Photoelectric conversion elements, imaging elements, optical sensors, compounds

Abstract

The present invention provides a photoelectric conversion element having excellent heat resistance. In addition, an imaging element and a light sensor comprising the photoelectric conversion element are provided. In addition, a compound used in the photoelectric conversion element is provided. The photoelectric conversion element of the present invention has a conductive film, a photoelectric conversion film and a transparent conductive film in sequence, wherein the photoelectric conversion film comprises a compound represented by formula (1). In formula (1), Y 1 It represents a group represented by formula (1-1) or a group represented by formula (1-2). #imgabs0#

Description

Technical Field

[0001] The invention relates to a photoelectric conversion element, an imaging element, a light sensor and a compound. Background Art

[0002] In recent years, development of devices having a photoelectric conversion film has been underway.

[0003] For example, Patent Document 1 discloses a compound represented by the following formula as a material used for a photoelectric conversion element (claim 1).

[0004] [Chemical formula 1]

[0005]

[0006] Previous technical literature

[0007] Patent Literature

[0008] Patent Document 1: Japanese Patent Application Publication No. 2009-167348 Summary of the invention

[0009] Technical issues to be solved by the invention

[0010] In recent years, as there has been a demand for improved performance of imaging devices, optical sensors, and the like, there has been a demand for further improvement in various properties required of photoelectric conversion elements used therein.

[0011] For example, photoelectric conversion elements are required to have excellent heat resistance.

[0012] The present inventors produced a photoelectric conversion element using the compound disclosed in Patent Document 1 and evaluated the heat resistance of the obtained photoelectric conversion element. As a result, they found that there is room for improvement.

[0013] In view of the above circumstances, an object of the present invention is to provide a photoelectric conversion element having excellent heat resistance.

[0014] In addition, the present invention provides an imaging device and a photosensor including the above-mentioned photoelectric conversion element. In addition, the present invention provides a compound used in the above-mentioned photoelectric conversion element.

[0015] Means for solving technical problems

[0016] As a result of intensive studies on the above-mentioned problems, the present inventors have found that the above-mentioned problems can be solved by using a compound having a predetermined structure in a photoelectric conversion film, thereby completing the present invention.

[0017] [1]

[0018] A photoelectric conversion element comprises a conductive film, a photoelectric conversion film and a transparent conductive film in sequence, wherein:

[0019] The photoelectric conversion film contains a compound represented by formula (1) described below.

[0020] [2]

[0021] The photoelectric conversion element according to [1], wherein

[0022] The compound represented by the formula (1) described later is a compound represented by the formula (2) described later.

[0023] 〔3〕

[0024] The photoelectric conversion element according to [1] or [2], wherein:

[0025] The compound represented by the formula (1) described later is a compound represented by the formula (3) described later.

[0026] [4]

[0027] The photoelectric conversion element according to any one of [1] to [3], wherein

[0028] The compound represented by the formula (1) described later is a compound represented by the formula (4) described later.

[0029] 〔5〕

[0030] The photoelectric conversion element according to any one of [1] to [4], wherein

[0031] The compound represented by the formula (1) described later is a compound represented by the formula (5) described later.

[0032] [6]

[0033] The photoelectric conversion element according to any one of [1] to [5], wherein

[0034] In the formulas (1) to (5) described below, R a1 and R a2 Each independently represents a group represented by the formula (X) described below, -C(R L1 )(R L2 )(R L3 ), a polycyclic aryl group which may have a substituent, or a polycyclic heteroaryl group which may have a substituent.

[0035] 〔7〕

[0036] The photoelectric conversion element according to any one of [1] to [6], wherein

[0037] The photoelectric conversion film further comprises an n-type organic semiconductor.

[0038] The photoelectric conversion film has a bulk heterostructure formed in a state where a compound represented by formula (1) described later and the n-type organic semiconductor are mixed.

[0039] [8]

[0040] The photoelectric conversion element according to [7], wherein:

[0041] The organic n-type semiconductor includes fullerenes selected from the group consisting of fullerenes and derivatives thereof.

[0042] 〔9〕

[0043] The photoelectric conversion element according to any one of [1] to [8], wherein

[0044] In addition to the photoelectric conversion film, one or more intermediate layers are provided between the conductive film and the transparent conductive film.

[0045] 〔10〕

[0046] An imaging element having the photoelectric conversion element described in any one of [1] to [9].

[0047]

[11]

[0048] The imaging element according to

[10] further comprises another photoelectric conversion element that receives light having a wavelength different from the light received by the above-mentioned photoelectric conversion element.

[0049]

[12]

[0050] An imaging element according to

[11] , wherein:

[0051] The above-mentioned photoelectric conversion element and the above-mentioned other photoelectric conversion element are stacked,

[0052] At least a portion of the incident light is transmitted through the photoelectric conversion element and then received by the other photoelectric conversion element.

[0053] 〔13〕

[0054] An imaging element according to

[11] or

[12] , wherein:

[0055] The above-mentioned photoelectric conversion element is a green photoelectric conversion element,

[0056] The other photoelectric conversion elements include a blue photoelectric conversion element and a red photoelectric conversion element.

[0057]

[14]

[0058] A photosensor having the photoelectric conversion element described in any one of [1] to [9].

[0059] 〔15〕

[0060] A compound represented by the formula (4-2) described below.

[0061] Effects of the Invention

[0062] According to the present invention, a photoelectric conversion element having excellent heat resistance can be provided.

[0063] Furthermore, according to the present invention, an imaging device and a photosensor including the above-mentioned photoelectric conversion element can be provided. Furthermore, according to the present invention, a compound used for the above-mentioned photoelectric conversion element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0064] Figure 1 It is a schematic cross-sectional view showing a structural example of a photoelectric conversion element.

[0065] Figure 2 It is a schematic cross-sectional view showing a structural example of a photoelectric conversion element.

[0066] Figure 3 It is a schematic cross-sectional view of one embodiment of an imaging element.

[0067] Figure 4 is compound (D-1) 1 H NMR (Nuclear Magnetic Resonance) graph.

[0068] Figure 5 is compound (D-2) 1 H NMR spectra.

[0069] Figure 6 Compound (D-3) 1 H NMR spectra.

[0070] Figure 7 Compound (D-4) 1 H NMR spectra.

[0071] Figure 8 Compound (D-5) 1 H NMR spectra.

[0072] Fig. 9 Compound (D-7) 1 H NMR spectra.

[0073] Fig.10 Compound (D-10) 1 H NMR spectra.

[0074] Fig.11 Compound (D-11) 1 H NMR spectra.

[0075] Fig.12 Compound (D-12) 1 H NMR spectra.

[0076] Fig.13 Compound (D-13) 1 H NMR spectra.

[0077] Fig.14 Compound (D-14) 1 H NMR spectra.

[0078] Fig.15 It is compound (D-16) 1 H NMR spectra.

[0079] Fig.16 It is compound (D-25) 1 H NMR spectra.

[0080] Fig.17 Compound (D-26) 1 H NMR spectra.

[0081] Fig.18 Compound (D-27) 1 H NMR spectra.

[0082] Fig.19 It is compound (D-28) 1 H NMR spectra.

[0083] Fig. 20 Compound (D-29) 1 H NMR spectra.

[0084] Fig.21 Compound (D-31) 1 H NMR spectra.

[0085] Fig. 22 Compound (D-32) 1 H NMR spectra.

[0086] Fig.23 It is compound (D-34) 1 H NMR spectra.

[0087] Fig.24 Compound (D-35) 1 H NMR spectra.

[0088] Fig.25 It is compound (D-37) 1 H NMR spectra.

[0089] Fig.26 It is compound (D-38) 1 H NMR spectra.

[0090] Fig. 27 It is compound (D-39) 1 H NMR spectra.

[0091] Fig.28 It is compound (D-40) 1 H NMR spectra.

[0092] Fig.29 Compound (D-41) 1 H NMR spectra.

[0093] Fig.30 It is compound (D-45) 1 H NMR spectra.

[0094] Fig.31 It is compound (D-46) 1 H NMR spectra.

[0095] Fig.32 It is compound (D-47) 1 H NMR spectra.

[0096] Fig.33 It is compound (D-48) 1 H NMR spectra.

[0097] Fig.34 It is compound (D-59) 1 H NMR spectra.

[0098] Fig.35 It is compound (D-69) 1 H NMR spectra.

[0099] Fig.36 It is compound (D-71) 1 H NMR spectra.

[0100] Fig.37 It is compound (D-75) 1 H NMR spectra.

[0101] Fig.38 It is compound (D-76) 1 H NMR spectra. DETAILED DESCRIPTION

[0102] Hereinafter, preferred embodiments of the photoelectric conversion element of the present invention will be described.

[0103] In addition, in the present specification, for substituents that are not indicated as substituted or unsubstituted, the group may be further substituted with a substituent (e.g., a substituent W described below) within the range that does not impair the intended effect. For example, the notation "alkyl" means an alkyl group that may be substituted with a substituent (e.g., a substituent W described below), and the alkyl group may have a substituent (e.g., a substituent W described below) or may not have a substituent.

[0104] Furthermore, in the present specification, a numerical range expressed using “to” means a range including the numerical values ​​described before and after “to” as the lower limit and the upper limit.

[0105] In this specification, when there are multiple substituents and linking groups (hereinafter, also referred to as substituents, etc.) represented by specific symbols, or when multiple substituents, etc. are specified at the same time, it means that the substituents, etc. may be the same or different from each other. The same applies to the number of substituents, etc.

[0106] In the present specification, the hydrogen atom may be a light hydrogen atom (ordinary hydrogen atom) or a heavy hydrogen atom (such as a dihydrogen atom).

[0107] 〔Photoelectric conversion element〕

[0108] As a characteristic point of the present invention compared with the prior art, the point that a compound represented by formula (1) described later (hereinafter also referred to as a "specific compound") is used in the photoelectric conversion film.

[0109] The present inventors believe that since a relatively large substituent (R in formula (1)) is bonded to a predetermined nitrogen atom in a specific compound, a1 and R a2 ), so even when heated, the crystallization of the specific compound can be suppressed, and the performance degradation (increase in dark current, etc.) caused by heating of the photoelectric conversion element can be avoided.

[0110] Figure 1 Schematic cross-sectional view of one embodiment of the photoelectric conversion element of the present invention is shown in FIG.

[0111] Figure 1 The photoelectric conversion element 10a shown has the following structure stacked in sequence: a conductive film (hereinafter, also referred to as the lower electrode) 11 acting as a lower electrode; an electron blocking film (electron blocking film) 16A; a photoelectric conversion film 12 containing a specific compound described later; and a transparent conductive film (hereinafter, also referred to as the upper electrode) 15 acting as an upper electrode.

[0112] exist Figure 2 Another example of the structure of a photoelectric conversion element is shown in FIG. Figure 2 The photoelectric conversion element 10b shown has a structure in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are sequentially stacked on a lower electrode 11. Figure 1 and Figure 2 The stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in the structure may be appropriately changed according to the application and characteristics.

[0113] In the photoelectric conversion element 10 a (or 10 b ), it is preferred that light enters the photoelectric conversion film 12 via the upper electrode 15 .

[0114] Furthermore, when the photoelectric conversion element 10a (or 10b) is used, a voltage can be applied. In this case, it is preferable that the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and a 1×10 -5 ~1×10 7 From the perspective of performance and power consumption, the applied voltage is more preferably 1×10 -4 ~1×10 7 V / cm, more preferably 1×10 -3 ~5×10 6 V / cm.

[0115] In addition, regarding the voltage application method, Figure 1 and Figure 2 In the embodiment, the voltage is preferably applied so that the electron blocking film 16A side becomes a cathode and the photoelectric conversion film 12 side becomes an anode. When the photoelectric conversion element 10a (or 10b) is used as a photosensor or incorporated in an imaging element, voltage can be applied by the same method.

[0116] As will be described in detail later, the photoelectric conversion element 10 a (or 10 b ) can be preferably used for imaging element applications.

[0117] Hereinafter, the configuration of each layer constituting the photoelectric conversion element of the present invention will be described in detail.

[0118] [Photoelectric conversion film]

[0119] <Specified compounds>

[0120] The photoelectric conversion film 12 (or the organic photoelectric conversion film 209) is a film containing a specific compound as a photoelectric conversion material. When the compound is used, a photoelectric conversion element having excellent heat resistance can be obtained.

[0121] Hereinafter, the specific compounds will be described in detail.

[0122] In addition, in formula (1), the 1 Formula (1) includes any geometric isomers differentiated by the C=C double bond formed by the bonded carbon atom and the adjacent carbon atom. That is, both the cis-isomer and the trans-isomer differentiated by the above C=C double bond are included in the compound represented by formula (1). This is also the case for formulas (2) and (3).

[0123] In the present specification, unless otherwise specified, examples of the substituent that a specific compound may have include the substituent W described below, each independently thereof.

[0124] Furthermore, unless otherwise specified, examples of alkyl groups (including alkyl groups that may have a substituent) that a specific compound may have include alkyl groups AL described below, respectively. Examples of aryl groups (including aryl groups that may have a substituent) include aryl groups AR described below, and examples of heteroaryl groups (including heteroaryl groups that may have a substituent) include heteroaryl groups HA described below, respectively.

[0125] (Formula (1))

[0126] The photoelectric conversion film included in the photoelectric conversion element of the present invention contains a specific compound.

[0127] The specific compound is a compound represented by formula (1).

[0128] [Chemical formula 2]

[0129]

[0130] In formula (1), Y 1 It represents a group represented by formula (1-1) or a group represented by formula (1-2). Among them, from the viewpoint of a better effect of the present invention, the group represented by formula (1-1) is preferred. In formula (1-1) and formula (1-2), * represents a bonding position, and the carbon atom marked with * and the carbon atom with R 1 The bonded carbon atoms form double bonds.

[0131] That is, the compound represented by formula (1) is a compound represented by formula (1-1a) or a compound represented by formula (1-2a).

[0132] In addition, the symbols used in formula (1-1a) and formula (1-2a) have the same meanings as the corresponding symbols used in formula (1).

[0133] [Chemical formula 3]

[0134]

[0135] In formula (1-1), A 1 represents a ring containing at least 2 carbon atoms which may have a substituent. In addition, the two carbon atoms represent the Z indicated in formula (1-1). 1 The carbon atom bonded to the above Z 1 The carbon atom indicated in formula (1-1) adjacent to the carbon atom to which the bond is attached (with R 1 The carbon atoms bonded to the double bond are all carbon atoms that make up A 1 of atoms.

[0136] Furthermore, the carbon atoms constituting the ring in the above ring may be substituted by other carbonyl carbons (>C=O) and / or other thiocarbonyl carbons (>C=S). In addition, the other carbonyl carbons (>C=O) and other thiocarbonyl carbons (>C=S) mentioned here mean that the carbon atoms constituting the ring are substituted by the carbon atoms Z. 1 Carbon atoms other than the bonding carbon atom serve as carbonyl carbon and thiocarbonyl carbon which are essential for the formation.

[0137] A 1 The number of carbon atoms in is preferably 3 to 30, more preferably 3 to 20, and still more preferably 3 to 15. The above-mentioned number of carbon atoms includes the two carbon atoms indicated in the formula.

[0138] A 1 It may have a hetero atom, and examples thereof include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom.

[0139] A 1 The number of heteroatoms in is preferably 0 to 10, more preferably 0 to 5, and still more preferably 0 to 2. 1 The number of heteroatoms introduced into the ring by replacing the carbon atoms of the ring represented by carbonyl carbon (>C=O) or thiocarbonyl carbon (>C=S) (the carbonyl carbon (>C=O) mentioned here means including the carbonyl carbon explicitly shown in formula (1-1)), and excluding A 1 The number of heteroatoms possessed by the substituent.

[0140] A 1It may have a substituent, and as the substituent, preferably a halogen atom (preferably a chlorine atom), an alkyl group (which may be any of linear, branched and cyclic. The number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6.), an aryl group (the number of carbon atoms is preferably 6 to 18, and more preferably 6 to 12.), a heteroaryl group (the number of carbon atoms is preferably 5 to 18, and more preferably 5 to 6.), or a silyl group (for example, an alkylsilyl group can be mentioned. The alkyl group in the alkylsilyl group may be any of linear, branched and cyclic. And, the number of carbon atoms is preferably 1 to 4, and more preferably 1.).

[0141] A 1 It may or may not indicate aromaticity.

[0142] A 1 It may be a monocyclic structure or a condensed ring structure, and is preferably a 5-membered ring, a 6-membered ring, or a condensed ring containing at least one of a 5-membered ring and a 6-membered ring. The number of rings forming the condensed ring is preferably 1 to 4, and more preferably 1 to 3.

[0143] As A 1 The ring represented is usually preferably a ring used as an acidic core (specifically, a merocyanine dye and an acidic core), and specific examples thereof include the following.

[0144] (a) 1,3-dicarbonyl nucleus: for example, 1,3-indanedione nucleus, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione and 1,3-dioxane-4,6-dione.

[0145] (b) Pyrazolone nucleus: for example, 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one and 1-(2-benzothiazole)-3-methyl-2-pyrazolin-5-one.

[0146] (c) Isoxazolinone nucleus: for example, 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one.

[0147] (d) Oxindole nucleus: for example, 1-alkyl-2,3-dihydro-2-oxindole, etc.

[0148] (e) 2,4,6-triketohexahydropyrimidine nucleus: for example, barbituric acid, 2-thiobarbituric acid and derivatives thereof. Examples of the derivatives include 1-alkyl groups such as 1-methyl and 1-ethyl, 1,3-dialkyl groups such as 1,3-dimethyl, 1,3-diethyl and 1,3-dibutyl, 1,3-diaryl groups such as 1,3-diphenyl, 1,3-di(p-chlorophenyl) and 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1-aryl groups such as 1-ethyl-3-phenyl, and 1,3-di(2-pyridyl) and other 1,3-diheteroaryl groups such as 1,3-di(2-pyridyl).

[0149] (f) 2-thioxo-2,4-thiazolidinedione nucleus: for example, rhodanine and its derivatives. Examples of the derivatives include 3-alkyl rhodanine such as 3-methyl rhodanine, 3-ethyl rhodanine and 3-allyl rhodanine, 3-aryl rhodanine such as 3-phenyl rhodanine, and 3-heteroaryl rhodanine such as 3-(2-pyridyl) rhodanine.

[0150] (g) 2-Thioxo-2,4-oxazolidinedione core (2-thioxo-2,4-(3H,5H)-oxazolidinedione core): for example, 3-ethyl-2-thioxo-2,4-oxazolidinedione and the like.

[0151] (h) Thioindanone nucleus: for example, 3(2H)-thioindanone-1,1-dioxide, etc.

[0152] (i) 2-thioxo-2,5-thiazolidinedione core: for example, 3-ethyl-2-thioxo-2,5-thiazolidinedione and the like.

[0153] (j) 2,4-thiazolidinedione nucleus: for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione.

[0154] (k) Thiazolin-4-one nucleus: for example, 4-thiazolinone and 2-ethyl-4-thiazolinone.

[0155] (l) 2,4-imidazolidinedione (hydantoin) core: for example, 2,4-imidazolidinedione and 3-ethyl-2,4-imidazolidinedione.

[0156] (m) 2-thio-2,4-imidazolidinedione (2-thiohydantoin) core: for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidinedione.

[0157] (n) Imidazolin-5-one core: for example, 2-propylmercapto-2-imidazolin-5-one and the like.

[0158] (o) 3,5-pyrazolidinedione nucleus: for example, 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione.

[0159] (p) Benzothiophene-3(2H)-one nucleus: for example, benzothiophene-3(2H)-one, oxybenzothiophene-3(2H)-one and dioxybenzothiophene-3(2H)-one.

[0160] (q) Indanone nucleus: for example, 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone and 3,3-dimethyl-1-indanone.

[0161] (r) benzofuran-3-(2H)-one nucleus: for example, benzofuran-3-(2H)-one and the like.

[0162] (s) 2,2-dihydro-1,3-dione nucleus, etc.

[0163] A 1 It may be a ring having a group represented by formula (AW).

[0164] *1-LYZ-*2 (AW)

[0165] In the formula (AW), *1 represents the same as -C (=Z) as indicated in the formula (1-1) (or the formula (1-1a)). 1 )-. *2 represents the bonding position to the carbon atom marked with * in formula (1-1) (in other words, *2 represents the bonding position to the carbon atom marked with * in formula (1) 1 The directly bonded carbon atoms together form the bonding position of the carbon atoms that form the double bond).

[0166] That is, when A 1 When Y is a ring having a group represented by formula (AW), 1 The compound represented by the formula (1) (or the compound represented by the formula (1-1a)) which is a group represented by the formula (1-1) is a compound represented by the formula (1-1b).

[0167] In addition, the symbols used in formula (1-1b) have the same meanings as the corresponding symbols used in formula (1).

[0168] [Chemical formula 4]

[0169]

[0170] In formula (AW), L represents a single bond or -NR L -.

[0171] R L represents a hydrogen atom or a substituent.L It is preferably an alkyl group, an aryl group, or a heteroaryl group, and is preferably an alkyl group or an aryl group.

[0172] L is preferably a single bond.

[0173] Y stands for -CR Y1 =CR Y2 -、-CS-NR Y3 -、-CO-、-CS-、-NR Y4 -、-N=CR Y5 -, or 1,8-naphthalenediyl which may have a substituent, among which -CR Y1 =CR Y2 -.

[0174] R Y1 ~R Y5 Each independently represents a hydrogen atom or a substituent. Among them, R Y1 ~R Y5 are each independently alkyl, aryl or heteroaryl.

[0175] And, when Y represents -CR Y1 =CR Y2 -, preferably R Y1 With R Y2 bonded to each other to form a ring, as R Y1 With R Y2 Examples of the ring formed by mutually bonding include aromatic rings (aromatic hydrocarbon rings and aromatic heterocyclic rings), and specific examples include benzene rings and pyridine rings. Y1 With R Y2 The ring formed by bonding to each other may further have a substituent, and such substituents may bond to each other to form a ring.

[0176] Z represents a single bond, -CO-, -S-, -SO2- or -CR Z1 =CR Z2 -, among which -CO- is preferred.

[0177] R Z1 and R Z2 Each independently represents a hydrogen atom or a substituent.

[0178] In addition, the combination of L, Y and Z is preferably a combination in which -LYZ- and the two carbon atoms indicated in formula (1-1) are bonded to form a 5-membered ring or a 6-membered ring. As mentioned above, the 5-membered ring or the 6-membered ring may be further fused with a different ring (preferably a benzene ring) to form a fused ring structure.

[0179] Among them, from the viewpoint of better heat resistance of the photoelectric conversion element, A 1It is preferably a ring having a group represented by formula (AX).

[0180] [Chemical formula 5]

[0181]

[0182] In the formula (AX), *1 and *2 have the same definitions as *1 and *2 in the formula (AW), respectively.

[0183] R 7 and R 8 Each independently represents a hydrogen atom or a substituent.

[0184] Preferably R 7 With R 8 bonded to each other to form a ring, as R 7 With R 8 Examples of the ring formed by mutually bonding include aromatic rings (aromatic hydrocarbon rings and aromatic heterocyclic rings), and specific examples include a benzene ring, a pyrazine ring, and a pyridine ring.

[0185] R 7 With R 8 The ring formed by mutually bonding preferably further has a substituent. The substituent is preferably a halogen atom, more preferably a chlorine atom.

[0186] And, R 7 With R 8 Substituents on the ring formed by bonding to each other may further bond to each other to form a ring (such as a benzene ring).

[0187] From the viewpoint of achieving more excellent heat resistance of the photoelectric conversion element, the group represented by formula (AX) is preferably a group represented by the following formula (AY).

[0188] [Chemical formula 6]

[0189]

[0190] In the formula (AY), *1 and *2 have the same meanings as *1 and *2 in the formula (AX), respectively.

[0191] R 9 ~R 12 Each independently represents a hydrogen atom or a substituent. Among them, R 9 ~R 12 Each is independently a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a chlorine atom.

[0192] R 9 With R 10 Can bond to each other to form a ring, R 10 With R 11Can bond to each other to form a ring, R 11 With R 12 They may be bonded to each other to form a ring. 9 With R 10 , R 10 With R 11 and R 11 With R 12 Examples of the ring formed by mutually bonding include aromatic rings (aromatic hydrocarbon rings and aromatic heterocyclic rings), and specifically, a benzene ring is preferred.

[0193] Among them, R is preferred 10 With R 11 They are bonded to each other to form a ring.

[0194] In addition, R 9 With R 10 , R 10 With R 11 and R 11 With R 12 The rings formed by the mutual bonding may be further substituted with substituents. The substituents on the rings may be further bonded to each other to form a ring. And, if possible, the substituents on the rings are 9 ~R 12 One or more of them may be bonded to each other to further form one or more rings.

[0195] Furthermore, a group formed by mutual bonding of substituents possessed by a ring may be a single bond.

[0196] In formula (1-1), Z 1 represents an oxygen atom, a sulfur atom, =NR Z1 or =CR Z2 R Z3 .

[0197] R Z1 represents a hydrogen atom or a substituent. Z2 and R Z3 Each independently represents a cyano group or a -COOR Z4 . R Z4 It 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.

[0198] Z 1 Preferred is an oxygen atom.

[0199] In formula (1-2), R b1 and R b2 Each independently represents a cyano group or a -COOR b3 .

[0200] R b3It represents an alkyl group which may have a substituent, an aryl group (such as a phenyl group) which may have a substituent, or a heteroaryl group which may have a substituent.

[0201] In formula (1), R 1 and R 2 Each independently represents a hydrogen atom or a substituent.

[0202] Preferred R 1 and R 2 are each independently a hydrogen atom.

[0203] In formula (1), R a1 and R a2 Each independently represents an aryl group which may have a substituent, -C(R L1 )(R L2 )(R L3 ), or a heteroaryl group which may have a substituent.

[0204] The aryl group is preferably a phenyl group, a naphthyl group, or a fluorenyl group, and more preferably a phenyl group or a naphthyl group.

[0205] When the aryl group is a phenyl group, the phenyl group preferably has a substituent, and the substituents are preferably each independently an alkyl group (preferably having 1 to 3 carbon atoms).

[0206] When the aryl group is a phenyl group, the number of substituents that the phenyl group has is preferably 1 to 5, more preferably 2 or 3.

[0207] -C(R L1 )(R L2 )(R L3 ) L1 ~R L3 Each independently represents an alkyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or a hydrogen atom, and R L1 ~R L3 At least two of them 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. L1 ~R L3 The alkyl group which may have a substituent, the aryl group which may have a substituent, and the heteroaryl group which may have a substituent may be bonded to each other to form a ring.

[0208] For example, the alkyl groups which may have a substituent may be bonded to each other to form a ring. The substituent in the aryl group which may have a substituent and the alkyl group which may have a substituent may be bonded to each other to form a ring. The substituent in the heteroaryl group which may have a substituent and the alkyl group which may have a substituent may be bonded to each other to form a ring. The substituent in the aryl group which may have a substituent and the substituent in another aryl group which may have a substituent may be bonded to each other to form a ring. The substituent in the aryl group which may have a substituent and the substituent in the heteroaryl group which may have a substituent may be bonded to each other to form a ring. The substituent in the heteroaryl group which may have a substituent and the substituent in another heteroaryl group which may have a substituent may be bonded to each other to form a ring.

[0209] The substituent in the ring formed in this manner may bond to another alkyl group which may have a substituent, a substituent in another aryl group which may have a substituent, or a substituent in another heteroaryl group which may have a substituent to further form a ring.

[0210] In addition, as described above, a group formed by a bond between substituents (for example, a substituent in an aryl group which may have a substituent and a substituent in a heteroaryl group which may have a substituent) may be a single bond.

[0211] In addition, R L1 ~R L3 When the alkyl group which may have a substituent, the aryl group which may have a substituent and the heteroaryl group which may have a substituent are bonded to each other to form a ring, -C(R L1 )(R L2 )(R L3 ) is preferably a group other than an aryl group and a heteroaryl group.

[0212] R L1 ~R L3 The alkyl groups represented by R may be linear, branched or cyclic. L1 ~R L3 Among the alkyl groups represented by , two alkyl groups may be bonded to each other to form a ring.

[0213] More specifically, for example, R L1 The alkyl group represented by R L2 The alkyl groups represented by may be bonded to each other to form a ring. L1 The alkyl group represented by R L2 The substituents possessed by the ring (monocyclic cycloalkane ring, etc.) formed by mutually bonding the alkyl groups represented by L3 The alkyl groups represented may be bonded to each other to form a polycyclic ring (polycyclic cycloalkane ring, etc.).

[0214] That is, -C(R L1 )(RL2 )(R L3 ) may be a cycloalkyl group (preferably a cyclohexyl group) which may have a substituent. The number of ring members in the cycloalkyl group is preferably 3 to 12, more preferably 5 to 8, and even more preferably 6.

[0215] The cycloalkyl group may be a monocyclic group (such as cyclohexyl) or a polycyclic group (such as 1-adamantyl).

[0216] The cycloalkyl group preferably has a substituent. When the cycloalkyl group has a substituent, it is preferably a carbon atom directly bonded to the nitrogen atom indicated in the general formula (1) (i.e., "-C(R L1 )(R L2 )(R L3 )" has a substituent on a carbon atom adjacent to the carbon atom adjacent to the "C" atom indicated in the above description.

[0217] Examples of the substituent that the cycloalkyl group may have include an alkyl group (preferably having 1 to 3 carbon atoms).

[0218] The substituents of the cycloalkyl group may be bonded to each other to form a ring, and the ring formed by the substituents may be a ring other than a cycloalkane ring.

[0219] From the viewpoint of better heat resistance of the photoelectric conversion element, R a1 and R a2 each independently represents a group represented by formula (X), -C(R L1 )(R L2 )(R L3 ), a polycyclic aryl group which may have a substituent, or a polycyclic heteroaryl group which may have a substituent.

[0220] Among them, from the viewpoint that the half width of the absorption peak of the photoelectric conversion element can be narrowed, R a1 and R a2 are independently a group represented by the formula (X), -C(R L1 )(R L2 )(R L3 ), or a polycyclic aryl group which may have a substituent. The group represented by formula (X) is preferably a group represented by formula (Z) described below, and more preferably a group represented by formula (ZB) described below.

[0221] In a stacked imaging element in which a plurality of photoelectric conversion elements receiving different types of light are stacked, when light enters the imaging element, the photoelectric conversion element arranged on the incident side absorbs a portion of the incident light, and the transmitted light is absorbed by the photoelectric conversion element arranged further inside. In such an imaging element, the narrower the half width of the absorption peak of each photoelectric conversion element, the easier it is to perform color separation, and therefore it is preferred.

[0222] The groups represented by formula (X) are the groups shown below.

[0223] [Chemical formula 7]

[0224]

[0225] In formula (X), B 1 In addition to R d1 In addition, it represents a monocyclic aromatic ring which may have a substituent.

[0226] R d1 represents an alkyl group, a silyl group, an alkoxy group, an alkylthio group, a cyano group, a halogen atom, an aryl group, a heteroaryl group, an alkenyl group, or an alkynyl group.

[0227] These groups may further have a substituent, if possible.

[0228] As the monocyclic aromatic ring, monocyclic aromatic hydrocarbon rings and monocyclic aromatic heterocyclic rings can be mentioned. As the aromatic hydrocarbon ring, for example, a benzene ring can be mentioned. As the aromatic heterocyclic ring, for example, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring and an oxazole ring can be mentioned.

[0229] Among them, from the viewpoint of further improving the heat resistance of the photoelectric conversion element, an aromatic hydrocarbon ring is preferred, and a benzene ring is more preferred.

[0230] As R d1 The number of carbon atoms in the alkyl group represented by is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 3. Furthermore, the alkyl group is preferably -CH(R d3 )(R d4 ), or -C(R d3 )(R d4 )(R d5 ). d3 ~R d5 Each independently represents an aryl group, an alkyl group (preferably having 1 to 3 carbon atoms) or a heteroaryl group, and is preferably an alkyl group.

[0231] As R d1 The silyl group represented by is, for example, preferably -Si(R p )(R q )(R r ) represented by R p ~R r Each independently represents a hydrogen atom or a substituent. p ~R rExamples of the substituents represented include alkyl groups (which may be linear, branched or cyclic, and preferably have 1 to 4 carbon atoms, more preferably 1), aryl groups and heteroaryl groups. These groups may further have substituents.

[0232] As R d1 The number of carbon atoms of the alkoxy group represented is preferably 1-12, more preferably 1-6, and even more preferably 1-3.

[0233] As R d1 The number of carbon atoms of the alkylthio group represented is preferably 1-12, more preferably 1-6, and even more preferably 1-3.

[0234] As R d1 Examples of the halogen atom include a fluorine atom, an iodine atom, a bromine atom and a chlorine atom.

[0235] As R d1 Examples of the aryl group represented by include the aryl group AR described later.

[0236] As R d1 Examples of the heteroaryl group represented by include the heteroaryl group HA described later.

[0237] As R d1 The number of carbon atoms of the alkenyl group represented is preferably 2-12, more preferably 2-6, and even more preferably 2-3.

[0238] As R d1 The number of carbon atoms of the alkynyl group represented is preferably 2-12, more preferably 2-6, and even more preferably 2-3.

[0239] R d1 With B 1 The substituents may be bonded to each other to form a non-aromatic ring.

[0240] * indicates bonding position. B 1 The aromatic ring of is directly bonded to the nitrogen atom indicated in formula (1).

[0241] The group represented by formula (X) is preferably a group represented by formula (Z).

[0242] [Chemical formula 8]

[0243]

[0244] In formula (Z), T 1 ~T 4 Respectively represent -CR e12 = or nitrogen atom (=N-). e12 represents a hydrogen atom or a substituent.

[0245] Preferably "T 1 ~T 4 At least one of the following indicates -CR e12 =, and R e12 At least one of them represents a substituent", more preferably "at least T 4 Indicates -CR e12 =, and R e12 represents an alkyl group, an aryl group or a heteroaryl group", and more preferably "at least T 4 Indicates -CR e12 =, and R e12 Yes -CH(R d3 )(R d4 ), or -C(R d3 )(R d4 )(R d5 )”.

[0246] Regarding the above-mentioned -CH(R d3 )(R d4 ) and the above-C(R d3 )(R d4 )(R d5 ) as described below.

[0247] The definition of the substituent is the same as the meaning of the substituent W described later. As the substituent, for example, an alkyl group, an aryl group, a heteroaryl group, a silyl group, a halogen atom, and a cyano group can be mentioned. In addition, these groups may also have a substituent (for example, a halogen atom such as a fluorine atom can be mentioned.).

[0248] As R e12 The number of carbon atoms in the alkyl group represented by is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 3. Furthermore, the alkyl group is preferably -CH(R d3 )(R d4 ), or -C(R d3 )(R d4 )(R d5 ). d3 ~R d5 Each independently represents an aryl group, an alkyl group (preferably having 1 to 3 carbon atoms) or a heteroaryl group, and is preferably an alkyl group.

[0249] As R e12 Examples of the aryl group represented by include the aryl group AR described later.

[0250] As R e12 Examples of the heteroaryl group represented by include the heteroaryl group HA described later.

[0251] As R e12 The silyl group represented by can be exemplified as R d1The silyl group described is based on the silyl group represented by FIG.

[0252] As R e12 Examples of the halogen atom represented by include a fluorine atom, an iodine atom, a bromine atom and a chlorine atom.

[0253] Furthermore, when R in formula (Z) e12 When there are multiple e12 They can be the same as each other or different.

[0254] In formula (Z), R f2 represents an alkyl group, a silyl group, an alkoxy group, an alkylthio group, a cyano group, a halogen atom, an aryl group, a heteroaryl group, an alkenyl group, or an alkynyl group, and R in formula (X) d1 The meanings are the same and the preferred conditions are also the same.

[0255] And, R f2 With T 1 R e12 They can bond to each other to form non-aromatic rings.

[0256] As the group represented by formula (X), a group represented by formula (ZB) is more preferred.

[0257] [Chemical formula 9]

[0258]

[0259] In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom. e12 represents a hydrogen atom or a substituent.

[0260] R in formula (ZB) e12 and R in formula (Z) e12 same.

[0261] In formula (ZB), R f3 and R f4 R each independently represents an alkyl group, an aryl group, or a heteroaryl group. f3 and R f4 One or both of them are preferably -CH(R d3 )(R d4 )、-C(R d3 )(R d4 )(R d5 ), aryl, or heteroaryl. d3 ~R d5 Each independently represents an aryl group, an alkyl group (preferably having 1 to 3 carbon atoms) or a heteroaryl group, and is preferably an alkyl group.

[0262] These groups may further have a substituent, if possible.

[0263] *Indicates bonding position.

[0264] The number of rings constituting the polycyclic aryl group which may have a substituent and the polycyclic heteroaryl group which may have a substituent is 2 or more, preferably 2 to 4, more preferably 2 to 3, and even more preferably 2.

[0265] The substituent that the polycyclic aryl group which may have a substituent and the polycyclic heteroaryl group which may have a substituent may include a non-aromatic ring.

[0266] As the polycyclic aryl group which may have a substituent, for example, a naphthyl group which may have a substituent is preferable.

[0267] In formula (1), Ar 1 It represents an aromatic ring which may have a substituent.

[0268] The aromatic ring may be a single ring or multiple rings.

[0269] As the aromatic ring, an aromatic hydrocarbon ring and an aromatic heterocyclic ring can be mentioned. As the aromatic hydrocarbon ring, for example, a benzene ring, a naphthalene ring, an anthracene ring and a phenanthrene ring can be mentioned. As the aromatic heterocyclic ring, for example, a quinoxaline ring, a pyrazine ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring and an oxazole ring can be mentioned. These rings can be further condensed with other rings (which can be non-aromatic rings).

[0270] Among them, Ar 1 It is preferably an aromatic heterocyclic ring, and more preferably a quinoxaline ring or a pyrazine ring.

[0271] As Ar 1 The substituent of the aromatic ring represented by is preferably an alkyl group.

[0272] (Formula (2))

[0273] From the viewpoint of achieving more excellent heat resistance of the photoelectric conversion element, the specific compound is preferably a compound represented by formula (2).

[0274] [Chemical formula 10]

[0275]

[0276] A in formula (2) 1 and A in formula (1-1) (or formula (1-1a)) 1 The meanings are the same and the preferred conditions are also the same.

[0277] R in formula (2) 1 and R 2 With R in formula (1) 1 and R2 The meanings are the same and the preferred conditions are also the same.

[0278] R in formula (2) a1 and R a2 With R in formula (1) a1 and R a2 The meanings are the same and the preferred conditions are also the same.

[0279] X 1 ~X 4 Each independently represents a nitrogen atom (-N=) or -CR c1 =.

[0280] R c1 represents a hydrogen atom or a substituent.

[0281] X 1 ~X 4 Preferably, at least 2 of them are nitrogen atoms, and more preferably at least X 1 and X 4 is a nitrogen atom, more preferably only X 1 and X 4 It's a nitrogen atom.

[0282] When R c1 When there are multiple, there are multiple R c1 They may be bonded to each other to form a ring. c1 The ring formed by mutually bonding is preferably an aromatic ring, more preferably a benzene ring or a pyridine ring. c1 The ring formed by bonding to each other may further have a substituent.

[0283] (Formula (3))

[0284] From the viewpoint of further improving the heat resistance of the photoelectric conversion element, the specific compound is more preferably a compound represented by formula (3).

[0285] [Chemical formula 11]

[0286]

[0287] A in formula (3) 1 and A in formula (1-1) (or formula (1-1a)) 1 The meanings are the same and the preferred conditions are also the same.

[0288] R in formula (3) 1 and R 2 With R in formula (1) 1 and R 2 The meanings are the same and the preferred conditions are also the same.

[0289] E3 Represents a nitrogen atom (-N=) or -CR 3 =.

[0290] E 6 Represents a nitrogen atom (-N=) or -CR 6 =.

[0291] E 3 and E 6 Preferably "E 3 Yes-CR 3 =, E 6 Yes-CR 6 ='s form", "E 3 Yes-N=,E 6 Yes-CR 6 = form", or "E 3 Yes-CR 3 =, E 6 It is -N=", more preferably "E 3 Yes-CR 3 =, E 6 Yes-CR 6 = form".

[0292] R 3 ~R 6 Each independently represents a hydrogen atom or a substituent.

[0293] Preferred R 3 ~R 6 Each of R is independently a hydrogen atom, an alkoxy group, a silyl group, or an alkyl group, and more preferably a hydrogen atom, an alkoxy group having 1 to 3 carbon atoms in the alkyl part, or an alkyl group having 1 to 4 carbon atoms. 3 ~R 6 In the formula, R represents a substituent. 3 ~R 6 The number of is preferably 0 to 2. 3 ~R 6 When one or more of the substituents represent substituents, preferably R 4 and / or R 5 represents a substituent.

[0294] When E 3 Yes-CR 3 =R 3 With R 4 , R 4 With R 5 and E 6 Yes-CR 6 =R 5 With R 6 Each of R independently may be bonded to each other to form a ring. 3 With R 4, R 4 With R 5 and R 5 With R 6 The ring formed by mutually bonding may be a monocyclic ring or a polycyclic ring, may be aromatic or non-aromatic, and may have a substituent.

[0295] R in formula (3) a1 and R a2 With R in formula (1) a1 and R a2 The meanings are the same and the preferred conditions are also the same.

[0296] (Formula (4))

[0297] From the viewpoint of further improving the heat resistance of the photoelectric conversion element, the specific compound is more preferably a compound represented by formula (4).

[0298] [Chemical formula 12]

[0299]

[0300] R in formula (4) 1 and R 2 With R in formula (1) 1 and R 2 The meanings are the same and the preferred conditions are also the same.

[0301] E in formula (4) 3 and E 6 With E in formula (3) 3 and E 6 The meanings are the same and the preferred conditions are also the same.

[0302] R in formula (4) 3 ~R 6 With R in formula (3) 3 ~R 6 The meanings are the same and the preferred conditions are also the same.

[0303] R in formula (4) 7 and R 8 and R in formula (AX) 7 and R 8 The meanings are the same and the preferred conditions are also the same.

[0304] R in formula (4) a1 and R a2 With R in formula (1) a1 and R a2 The meanings are the same and the preferred conditions are also the same.

[0305] (Formula (4-2))

[0306] One of the preferred embodiments of the compound represented by formula (4) is a compound represented by formula (4-2).

[0307] [Chemical formula 13]

[0308]

[0309] R in formula (4-2) 1 and R 2 With R in formula (1) 1 and R 2 The meanings are the same and the preferred conditions are also the same.

[0310] E in formula (4-2) 3 and E 6 With E in formula (3) 3 and E 6 The meanings are the same and the preferred conditions are also the same.

[0311] R in formula (4-2) 3 ~R 6 With R in formula (3) 3 ~R 6 The meanings are the same and the preferred conditions are also the same.

[0312] R in formula (4-2) 7 and R 8 and R in formula (AX) 7 and R 8 The meanings are the same and the preferred conditions are also the same.

[0313] R in formula (4-2) a3 and R a4 each independently represents a group represented by formula (X), -C(R L1 )(R L2 )(R L3 ), a polycyclic aryl group which may have a substituent, or a polycyclic heteroaryl group which may have a substituent.

[0314] R in formula (4-2) a3 and R a4 The group represented by the formula (X) in -C(R L1 )(R L2 )(R L3 ), a polycyclic aryl group which may have a substituent, and a polycyclic heteroaryl group which may have a substituent are respectively related to R in formula (1) a1 and R a2 The group represented by the formula (X) described above, -C(R L1 )(R L2 )(R L3), a polycyclic aryl group which may have a substituent, and a polycyclic heteroaryl group which may have a substituent have the same meanings and the preferred conditions are also the same.

[0315] (Formula (5))

[0316] From the viewpoint of achieving more excellent heat resistance of the photoelectric conversion element, the specific compound is particularly preferably a compound represented by formula (5).

[0317] [Chemical formula 14]

[0318]

[0319] R in formula (5) 1 and R 2 With R in formula (1) 1 and R 2 The meanings are the same and the preferred conditions are also the same.

[0320] E in formula (5) 3 and E 6 With E in formula (3) 3 and E 6 The meanings are the same and the preferred conditions are also the same.

[0321] R in formula (5) 3 ~R 6 With R in formula (3) 3 ~R 6 The meanings are the same and the preferred conditions are also the same.

[0322] R in formula (5) 9 ~R 12 and R in formula (AY) 9 ~R 12 The meanings are the same and the preferred conditions are also the same.

[0323] R in formula (5) a1 and R a2 With R in formula (1) a1 and R a2 The meanings are the same and the preferred conditions are also the same.

[0324] (Substituent W)

[0325] The substituent W in this specification is described.

[0326] Examples of the substituent W include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group, an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, an aryl group, a heterocyclic group (which may be referred to as a heteroatom-containing cyclic group, including a heteroaryl group), a cyano group, a hydroxyl group, a nitro group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), an ammonium group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl group or arylsulfonylamino, thiol, alkylthio, arylthio, heterocyclic thio, sulfamoyl, alkyl or arylsulfinyl, alkyl or arylsulfonyl, acyl, aryloxycarbonyl, alkoxycarbonyl, carbamoyl, aryl or heterocyclic azo, imido, phosphino, phosphinyl, phosphinyloxy, phosphinylamino, phosphonyl, silyl, hydrazine, urea, boric acid (-B(OH)2), sulfo, carboxyl, phosphate, phosphonyl, phosphoryl, monosulfate, monophosphate, phosphonic acid, phosphino acid, boric acid and other well-known substituents.

[0327] Furthermore, the substituent W may be further substituted by a substituent W. For example, the alkyl group may be substituted by a halogen atom.

[0328] The details of the substituent W are described in paragraph

[0023] of JP-A-2007-234651.

[0329] (Alkyl AL)

[0330] The alkyl group AL preferably has, for example, 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 6 carbon atoms. The alkyl group may be linear, branched, or cyclic.

[0331] Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-hexyl group, and a cyclopentyl group.

[0332] Furthermore, the alkyl group may be, for example, a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have these cyclic structures as a partial structure.

[0333] There are no particular restrictions on the substituents that the alkyl group may have, and preferred examples include the substituent W, an aryl group (preferably having 6 to 18 carbon atoms, more preferably 6 carbon atoms), a heteroaryl group (preferably having 5 to 18 carbon atoms, more preferably 5 to 6 carbon atoms) or a halogen atom (preferably a fluorine atom or a chlorine atom).

[0334] (Aryl AR)

[0335] Examples of the aryl group AR include aryl groups having 6 to 18 carbon atoms.

[0336] The aryl group may be a single ring or a polycyclic ring.

[0337] As the aryl group, for example, a phenyl group, a naphthyl group, an anthryl group, or a fluorenyl group is preferred, and a phenyl group is more preferred.

[0338] The substituent that the aryl group may have is not particularly limited, and examples thereof include the substituent W. Among them, the substituent is more preferably an alkyl group (preferably having 1 to 10 carbon atoms) that may have a substituent, and more preferably a methyl group or an isopropyl group.

[0339] (Heteroaryl HA)

[0340] Examples of the heteroaryl group HA include heteroaryl groups having a monocyclic or polycyclic ring structure containing a hetero atom such as a sulfur atom, an oxygen atom, or a nitrogen atom.

[0341] The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably 3-18, and more preferably 3-5.

[0342] The number of hetero atoms contained in the heteroaryl group is not particularly limited, but is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 to 2.

[0343] The number of ring members of the heteroaryl group is not particularly limited, but is preferably 3-8, more preferably 5-7, and even more preferably 5-6.

[0344] Examples of the heteroaryl group include a furanyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a pteridinyl group, a pyrazinyl group, a quinoxalinyl group, a pyrimidinyl group, a quinazolinyl group, a pyridazinyl group, a cinnolinyl group, a phthalazinyl group, a triazinyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, an imidazolyl group, a benzimidazolyl group, a pyrazolyl group, an indazolyl group, an isoxazolyl group, a benzisoxazolyl group, an isothiazolyl group, a benzisothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, a benzofuranyl group, a thienyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a pyrrolyl group, an indolyl group, an imidazopyridinyl group, and a carbazolyl group.

[0345] The substituent that the heteroaryl group may have is not particularly limited, and examples thereof include the substituent W.

[0346] Specific compounds are exemplified below.

[0347] In addition, when the specific compounds exemplified below are applied to formula (1), the following descriptions are provided regarding the 1The specific compounds exemplified below include any of the geometrical isomers differentiated by the C=C double bond between the bonded carbon atom and the adjacent carbon atom. That is, both the cis-isomer and the trans-isomer differentiated by the C=C double bond are included in the specific compounds exemplified below.

[0348] In the following examples, Me represents a methyl group, and Ph represents a phenyl group.

[0349] [Chemical formula 15]

[0350]

[0351] [Chemical formula 16]

[0352]

[0353] [Chemical formula 17]

[0354]

[0355] [Chemical formula 18]

[0356]

[0357] [Chemical formula 19]

[0358]

[0359] [Chemical formula 20]

[0360]

[0361] [Chemical formula 21]

[0362]

[0363] [Chemical formula 22]

[0364]

[0365] [Chemical formula 23]

[0366]

[0367] [Chemical formula 24]

[0368]

[0369] [Chemical formula 25]

[0370]

[0371] [Chemical formula 26]

[0372]

[0373] The R X1 ~R X14 and A x1 Examples of combinations of forms that the groups of are able to take are shown in the following table.

[0374] In addition, in the table, Me represents a methyl group, MeO represents a methoxy group, Et represents an ethyl group, iPr represents an isopropyl group, and tBu represents a tert-butyl group.

[0375] In addition, in the table, the details of the groups represented by "A-number" or "S-number" will be further described in the following paragraphs.

[0376] [Table 1]

[0377] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 1 H H H H Me H H H Me Me H H H Me A-2 2 H H H H Me H Me H Me Me H Me H Me A-2 3 H H H H Me Me Me Me Me Me Me Me Me Me A-2 4 H H H H E H H H E E H H H E A-2 5 H H H H Me H H H tBu Me H H H tBu A-2 6 H H H H E H Me H E E H Me H E A-2 7 H H H H tBu H tBu H tBu tBu H tBu H tBu A-2 8 H H H H Me H Cl H Me Me H Cl H Me A-2 9 H H H H Me H Br H Me Me H Br H Me A-2 10 H H H H Me H S-1 H Me Me H S-1 H Me A-2 11 H H H H i H H H i i H H H i A-2 12 F H H H i H H H i i H H H i A-2 13 H F H H i H H H i i H H H i A-2 14 H F F H i H H H i i H H H i A-2 15 Me F H H i H H H i i H H H i A-2 16 H F Me H i H H H i i H H H i A-2 17 H F H Me i H H H i i H H H i A-2 18 H F Cl H i H H H i i H H H i A-2 19 F H Cl H i H H H i i H H H i A-2 20 Cl H H H i H H H i i H H H i A-2 21 H Cl H H i H H H i i H H H i A-2 22 H Cl Cl H i H H H i i H H H i A-2 23 H Me H H i H H H i i H H H i A-2 24 Me H H H i H H H i i H H H i A-2 25 H Me Me H i H H H i i H H H i A-2 26 H MeO H H i H H H i i H H H i A-2 27 H tBu H H i H H H i i H H H i A-2 28 H S-1 H H i H H H i i H H H i A-2 29 H S-8 H H i H H H i i H H H i A-2 30 H S-14 H H i H H H i i H H H i A-2 31 H S-31 H H i H H H i i H H H i A-2 32 H S-44 H H i H H H i i H H H i A-2 33 H S-47 H H i H H H i i H H H i A-2 34 H S-61 H H i H H H i i H H H i A-2 35 H S-79 H H i H H H i i H H H i A-2 36 H S-81 H H i H H H i i H H H i A-2 37 H S-95 H H i H H H i i H H H i A-2 38 H S-98 H H i H H H i i H H H i A-2 39 H S-102 H H i H H H i i H H H i A-2 40 S-1 H H H i H H H i i H H H i A-2

[0378] [Table 2]

[0379] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 41 S-8 H H H i H H H i i H H H i A-2 42 S-14 H H H i H H H i i H H H i A-2 43 S-31 H H H i H H H i i H H H i A-2 44 S-44 H H H i H H H i i H H H i A-2 45 S-47 H H H i H H H i i H H H i A-2 46 S-61 H H H i H H H i i H H H i A-2 47 S-79 H H H i H H H i i H H H i A-2 48 S-81 H H H i H H H i i H H H i A-2 49 S-95 H H H i H H H i i H H H i A-2 50 S-98 H H H i H H H i i H H H i A-2 51 S-102 H H H i H H H i i H H H i A-2 52 H H H H i H H H i i H H H i A-1 53 H H H H i H H H i i H H H i A-3 54 H H H H i H H H i i H H H i A-4 55 H H H H i H H H i i H H H i A-5 56 H H H H i H H H i i H H H i A-6 57 H H H H i H H H i i H H H i A-7 58 H H H H i H H H i i H H H i A-8 59 H H H H i H H H i i H H H i A-9 60 H H H H i H H H i i H H H i A-10 61 H H H H i H H H i i H H H i A-11 62 H H H H i H H H i i H H H i A-12 63 H H H H i H H H i i H H H i A-13 64 H H H H i H H H i i H H H i A-14 65 H H H H i H H H i i H H H i A-15 66 H H H H i H H H i i H H H i A-16 67 H H H H i H H H i i H H H i A-17 68 H H H H i H H H i i H H H i A-18 69 H H H H i H H H i i H H H i A-19 70 H H H H i H H H i i H H H i A-20 71 H H H H i H H H i i H H H i A-21 72 H H H H i H H H i i H H H iPr A-22 73 H H H H iPr H H H iPr iPr H H H iPr A-23 74 H H H H iPr H H H iPr iPr H H H iPr A-24 75 H H H H iPr H H H iPr iPr H H H iPr A-25 76 H H H H iPr H H H iPr iPr H H H iPr A-26 77 H H H H iPr H H H iPr iPr H H H iPr A-27 78 H H H H iPr H H H iPr iPr H H H iPr A-28 79 H H H H iPr H H H iPr iPr H H H iPr A-29 80 H H H H iPr H H H iPr iPr H H H iPr A-36

[0380] [Table 3]

[0381] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 81 H H H H iPr H H H iPr iPr H H H iPr A-37 82 H H H H iPr H H H iPr iPr H H H iPr A-40 83 H Cl H H iPr H H H iPr iPr H H H iPr A-5 84 H Cl H H iPr H H H iPr iPr H H H iPr A-6 85 H Cl H H iPr H H H iPr iPr H H H iPr A-7 86 H Cl H H iPr H H H iPr iPr H H H iPr A-8 87 H Cl H H iPr H H H iPr iPr H H H iPr A-10 88 H Cl H H iPr H H H iPr iPr H H H iPr A-11 89 H Cl H H iPr H H H iPr iPr H H H iPr A-12 90 H Cl H H iPr H H H iPr iPr H H H iPr A-28 91 H Cl H H iPr H H H iPr iPr H H H iPr A-31 92 H Cl Cl H iPr H H H iPr iPr H H H iPr A-8 93 H Cl Cl H iPr H H H iPr iPr H H H iPr A-12 94 H Cl Cl H iPr H H H iPr iPr H H H iPr A-17 95 H Me H H iPr H H H iPr iPr H H H iPr A-5 96 H Me H H iPr H H H iPr iPr H H H iPr A-6 97 H Me H H iPr H H H iPr iPr H H H iPr A-8 98 H Me H H iPr H H H iPr iPr H H H iPr A-12 99 H Me H H iPr H H H iPr iPr H H H iPr A-17 100 H tBu H H iPr H H H iPr iPr H H H iPr A-5 101 H tBu H H iPr H H H iPr iPr H H H iPr A-6 102 H tBu H H iPr H H H iPr iPr H H H iPr A-8 103 H tBu H H iPr H H H iPr iPr H H H iPr A-10 104 H tBu H H iPr H H H iPr iPr H H H iPr A-17 105 H Me Me H iPr H H H iPr iPr H H H iPr A-5 106 H Me Me H iPr H H H iPr iPr H H H iPr A-6 107 H Me Me H iPr H H H iPr iPr H H H iPr A-8 108 H Me Me H iPr H H H iPr iPr H H H iPr A-10 109 H Me Me H iPr H H H iPr iPr H H H iPr A-17 110 H F F H iPr H H H iPr iPr H H H iPr A-1 111 H F F H iPr H H H iPr iPr H H H iPr A-5 112 H F F H iPr H H H iPr iPr H H H iPr A-6 113 H F F H iPr H H H iPr iPr H H H iPr A-7 114 H F F H iPr H H H iPr iPr H H H iPr A-8 115 H F F H iPr H H H iPr iPr H H H iPr A-10 116 H F F H iPr H H H iPr iPr H H H iPr A-11 117 H F F H iPr H H H iPr iPr H H H iPr A-12 118 H F F H iPr H H H iPr iPr H H H iPr A-17 119 H H H H iPr H H H iPr S-1 H Me H S-1 A-5 120 H H H H iPr H H H iPr S-2 H Me H S-2 A-5

[0382] [Table 4]

[0383] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 121 H H H H iPr H H H iPr S-3 H Me H S-3 A-5 122 H H H H iPr H H H iPr S-4 H Me H S-4 A-5 123 H H H H iPr H H H iPr S-5 H Me H S-5 A-5 124 H H H H iPr H H H iPr S-6 H Me H S-6 A-5 125 H H H H iPr H H H iPr S-7 H Me H S-7 A-5 126 H F F H iPr H H H iPr S-8 H Me H S-8 A-5 127 H F F H iPr H H H iPr S-9 H Me H S-9 A-5 128 H F F H iPr H H H iPr S-10 H Me H S-10 A-5 129 H F F H iPr H H H iPr S-11 H Me H S-11 A-5 130 H F F H iPr H H H iPr S-12 H Me H S-12 A-5 131 H F F H iPr H H H iPr S-13 H Me H S-13 A-5 132 H H H H iPr H H H iPr S-14 H Me H S-14 A-5 133 H H H H iPr H H H iPr S-15 H Me H S-15 A-5 134 H H H H iPr H H H iPr S-16 H Me H S-16 A-5 135 H H H H iPr H H H iPr S-17 H Me H S-17 A-5 136 H H H H iPr H H H iPr S-18 H Me H S-18 A-5 137 H H H H iPr H H H iPr S-19 H Me H S-19 A-5 138 H H H H iPr H H H iPr S-20 H Me H S-20 A-5 139 H Cl Cl H iPr H H H iPr S-21 H Me H S-21 A-5 140 H Cl Cl H iPr H H H iPr S-22 H Me H S-22 A-10 141 H Cl Cl H iPr H H H iPr S-23 H Me H S-23 A-10 142 H H H H iPr H H H iPr S-24 H Me H S-24 A-10 143 H H H H iPr H H H iPr S-25 H Me H S-25 A-10 144 H Cl Cl H iPr H H H iPr S-26 H Me H S-26 A-10 145 H H H H iPr H H H iPr S-27 H Me H S-27 A-5 146 H H H H iPr H H H iPr S-28 H Me H S-28 A-5 147 H H H H iPr H H H iPr S-29 H Me H S-29 A-5 148 H H H H iPr H H H iPr S-30 H Me H S-30 A-5 149 H H H H iPr H H H iPr S-31 H Me H S-31 A-2 150 H H H H iPr H H H iPr S-32 H Me H S-32 A-2 151 H H H H iPr H H H iPr S-33 H Me H S-33 A-2 152 H H H H iPr H H H iPr S-34 H Me H S-34 A-2 153 H H H H iPr H H H iPr S-35 H Me H S-35 A-2 154 H H H H iPr H H H iPr S-36 H Me H S-36 A-2 155 H H H H iPr H H H iPr S-37 H Me H S-37 A-2 156 H H H H iPr H H H iPr S-38 H Me H S-38 A-2 157 H H H H iPr H H H iPr S-39 H Me H S-39 A-2 158 H H H H iPr H H H iPr S-40 H Me H S-40 A-2 159 H H H H iPr H H H iPr S-41 H Me H S-41 A-2 160 H H H H iPr H H H iPr S-42 H Me H S-42 A-2

[0384] [Table 5]

[0385] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 161 H H H H iPr H H H iPr S-43 H Me H S-43 A-2 162 H H H H iPr H H H iPr S-44 H Me H S-44 A-2 163 H H H H iPr H H H iPr S-45 H Me H S-45 A-2 164 H H H H iPr H H H iPr S-46 H Me H S-46 A-2 165 H H H H iPr H H H iPr S-47 H Me H S-47 A-2 166 H H H H iPr H H H iPr S-48 H Me H S-48 A-2 167 H H H H iPr H H H iPr S-49 H Me H S-49 A-2 168 H H H H iPr H H H iPr S-50 H Me H S-50 A-2 169 H H H H iPr H H H iPr S-51 H Me H S-51 A-2 170 H H H H iPr H H H iPr S-52 H Me H S-52 A-2 171 H H H H iPr H H H iPr S-53 H Me H S-53 A-2 172 H H H H iPr H H H iPr S-54 H Me H S-54 A-2 173 H H H H iPr H H H iPr S-55 H Me H S-55 A-2 174 H H H H iPr H H H iPr S-56 H Me H S-56 A-2 175 H H H H iPr H H H iPr S-57 H Me H S-57 A-2 176 H H H H iPr H H H iPr S-58 H Me H S-58 A-2 177 H H H H iPr H H H iPr S-59 H Me H S-59 A-2 178 H H H H iPr H H H iPr S-60 H Me H S-60 A-2 179 H H H H iPr H H H iPr S-61 H Me H S-61 A-2 180 H H H H iPr H H H iPr S-62 H Me H S-62 A-2 181 H H H H iPr H H H iPr S-63 H Me H S-63 A-2 182 H H H H iPr H H H iPr S-64 H Me H S-64 A-2 183 H H H H iPr H H H iPr S-65 H Me H S-65 A-2 184 H H H H iPr H H H iPr S-66 H Me H S-66 A-2 185 H H H H iPr H H H iPr S-67 H Me H S-67 A-2 186 H H H H iPr H H H iPr S-68 H Me H S-68 A-2 187 H H H H iPr H H H iPr S-69 H Me H S-69 A-2 188 H H H H iPr H H H iPr S-70 H Me H S-70 A-2 189 H H H H iPr H H H iPr S-71 H Me H S-71 A-2 190 H H H H iPr H H H iPr S-72 H Me H S-72 A-2 191 H H H H iPr H H H iPr S-73 H Me H S-73 A-2 192 H H H H iPr H H H iPr S-74 H Me H S-74 A-2 193 H H H H iPr H H H iPr S-75 H Me H S-75 A-2 194 H H H H iPr H H H iPr S-76 H Me H S-76 A-2 195 H H H H iPr H H H iPr S-77 H Me H S-77 A-2 196 H H H H iPr H H H iPr S-78 H Me H S-78 A-2 197 H H H H iPr H H H iPr S-79 H Me H S-79 A-2 198 H H H H iPr H H H iPr S-80 H Me H S-80 A-2 199 H Cl Cl H iPr H H H iPr S-81 H Me H S-81 A-10 200 H Cl Cl H iPr H H H iPr S-82 H Me H S-82 A-10

[0386] [Table 6]

[0387] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 201 H F F H iPr H H H iPr S-83 H Me H S-83 A-5 202 H F F H iPr H H H iPr S-84 H Me H S-84 A-5 203 H F F H iPr H H H iPr S-85 H Me H S-85 A-5 204 H Cl H H iPr H H H iPr S-86 H Me H S-86 A-6 205 H Cl H H iPr H H H iPr S-87 H Me H S-87 A-10 206 H Cl H H iPr H H H iPr S-88 H Me H S-88 A-11 207 H Cl H H iPr H H H iPr S-89 H Me H S-89 A-12 208 H H H H iPr H H H iPr S-90 H Me H S-90 A-2 209 H H H H iPr H H H iPr S-91 H Me H S-91 A-2 210 H H H H iPr H H H iPr S-92 H Me H S-92 A-2 211 H H H H iPr H H H iPr S-93 H Me H S-93 A-2 212 H H H H iPr H H H iPr S-94 H Me H S-94 A-2 213 H H H H iPr H H H iPr S-95 H Me H S-95 A-2 214 H H H H iPr H H H iPr S-96 H Me H S-96 A-2 215 H H H H iPr H H H iPr S-97 H Me H S-97 A-2 216 H H H H iPr H H H iPr S-98 H Me H S-98 A-2 217 H H H H iPr H H H iPr S-99 H Me H S-99 A-2 218 H H H H iPr H H H iPr S-100 H Me H S-100 A-2 219 H H H H iPr H H H iPr S-101 H Me H S-101 A-5 220 H H H H iPr H H H iPr S-102 H Me H S-102 A-6 221 H H H H iPr H H H iPr S-103 H Me H S-103 A-8 222 H H H H iPr H H H iPr S-104 H Me H S-104 A-8 223 Cl H H H iPr H H H iPr S-105 H Me H S-105 A-17 224 F H F H iPr H H H iPr S-106 H Me H S-106 A-5 225 Cl H H H iPr H H H iPr S-107 H Me H S-107 A-6 226 Cl H H H iPr H H H iPr S-108 H Me H S-108 A-8 227 H H H H iPr H H H iPr S-109 H Me H S-109 A-10 228 H H H H iPr H H H iPr S-110 H Me H S-110 A-11 229 H H H H iPr H H H iPr S-111 H Me H S-111 A-2 230 H H H H iPr H H H iPr S-112 H Me H S-112 A-2 231 H H H H iPr H H H iPr S-113 H Me H S-113 A-2 232 H H H H iPr H H H iPr S-114 H Me H S-114 A-2 233 H H H H iPr H H H iPr S-115 H Me H S-115 A-2 234 H H H H iPr H H H iPr S-116 H Me H S-116 A-2 235 H H H H iPr H H H iPr S-117 H Me H S-117 A-2 236 H H H H iPr H H H iPr S-118 H Me H S-118 A-4 237 H Cl H H iPr H H H iPr S-119 H Me H S-119 A-9 238 H Cl Cl H iPr H H H iPr S-120 H Me H S-120 A-1 239 H Me H H iPr H H H iPr S-1 H H H S-1 A-5 240 H Me H H iPr H H H iPr S-4 H H H S-4 A-5

[0388] [Table 7]

[0389]

[0390] [Table 8]

[0391] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 281 H F F H iPr H H H iPr S-20 H Me H S-20 A-10 282 H F F H iPr H H H iPr S-28 H Me H S-28 A-5 283 H F F H iPr H H H iPr S-28 H Me H S-28 A-10 284 H F F H iPr H H H iPr S-37 H Me H S-37 A-2 285 H F F H iPr H H H iPr S-47 H Me H S-47 A-2 286 H F F H iPr H H H iPr S-63 H Me H S-63 A-2 287 H Cl H H iPr H H H iPr S-55 H Me H S-55 A-2 288 Cl H H H iPr H H H iPr S-55 H Me H S-55 A-2 289 H Me H H iPr H H H iPr S-55 H Me H S-55 A-2 290 Me H H H iPr H H H iPr S-55 H Me H S-55 A-2 291 H tBu H H iPr H H H iPr S-31 H Me H S-31 A-2 292 H tBu H H iPr H H H iPr S-37 H Me H S-37 A-2 293 H tBu H H iPr H H H iPr S-40 H Me H S-40 A-2 294 H tBu H H iPr H H H iPr S-47 H Me H S-47 A-2 295 H tBu H H iPr H H H iPr S-63 H Me H S-63 A-2 296 H tBu H H iPr H H H iPr S-90 H Me H S-90 A-2 297 H tBu H H iPr H H H iPr S-94 H Me H S-94 A-2 298 H tBu H H iPr H H H iPr S-95 H Me H S-95 A-2 299 H tBu H H iPr H H H iPr S-100 H Me H S-100 A-2 300 H H H H iPr H H H iPr S-1 H Me H S-3 A-2 301 H H H H iPr H H H iPr S-1 H Me H S-4 A-2 302 H H H H iPr H H H iPr S-1 H Me H S-20 A-2 303 H H H H iPr H H H iPr S-1 H Me H S-47 A-2 304 H H H H iPr H H H iPr S-1 H Me H S-63 A-2 305 H H H H iPr H H H iPr S-4 H Me H S-63 A-2 306 H H H H iPr H H H iPr S-47 H Me H S-63 A-2 307 H H H H iPr H H H iPr Me H Me H S-1 A-2 308 H H H H iPr H H H iPr Me H Me H S-4 A-2 309 H H H H iPr H H H iPr Me H Me H S-20 A-2 310 H H H H iPr H H H iPr Me H Me H S-24 A-2 311 H H H H iPr H H H iPr Me H Me H S-34 A-2 312 H H H H iPr H H H iPr Me H Me H S-47 A-2 313 H H H H iPr H H H iPr Me H Me H S-63 A-2 314 H H H H iPr H H H iPr Me H Me H S-81 A-2 315 H H H H iPr H H H iPr Me H Me H S-82 A-2 316 H H H H iPr H H H iPr Me H Me H S-86 A-2 317 H H H H iPr H H H iPr Me H Me H S-88 A-2 318 H H H H iPr H H H iPr Me H Me H S-98 A-2 319 H H H H iPr H H H iPr Me H Me H S-101 A-2 320 H H H H iPr H H H iPr Me H Cl H S-1 A-2

[0392] [Table 9]

[0393] No <![CDATA[R x1 ]]> <![CDATA[R x2 ]]> <![CDATA[R x3 ]]> <![CDATA[R x4 ]]> <![CDATA[R x5 ]]> <![CDATA[R x6 ]]> <![CDATA[R x7 ]]> <![CDATA[R x8 ]]> <![CDATA[R x9 ]]> <![CDATA[R x10 ]]> <![CDATA[R x11 ]]> <![CDATA[R x12 ]]> <![CDATA[R x13 ]]> <![CDATA[R x14 ]]> <![CDATA[A x1 ]]> 321 H H H H iPr H H H iPr Me H Cl H S-21 A-2 322 H H H H iPr H H H iPr Me H Cl H S-87 A-2 323 H H H H iPr H H H iPr Me H Cl H S-111 A-2 324 H H H H iPr H H H iPr Cl H Cl H S-1 A-2 325 H H H H Me H Me H S-1 Me H Me H S-1 A-2 326 H H H H Me H Me H S-3 Me H Me H S-3 A-2 327 H H H H Me H Me H S-20 Me H Me H S-20 A-2 328 H H H H Me H Me H S-47 Me H Me H S-47 A-2 329 H H H H S-1 H H H S-1 S-1 H H H S-1 A-2 330 H H H H S-1 H H H S-1 S-1 H H H S-1 A-4 331 H H H H S-1 H H H S-1 S-1 H H H S-1 A-5 332 H H H H S-1 H H H S-1 S-1 H H H S-1 A-6 333 H H H H S-1 H H H S-1 S-1 H H H S-1 A-7 334 H H H H S-1 H H H S-1 S-1 H H H S-1 A-8 335 H H H H S-1 H H H S-1 S-1 H H H S-1 A-9 336 H H H H S-1 H H H S-1 S-1 H H H S-1 A-10 337 H H H H S-1 H H H S-1 S-1 H H H S-1 A-11 338 H H H H S-1 H H H S-1 S-1 H H H S-1 A-12 339 H H H H S-1 H H H S-1 S-1 H H H S-1 A-30 340 H H H H S-1 H H H S-1 S-1 H Me H S-1 A-2 341 H H H H S-3 H H H S-3 S-3 H H H S-3 A-5 342 H H H H S-4 H H H S-4 S-4 H H H S-4 A-5 343 H H H H S-40 H H H S-40 S-40 H H H S-40 A-5 344 H H H H S-47 H H H S-47 S-47 H H H S-47 A-5 345 H H H H Me H H H S-1 S-1 H H H S-1 A-2 346 H H H H Me H H H S-1 S-1 H H H S-1 A-5 347 H H H H Me H S-1 H S-1 S-1 H S-1 H S-1 A-1 348 H H H H S-1 H S-1 H S-1 S-1 H S-1 H S-1 A-1 349 H S-1 S-1 H S-1 H S-1 H S-1 S-1 H S-1 H S-1 A-1 350 S-1 H H S-1 S-1 H S-1 H S-1 S-1 H S-1 H S-1 A-1

[0394] Hereinafter, the groups represented by "S-number" (S-1, etc.) are shown below.

[0395] [Chemical formula 27]

[0396]

[0397] [Table 10]

[0398]

[0399] [Chemical formula 28]

[0400]

[0401] [Chemical formula 29]

[0402]

[0403] Hereinafter, the groups represented by "A-number" (A-1, etc.) are shown below.

[0404] In A-1 to A-40, atoms marked with * are carbon atoms directly bonded to the basic structural part (=C<).

[0405] [Chemical formula 30]

[0406]

[0407] [Chemical formula 31]

[0408]

[0409] The molecular weight of the specific compound is not particularly limited, but is preferably 400 to 1200. When the molecular weight is 1200 or less, the vapor deposition temperature does not increase, and the compound is not easily decomposed. When the molecular weight is 400 or more, the glass transition temperature of the vapor-deposited film does not decrease, and the heat resistance of the photoelectric conversion element is improved.

[0410] The specific compound is particularly useful as a material for a photoelectric conversion film used in an imaging element, a light sensor or a photocell. In addition, generally speaking, the specific compound often acts as a p-type organic semiconductor in a photoelectric conversion film. Furthermore, 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 drug material.

[0411] From the viewpoint of stability when used as a p-type organic semiconductor and energy level matching with an n-type organic semiconductor, the specific compound is preferably a compound having a free potential of -5.0 to -6.0 eV in a single film.

[0412] The maximum absorption wavelength of a specific compound is not particularly limited. From the perspective that the photoelectric conversion film in the photoelectric conversion element of the present invention is preferably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion, it is preferably in the range of 500 to 600 nm, and more preferably in the range of 520 to 570 nm.

[0413] The absorption half width of the specific compound is not particularly limited, but from the viewpoint that the photoelectric conversion film in the photoelectric conversion element of the present invention is preferably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion, it is preferably 120 nm or less, more preferably 95 nm or less, further preferably 90 nm or less, and particularly preferably 85 nm or less. The lower limit is not particularly limited, but is often 60 nm or more.

[0414] The maximum absorption wavelength and the absorption half width are values ​​measured in the state of a film of a specific compound (for example, a vapor-deposited film of a specific compound).

[0415] The maximum absorption wavelength of the photoelectric conversion film is not particularly limited. From the perspective that the photoelectric conversion film in the photoelectric conversion element of the present invention is preferably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion, it is preferably in the range of 500 to 600 nm, and more preferably in the range of 520 to 570 nm.

[0416] <n-type organic semiconductor>

[0417] The photoelectric conversion film preferably contains an n-type organic semiconductor as a component other than the above-mentioned specific compound.

[0418] An n-type organic semiconductor is an acceptor organic semiconductor material (compound), and refers to an organic compound having the property of easily accepting electrons. In more detail, an n-type organic semiconductor refers to an organic compound having a large electron affinity when two organic compounds are contacted and used. Therefore, as an acceptor organic semiconductor, any organic compound can be used as long as it is an organic compound with electron accepting properties.

[0419] Examples of the n-type organic semiconductor include fullerenes selected from the group consisting of fullerenes and derivatives thereof, condensed aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); heterocyclic compounds having a 5- to 7-membered ring having at least one of a nitrogen atom, an oxygen atom, and a sulfur atom (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole, and thiazole); polyarylene compounds; fluorene compounds; cyclopentadiene compounds; silyl compounds; 1,4,5,8-naphthalenetetracarboxylic anhydride; 1,4,5,8-naphthalenetetracarboxylic anhydride imide derivatives; oxadiazole derivatives; anthraquinone dimethane derivatives; diphenyl quinone derivatives; quinone derivatives; bathocuproine, bathophenanthroline and derivatives thereof; triazole compounds; distyrylarylene; metal complexes having nitrogen-containing heterocyclic compounds as ligands; silylene compounds; and compounds described in paragraphs

[0056] to

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

[0420] Among them, the n-type organic semiconductor (compound) is preferably one containing fullerenes selected from the group consisting of fullerene and derivatives thereof.

[0421] Examples of the fullerene 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.

[0422] As for the fullerene derivative, for example, there can be mentioned compounds in which a substituent is added to the above-mentioned fullerene. As the substituent, an alkyl group, an aryl group or a heterocyclic group is preferred. As the fullerene derivative, the compound described in Japanese Patent Application Laid-Open No. 2007-123707 is preferred.

[0423] In addition, as an n-type organic semiconductor, an organic pigment can be used. For example, cyanine pigments, styryl pigments, hemicyanine pigments, merocyanine pigments (including zero methine merocyanine (simple merocyanine)), rhodanine pigments, alopolar pigments, oxonol pigments, hemicyanine pigments, squaryl pigments, crotonium pigments, azamethine pigments, coumarin pigments, arylidene pigments, anthraquinone pigments, triphenylmethane pigments, azo pigments, methine azo pigments, metallocene pigments, fluorenone pigments, fulgide pigments, perylene pigments, phenazine pigments, phenothiazine pigments, quinone pigments, diphenylmethane pigments, polyene pigments, acridine pigments, acridone pigments, diphenylamine pigments, quinoline yellow pigments, phenoxazine pigments, phthaloperyl pigments, dioxane pigments, porphyrin pigments, chlorophyll pigments, phthalocyanine pigments, subphthalocyanine pigments and metal complex pigments can be cited.

[0424] The molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.

[0425] From the viewpoint that the photoelectric conversion film in the photoelectric conversion element of the present invention is preferably used as an organic photoelectric conversion film that receives (absorbs) green light and performs photoelectric conversion, the n-type organic semiconductor is preferably colorless or has a maximum absorption wavelength and / or absorption waveform close to that of a specific compound. As a specific numerical value, the maximum absorption wavelength of the n-type organic semiconductor is preferably below 400 nm or in the range of 500 to 600 nm.

[0426] The photoelectric conversion film preferably has a bulk heterostructure formed in a state where a specific compound and an n-type organic semiconductor are mixed. The bulk heterostructure is a layer in which a specific compound and an n-type organic semiconductor are mixed and dispersed in the photoelectric conversion film. A photoelectric conversion film having a bulk heterostructure can be formed by any of a wet method and a dry method. In addition, the bulk heterostructure is described in detail in paragraphs

[0013] to

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

[0427] From the viewpoint of the responsiveness of the photoelectric conversion element, the content of the specific compound relative to the total content of the specific compound and the n-type organic semiconductor (=film thickness converted as a single layer of the specific compound / (film thickness converted as a single layer of the specific compound + film thickness converted as a single layer of the n-type organic semiconductor) × 100) is preferably 20 to 80 volume %, and more preferably 40 to 80 volume %.

[0428] Furthermore, when the photoelectric conversion film contains a p-type organic semiconductor described later, the content of the specific compound (=film thickness when converted as a single layer of the specific compound / (film thickness when converted as a single layer of the specific compound + film thickness when converted as a single layer of the n-type organic semiconductor + film thickness when converted as a single layer of the p-type organic semiconductor) × 100) is preferably 15 to 75% by volume, and more preferably 35 to 75% by volume.

[0429] In addition, the photoelectric conversion film is preferably substantially composed of a specific compound, an n-type organic semiconductor, and a p-type organic semiconductor included as required. Substantially means that the total content of the specific compound, the n-type organic semiconductor, and the p-type organic semiconductor included as required is 95% by mass or more relative to the total mass of the photoelectric conversion film.

[0430] The n-type organic semiconductor contained in the photoelectric conversion film may be used alone or in combination of two or more.

[0431] Furthermore, the photoelectric conversion film may further contain a p-type organic semiconductor in addition to the specific compound and the n-type organic semiconductor. Examples of the p-type organic semiconductor include the following compounds.

[0432] The p-type organic semiconductor referred to herein refers to a p-type organic semiconductor that is a compound other than the specific compound. When the p-type organic semiconductor is included in the photoelectric conversion film, the p-type organic semiconductor may be used alone or in combination of two or more.

[0433] <p-type organic semiconductor>

[0434] The p-type organic semiconductor refers to a donor organic semiconductor material (compound), and refers to an organic compound having a property of easily donating electrons. More specifically, the p-type organic semiconductor refers to an organic compound having a small free potential when two organic compounds are used in contact with each other.

[0435] Examples of p-type organic semiconductors include triarylamine compounds (e.g., N,N″-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine (TPD), 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), compounds described in paragraphs

[0128] to

[0148] of JP-A-2011-228614, compounds described in paragraphs

[0052] to

[0063] of JP-A-2011-176259, compounds described in paragraphs

[0119] to

[0148] of JP-A-2011-225544). 158], the compounds described in

[0044] to

[0051] of JP-A-2015-153910, and the compounds described in

[0086] to

[0090] of JP-A-2012-094660, etc.), pyrazoline compounds, styrylamine compounds, hydrazone compounds, polysilane compounds, thiophene compounds (for example, thienothiophene derivatives, dibenzothiophene derivatives, benzodithiophene derivatives, dithienothiophene derivatives, [1]benzothieno[3,2-b]thiophene (BTBT) derivatives, thieno[3,2-f:4,5-f′] bis[1]benzothiophene (TBBT) derivatives, compounds described in paragraphs

[0031] to

[0036] of Japanese Patent Application Laid-Open No. 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

[0099] to

[0109] of Japanese Patent Application Laid-Open No. 2017-076766 The compounds described in paragraphs

[0029] to

[0034] of the WO2018-207722, the compounds described in paragraphs

[0015] to

[0025] of WO2018-207722, the compounds described in paragraphs

[0045] to

[0053] of JP-A-2019-054228, the compounds described in paragraphs

[0045] to

[0055] of WO2019-058995, the compounds described in paragraphs

[0063] to

[0089] of WO2019-081416 Compounds described in paragraphs

[0033] to

[0036] of Japanese Patent Application Laid-Open No. 2019-080052, compounds described in paragraphs

[0044] to

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

[0041] to

[0046] of WO2019-093188, etc.), cyanine compounds, oxonol compounds, polyamine compounds, indole compounds, pyrrole compounds, pyrazole compounds, polyarylene compounds, lene) compounds, condensed aromatic carbocyclic compounds (for example, naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives and fluoranthene derivatives), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyaryl alkane compounds, pyrazolone compounds, amino-substituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having nitrogen-containing heterocyclic compounds as ligands.

[0436] Examples of the p-type organic semiconductor include compounds having a lower free potential than that of the n-type organic semiconductor. As long as this condition is satisfied, the organic dyes exemplified as the n-type organic semiconductor can be used.

[0437] Compounds that can be used as the p-type semiconductor compound are exemplified below.

[0438] [Chemical formula 32]

[0439]

[0440] [Chemical formula 33]

[0441]

[0442] [Chemical formula 34]

[0443]

[0444] [Chemical formula 35]

[0445]

[0446] The photoelectric conversion film containing the specific compound is a non-luminescent film and has characteristics different from an organic light emitting diode (OLED). A non-luminescent film refers to a film having a luminescent quantum efficiency of 1% or less, preferably 0.5% or less, and more preferably 0.1% or less.

[0447] <Film Formation Method>

[0448] The photoelectric conversion film is mainly formed by a dry film-forming method. As a dry film-forming method, for example, physical vapor deposition methods such as evaporation (especially vacuum evaporation), sputtering, ion plating, and MBE (Molecular Beam Epitaxy) and CVD (Chemical Vapor Deposition) methods such as plasma polymerization can be cited. Among them, vacuum evaporation is preferred. When the photoelectric conversion film is formed by vacuum evaporation, the manufacturing conditions such as vacuum degree and evaporation temperature can be set according to conventional methods.

[0449] The thickness of the photoelectric conversion film is preferably 10 to 1000 nm, more preferably 50 to 800 nm, further preferably 50 to 500 nm, and particularly preferably 50 to 300 nm.

[0450] <Electrode>

[0451] The electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Examples of the conductive material include metals, alloys, metal oxides, conductive compounds, and mixtures thereof.

[0452] Since light is incident from the upper electrode 15, it is preferred that the upper electrode 15 is transparent to the light to be detected. As materials constituting the upper electrode 15, for example, conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO: Antimony Tin Oxide, FTO: Fluorine doped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO: Indium Tin Oxide) and indium zinc oxide (IZO: Indium zinc oxide); metal thin 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. Among them, conductive metal oxides are preferred from the viewpoints of high conductivity and transparency.

[0453] Generally, if the conductive film is made thinner than a certain range, it will lead to a sharp increase in resistance value. However, in the solid-state imaging element assembled with the photoelectric conversion element of this embodiment, the sheet resistance is preferably 100 to 10000Ω / □, and the film thickness range that can be thinned is large. In addition, the thinner the thickness of the upper electrode (transparent conductive film) 15, the less the amount of light absorbed, and generally speaking, the transmittance increases. The increase in transmittance increases the light absorption in the photoelectric conversion film, thereby increasing the photoelectric conversion energy, so it is preferred. Considering the suppression of leakage current accompanying thin filming, the increase in resistance value of the film, and the increase in transmittance, the film thickness of the upper electrode 15 is preferably 5 to 100nm, and more preferably 5 to 20nm.

[0454] The lower electrode 11 may be transparent or non-transparent and reflect light depending on the application. Examples of the material constituting the lower electrode 11 include conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metals such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (for example, titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole.

[0455] The method for forming the electrode is not particularly limited and can be appropriately selected according to the electrode material. Specifically, wet methods such as printing and coating methods, physical methods such as vacuum evaporation, sputtering and ion plating, and chemical methods such as CVD and plasma CVD methods can be cited.

[0456] When the material of the electrode is ITO, examples of the method include an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction method (sol-gel method, etc.), and coating of an indium tin oxide dispersion.

[0457] <Charge blocking film: electron blocking film, hole blocking film>

[0458] The photoelectric conversion element of the present invention preferably has one or more intermediate layers between the conductive film and the transparent conductive film in addition to the photoelectric conversion film. As the above-mentioned intermediate layer, a charge blocking film can be cited. If the photoelectric conversion element has this film, the characteristics (photoelectric conversion efficiency and responsiveness, etc.) of the obtained photoelectric conversion element are more excellent. As the charge blocking film, an electron blocking film and a hole blocking film can be cited. Below, each film is described in detail.

[0459] (Electron blocking film)

[0460] The electron blocking film is a donor organic semiconductor material (compound), and the above-mentioned p-type organic semiconductor can be used.

[0461] Furthermore, a polymer material can also be used as the electron blocking film.

[0462] Examples of the polymer material include polymers such as phenylacetylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, and derivatives thereof.

[0463] In addition, the electron blocking film may be composed of a plurality of films.

[0464] The electron blocking film can be made of an inorganic material. Generally speaking, the dielectric constant of an inorganic material is greater than that of an organic material. Therefore, when an inorganic material is used for an electron blocking film, a larger voltage is applied to the photoelectric conversion film, thereby increasing the photoelectric conversion efficiency. Examples of inorganic materials that can be used as an electron blocking film include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, indium copper oxide, indium silver oxide, and iridium oxide.

[0465] (Hole Blocking Film)

[0466] The hole blocking film is an acceptor organic semiconductor material (compound), and the above-mentioned n-type semiconductor can be used.

[0467] The method for manufacturing the charge blocking film is not particularly limited, and dry film forming methods and wet film forming methods can be cited. As dry film forming methods, evaporation methods and sputtering methods can be cited. The evaporation method can be any of physical vapor deposition (PVD: physical vapor deposition (Physical Vapor Deposition)) method and chemical vapor deposition (CVD) method, preferably a physical vapor deposition method such as a vacuum evaporation method. As a wet film forming method, for example, an inkjet method, a spray method, a nozzle printing method, a spin coating method, a dip coating method, a casting method, a die coating method, a roller coating method, a rod coating method and a gravure coating method can be cited. From the viewpoint of high-precision patterning, an inkjet method is preferably used.

[0468] The thickness of each of the charge blocking films (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.

[0469] <Substrate>

[0470] The photoelectric conversion element may further include a substrate. The type of substrate used is not particularly limited, and examples thereof include a semiconductor substrate, a glass substrate, and a plastic substrate.

[0471] The position of the substrate is not particularly limited, and generally, a conductive film, a photoelectric conversion film, and a transparent conductive film are sequentially stacked on the substrate.

[0472] <Sealing layer>

[0473] The photoelectric conversion element may also have a sealing layer. Sometimes the performance of the photoelectric conversion material is significantly degraded due to the presence of degradation factors such as water molecules. Therefore, the photoelectric conversion film is entirely covered and sealed with a sealing layer such as a dense ceramic such as a metal oxide, metal nitride or metal nitride oxide that does not allow water molecules to penetrate, or diamond-like carbon (DLC: Diamond-like Carbon), thereby preventing the above-mentioned degradation.

[0474] The sealing layer may be selected and manufactured according to the description in paragraphs

[0210] to

[0215] of Japanese Patent Application Laid-Open No. 2011-082508.

[0475] 〔Imaging element〕

[0476] As a use of the photoelectric conversion element, for example, an imaging element can be cited. An imaging element is an element that converts the optical information of an image into an electrical signal. It usually means that a plurality of photoelectric conversion elements are arranged in a matrix on the same plane, and each photoelectric conversion element (pixel) can convert the optical signal into an electrical signal, and the electrical signal is output to the outside of the imaging element one by one for each pixel. Therefore, each pixel is composed of one or more photoelectric conversion elements and one or more transistors.

[0477] Figure 3 The schematic cross-sectional view shows a schematic configuration of an imaging element for explaining one embodiment of the present invention. The imaging element is mounted in an imaging element such as a digital camera or a digital video camera, an electronic endoscope, or an imaging module such as a mobile phone.

[0478] Figure 3 The imaging element 20a shown includes the photoelectric conversion element 10a of the present invention, a blue photoelectric conversion element 22, and a red photoelectric conversion element 24, which are stacked in the direction in which light is incident. As described above, the photoelectric conversion element 10a can mainly function as a green photoelectric conversion element that can receive green light.

[0479] The imaging element 20a is a so-called laminated color separation imaging element. The wavelength spectra detected by the photoelectric conversion element 10a, the blue photoelectric conversion element 22, and the red photoelectric conversion element 24 are different. That is, the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 are equivalent to photoelectric conversion elements that receive light of a wavelength different from the light received (absorbed) by the photoelectric conversion element 10a. The photoelectric conversion element 10a can mainly receive green light, the blue photoelectric conversion element 22 can mainly receive blue light, and the red photoelectric conversion element can mainly receive red light.

[0480] In addition, green light refers to light with a wavelength in the range of 500 to 600 nm, blue light refers to light with a wavelength in the range of 400 to 500 nm, and red light refers to light with a wavelength in the range of 600 to 700 nm.

[0481] When light enters the imaging element 20a from the direction of the arrow, first, although green light is mainly absorbed by the photoelectric conversion element 10a, blue light and red light are transmitted through the photoelectric conversion element 10a. When the light that has transmitted the photoelectric conversion element 10a enters the blue photoelectric conversion element 22, blue light is mainly absorbed, but red light is transmitted through the blue photoelectric conversion element 22. Then, the light that has transmitted the blue photoelectric conversion element 22 is absorbed by the red photoelectric conversion element 24. In this way, in the imaging element 20a which is a stacked color separation imaging element, one pixel can be composed of three light receiving parts of green, blue and red, and the area of ​​the light receiving part can be large.

[0482] In particular, in the photoelectric conversion element 10 a of the present invention, since the half width of the absorption peak is narrow, the absorption of blue light and red light is hardly generated, and the detectability in the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 is hardly affected.

[0483] The configurations of the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 are not particularly limited.

[0484] For example, it can be a photoelectric conversion element that uses silicon and has a structure that separates colors by the difference in light absorption length. As a more specific example, the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 can both be made of silicon. In this case, with respect to the light including blue light, green light and red light incident on the imaging element 20a in the direction of the arrow, mainly the green light as the light of the intermediate wavelength is received through the photoelectric conversion element 10a, and the remaining blue light and red light become easy to separate colors. There is a difference in the light absorption length of blue light and red light to silicon (the wavelength dependence of the absorption coefficient of silicon), and blue light is easily absorbed near the surface of silicon, and red light can invade a relatively deep position of silicon. Based on this difference in light absorption length, blue light is mainly received by the blue photoelectric conversion element 22 present in a shallower position, and red light is mainly received by the red photoelectric conversion element 24 present in a deeper position.

[0485] Furthermore, the blue photoelectric conversion element 22 and the red photoelectric conversion element 24 may be photoelectric conversion elements (blue photoelectric conversion element 22 or red photoelectric conversion element 24) having a structure including a conductive film, an organic photoelectric conversion film having maximum absorption of blue light or red light, and a transparent conductive film in sequence.

[0486] exist Figure 3 In the embodiment, the photoelectric conversion element of the present invention, the blue photoelectric conversion element, and the red photoelectric conversion element are sequentially arranged from the incident side of light, but the present invention is not limited to this method, and other arrangement orders are also possible. For example, the blue photoelectric conversion element, the photoelectric conversion element of the present invention, and the red photoelectric conversion element may be sequentially arranged from the side where light is incident.

[0487] As described above, as an imaging element, a structure in which photoelectric conversion elements of three primary colors, namely blue, green and red, are stacked is described, but it may be two layers (two colors) or four layers (four colors) or more.

[0488] For example, the photoelectric conversion element 10a of the present invention may be disposed on the arranged blue photoelectric conversion element 22 and the red photoelectric conversion element 24. Furthermore, a color filter that absorbs light of a specific wavelength may be further disposed on the light incident side as needed.

[0489] The form of the imaging element is not limited to Figure 3 The above-mentioned forms may also be in other forms.

[0490] For example, a configuration may be adopted in which the photoelectric conversion element of the present invention, a blue photoelectric conversion element, and a red photoelectric conversion element are arranged at positions within the same plane.

[0491] Furthermore, a structure in which the photoelectric conversion element is used in a single layer may be adopted. For example, a structure in which blue, red, and green color filters are arranged on the photoelectric conversion element 10a of the present invention to separate colors may be adopted.

[0492] 〔Light sensor〕

[0493] As other uses of the photoelectric conversion element, for example, photocells and optical sensors can be cited, but it is preferred that the photoelectric conversion element of the present invention is used as an optical sensor. As an optical sensor, the above-mentioned photoelectric conversion element can be used alone, or it can be used as a line sensor in which the above-mentioned photoelectric conversion element is arranged in a straight line or a two-dimensional sensor arranged on a plane.

[0494] 〔Compound〕

[0495] The present invention includes the invention of a compound. The compound of the present invention is the same as the compound represented by the above formula (4-2).

[0496] Example

[0497] Although Examples are shown below, the present invention is not limited to these.

[0498] [Compounds used in photoelectric conversion films]

[0499] <Synthesis of Compound (D-1)>

[0500] Compound (D-1) was synthesized according to the following scheme.

[0501] [Chemical formula 36]

[0502]

[0503] 2,3-Dichloroquinoxaline (5.00 g, 25.1 mmol) and aniline (9.31 g, 100 mmol) were added to xylene (20 mL) in a flask to obtain a reaction solution. The obtained reaction solution was refluxed and reacted for 6 hours. Methanol (80 mL) was added to the reaction solution after natural cooling, and stirred at room temperature for 30 minutes to precipitate a solid. Then, the solid was filtered off, and the obtained solid was washed with methanol to obtain compound (A-1) (3.20 g, 10.2 mmol, yield 41%).

[0504] Compound (A-1) (3.00 g, 9.60 mmol) was added to acetic anhydride (Ac2O) (18 mL) in a flask, and p-toluenesulfonic acid monohydrate (p-TsOH·H2O) (1.83 g, 9.60 mmol) was added thereto to obtain a reaction solution. The obtained reaction solution was reacted at 100°C for 7 hours. Water (50 mL) and ethyl acetate (30 mL) were added to the reaction solution after natural cooling, and the mixture was stirred at room temperature for 30 minutes to precipitate a solid. Then, the solid was filtered out, and the obtained solid was washed with ethyl acetate to obtain compound (A-2) (2.10 g, 4.13 mmol, yield 43%).

[0505] Compound (A-2) (509 mg, 1.00 mmol) and compound (A-3) (329 mg, 1.1 mmol) were placed in a flask, and acetic anhydride (Ac2O) (5.0 mL) and triethylamine (Et3N) (0.50 mL) were added thereto to obtain a reaction solution. The obtained reaction solution was reacted at 100°C for 5 hours. Water (15 mL) and methanol (15 mL) were added to the reaction solution after natural cooling, and the mixture was stirred at room temperature for 30 minutes to precipitate a solid. Then, the solid was filtered out, and the obtained solid was washed with methanol to obtain a crude body. The obtained crude body was purified by silica gel column chromatography (eluent: a mixed solution of ethyl acetate / chloroform = 1 / 9 (mass ratio)), and then recrystallized from methanol to obtain compound (D-1) (220 mg, 0.41 mmol, yield 41%).

[0506] The obtained compound (D-1) was identified by NMR (nuclear magnetic resonance) and MS (Mass Spectrometry).

[0507] exist Figure 5 Shown in 1 H NMR spectrum (400 MHz, CDCl3).

[0508] 1 MS (ESI + )m / z:543.2([M+H] + )

[0509] Referring to the synthesis method of the above-mentioned compound (D-1), compounds (D-2) to (D-78) were synthesized.

[0510] exist Figures 5 to 38Compounds (D-2) to (D-5), (D-7), (D-10) to (D-14), (D-16), (D-25) to (D-29), (D-31), (D-32), (D-34), (D-35), (D-37) to (D-41), (D-45) to (D-48), (D-59), (D-69), (D-71), (D-75), and (D-76) are shown. 1 H NMR spectrum (400 MHz, CDCl3).

[0511] Compounds (D-1) to (D-78) and comparative compounds (R-1) to (R-6) are shown below.

[0512] [Chemical formula 37]

[0513]

[0514] [Chemical formula 38]

[0515]

[0516] [Chemical formula 39]

[0517]

[0518] [Chemical formula 40]

[0519]

[0520] [Chemical formula 41]

[0521]

[0522] [Chemical formula 42]

[0523]

[0524] [Chemical formula 43]

[0525]

[0526] [evaluate]

[0527] <Fabrication of Photoelectric Conversion Element>

[0528] The obtained compound was used to prepare Figure 1 Here, the photoelectric conversion element is composed of a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, and an upper electrode 15.

[0529] Specifically, amorphous ITO was formed on a glass substrate by sputtering to form a lower electrode 11 (thickness: 30 nm), and the following compound (EB-1) was further formed on the lower electrode 11 by vacuum heating evaporation to form an electron blocking film 16A (thickness: 30 nm).

[0530] Furthermore, while the temperature of the substrate was controlled at 25° C., the compound (D-1) and the fullerene (C-1) were co-deposited on the electron blocking film 16A by vacuum evaporation in a thickness of 100 nm and 100 nm, respectively, in terms of a single layer. 60 ) is used to form a film, thereby forming a photoelectric conversion film 12 with a bulk heterostructure of 200 nm.

[0531] Furthermore, an upper electrode 15 (transparent conductive film) (thickness: 10 nm) is formed by sputtering amorphous ITO on the photoelectric conversion film 12. After a SiO film as a sealing layer is formed on the upper electrode 15 by vacuum evaporation, an aluminum oxide (Al(Al2O3) layer is formed thereon by ALCVD (Atomic Layer Chemical Vapor Deposition)) to produce a photoelectric conversion element.

[0532] [Chemical formula 44]

[0533]

[0534] Each photoelectric conversion element was produced in the same manner except that compound (D-1) was changed to compounds (D-2) to (D-78) or compounds (R-1) to (R-7).

[0535] <Drive confirmation (dark current evaluation)>

[0536] With respect to each of the obtained photoelectric conversion elements, the dark current was measured by the following method.

[0537] A voltage of 2.5×10 5 The electric field strength was 50 nA / cm2 and the current value (dark current) in the dark was measured. As a result, it was confirmed that the dark current was 50 nA / cm2 in all photoelectric conversion elements. 2 Below, a sufficiently low dark current is shown.

[0538] <Evaluation of heat resistance>

[0539] The heat resistance of each of the obtained photoelectric conversion elements was evaluated by the following method.

[0540] Specifically, each photoelectric conversion element obtained was heated on a hot plate at 180° C. for 30 minutes. A voltage of 2.0×10 5 The dark current at 540 nm was measured by irradiating light from the upper electrode (transparent conductive film) side with an electric field intensity of 100 V / cm. The dark current before heating was set to 1, and the relative value of the dark current after heating was evaluated.

[0541] A relative value of 1.5 or less was evaluated as A, greater than 1.5 and 3 or less was evaluated as B, greater than 3 and 10 or less was evaluated as C, and greater than 10 was evaluated as D. In addition, substantially B or more was preferred, and A was more preferred. The results are shown in Table 1.

[0542] [Table 11]

[0543] Table 1-1 Compounds used Heat resistance of photoelectric conversion elements Example A1 D-1 B Example A2 D-2 A Example A3 D-3 A Example A4 D-4 A Example A5 D-5 A Example A6 D-6 A Example A7 D-7 A Example A8 D-8 A Embodiment A9 D-9 B Embodiment A10 D-10 A Embodiment A11 D-11 A Example A12 D-12 A Embodiment A13 D-13 A Embodiment A14 D-14 A Embodiment A15 D-15 A Embodiment A16 D-16 A Embodiment A17 D-17 A Embodiment A18 D-18 A Embodiment A19 D-19 A Example A20 D-20 A Example A21 D-21 A Example A22 D-22 B Example A23 D-23 B Example A24 D-24 A Comparative Example A1 R-1 C

[0544] [Table 12]

[0545]

[0546] From the results shown in the table, it was confirmed that the photoelectric conversion element of the present invention has excellent heat resistance.

[0547] The specific compound is a compound represented by formula (4), formula (4-2) or formula (5), and when R a1 and R a2 is a group represented by formula (X), -C(R L1 )(R L2 )(R L3 ), or a polycyclic aromatic group which may have a substituent, it was confirmed that the heat resistance of the photoelectric conversion element was even better (the results of Examples A1, A9, A22, A23, A54, A75, A76, A77, and A78).

[0548] <Production of imaging elements>

[0549] The above-mentioned photoelectric conversion elements using compounds (D-1) to (D-78) were used to prepare imaging elements after the photoelectric conversion elements were subjected to the same heat treatment as in <Evaluation of Heat Resistance>. As a result, no performance problems of the imaging elements were found.

[0550] <Evaluation of light absorption properties of compounds>

[0551] While the temperature of the glass substrate was controlled at 25° C., a vapor-deposited film (thickness: 100 nm) using any one of the compounds shown in Table 2 was formed on the glass substrate by vacuum vapor deposition.

[0552] The absorption shape (absorption spectrum) of each vapor-deposited film obtained was measured using a spectrophotometer U3310 manufactured by Hitachi High-Technologies Corporation. From the measurement results, the maximum absorption wavelength of the absorption spectrum and the difference between two wavelengths at which the absorbance becomes 0.5 when the absorbance at the maximum absorption wavelength is set to 1 (absorption half width) were obtained.

[0553] In addition, when there are two or more wavelengths where the absorbance becomes 0.5, the above two wavelengths are "the wavelength where the absorbance becomes 0.5 among wavelengths larger than the maximum absorption wavelength and closest to the maximum absorption wavelength" and "the wavelength where the absorbance becomes 0.5 among wavelengths smaller than the maximum absorption wavelength and closest to the maximum absorption wavelength".

[0554] Table 2 shows the measured absorption half width and the maximum absorption wavelength of the absorption spectrum.

[0555] The results of the absorption half width were classified according to the following criteria: The smaller the value of the absorption half width, the more preferred it is.

[0556] A: Absorption half width is less than 85nm

[0557] B: Absorption half width greater than 85nm and less than 90nm

[0558] C: Absorption half width greater than 90nm and less than 95nm

[0559] D: Absorption half width greater than 95nm and less than 120nm

[0560] E: Absorption half width greater than 120nm

[0561] In Table 2, “R a1 , R a2 The column "" indicates that the compound used is in accordance with R in formula (1) a1 , R a2 "ZB" represents a group represented by formula (ZB). "Polycyclic Ar" represents a polycyclic aromatic group which may have a substituent. "X" is a group represented by formula (X), and represents a group other than a group represented by formula (ZB). "-C(R L1 )(R L2 )(R L3 )" means the above-C(R L1 )(R L2 )(R L3 ) are represented by "-". A group that does not meet any of these conditions is represented by "-".

[0562] [Table 13]

[0563]

[0564] It was confirmed that the absorption half width of the specific compound was narrow.

[0565] When a specific compound is applied to formula (1), when R a1 and R a2 is a group represented by formula (X) (preferably a group represented by formula (ZB)), a polycyclic aromatic group which may have a substituent, or -C(R L1 )(R L2 )(R L3 ), it was confirmed that the absorption half width became narrower (the results of Examples B2 to B35, etc.).

[0566] When the specific compound is a compound represented by formula (3), formula (4), formula (4-2) or formula (5), it is confirmed that the absorption half width is narrower (comparison between Examples B2 and B35, etc.).

[0567] When the specific compound is applied to the formula (1), when R a1 and R a2 When it is preferably a group represented by formula (ZB) or a polycyclic aromatic group which may have a substituent, it is confirmed that the absorption half width becomes narrower (the results of Examples B2 to B9, B12 to B34 (the results of comparing the examples in which the specific compound is a compound represented by formula (3), formula (4), formula (4-2) or formula (5)), etc.).

[0568] In formula (ZB), when R f3 and R f4 One or both of them is -CH(R d3 )(R d4 ) or aromatic group, it was confirmed that the absorption half width became particularly narrow (the results of Examples B4 to B8, B12 to B34 (the results of comparing the examples in which the specific compound is a compound represented by Formula (3), Formula (4), Formula (4-2) or Formula (5)) etc.).

[0569] Explanation of symbols

[0570] 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, 20a-imaging element, 22-blue photoelectric conversion element, 24-red photoelectric conversion element.

Claims

1. A photoelectric conversion element comprising, in order, a conductive film, a photoelectric conversion film, and a transparent conductive film, wherein: The photoelectric conversion film comprises a compound represented by formula (2), [Chemical formula 2] In formula (2), A 1 represents a ring having a group represented by formula (AW), *1-LYZ-*2(AW) In formula (AW), *1 indicates the bonding position to the carbon atom in -C(=O)- indicated in formula (2), and *2 indicates the bonding position to R in formula (2). 1 The bonding position of the carbon atoms that are directly bonded together to form a double bond, In formula (AW), L represents a single bond or -NR L -,R L represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Y stands for -CR Y1 =CR Y2 -、-CS-NR Y3 -、-CO-、-CS-、-NR Y4 -、-N=CR Y5 -, or 1,8-naphthalene diyl which may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R Y1 ~R Y5 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, And, when Y represents -CR Y1 =CR Y2 -, R Y1 With R Y2 They can bond to each other to form a benzene ring or a pyridine ring, R Y1 With R Y2 The ring formed by bonding to each other may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Z represents a single bond, -CO-, -S-, -SO2- or -CR Z1 =CR Z2 -, R Z1 and R Z2 each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R 1 and R 2 Each independently represents a hydrogen atom, R a1 and R a2 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 Each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, and * represents a bonding position, X 1 and X 4 Each independently represents a nitrogen atom, X 2 and X 3 Each independently represents -CR c1 =, R c1 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, When R c1 When there are multiple, there are multiple R c1 They may be bonded to each other to form a benzene ring or a pyridine ring.

2. The photoelectric conversion element according to claim 1, wherein The compound represented by formula (2) is a compound represented by formula (3), [Chemical formula 3] In formula (3), A 1 represents a ring having a group represented by formula (AW), *1-LYZ-*2(AW) In formula (AW), *1 indicates the bonding position to the carbon atom in -C(=O)- indicated in formula (2), and *2 indicates the bonding position to R in formula (2). 1 The bonding position of the carbon atoms that are directly bonded together to form a double bond, In formula (AW), L represents a single bond or -NR L -,R L represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Y stands for -CR Y1 =CR Y2 -、-CS-NR Y3 -、-CO-、-CS-、-NR Y4 -、-N=CR Y5 -, or 1,8-naphthalene diyl which may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R Y1 ~R Y5 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, And, when Y represents -CR Y1 =CR Y2 -, R Y1 With R Y2 They can bond to each other to form a benzene ring or a pyridine ring, R Y1 With R Y2 The ring formed by bonding to each other may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Z represents a single bond, -CO-, -S-, -SO2- or -CR Z1 =CR Z2 -, R Z1 and R Z2 each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, E 3 Represents nitrogen atom or -CR 3 =, E 6 Represents nitrogen atom or -CR 6 =, R 3 ~R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, R a1 and R a2 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, *Indicates bonding position.

3. The photoelectric conversion element according to claim 1 or 2, wherein: The compound represented by formula (2) is a compound represented by formula (4), [Chemical formula 4] In formula (4), E 3 Represents nitrogen atom or -CR 3 =, E 6 Represents nitrogen atom or -CR 6 =, R 3 ~R 8 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, R a1 and R a2 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, * indicates the bonding position, R 7 With R 8 They can bond to each other to form a benzene ring or a pyridine ring, R 7 With R 8 The ring formed by bonding to each other may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms.

4. The photoelectric conversion element according to claim 1 or 2, wherein The compound represented by formula (2) is a compound represented by formula (5), [Chemical formula 5] In formula (5), E 3 Represents nitrogen atom or -CR 3 =, E 6 Represents nitrogen atom or -CR 6 =, R 3 ~R 6 and R 9 ~R 12 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, R a1 and R a2 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, * indicates the bonding position, R 10 With R 11 They may be bonded to each other to form a benzene ring or a pyridine ring.

5. The photoelectric conversion element according to claim 1, wherein The photoelectric conversion film further comprises an n-type organic semiconductor, The photoelectric conversion film has a bulk heterostructure formed in a state where the compound represented by formula (2) and the n-type organic semiconductor are mixed.

6. The photoelectric conversion element according to claim 5, wherein The n-type organic semiconductor comprises fullerenes selected from the group consisting of fullerenes and derivatives thereof.

7. The photoelectric conversion element according to claim 1 or 2, wherein: Between the conductive film and the transparent conductive film, one or more intermediate layers are provided in addition to the photoelectric conversion film. 8 . An imaging element comprising the photoelectric conversion element according to claim 1 . 9 . The imaging element according to claim 8 , further comprising another photoelectric conversion element that receives light having a wavelength different from that of the light received by the photoelectric conversion element.

10. The imaging element according to claim 9, wherein The photoelectric conversion element and the other photoelectric conversion element are stacked, At least a portion of the incident light is transmitted through the photoelectric conversion element and then received by the other photoelectric conversion element.

11. The imaging element according to claim 9 or 10, wherein: The photoelectric conversion element is a green photoelectric conversion element, The other photoelectric conversion elements include a blue photoelectric conversion element and a red photoelectric conversion element. 12 . A photosensor comprising the photoelectric conversion element according to claim 1 .

13. A compound represented by formula (2): [Chemical formula 7] In formula (2), A 1 represents a ring having a group represented by formula (AW), *1-LYZ-*2(AW) In formula (AW), *1 indicates the bonding position to the carbon atom in -C(=O)- indicated in formula (2), and *2 indicates the bonding position to R in formula (2). 1 The bonding position of the carbon atoms that are directly bonded together to form a double bond, In formula (AW), L represents a single bond or -NR L -,R L represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Y stands for -CR Y1 =CR Y2 -、-CS-NR Y3 -、-CO-、-CS-、-NR Y4 -、-N=CR Y5 -, or 1,8-naphthalene diyl which may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R Y1 ~R Y5 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, And, when Y represents -CR Y1 =CR Y2 -, R Y1 With R Y2 They can bond to each other to form a benzene ring or a pyridine ring, R Y1 With R Y2 The ring formed by bonding to each other may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Z represents a single bond, -CO-, -S-, -SO2- or -CR Z1 =CR Z2 -, R Z1 and R Z2 each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R 1 and R 2 Each independently represents a hydrogen atom, X 1 and X 4 Each independently represents a nitrogen atom, X 2 and X 3 Respectively represent -CR c1 =, R c1 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, When R c1 When there are multiple, there are multiple R c1 They can bond to each other to form a benzene ring or a pyridine ring. R a1 and R a2 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, *Indicates bonding position.

14. The compound according to claim 13, wherein It is a compound represented by formula (3), [Chemical formula 9] In formula (3), A 1 represents a ring having a group represented by formula (AW), *1-LYZ-*2(AW) In formula (AW), *1 indicates the bonding position to the carbon atom in -C(=O)- indicated in formula (2), and *2 indicates the bonding position to R in formula (2). 1 The bonding position of the carbon atoms that are directly bonded together to form a double bond, In formula (AW), L represents a single bond or -NR L -,R L represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Y stands for -CR Y1 =CR Y2 -、-CS-NR Y3 -、-CO-、-CS-、-NR Y4 -、-N=CR Y5 -, or 1,8-naphthalene diyl which may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R Y1 ~R Y5 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, And, when Y represents -CR Y1 =CR Y2 -, R Y1 With R Y2 They can bond to each other to form a benzene ring or a pyridine ring, R Y1 With R Y2 The ring formed by bonding to each other may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, Z represents a single bond, -CO-, -S-, -SO2- or -CR Z1 =CR Z2 -, R Z1 and R Z2 each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, E 3 Represents nitrogen atom or -CR 3 =, E 6 Represents nitrogen atom or -CR 6 =, R 3 ~R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, R a1 and R a2 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, *Indicates bonding position.

15. The compound according to claim 13 or 14, wherein It is a compound represented by formula (4-2), [Chemical formula 11] In formula (4-2), E 3 Represents nitrogen atom or -CR 3 =, E 6 Represents nitrogen atom or -CR 6 =, R 3 ~R 8 each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms, R 7 With R 8 They can bond to each other to form a benzene ring or a pyridine ring, R 7 With R 8 The ring formed by bonding to each other may have a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 3 to 18 carbon atoms, R a3 and R a4 Each independently represents a group represented by the following formula (ZB), In formula (ZB), T 1 ~T 3 Respectively represent -CR e12 = or nitrogen atom, R e12 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a silyl group, a halogen atom or a cyano group, and R f3 and R f4 each independently represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, or a heteroaryl group having 3 to 18 carbon atoms which may have an alkyl group having 1 to 10 carbon atoms, a halogen atom, an alkoxy group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cyano group, *Indicates bonding position.

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