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WO2024062871A1 - Dispositif de conversion photoélectrique, dispositif d'imagerie, photocapteur et composé - Google Patents

Dispositif de conversion photoélectrique, dispositif d'imagerie, photocapteur et composé Download PDF

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WO2024062871A1
WO2024062871A1 PCT/JP2023/031478 JP2023031478W WO2024062871A1 WO 2024062871 A1 WO2024062871 A1 WO 2024062871A1 JP 2023031478 W JP2023031478 W JP 2023031478W WO 2024062871 A1 WO2024062871 A1 WO 2024062871A1
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group
substituent
atom
aromatic ring
independently represent
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Japanese (ja)
Inventor
和平 金子
寛記 杉浦
健浩 山根
直幸 花木
潔 竹内
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Fujifilm Corp
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Priority to KR1020257007329A priority patent/KR20250050051A/ko
Publication of WO2024062871A1 publication Critical patent/WO2024062871A1/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/10—Integrated devices
    • H10F39/12—Image sensors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/60—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation in which radiation controls flow of current through the devices, e.g. photoresistors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/80—Constructional details
    • H10K30/81—Electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
    • H10K39/30—Devices controlled by radiation
    • H10K39/32—Organic image sensors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a photoelectric conversion element, an image sensor, an optical sensor, and a compound.
  • Patent Document 1 discloses the following compound.
  • Patent Document 2 discloses the following compound.
  • photoelectric conversion elements are required to be suitable for vapor deposition manufacturing, have high quantum efficiency when receiving red and green light (particularly light with a wavelength of 600 nm), and be excellent in electric field strength dependence of response speed.
  • Vapor deposition manufacturing suitability means that a photoelectric conversion film included in a photoelectric conversion element can be manufactured by vapor deposition without any problem.
  • red-green light means light with a wavelength in the range of 500 to 700 nm.
  • the present inventors referred to the compounds disclosed in Patent Documents 1 and 2, and studied the resulting photoelectric conversion elements, and found that the suitability for vapor deposition manufacturing, quantum efficiency when receiving red-green light, and dependence of response speed on electric field strength. I found it difficult to come to terms with sex.
  • the photoelectric conversion element according to [1], wherein the compound represented by formula (1) above includes a compound represented by formula (3) described below.
  • Ar 1 represents a monocyclic aromatic ring group.
  • the photoelectric conversion element according to any one of [1] to [5].
  • the photoelectric conversion film further includes an n-type organic semiconductor, Any one of [1] to [7], wherein the photoelectric conversion film has a bulk heterostructure formed by a mixture of the compound represented by the formula (1) and an n-type organic semiconductor.
  • the photoelectric conversion film further contains a p-type organic semiconductor.
  • the present invention it is possible to provide a photoelectric conversion element that is excellent in vapor deposition manufacturing suitability, quantum efficiency when receiving red and green light, and electric field strength dependence of response speed. Moreover, according to the present invention, an image sensor, a photosensor, and a compound related to the above photoelectric conversion element can also be provided.
  • FIG. 1 is a schematic cross-sectional view showing one configuration example of a photoelectric conversion element.
  • FIG. 1 is a schematic cross-sectional view showing one configuration example of a photoelectric conversion element.
  • a numerical range expressed using " ⁇ " means a range that includes the numerical values written before and after " ⁇ " as lower and upper limits.
  • the hydrogen atom may be either a light hydrogen atom (normal hydrogen atom) or a deuterium atom (for example, a double hydrogen atom).
  • substituents, linking groups, etc. hereinafter also referred to as “substituents, etc." indicated by specific symbols, or when multiple substituents, etc. are specified at the same time, each substituent The terms may be the same or different from each other. The same applies to the number of substituents and the like.
  • examples of the substituent include groups exemplified by the substituent W described below, unless otherwise specified.
  • the substituent W is, for example, 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 (cycloalkenyl and bicycloalkenyl groups), alkynyl groups, aryl groups, heteroaryl groups, cyano groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclicoxy groups, acyloxy groups, carbamoyloxy groups, alkoxycarbonyloxy group, aryloxycarbonyloxy group, secondary or tertiary amino group (including anilino group), alkylthio group, arylthio group, heterocyclic thio group, alkyl or arylsulfiny
  • each of the above-mentioned groups may further have a substituent (for example, one or more of the above-mentioned groups), if possible.
  • a substituent for example, one or more of the above-mentioned groups
  • an alkyl group which may have a substituent is also included as one form of the substituent W.
  • the substituent W has a carbon atom
  • the number of carbon atoms in the substituent W is, for example, 1 to 20.
  • the number of atoms other than hydrogen atoms in the substituent W is, for example, 1 to 30.
  • the specific compounds mentioned below include a carboxy group, a salt of a carboxy group, a salt of a phosphoric acid group, a sulfonic acid group, a salt of a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, and a ureido group as substituents. , a boronic acid group (-B(OH) 2 ) and/or a primary amino group.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • 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 methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, n-hexyl group and cyclopentyl group. Further, the alkyl group may be any of a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group, and may have a cyclic structure of these as a partial structure.
  • examples of the substituent which the alkyl group may have include the groups exemplified by the substituent W, and an aryl group (preferably having 6 to 18 carbon atoms). , more preferably 6 carbon atoms), a heteroaryl group (preferably 5 to 18 carbon atoms, more preferably 5 to 6 carbon atoms), or a halogen atom (preferably a fluorine atom or a chlorine atom).
  • the alkyl group moiety in the alkoxy group is preferably the above alkyl group.
  • the alkyl group moiety in the alkylthio group is preferably the above alkyl group.
  • examples of the substituent which the alkoxy group may have are the same as those for the alkyl group which may have a substituent.
  • examples of the substituent which the alkylthio group may have are the same as those for the alkyl group which may have a substituent.
  • the alkenyl group may be linear, branched, or cyclic.
  • the alkenyl group preferably has 2 to 20 carbon atoms.
  • examples of the substituent which the alkenyl group may have are the same as those for the alkyl group which may have a substituent.
  • an alkynyl group may be linear, branched, or cyclic.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 20.
  • examples of the substituent which the alkynyl group may have are the same as those for the alkyl group which may have a substituent.
  • 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).
  • 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) aromatic ring is an aromatic ring having a plurality of (e.g., 2 to 6 rings) aromatic ring structures condensed as ring structures.
  • the aromatic ring preferably has 5 to 15 ring members.
  • the aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocycle.
  • the number of heteroatoms contained as ring member atoms is, for example, 1 to 10.
  • 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.
  • the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, and a fluorene ring.
  • aromatic heterocycle examples include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring (for example, a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring), a tetrazine ring (for example, a 1,2,4,5-tetrazine ring), a quinoxaline ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzopyrrole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a naphthopyr
  • the type of the substituent which the aromatic ring may have may be, for example, the groups exemplified as the substituent W.
  • the number of the substituents may be 1 or more (for example, 1 to 4, etc.).
  • aromatic ring group includes, for example, groups obtained by removing one or more (eg, 1 to 5, etc.) hydrogen atoms from the above-mentioned aromatic ring.
  • aryl group includes, for example, a group obtained by removing one hydrogen atom from a ring that corresponds to an aromatic hydrocarbon ring among the above aromatic rings.
  • heteroaryl group includes, for example, a group in which one hydrogen atom has been removed from a ring corresponding to an aromatic heterocycle among the above aromatic rings.
  • arylene group includes, for example, a group formed by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings.
  • heteroarylene group includes, for example, a group formed by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above aromatic rings.
  • the types of the substituents which these groups may have include, for example, the groups exemplified for the substituent W.
  • the number of the substituents may be 1 or more (for example, 1 to 4, etc.).
  • a formula showing a chemical structure contains a plurality of identical symbols indicating the type or number of groups
  • the contents of the plurality of identical symbols are independent of each other, and the contents of the plurality of identical symbols may be the same or different.
  • a formula showing a chemical structure contains a plurality of groups of the same type (for example, alkyl groups, etc.)
  • the specific contents of the plurality of groups of the same type are independent of each other, and the specific contents of the groups of the same type may be the same or different.
  • the bonding direction of the divalent groups (eg, -CO-O-, etc.) described herein is not limited unless otherwise specified.
  • Y in a compound represented by the formula "X-Y-Z" is -CO-O-
  • the above compound has the formula "X-O-CO-Z" and "X-CO-O- Z" may be used.
  • the general formula or structural formula representing the above compound is described only in the form of either the cis form or the trans form for convenience. There may be cases. Even in such a case, unless otherwise specified, the form of the above compound is not limited to either the cis form or the trans form, and the above compound may be either the cis form or the trans form. It may be a form.
  • 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, wherein the photoelectric conversion film is a compound represented by formula (1) (hereinafter referred to as " (Also referred to as “specific compounds.”)
  • the photoelectric conversion element of the present invention has the above configuration, the mechanism by which the problems of the present invention can be solved is not necessarily certain, but the inventors of the present invention speculate as follows.
  • the specific compound is a compound having a donor moiety (D) and an acceptor moiety (A) (so-called ADA type compound).
  • the specific compound has a three-ring condensed ring (ring containing X 1 to X 4 and NR 3 ) with a predetermined structure in the donor part, and an aromatic ring group (Ar 1 and Ar 2 ) in the part adjacent to the donor part. It further has a predetermined group in the R3 portion. It is assumed that the specific compound having the above-mentioned characteristic structure is less likely to cause aggregation due to ⁇ - ⁇ stacking or the like. In other words, aggregation of specific compounds is suppressed in the photoelectric conversion film containing specific compounds, and as a result, charge separation in the photoelectric conversion film proceeds efficiently without being inhibited, resulting in an excellent photoelectric conversion element. It is presumed that the quantum efficiency is high.
  • FIG. 1 shows a schematic cross-sectional view of an embodiment of the photoelectric conversion element of the present invention.
  • the photoelectric conversion element 10a shown in FIG. 1 includes a conductive film 11 functioning as a lower electrode (hereinafter also referred to as "lower electrode”), an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and an upper electrode. It has a structure in which a transparent conductive film (hereinafter also referred to as "upper electrode”) 15 that functions as an upper electrode is laminated in this order.
  • FIG. 2 shows a configuration example of another photoelectric conversion element.
  • FIGS. 1 and 2 has a structure in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are laminated 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.
  • the photoelectric conversion element 10a it is preferable that light be incident on the photoelectric conversion film 12 via the upper electrode 15. Further, when using the photoelectric conversion element 10a (or 10b), a voltage can be applied. In this case, it is preferable that the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and a voltage of 1 ⁇ 10 ⁇ 5 to 1 ⁇ 10 7 V/cm is applied between the pair of electrodes. In terms of performance and power consumption, the applied voltage is more preferably 1 ⁇ 10 ⁇ 4 to 1 ⁇ 10 7 V/cm, and even more preferably 1 ⁇ 10 ⁇ 3 to 5 ⁇ 10 6 V/cm. Regarding the voltage application method, in FIGS.
  • the photoelectric conversion element 10a (or 10b) is used as a photosensor or incorporated into an image sensor, 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 applied to an image sensor. Below, the form of each layer constituting the photoelectric conversion element of the present invention will be explained in detail.
  • the photoelectric conversion element has a photoelectric conversion film.
  • the photoelectric conversion film contains a compound represented by formula (1).
  • R 1 and R 2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, a cyano group, or a halogen atom.
  • R 3 is an aliphatic hydrocarbon group having 7 or less carbon atoms which may have -O- and a halogen atom, or an aromatic ring group which may have a substituent. represent.
  • R X1 and R X3 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X2 and R X4 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, an aromatic ring group that may have a substituent, or a halogen atom.
  • Ar 1 and Ar 2 each independently represent an aromatic ring group which may have a substituent.
  • R Y1 represents a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, or an aromatic ring group which may have a substituent.
  • R Y4 to R Y7 each independently represent an aliphatic hydrocarbon group that may have a substituent or an aromatic ring group that may have a substituent.
  • a 1 and A 2 each independently represent a ring containing two or more carbon atoms and optionally having a substituent.
  • One of n 1 and n 2 represents 1, and the other represents 0 or 1.
  • R 1 and R 2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, a cyano group, or a halogen atom.
  • the aliphatic hydrocarbon group which may have a substituent may be linear, branched or cyclic.
  • the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, with a saturated aliphatic hydrocarbon group being preferred.
  • the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 10, even more preferably 1 to 3.
  • the aliphatic hydrocarbon group is preferably an alkyl group that may have a substituent (for example, a trifluoromethyl group).
  • substituents for example, a trifluoromethyl group.
  • substituent W examples of the substituent that the aliphatic hydrocarbon group may have include those exemplified by the substituent W, with a halogen atom being preferred and a fluorine atom being more preferred.
  • Hydrogen atoms are preferred as R 1 and R 2 .
  • R 3 may have -O-, and may have an aliphatic hydrocarbon group having 7 or less carbon atoms or a substituent that may have a halogen atom Represents an aromatic ring group.
  • the aliphatic hydrocarbon group having 7 or less carbon atoms, which may have -O- and may have a halogen atom may be linear, branched, or cyclic.
  • the aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, with a saturated aliphatic hydrocarbon group being preferred.
  • the number of carbon atoms in the aliphatic hydrocarbon group is 7 or less, preferably 2 to 7, more preferably 3 to 7, and even more preferably 5 to 7.
  • the aliphatic hydrocarbon group is preferably a branched aliphatic hydrocarbon group having 5 to 7 carbon atoms.
  • the aromatic ring group which may have a substituent may be either monocyclic or polycyclic.
  • the aromatic ring group may be either an aryl group that may have a substituent or a heteroaryl group that may have a substituent.
  • the number of carbon atoms in the aromatic ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10.
  • the said carbon number is a value which includes the carbon atom of a substituent.
  • the aromatic ring is preferably an aryl group that may have a substituent, and more preferably a phenyl group that may have a substituent.
  • substituents that the aromatic ring group may have include substituents exemplified by the substituent W, such as a halogen atom, a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, and a linear aliphatic hydrocarbon group having 3 carbon atoms.
  • R 3 is preferably a phenyl group which may have a substituent or a branched aliphatic hydrocarbon group having 5 to 7 carbon atoms, since the effects of the present invention are more excellent.
  • linear aliphatic hydrocarbon group having 1 to 3 carbon atoms examples include linear alkyl groups having 1 to 3 carbon atoms (for example, methyl group, ethyl group, n-propyl group, etc.). is preferably an ethyl group or a methyl group, and more preferably a methyl group.
  • Examples of the branched aliphatic hydrocarbon group having 3 to 5 carbon atoms include branched alkyl groups having 3 to 5 carbon atoms (for example, isopropyl group, sec-butyl group, iso-butyl group, tert -butyl group, neopentyl group, etc.), isopropyl group, sec-butyl group, iso-butyl group or tert-butyl group are preferred, and isopropyl group is more preferred.
  • Examples of the cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms include cycloalkyl groups having 3 to 8 carbon atoms (e.g., cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc.).
  • cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group are preferred, and a cyclopropyl group is more preferred.
  • R 3 is preferably a group represented by formula (R-1) or a group represented by formula (R-2), and a group represented by formula (R-2) or a group represented by formula (R-3) is preferable.
  • the groups represented are more preferred.
  • R-1 * represents a bonding position.
  • B represents a monocyclic aromatic ring containing two or more carbon atoms and optionally having a substituent.
  • R B1 is an aliphatic hydrocarbon group that may have a substituent, a silyl group that may have a substituent, an alkoxy group that may have a substituent, or an aliphatic hydrocarbon group that may have a substituent. represents an aromatic ring group, a cyano group, or a halogen atom.
  • B represents a monocyclic aromatic ring containing two or more carbon atoms and optionally having a substituent.
  • the two or more carbon atoms contained in the aromatic ring represented by B include the two carbon atoms specified in formula (R-1), and may also contain carbon atoms other than those carbon atoms. means.
  • the number of carbon atoms in the aromatic ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10.
  • the number of carbon atoms above includes the two carbon atoms specified in formula (R-1), and if the aromatic ring has a substituent, it is a value that includes the carbon atom of the substituent.
  • the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle.
  • the aromatic ring is preferably an aromatic hydrocarbon ring which may have a substituent, and more preferably a benzene ring which may have a substituent.
  • R B1 is an aliphatic hydrocarbon group that may have a substituent, a silyl group that may have a substituent, or an alkoxy group that may have a substituent. , represents an aromatic ring group that may have a substituent, a cyano group, or a halogen atom.
  • R B1 is preferably an alkyl group or a halogen atom which may have a substituent.
  • the alkyl group that may have a substituent may be linear, branched, or cyclic.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 3.
  • substituents that the aromatic ring represented by B, the aliphatic hydrocarbon group, the silyl group, the alkoxy group, and the aromatic ring group represented by R B1 may have include, for example, substituents Examples include groups exemplified by W, with an alkyl group or a halogen atom being preferred.
  • R C1 each independently represents a hydrogen atom, a methyl group, an isopropyl group or a t-butyl group.
  • the number of carbon atoms in the group represented by formula (R-2) is 3 to 7, and two or more of the three R C1 are other than hydrogen atoms. Note that the number of carbon atoms in the group represented by formula (R-2) above means the total number of all carbon atoms contained in the group represented by formula (R-2).
  • the number of R C1 's representing groups other than hydrogen atoms is not particularly limited as long as it is two or more (2 or 3), but among the three R C1 's, one is a hydrogen atom and the remaining two are hydrogen atoms. Preferably, it is a group other than . As the group other than the hydrogen atom, a methyl group or an isopropyl group is preferable. A plurality of R C1s may be the same or different.
  • R B2 and R B3 each independently represent an alkyl group that may have a substituent or an aromatic ring group that may have a substituent.
  • R B4 represents a hydrogen atom or a substituent.
  • R B2 and R B3 each independently represent an alkyl group that may have a substituent or an aromatic ring group that may have a substituent.
  • the alkyl group include the alkyl group represented by R B1 which may have a substituent.
  • the above-mentioned aromatic ring group include an aromatic ring group which may have a substituent represented by R B1 .
  • R B2 and R B3 an alkyl group which may have a substituent or an aryl group which may have a substituent is preferable, and an alkyl group which may have a substituent is more preferable.
  • R B4 represents a hydrogen atom or a substituent.
  • Examples of the above-mentioned substituent include groups exemplified by the substituent W, and an alkyl group is preferable.
  • R B4 is preferably a hydrogen atom or an alkyl group.
  • R X1 each independently represents a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X2 each independently represents a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, or a halogen atom.
  • aliphatic hydrocarbon groups which may have substituents represented by R 1 and R 2 examples include groups.
  • the aromatic ring group which may have a substituent represented by R X1 and R X2 include, for example, the aromatic ring group which may have a substituent represented by R 3 .
  • R X1 is preferably a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms or an aromatic ring group which may have a substituent.
  • R X2 is preferably a hydrogen atom, a halogen atom, or a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms. It is preferable that one of X 1 and X 2 represents a sulfur atom and the other represents -CR (X represents a halogen atom) is more preferable.
  • R X3 each independently represents a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X4 each independently represents a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, an aromatic ring group that may have a substituent, or a halogen atom.
  • R X3 has the same meaning as R X1 , and preferred embodiments are also the same.
  • R X4 has the same meaning as R X2 , and preferred embodiments are also the same. It is preferable that one of X 3 and X 4 represents a sulfur atom and the other represents -CR (X represents a halogen atom) is more preferable.
  • the dotted line clearly drawn between X 2 and the adjacent carbon atom represents a single line (single bond) when X 2 represents an oxygen atom, a sulfur atom, a selenium atom, or -NR
  • X 2 represents an oxygen atom, a sulfur atom, a selenium atom, or -NR
  • -CR X2 or a nitrogen atom
  • X 3 represents an oxygen atom, a sulfur atom, a selenium atom, or -NR
  • Ar 1 and Ar 2 each independently represent an aromatic ring group which may have a substituent.
  • the aromatic ring group (bivalent aromatic ring group) which may have a substituent may be either monocyclic or polycyclic.
  • the aromatic ring group may be either an arylene group that may have a substituent or a heteroarylene group that may have a substituent.
  • the number of carbon atoms in the aromatic ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 15.
  • the said carbon number is a value which includes the carbon atom of a substituent.
  • Examples of the aromatic ring group include a monocyclic arylene group that may have a substituent, a polycyclic arylene group that may have a substituent, and a monocyclic arylene group that may have a substituent.
  • Examples include a heteroarylene group and a polycyclic heteroarylene group that may have a substituent, and monocyclic aromatic groups that may have a substituent ( A monocyclic arylene group which may have a substituent or a monocyclic heteroarylene group which may have a substituent is preferred.
  • Examples of the heteroatoms constituting the monocyclic and polycyclic heteroarylene groups include nitrogen atoms, oxygen atoms, and sulfur atoms, and preferably contain at least an oxygen atom or a sulfur atom.
  • the number of rings constituting the polycyclic arylene group and the polycyclic heteroarylene group is preferably 2 to 10, more preferably 2 or 3, and even more preferably 2 (in other words, the number of rings constituting the polycyclic arylene group and the polycyclic heteroarylene group is preferably 2 to 10, more preferably 2 or 3, and even more preferably 2).
  • a 2-ring arylene group which may have a substituent or a 2-ring heteroarylene group which may have a substituent is more preferable.
  • the above two-ring arylene group is preferably a two-ring condensed ring arylene group which may have a substituent.
  • the two-ring heteroarylene group is preferably a two-ring condensed heteroarylene group which may have a substituent.
  • substituents that the aromatic ring group may have include substituents exemplified by substituent W, such as an aromatic ring group that may have a substituent represented by R3 , a halogen atom, A linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 5 carbon atoms, or a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms is preferred.
  • X A1 represents a sulfur atom, an oxygen atom, a selenium atom or -NR Z2 -.
  • R Z2 and R Z3 each independently represent a hydrogen atom or a substituent.
  • * represents the bonding position.
  • X A2 represents a sulfur atom, an oxygen atom, a selenium atom or -NR Z4 -.
  • R Z4 to R Z7 each independently represent a hydrogen atom or a substituent.
  • * represents the bonding position.
  • X A5 represents a sulfur atom, an oxygen atom, a selenium atom or -NR Z8 -.
  • R Z8 and R Z9 each independently represent a hydrogen atom or a substituent.
  • * represents the bonding position.
  • R Z10 represents a hydrogen atom or a substituent.
  • R Z1 represents a hydrogen atom or a substituent.
  • -CR Z1 is preferable.
  • the substituent represented by R Z1 include the groups exemplified by the substituent W, including a halogen atom, a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, or an alkoxy group (preferably, methoxy group) is preferred.
  • R Z1 a hydrogen atom is preferable.
  • the monocyclic ring formed by two R Z1s connected to each other includes a monocyclic aromatic ring and a monocyclic alicyclic ring that may contain a hetero atom.
  • a monocyclic alicyclic ring (preferably a cycloalkyl group) which may contain atoms is preferred.
  • X A1 represents a sulfur atom, an oxygen atom, a selenium atom, or -NR Z2 -.
  • X A1 an oxygen atom or a sulfur atom is preferable.
  • R Z2 and R Z3 each independently represent a hydrogen atom or a substituent. Examples of the substituent represented by R Z2 include the substituents exemplified by the substituent W, and a linear aliphatic hydrocarbon group or an aromatic ring group having 1 to 3 carbon atoms is preferable.
  • R Z2 is preferably a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms or an aromatic ring group.
  • substituent represented by R Z3 include the substituents exemplified by the substituent W, including a halogen atom, a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms, or an alkoxy group (preferably , methoxy group) are preferred.
  • R Z3 is preferably a hydrogen atom, a halogen atom, or a linear aliphatic hydrocarbon group having 1 to 3 carbon atoms.
  • the monocyclic ring formed by connecting two R Z3 to each other includes a monocyclic aromatic ring and a monocyclic alicyclic ring which may contain a hetero atom.
  • a monocyclic alicyclic ring (preferably a cycloalkyl group) which may contain atoms is preferred.
  • X A2 represents a sulfur atom, an oxygen atom, a selenium atom or -NR Z4 -.
  • X A2 an oxygen atom or a sulfur atom is preferable.
  • R Z4 to R Z7 each independently represent a hydrogen atom or a substituent.
  • R Z4 and R Z6 have the same meaning as R Z2 , and the preferred embodiments are also the same.
  • R Z5 and R Z7 have the same meaning as R Z3 , and the preferred embodiments are also the same.
  • X A5 represents a sulfur atom, an oxygen atom, a selenium atom or -NR Z8 -.
  • X A5 is preferably an oxygen atom or a sulfur atom.
  • R Z8 and R Z9 each independently represent a hydrogen atom or a substituent.
  • R Z8 has the same meaning as R Z2 , and preferred embodiments are also the same.
  • R Z9 has the same meaning as R Z3 , and preferred embodiments are also the same.
  • R Z10 represents a hydrogen atom or a substituent.
  • R Z10 has the same meaning as R Z3 , and preferred embodiments are also the same.
  • Y 1 and Y 2 an oxygen atom or a sulfur atom is preferable, and an oxygen atom is more preferable.
  • R Y1 represents a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R Y4 to R Y7 each independently represent an aliphatic hydrocarbon group that may have a substituent or an aromatic ring group that may have a substituent. Examples of the aliphatic hydrocarbon group which may have a substituent represented by R Y1 include, for example, an aliphatic hydrocarbon group which may have a substituent represented by R 1 and R 2 . It will be done.
  • Examples of the aromatic ring group which may have a substituent represented by R Y1 include, for example, the aromatic ring group which may have a substituent represented by R 3 . It is preferable that at least one of R Y2 and R Y3 represents a cyano group, and it is more preferable that both R Y2 and R Y3 represent a cyano group.
  • Examples of the substituents that the groups represented by R Y1 to R Y7 may have include the substituents exemplified by substituent W.
  • a 1 and A 2 each independently represent a ring containing two or more carbon atoms and optionally having a substituent.
  • Two or more carbon atoms include the two carbon atoms specified in formula (1), and may further include carbon atoms other than those carbon atoms.
  • the number of carbon atoms in the ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10.
  • the number of carbon atoms above includes the two carbon atoms specified in formula (1), and if the ring has a substituent, it is a value that includes the carbon atom of the substituent.
  • the above-mentioned ring may be either aromatic or non-aromatic.
  • the above-mentioned ring may be either a monocyclic ring or a polycyclic ring, and is preferably a 5-membered ring, a 6-membered ring, or a fused ring containing at least one of a 5-membered ring and a 6-membered ring.
  • the number of rings forming the above condensed ring is preferably 1 to 4, more preferably 1 to 3.
  • the above ring may contain a heteroatom.
  • heteroatom examples include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom, and boron atom, with sulfur atom, nitrogen atom, or oxygen atom being preferred.
  • the number of heteroatoms in the ring is preferably 0 to 10, more preferably 0 to 5.
  • other carbonyl carbons and other thiocarbonyl carbons mean carbonyl carbons and thiocarbonyl carbons whose constituent elements are carbon atoms other than the above C A and the above C B among the carbon atoms constituting the ring.
  • Examples of the substituent that the ring may have include those exemplified by the substituent W, preferably a halogen atom, an alkyl group, an aromatic ring group, or a silyl group, and more preferably a halogen atom or an alkyl group.
  • the alkyl group may be linear, branched, or cyclic, and preferably linear.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 3.
  • a ring used as an acidic nucleus for example, an acidic nucleus in a merocyanine dye, etc.
  • examples include the following cores: (a) 1,3-dicarbonyl nucleus: for example, 1,3-indanedione nucleus, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione and 1,3-dioxane-4,6 - Zion et al.
  • (b) Pyrazolinone nucleus For example, 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, 3-cyano-1-phenyl-2-pyrazolin-5- one, 3-trifluoromethyl-1-phenyl-2-pyrazolin-5-one and 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one.
  • (c) Isoxazolinone core for example, 3-phenyl-2-isoxazolin-5-one and 3-methyl-2-isoxazolin-5-one.
  • (d) Oxindole nucleus For example, 1-alkyl-2,3-dihydro-2-oxindole.
  • (e) 2,4,6-trioxohexahydropyrimidine core for example, barbituric acid, 2-thiobarbituric acid and its derivatives.
  • Examples of the above derivatives include 1-alkyl derivatives such as 1-methyl and 1-ethyl; 1,3-dialkyl derivatives such as 1,3-dimethyl, 1,3-diethyl and 1,3-dibutyl; -diphenyl, 1,3-diaryls such as 1,3-di(p-chlorophenyl) and 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1- such as 1-ethyl-3-phenyl Examples include aryl forms and 1,3-diheteroaryl forms such as 1,3-di(2-pyridyl).
  • 2-thio-2,4-thiazolidinedione nucleus for example, rhodanine and its derivatives.
  • examples of the above derivatives include 3-alkylrhodanines such as 3-methylrhodanine, 3-ethylrhodanine and 3-allyrrhodanine, 3-arylrhodanines such as 3-phenylrhodanine, and 3-( Examples include 3-heteroarylrhodanine such as 2-pyridyl)rhodanine.
  • 2-thio-2,4-oxazolidinedione nucleus (2-thio-2,4-(3H,5H)-oxazolidinedione nucleus): For example, 3-ethyl-2-thio-2,4-oxazolidinedione etc.
  • Thianaphthenone nucleus For example, 3(2H)-thianaphthenone-1,1-dioxide.
  • 2-thio-2,5-thiazolidinedione nucleus For example, 3-ethyl-2-thio-2,5-thiazolidinedione.
  • 2,4-thiazolidinedione nucleus for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione.
  • Thiazolin-4-one nucleus for example, 4-thiazolinone and 2-ethyl-4-thiazolinone.
  • 2,4-imidazolidinedione (hydantoin) core for example, 2,4-imidazolidinedione and 3-ethyl-2,4-imidazolidinedione.
  • 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidine Zion et al.
  • Imidazolin-5-one nucleus For example, 2-propylmercapto-2-imidazolin-5-one.
  • 3,5-pyrazolidinedione nucleus for example, 1,2-diphenyl-3,5-pyrazolidinedione and 1,2-dimethyl-3,5-pyrazolidinedione.
  • Benzothiophen-3(2H)-one nucleus for example, benzothiophen-3(2H)-one, oxobenzothiophen-3(2H)-one, dioxobenzothiophen-3(2H)-one, etc.
  • Indanone nucleus for example, 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone 3-(dicyanomethylidene)-1-indanone and 3 , 3-dimethyl-1-indanone, etc.
  • Benzofuran-3-(2H)-one nucleus For example, benzofuran-3-(2H)-one.
  • one of n1 and n2 represents 1, and the other represents 0 or 1. It is preferred that one of n1 and n2 represents 1 and the other represents 0.
  • a compound represented by formula (1-C-1) or a compound represented by formula (1-C-2) is preferable, and a compound represented by formula (1-C-1) is more preferable. preferable.
  • R 1 and R 2 represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, a cyano group, or a halogen atom.
  • R 3 represents an aliphatic hydrocarbon group having 7 or less carbon atoms which may have -O-, a halogen atom, or an aromatic ring group which may have a substituent.
  • R X1 and R X3 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X2 and R X4 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, an aromatic ring group that may have a substituent, or a halogen atom.
  • Ar 1 and Ar 2 each independently represent an aromatic ring group which may have a substituent.
  • n 1 and n 2 represent 1, and the other represents 0 or 1.
  • R C11 represents a hydrogen atom or a substituent.
  • R C12 and R C13 each independently represent a cyano group, -SO 2 R C14 , -COOR C15 or -COR C16 .
  • R C14 to R C16 each independently represent an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group, or an optionally substituted heterocyclic group represents.
  • C represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
  • R 1 and R 2 represent a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, a cyano group, or a halogen atom.
  • R 3 represents an aliphatic hydrocarbon group having 7 or less carbon atoms which may have -O-, a halogen atom, or an aromatic ring group which may have a substituent.
  • R X1 and R X3 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X2 and R X4 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, an aromatic ring group that may have a substituent, or a halogen atom.
  • Ar 1 and Ar 2 each independently represent an aromatic ring group which may have a substituent.
  • n 1 and n 2 represents 1, and the other represents 0 or 1.
  • R C21 represents a hydrogen atom or a substituent.
  • R C22 and R C23 each independently represent a cyano group, -SO 2 R C24 , -COOR C25 or -COR C26 .
  • R C24 to R C26 each independently represent an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group, or an optionally substituted heterocyclic group represents.
  • R CX1 and R CX2 each independently represent a hydrogen atom or a substituent.
  • R 1 to R 3 , X 1 to X 4 , Ar 1 , Ar 2 , n 1 and n 2 are each in formula (1) , R 1 to R 3 , X 1 to X 4 , Ar 1 , Ar 2 , n 1 and n 2 and the preferred embodiments are also the same.
  • Examples of the groups represented by X C1 and X C2 include groups represented by Y 1 and Y 2 .
  • the two or more carbon atoms contained in the aromatic ring represented by C include the two carbon atoms specified in formula (C-1), and may also contain carbon atoms other than those carbon atoms. means.
  • the number of carbon atoms in the aromatic ring is preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 10.
  • the above carbon number includes the two carbon atoms specified in formula (C-1), and if the aromatic ring has a substituent, it is a value that includes the carbon atom of the substituent.
  • the aromatic ring represented by C include the aromatic ring represented by B in formula (R-1).
  • the heterocyclic group represented by R C14 to R C16 which may have a substituent may be either aromatic or non-aromatic.
  • the substituents that the aromatic ring, the aliphatic hydrocarbon group, the aryl group, and the heterocyclic group may have include groups exemplified by the substituent W, such as an alkyl group, an alkoxy group, and an aryl group. , a heteroaryl group or a halogen atom.
  • R C21 examples include the substituents exemplified by substituent W. It is preferable that at least one of R C22 and R C23 represents a cyano group, and it is more preferable that both R C22 and R C23 represent a cyano group.
  • the heterocyclic group represented by R C24 to R C26 which may have a substituent may be either aromatic or non-aromatic.
  • Examples of the substituents that the aliphatic hydrocarbon group, the aryl group, and the heterocyclic group represented by R C24 to R C26 may have include the substituents exemplified by the substituent W.
  • the substituents represented by R CX1 and R CX2 include, for example, the groups exemplified by substituent W, and are preferably an alkyl group or a phenyl group, and more preferably an alkyl group.
  • the phenyl group may further have a substituent.
  • the specific compound includes a compound represented by formula (2) or a compound represented by formula (3).
  • R 1 and R 2 represent a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, a cyano group, or a halogen atom.
  • R 3 is an aliphatic hydrocarbon group having 7 or less carbon atoms which may have -O- and a halogen atom, or an aromatic ring group which may have a substituent. represent.
  • R X1 and R X3 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X2 and R X4 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, an aromatic ring group that may have a substituent, or a halogen atom.
  • Ar 1 and Ar 2 each independently represent an aromatic ring group which may have a substituent.
  • a 3 and A 4 each independently represent a ring containing 3 or more carbon atoms and optionally having a substituent.
  • One of n 1 and n 2 represents 1, and the other represents 0 or 1.
  • R 1 to R 3 , X 1 to X 4 , Ar 1 , Ar 2 , n 1 and n 2 are respectively R 1 to R 3 , X 1 to X 4 , It has the same meaning as Ar 1 , Ar 2 , n 1 and n 2 , and the preferred embodiments are also the same.
  • the three or more carbon atoms included in the rings represented by A3 and A4 include the three carbon atoms specified in formula (2), and may further include carbon atoms other than those carbon atoms. It means that.
  • the above-mentioned ring includes, for example, two or more carbon atoms represented by A1 and A2 , contains three or more carbon atoms of the ring that may have a substituent, and has a substituent. Examples include rings that may be
  • R 1 and R 2 represent a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, a cyano group, or a halogen atom.
  • R 3 is an aliphatic hydrocarbon group having 7 or less carbon atoms which may have -O- and a halogen atom, or an aromatic ring group which may have a substituent. represent.
  • R X1 and R X3 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aromatic ring group that may have a substituent.
  • R X2 and R X4 each independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, an aromatic ring group that may have a substituent, or a halogen atom.
  • Ar 1 represents an aromatic ring group which may have a substituent.
  • R Y1 represents a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, or an aromatic ring group which may have a substituent.
  • R Y4 to R Y7 each independently represent an aliphatic hydrocarbon group that may have a substituent or an aromatic ring group that may have a substituent.
  • a 1 and A 2 each independently represent a ring containing two or more carbon atoms and optionally having a substituent.
  • R 1 to R 3 , X 1 to X 4 , Ar 1 , Y 1 , Y 2 , A 1 and A 2 are R 1 to R 3 , X 1 to It has the same meaning as X 4 , Ar 1 , Y 1 , Y 2 , A 1 and A 2 , and the preferred embodiments are also the same.
  • the molecular weight of the specific compound is preferably 400 to 1,200, more preferably 400 to 1,000, even more preferably 400 to 800.
  • the sublimation temperature of the specific compound is low, and it is presumed that the quantum efficiency is excellent even when a photoelectric conversion film is formed at high speed.
  • the specific compound must have an ionization potential of -5.0 to -6.0 eV in a single film in terms of stability when used as a p-type organic semiconductor and energy level matching with an n-type organic semiconductor. is preferred.
  • the maximum absorption wavelength of the specific compound is preferably in the range of 500 to 700 nm, and more preferably in the range of 500 to 600 nm.
  • the maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) by adjusting the absorption spectrum of the specific compound to a concentration such that the absorbance is 0.5 to 1.0.
  • solvent chloroform
  • the specific compound is evaporated and the value measured using the specific compound in a film state is regarded as the maximum absorption wavelength of the specific compound.
  • the specific compound is particularly useful as a material for a photoelectric conversion film used in an image sensor, an optical sensor, or a photovoltaic cell.
  • the specific compound often functions as a dye within 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.
  • Examples of the specific compound include the following compounds.
  • R in the specific compound exemplified above represents any of the following groups. * represents the bonding position.
  • a specific compound may be purified if necessary.
  • purification methods for specific compounds include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, reslurry washing, reprecipitation purification, and purification using adsorbents such as activated carbon. Examples include recrystallization purification.
  • the specific compounds may be used alone or in combination of two or more. When two or more types are used, it is preferable that the total amount thereof falls within the following range.
  • the photoelectric conversion film preferably contains an n-type organic semiconductor in addition to the specific compound.
  • the n-type organic semiconductor is a compound different from the above specific compound.
  • An n-type organic semiconductor is an acceptor organic semiconductor material (compound) that is an organic compound that has the property of easily accepting electrons.
  • an n-type organic semiconductor is an 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 that has electron accepting properties can be used as an acceptor organic semiconductor.
  • n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof; condensed aromatic carbon ring compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, and fluoranthene derivatives); 5- to 7-membered heterocyclic compounds having at least one selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyridine ...
  • condensed aromatic carbon ring compounds e.g.,
  • Examples of the compounds include 1,4,5,8-naphthalenetetracarboxylic anhydride, 1,4,5,8-naphthalenetetracarboxylic anhydride imide derivatives and oxadiazole 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, and the compounds described in paragraphs [0056] to [0057] of JP2006-100767A.
  • fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred.
  • the fullerene include fullerene C60, fullerene C70, fullerene C76, fullerene C78, fullerene C80, fullerene C82, fullerene C84, fullerene C90, fullerene C96, fullerene C240, fullerene C540, and mixed fullerene.
  • fullerene derivatives include compounds obtained by adding a substituent to the above fullerene.
  • the above substituent is preferably an alkyl group, an aryl group or a heterocyclic group.
  • the fullerene derivative compounds described in JP-A No. 2007-123707 are preferred.
  • the n-type organic semiconductor may be an organic dye.
  • organic dyes 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, Examples include acridine dyes,
  • the molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.
  • the maximum absorption wavelength of the n-type organic semiconductor is preferably a wavelength of 400 nm or less or a wavelength range of 500 to 600 nm.
  • the photoelectric conversion film has a bulk heterostructure formed in a state in which a specific compound and an n-type organic semiconductor are mixed.
  • the bulk heterostructure is a layer in which a specific compound and an n-type organic semiconductor are mixed and dispersed within the photoelectric conversion film.
  • a photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. Note that the bulk heterostructure is explained in detail in paragraphs [0013] to [0014] of JP-A No. 2005-303266.
  • the difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.
  • the n-type organic semiconductors may be used alone or in combination of two or more.
  • the content of the n-type organic semiconductor in the photoelectric conversion film is 15 It is preferably 75% by volume, more preferably 20-60% by volume, even more preferably 20-50% by volume.
  • the content of fullerenes relative to the total content of the n-type organic semiconductor material is preferably 50 to 100% by volume, more preferably 80 to 100% by volume.
  • Fullerenes may be used alone or in combination of two or more.
  • the content of the specific compound relative to the total content of the specific compound and the n-type organic semiconductor is preferably 20 to 80% by volume, more preferably 30 to 80% by volume.
  • the content of the specific compound is preferably 15 to 75% by volume, more preferably 20 to 75% by volume.
  • the photoelectric conversion film is substantially composed of a specific compound, an n-type organic semiconductor, and a p-type organic semiconductor 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 volume%, preferably 95 to 100 volume%, and 99 to 100 volume%, with respect to the total mass of the photoelectric conversion film. More preferably 100% by volume.
  • the photoelectric conversion film contains a p-type organic semiconductor in addition to the above-mentioned specific compound.
  • the p-type organic semiconductor is a compound different from the above-mentioned specific compound.
  • a 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. That is, a p-type organic semiconductor refers to an organic compound that has a smaller ionization potential when two organic compounds are used in contact with each other.
  • the p-type organic semiconductors may be used alone or in combination of two or more.
  • Examples of p-type organic semiconductors include triarylamine compounds (for example, N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl ( ⁇ -NPD), compound described in paragraphs [0128] to [0148] of JP 2011-228614, JP 2011-176259 Compounds described in paragraphs [0052] to [0063] of Japanese Patent Publication No. 2011-225544, compounds described in paragraphs [0119] to [0158] of Japanese Patent Application Publication No.
  • TPD N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
  • ⁇ -NPD 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl
  • Examples of the p-type organic semiconductor include compounds having a smaller ionization potential than the n-type organic semiconductor, and if this condition is satisfied, the organic dyes exemplified as the n-type organic semiconductor can be used. Examples of compounds that can be used as p-type organic semiconductors are shown below.
  • the difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.
  • the p-type organic semiconductors may be used alone or in combination of two or more.
  • the content of the p-type organic semiconductor in the photoelectric conversion film is 15 It is preferably 75% by volume, more preferably 20-60% by volume, even more preferably 20-50% by volume.
  • a photoelectric conversion film containing a specific compound is a non-luminescent film and has characteristics different from organic light emitting diodes (OLEDs).
  • a non-luminescent film means a film with 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.
  • the photoelectric conversion film contains a dye in addition to the above-mentioned specific compound.
  • the dye is a compound different from the above specific compound.
  • organic dyes are preferred. Examples of organic dyes 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
  • the maximum absorption wavelength of the dye is preferably in the visible light region, more preferably 400 to 600 nm, and even more preferably 400 to 500 nm.
  • the dyes may be used alone or in combination of two or more.
  • the photoelectric conversion film may be formed, for example, by a dry film formation method.
  • the dry film formation method include physical vapor deposition methods such as vapor deposition (particularly vacuum deposition), sputtering, ion plating, and MBE (Molecular Beam Epitaxy), and CVD (Chemical Vapor Deposition) methods such as plasma polymerization, and the vacuum deposition method is preferred.
  • the manufacturing conditions such as the degree of vacuum and the deposition temperature can be set according to a conventional method.
  • the thickness of the photoelectric conversion film is preferably 10 to 1000 nm, more preferably 50 to 800 nm, and even more preferably 50 to 500 nm.
  • the photoelectric conversion element has an electrode.
  • the electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Electrically conductive materials include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident from the upper electrode 15, it is preferable that the upper electrode 15 is transparent to the light to be detected. Examples of the material constituting the upper electrode 15 include antimony tin oxide (ATO), fluorine doped tin oxide (FTO), tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO).
  • ATO antimony tin oxide
  • FTO fluorine doped tin oxide
  • ITO indium tin oxide
  • Conductive metal oxides such as Indium Tin Oxide (Indium Tin Oxide) and Indium Zinc Oxide (IZO); Metal thin films such as gold, silver, chromium, and nickel; Mixtures or laminations of these metals and conductive metal oxides.
  • organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and nanocarbon materials such as carbon nanotubes and graphene; and conductive metal oxides are preferred in terms of high conductivity and transparency.
  • the sheet resistance may be 100 to 10,000 ⁇ / ⁇ , and there is a large degree of freedom in the range of film thickness that can be made thin.
  • An increase in light transmittance is preferable because it increases light absorption in the photoelectric conversion film and increases photoelectric conversion ability.
  • the thickness of the upper electrode 15 is preferably 5 to 100 nm, more preferably 5 to 20 nm.
  • the lower electrode 11 may be transparent or may not be transparent and may reflect light.
  • the material constituting the lower electrode 11 include tin oxide doped with antimony or fluorine (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • conductive metal oxides such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN), etc.); Mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; carbon materials such as carbon nanotubes and granphene.
  • the method for forming the electrode can be selected as appropriate depending on the electrode material. Specifically, wet methods such as printing methods and coating methods; physical methods such as vacuum evaporation methods, sputtering methods and ion plating methods; and chemical methods such as CVD and plasma CVD methods can be mentioned.
  • wet methods such as printing methods and coating methods
  • physical methods such as vacuum evaporation methods, sputtering methods and ion plating methods
  • chemical methods such as CVD and plasma CVD methods
  • CVD and plasma CVD methods can be mentioned.
  • the material of the electrode is ITO, methods such as electron beam method, sputtering method, resistance heating vapor deposition method, chemical reaction method (sol-gel method, etc.), and coating of indium tin oxide dispersion can be used.
  • 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.
  • the intermediate layer include a charge blocking film.
  • the charge blocking film include an electron blocking film and a hole blocking film.
  • the electron blocking film is a donor organic semiconductor material (compound), and the above p-type organic semiconductor can be used. Additionally, polymeric materials can also be used as the electron blocking film. Examples of the polymeric material include polymers such as phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, and derivatives thereof.
  • the electron blocking film may be composed of multiple films.
  • the electron blocking film may be composed of an inorganic material.
  • inorganic materials have a higher dielectric constant than organic materials, so when an inorganic material is used for an electron blocking film, more voltage is applied to the photoelectric conversion film, resulting in higher quantum efficiency.
  • Inorganic materials that can be used as electron blocking films include, for example, calcium oxide, chromium oxide, copper chromium oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, copper gallium oxide, copper strontium oxide, niobium oxide, molybdenum oxide, and indium oxide. Copper, indium silver oxide and iridium oxide may be mentioned.
  • the hole blocking film is an acceptor organic semiconductor material (compound), and the above n-type organic semiconductor can be used.
  • the hole blocking film may be composed of multiple films.
  • Methods for manufacturing the charge blocking film include, for example, a dry film formation method and a wet film formation method.
  • dry film formation methods include a vapor deposition method and a sputtering method.
  • the vapor deposition method may be either a physical vapor deposition (PVD) method or a chemical vapor deposition (CVD) method, with physical vapor deposition methods such as vacuum vapor deposition being preferred.
  • wet film formation methods include an inkjet method, a spray method, a nozzle print method, a spin coat method, a dip coat method, a cast method, a die coat method, a roll coat method, a bar coat method, and a gravure coat method, with the inkjet method being preferred in terms of high-precision patterning.
  • each charge blocking film is preferably 3 to 200 nm, more preferably 5 to 100 nm, and even more preferably 5 to 30 nm.
  • the photoelectric conversion element may further include a substrate.
  • the substrate include a semiconductor substrate, a glass substrate, and a plastic substrate. Note that the position of the substrate is such that a conductive film, a photoelectric conversion film, and a transparent conductive film are usually laminated in this order on the substrate.
  • the photoelectric conversion element may further include a sealing layer.
  • the performance of photoelectric conversion materials may be significantly deteriorated in the presence of deterioration factors such as water molecules, etc. Therefore, the deterioration can be prevented by covering and sealing the entire photoelectric conversion film with a sealing layer such as ceramics such as dense metal oxide, metal nitride, or metal nitride oxide, which does not allow water molecules to penetrate, or diamond-like carbon (DLC).
  • a sealing layer such as ceramics such as dense metal oxide, metal nitride, or metal nitride oxide, which does not allow water molecules to penetrate, or diamond-like carbon (DLC).
  • the sealing layer is described, for example, in paragraphs [0210] to [0215] of JP-A-2011-082508, the contents of which are incorporated herein by reference.
  • An example of a use of a photoelectric conversion element is an image sensor.
  • An image sensor is an element that converts optical information of an image into an electrical signal.
  • multiple photoelectric conversion elements are arranged on the same plane in a matrix, and each photoelectric conversion element (pixel) converts an optical signal into an electrical signal.
  • pixel converts an optical signal into an electrical signal.
  • each pixel is composed of one or more photoelectric conversion elements and one or more transistors.
  • the photoelectric conversion element of the present invention is preferably used as an optical sensor.
  • the above photoelectric conversion element may be used alone, or may be used as a line sensor in which the above photoelectric conversion elements are arranged in a straight line, or as a two-dimensional sensor in which the above photoelectric conversion elements are arranged on a plane.
  • the present invention also includes inventions of compounds.
  • the compound of the present invention is the above-mentioned specific compound.
  • a photoelectric conversion element having the form shown in FIG. 2 was produced using the evaluation compound (specific compound or comparative compound).
  • the photoelectric conversion element includes a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15.
  • amorphous ITO is formed into a film by sputtering on a glass substrate to form a lower electrode 11 (thickness: 30 nm), and the following compound (EB-1) is further heated in vacuum on the lower electrode 11.
  • a film was formed by vapor deposition to form an electron blocking film 16A (thickness: 30 nm).
  • each material shown in Table 1 evaluation compound, p-type organic semiconductor and n-type organic semiconductor (fullerene (C 60 )) was deposited on the electron blocking film 16A at the ratio (volume ratio) shown in Table 1.
  • a photoelectric conversion film 12 having a bulk heterostructure was formed.
  • the following compound (EB-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm).
  • Hole blocking Amorphous ITO was deposited on the film 16B by sputtering to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm).
  • SiO was deposited as a sealing layer on the upper electrode 15 by vacuum evaporation.
  • an aluminum oxide (Al 2 O 3 ) layer was formed thereon by the ALCVD (Atomic Layer Chemical Vapor Deposition) method. Then, the film was heated at 150° C. for 30 minutes in a glove box under a nitrogen atmosphere. , a photoelectric conversion element was fabricated. Note that in Examples and Comparative Examples other than Comparative Examples 1-3, photoelectric conversion films could be formed by vapor deposition. In other words, it was confirmed that the evaluation compounds used in Examples and Comparative Examples other than Comparative Examples 1-3 were excellent in vapor deposition suitability. Further, in Comparative Example 1-3, a photoelectric conversion film could not be formed by vapor deposition, and a photoelectric conversion element could not be obtained.
  • the dark current of each of the obtained photoelectric conversion elements was measured by the following method. A voltage was applied to the lower electrode and the upper electrode of each photoelectric conversion element so that the electric field strength was 2.5 ⁇ 10 5 V/cm, and the current value in the dark (dark current) was measured. As a result, it was confirmed that the dark current of each photoelectric conversion element was 50 nA/cm 2 or less, indicating a sufficiently low dark current.
  • Quantum efficiency The quantum efficiency of each of the obtained photoelectric conversion elements was measured by the following method. After applying a voltage to each photoelectric conversion element to have an electric field strength of 2.0 ⁇ 10 5 V/cm, light is irradiated from the upper electrode (transparent conductive film) side to increase the quantum efficiency (photoelectric conversion) at a wavelength of 600 nm. efficiency) was evaluated, and the quantum efficiency was determined according to equation (S1).
  • Quantum efficiency (relative ratio) (Quantum efficiency at a wavelength of 600 nm of each photoelectric conversion element of Example or Comparative Example) / (Quantum efficiency at a wavelength of 600 nm of the photoelectric conversion element of Example 1-1)
  • the response speed of each of the obtained photoelectric conversion elements was evaluated by the following method.
  • a voltage was applied to the photoelectric conversion element at an intensity of 2.0 ⁇ 10 5 V/cm.
  • an LED light emitting diode
  • the photocurrent is 97% from 0% signal intensity.
  • the rise time until the signal intensity rose to % was measured, and the relative response speed was evaluated according to equation (S2).
  • Relative response speed (Rise time at wavelength 600 nm of each photoelectric conversion element of Example or Comparative Example) / (Rise time at wavelength 600 nm of photoelectric conversion element of Example 1-1)
  • Table 1 shows the evaluation results of test X.
  • R 3 when R 3 represents a group represented by formula (R-1) or a group represented by formula (R-2), it is marked as “A”, and otherwise it is marked as “B”.
  • Ar 1 Ar 2 when Ar 1 and Ar 2 each represent a monocyclic aromatic ring group, it is marked as "A”, and otherwise it is marked as "B”.
  • Forma (2) if the specific compound corresponds to the compound represented by formula (2), it is marked with "A”, and if not, it is marked with "B”.
  • the photoelectric conversion element of the present invention is excellent in vapor deposition manufacturing suitability, quantum efficiency when receiving red-green light, and electric field strength dependence of response speed.
  • R 3 is a group represented by formula (R-1) or a group represented by formula (R-2) (Examples 1-1 and 1 -3 to 1-9, 1-10 and 1-14). It was confirmed that the effects of the present invention were more excellent when Ar 1 and Ar 2 were monocyclic aromatic ring groups (Examples 1-1, 1-12, and 1-15). It was confirmed that the effects of the present invention were more excellent when the specific compound contained the compound represented by formula (2) (Examples 1-1, 1-13, and 1-16). It was confirmed that the effects of the present invention were more excellent when the specific compound contained the compound represented by formula (3) (Examples 1-1, 1-11, and 1-14 to 1-16).
  • Quantum efficiency The quantum efficiency of each of the obtained photoelectric conversion elements was measured by the following method. After applying a voltage to each photoelectric conversion element to have an electric field strength of 2.0 ⁇ 10 5 V/cm, light is irradiated from the upper electrode (transparent conductive film) side to determine the quantum efficiency at a wavelength of 460 nm or 600 nm. (Photoelectric conversion efficiency) was evaluated, and quantum efficiency was determined according to formula (S4).
  • Quantum efficiency (relative ratio) (Quantum efficiency at wavelength 460 nm or wavelength 600 nm of each photoelectric conversion element of Example or Comparative Example) / (Quantum efficiency at wavelength 460 nm or wavelength 600 nm of photoelectric conversion element of Example 2-1) quantum efficiency)
  • Quantum efficiency is less than 0.60
  • Relative response speed (rise time of each photoelectric conversion element of Example or Comparative Example at wavelength 460 nm or wavelength 600 nm)/(rise time of photoelectric conversion element of Example 2-1 at wavelength 460 nm or wavelength 600 nm) )
  • Table 2 shows the evaluation results of Test Y.
  • R 3 represents a group represented by formula (R-1) or a group represented by formula (R-2), it is marked as “A”, and in other cases, it is marked as "B". And so.
  • Ar 1 Ar 2 the case where Ar 1 and Ar 2 represent a monocyclic aromatic ring group was designated as "A”, and the other cases were designated as "B".
  • the “Formula (2)” column cases where the specific compound corresponds to the compound represented by Formula (2) are marked as "A”, and other cases are marked as "B”.
  • Formula (3) cases where the specific compound corresponds to the compound represented by Formula (3) are marked as "A", and other cases are marked as "B".
  • the ratio (volume ratio) indicates the component ratio of evaluation compound: dye: p-type organic semiconductor: n-type organic semiconductor in order from the left.

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Abstract

La présente invention aborde le problème de la fourniture d'un dispositif de conversion photoélectrique, d'un dispositif d'imagerie, d'un photocapteur et d'un composé qui sont excellents en ce qui concerne l'applicabilité de la production de dépôt en phase vapeur, la dépendance à l'intensité électromagnétique de l'efficacité quantique et la vitesse de réponse lorsqu'une lumière rouge/verte a été reçue. Cet élément de conversion photoélectrique comprend un film conducteur, un film de conversion photoélectrique et un film conducteur transparent, dans cet ordre, et le film de conversion photoélectrique comprend un composé représenté par la formule (1).
PCT/JP2023/031478 2022-09-20 2023-08-30 Dispositif de conversion photoélectrique, dispositif d'imagerie, photocapteur et composé Ceased WO2024062871A1 (fr)

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WO2013042414A1 (fr) * 2011-09-22 2013-03-28 日本電気株式会社 Composé de dithiénopyrrole, colorant pour élément de conversion photoélectrique, électrode de semi-conducteur l'utilisant pour un élément de conversion photoélectrique et élément de conversion photoélectrique
JP2013530978A (ja) * 2010-06-24 2013-08-01 ヘリアテク・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 蒸発性有機半導体材料および光電子構成部品におけるその使用
US20200328357A1 (en) * 2019-02-15 2020-10-15 The Regents Of The University Of California Organic solar cell and photodetector materials and devices
JP2022030124A (ja) * 2020-08-06 2022-02-18 三菱ケミカル株式会社 有機半導体デバイス、有機半導体インク及びフォトディテクタ
CN114195801A (zh) * 2021-12-07 2022-03-18 电子科技大学 基于3-烷氧基-4-氰基噻吩的近红外有机光电分子材料
WO2022091799A1 (fr) * 2020-10-30 2022-05-05 富士フイルム株式会社 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé

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KR20170108068A (ko) 2015-01-27 2017-09-26 소니 주식회사 유기 포토다이오드에서 유기 광전 변환 층을 위한 물질로서의 스쿠아레인계 분자

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JP2013530978A (ja) * 2010-06-24 2013-08-01 ヘリアテク・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 蒸発性有機半導体材料および光電子構成部品におけるその使用
WO2013042414A1 (fr) * 2011-09-22 2013-03-28 日本電気株式会社 Composé de dithiénopyrrole, colorant pour élément de conversion photoélectrique, électrode de semi-conducteur l'utilisant pour un élément de conversion photoélectrique et élément de conversion photoélectrique
US20200328357A1 (en) * 2019-02-15 2020-10-15 The Regents Of The University Of California Organic solar cell and photodetector materials and devices
JP2022030124A (ja) * 2020-08-06 2022-02-18 三菱ケミカル株式会社 有機半導体デバイス、有機半導体インク及びフォトディテクタ
WO2022091799A1 (fr) * 2020-10-30 2022-05-05 富士フイルム株式会社 Élément de conversion photoélectrique, élément d'imagerie, capteur optique et composé
CN114195801A (zh) * 2021-12-07 2022-03-18 电子科技大学 基于3-烷氧基-4-氰基噻吩的近红外有机光电分子材料

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