Photoelectric conversion element, imaging element, method for manufacturing imaging element, optical sensor, and compound
The photoelectric conversion element with specific compounds and organic semiconductors reduces the dependence on electric field strength for blue-green light, improving the response speed and performance of imaging and optical sensors.
Patent Information
- Application Number
- PCT/JP2025/029771
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-08-28
- Filing Date
- 2025-08-25
- Publication Date
- 2026-03-05
AI Technical Summary
Existing photoelectric conversion elements exhibit a significant dependence of response speed on electric field strength for blue-green light, which hinders their performance in image sensors and optical sensors.
A photoelectric conversion element configuration with a conductive film, a photoelectric conversion film containing specific compounds represented by formulas (1-1) or (1-2), and a transparent conductive film, which includes an n-type organic semiconductor and may have bulk heterostructures, reducing the dependence on electric field strength.
The solution provides a photoelectric conversion element with improved response speed to blue-green light that is less dependent on electric field strength, enhancing the performance of imaging elements and optical sensors.
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Figure JP2025029771_05032026_PF_FP_ABST
Abstract
Description
Photoelectric conversion element, imaging element, imaging element manufacturing method, optical sensor, compound
[0001] The present invention relates to a photoelectric conversion element, an imaging element, a method for manufacturing an imaging element, an optical sensor, and a compound.
[0002] In recent years, development of elements having a photoelectric conversion film has progressed as organic electronic devices. For example, Patent Document 1 discloses a photoelectric conversion element containing a dye compound having the following structure:
[0003]
[0004] International Publication No. 2022 / 207312
[0005] On the other hand, with the demand for improved performance of image sensors, optical sensors, and the like, there is a demand for photoelectric conversion elements that exhibit excellent characteristics. One of the characteristics required for a photoelectric conversion element is, for example, a small dependency of the response speed to blue-green light on electric field strength. In response to this demand, the present inventors fabricated and investigated a photoelectric conversion element using the compound disclosed in Patent Document 1, and found that the dependency of the response speed to blue-green light on electric field strength needed to be improved. The blue-green light referred to above refers to light with a wavelength of 400 to 600 nm.
[0006] Therefore, an object of the present invention is to provide a photoelectric conversion element having a response speed to blue-green light that has little dependence on electric field strength. Another object of the present invention is to provide an imaging element, a manufacturing method of an imaging element, an optical sensor, and a compound related to the photoelectric conversion element.
[0007] As a result of extensive research into solving the above problems, the present inventors have found that the problems can be solved by the following configuration.
[0008] [1] A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains a compound represented by formula (1-1) or formula (1-2) described below. [2] The above D 1 and the above D 2[3] The photoelectric conversion element according to [1], wherein each independently represents a group selected from the group consisting of groups represented by formulas (2) to (10) described below. 1 and the above D 2 [4] The photoelectric conversion element according to any one of [1] to [3], wherein m1 and m2 each independently represent a group selected from the group consisting of groups represented by formulas (3) to (10) described below. [5] The photoelectric conversion element according to any one of [1] to [3], wherein m1 and m2 each independently represent 0. [6] In formula (1-1), X 1 ~ Above X 4 However, both are -C (=Y X )-, and the above Y X each independently represents an oxygen atom or ═CR W3 R W4 In the formula (1-2), the Y 1 ~ Above Y 4 each independently represents an oxygen atom or ═CR W3 R W4[6] The photoelectric conversion element according to any one of [1] to [5], wherein the compound represented by formula (1-1) is a compound represented by any one of formulas (1-3) to (1-6) described below. [7] The photoelectric conversion element according to any one of [1] to [6], wherein the photoelectric conversion film further contains an n-type organic semiconductor, and wherein the photoelectric conversion film has a bulk heterostructure formed by mixing the compound and the n-type organic semiconductor. [8] The photoelectric conversion element according to [7], wherein the n-type organic semiconductor contains fullerenes selected from the group consisting of fullerenes and derivatives thereof. [9] The photoelectric conversion element according to any one of [1] to [8], wherein the photoelectric conversion film further contains a p-type organic semiconductor.
[10] The photoelectric conversion element according to any one of [1] to [9], wherein the photoelectric conversion film further contains a dye.
[11] The photoelectric conversion element according to any one of [1] to
[10] , which has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
[12] An imaging element having the photoelectric conversion element according to any one of [1] to
[11] .
[13] An optical sensor having the photoelectric conversion element according to any one of [1] to
[11] .
[14] A method for manufacturing an imaging element, comprising a step of manufacturing the photoelectric conversion element according to [1] to
[11] .
[15] A compound represented by formula (1-1) described later.
[16] In formula (1-1), 1 ~ Above X 4 However, both are -C (=Y X )-, and the above Y X each independently represents an oxygen atom or ═CR W3 R W4
[17] The compound according to
[15] , wherein the compound represented by the formula (1-1) is a compound represented by any one of the formulas (1-3) to (1-6) described below.
[18] The compound represented by the formula (1-2) described below.
[19] In the formula (1-2), the Y 1 ~ Above Y 4 each independently represents an oxygen atom or ═CR W3 R W4
[20] The compound according to
[18] or
[19] , wherein m1 and m2 each represent 0.
[0009] According to the present invention, a photoelectric conversion element having a response speed to blue-green light that has little dependence on electric field strength can be provided. The present invention also provides an imaging element, a method for manufacturing an imaging element, an optical sensor, and a compound related to the photoelectric conversion element.
[0010] 1 is a schematic cross-sectional view showing an example of the configuration of a photoelectric conversion element. 2 is a schematic cross-sectional view showing an example of the configuration of a photoelectric conversion element. 3 is a view showing the ultraviolet-visible absorption spectrum of compound B-1.
[0011] The present invention will be described in detail below. The following description of the components may be based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.
[0012] The meaning of each description in this specification is as follows. In this specification, a numerical range expressed using "to" means a range that includes the numerical values written before and after "to" as the lower and upper limits. In this specification, a hydrogen atom may be a protist atom (a normal hydrogen atom) or a deuterium atom (for example, a deuterium atom, etc.).
[0013] In this specification, with respect to compounds that may have geometric isomers (cis-trans isomers), the general formula or structural formula representing the compound may be described in only one of the cis- and trans-forms for convenience. Even in such cases, unless otherwise specified, the form of the compound is not limited to either the cis- or trans-form, and the compound may be in either the cis- or trans-form.
[0014] In this specification, with respect to a compound having an asymmetric atom, the general formula or structural formula representing the compound may be described without distinguishing between stereoisomers for convenience. Even in such a case, unless otherwise specified, the form of the compound is not limited to any one form, and may be any one form or a mixture. For example, unless otherwise specified, a compound having an asymmetric carbon atom may be either an S-form or an R-form, or a mixture thereof.
[0015] Unless otherwise specified, the bonding direction of a divalent group (e.g., -CO-O-) represented in this specification is not limited. For example, when Y is -CO-O- in a compound represented by the formula "X-Y-Z," the compound may be either "X-O-CO-Z" or "X-CO-O-Z."
[0016] The symbol "*" shown in a chemical formula represents a bonding position unless otherwise specified. In this specification, when there are multiple substituents and linking groups, etc. (hereinafter also referred to as "substituents, etc.") represented by a specific symbol, or when multiple substituents, etc. are specified at the same time, it means that the respective substituents, etc. may be the same or different from each other. This also applies to the specification of the number of substituents, etc. In this specification, unless otherwise specified, "substituents" include, for example, groups exemplified as the substituent W described below.
[0017] (Substituent W) The substituent W in this specification will be described. Examples of the substituent W include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, an aryl group, a heterocyclic group (a heteroaryl group or an aliphatic heterocyclic group), a cyano group, a nitro group, an alkoxy group, an aryloxy group, a silyl group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryl ... Examples of the substituent W include an anyloxy group, a primary, secondary, or tertiary amino group (including an anilino group), an alkylthio group, an arylthio group, a heterocyclic thio group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a phosphono group, a carboxy group, a phosphate group, a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, and a boronic acid group. Furthermore, each of the above groups may further have a substituent (e.g., one or more of the above groups, etc.), if possible. For example, an alkyl group, which may have a substituent, is also included as one form of the substituent W. Furthermore, when the substituent W has a carbon atom, the number of carbon atoms contained in the substituent W is, for example, 1 to 20. The number of atoms other than hydrogen atoms contained in the substituent W is, for example, 1 to 30. The specific compounds described below may have, as substituents, a carboxy group, a salt of a carboxy group, a salt of a phosphate group, a sulfonic acid group, a salt of a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, a boronic acid group (-B(OH) 2 ) and / or preferably has no primary amino groups.
[0018] In this specification, the aliphatic hydrocarbon group may be linear, branched, or cyclic. Examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group. Furthermore, in this specification, unless otherwise specified, the number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6. The alkyl group may be linear, branched, or cyclic. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclopropyl group, and a cyclopentyl group. Furthermore, the alkyl group may be a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have these ring structures as partial structures. In the alkyl group that may have a substituent, examples of the substituent that the alkyl group may have include the groups exemplified for the substituent W. Of these, an aryl group (preferably having 6 to 18 carbon atoms, more preferably having 6 carbon atoms), a heteroaryl group (preferably having 3 to 18 carbon atoms, more preferably having 4 to 6 carbon atoms), or a halogen atom (preferably a fluorine atom or a chlorine atom) is preferred.
[0019] In this specification, unless otherwise specified, the alkyl group moiety in an alkoxy group is preferably the above-mentioned alkyl group. The alkyl group moiety in an alkylthio group is preferably the above-mentioned alkyl group. In an alkoxy group which may have a substituent, examples of the substituent that the alkoxy group may have include the same as the substituent in an alkyl group which may have a substituent. In an alkylthio group which may have a substituent, examples of the substituent that the alkylthio group may have include the same as the substituent in an alkyl group which may have a substituent.
[0020] In this specification, unless otherwise specified, the alkenyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkenyl group is preferably 2 to 20. In the optionally substituted alkenyl group, examples of the substituent that the alkenyl group may have include the same as the substituents in the optionally substituted alkyl group. In this specification, unless otherwise specified, the alkynyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkynyl group is preferably 2 to 20. In the optionally substituted alkynyl group, examples of the substituent that the alkynyl group may have include the same as the substituents in the optionally substituted alkyl group.
[0021] In this specification, unless otherwise specified, an aromatic ring or an aromatic ring constituting an aromatic ring group may be either a monocyclic ring or a polycyclic ring (e.g., 2 to 6 rings, etc.). A monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as a ring structure. A polycyclic (e.g., 2 to 6 rings, etc.) aromatic ring is an aromatic ring having a plurality of (e.g., 2 to 6, etc.) condensed aromatic ring structures as a ring structure. The number of ring members in the aromatic ring is preferably 5 to 15. The aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring. When the aromatic ring is an aromatic heterocyclic ring, the number of heteroatoms contained as ring member atoms is, for example, 1 to 10. Examples of the heteroatom include a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, and a fluorene ring.Examples of the aromatic heterocycle include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring (for example, a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring), a tetrazine ring (for example, a 1,2,4,5-tetrazine ring), a quinoxaline ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a naphthopyrrole ring, a naphthofuran ring, a naphthothiophene ring, a naphthoimidazole ring, a naphthoxazole ring, a pyrroloimidazole ring (for example, a 5H-pyrrolo[1,2-a]imidazole ring), an imidazooxazole ring (for example, an imidazo[2,1-b]oxazole ring), a thiazole ring, a quinoxaline ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, a naphthopyrrole ring, a naphthofuran ring, a naphthothiophene ring, a naphthoimidazole ring, a naphthoxazole ring, a pyrroloimidazole ring (for example, a 5H-pyrrolo[1,2-a]imidazole ring), an imidazooxazole ring (for example, an imidazo[2,1-b]oxazole ring), a thiazole ring, ... Enothiazole ring (for example, thieno[2,3-d]thiazole ring, etc.), benzothiadiazole ring, benzodithiophene ring (for example, benzo[1,2-b:4,5-b']dithiophene ring, etc.), thienothiophene ring (for example, thieno[3,2-b]thiophene ring, etc.), thiazolothiazole ring (for example, thiazolo[5,4-d]thiazole ring, etc.), naphthodithiophene ring (for example, naphtho[2,3-b :6,7-b']dithiophene ring, naphtho[2,1-b:6,5-b']dithiophene ring, naphtho[1,2-b:5,6-b']dithiophene ring, and 1,8-dithiadicyclopenta[b,g]naphthalene ring, etc.), benzothienobenzothiophene ring, dithieno[3,2-b:2',3'-d]thiophene ring, and 3,4,7,8-tetrathiadicyclopenta[a,e]pentalene ring.
[0022] As used herein, the term "aromatic ring group" includes, for example, a group obtained by removing one or more hydrogen atoms (e.g., 1 to 5) from the above-mentioned aromatic ring. As used herein, the term "aryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic hydrocarbon ring among the above-mentioned aromatic rings. As used herein, the term "heteroaryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings. As used herein, the term "arylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above-mentioned aromatic rings. As used herein, the term "heteroarylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings. In the optionally substituted aromatic ring, optionally substituted aromatic ring group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted arylene group, and optionally substituted heteroarylene group, the types of substituents that these may have include, for example, the groups exemplified for the substituent W. In addition, when the compound has a substituent, the number of the substituents may be one or more (for example, 1 to 4).
[0023] As used herein, the term "non-aromatic ring" refers to a ring structure that is not aromatic, and examples thereof include an aliphatic hydrocarbon ring and an aliphatic heterocycle. Examples of the aliphatic hydrocarbon ring include cycloalkanes, cycloalkenes, and cycloalkynes. As used herein, the term "aliphatic heterocyclic group" refers to, for example, a group obtained by removing one hydrogen atom from the aliphatic heterocycle. As used herein, the number of ring members in the aliphatic heterocyclic group is preferably 5 to 20, more preferably 5 to 12, and even more preferably 6 to 8. Examples of heteroatoms contained in the aliphatic heterocyclic group include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, with a sulfur atom, an oxygen atom, or a nitrogen atom being preferred. Examples of the aliphatic heterocycle constituting the aliphatic heterocyclic group include a pyrrolidine ring, an oxolane ring (tetrahydrofuran ring), a thiolane ring, a piperidine ring, a tetrahydropyran ring, a thiane ring (pentamethylene sulfide ring), a piperazine ring, a morpholine ring, a quinuclidine ring, an azetidine ring, an oxetane ring, an aziridine ring, a dioxane ring, and a γ-butyrolactone ring.
[0024] [Photoelectric Conversion Element] The photoelectric conversion element of the present invention is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film contains a compound represented by formula (1-1) or formula (1-2) (hereinafter also referred to as a "specific compound").
[0025] Although the reason why the photoelectric conversion element having the above configuration can solve the problems of the present invention is not entirely clear, the inventors speculate as follows. The following speculation does not limit the mechanism by which the effect is obtained. In other words, even if the effect is obtained by a mechanism other than the one described below, it is still within the scope of the present invention. The specific compound is a so-called DAD-type dye compound having an acceptor moiety (A) and two donor moieties (D) bonded via the acceptor moiety (A). The specific compound has a predetermined donor structure and an acceptor structure (in particular, the aromatic ring group constituting the donor moiety has, as a substituent, an alkyl group bonded to a carbon atom that is a ring atom of the aromatic ring group under predetermined conditions), thereby preventing excessive aggregation of the specific compounds in the photoelectric conversion film. As a result, efficient charge separation can be achieved even at low electric field strength, and carriers can move efficiently, which is thought to reduce the electric field strength dependence of the response speed. Hereinafter, the photoelectric conversion element of the present invention having a smaller electric field strength dependence of the response speed to blue-green light is also referred to as having "superior effects of the present invention."
[0026] FIG. 1 shows a cross-sectional schematic diagram of one embodiment of the photoelectric conversion element of the present invention. The photoelectric conversion element 10a shown in FIG. 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 functioning as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and a transparent conductive film (hereinafter also referred to as the "upper electrode") 15 functioning as an upper electrode are stacked in this order. FIG. 2 shows an example of the configuration of another photoelectric conversion element. The photoelectric conversion element 10b shown in FIG. 2 has a configuration in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are stacked in this order on a lower electrode 11. Note that the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in FIGS. 1 and 2 may be changed as appropriate depending on the application and characteristics.
[0027] In the photoelectric conversion element 10a (or 10b), it is preferable that light is incident on the photoelectric conversion film 12 through the upper electrode 15. When the photoelectric conversion element 10a (or 10b) is used, a voltage can be applied. In this case, the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and a voltage of 1×10 is applied between the pair of electrodes. -5 ~1 x 10 7 In terms of performance and power consumption, it is preferable to apply a voltage of 1×10 V / cm. -4 ~1 x 10 7 V / cm is more preferable, and 1×10 -3 ~5 x 10 6 V / cm is more preferable. Regarding the voltage application method, it is preferable to apply the voltage so that the electron blocking film 16A side serves as the cathode and the photoelectric conversion film 12 side serves as the anode in FIGS. 1 and 2. When the photoelectric conversion element 10a (or 10b) is used as a photosensor or incorporated into an imaging element, a voltage can be applied in a similar manner. As will be described in detail later, the photoelectric conversion element 10a (or 10b) can be suitably used as an imaging element. The configuration of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.
[0028] [Photoelectric Conversion Film] The photoelectric conversion element has a photoelectric conversion film.
[0029] <Specific Compound> The photoelectric conversion film contains a compound represented by formula (1-1) or a compound represented by formula (1-2) (specific compound).
[0030]
[0031] (Compound represented by formula (1-1)) In formula (1-1), D 1 and D 2each independently represents a monocyclic or condensed aromatic ring group which may have a substituent. However, the aromatic ring group has at least one alkyl group (hereinafter also referred to as "specific alkyl group") bonded to a carbon atom which is a ring member atom of the aromatic ring group as a substituent, and when the aromatic ring group has one alkyl group as the substituent, the number of carbon atoms of the alkyl group is 2 or more (in other words, when the aromatic ring group has only one specific alkyl group, the number of carbon atoms of the specific alkyl group is 2 or more), and when the aromatic ring group has two or more alkyl groups as the substituent, the total number of carbon atoms of the two or more alkyl groups is 2 or more (in other words, when the aromatic ring group has two or more specific alkyl groups, the total number of carbon atoms of the two or more specific alkyl groups is 2 or more). In the aromatic ring group, when two adjacent ring atoms are carbon atoms and each of the carbon atoms has an alkyl group (specific alkyl group) bonded to it, the alkyl groups may be bonded to each other to form a ring structure (i.e., the two carbon atoms to which the specific alkyl groups are bonded and the alkylene chain formed by the specific alkyl groups being bonded to each other may form a ring structure). When the specific alkyl groups are bonded to each other to form a ring structure, the aromatic ring group is considered to have two specific alkyl groups. Furthermore, the number of carbon atoms in the alkylene chain formed by the specific alkyl groups being bonded to each other (i.e., the alkylene chain connecting the two carbon atoms to which the specific alkyl groups are bonded) is considered to be the total number of carbon atoms in the two specific alkyl groups.
[0032] The specific alkyl group may be linear, branched, or cyclic. The lower limit of the number of carbon atoms in the specific alkyl group is preferably 1 or more, and more preferably 3 or more, since the aggregation suppression performance is not likely to be excellent even during high-speed film formation (better manufacturability). The upper limit of the number of carbon atoms in the specific alkyl group is, for example, 10 or less. Specific examples of the number of carbon atoms in the specific alkyl group are preferably 1 to 10, more preferably 1 to 7, and even more preferably 1 to 4. When the aromatic ring group has only one specific alkyl group, the upper limit of the number of carbon atoms in the specific alkyl group is preferably 10 or less, more preferably 7 or less, and even more preferably 4 or less. When the aromatic ring group has two or more specific alkyl groups, the upper limit of the total number of carbon atoms in the two or more specific alkyl groups is preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, particularly preferably 6 or less, and most preferably 4 or less. The number of specific alkyl groups in the aromatic ring group is not particularly limited, and may be, for example, 1 to 4, with 1 to 3 being preferred, and 1 or 2 being more preferred.
[0033] The specific alkyl group may further have a substituent or may not have a substituent, but it is preferable that the specific alkyl group has no substituent, in that the effects of the present invention are more likely to be excellent. Examples of the substituent include the groups exemplified as the substituent W above.
[0034] Specific examples of the specific alkyl group include a linear alkyl group having 1 to 4 carbon atoms which may have a substituent, a branched alkyl group having 3 to 7 carbon atoms which may have a substituent, and a cyclic alkyl group having 3 to 6 carbon atoms which may have a substituent.
[0035] The aromatic ring group may further have a substituent other than the specific alkyl group. Examples of the substituent include the groups exemplified by the substituent W. More specific examples of the substituent include an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 ring members which may have a substituent, an alkoxy group having 1 to 3 carbon atoms which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, a cyano group, and a halogen atom.
[0036] D1 and D 2 In particular, each independently preferably represents a group selected from the group consisting of groups represented by formulas (2) to (10), and more preferably represents a group selected from the group consisting of groups represented by formulas (3) to (10).
[0037]
[0038] In formula (2), T 21 ~T 25 are each independently -CR 21 = or -N=. 21 ~T 25 In the formula, -N= is preferably 0 to 2. 21 represents a hydrogen atom or a substituent. 21 If there are multiple R 21 may be the same or different. * indicates a bonding position. 21 ~T 25 At least one of 21 is an alkyl group 21 = (i.e., the above R 21 corresponds to a specific alkyl group.), T 21 ~T 25 Only one of them is R 21 is an alkyl group 21 =, the above R 21 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 21 ~T 25 Two or more of the following are R 21 is an alkyl group 21 When the formula represents ≡ =, two or more of the above R 21 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 21 ~T 25 Medium, T 21 ~T 25 Two adjacent ones of 21 is an alkyl group 21 When the group represents =, the alkyl groups may be linked to each other to form a ring structure.
[0039] In formula (3), X 31 represents a sulfur atom, an oxygen atom, or —NR X1 - represents X 31 is preferably a sulfur atom in that the effects of the present invention are more excellent. 31 ~T 33 are each independently -CR 31 = or -N=. 31 ~T 33 In the formula, -N= is preferably 0 to 1. X1 and R 31 Each independently represents a hydrogen atom or a substituent. 31 If there are multiple R 31 may be the same or different. * indicates a bonding position. 31 ~T 33 At least one of 31 is an alkyl group 31 = (i.e., the above R 31 corresponds to a specific alkyl group.), T 31 ~T 33 Only one of them is R 31 is an alkyl group 31 =, the above R 31 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 31 ~T 33 Two or more of the following are R 31 is an alkyl group 31 When the formula represents ≡ =, two or more of the above R 31 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 31 ~T 33 Medium, T 31 ~T 33 Two adjacent ones of 31 is an alkyl group 31 When the group represents =, the alkyl groups may be linked to each other to form a ring structure.
[0040] In formula (4), T 41 ~T 47 are each independently -CR 41 = or -N=.41 ~T 47 In the formula, the number of -N= is preferably 0 to 3, and more preferably 0 to 2. 41 represents a hydrogen atom or a substituent. 41 If there are multiple R 41 may be the same or different. * indicates a bonding position. 41 ~T 47 At least one of 41 is an alkyl group 41 = (i.e., the above R 41 corresponds to a specific alkyl group.), T 41 ~T 47 Only one of them is R 41 is an alkyl group 41 =, the above R 41 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 41 ~T 47 Two or more of the following are R 41 is an alkyl group 41 When the formula represents ≡ =, two or more of the above R 41 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 41 ~T 47 Medium, T 41 ~T 47 Two adjacent ones of 41 is an alkyl group 41 When the group represents =, the alkyl groups may be linked to each other to form a ring structure.
[0041] In formula (5), X 51 represents a sulfur atom, an oxygen atom, or —NR X1 - represents X 51 is preferably a sulfur atom in that the effects of the present invention are more excellent. 51 ~T 55 are each independently -CR 51 = or -N=. 51 ~T 55 In the formula, -N= is preferably 0 to 2. X1 and R 51Each independently represents a hydrogen atom or a substituent. 51 If there are multiple R 51 may be the same or different. * indicates a bonding position. 51 ~T 55 At least one of 51 is an alkyl group 51 = (i.e., the above R 51 corresponds to a specific alkyl group.), T 51 ~T 55 Only one of them is R 51 is an alkyl group 51 =, the above R 51 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 51 ~T 55 Two or more of the following are R 51 is an alkyl group 51 When the formula represents ≡ =, two or more of the above R 51 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 51 ~T 55 Medium, T 51 ~T 55 Two adjacent ones of 51 is an alkyl group 51 When the group represents =, the alkyl groups may be linked to each other to form a ring structure.
[0042] In formula (6A), X 61 represents a sulfur atom, an oxygen atom, or —NR X1 - represents X 61 is preferably a sulfur atom in that the effects of the present invention are more excellent. 6a and Y 6b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 Y= or -N= is preferable in that the effect of the present invention is more excellent. 6a and Y 6b One of these represents a sulfur atom, and the other represents CR Y1 Preferably, R represents = or -N=. X1 , R Y1, R 61 , and R 62 each independently represents a hydrogen atom or a substituent. * represents a bonding position. However, the group represented by formula (6A) satisfies any one of the following requirements 6AA to 6AD.
[0043] ・Requirement 6AA: Y 6a and Y 6b One of them is -CR Y1 =, and R Y1 is an alkyl group (i.e., the above R Y1 represents a specific alkyl group, and R 61 and R 62 represents a group other than an alkyl group. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and R 61 and R 62 At least one of R represents an alkyl group (i.e., R is an alkyl group). 61 and R 62 At least one of the R 61 and R 62 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and 61 and R 62 When both of Y and Y represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 and R 62 At least one of the R represents an alkyl group. Y1 and at least one of the R 61 and R 62 The total number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6bone of which represents -N=, and R 61 and R 62 At least one of the above R represents an alkyl group. 61 and R 62 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and 61 and R 62 When both of them represent an alkyl group, the total number of carbon atoms in the alkyl groups is 2 or more.
[0044] In formula (6B), X 61 represents a sulfur atom, an oxygen atom, or —NR X1 - represents X 61 is preferably a sulfur atom in that the effects of the present invention are more excellent. 6a and Y 6b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 Y= or -N= is preferable in that the effect of the present invention is more excellent. 6a and Y 6b One of these represents a sulfur atom, and the other represents CR Y1 Preferably, R represents = or -N=. X1 , R Y1 , and R 61 each independently represents a hydrogen atom or a substituent. * represents a bonding position. However, the group represented by formula (6B) satisfies any one of the following requirements 6BA to 6BD.
[0045] ・Requirement 6BA: Y 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group (i.e., the above R Y1 corresponds to a specific alkyl group, and R 61 represents a group other than an alkyl group. Y1 The alkyl group represented by the formula (I) has 2 or more carbon atoms. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and R 61is an alkyl group (i.e., the above R 61 represents a specific alkyl group. 61 The alkyl group represented by the formula (I) has 2 or more carbon atoms. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 represents an alkyl group. Y1 and the alkyl group represented by the above R 61 The total number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b one of which represents -N=, and R 61 represents an alkyl group. 61 The alkyl group represented by the formula (I) has 2 or more carbon atoms.
[0046] In formula (7), X 71 represents a sulfur atom, an oxygen atom, -NR X1 -, -C(R X2 ) 2 -, or -Si(R X3 ) 2 - represents X 71 is preferably a sulfur atom in that the effects of the present invention are more excellent. 7a and Y 7b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or =N-. In terms of the effects of the present invention, Y 7a and Y 7b One of these represents a sulfur atom, and the other represents CR Y1 It is preferred that Ar represents = or -N=. 7 represents a monocyclic or condensed aromatic ring which may have a substituent. X1 , R X2 , R X3 , and R Y1 each independently represents a hydrogen atom or a substituent, provided that the group represented by formula (7) satisfies any one of the following requirements 7A to 7J.
[0047] ・Requirement 7A: Y 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group (i.e., the above R Y1 corresponds to a specific alkyl group.), X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 - (i.e., the above R X2 corresponds to a specific alkyl group, and Ar 7 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the groups Y represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of the group has an alkyl group as a substituent (i.e., Ar 7 The alkyl group in the above corresponds to a specific alkyl group.7 The alkyl group in 7 When Ar has only one alkyl group as a substituent on a carbon atom that is a ring atom, the alkyl group has two or more carbon atoms, and 7 The alkyl group in 7 When Ar has two or more alkyl groups as substituents on the carbon atoms that are ring atoms, the total number of carbon atoms in the two or more alkyl groups is two or more. 7 In the formula (7), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. Y1 and the alkyl group represented by the above R X2 The total number of carbon atoms in the alkyl groups represented by the formula (I) is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. Y1 and the alkyl group represented by the above Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7In the formula (7), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. X2 and the alkyl group represented by the above Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. Y1 the alkyl group represented by the above R X2 and the alkyl group represented by the above Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
[0048] ・Requirement 7H: Y 7a and Y7b One of the groups represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the above groups represent an alkyl group, the total number of carbon atoms of the alkyl groups is 2 or more. 7a and Y 7b One of the groups represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 7 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, and 7 When Ar has two or more alkyl groups, the total number of carbon atoms of the two or more alkyl groups is two or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of the groups represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. X2 and the alkyl group represented by the above Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
[0049] In formula (8), X 81 represents a sulfur atom, an oxygen atom, -NR X1 -, -C(R X2 ) 2 -, or -Si(R X3 ) 2 - represents X 81 is preferably a sulfur atom in that the effects of the present invention are more excellent. 8 represents a monocyclic or condensed aromatic ring which may have a substituent. 81 ~T 83 are each independently -CR 81 = or -N=. 81 ~T 83 In the formula, -N= is preferably 0 to 2. X1 , R X2 , R X3 , and R 81 Each independently represents a hydrogen atom or a substituent. 81 If there are multiple R 81 may be the same or different. * indicates a bonding position. However, the group represented by formula (8) satisfies any one of the following requirements 8A to 8G.
[0050] ・Requirement 8A: T 81 ~T 83 At least one of 81 is an alkyl group 81 = (i.e., the above R 81 corresponds to a specific alkyl group.), X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 81 ~T 83 Only one of the 81is an alkyl group 81 =, the above R 81 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 81 ~T 83 Two or more of the 81 is an alkyl group 81 When the formula represents ≡ =, two or more of the above R 81 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When T represents ≡ ... 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 - (i.e., the above R X2 corresponds to a specific alkyl group, and Ar 8 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the above groups represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atom that is a ring atom of the group has an alkyl group as a substituent (i.e., Ar 8The alkyl group in the above corresponds to a specific alkyl group. 8 The alkyl group in 8 When Ar has only one alkyl group as a substituent on a carbon atom that is a ring atom, the alkyl group has two or more carbon atoms, and 8 The alkyl group in 8 When Ar has two or more alkyl groups as substituents on the carbon atoms that are ring atoms, the total number of carbon atoms in the two or more alkyl groups is two or more. 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. 81 and the alkyl group represented by the above R X2 The total number of carbon atoms in the alkyl group represented by T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When the group represents =, the alkyl groups may be linked to each other to form a ring structure.
[0051] ・Requirement 8E: T 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 )2 represents a group other than -, and Ar 8 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. 81 and the alkyl group represented by the above Ar 8 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When Ar represents ═ ... 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. X2 and the alkyl group represented by the above Ar 8 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 )2 -, and Ar 8 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. 81 the alkyl group represented by the above R X2 and the alkyl group represented by the above Ar 8 The carbon atom which is a ring atom of T has as a substituent an alkyl group having two or more carbon atoms. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When Ar represents ═ ... 8 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
[0052] In formula (9), X 91 represents a sulfur atom, an oxygen atom, or —NR X1 - represents X 91 is preferably a sulfur atom in that the effects of the present invention are more excellent. 9 represents a monocyclic or condensed aromatic ring which may have a substituent. 91 ~T 93 are each independently -CR 91 = or -N=. 91 ~T 93 In the formula, -N= is preferably 0 to 1. X1 and R 91 represents a hydrogen atom or a substituent. 91 If there are multiple R 91 may be the same or different. * indicates a bonding position. However, the group represented by formula (9) satisfies any one of the following requirements 9A to 9C.
[0053] ・Requirement 9A: T 91 ~T 93 At least one of 91 is an alkyl group91 = (i.e., the above R 91 corresponds to a specific alkyl group, and Ar 9 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 91 ~T 93 Only one of the 91 is an alkyl group 91 =, the above R 91 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 91 ~T 93 Two or more of the 91 is an alkyl group 91 When the formula represents ≡ =, two or more of the above R 91 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 91 ~T 93 Medium, T 91 ~T 93 Two adjacent ones of 91 is an alkyl group 91 When T represents ≡ ... 91 ~T 93 But, R 91 is an alkyl group 91 represents a group other than . 9 The carbon atom that is a ring atom of the group has an alkyl group as a substituent (i.e., Ar 9 The alkyl group in the above corresponds to a specific alkyl group. 9 The alkyl group in 9 When Ar has only one alkyl group as a substituent on a carbon atom that is a ring atom, the alkyl group has two or more carbon atoms, and 9 The alkyl group in 9 When Ar has two or more alkyl groups as substituents on the carbon atoms that are ring atoms, the total number of carbon atoms in the two or more alkyl groups is two or more. 9In the formula (9), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 91 ~T 93 At least one of 91 is an alkyl group 91 = and Ar 9 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. 91 and the alkyl group represented by the above Ar 9 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 91 ~T 93 Medium, T 91 ~T 93 Two adjacent ones of 91 is an alkyl group 91 When Ar represents ═ ... 9 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
[0054] In formula (10), Y 10a and Y 10b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or =N-. In terms of the effects of the present invention, Y 10a and Y 10b One of these represents a sulfur atom, and the other represents CR Y1 It is preferred that Ar represents = or -N=. 10 represents a monocyclic or condensed aromatic ring which may have a substituent. 10 and T 11 are each independently -CR 101 = or -N=. X1 , R 101 , and R Y1 Each independently represents a hydrogen atom or a substituent.101 If there are multiple R 101 may be the same or different. * indicates a bonding position. However, the group represented by formula (10) satisfies any one of the following requirements 10A to 10J.
[0055] ・Requirement 10A: Y 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group (i.e., the above R Y1 corresponds to a specific alkyl group.), T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = (i.e., the above R 101 corresponds to a specific alkyl group, and Ar 10 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 10 and T 11 Only one of the 101 is an alkyl group 101 =, the above R 101 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 10 and T 11 Both of them are R 101 is an alkyl group 101 =, the above two R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of the group has an alkyl group as a substituent (i.e., Ar 10 The alkyl group in the above corresponds to a specific alkyl group. 10 The alkyl group in 10 When Ar has only one alkyl group as a substituent on a carbon atom that is a ring atom, the alkyl group has two or more carbon atoms, and 10 The alkyl group in 10 When Ar has two or more alkyl groups as substituents on the carbon atoms that are ring atoms, the total number of carbon atoms in the two or more alkyl groups is two or more. 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of the above R do not have alkyl groups as substituents. Y1 and the alkyl group represented by the above R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. Y1 and the alkyl group represented by the above Ar 10 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. 101 and the alkyl group represented by the above Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. Y1 the alkyl group represented by the above R 101 and the alkyl group represented by the above Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
[0056] ・Requirement 10H: Y 10a and Y 10b One of the two represents -N=, and T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 10 and T 11 Only one of the 101 is an alkyl group 101 =, the above R 101 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 10 and T11 Both of them are R 101 is an alkyl group 101 =, the above two R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 10 When Ar has only one alkyl group as a substituent, the alkyl group has two or more carbon atoms, and 10 When Ar has two or more alkyl groups as substituents, the total number of carbon atoms of the two or more alkyl groups is two or more. 10 In the case where adjacent carbon atoms in the ring have alkyl groups bonded to them, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of the above R has an alkyl group as a substituent. 101 and the alkyl group represented by the above Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101When Ar represents ═ ... 10 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
[0057] In the groups represented by formulas (2) to (10), the specific alkyl group may be linear, branched, or cyclic. The lower limit of the number of carbon atoms in the specific alkyl group is preferably 1 or more, and more preferably 3 or more, in terms of the fact that aggregation suppression performance is not easily improved even during high-speed film formation (better manufacturability). The upper limit of the number of carbon atoms in the specific alkyl group is, for example, 10 or less. Specific examples of the number of carbon atoms in the specific alkyl group are preferably 1 to 10, more preferably 1 to 7, and even more preferably 1 to 4. When the groups represented by formulas (2) to (10) have only one specific alkyl group, the upper limit of the number of carbon atoms in the specific alkyl group is preferably 10 or less, more preferably 7 or less, and even more preferably 4 or less. When the groups represented by formulas (2) to (10) have two or more specific alkyl groups, the upper limit of the total number of carbon atoms in the two or more specific alkyl groups is preferably 20 or less, more preferably 15 or less, even more preferably 10 or less, particularly preferably 6 or less, and most preferably 4 or less. The number of specific alkyl groups in the groups represented by formulas (2) to (10) is not particularly limited, and may be, for example, 1 to 4, preferably 1 to 3, and more preferably 1 or 2.
[0058] Specific examples of the specific alkyl group include a linear alkyl group having 1 to 4 carbon atoms which may have a substituent, a branched alkyl group having 3 to 7 carbon atoms which may have a substituent, and a cyclic alkyl group having 3 to 6 carbon atoms which may have a substituent.
[0059] In formulas (2) to (10), R X1 and R X3 Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W. X1 and R X3Among these, it is preferable that each independently represent a hydrogen atom or a substituent selected from the group consisting of a linear alkyl group having 1 to 3 carbon atoms which may have a substituent, a branched alkyl group having 3 to 7 carbon atoms which may have a substituent, a cyclic alkyl group having 3 to 6 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent. Examples of the substituent include the groups exemplified for the substituent W.
[0060] In formulas (2) to (10), R X2 Examples of the substituent represented by the formula (I) include the groups exemplified as the substituent W. X2 In particular, each independently represents a hydrogen atom or a substituent selected from the group consisting of a linear alkyl group having 1 to 3 carbon atoms which may have a substituent, a branched alkyl group having 3 to 7 carbon atoms which may have a substituent, a cyclic alkyl group having 3 to 6 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms which may have a substituent, or R X2 Preferably, R are linked to each other to form a ring structure. X2 The ring structure formed by linking together is not particularly limited, but an aliphatic ring (an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring) is preferred.
[0061] In formulas (2) to (10), R Y1 , R 21 , R 31 , R 41 , R 51 , R 61 , R 62 , R 81 , R 91 , and R 101 and Ar 7 ~Ar 10 Examples of the substituent that may be possessed by include the groups exemplified as the substituent W.
[0062] The above-mentioned R Y1 , R 21 , R 31 , R 41 , R 51 , R 61 , R 62 , R 81 , R91 , and R 101 are each independently preferably a hydrogen atom, or a substituent selected from the group consisting of a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 7 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 ring members which may have a substituent, an alkoxy group having 1 to 3 carbon atoms which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, a cyano group, and a halogen atom.
[0063] Ar 7 ~Ar 10 Among these, the substituents which may be possessed by the group represented by the formula (I) are preferably each independently selected from the group consisting of a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 7 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 ring members which may have a substituent, an alkoxy group having 1 to 3 carbon atoms which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, a cyano group, and a halogen atom.
[0064] Specific examples of the group represented by formula (2) are shown below, but the group represented by formula (2) is not limited thereto.
[0065]
[0066] Specific examples of the group represented by formula (3) are shown below, but the group represented by formula (3) is not limited thereto.
[0067]
[0068] Specific examples of the group represented by formula (4) are shown below, but the group represented by formula (4) is not limited thereto.
[0069]
[0070] Specific examples of the group represented by formula (5) are shown below, but the group represented by formula (5) is not limited thereto.
[0071]
[0072] Specific examples of the group represented by formula (6A) and the group represented by formula (6B) are shown below, but the group represented by formula (6A) and the group represented by formula (6B) are not limited thereto.
[0073]
[0074] Specific examples of the group represented by formula (7) are shown below, but the group represented by formula (7) is not limited thereto.
[0075]
[0076] Specific examples of the group represented by formula (8) are shown below, but the group represented by formula (8) is not limited thereto.
[0077]
[0078] Specific examples of the group represented by formula (9) are shown below, but the group represented by formula (9) is not limited thereto.
[0079]
[0080] Specific examples of the group represented by formula (10) are shown below, but the group represented by formula (10) is not limited thereto.
[0081]
[0082] In formula (1-1), m1 and m2 each independently represent 0 or 1. Preferably, m1 and m2 are 0.
[0083] In formula (1-1), R 1 ~R 6 R each independently represents a hydrogen atom or a substituent. 1 ~R 6 Examples of the substituent represented by R include the groups exemplified as the substituent W. 1 ~R 6 Among these, a hydrogen atom is preferable.
[0084] In formula (1-1), Ar represents a monocyclic or fused aromatic ring which may have a substituent. The aromatic ring is preferably an aromatic hydrocarbon ring, and particularly preferably a benzene ring or a naphthalene ring.
[0085] In formula (1-1), X 1and X 2 One of them is -C(=Y X )-, and the other represents a sulfur atom, an oxygen atom, or -NR X -, -C(R X ) 2 -, or -C(=Y X ) represents -. X 3 and X 4 One of them is -C(=Y X )-, and the other represents a sulfur atom, an oxygen atom, or -NR X -, -C(R X ) 2 -, or -C(=Y X ) represents -.
[0086] The effects of the present invention are more excellent, especially in the case of X 1 ~X 4 Both are -C(=Y X )- is preferably represented.
[0087] R X represents a hydrogen atom or a substituent. X Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above.
[0088] Y X represents a sulfur atom, an oxygen atom, and ═NR W2 , or =CR W3 R W4 Represents Y. X is more effective in the present invention, and in particular, an oxygen atom or ═CR W3 R W4 It is preferable that the formula (1-1) contains a plurality of Y X If Y exists, X They may be the same or different from each other.
[0089] R W2 represents a hydrogen atom or a substituent. W2 Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above.
[0090] R W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6, or -COR W7 Represents R W5 ~R W7 R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. W3 and R W4 Each of the groups independently represents a cyano group or —COR W7 and R W3 and R W4 It is more preferable that all of R represents a cyano group. The definition of the aliphatic hydrocarbon group is as described above, and among them, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred. The definition of the aromatic ring group is as described above, and among them, an aromatic hydrocarbon group is preferred, and a phenyl group is more preferred. The definition of the aliphatic heterocyclic group is as described above, and the heteroatom contained in the aliphatic heterocyclic group is preferably an oxygen atom, a sulfur atom, or a nitrogen atom. R W5 ~R W7 Examples of the substituent that each group represented by the following formula may have include the substituents exemplified for the substituent W above.
[0091] The compound represented by formula (1-1) is preferably a compound represented by any one of formulas (1-3) to (1-6).
[0092] D in formula (1-3) to formula (1-6) 1 , D 2 , m1, m2, and R 1 ~R 6 is D in formula (1-1) 1 , D 2 , m1, m2, and R 1 ~R 6 and the preferred embodiments are also the same.
[0093] In formulas (1-3) to (1-6), Y 1 ~Y 4 each independently represents a sulfur atom, an oxygen atom, or ═NR W2 , or =CR W3 R W4 Represents Y. 1 ~Y 4is more effective in the present invention, and in particular, an oxygen atom or ═CR W3 R W4 It is preferred that
[0094] R W2 represents a hydrogen atom or a substituent. W2 Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above.
[0095] R W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. W3 and R W4 Each of the groups independently represents a cyano group or —COR W7 and R W3 and R W4 It is more preferable that all of R represents a cyano group. The definition of the aliphatic hydrocarbon group is as described above, and among them, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred. The definition of the aromatic ring group is as described above, and among them, an aromatic hydrocarbon group is preferred, and a phenyl group is more preferred. The definition of the aliphatic heterocyclic group is as described above, and the heteroatom contained in the aliphatic heterocyclic group is preferably an oxygen atom, a sulfur atom, or a nitrogen atom. R W5 ~R W7 Examples of the substituent that each group represented by the following formula may have include the substituents exemplified for the substituent W above.
[0096] R 131 , R 132 , R 141 ~R 144 , R 151 ~R 154 , R 161 , and R 162each independently represents a hydrogen atom, or a substituent selected from the group consisting of a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 7 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms (preferably 6 to 10 carbon atoms) which may have a substituent, a heteroaryl group having 3 to 20 ring members (preferably 3 to 10 ring members) which may have a substituent, an alkoxy group having 1 to 3 carbon atoms which may have a substituent, an aryloxy group having 6 to 20 carbon atoms (preferably 6 to 10 carbon atoms) which may have a substituent, a cyano group, and a halogen atom.
[0097] Specific examples of the acceptor moiety of the compound represented by formula (1-3) (the structural portion surrounded by a dotted line in formula (1-3) below) are shown below, but the acceptor moiety of the compound represented by formula (1-3) is not limited thereto.
[0098]
[0099]
[0100] Specific examples of the acceptor moiety of the compound represented by formula (1-4) (the structural portion surrounded by a dotted line in formula (1-4) below) are shown below, but the acceptor moiety of the compound represented by formula (1-4) is not limited thereto.
[0101]
[0102]
[0103] Specific examples of the acceptor moiety of the compound represented by formula (1-5) (the structural portion surrounded by a dotted line in formula (1-5) below) are shown below, but the acceptor moiety of the compound represented by formula (1-5) is not limited thereto.
[0104]
[0105]
[0106] Specific examples of the acceptor moiety of the compound represented by formula (1-6) (the structural portion surrounded by a dotted line in formula (1-6) below) are shown below, but the acceptor moiety of the compound represented by formula (1-6) is not limited thereto.
[0107]
[0108]
[0109] (Compound represented by formula (1-2)) D in formula (1-2) 1 , D 2 , m1, m2, and R 1 ~R 6 is D in formula (1-1) 1 , D 2 , m1, m2, and R 1 ~R 6 and the preferred embodiments are also the same.
[0110] In formula (1-2), Y 1 ~Y 4 each independently represents a sulfur atom, an oxygen atom, or ═NR W2 , or =CR W3 R W4 Represents Y. 1 ~Y 4 is more effective in the present invention, and in particular, an oxygen atom or ═CR W3 R W4 It is preferred that
[0111] R W2 represents a hydrogen atom or a substituent. W2 Examples of the substituent represented by the formula (I) include the groups exemplified for the substituent W above.
[0112] R W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. W3 and R W4 Each of the groups independently represents a cyano group or —COR W7 and R W3 and R W4It is more preferable that all of R represents a cyano group. The definition of the aliphatic hydrocarbon group is as described above, and among them, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred. The definition of the aromatic ring group is as described above, and among them, an aromatic hydrocarbon group is preferred, and a phenyl group is more preferred. The definition of the aliphatic heterocyclic group is as described above, and the heteroatom contained in the aliphatic heterocyclic group is preferably an oxygen atom, a sulfur atom, or a nitrogen atom. R W5 ~R W7 Examples of the substituent that each group represented by the following formula may have include the substituents exemplified for the substituent W above.
[0113] Specific examples of the acceptor moiety of the compound represented by formula (1-2) (the structural portion surrounded by a dotted line in formula (1-2) below) are shown below, but the acceptor moiety of the compound represented by formula (1-2) is not limited thereto.
[0114]
[0115]
[0116] The molecular weight of the specific compound is preferably 300 to 1200, more preferably 350 to 1000, and even more preferably 400 to 800. When the molecular weight is within the above range, the sublimation temperature of the specific compound is lowered, and it is presumed that the specific compound has excellent suitability for production.
[0117] The specific compound can be used, for example, as a p-type organic semiconductor. From the viewpoints of stability when used as a p-type organic semiconductor and matching of the energy level with an n-type organic semiconductor, the specific compound preferably has an ionization potential of −5.0 to −6.5 eV in the form of a single film.
[0118] The maximum absorption wavelength of the specific compound is preferably in the wavelength range of 400 to 600 nm, more preferably in the range of 450 to 600 nm. The maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) after adjusting the absorption spectrum of the specific compound to a concentration such that the absorbance is 0.5 to 1.0. However, if the specific compound is insoluble in chloroform, the specific compound is vapor-deposited into a film state, and the value measured using the specific compound is regarded as the maximum absorption wavelength of the specific compound.
[0119] The specific compound is particularly useful as a material for a photoelectric conversion film used in an imaging device, an optical sensor, or a photovoltaic cell. The specific compound often functions as a dye in the photoelectric conversion film. The specific compound can also be used as a coloring material, a liquid crystal material, an organic semiconductor material, a charge transport material, a pharmaceutical material, and a fluorescent diagnostic material.
[0120] The specific compound may be purified as needed. Examples of methods for purifying the specific compound include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, reslurry washing, reprecipitation purification, and purification using an adsorbent such as activated carbon and recrystallization purification. The specific compound can be synthesized by a known method.
[0121] The content of the specific compound in the photoelectric conversion film (=film thickness of the specific compound in terms of a single layer / film thickness of the photoelectric conversion film × 100) is not particularly limited, but is preferably 10 to 75% by volume, more preferably 15 to 60% by volume, and even more preferably 15 to 50% by volume. Only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is in the above range.
[0122] <n-Type Organic Semiconductor> The photoelectric conversion film preferably further contains an n-type organic semiconductor in addition to the specific compound. The n-type organic semiconductor is a compound different from the specific compound. The n-type organic semiconductor is an acceptor organic semiconductor material (compound) and refers to an organic compound that has the property of easily accepting electrons. In other words, the n-type organic semiconductor refers to the organic compound that has a larger electron affinity when two organic compounds are used in contact with each other. In other words, any organic compound can be used as the acceptor organic semiconductor as long as it is an organic compound with electron-accepting properties. Examples of n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof; fused aromatic carbon ring compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); 5- to 7-membered heterocyclic compounds having at least one selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole, and thiazole). ), polyarylene compounds, fluorene compounds, cyclopentadiene compounds, silyl compounds, 1,4,5,8-naphthalenetetracarboxylic acid anhydride, 1,4,5,8-naphthalenetetracarboxylic acid diimide derivatives, anthraquinodimethane derivatives, diphenylquinone derivatives, bathocuproine, bathophenanthroline, and derivatives thereof; triazole compounds, distyrylarylene derivatives, metal complexes having a nitrogen-containing heterocyclic compound as a ligand, silole compounds, 3,4,9,10-perylenetetracarboxylic acid dianhydride, 3,4,9,10-perylenetetracarboxylic acid diimide derivatives, and the compounds described in paragraphs
[0056] to
[0057] of JP-A No. 2006-100767.
[0123] As the n-type organic semiconductor (compound), fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred. For example, fullerene C 60 , fullerene C70 , fullerene C 76 , fullerene C 78 , fullerene C 80 , fullerene C 82 , fullerene C 84 , fullerene C 90 , fullerene C 96 , fullerene C 240 , fullerene C 540 and mixed fullerenes. Examples of fullerene derivatives include compounds in which a substituent is added to the above-mentioned fullerenes. The substituent is preferably an alkyl group, an aryl group, or a heterocyclic group. Preferred fullerene derivatives are the compounds described in JP-A-2007-123707.
[0124] The n-type organic semiconductor may be an organic dye. Examples of the organic dye include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarylium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, acridine dyes, acridinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes, and metal complex dyes.
[0125] The molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.
[0126] The maximum absorption wavelength of the n-type organic semiconductor is preferably in the range of 400 nm to 600 nm.
[0127] The photoelectric conversion film preferably has a bulk heterostructure formed by mixing a specific compound and an n-type organic semiconductor. The bulk heterostructure is a layer in the photoelectric conversion film in which the specific compound and the n-type organic semiconductor are mixed and dispersed. The photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. The bulk heterostructure is described in detail in paragraphs
[0013] to
[0014] of JP 2005-303266 A.
[0128] The difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.
[0129] When the photoelectric conversion film contains an n-type organic semiconductor, the content of the n-type organic semiconductor in the photoelectric conversion film (thickness of the n-type organic semiconductor in terms of a single layer / thickness of the photoelectric conversion film × 100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 20 to 50 vol%.
[0130] When the n-type organic semiconductor contains fullerenes, the content of the fullerenes relative to the total content of the n-type organic semiconductors (film thickness of fullerenes converted into a single layer / total film thickness of each n-type organic semiconductor converted into a single layer × 100) is preferably 50 to 100% by volume, more preferably 80 to 100% by volume. Fullerenes may be used singly or in combination of two or more types.
[0131] In terms of the response speed of the photoelectric conversion element, the content of the specific compound relative to the total content of the specific compound and the n-type organic semiconductor (film thickness in monolayer equivalent of the specific compound / (film thickness in monolayer equivalent of the specific compound + film thickness in monolayer equivalent of the n-type organic semiconductor) x 100) is preferably 20 to 80% by volume, more preferably 40 to 80% by volume. When the photoelectric conversion film contains an n-type organic semiconductor and a p-type organic semiconductor, the content of the specific compound (film thickness in monolayer equivalent of the specific compound / (film thickness in monolayer equivalent of the specific compound + film thickness in monolayer equivalent of the n-type organic semiconductor + film thickness in monolayer equivalent of the p-type organic semiconductor) x 100) is preferably 15 to 75% by volume, more preferably 30 to 75% by volume. It is preferable that the photoelectric conversion film is substantially composed of the specific compound, the n-type organic semiconductor, and a p-type organic semiconductor that is included as desired. "Substantially" means that the total content of the specific compound, n-type organic semiconductor, and p-type organic semiconductor is 90 to 100% by volume, preferably 95 to 100% by volume, and more preferably 99 to 100% by volume, relative to the total mass of the photoelectric conversion film.
[0132] <p-Type Organic Semiconductor> The photoelectric conversion film preferably further contains a p-type organic semiconductor in addition to the specific compound. The p-type organic semiconductor is a compound different from the specific compound. The p-type organic semiconductor is a donor organic semiconductor material (compound) and refers to an organic compound that has the property of easily donating electrons. In other words, the p-type organic semiconductor refers to the organic compound that has a smaller ionization potential when two organic compounds are used in contact with each other. The p-type organic semiconductor may be used alone or in combination of two or more types.
[0133] Examples of p-type organic semiconductors include triarylamine compounds (e.g., N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), compounds described in paragraphs
[0128] to
[0148] of JP-A No. 2011-228614, compounds described in paragraphs
[0052] to
[0063] of JP-A No. 2011-176259, compounds described in paragraphs
[0119] to
[0158] of JP-A No. 2011-225544, compounds, compounds described in paragraphs
[0044] to
[0051] of JP-A No. 2015-153910, and compounds described in paragraphs
[0086] to
[0090] of JP-A No. 2012-094660, etc.), pyrazoline compounds, styrylamine compounds, hydrazone compounds, polysilane compounds, thiophene compounds (for example, thienothiophene derivatives, dibenzothiophene derivatives, benzodithiophene derivatives, dithienothiophene derivatives, [1]benzothieno[3,2-b][1]benzothiophene (BTBT) derivatives, thieno[3,2-f:4,5-f']bis[1] Benzothiophene (TBBT) derivatives, compounds described in paragraphs
[0031] to
[0036] of JP 2018-014474 A, compounds described in paragraphs
[0043] to
[0045] of WO 2016 / 194630 A, compounds described in paragraphs
[0025] to
[0037] and
[0099] to
[0109] of WO 2017 / 159684 A, compounds described in paragraphs
[0029] to
[0034] of JP 2017-076766 A, compounds described in paragraphs
[0015] to
[0025] of WO 2018 / 207722 A, compounds described in paragraph [004 5] to
[0053] , compounds described in paragraphs
[0045] to
[0055] of WO2019 / 058995, compounds described in paragraphs
[0063] to
[0089] of WO2019 / 081416, compounds described in paragraphs
[0033] to
[0036] of JP2019-080052A, compounds described in paragraphs
[0044] to
[0054] of WO2019 / 054125, compounds described in paragraphs
[0041] to
[0046] of WO2019 / 093188, compounds described in paragraphs
[0034] to
[0037] of JP2019-050398A,Compounds described in paragraphs
[0033] to
[0036] of JP-A No. 2018-206878, compounds described in paragraph
[0038] of JP-A No. 2018-190755, compounds described in paragraphs
[0019] to
[0021] of JP-A No. 2018-026559, compounds described in paragraphs
[0031] to
[0056] of JP-A No. 2018-170487, compounds described in paragraphs
[0036] to
[0041] of JP-A No. 2018-166200 Compounds described in paragraphs
[0055] to
[0082] of JP-A No. 2018-113425, compounds described in paragraphs
[0041] to
[0050] of JP-A No. 2018-113425, compounds described in paragraphs
[0044] to
[0048] of JP-A No. 2018-085430, compounds described in paragraphs
[0041] to
[0045] of JP-A No. 2018-056546, compounds described in paragraphs
[0042] to
[0049] of JP-A No. 2018-046267, and paragraphs of JP-A No. 2018-014474
[0031] to
[0036] , the compounds described in paragraphs
[0036] to
[0046] of WO2018 / 016465, the compounds described in paragraphs
[0045] to
[0048] of JP2020-010024A, etc.), cyanine compounds, oxonol compounds, polyamine compounds, indole compounds, pyrrole compounds, pyrazole compounds, polyarylene compounds, fused aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyarylalkane compounds, pyrazolone compounds, amino-substituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having a nitrogen-containing heterocyclic compound as a ligand.
[0134] Examples of p-type organic semiconductors include benzoxazole compounds (for example, compounds described in Figures 3 to 7 of JP-A No. 2022-123944), dicarbazole compounds (for example, compounds described in Figures 2 to 5 of JP-A No. 2022-122839), benzoquinazoline compounds (for example, compounds described in paragraphs
[0053] to
[0056] of JP-A No. 2022-120323), azine compounds (for example, compounds described in paragraphs
[0041] to
[0042] of JP-A No. 2022-120273), compounds described in Figures 2 to 10 of JP-A No. 2022-115832, indolotriphenylene ...0323), and the like. -108268 , paragraphs
[0065] to
[0072] described compounds), indolocarbazole compounds (for example, JP-A-2023-005703, paragraphs
[0052] to
[0073] and JP-A-2022-100258, paragraph
[0028] described compounds), triscarbazolylphenyl compounds (for example, JP-A-2022-181226, paragraphs
[0038] to
[0040] described compounds), JP-A-2022-027575, paragraphs
[0070] to
[0082] described compounds, and JP-A-2021-163968, paragraphs
[0051] to
[0064] described compounds, and the like.
[0135] Furthermore, examples of p-type organic semiconductors include compounds that have a smaller ionization potential than n-type organic semiconductors, and if this condition is met, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of compounds that can be used as p-type organic semiconductors are listed below.
[0136]
[0137]
[0138]
[0139]
[0140] The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.
[0141] When the photoelectric conversion film contains a p-type organic semiconductor, the content of the p-type organic semiconductor in the photoelectric conversion film (thickness of the p-type organic semiconductor in terms of a single layer / thickness of the photoelectric conversion film × 100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 25 to 50 vol%.
[0142] The photoelectric conversion film containing the specific compound is a non-luminescent film and has characteristics different from those of an organic electroluminescent device (OLED: Organic Light Emitting Diode). A non-luminescent film means a film having a luminescence quantum efficiency of 1% or less, preferably 0.5% or less, more preferably 0.1% or less. The lower limit is often 0% or more.
[0143] <Dye> The photoelectric conversion film may further contain a dye in addition to the specific compound. The dye is a compound different from the specific compound. The dye is preferably an organic dye. Examples of the organic dye include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarylium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, acridine dyes, and benzophenone dyes. Examples of organic dyes include clidinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes, and metal complex dyes, imidazoquinoxaline dyes described in WO 2020 / 013246, WO 2022 / 168856, JP 2023-10305, and JP 2023-10299, acceptor-donor-acceptor type dyes in which two acidic nuclei are bonded to a donor, and donor-acceptor-donor type dyes in which two donors are bonded to an acceptor. Among these, organic dyes are preferably cyanine dyes, imidazoquinoxaline dyes, or acceptor-donor-acceptor type dyes, as they have a maximum absorption wavelength in the preferred range described below.
[0144] The maximum absorption wavelength of the dye is preferably in the visible light region, more preferably from 400 to 700 nm, and even more preferably from 400 to 650 nm.
[0145] The content of the dye in the photoelectric conversion film relative to the total content of the specific compound and the dye (=(film thickness of the dye in terms of a single layer / (film thickness of the specific compound in terms of a single layer+film thickness of the dye in terms of a single layer)×100) is preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and still more preferably 20 to 50 vol%.
[0146] In addition to the components described above, the photoelectric conversion film may further contain optional components. Examples of optional components include antioxidants, dispersants, and ultraviolet absorbers. The optional components may also be impurities derived from specific compounds, n-type organic semiconductors, p-type organic semiconductors, or dyes. When the photoelectric conversion film contains optional components, the content of the optional components in the photoelectric conversion film (film thickness of the optional components in terms of a single layer / film thickness of the photoelectric conversion film × 100) is preferably 0.01 to 10% by volume, and more preferably 0.01 to 1% by volume.
[0147] <Film formation method> Examples of the film formation method for the photoelectric conversion film include dry film formation methods. Examples of dry film formation methods include physical vapor deposition methods such as vapor deposition (particularly vacuum deposition), sputtering, ion plating, and MBE (Molecular Beam Epitaxy), as well as CVD (Chemical Vapor Deposition) methods such as plasma polymerization, and vacuum deposition methods are preferred. When forming the photoelectric conversion film by vacuum deposition, manufacturing conditions such as the degree of vacuum and deposition temperature can be set according to conventional methods.
[0148] The thickness of the photoelectric conversion film is preferably from 10 to 1,000 nm, more preferably from 50 to 800 nm, and even more preferably from 50 to 500 nm.
[0149] [Electrodes] The photoelectric conversion element preferably has electrodes. The electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Examples of conductive materials include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident through the upper electrode 15, it is preferable that the upper electrode 15 is transparent to the light to be detected. Examples of materials constituting the upper electrode 15 include conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO: Antimony Tin Oxide, FTO: Fluorine-doped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO: Indium Tin Oxide), and indium zinc oxide (IZO); thin metal films such as gold, silver, copper, chromium, aluminum, and nickel; mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and nanocarbon materials such as carbon nanotubes and graphene. Of these, conductive metal oxides are preferred in terms of high conductivity and transparency.
[0150] Typically, when the conductive film is made thinner than a certain range, the resistance value often increases rapidly. In a solid-state imaging device incorporating a photoelectric conversion element according to this embodiment, the sheet resistance may be 100 to 10,000 Ω / □, and there is a wide degree of freedom in the range of film thickness that can be reduced. Furthermore, the thinner the film thickness of the upper electrode (transparent conductive film) 15, the less light it absorbs, and generally the higher the light transmittance. An increase in light transmittance is desirable because it increases light absorption in the photoelectric conversion film and enhances photoelectric conversion performance. Considering the suppression of leakage current, the increase in the resistance value of the thin film, and the increase in transmittance that accompany a reduction in film thickness, the thickness of the upper electrode 15 is preferably 5 to 100 nm, and more preferably 5 to 20 nm.
[0151] Depending on the application, the lower electrode 11 may be made transparent or may be made non-transparent and reflect light. Examples of materials constituting the lower electrode 11 include conductive metal oxides such as antimony- or fluorine-doped tin oxide (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metals such as gold, silver, copper, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and carbon materials such as carbon nanotubes and granphenes.
[0152] The method for forming the electrodes can be appropriately selected depending on the electrode material. Specific examples include wet methods such as printing and coating; physical methods such as vacuum deposition, sputtering, and ion plating; and chemical methods such as CVD and plasma CVD. When the electrode material is ITO, examples include electron beam methods, sputtering, resistance heating deposition, chemical reaction methods (such as the sol-gel method), and coating of a dispersion of indium tin oxide.
[0153] [Charge-blocking film: electron-blocking film, hole-blocking film] The photoelectric conversion element preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film. Examples of the intermediate layer include a charge-blocking film. When the photoelectric conversion element has this film, the properties (quantum efficiency, response speed, etc.) of the resulting photoelectric conversion element are more excellent. Examples of the charge-blocking film include an electron-blocking film and a hole-blocking film.
[0154] [Electron Blocking Film] The electron blocking film is a donor organic semiconductor material (compound), and the above-mentioned p-type organic semiconductor can be used. Polymer materials can also be used as the electron blocking film. Examples of polymer materials include polymers of phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, as well as derivatives thereof.
[0155] The electron blocking film may be composed of multiple films. The electron blocking film may be composed of an inorganic material. In general, inorganic materials have a higher dielectric constant than organic materials, so when an inorganic material is used for the electron blocking film, a higher voltage is applied to the photoelectric conversion film, resulting in higher quantum efficiency. Examples of inorganic materials that can be used for the electron blocking film include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, indium copper oxide, indium silver oxide, and iridium oxide.
[0156] [Hole-Blocking Film] The hole-blocking film is an acceptor organic semiconductor material (compound), and the n-type organic semiconductors described above can be used. The hole-blocking film may be composed of multiple films.
[0157] Examples of methods for producing a charge blocking film include dry film formation and wet film formation. Examples of dry film formation methods include vapor deposition and sputtering. Vapor deposition may be either physical vapor deposition (PVD) or chemical vapor deposition (CVD), with physical vapor deposition such as vacuum deposition being preferred. Examples of wet film formation methods include inkjet printing, spray printing, nozzle printing, spin coating, dip coating, casting, die coating, roll coating, bar coating, and gravure coating, with the inkjet method being preferred in terms of high-precision patterning.
[0158] The thickness of each of the charge blocking films (electron blocking film and hole blocking film) is preferably from 3 to 200 nm, more preferably from 5 to 100 nm, and even more preferably from 5 to 30 nm.
[0159] [Substrate] The photoelectric conversion element may further include a substrate. Examples of the substrate include a semiconductor substrate, a glass substrate, and a plastic substrate. The substrate is usually positioned such that a conductive film, a photoelectric conversion film, and a transparent conductive film are stacked in this order on the substrate.
[0160] [Sealing Layer] The photoelectric conversion element may further have a sealing layer. The performance of photoelectric conversion materials may be significantly degraded in the presence of degrading factors such as water molecules. Therefore, the degradation can be prevented by covering and sealing the entire photoelectric conversion film with a sealing layer made of ceramics such as dense metal oxides, metal nitrides, or metal nitride oxides, or diamond-like carbon (DLC), which do not allow water molecules to penetrate. Examples of sealing layers include those described in paragraphs
[0210] to
[0215] of JP 2011-082508 A, the contents of which are incorporated herein by reference.
[0161] [Method for manufacturing photoelectric conversion element] Examples of methods for manufacturing photoelectric conversion elements include known manufacturing methods. Specifically, for example, methods for manufacturing photoelectric conversion elements include a step of forming a conductive film on a substrate, a step of forming a photoelectric conversion film, and a step of forming a transparent conductive film. The method for manufacturing a photoelectric conversion element may include other steps (for example, a step of forming a charge blocking film and a step of forming a sealing layer) in addition to the above. The method for forming each layer is as described above.
[0162] [Imaging element] An example of an application of a photoelectric conversion element is an imaging element. An imaging element is an element that converts the optical information of an image into an electrical signal, and typically has multiple photoelectric conversion elements arranged in a matrix on the same plane, with each photoelectric conversion element (pixel) converting the optical signal into an electrical signal and outputting the electrical signal pixel by pixel from the imaging element. For this reason, each pixel is composed of one or more photoelectric conversion elements and one or more transistors. The manufacturing method of an imaging element is not particularly limited, but examples include a method including the step of manufacturing the photoelectric conversion element described above.
[0163] [Optical Sensor] Other applications of the photoelectric conversion element include, for example, a photocell and an optical sensor, and the photoelectric conversion element of the present invention is preferably used as an optical sensor. As an optical sensor, the photoelectric conversion element may be used alone, or may be used as a line sensor in which the photoelectric conversion elements are arranged linearly or as a two-dimensional sensor in which the photoelectric conversion elements are arranged on a plane.
[0164] [Compound] <Compound represented by formula (1-1)> The compound represented by formula (1-1) of the present invention corresponds to one form of the compound represented by formula (1-1) shown as a specific compound in the upper part. Preferred embodiments of the compound represented by formula (1-1) of the present invention are also the same as the preferred embodiments of the compound represented by formula (1-1) shown as the above-mentioned specific compound.
[0165] The compound represented by formula (1-1) of the present invention is the following compound.
[0166]
[0167] In formula (1-1), D 1 and D 2 Each independently represents a group selected from the group consisting of groups represented by the above formulas (3) to (10), and the preferred embodiments thereof are also the same. 1 ~R 6 , and X 1 ~X 4 represents m1, m2, Ar, and R in the compound represented by formula (1-1) shown as a specific compound in the upper part. 1 ~R 6 , and X1 ~X 4 and the preferred embodiments are also the same.
[0168] <Compound Represented by Formula (1-2)> The compound represented by formula (1-2) of the present invention is the compound represented by formula (1-2) shown as the specific compound above. Preferred embodiments of the compound represented by formula (1-2) of the present invention are also the same as the preferred embodiments of the compound represented by formula (1-2) shown as the specific compound above.
[0169] The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the examples shown below. In the following, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, and "Ac" represents an acetyl group.
[0170] 1. Synthesis Example [Synthesis of Compound (B-1)] Compound (B-1) was synthesized according to the following scheme. In the following scheme, the abbreviations are as follows: LDA: lithium diisopropylamide DMF: dimethylformamide THF: tetrahydrofuran RuPhos: 2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl NBS: N-bromosuccinimide
[0171]
[0172] <Synthesis of Compound (B-1a)> Compound (B-1a) was synthesized with reference to the method described in a non-patent document (J. Phys. Chem. C, 119 (2015), p. 21053).
[0173] <Synthesis of Compound (B-1b)> Compound (B-1b) was synthesized by the Vilsmeier reaction of 2,3-dimethylthiophene (manufactured by Tokyo Chemical Industry Co., Ltd.) with reference to the method described in Non-Patent Document (Organic Reactions, 49 (1997), p. 1).
[0174] <Synthesis of Compound (B-1)> 214 mg of Compound B-1a, 280 mg of Compound B-1b, and 20 mL of 1-butanol were added to a 100 mL three-neck flask under a nitrogen atmosphere, and the mixture was stirred at 110°C for 1 hour. After the reaction was completed, the precipitated solid was collected by filtration, and the obtained crude product was dispersed and washed with chloroform and methanol for purification. 1 The H-NMR (Nuclear Magnetic Resonance) data is shown below. 1 H-NMR (CDCl 3 ): δ = 8.35 (2H, d), 8.00 (2H, s), 7.86 (2H, s), 2.55 (6H, s), 2.25 (6H, s)
[0175] The ultraviolet-visible absorption spectrum of the synthesized compound B-1 (solvent: chloroform / 1,1,1,3,3,3-hexafluoro-2-propyl alcohol = 4 / 1 (volume ratio)) is shown in Figure 3. The maximum absorption wavelength λmax of compound B-1 is 503 nm, and the molar absorption coefficient ε at this λmax is 119,000 Lmol -1 cm -1 It was.
[0176] [Synthesis of Compound (B-2), Compound (B-3), and Compound (B-6)] Compounds (B-2), (B-3), and (B-6) were synthesized by the following method.
[0177] <Synthesis of Compound (B-2b), Compound (B-3b), and Compound (B-6b)> Compounds (B-2b), (B-3b), and (B-6b) shown below were synthesized by the following methods.
[0178]
[0179] Compounds (B-2b), (B-3b), and (B-6b) were each synthesized in the same manner as in the above <Synthesis of compound (B-1b)>, except that 2-ethylthiophene (manufactured by Tokyo Chemical Industry Co., Ltd.), 2-isopropylthiophene (synthesized with reference to paragraphs
[0046] to
[0048] of JP2014-015552A), or 2-ethylfuran (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 2,3-dimethylthiophene.
[0180] <Synthesis of Compound (B-2), Compound (B-3), and Compound (B-6)> Compounds (B-2), (B-3), and (B-6) were synthesized in the same manner as in <Synthesis of Compound (B-1)> above, except that compound (B-1b) was replaced with compound (B-2b), compound (B-3b), or compound (B-6b).
[0181] [Synthesis of Compound (B-4)] Compound (B-4) was synthesized by the following method. <Synthesis of Compound (B-4b)>
[0182]
[0183] 2-formyl-6-bromobenzo[b]thiophene was synthesized from 6-bromobenzo[b]thiophene (manufactured by Tokyo Chemical Industry Co., Ltd.) with reference to the specification of Chinese Patent Application Publication No. 104774318 (CN104774318), and compound (B-4b) was synthesized using this with reference to Example 75.1 of WO 2013 / 192352.
[0184] <Synthesis of Compound (B-4)> Compound (B-4) was synthesized in the same manner as in <Synthesis of Compound (B-1)> above, except that compound (B-4b) was used instead of compound (B-1b).
[0185] [Synthesis of Compound (B-5)] Compound (B-5) was synthesized by the following method. <Synthesis of Compound (B-5b)>
[0186]
[0187] With reference to the non-patent document RSC Advances, 3 (2013), 22544, 2-bromo-5-formylthieno[3,2-b]thiophene was synthesized from thieno[3,2-b]thiophene (manufactured by Tokyo Chemical Industry Co., Ltd.), and compound (B-5b) was synthesized using this with reference to Example 75.1 of WO 2013 / 192352.
[0188] <Synthesis of Compound (B-5)> Next, compound (B-5) was synthesized in the same manner as in the above <Synthesis of Compound (B-1)>, except that compound (B-5b) was used instead of compound (B-1b).
[0189] [Synthesis of Compound (B-7)] Compound (B-7) was synthesized by the following method. <Synthesis of Compound (B-7a)>
[0190]
[0191] Compound (B-7a) was synthesized from diethyl malonate, hydrazine, and malonyl chloride with reference to the non-patent literature New J. Chem., 43 (2019), 6350 and WO 2007 / 019931.
[0192] <Synthesis of Compound (B-7)> Next, compound (B-7) was synthesized in the same manner as in the above <Synthesis of Compound (B-1)>, except that compound (B-7a) was used instead of compound (B-1a).
[0193] 2. Evaluation Examples [Various Materials] The materials used in the photoelectric conversion element are shown below. Compounds B-1 to B-7 correspond to specific compounds used in the examples, and compounds C1 and C2 correspond to comparative compounds used in the comparative examples.
[0194] <Specific compounds and comparative compounds>
[0195]
[0196] <n-type organic semiconductor> C60: fullerene (C 60 )
[0197] <p-type organic semiconductor>
[0198] [Evaluation] Photoelectric conversion elements were prepared using the above materials, and the following evaluations were carried out. <Preparation of Photoelectric Conversion Element> A photoelectric conversion element having the configuration shown in FIG. 2 was prepared using the various components shown above. Here, the photoelectric conversion element comprises a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15. Specifically, amorphous ITO was formed on a glass substrate by sputtering to form a lower electrode 11 (thickness: 30 nm), and compound (EB-1) was further formed on the lower electrode 11 by vacuum heating deposition to form an electron blocking film 16A (thickness: 30 nm). Subsequently, with the glass substrate at room temperature, each specific compound or each comparative compound shown in Table 1 and an n-type organic semiconductor (fullerene (C 60 )) and a p-type organic semiconductor were co-deposited by vacuum deposition to form a film having a thickness of 80 nm in terms of a single layer. This resulted in a photoelectric conversion film 12 having a bulk heterostructure of 240 nm. At this time, the film formation rate of the photoelectric conversion film 12 was 1.0 Å / sec. Furthermore, a compound (EB-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm). Amorphous ITO was deposited on the hole blocking film 16B by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm). After a SiO film was formed as a sealing layer on the upper electrode 15 by vacuum deposition, aluminum oxide (Al 2 O 3 The resulting laminate was heated in a glove box at 150° C. for 30 minutes to obtain a photoelectric conversion element.
[0199]
[0200] <Dependence of Response Speed on Electric Field Strength> The dependence of response speed on electric field strength of each of the obtained photoelectric conversion elements was evaluated by the following method. 5A voltage was applied to each photoelectric conversion element so that the intensity was 7.5 × 10 V / cm. Then, an LED (light emitting diode) was momentarily turned on to irradiate light from the upper electrode (transparent conductive film) side, and the photocurrent at a wavelength of 460 nm at that time was measured with an oscilloscope to measure the rise time from 0% signal intensity to 97% signal intensity. Next, the voltage applied to each photoelectric conversion element was changed to 7.5 × 10 4 The same procedure was followed except that the pressure was changed to 7.5 × 10 4 The response speed at 100 V / cm was measured. Then, the electric field strength dependency of the response speed was calculated and evaluated according to the formula (S3). Formula (S3): Electric field strength dependency of response speed = (7.5 × 10 at a wavelength of 460 nm for each example or each comparative example) 4 V / cm) / (2.0×10 at a wavelength of 460 nm for each Example or Comparative Example 5 V / cm) In the formula (S3), the photoelectric conversion elements in the numerator and denominator are the same. For example, with regard to Example 1-1, the photoelectric conversion efficiency of Example 1-1 at a wavelength of 460 nm is 7.5 × 10 4 V / cm and the photoelectric conversion efficiency of Example 1-1 at a wavelength of 460 nm of 2.0 × 10 5 The rise time at V / cm is compared.
[0201] (Evaluation Criteria) A: The electric field strength dependency of the response speed is less than 2.0 B: The electric field strength dependency of the response speed is 2.0 or more and less than 3.0 C: The electric field strength dependency of the response speed is 3.0 or more and less than 4.0 D: The electric field strength dependency of the response speed is 4.0 or more
[0202] <Evaluation of Manufacturability (Vapor Deposition Heat Resistance)> The quantum efficiency of each of the obtained photoelectric conversion elements was measured by the following method. Note that, hereinafter, the photoelectric conversion element produced by the above-described procedure (i.e., the photoelectric conversion element produced under the condition of a film formation rate of 1.0 Å / sec) is also referred to as photoelectric conversion element (A).
[0203] Photoelectric conversion element (A) 2.0 × 10 5After applying a voltage to achieve an electric field strength of 1000 V / cm, light was irradiated from the upper electrode (transparent conductive film) side to evaluate the quantum efficiency (photoelectric conversion efficiency) at a wavelength of 460 nm. This is referred to as the "quantum efficiency of the photoelectric conversion element (A)." Next, a photoelectric conversion element (B) of each example or comparative example was prepared using the same procedure as for the photoelectric conversion element (A), except that the deposition rate of the photoelectric conversion film 12 was set to 3.0 Å / sec. The quantum efficiency of the obtained photoelectric conversion element (B) was measured using the same method as for the photoelectric conversion element (A). Furthermore, the quantum efficiencies of the photoelectric conversion element (A) and the photoelectric conversion element (B) having the same example or comparative example configuration were compared, and the relative ratio B / A of "quantum efficiency of the photoelectric conversion element (B) / quantum efficiency of the photoelectric conversion element (A)" was calculated, and the obtained value was used to evaluate the manufacturability of each photoelectric conversion element in light of the following criteria. Compounds with excellent evaluation results are materials whose performance is unlikely to deteriorate during high-speed film formation, and are therefore excellent in manufacturability.
[0204] (Evaluation Criteria) A: The relative ratio B / A is 0.90 or more. B: The relative ratio B / A is 0.85 or more and less than 0.90. C: The relative ratio B / A is 0.80 or more and less than 0.85. D: The relative ratio B / A is less than 0.80.
[0205] The evaluation results are shown in Table 1. In Table 1, in the column "Type of Formula (1-1) and Formula (1-2)", "Formula (1-1)" indicates that the specific compound corresponds to the compound represented by the above formula (1-1), and "Formula (1-2)" indicates that the specific compound corresponds to the compound represented by formula (1-2). 1 and D 2 The "Type" column indicates the type of a specific compound when it is applied to formula (1-1) or formula (1-2). 1 and D 2 In Table 1, in the column "Type of m1 and m2," "A" indicates that when a specific compound is applied to formula (1-1) or formula (1-2), both m1 and m2 are 0, and "B" indicates that this does not apply. X or Y 1 ~Y 4In the "Type" column, "A" represents the type of X when the specific compound is applied to formula (1-1). 1 ~X 4 All of the sites corresponding to -C(=Y X )-, and Y X is an oxygen atom or =CR W3 R W4 or when the specific compound is applied to formula (1-2), Y 1 ~Y 4 All of the sites corresponding to W3 R W4 In Table 1, the column "Type of Formula (1-2) to Formula (1-6)" indicates which of the compounds represented by the above-mentioned formulas (1-2) to (1-6) the specific compound falls under when the specific compound falls under the category of the compound represented by formula (1-1).
[0206]
[0207] From the results in Table 1, it is clear that the photoelectric conversion element of the example has a small dependency of the response speed to blue-green light on the electric field strength. 1 and D 2 In the case where the aromatic ring group at the site corresponding to has a sulfur atom as a ring member atom at the position adjacent to the carbon atom having a bond to the mother nucleus (for example, D 1 and D 2 When the site corresponding to the formula (3) is a group represented by the formula (3), "X 31 " is a sulfur atom, D 1 and D 2 When the site corresponding to the formula (5) is a group represented by the formula (5), "X 51 " is a sulfur atom, and D 1 and D 2 When the site corresponding to the formula (6A) is a group represented by the formula (6A), "X 61 " is a sulfur atom), it is clear that the electric field strength dependency of the response speed to blue-green light is small (see the results of Example 1-6). Furthermore, it is clear that when the number of carbon atoms in the specific alkyl group of the specific compound is 3 or more, the manufacturing suitability is better (see the results of Example 1-3).
[0208] 10a, 10b Photoelectric conversion element 11 Conductive film (lower electrode) 12 Photoelectric conversion film 15 Transparent conductive film (upper electrode) 16A Electron blocking film 16B Hole blocking film
Claims
1. A photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, wherein the photoelectric conversion film contains a compound represented by formula (1-1) or formula (1-2). In formula (1-1), D 1 and D 2 Each independently represents a monocyclic or condensed aromatic ring group which may have a substituent. However, the aromatic ring group has at least one alkyl group bonded to a carbon atom which is a ring atom of the aromatic ring group as a substituent, and when the aromatic ring group has one alkyl group as the substituent, the alkyl group has 2 or more carbon atoms, and when the aromatic ring group has two or more alkyl groups as the substituent, the total carbon number of the two or more alkyl groups is 2 or more. In addition, in the aromatic ring group, when adjacent carbon atoms which are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. m1 and m2 each independently represent 0 or 1. R 1 ~R 6 Each of X independently represents a hydrogen atom or a substituent. Ar represents a monocyclic or condensed aromatic ring which may have a substituent. 1 and X 2 One of them is -C(=Y X )-, and the other represents a sulfur atom, an oxygen atom, or -NR X -, -C(R X ) 2 -, or -C(=Y X ) represents -. X 3 and X 4 One of them is -C(=Y X )-, and the other represents a sulfur atom, an oxygen atom, or -NR X -, -C(R X ) 2 -, or -C(=Y X )-. X represents a hydrogen atom or a substituent. X represents a sulfur atom, an oxygen atom, and ═NR W2 , or =CR W3 R W4 Represents R W2 represents a hydrogen atom or a substituent. W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. 1 and D 2 Each independently represents a monocyclic or condensed aromatic ring group which may have a substituent. However, the aromatic ring group has at least one alkyl group bonded to a carbon atom which is a ring atom of the aromatic ring group as a substituent, and when the aromatic ring group has one alkyl group as the substituent, the alkyl group has 2 or more carbon atoms, and when the aromatic ring group has two or more alkyl groups as the substituent, the total carbon number of the two or more alkyl groups is 2 or more. In addition, in the aromatic ring group, when adjacent carbon atoms which are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. m1 and m2 each independently represent 0 or 1. R 1 ~R 6 Each independently represents a hydrogen atom or a substituent. 1 ~Y 4 each independently represents a sulfur atom, an oxygen atom, or ═NR W2 , or =CR W3 R W4 Represents R W2 represents a hydrogen atom or a substituent. W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent.
2. The above D 1 and the above D 2 The photoelectric conversion element according to claim 1, wherein each independently represents a group selected from the group consisting of groups represented by formulas (2) to (10): In formula (2), T 21 ~T 25 are each independently -CR 21 = or -N=. 21 represents a hydrogen atom or a substituent. 21 If there are multiple R 21 may be the same or different. * indicates a bonding position. 21 ~T 25 At least one of 21 is an alkyl group 21 =, T 21 ~T 25 Only one of them is R 21 is an alkyl group 21 When R represents 21 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 21 ~T 25 Two or more of the following are R 21 is an alkyl group 21 When R = 21 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 21 ~T 25 Medium, T 21 ~T 25 Two adjacent ones of 21 is an alkyl group 21 In the formula (3), when X represents a group represented by the formula (3), the alkyl groups may be bonded to each other to form a ring structure. 31 represents a sulfur atom, an oxygen atom, or —NR X1 - represents. 31 ~T 33 are each independently -CR 31 = or -N=. X1 and R 31 Each independently represents a hydrogen atom or a substituent. 31 If there are multiple R 31 may be the same or different. * indicates a bonding position. 31 ~T 33 At least one of 31 is an alkyl group 31 =, T 31 ~T 33 Only one of them is R 31 is an alkyl group 31 When R represents 31 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 31 ~T 33 Two or more of the following are R 31 is an alkyl group 31 When R = 31 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 31 ~T 33 Medium, T 31 ~T 33 Two adjacent ones of 31 is an alkyl group 31 In the formula (4), when T represents a substituted or unsubstituted alkyl group, the alkyl groups may be bonded to each other to form a ring structure. 41 ~T 47 are each independently -CR 41 = or -N=. 41 represents a hydrogen atom or a substituent. 41 If there are multiple R 41 may be the same or different. * indicates a bonding position. 41 ~T 47 At least one of 41 is an alkyl group 41 =, T 41 ~T 47 Only one of them is R 41 is an alkyl group 41 When R represents 41 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 41 ~T 47 Two or more of the following are R 41 is an alkyl group 41 When R = 41 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 41 ~T 47 Medium, T 41 ~T 47 Two adjacent ones of 41 is an alkyl group 41 In the formula (5), when X represents a group represented by the formula (5), the alkyl groups may be bonded to each other to form a ring structure. 51 represents a sulfur atom, an oxygen atom, or —NR X1 - represents. 51 ~T 55 are each independently -CR 51 = or -N=. X1 and R 51 Each independently represents a hydrogen atom or a substituent. 51 If there are multiple R 51 may be the same or different. * indicates a bonding position. 51 ~T 55 At least one of 51 is an alkyl group 51 =, T 51 ~T 55 Only one of them is R 51 is an alkyl group 51 When R represents 51 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 51 ~T 55 Two or more of the following are R 51 is an alkyl group 51 When R = 51 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 51 ~T 55 Medium, T 51 ~T 55 Two adjacent ones of 51 is an alkyl group 51 In the formula (6A), when X represents a group represented by the formula (6A), the alkyl groups may be bonded to each other to form a ring structure. 61 represents a sulfur atom, an oxygen atom, or —NR X1 - represents Y 6a and Y 6b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or -N=. X1 , R Y1 , R 61 , and R 62 Each of the symbols independently represents a hydrogen atom or a substituent. * represents a bonding position. However, the group represented by formula (6A) satisfies any one of the following requirements 6AA to 6AD. Requirement 6AA: Y 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 and R 62 represents a group other than an alkyl group. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and R 61 and R 62 At least one of the R represents an alkyl group. 61 and R 62 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and 61 and R 62 When both of Y and Y represent alkyl groups, the total number of carbon atoms in the alkyl groups is 2 or more. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 and R 62 At least one of the R represents an alkyl group. Y1 and the at least one R 61 and R 62 The total number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b one of which represents -N=, and R 61 and R 62 At least one of the R represents an alkyl group. 61 and R 62 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and 61 and R 62 In the formula (6B), when both of X represent an alkyl group, the total number of carbon atoms of the alkyl groups is 2 or more. 61 represents a sulfur atom, an oxygen atom, or —NR X1 - represents Y 6a and Y 6b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or -N=. X1 , R Y1 , and R 61 Each of the symbols independently represents a hydrogen atom or a substituent. * represents a bonding position. However, the group represented by formula (6B) satisfies any one of the following requirements 6BA to 6BD. Requirement 6BA: Y 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 represents a group other than an alkyl group. Y1 The alkyl group represented by the formula (I) has 2 or more carbon atoms. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and R 61 represents an alkyl group. 61 The alkyl group represented by the formula (I) has 2 or more carbon atoms. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 represents an alkyl group. Y1 and the alkyl group represented by R 61 The total number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b one of which represents -N=, and R 61 represents an alkyl group. 61 In formula (7), the alkyl group represented by X has 2 or more carbon atoms. 71 represents a sulfur atom, an oxygen atom, -NR X1 -, -C(R X2 ) 2 -, or -Si(R X3 ) 2 - represents Y 7a and Y 7b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or =N-. 7 represents a monocyclic or condensed aromatic ring which may have a substituent. X1 , R X2 , R X3 , and R Y1 Each of Y independently represents a hydrogen atom or a substituent. However, the group represented by formula (7) satisfies any one of the following requirements 7A to 7J. Requirement 7A: Y 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of Y and Y represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 7 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 7 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 7 In the formula (7), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 and the alkyl group represented by R X2 The total number of carbon atoms in the alkyl groups represented by the formula (I) is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. X2 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 the alkyl group represented by R X2 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of the two represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the above groups represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 7a and Y 7b One of the two represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 7 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 7 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of the two represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. X2 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (8), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 81 represents a sulfur atom, an oxygen atom, -NR X1 -, -C(R X2 ) 2 -, or -Si(R X3 ) 2 - represents Ar 8 represents a monocyclic or condensed aromatic ring which may have a substituent. 81 ~T 83 are each independently -CR 81 = or -N=. X1 , R X2 , R X3 , and R 81 Each independently represents a hydrogen atom or a substituent. 81 If there are multiple R 81 may be the same or different. * indicates a bonding position. However, the group represented by formula (8) satisfies any one of the following requirements 8A to 8G. Requirement 8A: T 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 81 ~T 83 Only one of the 81 is an alkyl group 81 When R represents 81 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 81 ~T 83 Two or more of the 81 is an alkyl group 81 When R = 81 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When T represents ≡ ... 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atoms that are ring members of R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the above groups represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 8 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 8 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atoms that are ring members of R do not have alkyl groups as substituents. 81 and the alkyl group represented by R X2 The total number of carbon atoms in the alkyl group represented by T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When T represents ≡ ... 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 81 and the alkyl group represented by Ar 8 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When Ar represents ═ ... 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atom that is a ring atom of R has an alkyl group as a substituent. X2 and the alkyl group represented by Ar 8 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 81 the alkyl group represented by R X2 and the alkyl group represented by Ar 8 The carbon atom which is a ring atom of T has as a substituent an alkyl group having two or more carbon atoms. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When Ar represents ═ ... 8 In the formula (9), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 91 represents a sulfur atom, an oxygen atom, or —NR X1 - represents Ar 9 represents a monocyclic or condensed aromatic ring which may have a substituent. 91 ~T 93 are each independently -CR 91 = or -N=. X1 and R 91 represents a hydrogen atom or a substituent. 91 If there are multiple R 91 may be the same or different. * indicates a bonding position. However, the group represented by formula (9) satisfies any one of the following requirements 9A to 9C. Requirement 9A: T 91 ~T 93 At least one of 91 is an alkyl group 91 = and Ar 9 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 91 ~T 93 Only one of the 91 is an alkyl group 91 When R represents 91 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 91 ~T 93 Two or more of the 91 is an alkyl group 91 When R = 91 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 91 ~T 93 Medium, T 91 ~T 93 Two adjacent ones of 91 is an alkyl group 91 When T represents a substituted or unsubstituted alkyl group, the alkyl groups may be bonded to each other to form a ring structure. 91 ~T 93 But, R 91 is an alkyl group 91 represents a group other than . 9 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 9 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 9 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 9 In the formula (9), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 91 ~T 93 At least one of 91 is an alkyl group 91 = and Ar 9 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 91 and the alkyl group represented by Ar 9 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 91 ~T 93 Medium, T 91 ~T 93 Two adjacent ones of 91 is an alkyl group 91 When Ar represents ═ ... 9 In formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or =N-. 10 represents a monocyclic or condensed aromatic ring which may have a substituent. 10 and T 11 are each independently -CR 101 = or -N=. X1 , R 101 , and R Y1 Each independently represents a hydrogen atom or a substituent. 101 If there are multiple R 101 and may be the same or different. * indicates a bonding position. However, the group represented by formula (10) satisfies any one of the following requirements 10A to 10J. Requirement 10A: Y 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 10 and T 11 Only one of the 101 is an alkyl group 101 When R represents 101 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 10 and T 11 Both of them are R 101 is an alkyl group 101 When the two R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 10 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 10 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 and the alkyl group represented by R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 and the alkyl group represented by Ar 10 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 101 and the alkyl group represented by Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 the alkyl group represented by R 101 and the alkyl group represented by Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 In the formula (10), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 10 and T 11 Only one of the 101 is an alkyl group 101 When R represents 101 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 10 and T 11 Both of them are R 101 is an alkyl group 101 When the two R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 10 When Ar has only one alkyl group as a substituent, the alkyl group has two or more carbon atoms, and 10 When Ar has two or more alkyl groups as substituents, the total number of carbon atoms of the two or more alkyl groups is two or more. 10 In the formula (10), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 101 and the alkyl group represented by Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
3. The above D 1 and the above D 2 The photoelectric conversion element according to claim 2, wherein each independently represents a group selected from the group consisting of groups represented by formulas (3) to (10):
4. The photoelectric conversion element according to any one of claims 1 to 3, wherein m1 and m2 both represent 0.
5. In the formula (1-1), the X 1 ~The above X 4 However, both are -C (=Y X )-, and the Y X each independently represents an oxygen atom or ═CR W3 R W4 In the formula (1-2), the Y 1 ~ The above Y 4 each independently represents an oxygen atom or ═CR W3 R W4 The photoelectric conversion element according to any one of claims 1 to 3, wherein 6. The photoelectric conversion element according to claim 1, wherein the compound represented by formula (1-1) is a compound represented by any one of formulas (1-3) to (1-6). In formulas (1-3) to (1-6), D 1 and D 2 Each independently represents a monocyclic or condensed aromatic ring group which may have a substituent. However, the aromatic ring group has at least one alkyl group bonded to a carbon atom which is a ring atom of the aromatic ring group as a substituent, and when the aromatic ring group has one alkyl group as the substituent, the alkyl group has 2 or more carbon atoms, and when the aromatic ring group has two or more alkyl groups as the substituent, the total carbon number of the two or more alkyl groups is 2 or more. In addition, in the aromatic ring group, when adjacent carbon atoms which are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. m1 and m2 each independently represent 0 or 1. R 1 ~R 6 Each independently represents a hydrogen atom or a substituent. 1 ~Y 4 each independently represents a sulfur atom, an oxygen atom, or ═NR W2 , or =CR W3 R W4 Represents R W2 represents a hydrogen atom or a substituent. W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. 131 , R 132 , R 141 ~R 144 , R 151 ~R 154 , R 161 , and R 162 each independently represents a hydrogen atom or a substituent selected from the group consisting of a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 7 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 ring members which may have a substituent, an alkoxy group having 1 to 3 carbon atoms which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, a cyano group, and a halogen atom.
7. The photoelectric conversion element according to any one of claims 1 to 3, wherein the photoelectric conversion film further contains an n-type organic semiconductor, and the photoelectric conversion film has a bulk heterostructure formed in a state where the compound and the n-type organic semiconductor are mixed together.
8. The photoelectric conversion element according to claim 7, wherein the n-type organic semiconductor contains a fullerene selected from the group consisting of fullerenes and derivatives thereof.
9. The photoelectric conversion element according to any one of claims 1 to 3, wherein the photoelectric conversion film further contains a p-type organic semiconductor.
10. The photoelectric conversion element according to any one of claims 1 to 3, wherein the photoelectric conversion film further contains a dye.
11. The photoelectric conversion element according to any one of claims 1 to 3, further comprising one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
12. An imaging device comprising the photoelectric conversion element according to any one of claims 1 to 3.
13. An optical sensor comprising the photoelectric conversion element according to any one of claims 1 to 3.
14. A method for manufacturing an imaging element, comprising the step of manufacturing the photoelectric conversion element according to any one of claims 1 to 3.
15. A compound represented by formula (1-1). In formula (1-1), D 1 and D 2 each independently represents a group selected from the group consisting of groups represented by formulas (3) to (10). m1 and m2 each independently represent 0 or 1. R 1 ~R 6 Each of X independently represents a hydrogen atom or a substituent. Ar represents a monocyclic or condensed aromatic ring which may have a substituent. 1 and X 2 One of them is -C(=Y X )-, and the other represents a sulfur atom, an oxygen atom, or -NR X -, -C(R X ) 2 -, or -C(=Y X ) represents -. X 3 and X 4 One of them is -C(=Y X )-, and the other represents a sulfur atom, an oxygen atom, or -NR X -, -C(R X ) 2 -, or -C(=Y X )-. X represents a hydrogen atom or a substituent. X represents a sulfur atom, an oxygen atom, and ═NR W2 , or =CR W3 R W4 Represents R W2 represents a hydrogen atom or a substituent. W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. In formula (3), X 31 represents a sulfur atom, an oxygen atom, or —NR X1 - represents. 31 ~T 33 are each independently -CR 31 = or -N=. X1 and R 31 Each independently represents a hydrogen atom or a substituent. 31 If there are multiple R 31 may be the same or different. * indicates a bonding position. 31 ~T 33 At least one of 31 is an alkyl group 31 =, T 31 ~T 33 Only one of them is R 31 is an alkyl group 31 When R represents 31 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 31 ~T 33 Two or more of the following are R 31 is an alkyl group 31 When R = 31 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 31 ~T 33 Medium, T 31 ~T 33 Two adjacent ones of 31 is an alkyl group 31 In the formula (4), when T represents a substituted or unsubstituted alkyl group, the alkyl groups may be bonded to each other to form a ring structure. 41 ~T 47 are each independently -CR 41 = or -N=. 41 represents a hydrogen atom or a substituent. 41 If there are multiple R 41 may be the same or different. * indicates a bonding position. 41 ~T 47 At least one of 41 is an alkyl group 41 =, T 41 ~T 47 Only one of them is R 41 is an alkyl group 41 When R represents 41 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 41 ~T 47 Two or more of the following are R 41 is an alkyl group 41 When R = 41 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 41 ~T 47 Medium, T 41 ~T 47 Two adjacent ones of 41 is an alkyl group 41 In the formula (5), when X represents a group represented by the formula (5), the alkyl groups may be bonded to each other to form a ring structure. 51 represents a sulfur atom, an oxygen atom, or —NR X1 - represents. 51 ~T 55 are each independently -CR 51 = or -N=. X1 and R 51 Each independently represents a hydrogen atom or a substituent. 51 If there are multiple R 51 may be the same or different. * indicates a bonding position. 51 ~T 55 At least one of 51 is an alkyl group 51 =, T 51 ~T 55 Only one of them is R 51 is an alkyl group 51 When R represents 51 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 51 ~T 55 Two or more of the following are R 51 is an alkyl group 51 When R = 51 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 51 ~T 55 Medium, T 51 ~T 55 Two adjacent ones of 51 is an alkyl group 51 In the formula (6A), when X represents a group represented by the formula (6A), the alkyl groups may be bonded to each other to form a ring structure. 61 represents a sulfur atom, an oxygen atom, or —NR X1 - represents Y 6a and Y 6b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or -N=. X1 , R Y1 , R 61 , and R 62 Each of the symbols independently represents a hydrogen atom or a substituent. * represents a bonding position. However, the group represented by formula (6A) satisfies any one of the following requirements 6AA to 6AD. Requirement 6AA: Y 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 and R 62 represents a group other than an alkyl group. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and R 61 and R 62 At least one of the R represents an alkyl group. 61 and R 62 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and 61 and R 62 When both of Y and Y represent alkyl groups, the total number of carbon atoms in the alkyl groups is 2 or more. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 and R 62 At least one of the R represents an alkyl group. Y1 and the at least one R 61 and R 62 The total number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b one of which represents -N=, and R 61 and R 62 At least one of the R represents an alkyl group. 61 and R 62 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and 61 and R 62 In the formula (6B), when both of X represent an alkyl group, the total number of carbon atoms of the alkyl groups is 2 or more. 61 represents a sulfur atom, an oxygen atom, or —NR X1 - represents Y 6a and Y 6b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or -N=. X1 , R Y1 , and R 61 Each of the symbols independently represents a hydrogen atom or a substituent. * represents a bonding position. However, the group represented by formula (6B) satisfies any one of the following requirements 6BA to 6BD. Requirement 6BA: Y 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 represents a group other than an alkyl group. Y1 The alkyl group represented by the formula (I) has 2 or more carbon atoms. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and R 61 represents an alkyl group. 61 The alkyl group represented by the formula (I) has 2 or more carbon atoms. 6a and Y 6b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and R 61 represents an alkyl group. Y1 and the alkyl group represented by R 61 The total number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 6a and Y 6b one of which represents -N=, and R 61 represents an alkyl group. 61 In formula (7), the alkyl group represented by X has 2 or more carbon atoms. 71 represents a sulfur atom, an oxygen atom, -NR X1 -, -C(R X2 ) 2 -, or -Si(R X3 ) 2 - represents Y 7a and Y 7b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or =N-. 7 represents a monocyclic or condensed aromatic ring which may have a substituent. X1 , R X2 , R X3 , and R Y1 Each of Y independently represents a hydrogen atom or a substituent. However, the group represented by formula (7) satisfies any one of the following requirements 7A to 7J. Requirement 7A: Y 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of Y and Y represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 7 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 7 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 7 In the formula (7), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 and the alkyl group represented by R X2 The total number of carbon atoms in the alkyl groups represented by the formula (I) is 2 or more. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. X2 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of them is -CR Y1 =, and R Y1 represents an alkyl group, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 the alkyl group represented by R X2 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of the two represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atoms that are ring members of R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the above groups represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 7a and Y 7b One of the two represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 7 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 7 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 7 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 7 In the formula (7), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 7a and Y 7b One of the two represents -N=, and X 71 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 7 The carbon atom that is a ring atom of R has an alkyl group as a substituent. X2 and the alkyl group represented by Ar 7 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 7 In the formula (8), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 81 represents a sulfur atom, an oxygen atom, -NR X1 -, -C(R X2 ) 2 -, or -Si(R X3 ) 2 - represents Ar 8 represents a monocyclic or condensed aromatic ring which may have a substituent. 81 ~T 83 are each independently -CR 81 = or -N=. X1 , R X2 , R X3 , and R 81 Each independently represents a hydrogen atom or a substituent. 81 If there are multiple R 81 may be the same or different. * indicates a bonding position. However, the group represented by formula (8) satisfies any one of the following requirements 8A to 8G. Requirement 8A: T 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 81 ~T 83 Only one of the 81 is an alkyl group 81 When R represents 81 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 81 ~T 83 Two or more of the 81 is an alkyl group 81 When R = 81 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When T represents ≡ ... 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atoms that are ring members of R do not have alkyl groups as substituents. X2 When only one of R represents an alkyl group, the alkyl group has 2 or more carbon atoms, and X2 When both of the above groups represent alkyl groups, the total number of carbon atoms of the alkyl groups is 2 or more. 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 8 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 8 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atoms that are ring members of R do not have alkyl groups as substituents. 81 and the alkyl group represented by R X2 The total number of carbon atoms in the alkyl group represented by T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When T represents ≡ ... 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 represents a group other than -, and Ar 8 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 81 and the alkyl group represented by Ar 8 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When Ar represents ═ ... 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 81 ~T 83 But, R 81 is an alkyl group 81 represents a group other than =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atom that is a ring atom of R has an alkyl group as a substituent. X2 and the alkyl group represented by Ar 8 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 8 In the formula (8), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 81 ~T 83 At least one of 81 is an alkyl group 81 =, and X 81 But two R X2 At least one of the —C(R X2 ) 2 -, and Ar 8 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 81 the alkyl group represented by R X2 and the alkyl group represented by Ar 8 The carbon atom which is a ring atom of T has as a substituent an alkyl group having two or more carbon atoms. 81 ~T 83 Medium, T 81 ~T 83 Two adjacent ones of 81 is an alkyl group 81 When Ar represents ═ ... 8 In the formula (9), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. 91 represents a sulfur atom, an oxygen atom, or —NR X1 - represents Ar 9 represents a monocyclic or condensed aromatic ring which may have a substituent. 91 ~T 93 are each independently -CR 91 = or -N=. X1 and R 91 represents a hydrogen atom or a substituent. 91 If there are multiple R 91 may be the same or different. * indicates a bonding position. However, the group represented by formula (9) satisfies any one of the following requirements 9A to 9C. Requirement 9A: T 91 ~T 93 At least one of 91 is an alkyl group 91 = and Ar 9 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 91 ~T 93 Only one of the 91 is an alkyl group 91 When R represents 91 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 91 ~T 93 Two or more of the 91 is an alkyl group 91 When R = 91 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 91 ~T 93 Medium, T 91 ~T 93 Two adjacent ones of 91 is an alkyl group 91 When T represents a substituted or unsubstituted alkyl group, the alkyl groups may be bonded to each other to form a ring structure. 91 ~T 93 But, R 91 is an alkyl group 91 represents a group other than . 9 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 9 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 9 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 9 In the formula (9), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 91 ~T 93 At least one of 91 is an alkyl group 91 = and Ar 9 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 91 and the alkyl group represented by Ar 9 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 91 ~T 93 Medium, T 91 ~T 93 Two adjacent ones of 91 is an alkyl group 91 When Ar represents ═ ... 9 In formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b one of which is a sulfur atom, an oxygen atom, or —NR X1 -, and the other is -CR Y1 = or =N-. 10 represents a monocyclic or condensed aromatic ring which may have a substituent. 10 and T 11 are each independently -CR 101 = or -N=. X1 , R 101 , and R Y1 Each independently represents a hydrogen atom or a substituent. 101 If there are multiple R 101 and may be the same or different. * indicates a bonding position. However, the group represented by formula (10) satisfies any one of the following requirements 10A to 10J. Requirement 10A: Y 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 The number of carbon atoms in the alkyl group represented by the formula (I) is 2 or more. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 10 and T 11 Only one of the 101 is an alkyl group 101 When R represents 101 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 10 and T 11 Both of them are R 101 is an alkyl group 101 When the two R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 10 When there is only one alkyl group in Ar, the alkyl group has two or more carbon atoms, 10 When the alkyl group in Ar is two or more, the total number of carbon atoms of the two or more alkyl groups is two or more. 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of R do not have alkyl groups as substituents. Y1 and the alkyl group represented by R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 and the alkyl group represented by Ar 10 The total number of carbon atoms of the alkyl groups substituted on the carbon atoms that are ring atoms of Ar is 2 or more. 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents a group other than an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 101 and the alkyl group represented by Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 In the formula (10), when adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of them is -CR Y1 =, and R Y1 represents an alkyl group, T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. Y1 the alkyl group represented by R 101 and the alkyl group represented by Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 In the formula (10), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atoms that are ring members of T do not have alkyl groups as substituents. 10 and T 11 Only one of the 101 is an alkyl group 101 When R represents 101 The alkyl group represented by the formula (I) has 2 or more carbon atoms, and T 10 and T 11 Both of them are R 101 is an alkyl group 101 When the two R 101 The total number of carbon atoms in the alkyl groups represented by T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Y represents ═, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 But, R 101 is an alkyl group 101 represents a group other than . 10 The carbon atom that is a ring atom of Ar has an alkyl group as a substituent. 10 When Ar has only one alkyl group as a substituent, the alkyl group has two or more carbon atoms, and 10 When Ar has two or more alkyl groups as substituents, the total number of carbon atoms of the two or more alkyl groups is two or more. 10 In the formula (10), when adjacent carbon atoms that are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be bonded to each other to form a ring structure. 10a and Y 10b One of the two represents -N=, and T 10 and T 11 At least one of 101 is an alkyl group 101 = and Ar 10 The carbon atom that is a ring atom of R has an alkyl group as a substituent. 101 and the alkyl group represented by Ar 10 The total number of carbon atoms in the alkyl groups substituted on the carbon atoms that are ring atoms of T is 2 or more. 10 and T 11 are respectively R 101 is an alkyl group 101 When Ar represents ═ ... 10 When adjacent carbon atoms in the ring each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure.
16. In the formula (1-1), the X 1 ~The above X 4 However, both are -C (=Y X )-, and the Y X each independently represents an oxygen atom or ═CR W3 R W4 16. The compound of claim 15, wherein 17. The compound according to claim 15, wherein the compound represented by formula (1-1) is a compound represented by any one of formulas (1-3) to (1-6). In formulas (1-3) to (1-6), D 1 and D 2 each independently represents a group selected from the group consisting of groups represented by formulas (3) to (10). m1 and m2 each independently represent 0 or 1. R 1 ~R 6 Each independently represents a hydrogen atom or a substituent. 1 ~Y 4 each independently represents a sulfur atom, an oxygen atom, or ═NR W2 , or =CR W3 R W4 Represents R W2 represents a hydrogen atom or a substituent. W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 R each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent. 131 , R 132 , R 141 ~R 144 , R 151 ~R 154 , R 161 , and R 162 each independently represents a hydrogen atom or a substituent selected from the group consisting of a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 to 7 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, a heteroaryl group having 3 to 20 ring members which may have a substituent, an alkoxy group having 1 to 3 carbon atoms which may have a substituent, an aryloxy group having 6 to 20 carbon atoms which may have a substituent, a cyano group, and a halogen atom.
18. A compound represented by formula (1-2). In formula (1-2), D 1 and D 2 Each independently represents a monocyclic or condensed aromatic ring group which may have a substituent. However, the aromatic ring group has at least one alkyl group bonded to a carbon atom which is a ring atom of the aromatic ring group as a substituent, and when the aromatic ring group has one alkyl group as the substituent, the alkyl group has 2 or more carbon atoms, and when the aromatic ring group has two or more alkyl groups as the substituent, the total carbon number of the two or more alkyl groups is 2 or more. In addition, in the aromatic ring group, when adjacent carbon atoms which are ring atoms each have an alkyl group bonded to the carbon atom, the alkyl groups may be linked to each other to form a ring structure. m1 and m2 each independently represent 0 or 1. R 1 ~R 6 Each independently represents a hydrogen atom or a substituent. 1 ~Y 4 each independently represents a sulfur atom, an oxygen atom, or ═NR W2 , or =CR W3 R W4 Represents R W2 represents a hydrogen atom or a substituent. W3 and R W4 each independently represents a cyano group, —SO 2 R W5 , -COOR W6 , or -COR W7 Represents R W5 ~R W7 each independently represents an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or an aliphatic heterocyclic group which may have a substituent.
19. In the formula (1-2), the Y 1 ~ The above Y 4 each independently represents an oxygen atom or ═CR W3 R W4 19. The compound of claim 18, wherein 20. The compound according to any one of claims 15 to 19, wherein m1 and m2 each represent 0.
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