table 1 were prepared. Similar to the synthesis of compound (D-1), the solvent in the composition was distilled off to perform recrystallization, and the precipitated crystals were collected by filtration, dried under reduced pressure, and then purified by sublimation to obtain each compound. In each of the Examples and Comparative Examples shown in Table 1 below, photoelectric conversion elements were produced using compounds (D-1) to (D-20) obtained by the above procedure, and their characteristics were evaluated. In each of the Examples and Comparative Examples, the content of the specific compound in a composition containing a specific compound such as compounds (D-1) to (D-20) produced above and various solvents ("alcohol" shown in Table 1 and "organic solvent other than alcohol" shown in Table 1) varied depending on the type of specific compound used. Specifically, the content of the specific compound relative to the total mass of the composition was as follows. For example, in an example using compound (D-1), the content of compound (D-1) relative to the total mass of the composition was 1 mass%. Compound (D-1): 1% by mass, Compound (D-2): 2% by mass, Compound (D-3): 5% by mass, Compound (D-4): 2% by mass, Compound (D-5): 1% by mass, Compound ( D-6): 2% by mass, Compound (D-7): 0.5% by mass, Compound (D-8): 5% by mass, Compound (D-9): 15% by mass, Compound (D-10): 3% by mass, Compound ( D-11): 20% by mass, Compound (D-12): 20% by mass, Compound (D-13): 5% by mass, Compound (D-14): 1% by mass, Compound (D-15): 1% by mass, Compound (D-16): 3% by mass, Compound (D-17): 5% by mass, Compound (D-18): 5% by mass, Compound (D-19): 10% by mass, Compound (D-20): 1% by mass.

[0181]

[0182] [Evaluation] The quantum efficiency, response speed, and electric field strength dependency of the response speed when the photoelectric conversion element received light were evaluated by the following methods.

[0183] <Preparation of Photoelectric Conversion Element> A photoelectric conversion element having the configuration shown in FIG. 2 was prepared using the various components shown above. Here, the photoelectric conversion element comprises a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15. Specifically, amorphous ITO was formed on a glass substrate by sputtering to form a lower electrode 11 (thickness: 30 nm), and compound (EB-1) was further formed on the lower electrode 11 by vacuum heating deposition to form an electron blocking film 16A (thickness: 30 nm). Subsequently, with the temperature of the glass substrate controlled at 25°C, a specific compound shown in Table 1 and an n-type organic semiconductor (fullerene (C ６０ )) and a p-type organic semiconductor (compound (P-1)) were co-deposited by vacuum deposition to form a film having a thickness of 80 nm in terms of a single layer. This formed a photoelectric conversion film 12 having a bulk heterostructure of 240 nm. At this time, the film formation rate of the photoelectric conversion film 12 was 1.0 Å / sec. Furthermore, compound (EB-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). Amorphous ITO was deposited on the hole blocking film 16B by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm). After a SiO film was formed as a sealing layer on the upper electrode 15 by vacuum deposition, aluminum oxide (Al ２ O ３ The resulting laminate was heated in a glove box at 150° C. for 30 minutes to obtain a photoelectric conversion element.

[0184]

[0185] <Dark Current> The dark current of each of the obtained photoelectric conversion elements was measured by the following method. ５ A voltage was applied to the photoelectric conversion element so as to obtain an electric field strength of 50 nA / cm. The current value in a dark place (dark current) was measured. As a result, the dark current was 50 nA / cm for all the photoelectric conversion elements. ２ It was confirmed that the dark current was sufficiently low.

[0186] <Quantum Efficiency> The quantum efficiency of each of the obtained photoelectric conversion elements was measured by the following method. ５ After applying a voltage to achieve an electric field strength of 100 V / cm, light was irradiated from the upper electrode (transparent conductive film) side to evaluate the quantum efficiency (photoelectric conversion efficiency) at a wavelength of 500 nm, and the value obtained according to formula (Z1) was evaluated in accordance with the following criteria. The quantum efficiency is preferably rated B or higher. Formula (Z1): Quantum efficiency (relative ratio) = (quantum efficiency at a wavelength of 500 nm of each Example or Comparative Example) / (quantum efficiency at a wavelength of 500 nm of Comparative Example 1-1)

[0187] (Evaluation criteria) "A": Quantum efficiency (relative ratio) is greater than 1.1 "B": Quantum efficiency (relative ratio) is greater than 1.0 and less than or equal to 1.1 "C": Quantum efficiency (relative ratio) is greater than 0.9 and less than or equal to 1.0 "D": Quantum efficiency (relative ratio) is less than or equal to 0.9

[0188] <Response Speed> The response speed of each of the obtained photoelectric conversion elements was evaluated by the following method. ５ A voltage was applied to the sample so that the intensity was 100 V / cm. Thereafter, an LED (light emitting diode) was momentarily turned on to irradiate light from the upper electrode (transparent conductive film) side, and the photocurrent at a wavelength of 500 nm at that time was measured with an oscilloscope to measure the rise time from 0% signal intensity to 97% signal intensity. The value obtained according to formula (Z2) was used to evaluate the response speed in accordance with the following criteria. A response speed rating of B or higher is preferred. Formula (Z2): Relative response speed = (rise time at a wavelength of 500 nm for each Example or Comparative Example) / (rise time at a wavelength of 500 nm for Comparative Example 1-1)

[0189] (Evaluation Criteria) "A": Relative response speed is less than 0.95 "B": Relative response speed is 0.95 or more and less than 1.00 "C": Relative response speed is 1.00 or more and less than 1.50 "D": Relative response speed is 1.50 or more

[0190] <Dependence of response speed on electric field strength> The dependence of response speed on electric field strength of each of the obtained photoelectric conversion elements was evaluated by the following method. In the evaluation of the above <Response speed>, a voltage of 7.5×10 ４ The same procedure was followed except that the pressure was changed to 7.5 × 10 ４ The response speed at 7.5 × 10 V / cm was measured, and the electric field strength dependency of the response speed obtained according to formula (Z3) was evaluated according to the following criteria in light of the criteria of formula (Z4). In formula (Z3), the numerator and denominator are values ​​measured for the photoelectric conversion element of the same Example or Comparative Example. The relative value of the electric field strength dependency of the response speed is preferably rated B or higher. Formula (Z3): Electric field strength dependency of response speed = (7.5 × 10 V at a wavelength of 500 nm for each Example or Comparative Example) ４ V / cm) / (1.0×10 at a wavelength of 500 nm for each Example or Comparative Example) ５ Rise time at 1000 V / cm) Formula (Z4): Relative value of electric field strength dependency of response speed = (electric field strength dependency of response speed of each Example or Comparative Example) / (electric field strength dependency of response speed of Examples 1 to 21)

[0191] (Evaluation Criteria) "A": The relative value of the electric field strength dependency of the response speed is less than 0.9. "B": The relative value of the electric field strength dependency of the response speed is 0.9 or more and 1.0 or less. "C": The relative value of the electric field strength dependency of the response speed is more than 1.0 and less than 1.1. "D": The relative value of the electric field strength dependency of the response speed is 1.1 or more.

[0192] [Results] The evaluation results are shown in Table 1 below. The numbers in parentheses next to the specific examples of various components indicate the volume ratio of each solvent. Each "Formula" column indicates the formula to which each compound corresponds. The "Alcohol / (Alcohol + Organic Solvent)" column indicates the alcohol content (volume %) relative to the total content of alcohol and organic solvent. The "H, C, X only" column indicates "A" when the organic solvent other than the specific alcohol is composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, and halogen atoms, and "B" otherwise. The pKa of the alcohol is a value obtained by the method described above.

[0193]

[0194] HFIP: 1,1,1,3,3,3-hexafluoroisopropanol

[0195] The results shown in Table 1 confirm that the composition of the present invention can produce a compound capable of producing a photoelectric conversion element having a small electric field strength dependence of response speed. It was confirmed that when the alcohol content relative to the total content of the alcohol and organic solvent is 10% by volume or more, the electric field strength dependence of response speed is better (e.g., comparison between Examples 1-1 to 1-7, 1-9, 1-14 to 1-17, and 1-20 and Examples 1-8 and 1-21). It was confirmed that when the acid dissociation constant pKa of the specific alcohol is 10.0 or less, or when the specific alcohol is an alcohol represented by formula (S1), the quantum efficiency, response speed, and electric field strength dependence of the response speed are all better (e.g., comparison between Examples 1-1 to 1-7, 1-9, 1-14 to 1-17, and 1-20 and Examples 1-11 and 1-12). It was confirmed that when an organic solvent other than the specific alcohol is included and the organic solvent is composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, and halogen atoms, the electric field intensity dependence of the response speed is superior (e.g., comparison of Examples 1-1 to 1-7, 1-9, 1-14 to 1-17, and 1-20 with Example 1-10). １ and A ２It was confirmed that when the group represented by formula (A-1) is a group represented by formula (A-1), all of the quantum efficiency, response speed, and electric field strength dependence of the response speed are superior (e.g., comparison between Examples 1-1 to 1-7, 1-9, 1-14 to 1-17, and 1-20 and Example 1-13). Furthermore, when the group represented by formula (A-1) is a group represented by formula (C-1) or a group represented by formula (C-2), all of the response speed and electric field strength dependence of the response speed are superior (e.g., comparison between Examples 1-1 to 1-7, 1-9, 1-14 to 1-17, and 1-20 and Example 1-18). It was confirmed that when the specific compound is a compound represented by formula (1), at least one of the effects of the quantum efficiency, response speed, and electric field strength dependence of the response speed is superior (e.g., comparison between Examples 1-1 to 1-7, 1-9, 1-14 to 1-17, and 1-20 and Examples 1-11, 1-12, 1-19, and 1-21).

[0196] 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 composition comprising a compound selected from the group consisting of compounds represented by formula (1) and compounds represented by formula (2), and an alcohol having an acid dissociation constant pKa of 13.0 or less. In formula (1), D １ represents a conjugated structure having at least one ring structure. n1 represents 2 or 3. m1 represents 0 or 1. A １ represents a group represented by formula (A-1) or a group represented by formula (A-2). ２ represents a structure having at least one ring structure. n2 represents an integer of 1 to 3. m2 represents 0 or 1. A ２ represents a group represented by formula (A-1) or a group represented by formula (A-2). In formula (A-1), * represents a bonding position. １ is one or more carbon atoms and X Ｙ and represents a ring which may have a substituent. Ｙ is >C=Y １ Or > N-Y ２ Represents Y. １ represents an oxygen atom, a sulfur atom, and ═NR Ｙ１ , or =CR Ｙ２ R Ｙ３ Represents Y. ２ represents a hydrogen atom or a substituent. Ｙ１ represents a hydrogen atom or a substituent. １ Ga = NR Ｙ１ represents C １ represents a ring containing two or more carbon atoms and having a substituent, R Ｙ１ And, C １ and the substituents on the ring represented by R may be bonded to each other to form a ring. Ｙ２ and R Ｙ３ each independently represents a cyano group, —SO ２ R Ｙ４ , -COOR Ｙ５ , or -COR Ｙ６ Represents R Ｙ４ ~R Ｙ６ R each independently represent an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. In formula (A-2), * represents a bonding position. Ａ１ and R Ａ２ each independently represents a cyano group, —SO ２ R Ｘ１ , -COOR Ｘ２ , or -COR Ｘ３ Represents R Ｘ１ ~R Ｘ３ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent.

2. The composition according to claim 1, wherein the alcohol is an alcohol represented by formula (S1). In formula (S1), R Ｓ１ ~R Ｓ６ each independently represents a hydrogen atom or a substituent, R Ｓ１ ~R Ｓ６ At least one of R represents a fluorine atom. Ｓ７ represents a hydrogen atom or a substituent.

3. The composition according to claim 1 or 2, wherein the alcohol has an acid dissociation constant pKa of 10.0 or less.

4. A composition according to claim 1 or 2, wherein n1 represents 2 and n2 represents 1 or 2.

5. The composition according to claim 1 or 2, wherein the compound represented by formula (1) is a compound represented by formula (1-1), and the compound represented by formula (2) is a compound represented by formula (2-1). In formula (1-1), ring A and ring B each independently represent a monocyclic ring having a conjugated structure, a fused ring having a conjugated structure, or two of the monocyclic rings linked by a chain-like conjugated linking group. １ each independently represents a group represented by formula (A-1) or a group represented by formula (A-2). Each m1 independently represents 0 or 1. o1 represents an integer of 0 to 2. In formula (2-1), ring C represents a monocyclic ring having a conjugated structure or a fused ring having a conjugated structure. A ２ represents a group represented by the formula (A-1) or a group represented by the formula (A-2). m2 represents 0 or 1. X １ and X ２ One of them is -NR Ｎ -, and the other represents a sulfur atom, an oxygen atom, a selenium atom, or -NR Ｎ -or-CR ｃ１ ２ - represents. Ｎ represents a hydrogen atom or a substituent. ｃ１ represents a hydrogen atom or a substituent.

6. The monocycle having a conjugated structure is an aromatic six-membered ring having an atom selected from the group consisting of carbon and nitrogen atoms as a ring member, or an oxygen atom, sulfur atom, selenium atom, -NR Ｄ１ -, -SiR Ｄ２ ２ -, -GeR Ｄ３ ２ -, -CR Ｄ４ ２ - and >C=CR Ｄ５ ２ is a conjugated five-membered ring in which an atom or structure selected from the group consisting of Ｄ１ ~R Ｄ５ each independently represents a hydrogen atom or a substituent, or -Y Ｄ１ -Y Ｄ２ - is a non-aromatic conjugated six-membered ring constituting a ring, and Y Ｄ１ and Y Ｄ２ one of which is an oxygen atom, a sulfur atom, a selenium atom, or -NR Ｄ６ -, and the other is -CR ｃ２ ２ represents -, and R Ｄ６ represents a hydrogen atom or a substituent, R ｃ２ represents a hydrogen atom or a substituent, and the fused ring having a conjugated structure is formed by condensing a plurality of rings selected from the group consisting of the aromatic six-membered ring, the conjugated five-membered ring, and the non-aromatic conjugated six-membered ring.

7. A １ and A ２ are each independently a group represented by formula (A-1).

8. A １ and A ２ is a group represented by formula (A-1), and the group represented by formula (A-1) is a group represented by formula (C-1) or a group represented by formula (C-2). In formula (C-1), * represents a bonding position. ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｃ１ or =CR Ｃ２ R Ｃ３ Represents R Ｃ１ represents a hydrogen atom or a substituent. Ｃ２ and R Ｃ３ each independently represents a cyano group, —SO ２ R Ｃ４ , -COOR Ｃ５ or -COR Ｃ６ Represents R Ｃ４ ~R Ｃ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ３ represents an aromatic ring containing two or more carbon atoms and which may have a substituent. In formula (C-2), * represents a bonding position. X ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR Ｃ１ or =CR Ｃ２ R Ｃ３ Represents R Ｃ１ represents a hydrogen atom or a substituent. Ｃ２ and R Ｃ３ each independently represents a cyano group, —SO ２ R Ｃ４ , -COOR Ｃ５ , or -COR Ｃ６ Represents R Ｃ４ ~R Ｃ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. ｃ１ and Z ｃ２ are each independently -NR Ｃ７ -or-CR Ｃ８ ２ - represents. Ｃ７ and R Ｃ８ each independently represents a hydrogen atom or a substituent.

9. The composition according to claim 2, comprising the compound represented by formula (1) and the alcohol represented by formula (S1).

10. The composition according to claim 1 or 2, further comprising an organic solvent other than the alcohol.

11. The composition of claim 10, wherein the organic solvent is composed solely of atoms selected from the group consisting of hydrogen atoms, carbon atoms, and halogen atoms.

12. The composition according to claim 10, wherein the content of the alcohol is 10% by volume or more relative to the total content of the alcohol and the organic solvent.

13. The composition according to claim 1 or 2, wherein the alcohol is an alcohol represented by formula (S2). In formula (S2), R Ｓ１ ~R Ｓ３ each independently represents a hydrogen atom or a substituent, R Ｓ１ ~R Ｓ３ At least one of R represents a fluorine atom. Ｓ７ represents a hydrogen atom or a substituent.

14. The composition according to claim 1 or 2, wherein the alcohol is an alcohol represented by formula (S3). In formula (S3), R Ｓ７ represents a hydrogen atom or a substituent.

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