Photoelectric conversion elements, image sensors, light sensors, compounds

Abstract

The present invention provides a photoelectric conversion element, an imaging element, an optical sensor, and a compound in which variations in dark current are small and exceptional photoelectric conversion efficiency is obtained. The photoelectric conversion element according to the present invention has an electroconductive film, a photoelectric conversion film, and a transparent electroconductive film in the stated order, the photoelectric conversion film containing a compound represented by formula (1).

Description

[Technical Field]

[0001] The present invention relates to a photoelectric conversion element, an image sensor, a light sensor, and a compound. [Background technology]

[0002] In recent years, the development of devices having photoelectric conversion films has progressed. For example, Patent Document 1 discloses a compound represented by the following formula as a material applicable to photoelectric conversion devices.

[0003] [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2016 / 120166 [Overview of the project] [Problems that the invention aims to solve]

[0005] In recent years, with the increasing demand for improved performance in image sensors and optical sensors, there has been a growing need for further improvements in the various characteristics required of the photoelectric conversion elements used in them. For example, photoelectric conversion elements are required to have low variation in dark current and excellent photoelectric conversion efficiency. In this specification, "small variation in dark current" means that when multiple photoelectric conversion elements are fabricated under identical conditions (e.g., materials, content, and manufacturing method, etc.) and the dark current of each photoelectric conversion element is measured, the ratio of the highest dark current among all photoelectric conversion elements to the lowest dark current among all photoelectric conversion elements (highest dark current among all photoelectric conversion elements / lowest dark current among all photoelectric conversion elements) is small. In other words, small variation in dark current indicates that photoelectric conversion elements with equivalent dark current performance can be reliably obtained.

[0006] The present inventors investigated photoelectric conversion elements using compounds disclosed in Patent Document 1, etc., and found that the dark current variability was large and the photoelectric conversion efficiency was also poor.

[0007] The present invention aims to provide a photoelectric conversion element that exhibits low variation in dark current and excellent photoelectric conversion efficiency. Furthermore, the present invention also aims to provide an image sensor, a photosensor, and a compound. [Means for solving the problem]

[0008] As a result of diligent research into the above-mentioned problems, the inventors of this invention discovered that the above-mentioned problems can be solved by using a compound having a predetermined structure in a photoelectric conversion film, and thus completed the present invention.

[0009] [1] A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, A photoelectric conversion element wherein the above-mentioned photoelectric conversion film contains a compound represented by formula (1) described later. [2] The photoelectric conversion element according to [1], wherein the compound represented by formula (1) above includes a compound represented by any of the following formulas (11) to (38). [3] The photoelectric conversion element according to [2], wherein the compound represented by formula (1) above includes a compound represented by any of the following: formulas (11) to (13), formulas (17) to (19), formulas (23) to (26), and formulas (29) to (32). [4] The photoelectric conversion element according to [3], wherein the compound represented by formula (1) above includes a compound represented by any of the following: formula (11), formula (12), formula (17), formula (18), formula (23), formula (24), formula (29), and formula (30). [5] The photoelectric conversion element according to [4], wherein the compound represented by formula (1) above includes the compound represented by formula (11) above or the compound represented by formula (12) above. [6] A photoelectric conversion element according to any one of [1] to [5], wherein D comprises at least one ring selected from the group consisting of a furan ring, a thiophene ring, a thiazole ring, and an oxazole ring. [7] A photoelectric conversion element according to any one of [1] to [6], wherein D has two or four atoms or groups selected from the group consisting of -N=, halogen atoms, trifluoromethyl groups and cyano groups, and A has three to four atoms or groups selected from the group consisting of -N=, halogen atoms, cyano groups, trifluoromethyl groups, sulfonyl groups, carbonyl groups and thiocarbonyl groups. [8] A photoelectric conversion element according to any one of [1] to [7], wherein the molecular weight of the compound represented by the above formula (1) is 900 or less. [9] The photoelectric conversion element according to any one of [1] to [8], wherein the above-mentioned photoelectric conversion film further comprises an n-type organic semiconductor.

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

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

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

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

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

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

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

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

[13] .

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

[13] .

[16] A compound represented by formula (1), which will be described later.

[17] The compound described in

[16] , which includes a compound represented by any of the following formulas (11) to (38).

[18] The compound described in

[17] , which is a compound represented by any of the above formulas (11) to (13), (17) to (19), (23) to (26), and (29) to (32).

[19] The compound according to

[18] , which is a compound represented by any of the above formulas (11), (12), (17), (18), (23), (24), (29), and (30).

[20] The compound described in

[19] , which is a compound represented by formula (11) or a compound represented by formula (12). 〔twenty one〕 The compound according to any one of

[16] to

[20] , wherein D comprises at least one ring selected from the group consisting of a furan ring, a thiophene ring, a thiazole ring, and an oxazole ring. 〔twenty two〕 The compound according to any one of

[16] to

[21] , wherein D has -N=, two or four atoms or groups selected from the group consisting of halogen atoms, trifluoromethyl groups and cyano groups, and A has -N=, three to four atoms or groups selected from the group consisting of halogen atoms, cyano groups, trifluoromethyl groups, sulfonyl groups, carbonyl groups and thiocarbonyl groups. 〔twenty three〕 A compound according to any one of

[16] to

[22] , wherein the molecular weight of the compound represented by the above formula (1) is 900 or less. [Effects of the Invention]

[0010] According to the present invention, a photoelectric conversion element can be provided that exhibits small variations in dark current and excellent photoelectric conversion efficiency. Furthermore, an image sensor, a photosensor, and a compound can also be provided. [Brief explanation of the drawing]

[0011] [Figure 1]This is a schematic cross-sectional diagram showing one example of a photoelectric conversion element configuration. [Figure 2] This is a schematic cross-sectional diagram showing one example of a photoelectric conversion element configuration. [Modes for carrying out the invention]

[0012] The photoelectric conversion element of the present invention will be described below. In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. In this specification, hydrogen atoms may be light hydrogen atoms and deuterium atoms (for example, dihydrogen atoms, etc.).

[0013] [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 that order, wherein the photoelectric conversion film contains a compound represented by formula (1) (hereinafter also referred to as the "specific compound"). The mechanism by which the desired effect is obtained with the configuration of the present invention is not clear, but the inventors speculate as follows: They speculate that a specific compound having both the group represented by A and the group represented by D has excellent properties such as crystallinity, resulting in less variation in dark current and excellent photoelectric conversion efficiency. Hereinafter, "the effects of the present invention are superior" refers to obtaining at least one of the following effects: smaller variation in dark current and superior photoelectric conversion efficiency.

[0014] Figure 1 shows a schematic cross-sectional view of one embodiment of the photoelectric conversion element of the present invention. The photoelectric conversion element 10a shown in Figure 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 that functions as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and a transparent conductive film (hereinafter also referred to as the "upper electrode") 15 that functions as an upper electrode are stacked in this order. Figure 2 shows an example of the configuration of another photoelectric conversion element. The photoelectric conversion element 10b shown in Figure 2 has a configuration in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are stacked on the lower electrode 11 in this order. Note that the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in Figures 1 and 2 may be changed as appropriate depending on the application and characteristics.

[0015] In the photoelectric conversion element 10a or 10b, it is preferable that light is incident on the photoelectric conversion film 12 via the upper electrode 15. Furthermore, when using the photoelectric conversion element 10a or 10b, a voltage can be applied. In this case, the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and between this pair of electrodes, 1 × 10 -5 ~1 × 10 7 It is preferable to apply a voltage of V / cm. From the viewpoint of performance and power consumption, the applied voltage should be 1 × 10⁻⁶. -4 ~1 × 10 7 V / cm is more preferable, 1 × 10 -3 ~5×10 6 V / cm is even more preferable. Regarding the voltage application method, it is preferable to apply the voltage so that the electron blocking film 16A side becomes the cathode and the photoelectric conversion film 12 side becomes the anode, as shown in Figures 1 and 2. The same method can be used to apply the voltage when the photoelectric conversion element 10a or 10b is used as a light sensor or when it is incorporated into an image sensor. As will be described in detail later, the photoelectric conversion element 10a or 10b can be suitably applied to image sensor applications. The configuration of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.

[0016] [Photoelectric conversion film] The photoelectric conversion element has a photoelectric conversion film.

[0017] <Specific compound> The photoelectric conversion film contains a specific compound as a photoelectric conversion material. In formula (1), R BIt includes geometric isomers that can be distinguished based on the C=C double bond composed of the carbon atom to which it is bonded and the carbon atom adjacent thereto. That is, both the cis isomer and the trans isomer distinguished based on the above C=C double bond are included in the compound represented by formula (1).

[0018] The specific compound is a compound represented by formula (1). A-D-A (1) In formula (1), A represents a group represented by formula (A-1). D represents a group represented by any one of formulas (2) to (4). Note that the two A's represent the same group.

[0019]

Chemical formula

[0020] In formula (A-1), * represents the bonding position. R B represents a hydrogen atom or an alkyl group that may have a substituent. C 1 contains two or more carbon atoms as ring member atoms and represents a ring group that may have a substituent. Z 1 represents an oxygen atom, a sulfur atom, =NR Z1 or =CR Z2 R Z3 represents. R Z1 represents a hydrogen atom or a substituent. R Z2 and R Z3 each independently represent a cyano group, -SO2R Z4 , -COOR Z5 or -COR Z6 represents. R Z4 ~R Z6 each independently represent an alkyl group that may have a substituent, an aryl group that may have a substituent or a heteroaryl group that may have a substituent.

[0021] R B represents a hydrogen atom or an alkyl group that may have a substituent. The above alkyl group may be linear, branched or cyclic, and a linear one is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, and more preferably 1 to 2. Examples of substituents that the alkyl group may have include substituent W. R B A hydrogen atom is preferred as the element.

[0022] C 1 This represents a ring group containing two or more carbon atoms as ring member atoms, and which may have substituents. C 1 As a ring member atom, Z in formula (A-1) 1 The carbon atom to which it is bonded, and R B It is a ring group that includes the carbon atom to which it is bonded and the carbon atoms adjacent to it. C 1 The ring may be monocyclic or polycyclic, and the polycyclic ring may be non-fused or fused. C 1 It may be either aromatic or non-aromatic. C 1 The total number of carbon atoms is preferably 2 to 30, and more preferably 5 to 15. Note that the total number of carbon atoms is Z in formula (A-1). 1 The carbon atom to which it is bonded, R B The carbon atoms adjacent to the carbon atom to which it is bonded, and C 1 This value includes the substituents that it may have. C 1 Preferably, the ring is a 5-membered ring, a 6-membered ring, or a fused ring combining these. The fused ring is preferably composed of 1 to 4 monorings, and more preferably composed of 1 to 3 monorings.

[0023] C 1 It may have heteroatoms. Examples of heteroatoms include halogen atoms, nitrogen atoms, sulfur atoms, oxygen atoms, selenium atoms, tellurium atoms, phosphorus atoms, silicon atoms, and boron atoms. Also, C 1 The heteroatoms that may be present may be either ring member atoms or non-ring member atoms (e.g., substituents). C 1The heteroatoms that can be present are preferably nitrogen atoms, sulfur atoms, or oxygen atoms, and more preferably nitrogen atoms or oxygen atoms. The nitrogen atom is -NR N - or -N= is preferred, and -N= is more preferred. N represents a hydrogen atom or substituent. C 1 The number of heteroatoms that may be present is preferably 0 to 10, more preferably 0 to 5, and even more preferably 1 to 4. C 1 If C has a heteroatom, 1 Preferably, the group contains a heteroatom. Preferred heteroatom-containing groups include -N=, a halogen atom, a cyano group, a trifluoromethyl group, a sulfonyl group, a carbonyl group, or a thiocarbonyl group.

[0024] C 1 The substituent may have substituents. Examples of substituents include substituent W, which is preferably a halogen atom, a cyano group, a trifluoromethyl group, an alkyl group, an aryl group, or a heteroaryl group, and more preferably a halogen atom, a cyano group, or a trifluoromethyl group. Furthermore, C has excellent photoelectric conversion efficiency. 1 It is also preferable that the substituent does not have a ring. In this case, the crystallinity of the specific compound may be improved. The ring may be either an aromatic ring or a non-aromatic ring. C 1 To say that a substituent does not have a ring means that some or all of the substituents do not have a ring. In other words, it does not have substituents with rings or ring groups. Specifically, C 1 It is preferable that the substituent does not contain aromatic rings such as benzyl, phenyl, and naphthyl groups. 1 It is permissible for the compound itself to be a ring group.

[0025] C 1 The rings that make up the rings are preferably those that are typically used as acid nuclei in merocyanine dyes. Specifically, the following (a) to (s) are examples. (a) 1,3-Dicarbonyl nuclei: Examples include 1,3-Indanedione nuclei, 1,3-Cyclohexanedione, 5,5-Dimethyl-1,3-Cyclohexanedione, and 1,3-Dioxane-4,6-dione. (b) Pyrazolinone nuclei: Examples include 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, and 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one. (c) Isoxazolinone nuclei: Examples include 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one. (d) Oxindole nuclei: For example, 1-alkyl-2,3-dihydro-2-oxyindole. (e) 2,4,6-trioxohexahydropyrimidine nuclei: For example, barbituric acid or 2-thiobarbituric acid and its derivatives. Examples of the above derivatives include 1-alkyl compounds such as 1-methyl and 1-ethyl, 1,3-dialkyl compounds such as 1,3-dimethyl, 1,3-diethyl and 1,3-dibutyl, 1,3-diaryl compounds such as 1,3-diphenyl, 1,3-di(p-chlorophenyl) and 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1-aryl compounds such as 1-ethyl-3-phenyl, and 1,3-diheteroaryl compounds such as 1,3-di(2-pyridyl). (f) 2-thio-2,4-thiazolidinedione core: For example, rhodanine and its derivatives. Examples of the above derivatives include 3-alkylrhodanines such as 3-methylrhodanine, 3-ethylrhodanine, and 3-allylrhodanine, 3-arylrhodanines such as 3-phenylrhodanine, and 3-heteroarylrhodanines such as 3-(2-pyridyl)rhodanine. (g) 2-thio-2,4-oxazolidinedione (2-thio-2,4-(3H,5H)-oxazoledione core: for example, 3-ethyl-2-thio-2,4-oxazolidinedione. (h) Thianaphthenone nucleus: For example, 3(2H)-thianaphthenone-1,1-dioxide is an example. (i) 2-thio-2,5-thiazolidinedione nuclei: For example, 3-ethyl-2-thio-2,5-thiazolidinedione is an example. (j) 2,4-thiazolidinedione nuclei: Examples include 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione. (k) Thiazolin-4-one nuclei: Examples include 4-thiazolinone and 2-ethyl-4-thiazolinone. (l) 2,4-Imidazolidinedione (hydantoin) nuclei: Examples include 2,4-Imidazolidinedione and 3-ethyl-2,4-Imidazolidinedione. (m) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nuclei: Examples include 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. (o) 3,5-pyrazolidinedione nuclei: Examples include 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione. (p) Benzothiophene-3(2H)-one nuclei: Examples include benzothiophene-3(2H)-one, oxobenzothiophene-3(2H)-one, and dioxobenzothiophene-3(2H)-one. (q) Indanone cores: Examples include 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone, and 3,3-dimethyl-1-indanone. (r) Benzofuran-3-(2H)-one nucleus: For example, benzofuran-3-(2H)-one is one such nucleus. (s)2,2-dihydrophenalene-1,3-dione nuclei are an example.

[0026] Z 1 This consists of an oxygen atom, a sulfur atom, and =NR Z1 or =CR Z2 R Z3represents R. Z1 R represents a hydrogen atom or a substituent. Z2 and R Z3 each independently represent a cyano group, -SO2R Z4 , -COOR Z5 or -COR Z6 represents R. Z4 ~R Z6 each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent or a heteroaryl group which may have a substituent. Z 1 is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom. R Z1 Examples of the substituent represented by R include the groups exemplified by the substituent W. R Z2 and R Z3 are preferably a cyano group. R Z4 ~R Z6 are preferably an alkyl group which may have a substituent. Z4 ~R Z6 Examples of the substituent that the alkyl group, aryl group and heteroaryl group represented by R may have include the groups exemplified by the substituent W.

[0027] As the group represented by the formula (A-1), the group represented by the formula (A-2) is preferable.

[0028]

Chemical formula

[0029] In the formula (A-2), R <00OO069>represents a hydrogen atom or an alkyl group which may have a substituent. 1 Z is an oxygen atom, a sulfur atom, =NR Z1 or =CR Z2 R Z3 represents R. Z1 R represents a hydrogen atom or a substituent. Z2 and R Z3 each independently represent a cyano group, -SO2RZ4 、 -COOR Z5 or -COR Z6 represents. R Z4 ~ R Z6 Each independently represents an alkyl group which may have a substituent, an aryl group which may have a substituent or a heteroaryl group which may have a substituent. Z represents a single bond, -CO-, -C(=CR Z21 R Z22 )-, -SO2-, -NR Z23 -, -S- or -CR Z24 = represents. R Z21 ~ R Z23 Each independently represents a cyano group or -COOR Z25 represents. R Z24 and R Z25 Each independently represents a hydrogen atom or a substituent. Y represents -CR Y1 =CR Y2 -, -N=CR Y3 -, -NR Y4 -CO-, -NR Y5 -CS- or =CR Y6 -CO- represents. R Y1 ~ R Y6 Each independently represents a hydrogen atom or a substituent. L represents a single bond or -NR L - represents. R L represents a hydrogen atom or a substituent.

[0030] In formula (A-2), R B and Z 1 are respectively synonymous with R B and Z 1 in formula (A-1), and the preferred embodiments are also the same.

[0031] Z represents a single bond, -CO-, -C(=CR Z21 R Z22 )-, -SO2-, -NR Z23 -, -S- or -CR Z24 = represents. R<​​​​​​​​​ For Z, -CO-, -C (=CR Z21 R Z22 )-, -SO2-, -NR Z23 - or -CR Z24 = is preferred, and -CO- is more preferred. R Z21 ~R Z23 A cyano group is preferred as the element. R Z24 and R Z25 Examples of substituents represented by include the group exemplified by substituent W, and preferably optionally substituted alkyl groups, optionally substituted aryl groups, or optionally substituted heteroaryl groups, with optionally substituted alkyl groups being more preferred. In addition, R is superior in terms of photoelectric conversion efficiency. Z24 and R Z25 The substituent represented by may preferably not have a ring as a substituent. In this case, the crystallinity of the specific compound may be improved. The significance of the substituent not having a ring is as described above. The alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1 to 10, and more preferably 1 to 3. The aryl group and the heteroaryl group may be monocyclic or polycyclic. The number of carbon atoms in the above aryl group and heteroaryl group is preferably 6 to 15, and more preferably 6 to 12. Examples of substituents that the alkyl group, aryl group, and heteroaryl group may have include the group exemplified by substituent W.

[0032] Y is -CR Y1 =CR Y2 -, -N=CR Y3 -, -NR Y4 -CO-, -NR Y5 -CS- or =CR Y6 R represents -CO-. Y1 ~R Y6 Each of these independently represents a hydrogen atom or a substituent. R Y1 ~RY6 The substituent represented is preferably an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent, and more preferably an alkyl group which may have a substituent. Also, R Y3 ~R Y5 As such, alkyl groups which may have substituents are preferred, and unsubstituted alkyl groups are more preferred. Also, in terms of excellent photoelectric conversion efficiency, R Y1 ~R Y6 The substituent represented by preferably does not have a ring group as a substituent. In this case, the crystallinity of the specific compound may be improved. The significance of the substituent not having a ring is as described above. The alkyl group, the aryl group and the heteroaryl group mentioned above are R Z24 and the above R Z25 Examples of substituents represented by include alkyl groups, aryl groups, and heteroaryl groups. Also, Y is -CR Y1 =CR Y2 When representing -, R Y1 and R Y2 It is preferable that the two combine to form a ring, R Y1 and R Y2 It is more preferable that the two elements bond to each other to form a benzene ring.

[0033] L is a single bond or -NR L - represents R L represents a hydrogen atom or substituent. R L Examples of substituents represented by include the group exemplified by substituent W, and preferably optionally substituted alkyl groups, optionally substituted aryl groups, or optionally substituted heteroaryl groups, more preferably optionally substituted alkyl groups, and preferably unsubstituted alkyl groups. In addition, R is superior in terms of photoelectric conversion efficiency. L The substituent represented by preferably does not have a ring group as a substituent. In this case, the crystallinity of the specific compound may be improved. The significance of the substituent not having a ring is as described above. The alkyl group, the aryl group and the heteroaryl group mentioned above are R Z4 and the above R Z5 Examples of substituents represented by include alkyl groups, aryl groups, and heteroaryl groups.

[0034] The preferred combinations of L, Y, and Z are those in which the ring formed by the bonding of -ZYL- with the two carbon atoms explicitly shown in formula (1) is a 5-membered ring or a 6-membered ring. Furthermore, as described above, the 5-membered ring or the 6-membered ring may be further fused with another ring (preferably a benzene ring) to form a fused ring.

[0035] The group represented by formula (A-1) is more preferably the group represented by formula (C-1) or the group represented by formula (C-2).

[0036] [ka]

[0037] In equation (C-1), * represents the bond position. B X represents an alkyl group which may have a hydrogen atom or substituents. c1 and X c2 These are, independently, an oxygen atom, a sulfur atom, and =NR. c11 or =CR c12 R c13 Represents R c11 R represents a hydrogen atom or substituent. c12 and R c13 These are, independently, a cyano group and a -SO2R group. c14 ,-COOR c15 or -COR c16 Represents R c14 ~R c16 Each of these independently represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. 3 This represents an aromatic ring containing at least two carbon atoms and which may have substituents. In equation (C-2), * represents the bond position.B X represents an alkyl group which may have a hydrogen atom or substituents. c3 ~X c5 These are, independently, an oxygen atom, a sulfur atom, and =NR. c21 or =CR c22 R c23 Represents R c21 R represents a hydrogen atom or substituent. c22 and R c23 These are, independently, a cyano group and a -SO2R group. c24 ,-COOR c25 or -COR c26 Represents R c24 ~R c26 Each of these independently represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. c1 and R c2 Each of these independently represents a hydrogen atom or a substituent.

[0038] In formula (C-1), R B These are R in equation (A-1), respectively. B This is synonymous with the same as the preferred embodiment. Also, in formula (C-1), X c1 and X c2 These are the Z in equation (A-1), respectively. 1 This is synonymous with the same thing, and the preferred embodiment is also the same. C 3 This represents an aromatic ring containing two or more carbon atoms, which may have substituents. The number of carbon atoms in the aromatic ring is preferably 5 to 30, more preferably 5 to 12, and even more preferably 6 to 8. Note that the above number of carbon atoms includes the two carbon atoms explicitly indicated in the formula. The above aromatic ring may be monocyclic or polycyclic. The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, with an aromatic hydrocarbon ring being preferred. The aromatic ring is preferably a benzene ring, a naphthalene ring, an anthracene ring, or a pyrene ring, with a benzene ring being more preferred. Examples of substituents that the aromatic ring may have include the group exemplified by substituent W.

[0039] In terms of having superior effects of the present invention, A preferably has a group containing an atom selected from nitrogen, oxygen, sulfur, and halogen atoms, more preferably -N=(preferably as a ring member atom), 1 to 5 atoms or groups selected from the group consisting of halogen atoms, cyano groups, trifluoromethyl groups, sulfonyl groups, carbonyl groups, and thiocarbonyl groups (hereinafter collectively referred to as "Y groups"), even more preferably 2 to 4 atoms or groups selected from the group consisting of Y groups, and particularly preferably 3 to 4 atoms or groups selected from the group consisting of Y groups.

[0040] D represents a base that can be expressed by any of the equations (2) to (4). D is preferably a group represented by formula (2) or formula (3).

[0041] [ka]

[0042] In equations (2) to (4), * indicates the bonding position. In formula (2), Ar 1 This represents a group represented by any of the formulas (7) to (10). Note that the two Ar 1 These represent the same base. In formula (3), Ar 2 and Ar 3 One of the two Ar groups represents a group represented by any of formulas (7) to (10), and the other represents a group represented by any of formulas (5) to (10). 3 represents the same group. Ar 2 and Ar 3 They may be the same or different. In formula (4), Ar 4 and Ar 5 One of the terms represents a group represented by any of formulas (7) to (10), and the other represents a group represented by either formula (5) or formula (6). Note that the two Ar 4 represents the same group, and the two Ar 5 These represent the same base.

[0043] Ar 1 The group represented by formula (10) is preferred. Ar 2 and Ar 3 Preferably, one of the elements represents a group represented by formula (10), and the other represents a group represented by either formula (5) or formula (10). Ar 4 and Ar 5 Preferably, one of the elements represents a group represented by formula (10), and the other represents a group represented by formula (5). In equation (3), one Ar 2 and two Ar 3 The total number of monorings is often 4 to 6, preferably 4 to 5, and more preferably 4. Specifically, one Ar 2 The represents a benzene ring, and the two Ar 3 If represents a naphthalene ring (which consists of two monocyclic benzene rings), then the total number of monocyclic rings in equation (3) is 5.

[0044] [ka]

[0045] In equations (5) to (10), * indicates the bonding position. The bonding direction of the groups represented by formulas (5) to (10) in a particular compound may be either the bonding direction shown above or the bonding direction opposite to that shown above. Specifically, the two Ar groups in formula (2) 1 When represents a group represented by formula (9), formula (2) may be either the group represented by formula (2A) or the group represented by formula (2B). The bonding direction is not limited to the following embodiments of formula (2A) and formula (2B).

[0046] [ka]

[0047] In formula (5), Y 51 ~Y 54 These are, independently, -CR A5= or represents a nitrogen atom. A5 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (6), X 61 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 61 and Y 62 These are, independently, -CR A6 = or represents a nitrogen atom. A6 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (7), Y 71 ~Y 76 These are, independently, -CR A7 = or represents a nitrogen atom. A7 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (8), X 81 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 81 ~Y 84 These are, independently, -CR A8 = or represents a nitrogen atom. A8 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (9), X 91 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 91 ~Y 94 These are, independently, -CR A9 = or represents a nitrogen atom. A9 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (10), X 101 and X 102 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 101 and Y 102 These are, independently, -CR A10 = or represents a nitrogen atom. A10 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group.

[0048] In formula (5), Y 51 ~Y 54 For example, -CR A5 = preferable. Y 51 ~Y 54 At least one of them is -CR A5 = represents R A5 Y preferably represents a halogen atom, a trifluoromethyl group, or a cyano group. 51 ~Y 54 One or two of them are -CR A5 = represents R A5 It is more preferable that represents a halogen atom, a trifluoromethyl group, or a cyano group. Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred. Multiple R A5 If R exists, A5 They may be the same or different.

[0049] In formula (6), X 61 As such, oxygen atoms or sulfur atoms are preferred. Y 61 and Y 62 One of them represents -CH=, and the other represents -CR A6 = or R represents a nitrogen atom A6 Preferably, represents a halogen atom, a trifluoromethyl group, or a cyano group. Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred. Multiple R A6 If R exists, A6 They may be the same or different.

[0050] In formula (7), Y 71 ~Y 76 These are, independently, -CR A7 = or represents a nitrogen atom. A7 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. Y 71 ~Y 76 For example, -CR A7 = is preferable. A7 It is preferable that this represents a hydrogen atom. Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred. Multiple R A7 If R exists, A7 They may be the same or different.

[0051] In formula (8), X 81 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 81 ~Y 84 These are, independently, -CR A8 = or represents a nitrogen atom. A8 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. X 81 The atom is preferably an oxygen atom or a sulfur atom, and more preferably a sulfur atom. Y 81 ~Y 84 It is preferable that -CH= or a nitrogen atom be represented by Y 81 ~Y 84 All of them represent -CH=, or Y 81 Y represents a nitrogen atom. 82 ~Y 84 It is more preferable that -CH= is represented. Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred. R A8 A hydrogen atom is preferred as the element. Multiple R A8 If R exists, A8 They may be the same or different.

[0052] In formula (9), X 91 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 91 ~Y 94 These are, independently, -CR A9 = or represents a nitrogen atom. A9 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. X 91The atom is preferably an oxygen atom or a sulfur atom, and more preferably a sulfur atom. Y 91 ~Y 94 It is preferable that -CH= or a nitrogen atom be represented by Y 91 ~Y 94 All of them represent -CH=, or Y 91 Y represents a nitrogen atom. 92 ~Y 94 It is more preferable that -CH= is represented. Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred. R A9 A hydrogen atom is preferred as the element. Multiple R A9 If R exists, A9 They may be the same or different.

[0053] In formula (10), X 101 and X 102 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 101 and Y 102 These are, independently, -CR A10 = or represents a nitrogen atom. A10 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. X 101 and X 102 The atom is preferably an oxygen atom or a sulfur atom, and more preferably a sulfur atom. Y 101 and Y 102 Preferably, -CH= or a nitrogen atom is preferred, and a nitrogen atom is more preferred. Examples of the halogen atoms mentioned above include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms or chlorine atoms being preferred. R A10 A hydrogen atom is preferred as the element. Multiple R A10 If R exists, A10 They may be the same or different.

[0054] It is preferable that D contains at least one ring selected from the group consisting of a furan ring, a thiophene ring, a thiazole ring, and an oxazole ring, and more preferably that D contains at least one ring selected from the group consisting of a thiophene ring and a thiazole ring. Another preferred embodiment of D is that it preferably contains at least one ring selected from the group consisting of a thiophene ring, a furan ring, and a thiazole ring, and more preferably contains at least one ring selected from the group consisting of a thiophene ring and a furan ring.

[0055] In terms of superior effects of the present invention, D preferably has at least two or four atoms or groups selected from the group consisting of -N=, halogen atoms, trifluoromethyl groups, and cyano groups (hereinafter collectively referred to as "X groups"), and more preferably has at least two atoms or groups selected from the group consisting of X groups.

[0056] The specific compound preferably includes a compound represented by any of formulas (11) to (38), more preferably a compound represented by any of formulas (11) to (13), formulas (17) to (19), formulas (23) to (26), and formulas (29) to (32) in terms of superior effects of the present invention, even more preferably a compound represented by any of formulas (11), (12), (17), (18), (23), (24), (29), and (30), and particularly preferably a compound represented by formula (11) or formula (12). As will be explained later, in equations (11) to (38), groups represented by the same notation represent the same group. The statement that groups represented by the same notation represent the same group means, for example, that X in the following equation... n (where n represents an integer greater than or equal to 1.) Multiple X with the same n n This means they are the same group. Specifically, in equation (11), the two X 111 represents the same group, and the two Y 111 These represent the same group, and the two A 11 represents the same group, and the two Z 11 This means that they represent the same group. However, if multiple R's are present in the same formula, An If (n represents an integer greater than or equal to 1), then multiple R An They may be the same or different.

[0057] The group represented by formula (5), the group represented by formula (6), and the group represented by formula (A-1) that a compound represented by any of formulas (11) to (38) may have are the same as the groups that a specific compound may have, and the preferred embodiments are also the same.

[0058] [ka]

[0059] [ka]

[0060] In formula (11), X 111 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 111 -CR A11 = or represents a nitrogen atom. A11 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 11 This represents the group represented by formula (5) or the group represented by formula (6). 11 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A11 They may be the same or different. In formula (12), X 121 and X 122 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 121 and Y 122 These are, independently, -CR A12 = or represents a nitrogen atom. A12 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 12 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A12 They may be the same or different. In formula (13), X 131 and X 132 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 131 and Y 132 These are, independently, -CR A13 = or represents a nitrogen atom. A13 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 13 This represents the group represented by formula (5) or the group represented by formula (6). 13 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A13 They may be the same or different. In formula (14), X 141 and X 142 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 141 and Y 142 These are, independently, -CR A14 = or represents a nitrogen atom. A14 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 14 This represents the group represented by formula (5) or the group represented by formula (6). 14 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A14 They may be the same or different. In formula (15), X 151 ~X 153 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 151 ~Y 153 These are, independently, -CR A15 = or represents a nitrogen atom. A15 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 15 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A15 They may be the same or different. In formula (16), X 161 and X 162Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 161 ~Y 165 These are, independently, -CR A16 = or represents a nitrogen atom. A16 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 16 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A16 They may be the same or different. In formula (17), Y 171 ~Y 173 These are, independently, -CR A17 = or represents a nitrogen atom. A17 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 17 This represents the group represented by formula (5) or the group represented by formula (6). 17 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A17 They may be the same or different. In formula (18), Y 181 ~Y 186 These are, independently, -CR A18 = or represents a nitrogen atom. A18 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 18 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A18 They may be the same or different. In formula (19), Y 191 ~Y 196 These are, independently, -CR A19 = or represents a nitrogen atom. A19 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 19 This represents the group represented by formula (5) or the group represented by formula (6). 19 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A19 They may be the same or different. In formula (20), Y 201 ~Y 206 These are, independently, -CR A20 = or represents a nitrogen atom. A20 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 20 This represents the group represented by formula (5) or the group represented by formula (6). 20 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A20 They may be the same or different. In formula (21), Y 211 ~Y 219 These are, independently, -CR A21 = or represents a nitrogen atom. A21 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 21 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A21 They may be the same or different. In formula (22), X 221 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 221 ~Y 226 These are, independently, -CR A22 = or represents a nitrogen atom. A22 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 22 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A22 They may be the same or different. In formula (23), X 231 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 231 ~Y 234 These are, independently, -CR A23 = or represents a nitrogen atom. A23 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 23 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A23 They may be the same or different. In formula (24), X 241 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 241 ~Y 244 These are, independently, -CR A24 = or represents a nitrogen atom. A24 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 24 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A24 They may be the same or different. In formula (25), X 251 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 251 ~Y 254 These are, independently, -CR A25 = or represents a nitrogen atom. A25 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 25 This represents the group represented by formula (5) or the group represented by formula (6). 25 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A25 They may be the same or different. In formula (26), X 261 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 261 ~Y 264 These are, independently, -CR A26 = or represents a nitrogen atom. A26 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 26 This represents the group represented by formula (5) or the group represented by formula (6). 26 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A26 They may be the same or different. In formula (27), X 271 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 271 ~Y 274 These are, independently, -CR A27 = or represents a nitrogen atom. A27Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 27 This represents the group represented by formula (5) or the group represented by formula (6). 27 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A27 They may be the same or different. In formula (28), X 281 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 281 ~Y 284 These are, independently, -CR A28 = or represents a nitrogen atom. A28 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 28 This represents the group represented by formula (5) or the group represented by formula (6). 28 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A28 They may be the same or different. In formula (29), X 291 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 291 ~Y 294 These are, independently, -CR A29 = or represents a nitrogen atom. A29 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 29 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A29 They may be the same or different. In formula (30), X 301 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 301 ~Y 304 These are, independently, -CR A30 = or represents a nitrogen atom. A30 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 30 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A30 They may be the same or different. In formula (31), X 311 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 311 ~Y 314 These are, independently, -CR A31 = or represents a nitrogen atom. A31 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 31 This represents the group represented by formula (5) or the group represented by formula (6). 31 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A31 They may be the same or different. In formula (32), X 321 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 321 ~Y 324 These are, independently, -CR A32 = or represents a nitrogen atom. A32 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 32 This represents the group represented by formula (5) or the group represented by formula (6). 32 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A32 They may be the same or different. In formula (33), X 331 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 331 ~Y 334 These are, independently, -CR A33 = or represents a nitrogen atom. A33 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 33 This represents the group represented by formula (5) or the group represented by formula (6). 33 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A33 They may be the same or different. In formula (34), X 341 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 341 ~Y 344 These are, independently, -CRA34 = or represents a nitrogen atom. A34 Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 34 This represents the group represented by formula (5) or the group represented by formula (6). 34 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A34 They may be the same or different. In formula (35), X 351 and X 352 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 351 ~Y 355 These are, independently, -CR A35 = or represents a nitrogen atom. A35 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 35 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A35 They may be the same or different. In formula (36), X 361 and X 362 Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. 361 ~Y 365 These are, independently, -CR A36 = or represents a nitrogen atom. A36 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 36 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A36 They may be the same or different. In formula (37), X 371 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 371 ~Y 377 These are, independently, -CR A37 = or represents a nitrogen atom. A37 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 37 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, RA37 They may be the same or different. In formula (38), X 381 Y represents an oxygen atom, a sulfur atom, or a selenium atom. 381 ~Y 387 These are, independently, -CR A38 = or represents a nitrogen atom. A38 A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. 38 This represents the group represented by formula (A-1). Note that groups represented by the same notation represent the same group. However, R A38 They may be the same or different.

[0061] In formula (11), X 111 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 111 As for Y in equation (10), 101 or Y 102 A base represented by is preferred. Z 11 As such, the group represented by formula (5) described above is preferred.

[0062] In formula (12), X 121 and X 122 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 121 and Y 122 As for Y in equation (10), 101 or Y 102 A base represented by is preferred.

[0063] In formula (13), X 131 and X 132 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 131 and Y 132 As for Y in equation (10), 101 or Y 102 A base represented by is preferred. Z 13 As such, the group represented by formula (5) described above is preferred.

[0064] In formula (14), X 141 and X 142 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 141 and Y 142 As for Y in equation (10), 101 or Y 102 It is preferable. Z 14 As such, the group represented by formula (5) described above is preferred.

[0065] In formula (15), X 151 ~X 153 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 151 ~Y 153 As for Y in equation (10), 101 or Y 102 A base represented by is preferred.

[0066] In formula (16), X 161 and X 162 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 161 and Y 162 As for Y in equation (10), 101 or Y 102 A base represented by is preferred. Y 163 ~Y 165 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0067] In formula (17), Y 171 ~Y 173 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred. Z17 As such, the group represented by formula (5) described above is preferred.

[0068] In formula (18), Y 181 ~Y 186 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0069] In formula (19), Y 191 ~Y 196 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred. Z 19 As such, the group represented by formula (5) described above is preferred.

[0070] In formula (20), Y 201 ~Y 206 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0071] In formula (21), Y 211 ~Y 219 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0072] In formula (22), X 221 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 227 As for Y in equation (10), 101 or Y 102 A base represented by is preferred. Y 221 ~Y 226 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0073] In formula (23), X 231 For example, X in equation (8) 81 A base represented by is preferred. Y231 ~Y 234 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred.

[0074] In formula (24), X 241 For example, X in equation (9) 91 A base represented by is preferred. Y 241 ~Y 244 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred.

[0075] In formula (25), X 251 For example, X in equation (8) 81 A base represented by is preferred. Y 251 ~Y 254 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Z 25 As such, the group represented by formula (5) described above is preferred.

[0076] In formula (26), X 261 For example, X in equation (9) 91 A base represented by is preferred. Y 261 ~Y 264 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred. Z 26 As such, the group represented by formula (5) described above is preferred.

[0077] In formula (27), X 271 For example, X in equation (8) 81 A base represented by is preferred. Y 271 ~Y 274 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Z 27 As such, the group represented by formula (5) described above is preferred.

[0078] In formula (28), X 281 For example, X in equation (9) 91 A base represented by is preferred. Y 281 ~Y 284 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred. Z 28 As such, the group represented by formula (5) described above is preferred.

[0079] In formula (29), X 291 For example, X in equation (9) 91 A base represented by is preferred. Y 291 ~Y 294 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred.

[0080] In formula (30), X 301 For example, X in equation (8) 81 A base represented by is preferred. Y 301 ~Y 304 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred.

[0081] In formula (31), X 311 For example, X in equation (9) 91 A base represented by is preferred. Y 311 ~Y 314 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred. Z 31 As such, the group represented by formula (5) described above is preferred.

[0082] In formula (32), X 321 For example, X in equation (8) 81 A base represented by is preferred. Y 321 ~Y324 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Z 32 As such, the group represented by formula (5) described above is preferred.

[0083] In formula (33), X 331 For example, X in equation (9) 91 A base represented by is preferred. Y 331 ~Y 334 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred. Z 33 As such, the group represented by formula (5) described above is preferred.

[0084] In formula (34), X 341 For example, X in equation (8) 81 A base represented by is preferred. Y 341 ~Y 344 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Z 34 As such, the group represented by formula (5) described above is preferred.

[0085] In formula (35), X 351 For example, X in equation (8) 81 A base represented by is preferred. X 352 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 351 ~Y 354 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Y 355 As for Y in equation (10), 101 or Y 102 A base represented by is preferred.

[0086] In formula (36), X361 For example, X in equation (8) 81 A base represented by is preferred. X 362 For example, X in equation (10) 101 or X 102 A base represented by is preferred. Y 361 ~Y 364 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Y 365 As for Y in equation (10), 101 or Y 102 A base represented by is preferred.

[0087] In formula (37), X 371 For example, X in equation (8) 81 A base represented by is preferred. Y 371 ~Y 374 As for Y in equation (8), 81 ~Y 84 A base represented by is preferred. Y 375 ~Y 377 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0088] In formula (38), X 381 For example, X in equation (9) 91 A base represented by is preferred. Y 381 ~Y 384 As for Y in equation (9), 91 ~Y 94 A base represented by is preferred. Y 385 ~Y 387 As for Y in equation (7), 71 ~Y 76 A base represented by is preferred.

[0089] -Substituent W- Examples of substituents W include halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, etc.), alkyl groups, alkenyl groups (including cycloalkenyl and bicycloalkenyl groups), alkynyl groups, aryl groups, heterocyclic groups (including heteroaryl groups), cyano groups, hydroxyl groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy groups, aryloxycarbonyloxy groups, amino groups (including anilino groups), ammonia groups, acylamino groups, aminocarbonylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfamoylamino groups, and aryl groups. Examples include carboxyl or arylsulfonylamino groups, mercapto groups, alkylthio groups, arylthio groups, heterocyclic thio groups, sulfamoyl groups, alkyl or arylsulfinyl groups, alkyl or arylsulfonyl groups, acyl groups, aryloxycarbonyl groups, alkoxycarbonyl groups, carbamoyl groups, aryl or heterocyclic azo groups, imide groups, phosphino groups, phosphinyl groups, phosphinyloxy groups, phosphinylamino groups, phosphono groups, silyl groups, hydrazino groups, ureido groups, boronic acid groups (-B(OH)2), sulfo groups, carboxylic acid groups, phosphate groups, phosphonyl groups, phosphoryl groups, monosulfate ester groups, monophosphate ester groups, phosphonic acid groups, phosphinic acid groups, and boric acid groups. The substituent W may be further substituted with another substituent W. For example, if the substituent W is an alkyl group, it may be further substituted with a halogen atom, resulting in an alkyl group having a halogen atom. Examples of substituent W include the substituent W described in paragraph

[0023] of Japanese Patent Application Publication No. 2007-234651, the details of which are incorporated herein by reference.

[0090] The alkyl group, aryl group, and heteroaryl group that the specific compound may have may be any of alkyl group X, aryl group X, and heteroaryl group X, respectively.

[0091] -alkyl group X- The number of carbon atoms in alkyl group X is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 6. The alkyl group X may be linear, branched, or cyclic. Examples of alkyl groups X include methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, n-hexyl, and cyclopentyl groups. Furthermore, alkyl group X may be, for example, a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have these cyclic structures as substructures. Examples of substituents that alkyl group X may have include the groups exemplified by substituent W, and are preferably aryl groups (preferably having 6 to 18 carbon atoms, more preferably 6 carbon atoms), heteroaryl groups (preferably having 5 to 18 carbon atoms, more preferably 5 to 6 carbon atoms), or halogen atoms (preferably fluorine atoms or chlorine atoms).

[0092] -Aryl group X- The aryl group X preferably has 6 to 18 carbon atoms. The aryl group X may be monocyclic or polycyclic. The aryl group X is preferably a phenyl group, a naphthyl group, anthryl group, or a fluorenyl group, with the phenyl group being more preferred. Examples of substituents that the aryl group X may have include the groups exemplified by substituent W, with alkyl groups (preferably having 1 to 10 carbon atoms) being preferred, and methyl groups or i-propyl groups being more preferred.

[0093] The heteroatom of the heteroaryl group X is preferably a sulfur atom, an oxygen atom, or a nitrogen atom. The heteroaryl group X may be monocyclic or polycyclic. The number of carbon atoms in the heteroaryl group X is preferably 3 to 18, and more preferably 3 to 5. The number of heteroatoms in the heteroaryl group X is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 to 2. The number of ring members of the heteroaryl group X is preferably 3 to 8, more preferably 5 to 7, and even more preferably 5 to 6. Examples of heteroaryl groups X include furyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenantridinyl, pteridinyl, pyrazinyl, quinoxalinyl, pyrimidinyl, quinazolyl, pyridadinyl, sinnolinyl, phthalazinyl, triazinyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, pyrazolyl, indazolyl, isoxazolyl, benzoisoxazolyl, isothiazolyl, benzoisothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, benzofuryl, thienyl, benzothienyl, dibenzofuryl, dibenzothienyl, pyrrolyl, indolyl, imidazopyridinyl, and carbazolyl groups. Examples of substituents that the heteroaryl group X may have include the group exemplified by substituent W, with alkyl groups or aryl groups being preferred.

[0094] Regarding the molecular shape of the specific compound, it is preferable that the structure of D is linear and the structure of A is planar, in order to improve the crystallinity of the specific compound and to have superior photoelectric conversion efficiency. Specifically, a molecular shape in which the structure of D is linear and the structure of A is planar includes specific compounds that satisfy the following requirements A and B. Requirement A: In formula (A-1), R B and R Z1 ~R Z3 It does not have an aromatic ring group or an alicyclic group, C 1 It does not have aromatic ring groups or alicyclic groups as substituents. 1 It is permissible for the group itself to be an aromatic ring group or an alicyclic group. Requirement B: In formulas (2) to (4), Ar 1 ~Ar 5 However, it represents the group represented by formula (5) or the group represented by formula (10). The specified compounds mentioned above are preferably those represented by any of formulas (11) to (15). However, Z 11 , Z 13 and Z 14 represents the base expressed by formula (5), and A 11 ~A 15 This applies only if requirement A is met.

[0095] Examples of specific compounds include those combining D and A as follows: The following are specific examples for D. In the formulas, * indicates a bonding position.

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] The following are specific examples for A. In the formulas, * indicates a bonding position.

[0100] [ka]

[0101] [ka]

[0102] The molecular weight of the specific compound is not particularly limited, but is preferably 200 or higher, and more preferably 400 or higher. The upper limit is preferably 2000 or less, more preferably 1200 or less, and even more preferably 900 or less. If the molecular weight is 900 or less, the deposition temperature will not be high, and the decomposition of the compound will not occur easily. If the molecular weight is 400 or higher, the glass transition temperature of the deposited film will not be low, and the heat resistance of the photoelectric conversion element will be improved.

[0103] In terms of stability when used as a p-type organic semiconductor and energy level matching with an n-type organic semiconductor, the absolute value of the ionization potential of the specific compound as a single film is preferably 5.0 to 6.4 eV, more preferably 5.5 to 6.2 eV, and even more preferably 5.7 to 6.0 eV.

[0104] The maximum absorption wavelength of a particular compound is preferably in the range of 400 to 700 nm, more preferably in the range of 450 to 650 nm, and even more preferably in the range of 450 to 600 nm. The maximum absorption wavelengths mentioned above are values ​​measured in solution (solvent: chloroform) after adjusting the concentration of the specific compound to such an absorbance that it reaches 0.5 to 1.0. However, if the specific compound does not dissolve in chloroform, the maximum absorption wavelength of the specific compound is measured using a film-like substance obtained by vapor deposition of the specific compound.

[0105] Certain compounds may be purified as needed. The method for purifying the specific compound is not particularly limited, but sublimation purification is preferred.

[0106] The specific compounds may be used individually or in combination of two or more. The content of the specific compound in the photoelectric conversion film (= (film thickness of the specific compound on a single-layer basis) / (film thickness of the photoelectric conversion film) × 100) is preferably 15 to 75 volume%, more preferably 20 to 60 volume%, and even more preferably 25 to 50 volume%.

[0107] The specific compound is particularly useful as a material for a photoelectric conversion film used in an imaging device, a photosensor, or a photovoltaic cell. Note that the specific compound often functions as a dye in the photoelectric conversion film. Further, 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 agent material.

[0108] <n-type organic semiconductor> Preferably, the photoelectric conversion film contains an n-type organic semiconductor in addition to the above specific compound. The n-type organic semiconductor is a compound different from the above specific compound. The n-type organic semiconductor is an acceptor-type organic semiconductor material (compound), which refers to an organic compound having a property of easily accepting electrons. That is, the n-type organic semiconductor refers to the organic compound having a larger electron affinity when two organic compounds are used in contact with each other. That is, as the acceptor-type organic semiconductor, any organic compound can be used as long as it is an electron-accepting organic compound.

[0109] Examples of n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and their derivatives, condensed aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluorantene derivatives); and heterocyclic compounds of 5-7 membered rings having at least one atom selected from the group consisting of nitrogen, oxygen, and sulfur atoms (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazine Examples include zoles, imidazoles and thiazoles, etc.; polyarylene compounds; fluorene compounds; cyclopentadiene compounds; silyl compounds; 1,4,5,8-naphthalenetetracarboxylic anhydride; 1,4,5,8-naphthalenetetracarboxylic anhydride imide derivatives and oxadiazole derivatives; anthraquinodimethane derivatives; diphenylquinone derivatives; basocuproine, basophenanthroline and their derivatives; triazole compounds; distylyl arylene derivatives; metal complexes having nitrogen-containing heterocyclic compounds as ligands; silole compounds; and compounds described in paragraphs

[0056] to

[0057] of Japanese Patent Application Publication No. 2006-100767.

[0110] 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 obtained by adding substituents to the above-mentioned fullerene. Preferred substituents are alkyl groups, aryl groups, or heterocyclic groups. As fullerene derivatives, compounds described in Japanese Patent Application Publication No. 2007-123707 are preferred.

[0111] Organic dyes may be used as the n-type organic semiconductor. Examples of organic pigments include cyanine pigments, styryl pigments, hemicyanine pigments, merocyanine pigments (including zeromethine merocyanine (simple merocyanine)), rhodacyanine pigments, allopolar pigments, oxonol pigments, hemioxonol pigments, squalium pigments, croconium pigments, azametine pigments, coumarin pigments, allylidene pigments, anthraquinone pigments, triphenylmethane pigments, azo pigments, azomethine pigments, metallocene pigments, fluorenone pigments, fulgide pigments, perylene pigments, phenazine pigments, phenothiazine pigments, quinone pigments, diphenylmethane pigments, polyene pigments, acridine pigments, acridinone pigments, diphenylamine pigments, quinophthalone pigments, phenoxazine pigments, phthaloperylene pigments, dioxane pigments, porphyrin pigments, chlorophyll pigments, phthalocyanine pigments, subphthalocyanine pigments, and metal complex pigments.

[0112] The molecular weight of the n-type organic semiconductor is preferably 200 to 1200, and more preferably 200 to 900.

[0113] The maximum absorption wavelength of the n-type organic semiconductor is preferably in the range of 400 to 650 nm, more preferably in the range of 420 to 550 nm, and even more preferably in the range of 450 to 500 nm. The maximum absorption wavelength can be measured using the method for measuring the maximum absorption wavelength of the specified compound mentioned above.

[0114] The photoelectric conversion film preferably has a bulk heterostructure formed in a mixed state of a specific compound and an n-type organic semiconductor. The bulk heterostructure is a layer in the photoelectric conversion film in which the specific compound and the n-type organic semiconductor are mixed and dispersed. The photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. The bulk heterostructure is described in detail in paragraphs

[0013] to

[0014] of Japanese Patent Application Publication No. 2005-303266.

[0115] The difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or greater.

[0116] The n-type organic semiconductor may be used alone or in combination of two or more. In terms of the responsivity of the photoelectric conversion element, the content of the specific compound with respect to the total content of the specific compound and the n-type organic semiconductor (film thickness in terms of a single layer of the specific compound / (film thickness in terms of a single layer of the specific compound + film thickness in terms of a single layer of the n-type organic semiconductor) × 100) is preferably 20 to 80% by volume, more preferably 40 to 80% by volume. Further, when the photoelectric conversion film further contains a p-type organic semiconductor described later, the content of the specific compound (film thickness in terms of a single layer of the specific compound / (film thickness in terms of a single layer of the specific compound + film thickness in terms of a single layer of the n-type organic semiconductor + film thickness in terms of a single layer of the p-type organic semiconductor) × 100) is preferably 15 to 75% by volume, more preferably 35 to 75% by volume. Note that the photoelectric conversion film is preferably substantially composed of the specific compound, the n-type organic semiconductor, and, if necessary, the p-type organic semiconductor. "Substantially" means that the total content of the specific compound, the n-type organic semiconductor, and the p-type organic semiconductor is 95% by mass or more with respect to the total mass of the photoelectric conversion film. The upper limit is often 100% by mass or less.

[0117] <p-type organic semiconductor> The photoelectric conversion film preferably contains a p-type organic semiconductor in addition to the above specific compound. Also, the photoelectric conversion film preferably contains the specific compound, the n-type organic semiconductor, and the p-type organic semiconductor. The p-type organic semiconductor is a compound different from the above specific compound. The p-type organic semiconductor is a donor-type organic semiconductor material (compound), which refers to an organic compound having a property of easily donating electrons. That is, the p-type organic semiconductor refers to the organic compound with a smaller ionization potential when two organic compounds are brought into contact and used.

[0118] Examples of p-type organic semiconductors include triarylamine compounds (for example, N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), compounds described in paragraphs

[0128] to

[0148] of Japanese Patent Publication No. 2011-228614, compounds described in paragraphs

[0052] to

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

[0052] to

[0063] of Japanese Patent Publication No. 2011-225544)

[0119] Compounds described in

[0158] , compounds described in paragraphs

[0044] to

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

[0086] to

[0090] of Japanese Patent Publication No. 2012-94660, etc.), pyrazoline compounds, styrylamine compounds, hydrazone compounds, polysilane compounds, thiophene compounds (for example, thienothiophene derivatives, dibenzothiophene derivatives, benzodithiophene derivatives, dithienothiophene derivatives, [1]benzothieno[3,2-b]thiophene (BTBT) derivatives, thieno[3,2-f:4,5-f']thiophene [1]Benzothiophene (TBBT) derivatives, compounds described in paragraphs

[0031] to

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

[0043] to

[0045] of WO2016-194630, compounds described in paragraphs

[0025] to

[0037] and

[0099] to

[0109] of WO2017-159684, compounds described in paragraphs

[0029] to

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

[0015] to

[0025] of WO2018-207722, and in paragraph

[00] of JP 2019-054228. Compounds described in paragraphs

[45] to

[0053] of WO2019-058995, compounds described in paragraphs

[0045] to

[0055] of WO2019-081416, compounds described in paragraphs

[0063] to

[0089] of JP 2019-80052, compounds described in paragraphs

[0033] to

[0036] of WO2019-054125, compounds described in paragraphs

[0044] to

[0054] of WO2019-093188, etc., compounds described in paragraphs

[0034] to

[0037] of JP 2019-050398, JP 201 Compounds from paragraphs

[0033] to

[0036] of Japanese Patent Publication No. 8-206878, compound from paragraph

[0038] of Japanese Patent Application Publication No. 2018-190755, compound from paragraphs

[0019] to

[0021] of Japanese Patent Application Publication No. 2018-026559, compound from paragraphs

[0031] to

[0056] of Japanese Patent Application Publication No. 2018-170487, compound from paragraphs

[0036] to

[0041] of Japanese Patent Application Publication No. 2018-078270, compound from paragraphs

[0055] to

[0082] of Japanese Patent Application Publication No. 2018-166200, compound from paragraphs

[0041] to

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

[0044] to

[0048] of JP 2018-85430, compounds described in paragraphs

[0041] to

[0045] of JP 2018-056546, compounds described in paragraphs

[0042] to

[0049] of JP 2018-046267, compounds described in paragraphs

[0031] to

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

[0036] to

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

[0045] to

[0048] of JP 2020-010024, etc., cyanine compounds, oxonol compounds, polyamine compounds, indole compounds, pyrrole compounds Examples include metal compounds having nitrogen-containing heterocyclic compounds as ligands, pyrazole compounds, polyarylene compounds, condensed aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives, and fluorantene derivatives, etc.), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyarylalkane compounds, pyrazolone compounds, aminosubstituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having nitrogen-containing heterocyclic compounds as ligands. Examples of p-type organic semiconductors include compounds with a lower ionization potential than n-type organic semiconductors. If this condition is met, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of p-type organic semiconductors include the following compounds.

[0119] [ka]

[0120] [ka]

[0121] [ka]

[0122] [ka]

[0123] The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or greater.

[0124] When the photoelectric conversion film contains a p-type organic semiconductor, the p-type organic semiconductor content in the photoelectric conversion film (= film thickness of the p-type organic semiconductor on a single-layer basis / film thickness of the photoelectric conversion film × 100) is preferably 15 to 75 volume%, more preferably 20 to 60 volume%, and even more preferably 25 to 50 volume%. Furthermore, p-type organic semiconductors may be used individually or in combination of two or more types.

[0125] Photoelectric conversion films containing specific compounds are non-luminescent films and have characteristics different from organic light-emitting diodes (OLEDs). A non-luminescent film is defined as a film with a light emission quantum efficiency of 1% or less, preferably 0.5% or less, and more preferably 0.1% or less. The lower limit is often 0% or higher.

[0126] The maximum absorption wavelength of the photoelectric conversion film is preferably in the range of 500 to 600 nm, more preferably in the range of 520 to 580 nm, and even more preferably in the range of 530 to 565 nm. Another preferred embodiment of the maximum absorption wavelength of the photoelectric conversion film is preferably in the range of 440 to 600 nm, more preferably in the range of 440 to 580 nm, and even more preferably in the range of 440 to 565 nm. The maximum absorption wavelength can be measured using the method for measuring the maximum absorption wavelength of the specified compound mentioned above.

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

[0128] The film thickness of the photoelectric conversion film is preferably 10 to 1000 nm, more preferably 50 to 800 nm, even more preferably 50 to 500 nm, and particularly preferably 50 to 300 nm.

[0129] [electrode] The photoelectric conversion element preferably has electrodes. The electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of conductive material. Examples of conductive material include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident from the upper electrode 15, it is preferable that the upper electrode 15 be transparent to the light to be detected. Examples of materials that make up the upper electrode 15 include conductive metal oxides such as antimony or fluorine-doped tin oxide (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: Indium zinc oxide); thin metal films such as gold, silver, chromium, and nickel; mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole. Conductive metal oxides are preferred from the viewpoint of high conductivity and transparency.

[0130] Typically, when a conductive film is made thinner than a certain range, its resistance often increases sharply. In the solid-state image sensor incorporating the photoelectric conversion element according to this embodiment, the sheet resistance may be 100 to 10000 Ω / □, and there is a great degree of freedom in the range of film thickness that can be thinned. Furthermore, the thinner the upper electrode (transparent conductive film) 15, the less light it absorbs, and generally the light transmittance increases. An increase in light transmittance is desirable because it increases light absorption in the photoelectric conversion film and increases the photoelectric conversion capacity. Considering the suppression of leakage current, the increase in the resistance of the thin film, and the increase in transmittance associated with thinning, the thickness of the upper electrode 15 is preferably 5 to 100 nm, and more preferably 5 to 20 nm.

[0131] The lower electrode 11 may be made transparent or opaque to reflect light, depending on the application. Examples of materials that make up the lower electrode 11 include conductive metal oxides such as tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide (IZO); metals such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole.

[0132] The method for forming electrodes can be appropriately selected depending on the electrode material. Specifically, these 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, methods include electron beam method, sputtering method, resistance heating deposition method, chemical reaction method (sol-gel method, etc.), and coating of indium tin oxide dispersion.

[0133] [Charge-blocking films: electron-blocking films, hole-blocking films] The photoelectric conversion element preferably has one or more intermediate layers between the conductive film and the transparent conductive film, in addition to the photoelectric conversion film. Examples of the above-mentioned intermediate layer include charge-blocking films. If a photoelectric conversion element has this film, the characteristics of the resulting photoelectric conversion element (such as photoelectric conversion efficiency and responsiveness) will be improved. Examples of charge-blocking films include electron-blocking films and hole-blocking films.

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

[0135] Furthermore, the electron blocking film may be composed of multiple films. The electron blocking film may be composed of inorganic materials. Generally, inorganic materials have a higher dielectric constant than organic materials, so when inorganic materials are used for the electron blocking film, a higher voltage is applied to the photoelectric conversion film, resulting in higher photoelectric conversion efficiency. Examples of inorganic materials that can be used as electron blocking films include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, indium copper oxide, indium silver oxide, and iridium oxide.

[0136] <Hole blocking membrane> The hole-blocking film is an acceptor-type organic semiconductor material (compound), and the above-mentioned n-type organic semiconductor can be used. The hole-blocking film may be composed of multiple films.

[0137] Examples of methods for manufacturing charge-blocking films include dry deposition and wet deposition. Examples of dry deposition methods include vapor deposition and sputtering. Vapor deposition can be either physical vapor deposition (PVD) or chemical vapor deposition (CVD), with physical vapor deposition methods such as vacuum deposition being preferred. Examples of wet deposition methods include inkjet, spray, nozzle printing, spin coating, dip coating, casting, die coating, roll coating, bar coating, and gravure coating, with inkjet being preferred from the viewpoint of high-precision patterning.

[0138] The thickness of the charge blocking film (electron blocking film and hole blocking film) is preferably 3 to 200 nm, more preferably 5 to 100 nm, and even more preferably 5 to 30 nm, respectively.

[0139] <Circuit board> The photoelectric conversion element may further have a substrate. Examples of substrates include semiconductor substrates, glass substrates, and plastic substrates. The position of the substrate is not particularly restricted, but typically, the conductive film, photoelectric conversion film, and transparent conductive film are laminated on the substrate in this order.

[0140] <Sealing layer> The photoelectric conversion element may further have a sealing layer. Photoelectric conversion materials can experience significant performance degradation due to the presence of degradation factors such as water molecules. Therefore, this degradation can be prevented by covering and sealing the entire photoelectric conversion film with a dense sealing layer made of ceramics such as metal oxides, metal nitrides, or metal nitride oxides, or diamond-like carbon (DLC), which prevents the penetration of water molecules. Examples of sealing layers include those described in paragraphs

[0210] to

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

[0141] [Image sensor] One example of an application for photoelectric conversion elements is an image sensor. An image sensor is a device that converts the optical information of an image into electrical signals. Typically, multiple photoelectric conversion elements are arranged in a matrix on the same plane, and each photoelectric conversion element (pixel) converts the optical signal into an electrical signal, which can then be output sequentially to the outside of the image sensor for each pixel. For this purpose, each pixel consists of one or more photoelectric conversion elements and one or more transistors.

[0142] [Light sensor] Other applications of the photoelectric conversion element include, for example, photocells and optical sensors, and the photoelectric conversion element of the present invention is preferably used as an optical sensor. As an optical sensor, the photoelectric conversion element may be used alone, or it may be used as a line sensor in which the photoelectric conversion elements are arranged in a straight line, or as a two-dimensional sensor arranged on a plane.

[0143] [Compound] This invention also includes inventions relating to specific compounds. [Examples]

[0144] The present invention will be described in more detail below based on examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate, as long as they do not depart from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the examples shown below.

[0145] [Compounds to be evaluated] Compound (B-1) was synthesized according to the following scheme.

[0146] [ka]

[0147] Compound (1-1-1) (5 mmol), compound (1-1-2) (12 mmol), and toluene (50 mL) were placed in a glass reaction vessel. Pd(PPh3)4 (0.25 mmol) was then added under a nitrogen atmosphere, and the reaction was carried out at 100°C for 4 hours. The resulting reaction solution was filtered through Celite, concentrated under reduced pressure, and then purified by column with a CH2Cl2 / AcOEt mixture to obtain compound (1-1-3) (4 mmol). In a glass reaction vessel, the obtained compounds (1-1-3) (4 mmol), (1-1-4) (10.4 mmol), and THF (20 mL) were placed, and piperidine (2 mL) was added under a nitrogen atmosphere. After reacting at 70°C for 4 hours, the solid was collected by filtration. The obtained solid was washed with MeOH, THF, and toluene, and purified by sublimation to obtain compound (B-1) (2.4 mmol). Compound (B-1): LDI-MS 616.0(M + ).

[0148] Compounds (B-2) to (B-59) and compounds (C-1) to (C-4) were synthesized by referring to the synthesis method of compound (B-1) described above.

[0149] The following lists each of the compounds being evaluated.

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] [ka]

[0155] [n-type organic semiconductor] C60: Fullerene (C 60 )

[0156] [p-type organic semiconductor]

[0157] [ka]

[0158] 〔evaluation〕 [Fabrication of photoelectric conversion elements] Using the obtained compound, a photoelectric conversion element in the form shown in Figure 2 was fabricated. Here, the photoelectric conversion element consists of a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15. Specifically, an amorphous ITO film was deposited on a glass substrate by sputtering to form a lower electrode 11 (thickness: 30 nm). Then, the following compound (F-1) was deposited on the lower electrode 11 by vacuum heating deposition to form an electron blocking film 16A (thickness: 30 nm). Furthermore, the evaluation compound, p-type organic semiconductor material, and n-type organic semiconductor material shown in Table 1 were deposited on the electron blocking film 16A in the component ratios shown in Table 1 to form a photoelectric conversion film 12 having a bulk heterostructure. Furthermore, the following compound (F-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). An amorphous ITO film was deposited on the hole blocking film 16B by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm). A photoelectric conversion element was fabricated by forming an SiO film as a sealing layer on the upper electrode 15 using vacuum deposition, and then forming an aluminum oxide (Al2O3) layer on top of it using ALCVD (Atomic Layer Chemical Vapor Deposition).

[0159] [ka]

[0160] [Variation in dark current] Ten photoelectric conversion elements were fabricated for each example and comparative example using the method described above, and the dark current of each obtained photoelectric conversion element was measured using the following method. 2.5 × 10⁻¹⁶ of the lower and upper electrodes of each photoelectric conversion element were used. 5 A voltage was applied to achieve an electric field strength of V / cm, and the current value in the dark (dark current) was measured. The ratio of dark currents was calculated using the following formula and evaluated according to the following criteria. Relative ratio of dark current = (Highest dark current value among 10 photoelectric conversion elements) / (Lowest dark current value among 10 photoelectric conversion elements) A: The relative ratio of dark currents is less than 2.0 B: The relative ratio of dark currents is 2.0 or higher, but less than 2.5. C: Relative ratio of dark current is 2.5 or higher, but less than 3.0. D: Relative ratio of dark current is 3.0 or higher, but less than 3.5. E: Relative ratio of dark current is 3.5 or higher, but less than 4.0. F: Relative ratio of dark current is 4.0 or higher

[0161] [Evaluation of photoelectric conversion efficiency (external quantum efficiency)] The operation of each photoelectric conversion element was confirmed. 2.0 × 10⁻¹⁰ 5 A voltage was applied to achieve an electric field strength of V / cm. Subsequently, light was irradiated from the upper electrode (transparent conductive film) side, and the photoelectric conversion efficiency (external quantum efficiency) for light with a wavelength of 460 nm was evaluated. The relative ratio of the integral values ​​of the photoelectric conversion efficiency was calculated from equation (S) and evaluated according to the following criteria. Equation (S) Relative ratio of photoelectric conversion efficiencies = (Photoelectric conversion efficiency of each example or comparative example for light with a wavelength of 460 nm) / (Photoelectric conversion efficiency of Comparative Example 1-1 for light with a wavelength of 460 nm) A: Relative ratio of photoelectric conversion efficiency is 1.4 or higher B: Relative ratio of photoelectric conversion efficiency is 1.2 or higher, but less than 1.4. C: Relative ratio of photoelectric conversion efficiency is 1.0 or higher, but less than 1.2. D: Relative ratio of photoelectric conversion efficiency is 0.8 or higher, but less than 1.0. E: Relative ratio of photoelectric conversion efficiency is less than 0.8

[0162] Table 1 shows the evaluation results. In the table, each notation has the following meaning: The columns "Formula (11) to Formula (38)" indicate the formula to which a specific compound belongs. The "Number of monorings in D" column shows the total number of monorings that make up D. The definition of the total number of monorings that make up D is as described above. The "Number of X groups in D" column indicates the number of X groups that D possesses. The definition of X groups is as described above. The "Number of Y groups in A" column indicates the number of Y groups present in A. The definition of a Y group is as described above. The above number of Y groups indicates the number of Y groups in one of the two A's present in a particular compound. In other words, the above number of Y groups indicates the number of Y groups in a single A, not the total number of Y groups present in the particular compound. Specifically, the total number of Y groups in compound (B-1) is 4, and the "Number of Y groups in A" above is 2. The "Molecular Shape" column indicates that, if it is A, the structure of D in the specific compound is linear and the structure of A is planar; if it is B, it indicates any other molecular shape. The definition of linearity is as described above.

[0163] [Table 1]

[0164] [Table 2]

[0165] The results shown in the table above confirm that the photoelectric conversion element of the present invention provides the effects of the present invention. It was confirmed that the effects of the present invention are superior when the number of monorings of D is 4 to 5 (preferably 4) (comparison between Examples 1-1 to 1-45 and Examples 1-46 to 1-53). Similarly, from a comparison, it was confirmed that the effects of the present invention are superior when the specific compound includes a compound represented by any of formulas (11) to (13), formulas (17) to (19), formulas (23) to (26), and formulas (29) to (32) (preferably a compound represented by any of formulas (11), (12), (17), (18), (23), (24), (29), and (30)). It was confirmed that the effects of the present invention are superior when D has two or four atoms or groups selected from the group consisting of -N=, halogen atoms, trifluoromethyl groups, and cyano groups, and A has three to four atoms or groups selected from the group consisting of -N=, halogen atoms, cyano groups, trifluoromethyl groups, sulfonyl groups, carbonyl groups, and thiocarbonyl groups (comparison of Examples 1-3, 1-21, and 1-26, and comparison of Examples 1-1 to 1-21, etc.). It has been confirmed that the effects of the present invention are superior when the structure of D in a specific compound is linear and the structure of A has a planar molecular shape (comparison of Examples 1-1 to 1-21, etc.). [Explanation of Symbols]

[0166] 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, A photoelectric conversion element wherein the photoelectric conversion film contains a compound represented by formula (1). A-D-A (1) In formula (1), A represents the group represented by formula (A-1). D represents the group represented by any of formulas (2) to (4). Note that the two A's represent the same group. 【Chemistry 1】 In formula (A-1), * represents a bonding position. R Ｂ represents a hydrogen atom or an alkyl group which may have a substituent. C １ contains two or more carbon atoms as ring member atoms and represents a ring group which may have a substituent. Z １ represents an oxygen atom, a sulfur atom, =NR Ｚ１ or =CR Ｚ２ R Ｚ３ represents. R Ｚ１ represents a hydrogen atom or a substituent. R Ｚ２ and R Ｚ３ each independently represent a cyano group, -SO ２ R Ｚ４ , -COOR Ｚ５ or -COR Ｚ６ represents. R Ｚ４ to R Ｚ６ each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent or a heteroaryl group which may have a substituent. 【Chemistry 2】 In equations (2) to (4), * indicates the bonding position. In formula (2), Ar １ This represents a group represented by any of the formulas (7) to (10). Note that the two Ar １ These represent the same base. In formula (3), Ar ２ and Ar ３ One of the two Ar groups represents a group represented by any of formulas (7) to (10), and the other represents a group represented by any of formulas (5) to (10). ３ Ar represents the same base. ２ and Ar ３ They may be the same or different. In formula (4), Ar ４ and Ar ５ One of the two Ar groups represents a group represented by any of formulas (7) to (10), and the other represents a group represented by either formula (5) or formula (6). ４ These represent the same group, and the two Ar ５ These represent the same base. 【Transformation 3】 In equations (5) to (10), * indicates the bonding position. In formula (5), Y ５１ ~Y ５４ Each of these is independently -CR Ａ５ = or represents a nitrogen atom. R Ａ５ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (6), X ６１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ６１ and Y ６２ Each of these is independently -CR Ａ６ = or represents a nitrogen atom. R Ａ６ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (7), Y ７１ ~Y ７６ Each of these is independently -CR Ａ７ = or represents a nitrogen atom. R Ａ７ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (8), X ８１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ８１ ~Y ８４ Each of these is independently -CR Ａ８ = or represents a nitrogen atom. R Ａ８ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (9), X ９１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ９１ ~Y ９４ Each of these is independently -CR Ａ９ = or represents a nitrogen atom. R Ａ９ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (10), X １０１ and X １０２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １０１ and Y １０２ Each of these is independently -CR Ａ１０ = or represents a nitrogen atom. R Ａ１０ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group.

2. The photoelectric conversion element according to claim 1, wherein the compound represented by formula (1) includes a compound represented by any one of formulas (11) to (38). 【Chemistry 4】 【change】 In formula (11), X １１１ This represents an oxygen atom, a sulfur atom, or a selenium atom. １１１ is, -CR Ａ１１ = or represents a nitrogen atom. R Ａ１１ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １１ This represents the group represented by formula (5) or the group represented by formula (6). １１ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１１ They may be the same or different. In formula (12), X １２１ and X １２２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １２１ and Y １２２ Each of these is independently -CR Ａ１２ = or represents a nitrogen atom. R Ａ１２ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １２ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１２ They may be the same or different. In formula (13), X １３１ and X １３２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １３１ and Y １３２ Each of these is independently -CR Ａ１３ = or represents a nitrogen atom. R Ａ１３ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １３ This represents the group represented by formula (5) or the group represented by formula (6). １３ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１３ They may be the same or different. In formula (14), X １４１ and X １４２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １４１ and Y １４２ Each of these is independently -CR Ａ１４ = or represents a nitrogen atom. R Ａ１４ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １４ This represents the group represented by formula (5) or the group represented by formula (6). １４ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１４ They may be the same or different. In formula (15), X １５１ to X １５３ each independently represents an oxygen atom, a sulfur atom, or a selenium atom. Y １５１ to Y １５３ each independently represents -CR Ａ１５ = or a nitrogen atom. R Ａ１５ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. A １５ represents a group represented by the formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１５ may be the same or different. In formula (16), X １６１ and X １６２ each independently represents an oxygen atom, a sulfur atom, or a selenium atom. Y １６１ to Y １６５ each independently represents -CR Ａ１６ = or a nitrogen atom. R Ａ１６ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. A １６ represents a group represented by the said formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１６ may be the same or different. In formula (17), Y １７１ ~Y １７３ Each of these is independently -CR Ａ１７ = or represents a nitrogen atom. R Ａ１７ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １７ This represents the group represented by formula (5) or the group represented by formula (6). １７ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１７ They may be the same or different. In formula (18), Y １８１ ~Y １８６ Each of these is independently -CR Ａ１８ = or represents a nitrogen atom. R Ａ１８ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １８ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１８ They may be the same or different. In formula (19), Y １９１ ~Y １９６ Each of these is independently -CR Ａ１９ = or represents a nitrogen atom. R Ａ１９ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １９ This represents the group represented by formula (5) or the group represented by formula (6). １９ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１９ They may be the same or different. In formula (20), Y ２０１ ~Y ２０６ Each of these is independently -CR Ａ２０ = or represents a nitrogen atom. R Ａ２０ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２０ This represents the group represented by formula (5) or the group represented by formula (6). ２０ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２０ They may be the same or different. In formula (21), Y ２１１ ~Y ２１９ Each of these is independently -CR Ａ２１ = or represents a nitrogen atom. R Ａ２１ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２１ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２１ They may be the same or different. In formula (22), X ２２１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２２１ ~Y ２２６ Each of these is independently -CR Ａ２２ = or represents a nitrogen atom. R Ａ２２ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２２ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２２ They may be the same or different. In formula (23), X ２３１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２３１ ~Y ２３４ Each of these is independently -CR Ａ２３ = or represents a nitrogen atom. R Ａ２３ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２３ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２３ They may be the same or different. In formula (24), X ２４１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２４１ ~Y ２４４ Each of these is independently -CR Ａ２４ = or represents a nitrogen atom. R Ａ２４ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２４ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２４ They may be the same or different. In formula (25), X ２５１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２５１ ~Y ２５４ Each of these is independently -CR Ａ２５ = or represents a nitrogen atom. R Ａ２５ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２５ This represents the group represented by formula (5) or the group represented by formula (6). ２５ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２５ They may be the same or different. In formula (26), X ２６１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２６１ ~Y ２６４ Each of these is independently -CR Ａ２６ = or represents a nitrogen atom. R Ａ２６ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２６ This represents the group represented by formula (5) or the group represented by formula (6). ２６ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２６ They may be the same or different. In formula (27), X ２７１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２７１ ~Y ２７４ Each of these is independently -CR Ａ２７ = or represents a nitrogen atom. R Ａ２７ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２７ This represents the group represented by formula (5) or the group represented by formula (6). ２７ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２７ They may be the same or different. In formula (28), X ２８１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２８１ ~Y ２８４ Each of these is independently -CR Ａ２８ = or represents a nitrogen atom. R Ａ２８ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２８ This represents the group represented by formula (5) or the group represented by formula (6). ２８ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２８ They may be the same or different. In formula (29), X ２９１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２９１ ~Y ２９４ Each of these is independently -CR Ａ２９ = or represents a nitrogen atom. R Ａ２９ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２９ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２９ They may be the same or different. In formula (30), X ３０１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３０１ ~Y ３０４ Each of these is independently -CR Ａ３０ = or represents a nitrogen atom. R Ａ３０ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３０ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３０ They may be the same or different. In formula (31), X ３１１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３１１ ~Y ３１４ Each of these is independently -CR Ａ３１ = or represents a nitrogen atom. R Ａ３１ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３１ This represents the group represented by formula (5) or the group represented by formula (6). ３１ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３１ They may be the same or different. In formula (32), X ３２１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３２１ ~Y ３２４ Each of these is independently -CR Ａ３２ = or represents a nitrogen atom. R Ａ３２ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３２ This represents the group represented by formula (5) or the group represented by formula (6). ３２ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３２ They may be the same or different. In formula (33), X ３３１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３３１ ~Y ３３４ Each of these is independently -CR Ａ３３ = or represents a nitrogen atom. R Ａ３３ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３３ This represents the group represented by formula (5) or the group represented by formula (6). ３３ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３３ They may be the same or different. In formula (34), X ３４１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３４１ ~Y ３４４ Each of these is independently -CR Ａ３４ = or represents a nitrogen atom. R Ａ３４ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３４ This represents the group represented by formula (5) or the group represented by formula (6). ３４ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３４ They may be the same or different. In formula (35), X ３５１ and X ３５２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. ３５１ ~Y ３５５ Each of these is independently -CR Ａ３５ = or represents a nitrogen atom. R Ａ３５ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３５ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３５ They may be the same or different. In formula (36), X ３６１ and X ３６２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. ３６１ ~Y ３６５ Each of these is independently -CR Ａ３６ = or represents a nitrogen atom. R Ａ３６ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３６ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３６ They may be the same or different. In formula (37), X ３７１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３７１ ~Y ３７７ Each of these is independently -CR Ａ３７ = or represents a nitrogen atom. R Ａ３７ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３７ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３７ They may be the same or different. In formula (38), X ３８１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３８１ ~Y ３８７ Each of these is independently -CR Ａ３８ = or represents a nitrogen atom. R Ａ３８ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３８ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３８ They may be the same or different.

3. The photoelectric conversion element according to claim 2, wherein the compound represented by formula (1) includes a compound represented by any of formulas (11) to (13), formulas (17) to (19), formulas (23) to (26), and formulas (29) to (32).

4. The photoelectric conversion element according to claim 3, wherein the compound represented by formula (1) includes a compound represented by any one of formulas (11), (12), (17), (18), (23), (24), (29), and (30).

5. The photoelectric conversion element according to claim 4, wherein the compound represented by formula (1) includes the compound represented by formula (11) or the compound represented by formula (12).

6. The photoelectric conversion element according to any one of claims 1 to 5, wherein D comprises at least one ring selected from the group consisting of a furan ring, a thiophene ring, a thiazole ring, and an oxazole ring.

7. A photoelectric element according to any one of claims 1 to 5, wherein D has two or four atoms or groups selected from the group consisting of -N=, halogen atoms, trifluoromethyl groups, and cyano groups, and A has three to four atoms or groups selected from the group consisting of -N=, halogen atoms, cyano groups, trifluoromethyl groups, sulfonyl groups, carbonyl groups, and thiocarbonyl groups.

8. The photoelectric conversion element according to any one of claims 1 to 5, wherein the molecular weight of the compound represented by formula (1) is 900 or less.

9. The photoelectric conversion element according to any one of claims 1 to 5, wherein the photoelectric conversion film further comprises an n-type organic semiconductor.

10. The photoelectric conversion element according to claim 9, wherein the n-type organic semiconductor comprises fullerenes selected from the group consisting of fullerenes and their derivatives.

11. The photoelectric conversion element according to any one of claims 1 to 5, wherein the photoelectric conversion film further comprises a p-type organic semiconductor.

12. The photoelectric conversion element according to any one of claims 1 to 5, wherein the photoelectric conversion film further comprises a dye.

13. A photoelectric conversion element according to any one of claims 1 to 5, wherein the conductive film and the transparent conductive film are interposed between them, and one or more intermediate layers in addition to the photoelectric conversion film.

14. An image sensor having a photoelectric conversion element according to any one of claims 1 to 5.

15. A light sensor having a photoelectric conversion element according to any one of claims 1 to 5.

16. A compound represented by formula (1). A-D-A (1) In formula (1), A represents the group represented by formula (A-1). D represents the group represented by any of formulas (2) to (4). Note that the two A's represent the same group. 【Transformation 5】 In formula (A-1), * indicates the bonding position. Ｂ C represents an alkyl group which may have a hydrogen atom or substituents. １ This represents a ring group containing two or more carbon atoms as ring member atoms, and which may have substituents. １ This consists of an oxygen atom, a sulfur atom, and =NR Ｚ１ or = CR Ｚ２ R Ｚ３ Represents R Ｚ１ R represents a hydrogen atom or substituent. Ｚ２ and R Ｚ３ These are, independently, a cyano group and -SO ２ R Ｚ４ , -COOR Ｚ５ or -COR Ｚ６ Represents R Ｚ４ ~R Ｚ６ Each of these independently represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group. 【Transformation 6】 In equations (2) to (4), * indicates the bonding position. In formula (2), Ar １ This represents a group represented by any of the formulas (7) to (10). Note that the two Ar １ These represent the same base. In formula (3), Ar ２ and Ar ３ One of the two Ar groups represents a group represented by any of formulas (7) to (10), and the other represents a group represented by any of formulas (5) to (10). ３ Ar represents the same base. ２ and Ar ３ They may be the same or different. In formula (4), Ar ４ and Ar ５ One of the two Ar groups represents a group represented by any of formulas (7) to (10), and the other represents a group represented by either formula (5) or formula (6). ４ These represent the same group, and the two Ar ５ These represent the same base. 【Transformation 7】 In equations (5) to (10), * indicates the bonding position. In formula (5), Y ５１ ~Y ５４ Each of these is independently -CR Ａ５ = or represents a nitrogen atom. R Ａ５ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (6), X ６１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ６１ and Y ６２ Each of these is independently -CR Ａ６ = or represents a nitrogen atom. R Ａ６ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (7), Y ７１ ~Y ７６ Each of these is independently -CR Ａ７ = or represents a nitrogen atom. R Ａ７ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (8), X ８１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ８１ ~Y ８４ Each of these is independently -CR Ａ８ = or represents a nitrogen atom. R Ａ８ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (9), X ９１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ９１ ~Y ９４ Each of these is independently -CR Ａ９ = or represents a nitrogen atom. R Ａ９ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. In formula (10), X １０１ and X １０２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １０１ and Y １０２ Each of these is independently -CR Ａ１０ = or represents a nitrogen atom. R Ａ１０ represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group.

17. The compound according to claim 16, which is a compound represented by any of formulas (11) to (38). 【Transformation 8】 【change】 In formula (11), X １１１ This represents an oxygen atom, a sulfur atom, or a selenium atom. １１１ is, -CR Ａ１１ = or represents a nitrogen atom. R Ａ１１ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １１ This represents the group represented by formula (5) or the group represented by formula (6). １１ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１１ They may be the same or different. In formula (12), X １２１ and X １２２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １２１ and Y １２２ Each of these is independently -CR Ａ１２ = or represents a nitrogen atom. R Ａ１２ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １２ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１２ They may be the same or different. In formula (13), X １３１ and X １３２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １３１ and Y １３２ Each of these is independently -CR Ａ１３ = or represents a nitrogen atom. R Ａ１３ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １３ This represents the group represented by formula (5) or the group represented by formula (6). １３ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１３ They may be the same or different. In formula (14), X １４１ and X １４２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １４１ and Y １４２ Each of these is independently -CR Ａ１４ = or represents a nitrogen atom. R Ａ１４ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １４ This represents the group represented by formula (5) or the group represented by formula (6). １４ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１４ They may be the same or different. In formula (15), X １５１ ~X １５３ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １５１ ~Y １５３ Each of these is independently -CR Ａ１５ = or represents a nitrogen atom. R Ａ１５ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １５ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１５ They may be the same or different. In formula (16), X １６１ and X １６２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. １６１ ~Y １６５ Each of these is independently -CR Ａ１６ = or represents a nitrogen atom. R Ａ１６ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １６ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１６ They may be the same or different. In formula (17), Y １７１ ~Y １７３ Each of these is independently -CR Ａ１７ = or represents a nitrogen atom. R Ａ１７ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １７ This represents the group represented by formula (5) or the group represented by formula (6). １７ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１７ They may be the same or different. In formula (18), Y １８１ ~Y １８６ Each of these is independently -CR Ａ１８ = or represents a nitrogen atom. R Ａ１８ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １８ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１８ They may be the same or different. In formula (19), Y １９１ ~Y １９６ Each of these is independently -CR Ａ１９ = or represents a nitrogen atom. R Ａ１９ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. １９ This represents the group represented by formula (5) or the group represented by formula (6). １９ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ１９ They may be the same or different. In formula (20), Y ２０１ ~Y ２０６ Each of these is independently -CR Ａ２０ = or represents a nitrogen atom. R Ａ２０ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２０ This represents the group represented by formula (5) or the group represented by formula (6). ２０ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２０ They may be the same or different. In formula (21), Y ２１１ ~Y ２１９ Each of these is independently -CR Ａ２１ = or represents a nitrogen atom. R Ａ２１ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２１ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２１ They may be the same or different. In formula (22), X ２２１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２２１ ~Y ２２６ Each of these is independently -CR Ａ２２ = or represents a nitrogen atom. R Ａ２２ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２２ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２２ They may be the same or different. In formula (23), X ２３１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２３１ ~Y ２３４ Each of these is independently -CR Ａ２３ = or represents a nitrogen atom. R Ａ２３ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２３ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２３ They may be the same or different. In formula (24), X ２４１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２４１ ~Y ２４４ Each of these is independently -CR Ａ２４ = or represents a nitrogen atom. R Ａ２４ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２４ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２４ They may be the same or different. In formula (25), X ２５１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２５１ ~Y ２５４ Each of these is independently -CR Ａ２５ = or represents a nitrogen atom. R Ａ２５ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２５ This represents the group represented by formula (5) or the group represented by formula (6). ２５ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２５ They may be the same or different. In formula (26), X ２６１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２６１ ~Y ２６４ Each of these is independently -CR Ａ２６ = or represents a nitrogen atom. R Ａ２６ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２６ This represents the group represented by formula (5) or the group represented by formula (6). ２６ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２６ They may be the same or different. In formula (27), X ２７１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２７１ ~Y ２７４ Each of these is independently -CR Ａ２７ = or represents a nitrogen atom. R Ａ２７ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２７ This represents the group represented by formula (5) or the group represented by formula (6). ２７ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２７ They may be the same or different. In formula (28), X ２８１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２８１ ~Y ２８４ Each of these is independently -CR Ａ２８ = or represents a nitrogen atom. R Ａ２８ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２８ This represents the group represented by formula (5) or the group represented by formula (6). ２８ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２８ They may be the same or different. In formula (29), X ２９１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ２９１ ~Y ２９４ Each of these is independently -CR Ａ２９ = or represents a nitrogen atom. R Ａ２９ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ２９ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ２９ They may be the same or different. In formula (30), X ３０１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３０１ ~Y ３０４ Each of these is independently -CR Ａ３０ = or represents a nitrogen atom. R Ａ３０ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３０ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３０ They may be the same or different. In formula (31), X ３１１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３１１ ~Y ３１４ Each of these is independently -CR Ａ３１ = or represents a nitrogen atom. R Ａ３１ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３１ This represents the group represented by formula (5) or the group represented by formula (6). ３１ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３１ They may be the same or different. In formula (32), X ３２１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３２１ ~Y ３２４ Each of these is independently -CR Ａ３２ = or represents a nitrogen atom. R Ａ３２ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３２ This represents the group represented by formula (5) or the group represented by formula (6). ３２ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３２ They may be the same or different. In formula (33), X ３３１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３３１ ~Y ３３４ Each of these is independently -CR Ａ３３ = or represents a nitrogen atom. R Ａ３３ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３３ This represents the group represented by formula (5) or the group represented by formula (6). ３３ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３３ They may be the same or different. In formula (34), X ３４１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３４１ ~Y ３４４ Each of these is independently -CR Ａ３４ = or represents a nitrogen atom. R Ａ３４ Z represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３４ This represents the group represented by formula (5) or the group represented by formula (6). ３４ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３４ They may be the same or different. In formula (35), X ３５１ and X ３５２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. ３５１ ~Y ３５５ Each of these is independently -CR Ａ３５ = or represents a nitrogen atom. R Ａ３５ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３５ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３５ They may be the same or different. In formula (36), X ３６１ and X ３６２ Each of these independently represents an oxygen atom, a sulfur atom, or a selenium atom. ３６１ ~Y ３６５ Each of these is independently -CR Ａ３６ = or represents a nitrogen atom. R Ａ３６ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３６ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３６ They may be the same or different. In formula (37), X ３７１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３７１ ~Y ３７７ Each of these is independently -CR Ａ３７ = or represents a nitrogen atom. R Ａ３７ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３７ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３７ They may be the same or different. In formula (38), X ３８１ This represents an oxygen atom, a sulfur atom, or a selenium atom. ３８１ ~Y ３８７ Each of these is independently -CR Ａ３８ = or represents a nitrogen atom. R Ａ３８ A represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group. ３８ R represents the group represented by the above formula (A-1). Note that groups represented by the same notation represent the same group. However, R Ａ３８ They may be the same or different.

18. The compound according to claim 17, which is a compound represented by any of the following formulas: (11) to (13), (17) to (19), (23) to (26), and (29) to (32).

19. The compound according to claim 18, which is a compound represented by any one of the above formulas (11), (12), (17), (18), (23), (24), (29), and (30).

20. The compound according to claim 19, which is a compound represented by formula (11) or a compound represented by formula (12).

21. The compound according to any one of claims 16 to 20, wherein D comprises at least one ring selected from the group consisting of a furan ring, a thiophene ring, a thiazole ring, and an oxazole ring.

22. The compound according to any one of claims 16 to 20, wherein D has two or four atoms or groups selected from the group consisting of -N=, halogen atoms, trifluoromethyl groups, and cyano groups, and A has three to four atoms or groups selected from the group consisting of -N=, halogen atoms, cyano groups, trifluoromethyl groups, sulfonyl groups, carbonyl groups, and thiocarbonyl groups.

23. The compound according to any one of claims 16 to 20, wherein the molecular weight of the compound represented by formula (1) is 900 or less.

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