Photoelectric conversion element, imaging element, photosensor, and compound

Abstract

A first problem to be addressed by the present invention is to provide a photoelectric conversion element that has excellent quantum efficiency when receiving blue light. A second problem to be addressed by the present invention is to provide an imaging element, a photosensor, and a compound that pertain to the photoelectric conversion element.　A photoelectric conversion element of the present invention comprises an electroconductive film, a photoelectric conversion film, and a transparent electroconductive film in this order, the photoelectric conversion film comprising a compound represented by formula (1).

Description

Photoelectric conversion elements, imaging elements, optical sensors, compounds

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

[0002] In recent years, development of devices having a photoelectric conversion film (for example, an image sensor) has progressed. For example, Patent Document 1 discloses the following compound.

[0003] Furthermore, for example, Non-Patent Document 1 discloses the following compound.

[0004]

[0005] Chinese Patent Application Publication No. 110790743

[0006] Energy & Environmental Science (2018), 11(9), 2569-2580

[0007] In recent years, with the demand for improved performance of image sensors, optical sensors, and the like, further improvements in the properties required of the photoelectric conversion elements used therein have been demanded. For example, there is an even greater demand for photoelectric conversion elements to have high quantum efficiency when receiving blue light (particularly, a wavelength of 460 nm). Here, the blue light refers to light with a wavelength in the range of 400 to 500 nm. The present inventors have studied photoelectric conversion elements containing the compounds disclosed in Patent Document 1 and found that there is room for further improvement in quantum efficiency when receiving blue light.

[0008] Therefore, an object of the present invention is to provide a photoelectric conversion element that has excellent quantum efficiency when receiving blue light. Another object of the present invention is to provide an imaging element, a photosensor, and a compound related to the photoelectric conversion element.

[0009] As a result of extensive research into solving the above problems, the present inventors have found that the above problems can be solved by the following configuration.

[0010] [1] A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains a compound represented by formula (1) described later. [2] The R Ｚ１ and the above R Ｚ４ [3] The photoelectric conversion element according to [1], wherein the substituent represented by the formula: ３ is represented by the formula (Ar ３ -1) to formula (Ar ３ [4] The photoelectric conversion element according to [1] or [2], wherein R Ｚ５ , the above R Ｚ９ , the above R Ｚ１１ , the above R Ｚ１２ , the above R Ｚ１６ , and the above R Ｘ [5] The photoelectric conversion element according to [3], wherein the substituent represented by the formula: ３ is expressed by the above formula (Ar ３ -1) or the above formula (Ar ３ The photoelectric conversion element according to [3] or [4], wherein the group represented by the formula (Ar -2) is ３ In the group represented by formula (1), Z ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ３ In the group represented by formula (2), Z ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ do not combine with each other to form a ring. [6] The above A １ and the above A ２represents a group represented by the formula (A-1). [7] The photoelectric conversion element according to any one of [1] to [6], wherein the group represented by the formula (A-1) represents a group represented by the formula (C-1) or (C-2) described below. [8] The photoelectric conversion element according to any one of [1] to [6], wherein the group represented by the formula (A-1) represents a group represented by the formula (C-1) or (C-2) described below. １ But, -NR Ｎ -, -CR Ｃ１ R Ｃ２ - or -SiR Ｃ１ R Ｃ２ -. [9] The photoelectric conversion element according to any one of [1] to [7], wherein the photoelectric conversion film further contains an n-type organic semiconductor, and the photoelectric conversion film has a bulk heterostructure formed by mixing the compound represented by formula (1) with the n-type organic semiconductor.

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

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

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

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

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

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

[12] .

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

[12] .

[15] A compound represented by formula (1) described below.

[16] The above R Ｚ１ and the above R Ｚ４

[17] The compound according to

[15] , wherein the substituent represented by the formula: represents the substituent T described below. ３ is represented by the formula (Ar ３ -1) to formula (Ar ３

[18] The compound according to

[15] or

[16] , wherein R Ｚ５ , the above R Ｚ９ , the above R Ｚ１１ , the above R Ｚ１２ , the above R Ｚ１６ , and the above R Ｘ

[19] The compound according to

[17] , wherein the substituent represented by the formula: represents the substituent T described below. ３ is expressed by the above formula (Ar ３-1) or the above formula (Ar ３ The compound according to

[17] or

[18] , wherein the compound is a group represented by the formula (Ar -2). ３ In the group represented by formula (1), Z ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ３ In the group represented by formula (2), Z ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ do not combine with each other to form a ring.

[20] The above A １ and the above A ２ represents a group represented by the above formula (A-1).

[21] The compound according to any one of

[15] to

[20] , wherein the group represented by the above formula (A-1) represents a group represented by the below-mentioned formula (C-1) or formula (C-2).

[22] The compound according to any one of

[15] to

[20] , wherein the above X １ But, -CR Ｃ１ R Ｃ２ -or-SiR Ｃ１ R Ｃ２ The compound according to any one of

[15] to

[21] , wherein - represents.

[0011] According to the present invention, a photoelectric conversion element having excellent quantum efficiency when receiving blue light can be provided. Furthermore, according to the present invention, an imaging element, a photosensor, and a compound related to the photoelectric conversion element can be provided.

[0012] 1 is a schematic cross-sectional view showing an example of the configuration of a photoelectric conversion element.

[0013] 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.

[0014] Hereinafter, embodiments of the photoelectric conversion element of the present invention will be described in detail. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​written before and after "to" as the lower and upper limits. In this specification, a hydrogen atom may be a protist atom (a normal hydrogen atom) or a deuterium atom (e.g., a deuterium atom). In this specification, when there are multiple substituents and linking groups, etc. (hereinafter also referred to as "substituents, etc.") represented by a specific symbol, or when multiple substituents, etc. are specified simultaneously, this 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 groups exemplified by the substituent W described below.

[0015] (Substituent W) The substituent W in this specification will be described. Examples of the substituent W include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, an aryl group, a heteroaryl group (a heterocyclic group), a cyano group, a nitro group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, a secondary or Examples of the substituent W include a tertiary amino group (including anilino), 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 silyl 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, a boronic acid group, and a primary amino group. Furthermore, each of the above groups may further have a substituent (e.g., one or more of the above groups, etc.) if possible. For example, an alkyl group which may have a substituent is also included as one form of the substituent W. Furthermore, when the substituent W has a carbon atom, the number of carbon atoms contained in the substituent W is, for example, 1 to 20. The number of atoms other than hydrogen atoms contained in the substituent W is, for example, 1 to 30. The specific compounds described below may have, as 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 preferably has no primary amino group.

[0016] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0017] 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 i-propyl group, an n-butyl group, a t-butyl group, an n-hexyl group, and a cyclopentyl group. The alkyl group may be a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have a cyclic structure thereof as a partial structure. 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, and preferred are an aryl group (preferably having 6 to 18 carbon atoms, more preferably having 6 carbon atoms), a heteroaryl group (preferably having 5 to 18 carbon atoms, more preferably having 5 to 6 carbon atoms), or a halogen atom (preferably a fluorine atom or a chlorine atom).

[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 multiple (e.g., 2 to 6) condensed aromatic ring structures as a ring structure. The number of ring member atoms of the aromatic ring is preferably 5 to 15. The aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocycle. When the aromatic ring is an aromatic heterocycle, 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, and a phenanthrene ring.Examples of the aromatic heterocycle include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring (for example, a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring), a tetrazine ring (for example, 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, a benzopyrrole 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 3H-pyrrolidine ring, a pyrroloimidazole ring (for example, a 5H-pyrrolo[1,2-a]imidazole ring), an imidazooxazole ring (for example, an imidazo[2,1-b]oxazole), ring, etc.), thienothiazole ring (for example, thieno[2,3-d]thiazole ring, etc.), benzothiadiazole ring, benzodithiophene ring (for example, benzo[1,2-b:4,5-b']dithiophene ring, etc.), thienothiophene ring (for example, thieno[3,2-b]thiophene ring, etc.), thiazolothiazole ring (for example, thiazolo[5,4-d]thiazole ring, etc.), naphthodithiophene ring (for example, naphtho[2, Examples of the aromatic ring that may have a substituent include a benzothienobenzothiophene ring, a dithieno[3,2-b:2',3'-d]thiophene ring, and a 3,4,7,8-tetrathiadicyclopenta[a,e]pentalene ring. In the aromatic ring that may have a substituent, examples of the substituent that the aromatic ring may have include the groups exemplified by the substituent W. When the aromatic ring has a substituent, the number of the substituents may be one or more (e.g., 1 to 4, etc.). In this specification, the term "aromatic ring group" includes, for example, a group obtained by removing one or more hydrogen atoms (e.g., 1 to 5, etc.) from the aromatic ring. In this specification, the term "aryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring that corresponds to an aromatic hydrocarbon ring among the above aromatic rings.As used herein, the term "heteroaryl group" refers to, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above aromatic rings. As used herein, the term "arylene group" refers to, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings. As used herein, the term "heteroarylene group" refers to, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above aromatic rings. In the optionally substituted aromatic ring group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted arylene group, and optionally substituted heteroarylene group, the types of substituents that these groups may have include, for example, the groups exemplified for the substituent W. When these optionally substituted groups have substituents, the number of substituents may be 1 or more (e.g., 1 to 4).

[0021] Furthermore, in this specification, unless otherwise specified, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Furthermore, the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, even more preferably 1 to 6, particularly preferably 1 to 5, and most preferably 1 to 3, unless otherwise specified. The aliphatic hydrocarbon group is preferably an alkyl group, an alkenyl group, or an alkynyl group. Unless otherwise specified, the alkyl group, alkenyl group, and alkynyl group are preferably the same as those described above. In the aliphatic hydrocarbon group even if it has a substituent, examples of the substituent that the aliphatic hydrocarbon group may have include the groups exemplified for the substituent W.

[0022] In this specification, when a formula showing a chemical structure contains a plurality of identical symbols indicating the type or number of groups, the contents of the plurality of identical symbols are independent of each other, and the contents of the plurality of identical symbols may be the same or different, unless otherwise specified. In this specification, when a formula showing a chemical structure contains a plurality of groups of the same type (e.g., alkyl groups, etc.), the specific contents of the plurality of groups of the same type are independent of each other, and the specific contents of the plurality of groups of the same type may be the same or different, unless otherwise specified.

[0023] Unless otherwise specified, the bonding direction of a divalent group (e.g., -CO-O-) represented in this specification is not limited. For example, when Y is -CO-O- in a compound represented by the formula "X-Y-Z," the compound may be either "X-O-CO-Z" or "X-CO-O-Z."

[0024] 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.

[0025] [Photoelectric Conversion Element] The photoelectric conversion element of the present invention is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film contains a compound represented by formula (1) (hereinafter also referred to as "specific compound"). The mechanism by which the above-described configuration of the photoelectric conversion element of the present invention can solve the problems of the present invention is not necessarily clear, but the inventors speculate as follows. The specific compound is a compound having a donor moiety (D) and an acceptor moiety (A) (a so-called A-D-A compound), and the donor moiety is a three-fused ring-Ar having a predetermined structure *. ３ The three-fused ring structure has an asymmetric structure represented by -*. １ and Ar ２ and X １and a 5- or 6-membered ring containing X １ The ring containing X １ Ga-OCR Ｃ１ R Ｃ２ (When π-π represents -, it becomes a 6-membered ring.) It is presumed that the specific compound is less likely to aggregate due to π-π stacking due to the above structure. In other words, aggregation of specific compounds is suppressed in a photoelectric conversion film containing the specific compound, and as a result, charge separation in the photoelectric conversion film proceeds efficiently without being hindered, and the photoelectric conversion element exhibits excellent quantum efficiency.

[0026] Hereinafter, the achievement of at least one of the effects of better quantum efficiency when blue light is received, better responsiveness when blue light is received, and lower dependency of the response speed when blue light is received on electric field strength is also referred to as "the effect of the present invention being better."

[0027] FIG. 1 shows a cross-sectional schematic diagram of one embodiment of the photoelectric conversion element of the present invention. The photoelectric conversion element 10a shown in FIG. 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 functioning as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and a transparent conductive film (hereinafter also referred to as the "upper electrode") 15 functioning as an upper electrode are stacked in this order. FIG. 2 shows an example of the configuration of another photoelectric conversion element. The photoelectric conversion element 10b shown in FIG. 2 has a configuration in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are stacked in this order on a lower electrode 11. Note that the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in FIGS. 1 and 2 may be changed as appropriate depending on the application and characteristics.

[0028] 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 ７In 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.

[0029] [Photoelectric Conversion Film] The photoelectric conversion element has a photoelectric conversion film.

[0030] <Specific Compound> The photoelectric conversion film contains a compound (specific compound) represented by formula (1).

[0031]

[0032] In formula (1), R １ and R ２ R each independently represents a hydrogen atom or a substituent. １ and R ２ Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W. Among them, in terms of the effects of the present invention being more excellent, R １ and R ２ preferably represents a hydrogen atom.

[0033] In formula (1), X １ is -NR Ｎ -, -CR Ｃ１ R Ｃ２ -, -SiR Ｃ１ R Ｃ２ -, -GeR Ｃ１ R Ｃ２ --OCR Ｃ１ R Ｃ２ represents a sulfur atom, an oxygen atom, or a selenium atom. １As for the group, -NR is particularly preferred in that it provides a more excellent effect of the present invention. Ｎ -, -CR Ｃ１ R Ｃ２ -, -SiR Ｃ１ R Ｃ２ -, -GeR Ｃ１ R Ｃ２ - or - OCR Ｃ１ R Ｃ２ It is preferred that it represents -, and -NR Ｎ -, -CR Ｃ１ R Ｃ２ - or -SiR Ｃ１ R Ｃ２ More preferably, it represents -, and -CR Ｃ１ R Ｃ２ -or-SiR Ｃ１ R Ｃ２ It is more preferred that it represents -.

[0034] R Ｎ , R Ｃ１ , and R Ｃ２ R each independently represents a substituent S. The substituent S will be described in detail later. Ｃ１ and R Ｃ２ may be linked to each other to form a ring. Ｃ１ and R Ｃ２ The ring formed by combining R may be either an aromatic ring or an alicyclic ring, and may be either a monocyclic ring or a polycyclic ring. Ｃ１ and R Ｃ２ The ring formed by linking R to R is preferably an aliphatic hydrocarbon ring (for example, an aliphatic hydrocarbon ring having 3 to 8 carbon atoms). Ｃ１ and R Ｃ２ The aliphatic hydrocarbon ring formed by linking together may further be condensed with aromatic rings (preferably 1 to 2 rings). When the ring has a substituent, the substituent is preferably the substituent S described below, in that the effects of the present invention are more excellent.

[0035] In formula (1), Ar １ and Ar ２ each independently represents a group represented by formula (Ar-1) or formula (Ar-2). １ and Ar ２At least one of the groups represented by formula (Ar-1) is a group represented by formula (Ar-1).

[0036] In formula (Ar-1), Z １ ~Z ３ are each independently -CR Ｚ１ = or -N=. Z １ ~Z ３ Among them, -CR Ｚ１ Preferably, R represents Ｚ１ represents a hydrogen atom or a substituent. Ｚ１ Examples of the substituent represented by R include the groups exemplified as the substituent W above, and among these, the substituent T described below is preferred. Ｚ１ As for the substituent T, a hydrogen atom or the substituent T is preferred, and a hydrogen atom is more preferred, in terms of excellent effects of the present invention.

[0037] In formula (Ar-1), * １ is X in formula (1) １ represents the bonding position to a 5- or 6-membered ring containing * ２ is -C(R １ ) = A １ (the group represented by —C(R １ ) = A １ or Ar ３ That is, for example, Ar in formula (1) １ represents a group represented by formula (Ar-1), the group represented by formula (1) corresponds to a group represented by the following formula (1A) or the following formula (1B), and Ar in formula (1) ２ represents a group represented by formula (Ar-1), the group represented by formula (1) corresponds to a group represented by the following formula (1C) or (1D).

[0038]

[0039] In formula (Ar-2), X ２ represents a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ - represents X ２ Among these, a sulfur atom or an oxygen atom is preferable as R, and a sulfur atom is more preferable. ＮＸ represents a substituent S described below.４ is -CR Ｚ４ = or -N=. Z ４ Among them, -CR Ｚ４ Preferably, R represents Ｚ４ represents a hydrogen atom or a substituent. Ｚ４ Examples of the substituent represented by R include the groups exemplified as the substituent W above, and among these, the substituent T described below is preferred. Ｚ４ As for the substituent T, a hydrogen atom or the substituent T is preferred, and a hydrogen atom is more preferred, in terms of excellent effects of the present invention.

[0040] In formula (Ar-2), * ３ is X in formula (1) １ represents the bonding position to a 5- or 6-membered ring containing the following: ４ is -C(R １ ) = A １ (the group represented by —C(R １ ) = A １ or Ar ３ That is, for example, Ar in formula (1) １ represents a group represented by formula (Ar-2), the group represented by formula (1) corresponds to a group represented by the following formula (1E) or (1F), and Ar in formula (1) ２ represents a group represented by formula (Ar-2), the group represented by formula (1) corresponds to a group represented by the following formula (1G) or (1H).

[0041]

[0042] In formula (1), Ar ３ represents an optionally substituted monocyclic or bicyclic arylene group, or an optionally substituted monocyclic or bicyclic heteroarylene group. ３ In terms of achieving better effects of the present invention, it is preferable that the group represents a monocyclic arylene group which may have a substituent, or a monocyclic heteroarylene group which may have a substituent.

[0043] Ar ３Examples of the substituent that the monocyclic or bicyclic arylene group or monocyclic or bicyclic heteroarylene group represented by the following formula (I) may have include the groups exemplified as the substituent W above, and among these, the substituent T described below is preferred.

[0044] Ar ３ As the compound represented by the following formula (Ar ３ -1) to the following formula (Ar ３ It is preferable that the group represented by the formula (I) is -5).

[0045]

[0046] Formula (Ar ３ -1) Medium, Z ５ ~Z ８ are each independently -CR Ｚ５ = or -N=. Z ５ ~Z ８ As for -CR Ｚ５ Preferably, R represents Ｚ５ represents a hydrogen atom or a substituent. Ｚ５ Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W above, and among these, the substituent T described below is preferred. ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ may be linked to each other to form a monocyclic ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ may be linked to each other to form a monocyclic ring. ５ ~Z ８ Both are -CR Ｚ５ When representing =, Z ５ and Z ６ The two R's in Ｚ５ And Z ７ and Z ８ The two R's in Ｚ５ Only one of the two R may be linked to each other to form a monocycle. Ｚ５Examples of the monocyclic ring formed by linking together include a monocyclic aromatic ring and a monocyclic alicyclic ring which may contain a heteroatom, and in terms of the effects of the present invention being more excellent, a monocyclic alicyclic ring which may contain a heteroatom (preferably a cycloalkyl group) is preferred. ５ and Z ６ Both are -CR Ｚ５ In the case where the two R Ｚ５ Preferably, Z do not combine with each other to form a ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ are preferably not linked to each other to form a ring. * represents the bonding position.

[0047] Formula (Ar ３ -2) Medium, X ３ represents a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S described below. ９ and Z １０ are each independently -CR Ｚ９ = or -N=. Z ９ and Z １０ As for -CR Ｚ９ Preferably, R represents Ｚ９ represents a hydrogen atom or a substituent. Ｚ９ Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W above, and among these, the substituent T described below is preferred. ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ may be linked to each other to form a monocyclic ring. Ｚ９ Examples of the monocyclic ring formed by linking together include a monocyclic aromatic ring and a monocyclic alicyclic ring which may contain a heteroatom, and in terms of the effects of the present invention being more excellent, a monocyclic alicyclic ring which may contain a heteroatom (preferably a cycloalkyl group) is preferred. ９ and Z １０ Both are -CR Ｚ９In the case where Z = ９ and Z １０ The two R's in Ｚ９ are preferably not linked to each other to form a monocyclic structure. * indicates the bonding position.

[0048] Formula (Ar ３ -3) Medium, X ４ represents a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. １１ is -CR Ｚ１１ = or -N=, -CR Ｚ１１ Preferably, R represents Ｚ１１ represents a hydrogen atom or a substituent. Ｚ１１ Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W above, and among these, the substituent T described below is preferred.

[0049] X ５Ａ and X ５Ｂ one of which is a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ -, and the other represents -CR Ｘ = or -N=. ３ -3) In the above, X ５Ａ The dotted line between the carbon atom and the adjacent carbon atom represents X ５Ａ is a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ When "-" is used, it represents a single line (single bond), and X ５Ａ Ga-CR Ｘ When X represents = or -N=, it represents a double line (double bond). ５Ｂ The dotted line between the carbon atom and the adjacent carbon atom represents X ５Ｂ is a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ When "-" is used, it represents a single line (single bond), and X ５Ｂ Ga-CR Ｘ When R represents = or -N=, it represents a double line (double bond). ＮＸ represents a hydrogen atom or a substituent S described below. Ｘ represents a hydrogen atom or a substituent. ＸExamples of the substituent represented by the formula (I) include the groups exemplified above as the substituent W, and among these, the substituent T described below is preferred. * represents a bonding position.

[0050] Formula (Ar ３ -4) Medium, X ６ represents a sulfur atom, an oxygen atom, a selenium atom, or —NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. １２ ~Z １５ are each independently -CR Ｚ１２ = or -N=, -CR Ｚ１２ Preferably, R represents Ｚ１２ represents a hydrogen atom or a substituent. Ｚ１２ Examples of the substituent represented by the formula (I) include the groups exemplified above as the substituent W, and among these, the substituent T described below is preferred. * represents a bonding position.

[0051] Formula (Ar ３ -5) Medium, Z １６ ~Z ２１ are each independently -CR Ｚ１６ = or -N=, -CR Ｚ１６ Preferably, R represents Ｚ１６ represents a hydrogen atom or a substituent. Ｚ１６ Examples of the substituent represented by the formula (I) include the groups exemplified above as the substituent W, and among these, the substituent T described below is preferred. * represents a bonding position.

[0052] Ar ３ Among them, the formula (Ar ３ -1) or formula (Ar ３ -2) (wherein the formula (Ar ３ In the group represented by formula (1), Z ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５do not combine with each other to form a ring. ３ In the group represented by formula (2), Z ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ are more preferably not linked to each other to form a ring).

[0053] In formula (1), A １ and A ２ each independently represents a group represented by formula (A-1) or formula (A-2). Among these, A １ and A ２ At least one of A is preferably a group represented by formula (A-1), １ and A ２ and more preferably, both are groups represented by formula (A-1).

[0054] In the above formula (A-1), W １ represents an oxygen atom, a sulfur atom, and ═NR Ｗ１ , or =CR Ｗ２ R Ｗ３ Represents R Ｗ１ represents a hydrogen atom or a substituent. Ｗ１ Examples of the substituent represented by the formula (I) include the substituents exemplified above for the substituent W. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ , or -COR Ｗ６ Represents R Ｗ２ and R Ｗ３ Preferably, at least one of R represents a cyano group, and more preferably, both represent cyano groups. Ｗ４ , R Ｗ５ , and R Ｗ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. Ｗ４ , R Ｗ５ , and R Ｗ６Examples of the substituent that the aliphatic hydrocarbon group, aryl group, and heterocyclic group represented by the following formula (I) may have include the substituents exemplified for the substituent W above.

[0055] The above W １ In terms of the effects of the present invention being more excellent, it is preferable that R represents an oxygen atom or a sulfur atom, and it is more preferable that R represents an oxygen atom.

[0056] In formula (A-1), C １ represents a ring containing at least two carbon atoms (corresponding to the two carbon atoms specified in formula (A-1)), which may have a substituent. 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 includes the two carbon atoms specified in the formula. The ring may be either aromatic or non-aromatic. 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 rings forming the fused ring is preferably 1 to 4, and more preferably 1 to 3. The ring may have a heteroatom. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, a nitrogen atom, or an oxygen atom is preferred. The number of heteroatoms in the ring is preferably 0 to 10, and more preferably 0 to 5.

[0057] Above C １ The carbon atoms constituting the ring represented by the formula (I) may be substituted with other carbonyl carbons (>C=O) and / or other thiocarbonyl carbons (>C=S). The other carbonyl carbons (>C=O) and other thiocarbonyl carbons (>C=S) refer to the carbon atoms in the * part and W among the carbon atoms constituting the ring. １and the like. The substituents that the ring may have include, for example, the groups exemplified for the substituent W above. A halogen atom, an alkyl group, an aromatic ring group, an alkoxy group, or a silyl group is preferred, and a halogen atom or an alkyl group is more preferred. The alkyl group may be linear, branched, or cyclic, and linear or cyclic is preferred. The alkyl group preferably has 1 to 10 carbon atoms, and more preferably has 1 to 3 carbon atoms.

[0058] 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, 1,2-dimethyl-3,5-pyrazolidinedione, etc. (p) Benzothiophen-3(2H)-one nucleus: for example, benzothiophen-3(2H)-one, oxobenzothiophen-3(2H)-one, 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, 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.

[0059] The group represented by formula (A-1) above is preferably a group represented by formula (C-1) or formula (C-2) below, and more preferably a group represented by formula (C-1) below, in terms of achieving better effects of the present invention. In formulas (C-1) and (C-2), * represents a bonding position.

[0060]

[0061] In formula (C-1), X ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR ｃ１１ , or =CR ｃ１２ R ｃ１３ represents.ｃ１ and X ｃ２ Among these, it is preferable that each independently represents an oxygen atom or a sulfur atom, and it is more preferable that each independently represent an oxygen atom, in that the effects of the present invention are more excellent.

[0062] R ｃ１１ represents a hydrogen atom or a substituent. ｃ１１ Examples of the substituent represented by the formula (I) include the substituents exemplified above for the substituent W. ｃ１２ and R ｃ１３ each independently represents a cyano group, —SO ２ R ｃ１４ , -COOR ｃ１５ , or -COR ｃ１６ Represents R ｃ１２ and R ｃ１３ Preferably, at least one of R represents a cyano group, and more preferably, both represent cyano groups. ｃ１４ , R ｃ１５ , and R ｃ１６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. ｃ１４ , R ｃ１５ , and R ｃ１６ Examples of the substituent that the aliphatic hydrocarbon group, aryl group, and heterocyclic group represented by the following formula (I) may have include the substituents exemplified for the substituent W above.

[0063] C ３ represents an aromatic ring containing at least two carbon atoms (corresponding to the two carbon atoms specified in formula (C-1)), which may have a substituent. The number of carbon atoms in the aromatic ring is preferably 4 to 30, more preferably 5 to 12, and even more preferably 6 to 8. The number of carbon atoms includes the two carbon atoms specified in the formula. The aromatic ring may be either a monocyclic or polycyclic ring. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but is preferably an aromatic hydrocarbon ring. The C ３The aromatic ring represented by the formula (I) is preferably a benzene ring, a naphthalene ring, an anthracene ring, or a pyrene ring, and more preferably a benzene ring or a naphthalene ring. Examples of the substituent that the aromatic ring may have include the groups exemplified for the substituent W, and are preferably an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, or a halogen atom.

[0064] In formula (C-2), X ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR ｃ３１ , or =CR ｃ３２ R ｃ３３ represents. ｃ３ ~X ｃ５ In particular, it is preferable that R each independently represent an oxygen atom or a sulfur atom, and it is more preferable that R represent an oxygen atom, in that the effects of the present invention are more excellent. ｃ３１ represents a hydrogen atom or a substituent. ｃ３１ Examples of the substituent represented by the formula (I) include the substituents exemplified above for the substituent W. ｃ３２ and R ｃ３３ each independently represents a cyano group, —SO ２ R ｃ３４ , -COOR ｃ３５ , or -COR ｃ３６ Represents R ｃ３２ and R ｃ３３ Preferably, at least one of R represents a cyano group, and more preferably, both represent cyano groups. ｃ３４ , R ｃ３５ , and R ｃ３６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. ｃ３４ , R ｃ３５ , and R ｃ３６ Examples of the substituent that the aliphatic hydrocarbon group, aryl group, and heterocyclic group represented by the following formula (I) may have include the substituents exemplified for the substituent W above.

[0065] In the above formula (C-2), R ｃｘ１ and R ｃｘ２R each independently represents a hydrogen atom or a substituent. ｃｘ１ and R ｃｘ２ Examples of the substituent represented by the formula (I) include the groups exemplified by the above-mentioned substituent W, among which an alkyl group or a phenyl group is preferred, and an alkyl group is more preferred. The above-mentioned phenyl group may further have a substituent, and examples thereof include the groups exemplified by the above-mentioned substituent W.

[0066] In formula (A-2), R Ａ１ is a cyano group or —CO—Ar Ａ Represents Ar. Ａ represents an aromatic ring group or an aliphatic hydrocarbon group which may have a substituent. Ａ１ Among them, a cyano group or Ar Ａ is an aromatic ring group which may have a substituent, -CO-Ar Ａ It is preferred to represent

[0067] In the above formula (1), A １ and A ２ is a group represented by formula (A-1), the specific compound is represented by formula (A-1-1), １ and A ２ is a group represented by formula (A-2), the specific compound is represented by formula (A-2-1). In addition, in this case, when the group represented by formula (A-1) is a group represented by formula (C-1), the specific compound is represented by formula (C-1A), and when the group represented by formula (A-1) is a group represented by formula (C-2), the specific compound is represented by formula (C-2A).

[0068]

[0069] In the description at the top, the substituent S is as follows:

[0070] Substituent S: The substituent S represents a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or an aromatic ring group.

[0071] In the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, represented by the substituent S, the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, but is preferably a saturated aliphatic hydrocarbon group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, represented by the substituent S, may have an etheric oxygen atom (in other words, the -CH ２ The cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent S may be either monocyclic or polycyclic.

[0072] The aromatic ring group represented by the substituent S is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, a halogen atom, or —Si(R ＳＸ ) ３ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring may have are synonymous with the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent S.

[0073] Specific examples of the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms represented by the substituent S include linear alkyl groups having 1 to 3 carbon atoms (e.g., methyl, ethyl, and n-propyl), with an ethyl group or a methyl group being preferred, and a methyl group being more preferred. Specific examples of the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms represented by the substituent S include branched alkyl groups having 3 to 5 carbon atoms (e.g., isopropyl, sec-butyl, iso-butyl, tert-butyl, and neopentyl), with an isopropyl group, sec-butyl, iso-butyl, or tert-butyl being preferred, and an isopropyl group being more preferred. Specific examples of the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent S include cycloalkyl groups having 3 to 8 carbon atoms (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl), with cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl being preferred, and cyclopropyl being more preferred. Specific examples of the aromatic ring group represented by the substituent S include phenyl groups which may have a linear alkyl group having 1 to 3 carbon atoms.

[0074] The above R ＳＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group.

[0075] The above R ＳＸ In the linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, represented by the formula (I), the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, but is preferably a saturated aliphatic hydrocarbon group. ＳＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, which are represented by the following formula, may have an etheric oxygen atom (in other words, the —CH ２- may be replaced by -O-), and may have a halogen atom as a substituent.

[0076] The above R ＳＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring may have are synonymous with the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent S.

[0077] In the description at the top, the substituent T is as follows:

[0078] Substituent T: The substituent T is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or —Si(R ＴＸ ) ３ , a halogen atom, or an aromatic ring group.

[0079] The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, represented by the substituent T, may have an etheric oxygen atom (in other words, the —CH ２ The cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent T may be either monocyclic or polycyclic.

[0080] The aromatic ring group represented by the substituent T may have, as a substituent, a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring may have are synonymous with the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent T.

[0081] Specific examples of the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms and represented by the substituent T include linear alkyl groups having 1 to 3 carbon atoms (e.g., methyl, ethyl, and n-propyl), with a methyl group or ethyl group being preferred, and a methyl group being more preferred. Specific examples of the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms and represented by the substituent T include branched alkyl groups having 3 to 5 carbon atoms (e.g., isopropyl, sec-butyl, iso-butyl, tert-butyl, and neopentyl), with an isopropyl group, sec-butyl, iso-butyl, or tert-butyl being preferred, and an isopropyl group being more preferred. Specific examples of the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent T include cycloalkyl groups having 3 to 8 carbon atoms (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl), with cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl being preferred, and cyclopropyl being more preferred. Specific examples of the aromatic ring group represented by the substituent T include a phenyl group which may have a linear alkyl group having 1 to 3 carbon atoms as a substituent.

[0082] R ＴＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group.

[0083] The above R ＴＸIn the linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, represented by the above R ＴＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, which are represented by the following formula, may have an etheric oxygen atom (in other words, -CH ２ - may be replaced by -O-), and may have a halogen atom as a substituent.

[0084] The above R ＴＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring may have are synonymous with the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms represented by the substituent S.

[0085] R ＴＸ Among these, R preferably represents a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms. ＴＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms represented by the formula (I) has the same meaning as the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms represented by the substituent T, and the preferred embodiments are also the same.

[0086] The molecular weight of the specific compound is preferably 400 to 1,200, more preferably 400 to 1,000, 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 quantum efficiency is excellent even when a photoelectric conversion film is formed at high speed.

[0087] The specific compound preferably has an ionization potential of −5.0 to −6.0 eV in a single film from the viewpoints of stability when used as a p-type organic semiconductor and matching of the energy level with an n-type organic semiconductor.

[0088] The maximum absorption wavelength of the specific compound is preferably in the wavelength range of 400 to 600 nm, more preferably in the wavelength range of 400 to 500 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.

[0089] 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.

[0090] Specific examples of the specific compound are shown below, but the present invention is not limited to these.

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] In the specific compounds exemplified above, R represents any of the following groups: * represents a bonding position.

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] The specific compound may be purified as necessary. Examples of methods for purifying the specific compound include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, reslurry washing, reprecipitation purification, and purification using an adsorbent such as activated carbon and recrystallization purification.

[0104] 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 15 to 60% by volume, and even more preferably 15 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.

[0105] <n-Type Organic Semiconductor> The photoelectric conversion film preferably 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; condensed aromatic carbon ring compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); 5- to 7-membered heterocyclic compounds having at least one selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole, and thiazole); polyaryls 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 dianhydride; 3,4,9,10-perylenetetracarboxylic diimide derivatives; and the compounds described in paragraphs

[0056] to

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

[0106] As the n-type organic semiconductor (compound), fullerenes selected from the group consisting of fullerenes and their derivatives are preferred. Examples of fullerenes include fullerene C60, fullerene C70, fullerene C76, fullerene C78, ​​fullerene C80, fullerene C82, fullerene C84, fullerene C90, fullerene C96, fullerene C240, fullerene C540, and mixed fullerenes. Examples of fullerene derivatives include compounds in which a substituent is added to the above-mentioned fullerenes. The substituent is preferably an alkyl group, an aryl group, or a heterocyclic group. As the fullerene derivative, the compounds described in JP 2007-123707 A are preferred.

[0107] 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.

[0108] The molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.

[0109] The maximum absorption wavelength of the n-type organic semiconductor is preferably 400 nm or less, or in the range of more than 500 nm and 600 nm or less.

[0110] The photoelectric conversion film preferably has a bulk heterostructure formed in a state in which a specific compound and an n-type organic semiconductor are mixed. The bulk heterostructure is a layer in the photoelectric conversion film in which a specific compound and an 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.

[0111] The difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.

[0112] 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%.

[0113] When the n-type organic semiconductor material contains fullerenes, the content of the fullerenes relative to the total content of the n-type organic semiconductor material (film thickness in monolayer equivalent of fullerenes / total film thickness in monolayer equivalent of each n-type organic semiconductor material×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.

[0114] 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 30 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 20 to 75% by volume. It is preferable that the photoelectric conversion film is substantially composed of the specific compound, the n-type organic semiconductor, and a p-type organic semiconductor that is included as desired. "Substantially" means that the total content of the specific compound, n-type organic semiconductor, and p-type organic semiconductor relative to the total mass of the photoelectric conversion film is 90 to 100% by volume, preferably 95 to 100% by volume, and more preferably 99 to 100% by volume.

[0115] <p-Type Organic Semiconductor> The photoelectric conversion film preferably 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.

[0116] Examples of p-type organic semiconductors include triarylamine compounds (e.g., 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 described in paragraphs

[0119] to

[0158] of JP-A No. 2015-1 compounds described in paragraphs

[0044] to

[0051] of Japanese Patent Application Laid-Open No. 2012-094660, and the like), 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]thiophene (BTBT) derivatives, thieno[3,2-f:4,5-f']bis[1]benzothiophene (TBBT) derivatives, JP-A-2012-094660, and the like); Compounds described in paragraphs

[0031] to

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

[0043] to

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

[0025] to

[0037] and

[0099] to

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

[0029] to

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

[0015] to

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

[0045] to

[0053] of JP 2019-058 995, the compounds described in paragraphs

[0045] to

[0055] of WO2019 / 081416, the compounds described in paragraphs

[0063] to

[0089] of JP2019-80052, the compounds described in paragraphs

[0033] to

[0036] of JP2019-80052, the compounds described in paragraphs

[0044] to

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

[0041] to

[0046] of W2019 / 093188, etc.), the compounds described in paragraphs

[0034] to

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

[0033] to

[0036] of JP2018-206878,The compound of paragraph

[0038] of JP 2018-190755 A, the compound of paragraphs

[0019] to

[0021] of JP 2018-026559 A, the compound of paragraphs

[0031] to

[0056] of JP 2018-170487 A, the compound of paragraphs

[0036] to

[0041] of JP 2018-078270 A, the compound of paragraphs

[0055] to

[0082] of JP 2018-11 the compounds of paragraphs

[0041] to

[0050] of JP-A-3425, the compounds of paragraphs

[0044] to

[0048] of JP-A-2018-085430, the compounds of paragraphs

[0041] to

[0045] of JP-A-2018-056546, the compounds of paragraphs

[0042] to

[0049] of JP-A-2018-046267, the compounds of paragraphs

[0031] to

[0036] of JP-A-2018-014474, and WO2018 / 01646 Compounds described in paragraphs

[0036] to

[0046] of Japanese Patent Application Laid-Open No. 2020-010024, paragraphs

[0045] to

[0048] , 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. In addition, compounds (nitrogen-containing heterocyclic compounds) described in JP 2022-123944 A, JP 2022-122839 A, JP 2022-120323 A, JP 2022-120273 A, JP 2022-115832 A, JP 2022-108268 A, JP 2022-100258 A, JP 2022-181226 A, JP 2023-005703 A, JP 2022-027575 A, and JP 2021-163968 A can also be used. Examples of p-type organic semiconductors include:Compounds having a smaller ionization potential than n-type organic semiconductors can also be used. If this condition is met, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of compounds that can be used as p-type organic semiconductor compounds are listed below.

[0117]

[0118]

[0119]

[0120]

[0121] The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.

[0122] 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 20 to 50 vol%.

[0123] 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.

[0124] <Dye> The photoelectric conversion film preferably contains 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, and 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, acceptor-donor-acceptor type dyes (ADA type dyes) in which two acidic nuclei are bonded to a donor, and donor-acceptor-donor type dyes (DAD type dyes) in which two donors are bonded to an acceptor, as described in WO 2020 / 013246, WO 2022 / 168856, JP 2023-010305, and JP 2023-010299; and the like. Among these, organic dyes are preferably cyanine dyes, imidazoquinoxaline dyes, or ADA type dyes, from the viewpoint of the maximum absorption wavelength described below.

[0125] The maximum absorption wavelength of the dye is preferably in the visible light region, more preferably from 400 to 650 nm, and even more preferably from 450 to 650 nm.

[0126] 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 15 to 60 vol%, and still more preferably 15 to 50 vol%.

[0127] <Film formation method> Examples of the film formation method for the photoelectric conversion film include dry film formation methods. Examples of dry film formation methods include physical vapor deposition methods such as vapor deposition (particularly vacuum deposition), sputtering, ion plating, and MBE (Molecular Beam Epitaxy), as well as CVD (Chemical Vapor Deposition) methods such as plasma polymerization, and vacuum deposition methods are preferred. When forming the photoelectric conversion film by vacuum deposition, manufacturing conditions such as the degree of vacuum and deposition temperature can be set according to conventional methods.

[0128] 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.

[0129] [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, chromium, and nickel; mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and nanocarbon materials such as carbon nanotubes and graphene; and the like, with conductive metal oxides being preferred in terms of high conductivity and transparency.

[0130] 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.

[0131] 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 antimony- or fluorine-doped tin oxide (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metals such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and carbon materials such as carbon nanotubes and granphenes.

[0132] 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.

[0133] [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.

[0134] [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, and diacetylene, as well as derivatives thereof.

[0135] 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.

[0136] [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.

[0137] Examples of methods for producing a charge blocking film include dry film formation and wet film formation. Examples of dry film formation methods 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 methods 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.

[0138] 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.

[0139] [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.

[0140] [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.

[0141] [Image capture element] An example of an application of a photoelectric conversion element is an image capture element. An image capture 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 image capture element. For this reason, each pixel is composed of one or more photoelectric conversion elements and one or more transistors.

[0142] [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.

[0143] [Compound] The present invention also includes the invention of a compound. The compound of the present invention is the above-mentioned specific compound.

[0144] The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, processing details, processing procedures, etc. can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is as shown below. The examples should not be construed as limiting.

[0145] [Compound (Evaluation Compound)] [Method for synthesizing compound (1-1)]

[0146]

[0147] Compound (1-1-1) (2.0 mmol), compound (1-1-2) (5.0 mmol), toluene (60 mL), and piperidine (0.4 mmol) were placed in a glass reaction vessel and reacted at 100°C for 2 hours under a nitrogen atmosphere. The precipitated solid was filtered, and the resulting solid was washed successively with tetrahydrofuran (THF), N,N-dimethylacetamide (DMAc), and tetrahydrofuran (THF), followed by purification by sublimation to obtain 0.90 mmol of compound (1-1) (yield 45%). The structure of compound (1-1) was confirmed by LDI-MS. LDI-MS (compound (1-1)): 671 (M ＋ )

[0148] [Compounds (Evaluation Compounds)] Other specific compounds were also synthesized with reference to the synthesis method described above. The specific compounds and comparative compounds used in the tests are shown below. In the following, compounds (1-1) to (1-6), compounds (2-1) to (2-21), compounds (3-1) to (3-3), compounds (4-1) to (4-10), compounds (5-1) to (5-2), and compounds (6-1) to (6-2) are specific compounds. Hereinafter, the specific compounds and comparative compounds are also collectively referred to as evaluation compounds. The evaluation compounds were used in the production of photoelectric conversion elements, which will be described later.

[0149] <Specific compound>

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] <Comparative Compounds>

[0158]

[0159] [P-Type Organic Semiconductor] The p-type organic semiconductors shown below were used as p-type organic semiconductors for evaluation in the production of photoelectric conversion elements described below.

[0160]

[0161] [n-type organic semiconductor] Fullerene C ６０ (This may also be referred to as "C60" in the tables below.) was used as an n-type organic semiconductor for evaluation in the production of a photoelectric conversion element, which will be described later.

[0162] [Dye] In Test Y described later, the dyes shown below were used as dyes for evaluation.

[0163]

[0164]

[0165] [Evaluation] [Test X] <Preparation of Photoelectric Conversion Element> A photoelectric conversion element having the configuration shown in FIG. 2 was prepared using an evaluation compound (specific compound or comparative compound). 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 the following 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). Furthermore, each material shown in Tables 1 and 2 (evaluation compound, p-type organic semiconductor, and n-type organic semiconductor (fullerene (C ６０)) were deposited in the component ratios (volume ratios) shown in Tables 1 and 2 to form a photoelectric conversion film 12 having a bulk heterostructure. Furthermore, the following compound (EB-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). Amorphous ITO was formed 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 Thereafter, the layer was heated at 150° C. for 30 minutes in a glove box under a nitrogen atmosphere to prepare a photoelectric conversion element.

[0166]

[0167] <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.

[0168] <Quantum Efficiency> The quantum efficiency of each of the obtained photoelectric conversion elements was measured by the following method. ５ After applying a voltage so as to obtain an electric field strength of 100 V / cm, the quantum efficiency (photoelectric conversion efficiency) at a wavelength of 460 nm was evaluated by irradiating the device with light from the upper electrode (transparent conductive film) side, and the quantum efficiency was calculated according to formula (S1).

[0169] Formula (S1): Quantum efficiency (relative ratio) = (quantum efficiency at a wavelength of 460 nm of each photoelectric conversion element of an Example or Comparative Example) / (quantum efficiency at a wavelength of 460 nm of the photoelectric conversion element of a reference Example) "A": quantum efficiency of 1.6 or more "B": quantum efficiency of 1.2 or more and less than 1.6 "C": quantum efficiency of 0.8 or more and less than 1.2 "D": quantum efficiency of 0.4 or more and less than 0.8 "E": quantum efficiency less than 0.4 Note that with regard to Examples 1-1 to 1-44 and Comparative Examples 1-1 to 1-3 listed in Table 1, the reference example in formula (S1) is Example 1-39, and with regard to Examples 2-1 to 2-3 and Comparative Example 2-1 listed in Table 2, the reference example in formula (S1) is Example 2-1.

[0170] <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 device so that the intensity was 1000 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 460 nm at that time was measured with an oscilloscope to measure the rise time from 0% signal intensity to 97% signal intensity, and the relative response speed was evaluated according to formula (S2). Formula (S2): Relative response speed = (rise time at a wavelength of 460 nm of each photoelectric conversion element of an Example or Comparative Example) / (rise time at a wavelength of 460 nm of the photoelectric conversion element of the reference Example) "A": relative response speed less than 0.5 "B": relative response speed 0.5 or more and less than 1.0 "C": relative response speed 1.0 or more and less than 1.5 "D": relative response speed 1.5 or more and less than 2.0 "E": relative response speed 2.0 or more Note that with regard to Examples 1-1 to 1-44 and Comparative Examples 1-1 to 1-3 listed in Table 1, the reference example in formula (S2) is Example 1-39, and with regard to Examples 2-1 to 2-3 and Comparative Example 2-1 listed in Table 2, the reference example in formula (S2) is Example 2-1.

[0171] <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 voltage was changed to 7.5 × 10 ４ The response speed at a wavelength of 460 nm for each photoelectric conversion element of the Examples and Comparative Examples was measured. The response speed at a wavelength of 460 nm for each photoelectric conversion element of the Examples and Comparative Examples was measured. The response speed was calculated and evaluated according to the following formula (S3): ４ V / cm) / (2.0×10 at a wavelength of 460 nm for each photoelectric conversion element of the Examples and Comparative Examples ５ V / cm) In the formula (S3), the photoelectric conversion elements in the numerator and denominator are the same. For example, with regard to Example 1-1, the photoelectric conversion efficiency of Example 1-1 at a wavelength of 460 nm is 7.5 × 10 ４ V / cm and the photoelectric conversion efficiency of Example 1-1 at a wavelength of 460 nm of 2.0 × 10 ５ "A": The electric field strength dependency of the response speed is less than 2.0. "B": The electric field strength dependency of the response speed is 2.0 or more and less than 3.0. "C": The electric field strength dependency of the response speed is 3.0 or more and less than 4.0. "D": The electric field strength dependency of the response speed is 4.0 or more and less than 5.0. "E": The electric field strength dependency of the response speed is 5.0 or more.

[0172] The evaluation results of the above test X are shown in Tables 1 and 2. The component ratios in Tables 1 and 2 ａ The volume ratios (from left to right) represent the evaluation compound, the p-type organic semiconductor, and the n-type organic semiconductor. １ "Structure of ", "Ar ３ "Structure of" and "A １ and A ２ The columns "Structure of" show the structure of each of the above-mentioned parts when the evaluation compound is applied to formula (1). １ In the structure of "A", "A" is X in formula (1). １ Ga-CR Ｃ１ R Ｃ２-or-SiR Ｃ１ R Ｃ２ -, and "B" means the case where X in formula (1) １ Ga-NR Ｎ -, and "C" means the case where X in formula (1) １ But, -NR Ｎ -, -CR Ｃ１ R Ｃ２ - and -SiR Ｃ１ R Ｃ２ - means that the group does not fall under the category of - (when it represents a sulfur atom or an oxygen atom). ３ In the structure of "A", "A" is Ar ３ "A" in the remarks column in Tables 1 and 2 means that the group "A" corresponds to an optionally substituted monocyclic arylene group or an optionally substituted monocyclic heteroarylene group, and "B" means that the group "A" does not correspond to the above. １ and A ２ In the structure of " １ and A ２ When the structure represents a group represented by formula (C-1), it is represented as "(C-1)", when it represents a group represented by formula (C-2), it is represented as "(C-2)", and when it represents a group represented by formula (A-2), it is represented as "(A-2)".

[0173]

[0174]

[0175] From the results shown in Tables 1 and 2, it is clear that the photoelectric conversion elements of the examples are excellent in all of quantum efficiency, response, and electric field strength dependency of response speed when receiving blue light.

[0176] Comparison of the examples has confirmed that when D-1 is used as a p-type organic semiconductor, the response and the electric field strength dependency of the response speed when blue light is received are more excellent (see, in particular, the comparison between Examples 1-1 and 1-2). ３represents a monocyclic arylene group which may have a substituent or a monocyclic heteroarylene group which may have a substituent, the quantum efficiency when blue light is received is confirmed to be more excellent (see the results of Examples 1-8, 1-9, and 1-15 to 1-17 in particular). １ and A ２ represents a group represented by formula (C-1) or formula (C-2), it was confirmed that the quantum efficiency, responsiveness, and electric field strength dependency of the response speed when blue light was received were all superior (see, in particular, the results of Examples 2-1 and 2-2). １ Ga-NR Ｎ -, -CR Ｃ１ R Ｃ２ - or -SiR Ｃ１ R Ｃ２ It was confirmed that when blue light was received, the quantum efficiency, response, and electric field strength dependency of the response speed were all superior when X in formula (1) represented - (see, in particular, the results of Examples 1-39 to 1-40). １ Ga-CR Ｃ１ R Ｃ２ -or-SiR Ｃ１ R Ｃ２ When the symbol "-" is used, it was confirmed that the response speed when blue light was received was superior (see the results of Examples 1-1, 1-3 to 1-6, and 2-1 in particular).

[0177] [Test Y] <Fabrication of photoelectric conversion element> Each material shown in Table 3 and Table 4 (evaluation compound, p-type organic semiconductor, n-type organic semiconductor (fullerene (C ６０ ), and dye) were vapor-deposited in the component ratios (volume ratios) shown in Tables 3 and 4 to prepare a photoelectric conversion film 12 having a bulk heterostructure. The photoelectric conversion elements of each example and each comparative example were prepared in the same manner as in Test X, except that the photoelectric conversion film 12 had a bulk heterostructure.

[0178] <Dark Current> The dark current was measured in the same manner as in Test X. As a result, the dark current was 50 nA / cm in all the photoelectric conversion elements. ２ It was confirmed that the dark current was sufficiently low.

[0179] <Quantum Efficiency> The quantum efficiency of each of the obtained photoelectric conversion elements was measured by the following method. ５ After applying a voltage so as to obtain an electric field strength of 100 V / cm, the quantum efficiency (photoelectric conversion efficiency) at a wavelength of 460 nm or 600 nm was evaluated by irradiating the device with light from the upper electrode (transparent conductive film) side, and the quantum efficiency was calculated according to formula (S4).

[0180] Formula (S4): Quantum efficiency (relative ratio) = (quantum efficiency at a wavelength of 460 nm or 600 nm of each photoelectric conversion element of an Example or Comparative Example) / (quantum efficiency at a wavelength of 460 nm or 600 nm of the photoelectric conversion element of a reference Example) "A": quantum efficiency of 1.6 or more "B": quantum efficiency of 1.2 or more and less than 1.6 "C": quantum efficiency of 0.8 or more and less than 1.2 "D": quantum efficiency of 0.4 or more and less than 0.8 "E": quantum efficiency less than 0.4 Note that with regard to Examples 3-1 to 3-25 and Comparative Examples 3-1 to 3-3 listed in Table 3, the reference example in formula (S4) is Example 3-25, and with regard to Examples 4-1 to 4-3 and Comparative Example 4-1 listed in Table 4, the reference example in formula (S4) is Example 4-1.

[0181] <Response Speed> The response speed of each of the obtained photoelectric conversion elements was evaluated by the following method. ５A voltage was applied to the sample so that the intensity was 1000 V / cm. The LED was then momentarily turned on to irradiate the sample from the upper electrode (transparent conductive film) side. The photocurrent at a wavelength of 460 nm or 600 nm was measured with an oscilloscope to calculate the rise time from 0% signal intensity to 97% signal intensity, and the relative response speed was evaluated according to formula (S5). Note that when calculating the relative response speed, the numerator and denominator are the rise times at the same wavelength. Formula (S5): relative response speed = (rise time at a wavelength of 460 nm or 600 nm of each photoelectric conversion element of an Example or Comparative Example) / (rise time at a wavelength of 460 nm or 600 nm of the photoelectric conversion element of a reference Example) "A": relative response speed less than 0.5 "B": relative response speed 0.5 or more and less than 1.0 "C": relative response speed 1.0 or more and less than 1.5 "D": relative response speed 1.5 or more and less than 2.0 "E": relative response speed 2.0 or more Note that with regard to Examples 3-1 to 3-29 and Comparative Examples 3-1 to 3-3 listed in Table 3, the reference example in formula (S5) is Example 3-25, and with regard to Examples 4-1 to 4-3 and Comparative Example 4-1 listed in Table 4, the reference example in formula (S5) is Example 4-1.

[0182] <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 voltage was changed to 7.5 × 10 ４ The response speed at each wavelength of each photoelectric conversion element of the example or comparative example was measured. The electric field strength dependency of the response speed was calculated and evaluated according to the formula (S6). Formula (S6): Electric field strength dependency of response speed = (7.5 × 10 ４ V / cm) / (2.0×10 at each wavelength for each photoelectric conversion element of the Examples or Comparative Examples ５V / cm) In formula (S6), the photoelectric conversion elements in the numerator and denominator are the same. "A": The electric field strength dependency of the response speed is less than 2.0 "B": The electric field strength dependency of the response speed is 2.0 or more and less than 3.0 "C": The electric field strength dependency of the response speed is 3.0 or more and less than 4.0 "D": The electric field strength dependency of the response speed is 4.0 or more and less than 5.0 "E": The electric field strength dependency of the response speed is 5.0 or more

[0183] The evaluation results of Test Y are shown in Tables 3 and 4. Component ratios in Tables 3 and 4 ａ The volume ratios (from left to right) represent the evaluation compound, p-type organic semiconductor, n-type organic semiconductor, and dye. １ "Structure of ", "Ar ３ "Structure of" and "A １ and A ２ The columns "Structure of" show the structure of each of the above-mentioned parts when the evaluation compound is applied to formula (1). １ In the structure of "A", "A" is X in formula (1). １ Ga-CR Ｃ１ R Ｃ２ -or-SiR Ｃ１ R Ｃ２ -, and "B" means the case where X in formula (1) １ Ga-NR Ｎ -, and "C" means the case where X in formula (1) １ But, -NR Ｎ -, -CR Ｃ１ R Ｃ２ - and -SiR Ｃ１ R Ｃ２ - means that the group does not fall under the category of - (when it represents a sulfur atom or an oxygen atom). ３ In the structure of "A", "A" is Ar ３ "A" in the remarks column in Tables 3 and 4 means that the group "A" corresponds to an optionally substituted monocyclic arylene group or an optionally substituted monocyclic heteroarylene group, and "B" means that the group "A" does not correspond to the above. １ and A ２ In the structure of " １ and A２ When the structure represents a group represented by formula (C-1), it is represented as "(C-1)", when it represents a group represented by formula (C-2), it is represented as "(C-2)", and when it represents a group represented by formula (A-2), it is represented as "(A-2)".

[0184]

[0185]

[0186]

[0187] From the results shown in Tables 3 and 4, it is clear that the photoelectric conversion elements of the examples are excellent in all of quantum efficiency, responsiveness, and electric field strength dependency of response speed when receiving blue light.

[0188] Comparison of the examples has confirmed that when D-1 is used as a p-type organic semiconductor, the response and the electric field strength dependency of the response speed when blue light is received are more excellent (see, in particular, the comparison between Examples 3-1 and 3-2). ３ represents a monocyclic arylene group which may have a substituent or a monocyclic heteroarylene group which may have a substituent, the quantum efficiency when blue light is received is confirmed to be more excellent (see the results of Examples 3-15 in particular). １ and A ２ represents a group represented by formula (C-1) or formula (C-2), it was confirmed that the quantum efficiency, responsiveness, and electric field strength dependency of the response speed when blue light was received were all superior (see, in particular, the results of Examples 4-1 and 4-2). １ Ga-NR Ｎ -, -CR Ｃ１ R Ｃ２ - or -SiR Ｃ１ R Ｃ２ It was confirmed that when blue light was received, the quantum efficiency, response, and electric field strength dependency of the response speed were all superior when X in formula (1) represented - (see, in particular, the results of Example 3-25). １ Ga-CR Ｃ１ RＣ２ -or-SiR Ｃ１ R Ｃ２ When the symbol "-" is used, it was confirmed that the response speed when blue light was received was superior (see the results of Examples 3-1 to 3-13 and 4-1 in particular).

[0189] 10a, 10b Photoelectric conversion element 11 Conductive film (lower electrode) 12 Photoelectric conversion film 15 Transparent conductive film (upper electrode) 16A Electron blocking film 16B Hole blocking film

Claims

1. A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, The photoelectric conversion element, wherein the photoelectric conversion film contains a compound represented by formula (1). 【Chemistry 1】 In formula (1), R １ and R ２ each independently represents a hydrogen atom or a substituent. X １ is -NR Ｎ -, -CR Ｃ１ R Ｃ２ --, --SiR Ｃ１ R Ｃ２ -, -GeR Ｃ１ R Ｃ２ --OCR Ｃ１ R Ｃ２ represents a sulfur atom, an oxygen atom, or a selenium atom. Ｎ , R Ｃ１ , and R Ｃ２ Each independently represents a substituent S. Ｃ１ and R Ｃ２ may be linked to each other to form a ring. Ar １ and Ar ２ each independently represents a group represented by formula (Ar-1) or formula (Ar-2). １ and Ar ２ At least one of the groups represented by formula (Ar-1) is a group represented by formula (Ar-2). Ar ３ represents an optionally substituted monocyclic or bicyclic arylene group, or an optionally substituted monocyclic or bicyclic heteroarylene group. A １ and A ２ each independently represents a group represented by formula (A-1) or formula (A-2). In formula (Ar-1), Z １ ~Z ３ Each independently represents -CR Ｚ１ = or -N=. Ｚ１ represents a hydrogen atom or a substituent. * １ is X in formula (1). １ represents the bonding position to a 5- or 6-membered ring containing ２ is -C(R １ ) = A １ or Ar ３ represents the bonding position with In formula (Ar-2), X ２ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a substituent S. Z ４ is -CR Ｚ４ = or -N=. Ｚ４ represents a hydrogen atom or a substituent. * ３ is X in formula (1). １ represents the bonding position to a 5- or 6-membered ring containing ４ is -C(R １ ) = A １ or Ar ３ represents the bonding position with In formula (A-1), C １ represents a ring containing at least two carbon atoms which may have a substituent. W １ is an oxygen atom, a sulfur atom, ═NR Ｗ１ , or = CR Ｗ２ R Ｗ３ Represents R Ｗ１ represents a hydrogen atom or a substituent. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ , or -COR Ｗ６ Represents R Ｗ４ , R Ｗ５ , and R Ｗ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. * indicates the bond position. In formula (A-2), R Ａ１ is a cyano group, -CO-Ar Ａ or -CO-O-Ar Ａ Represents Ar. Ａ represents an aromatic ring group or an aliphatic hydrocarbon group which may have a substituent. * indicates the bond position. Substituent S: The substituent S represents a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, a halogen atom, or -Si(R ＳＸ ) ３ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which the aromatic ring group may have may have an ether oxygen atom or a halogen atom as a substituent. The R ＳＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＳＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＳＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＳＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

2. The R Ｚ１ and the R Ｚ４ The photoelectric conversion element according to claim 1 , wherein the substituent represented by the formula (I) represents a substituent T. Substituent T: The substituent T is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, -Si(R ＴＸ ) ３ , a halogen atom, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. In addition, the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring group may have may have an etheric oxygen atom or may have a halogen atom as a substituent. The R ＴＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＴＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＴＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＴＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

3. The Ar ３ Formula (Ar ３ -1) to formula (Ar ３ 2. The photoelectric conversion element according to claim 1, wherein the group is represented by the formula: 【Chemistry 2】 Formula (Ar ３ -1) Medium, Z ５ ~Z ８ Each independently represents -CR Ｚ５ = or -N=. Ｚ５ represents a hydrogen atom or a substituent. ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ may be linked together to form a monocyclic ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ may be linked together to form a monocyclic ring. ５ ~Z ８ Both are -CR Ｚ５ When = represents Z ５ and Z ６ The two R's in Ｚ５ And Z. ７ and Z ８ The two R's in Ｚ５ may be linked to each other to form a monocyclic ring. * indicates the bond position. Formula (Ar ３ -2) Medium, X ３ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. Z ９ and Z １０ Each independently represents -CR Ｚ９ = or -N=. Ｚ９ represents a hydrogen atom or a substituent. ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ may be linked to each other to form a monocyclic ring. * indicates the bond position. Formula (Ar ３ -3) Medium, X ４ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. Z １１ is -CR Ｚ１１ = or -N=. Ｚ１１ represents a hydrogen atom or a substituent. X ５Ａ and X ５Ｂ one of the groups is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ -, and the other represents -CR Ｘ = or -N=. ＮＸ represents a hydrogen atom or a substituent S. Ｘ represents a hydrogen atom or a substituent. * indicates the bond position. Formula (Ar ３ -4) Medium, X ６ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. Z １２ ~Z １５ Each independently represents -CR Ｚ１２ = or -N=. Ｚ１２ represents a hydrogen atom or a substituent. * indicates the bond position. Formula (Ar ３ -5) Medium, Z １６ ~Z ２１ Each independently represents -CR Ｚ１６ = or -N=. Ｚ１６ represents a hydrogen atom or a substituent. * indicates the bond position. Substituent S: The substituent S represents a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, a halogen atom, or -Si(R ＳＸ ) ３ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which the aromatic ring group may have may have an ether oxygen atom or a halogen atom as a substituent. The R ＳＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＳＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＳＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＳＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

4. The R Ｚ５ , the R Ｚ９ , the R Ｚ１１ , the R Ｚ１２ , the R Ｚ１６ and the R Ｘ The photoelectric conversion element according to claim 3 , wherein the substituent represented by the following formula (I) represents a substituent T. Substituent T: The substituent T is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, -Si(R ＴＸ ) ３ , a halogen atom, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. In addition, the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring group may have may have an etheric oxygen atom or may have a halogen atom as a substituent. The R ＴＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＴＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＴＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＴＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

5. The Ar ３ is represented by the formula (Ar ３ -1) or the formula (Ar ３ The photoelectric conversion element according to claim 3, wherein the group represented by the formula (Ar -2) is ３ In the group represented by formula (1), Z ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ３ In the group represented by (2), Z ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ do not combine with each other to form a ring.

6. The above A １ and A ２ The photoelectric conversion element according to claim 1, wherein represents a group represented by formula (A-1).

7. 2. The photoelectric conversion element according to claim 1, wherein the group represented by formula (A-1) is a group represented by formula (C-1) or formula (C-2). 【Chemistry 3】 In formula (C-1), X ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR ｃ１１ , or = CR ｃ１２ R ｃ１３ Represents R ｃ１１ represents a hydrogen atom or a substituent. ｃ１２ and R ｃ１３ each independently represents a cyano group, —SO ２ R ｃ１４ , -COOR ｃ１５ , or -COR ｃ１６ Represents ｃ１４ , R ｃ１５ , and R ｃ１６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. C ３ represents an aromatic ring containing at least two carbon atoms which may have a substituent. * indicates the bond position. In formula (C-2), X ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR ｃ３１ , or = CR ｃ３２ R ｃ３３ Represents ｃ３１ represents a hydrogen atom or a substituent. ｃ３２ and R ｃ３３ each independently represents a cyano group, —SO ２ R ｃ３４ , -COOR ｃ３５ , or -COR ｃ３６ Represents ｃ３４ , R ｃ３５ , and R ｃ３６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. R ｃｘ１ and R ｃｘ２ each independently represents a hydrogen atom or a substituent. * indicates the bond position.

8. The X １ But -NR Ｎ -, -CR Ｃ１ R Ｃ２ - or -SiR Ｃ１ R Ｃ２ The photoelectric conversion element according to any one of claims 1 to 7, wherein

9. the photoelectric conversion film further contains an n-type organic semiconductor, The photoelectric conversion element according to any one of claims 1 to 7, wherein the photoelectric conversion film has a bulk heterostructure formed in a state in which the compound represented by formula (1) and the n-type organic semiconductor are mixed.

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

11. The photoelectric conversion element according to any one of claims 1 to 7, wherein the photoelectric conversion film further contains a p-type organic semiconductor.

12. The photoelectric conversion element according to any one of claims 1 to 7, wherein the photoelectric conversion film further contains a dye.

13. An imaging device comprising the photoelectric conversion element according to any one of claims 1 to 7.

14. An optical sensor comprising the photoelectric conversion element according to any one of claims 1 to 7.

15. A compound represented by formula (1). 【Chemistry 4】 In formula (1), R １ and R ２ each independently represents a hydrogen atom or a substituent. X １ is -NR Ｎ -, -CR Ｃ１ R Ｃ２ --, --SiR Ｃ１ R Ｃ２ -, -GeR Ｃ１ R Ｃ２ --OCR Ｃ１ R Ｃ２ represents a sulfur atom, an oxygen atom, or a selenium atom. Ｎ , R Ｃ１ , and R Ｃ２ Each independently represents a substituent S. Ｃ１ and R Ｃ２ may be linked to each other to form a ring. Ar １ and Ar ２ each independently represents a group represented by formula (Ar-1) or formula (Ar-2). １ and Ar ２ At least one of the groups represented by formula (Ar-1) is a group represented by formula (Ar-2). Ar ３ represents an optionally substituted monocyclic or bicyclic arylene group, or an optionally substituted monocyclic or bicyclic heteroarylene group. A １ and A ２ each independently represents a group represented by formula (A-1) or formula (A-2). In formula (Ar-1), Z １ ~Z ３ Each independently represents -CR Ｚ１ = or -N=. Ｚ１ represents a hydrogen atom or a substituent. * １ is X in formula (1). １ represents the bonding position to a 5- or 6-membered ring containing ２ is -C(R １ ) = A １ or Ar ３ represents the bonding position with In formula (Ar-2), X ２ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a substituent S. Z ４ is -CR Ｚ４ = or -N=. Ｚ４ represents a hydrogen atom or a substituent. * ３ is X in formula (1). １ represents the bonding position to a 5- or 6-membered ring containing ４ is -C(R １ ) = A １ or Ar ３ represents the bonding position with In formula (A-1), C １ represents a ring containing at least two carbon atoms which may have a substituent. W １ is an oxygen atom, a sulfur atom, ═NR Ｗ１ , or = CR Ｗ２ R Ｗ３ Represents Ｗ１ represents a hydrogen atom or a substituent. Ｗ２ and R Ｗ３ each independently represents a cyano group, —SO ２ R Ｗ４ , -COOR Ｗ５ , or -COR Ｗ６ Represents Ｗ４ , R Ｗ５ , and R Ｗ６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. * indicates the bond position. In formula (A-2), R Ａ１ is a cyano group, -CO-Ar Ａ or -CO-O-Ar Ａ Represents Ar. Ａ represents an aromatic ring group or an aliphatic hydrocarbon group which may have a substituent. * indicates the bond position. Substituent S: The substituent S represents a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, a halogen atom, or -Si(R ＳＸ ) ３ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which the aromatic ring group may have may have an ether oxygen atom or a halogen atom as a substituent. The R ＳＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＳＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＳＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＳＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

16. The R Ｚ１ and the R Ｚ４ The compound according to claim 15, wherein the substituent represented by the formula: represents the substituent T. Substituent T: The substituent T is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, -Si(R ＴＸ ) ３ , a halogen atom, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. In addition, the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring group may have may have an etheric oxygen atom or may have a halogen atom as a substituent. The R ＴＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＴＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＴＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＴＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

17. The Ar ３ Formula (Ar ３ -1) to formula (Ar ３ The compound according to claim 15, wherein the compound represents a group represented by: 【Chemistry 5】 Formula (Ar ３ -1) Medium, Z ５ ~Z ８ Each independently represents -CR Ｚ５ = or -N=. Ｚ５ represents a hydrogen atom or a substituent. ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ may be linked together to form a monocyclic ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ may be linked together to form a monocyclic ring. ５ ~Z ８ Both are -CR Ｚ５ When representing =, Z ５ and Z ６ The two R's in Ｚ５ And Z. ７ and Z ８ The two R's in Ｚ５ may be linked to each other to form a monocyclic ring. * indicates the bond position. Formula (Ar ３ -2) Medium, X ３ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. Z ９ and Z １０ Each independently represents -CR Ｚ９ = or -N=. Ｚ９ represents a hydrogen atom or a substituent. ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ may be linked to each other to form a monocyclic ring. * indicates the bond position. Formula (Ar ３ -3) Medium, X ４ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. Z １１ is -CR Ｚ１１ = or -N=. Ｚ１１ represents a hydrogen atom or a substituent. X ５Ａ and X ５Ｂ one of the groups is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ -, and the other represents -CR Ｘ = or -N=. ＮＸ represents a hydrogen atom or a substituent S. Ｘ represents a hydrogen atom or a substituent. * indicates the bond position. Formula (Ar ３ -4) Medium, X ６ is a sulfur atom, an oxygen atom, a selenium atom, or -NR ＮＸ - represents. ＮＸ represents a hydrogen atom or a substituent S. Z １２ ~Z １５ Each independently represents -CR Ｚ１２ = or -N=. Ｚ１２ represents a hydrogen atom or a substituent. * indicates the bond position. Formula (Ar ３ -5) Medium, Z １６ ~Z ２１ Each independently represents -CR Ｚ１６ = or -N=. Ｚ１６ represents a hydrogen atom or a substituent. * indicates the bond position. Substituent S: The substituent S represents a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, a halogen atom, or -Si(R ＳＸ ) ３ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which the aromatic ring group may have may have an ether oxygen atom or a halogen atom as a substituent. The R ＳＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＳＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＳＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＳＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

18. The R Ｚ５ , the R Ｚ９ , the R Ｚ１１ , the R Ｚ１２ , the R Ｚ１６ and the R Ｘ The compound according to claim 17, wherein the substituent represented by the formula: represents the substituent T. Substituent T: The substituent T is a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, -Si(R ＴＸ ) ３ , a halogen atom, or an aromatic ring group. The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms may have an ethereal oxygen atom or a halogen atom as a substituent. The aromatic ring group may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. In addition, the linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms that the aromatic ring group may have may have an etheric oxygen atom or may have a halogen atom as a substituent. The R ＴＸ represents a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, a branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms, or an aromatic ring group. The R ＴＸ The linear aliphatic hydrocarbon group having 1 to 4 carbon atoms, the branched aliphatic hydrocarbon group having 3 or 4 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 or 4 carbon atoms represented by the following formula (1) may have an ethereal oxygen atom or may have a halogen atom as a substituent. The R ＴＸ The aromatic ring group represented by the formula (I) may have a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms, or a halogen atom as a substituent. ＴＸ The linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, and the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms which may be contained in the aromatic ring group represented by the formula (I) may have an ether oxygen atom or a halogen atom as a substituent.

19. The Ar ３ is represented by the formula (Ar ３ -1) or the formula (Ar ３ The compound according to claim 17, wherein the compound is a group represented by the formula (Ar -2). ３ In the group represented by formula (1), Z ５ and Z ６ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ７ and Z ８ Both are -CR Ｚ５ =, two R Ｚ５ do not combine with each other to form a ring. ３ In the group represented by (2), Z ９ and Z １０ Both are -CR Ｚ９ =, two R Ｚ９ do not combine with each other to form a ring.

20. The above A １ and A ２ represents a group represented by formula (A-1).

21. The compound according to claim 15, wherein the group represented by formula (A-1) is a group represented by formula (C-1) or formula (C-2). 【Chemistry 6】 In formula (C-1), X ｃ１ and X ｃ２ each independently represents an oxygen atom, a sulfur atom, or ═NR ｃ１１ , or = CR ｃ１２ R ｃ１３ Represents ｃ１１ represents a hydrogen atom or a substituent. ｃ１２ and R ｃ１３ each independently represents a cyano group, —SO ２ R ｃ１４ , -COOR ｃ１５ , or -COR ｃ１６ Represents ｃ１４ , R ｃ１５ , and R ｃ１６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. C ３ represents an aromatic ring containing at least two carbon atoms which may have a substituent. * indicates the bond position. In formula (C-2), X ｃ３ ~X ｃ５ each independently represents an oxygen atom, a sulfur atom, or ═NR ｃ３１ , or = CR ｃ３２ R ｃ３３ Represents ｃ３１ represents a hydrogen atom or a substituent. ｃ３２ and R ｃ３３ each independently represents a cyano group, —SO ２ R ｃ３４ , -COOR ｃ３５ , or -COR ｃ３６ Represents ｃ３４ , R ｃ３５ , and R ｃ３６ each independently represents an aliphatic hydrocarbon group which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. R ｃｘ１ and R ｃｘ２ each independently represents a hydrogen atom or a substituent. * indicates the bond position.

22. The X １ But -CR Ｃ１ R Ｃ２ -or-SiR Ｃ１ R Ｃ２ The compound according to any one of claims 15 to 21, wherein

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