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  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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  • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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  • H10K85/649—Aromatic compounds comprising a hetero atom
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  • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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  • Y02E10/549—Organic PV cells

Definitions

• the present invention relates to a photoelectric conversion element, an imaging element, an optical sensor, a method for manufacturing an imaging element, and a compound.
• Patent Document 1 and Non-Patent Document 1 disclose dye compounds with specific structures that can be used as dyes for dye-sensitized solar cells.
• the characteristics required for photoelectric conversion elements include an excellent response speed when receiving green and red light.
• the response speed of the photoelectric conversion element does not decrease easily even when the electric field strength is changed, that is, the response speed has a small electric field strength dependency.
• the present inventors have produced and investigated a photoelectric conversion element containing the compound disclosed in Patent Document 1, and have found that there is a need to improve the response speed when green and red light is received and the dependency of the response speed on the electric field strength.
• the green and red light means light having a wavelength of 500 to 650 nm.
• X2 represents an oxygen atom or a sulfur atom.
• X 4 represents a sulfur atom.
• X 1 represents -C(R c1 R c2 )-;
• the photoelectric conversion element according to any one of [1] to [3], wherein in the above formula (2), X 3 represents —C(R c11 R c12 )—.
• R c1 and R c2 do not bond to each other to form a ring which may have a substituent, and R c11 and R c12 do not bond to each other to form a ring which may have a substituent.
• Xc1 and Xc2 represent oxygen atoms;
• the photoelectric conversion film further contains an n-type organic semiconductor, The photoelectric conversion element according to any one of [1] to [8], wherein the photoelectric conversion film has a bulk heterostructure formed in a state in which the compound represented by the formula (1) and the n-type organic semiconductor are mixed.
• An optical sensor comprising the photoelectric conversion element according to any one of [1] to [13].
• a method for producing an imaging element comprising the step of producing the photoelectric conversion element according to any one of [1] to [13].
• [17] A compound represented by the following formula (1) or the following formula (2).
• [18] The compound according to [17], wherein in the above formula (1), X2 represents an oxygen atom or a sulfur atom.
• X 4 represents a sulfur atom.
• X 1 represents -C(R c1 R c2 )-;
• X 3 represents —C(R c11 R c12 )—.
• R c1 and R c2 do not bond to each other to form a ring which may have a substituent, and R c11 and R c12 do not bond to each other to form a ring which may have a substituent.
• R c1 and R c2 are different groups, R c3 and R c4 are different groups, R c5 and R c6 are different groups, and R c7 and R c8 are different groups;
• R c11 and R c12 are different groups, R c13 and R c14 are different groups, R c15 and R c16 are different groups, and R c17 and R c18 are different groups.
• the present invention it is possible to provide a photoelectric conversion element which has an excellent response speed when receiving green and red light and in which the response speed has a small dependency on the electric field strength. Furthermore, according to the present invention, there can be provided an imaging element, an optical sensor, a method for manufacturing an imaging element, and a compound related to the above-mentioned photoelectric conversion element.
• FIG. 2 is a schematic cross-sectional view showing a configuration example of a photoelectric conversion element.
• FIG. 2 is a schematic cross-sectional view showing a 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 the lower and upper limits.
• the hydrogen atom may be either a protium atom (normal hydrogen atom) or a deuterium atom (for example, a deuterium atom, etc.).
• substituents, linking groups, etc. hereinafter also referred to as "substituents, etc." represented by specific symbols, or when a plurality of substituents, etc. are simultaneously specified, 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.
• substituent W in this specification will be described.
• substituent W include a halogen atom (e.g., 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,
• a halogen atom
• each of the above groups may further have a substituent (e.g., one or more groups among the above groups, etc.) if possible.
• a substituent e.g., one or more groups among the above groups, etc.
• an alkyl group that 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 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 compound described later does not have 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 a primary amino group as a substituent.
• halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
• the aliphatic hydrocarbon group may be any of linear, branched, and cyclic.
• the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group.
• the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms.
• the alkyl group may be linear, branched, or cyclic.
• alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, a cyclopropyl group, and a cyclopentyl group.
• the alkyl group may be any one of a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group, and may have these ring structures as partial structures.
• examples of the substituent which the alkyl group may have examples of the substituent which the alkyl group may have include the groups exemplified by the substituent W.
• an aryl group preferably having 6 to 18 carbon atoms, more preferably having 6 carbon atoms
• a heteroaryl group preferably having 5 to 18 carbon atoms, more preferably having 5 to 6 carbon atoms
• a halogen atom preferably a fluorine atom or a chlorine atom
• the alkyl group moiety in the alkoxy group is preferably the above-mentioned alkyl group
• the alkyl group moiety in the alkylthio group is preferably the above-mentioned alkyl group.
• examples of the substituent which the alkoxy group may have include the same substituents as those in the alkyl group which may have a substituent.
• examples of the substituent which the alkylthio group may have include the same substituents as those in the alkyl group which may have a substituent.
• the alkenyl group may be any of linear, branched, and cyclic.
• the number of carbon atoms in the alkenyl group is preferably 2 to 20.
• examples of the substituent which the alkenyl group may have include the same as those of the substituent in the alkyl group which may have a substituent.
• the alkynyl group may be any of linear, branched, and cyclic.
• the number of carbon atoms in the alkynyl group is preferably 2 to 20.
• 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 atoms.
• 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.
• Examples of the aromatic heterocycle include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring (e.g., a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring), a tetrazine ring (e.g., 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
• thienothiazole ring for example, thieno[2,3-d]thiazole ring, etc.
• benzothiadiazole ring benzodithiophene ring (for example, benzo[1,2-b:4,5-b']dithiophene ring, etc.), thienothiophene ring (for example, thieno[3,2-b]thiophene ring, etc.), thiazolothiazole ring (for example, thiazolo[5,4-d]thiazole ring, etc.), naphthodithiophene ring (for example, naphtho[2,3 [2,1-b:6,7-b']dithiophene ring, naphtho[2,1-b:6,5-b']dithiophene ring, naphtho[1,2-b:5,6-b']dithiophene ring, 1,8-dithiadicyclopenta[
• 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 in which one hydrogen atom has been removed 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.).
• non-aromatic ring refers to a ring structure that is not aromatic, and examples thereof include an aliphatic hydrocarbon ring and an aliphatic heterocycle.
• the aliphatic hydrocarbon ring include cycloalkanes, cycloalkenes, and cycloalkynes.
• the number of heteroatoms contained as ring member atoms in the aliphatic heterocycle 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.
• aliphatic heterocycle examples include a pyrrolidine ring, an oxolane ring, a thiolane ring, a piperidine ring, a tetrahydropyran ring, a thiane ring, a piperazine ring, a morpholine ring, a quinuclidine ring, an azetidine ring, an oxetane ring, an aziridine ring, a dioxane ring, and ⁇ -butyrolactone.
• the term "aliphatic hydrocarbon ring group” includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aliphatic hydrocarbon ring.
• aliphatic heterocyclic group includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aliphatic heterocycle.
• a formula showing a chemical structure contains a plurality of identical symbols showing the type or number of groups, unless otherwise specified, 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, unless otherwise specified, and the specific contents of the groups of the same type may be the same or different.
• the bond direction of the divalent group is not limited unless otherwise specified.
• the compound may be either "X-O-CO-Z" or "X-CO-O-Z”.
• 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.
• 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) or a compound represented by formula (2) (hereinafter also referred to as a "specific compound").
• the mechanism by which the effects are obtained is not limited by the following speculation. In other words, even if the effects are obtained by a mechanism other than the following, it is included in the scope of the present invention.
• the specific compound is a so-called ADA type dye compound having a donor portion (D) and an acceptor portion (A).
• the ADA type dye compound tends to have high aggregation due to its conjugated structure and polar structure.
• the specific compound has a specific condensed ring structure containing a specific atom as represented by formula (1) and formula (2), thereby suppressing excessive aggregation between the specific compounds in the photoelectric conversion film, and efficient charge separation can be achieved.
• the photoelectric conversion element containing the specific compound is considered to have excellent response speed and small electric field strength dependency of the response speed.
• achieving at least one of a better response speed and a smaller dependency of the response speed on the electric field strength is also referred to as "the effect of the present invention being better.”
• FIG. 1 is a schematic cross-sectional view of one embodiment of a photoelectric conversion element of the present invention.
• the photoelectric conversion element 10a shown in Figure 1 has a configuration in which a conductive film (hereinafter also referred to as the "lower electrode") 11 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 a configuration example of another photoelectric conversion element.
• 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 laminated in this order on a lower electrode 11.
• the laminated 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 10 a it is preferable that light is incident on the photoelectric conversion film 12 through the upper electrode 15 . Furthermore, 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 it is preferable to apply a voltage of 1 ⁇ 10 ⁇ 5 to 1 ⁇ 10 7 V/cm 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.
• the voltage is preferably applied so that the electron blocking film 16A side becomes the cathode and the photoelectric conversion film 12 side becomes the anode.
• the photoelectric conversion element 10a (or 10b) is used as an optical sensor or incorporated in an imaging element, a voltage can be applied in a similar manner.
• 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.
• the photoelectric conversion element has a photoelectric conversion film.
• the photoelectric conversion film contains a specific compound which is a compound represented by formula (1) or formula (2).
• the specific compound is preferably a compound represented by formula (1) in that the effect of the present invention is more excellent.
• R 1 and R 2 each independently represent a hydrogen atom or a substituent.
• X1 represents -C( Rc1Rc2 ) -, -O-C( Rc3Rc4 )-, -Si( Rc5Rc6 )-, or -Ge( Rc7Rc8 )-.
• Rc1, Rc2 , Rc3 , Rc4 , Rc5 , Rc6 , Rc7 , and Rc8 each independently represent a hydrogen atom or a substituent.
• Rc1 and Rc2 , Rc3 and Rc4 , Rc5 and Rc6 , and Rc7 and Rc8 may each be bonded to each other to form a ring which may have a substituent.
• X2 represents an oxygen atom, a sulfur atom, or -NR N1 -, where R N1 represents a hydrogen atom or a substituent.
• A1 and A2 each independently represent a group represented by formula (A-1).
• R3 and R4 each independently represent a hydrogen atom or a substituent.
• R N2 represents a hydrogen atom or a substituent.
• X3 represents -C( Rc11Rc12 ) -, -O-C( Rc13Rc14 )-, -Si( Rc15Rc16 )-, or -Ge( Rc17Rc18 )-.
• Rc11 , Rc12 , Rc13 , Rc14 , Rc15 , Rc16 , Rc17 , and Rc18 each independently represent a hydrogen atom or a substituent.
• Rc11 and Rc12 , Rc13 and Rc14 , Rc15 and Rc16, and Rc17 and Rc18 may each be bonded to each other to form a ring which may have a substituent.
• X4 represents a sulfur atom or -NR N3 -, where R N3 represents a hydrogen atom or a substituent.
• A3 and A4 each independently represent a group represented by formula (A-1).
• * represents a bonding position.
• C1 represents a ring containing 2 or more carbon atoms which may have a substituent.
• R W2 represents a hydrogen atom or a substituent.
• R W3 and R W4 each independently represent a cyano group, -SO 2 R W5 , -COOR W6 or -COR W7 .
• R W5 to R W7 each independently represent 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.
• R 1 and R 2 each independently represent a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above.
• R 1 and R 2 are preferably hydrogen atoms.
• X1 represents -C( Rc1Rc2 )-, -O - C (Rc3Rc4 ) - , -Si ( Rc5Rc6 )-, or -Ge( Rc7Rc8 )-.
• X 1 is preferably —C(R c1 R c2 )— or —Si(R c5 R c6 )—, and more preferably —C(R c1 R c2 )—.
• R c1 , R c2 , R c3 , R c4 , R c5 , R c6 , R c7 , and R c8 each independently represent a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above.
• substituents include an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an amino group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, a silyl group, a cyano group, or a halogen atom.
• the above-mentioned substituent is also preferably a substituent represented by Rs described below.
• substituents that may be possessed by each of the above groups that may have a substituent include the substituents exemplified as the substituent W described above, and the substituents selected from the substituent group S described below are preferred.
• the alkyl group may be linear, branched, or cyclic.
• the cyclic alkyl group may be either a monocyclic or polycyclic group, i.e., a cycloalkyl group, a bicycloalkyl group, a tricycloalkyl group, or the like.
• the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 5 carbon atoms.
• the linear alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably 1 or 2 carbon atoms.
• the branched alkyl group preferably has 3 to 5 carbon atoms, more preferably 3 to 4 carbon atoms, and even more preferably 3 carbon atoms.
• the cyclic alkyl group preferably has 3 to 6 carbon atoms, and more preferably has 3 to 5 carbon atoms.
• the alkenyl group and alkynyl group may be straight-chain, branched-chain, or cyclic.
• the cyclic alkenyl and alkynyl groups may be either monocyclic or polycyclic, for example, a cycloalkenyl group or a bicycloalkenyl group.
• the alkenyl group and alkynyl group preferably have 2 to 21 carbon atoms, more preferably 2 to 11 carbon atoms, further preferably 2 to 6 carbon atoms, and particularly preferably 2 to 5 carbon atoms.
• the aryl group and heteroaryl group may be either a monocyclic or polycyclic group, and is preferably a monocyclic group.
• the aryl group preferably has 5 to 18 carbon atoms, more preferably 6 to 10 carbon atoms, and even more preferably 6 to 8 carbon atoms.
• the definition and specific examples of the aryl group are as described above, and a phenyl group or naphthyl group is preferable, and a phenyl group is more preferable.
• the heteroaryl group preferably has 5 to 18 ring atoms, more preferably 5 to 10 ring atoms, and even more preferably 5 to 8 ring atoms.
• heteroatom contained in the heteroaryl group examples 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, and a sulfur atom, an oxygen atom, or a nitrogen atom is preferable.
• the definition and specific examples of the heteroaryl group are as described above, and a thiophene ring group, a furan ring group, or a pyridine ring group is preferable.
• the aryl and heteroaryl groups may have a substituent as described above. When the aryl and heteroaryl groups have a substituent, the number of the substituents is not particularly limited, but is preferably 1 to 3.
• the alkoxy group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 5 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
• Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, a t-butoxy group, and a cyclopropoxy group.
• the aryl group contained in the aryloxy group may be either a monocyclic or polycyclic ring.
• the aryloxy group preferably has 5 to 18 carbon atoms, more preferably 6 to 10 carbon atoms, and even more preferably 6 to 8 carbon atoms.
• the aryloxy group includes, for example, a phenoxy group.
• the amino group may be any of a primary amino group, a secondary amino group, and a tertiary amino group.
• the substituent on the nitrogen atom is preferably a hydrocarbon group, more preferably an alkyl group (preferably having 1 to 5 carbon atoms) or an aryl group.
• the aliphatic heterocyclic group may be either a monocyclic or polycyclic group, and is preferably a monocyclic group.
• the aliphatic heterocyclic group preferably has 3 to 18 ring atoms, more preferably 5 to 10 ring atoms, and even more preferably 5 to 8 ring atoms.
• Examples of the heteroatom of 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, and a sulfur atom, an oxygen atom, or a nitrogen atom is preferable.
• aliphatic heterocyclic group examples include as described above, and a thiolane ring group, a piperidine ring group, a tetrahydrofuran ring group, or a tetrahydropyran ring group is preferred.
• the aliphatic heterocyclic group may have a substituent as described above.
• the number of the substituents is not particularly limited, but is preferably 1 to 3.
• the hydrocarbon group contained in the acyl group may be any one of an alkyl group, an alkenyl group, an alkynyl group, and an aryl group, preferably an alkyl group or an aryl group, and more preferably an alkyl group.
• the acyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 or 2 carbon atoms.
• acyl group examples include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a hexanoyl group, and a benzoyl group, with the acetyl group being preferred.
• the silyl group is a group represented by -Si(R Si ) 3.
• Each R Si independently represents an alkyl group, an alkenyl group, an alkynyl group, or an aryl group.
• the definitions and preferred embodiments of the alkyl group, alkenyl group, alkynyl group, and aryl group represented by R Si are the same as those of the alkyl group, alkenyl group , alkynyl group, and aryl group exemplified as the substituents represented by R c1 , R c2 , R c3 , R c4, R c5 , R c6 , R c7 , and R c8 .
• halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms and chlorine atoms being preferred.
• R c1 and R c2 , R c3 and R c4 , R c5 and R c6 , and R c7 and R c8 may be bonded to each other to form a ring which may have a substituent. However, in terms of the effects of the present invention being more excellent, it is also preferable that they do not form a ring.
• the ring may be either an aromatic ring or a non-aromatic ring, and may be either a monocyclic ring or a polycyclic ring.
• the ring may have a heteroatom, such as a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, or a boron atom, and is preferably a sulfur atom, a nitrogen atom, or an oxygen atom.
• the ring preferably has 3 to 20 member atoms, more preferably 5 to 12 member atoms, and even more preferably 5 to 8 member atoms. Examples of the substituent that the ring may have include the substituents exemplified for the substituent W described above, and a substituent selected from the substituent group S described below is preferred.
• R c1 and R c2 are different groups
• R c3 and R c4 are different groups
• R c5 and R c6 are different groups
• R c7 and R c8 are different groups.
• X 2 represents an oxygen atom, a sulfur atom, or —NR N1 —.
• X2 is preferably an oxygen atom or a sulfur atom.
• R N1 represents a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above. More specifically, examples of the substituent include an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, and a heteroaryl group which may have a substituent.
• R N1 is also preferably a substituent represented by Rt described below.
• each substituent represented by R N1 is the same as those of each group exemplified as the substituents represented by R c1 , R c2 , R c3 , R c4 , R c5 , R c6 , R c7 , and R c8 described above.
• a 1 and A 2 each independently represent a group represented by formula (A-1).
• Formula (A-1) will be described later.
• R3 and R4 each independently represent a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above.
• R3 and R4 are preferably hydrogen atoms.
• R N2 represents a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above. More specifically, examples of the substituent include an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, and a heteroaryl group which may have a substituent.
• R N2 is also preferably a group represented by Rt described below. The definition and preferred embodiments of the group represented by R N2 are the same as those of the group represented by R N1 in formula (1).
• X3 represents -C(Rc11Rc12 ) -, -O - C ( Rc13Rc14 )-, -Si( Rc15Rc16 )-, or -Ge( Rc17Rc18 )-.
• X 3 is preferably —C(R c11 R c12 )— or —Si(R c15 R c16 )—, and more preferably —C(R c11 R c12 )—.
• Rc11 , Rc12 , Rc13 , Rc14 , Rc15 , Rc16 , Rc17 , and Rc18 each independently represent a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above.
• substituents include an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an amino group which may have a substituent, an aliphatic heterocyclic group which may have a substituent, an acyl group which may have a substituent, a silyl group, a cyano group, or a halogen atom.
• the above-mentioned substituent is also preferably a substituent represented by Rs described below.
• Rc11, Rc12 , Rc13, Rc14 , Rc15 , Rc16 , Rc17, and Rc18 are the same as those of the groups represented by Rc1 , Rc2 , Rc3 , Rc4 , Rc5 , Rc6 , Rc7 , and Rc8 in formula ( 1 ) .
• R c11 and R c12 , R c13 and R c14 , R c15 and R c16 , and R c17 and R c18 may be bonded to each other to form a ring which may have a substituent, but in terms of the effects of the present invention being more excellent, it is also preferable that they do not form a ring.
• the ring may be either an aromatic ring or a non-aromatic ring, and may be either a monocyclic ring or a polycyclic ring.
• the ring may have a heteroatom, such as a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, or a boron atom, and is preferably a sulfur atom, a nitrogen atom, or an oxygen atom.
• the ring preferably has 3 to 20 member atoms, more preferably 5 to 12 member atoms, and even more preferably 5 to 8 member atoms. Examples of the substituent that the ring may have include the substituents exemplified for the substituent W described above, and a substituent selected from the substituent group S described below is preferred.
• R c11 and R c12 are different groups
• R c13 and R c14 are different groups
• R c15 and R c16 are different groups
• R c17 and R c18 are different groups.
• X 4 represents a sulfur atom or —NR N3 —. In terms of obtaining superior effects of the present invention, X4 is preferably a sulfur atom.
• R N3 represents a hydrogen atom or a substituent.
• substituents include the substituents exemplified for the substituent W described above. More specifically, examples of the substituent include an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent.
• R N3 is also preferably a group represented by Rt described below. The definition and preferred embodiments of the group represented by R N3 are the same as those of the group represented by R N1 in formula (1).
• X 1 represents -C(R c1 Rs)-, -O-C(R c3 Rs)-, -Si(R c5 Rs)-, or -Ge(R c7 Rs)-, or X 2 represents -NRt-;
• X3 represents -C( Rc11Rs )-, -O-C( Rc13Rs )-, -Si( Rc15Rs )-, or -Ge( Rc17Rs )-
• X4 represents -NRt-
• R N2 represents Rt.
• Each Rs independently represents an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an amino group which may have a substituent, a cyano group, or a halogen atom.
• Rs is preferably an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, or a halogen atom, and more preferably an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, or a halogen atom.
• each group represented by Rs is the same as those of each group exemplified as the substituents represented by Rc1 , Rc2 , Rc3 , Rc4, Rc5 , Rc6 , Rc7 , and Rc8 described above.
• Each Rt independently represents an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent.
• Rt is preferably an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent, and more preferably an alkyl group which may have a substituent or an aryl group which may have a substituent.
• the definitions and preferred embodiments of each group represented by Rt are the same as those of each group exemplified as the substituent represented by R N1 above.
• Substituent group S linear aliphatic hydrocarbon groups having 1 to 6 carbon atoms, branched aliphatic hydrocarbon groups having 3 to 6 carbon atoms, cyclic aliphatic hydrocarbon groups having 3 to 6 carbon atoms, aromatic ring groups which may have a substituent, and halogen atoms.
• the linear aliphatic hydrocarbon group in the above-mentioned substituent group S has 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms.
• the branched aliphatic hydrocarbon group in the above-mentioned substituent group S has 3 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms.
• the cyclic aliphatic hydrocarbon group in the above-mentioned substituent group S is preferably a monocyclic group.
• the aromatic ring group in the above-mentioned substituent group S may be either a monocyclic or polycyclic group, and is preferably a monocyclic group.
• the aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group, with an aromatic hydrocarbon group being preferred.
• the aromatic ring group preferably has 5 to 12 ring atoms, and more preferably 5 or 6 ring atoms. Examples of the substituent that the aromatic ring group may have include the substituents exemplified by the above-mentioned substituent W.
• a substituent selected from the substituent group S is preferable, and a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 6 carbon atoms, or a halogen atom is more preferable.
• the number of the substituents is preferably 1 to 3.
• Halogen atoms in the above-mentioned substituent group S include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms and chlorine atoms being preferred.
• A3 and A4 each independently represent a group represented by formula (A-1).
• C1 represents a ring containing two or more carbon atoms which may have a substituent.
• the two carbon atoms contained in C1 are the two carbon atoms clearly shown in formula (A-1).
• 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 in the ring is the number including the two carbon atoms specified in the formula.
• the ring may be either an aromatic ring or a non-aromatic ring.
• the ring may be either a monocycle or a polycycle, 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 carbon atoms in the fused ring containing at least one of a 5-membered ring and a 6-membered ring is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 10.
• the ring may have a heteroatom, such as a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, or a boron atom, and is preferably a sulfur atom, a nitrogen atom, or an oxygen atom.
• the number of heteroatoms in the ring is preferably 0 to 10, and more preferably 0 to 5.
• Examples of the substituent that the ring represented by C1 may have include the groups exemplified as the substituent W above.
• a halogen atom, an alkyl group, an aromatic ring group, a cyano group, or a silyl group is preferable, and a halogen atom or an alkyl group is more preferable.
• the alkyl group may be linear, branched or cyclic, and is preferably linear.
• the alkyl group preferably has 1 to 10 carbon atoms, and more preferably has 1 to 3 carbon atoms.
• the ring represented by C1 above is preferably a ring used as an acidic nucleus (for example, an acidic nucleus in a merocyanine dye), and examples thereof include the following nuclei.
• (b) Pyrazolinone nucleus for example, 1-phenyl-2-pyrazolin-5-one, 3-methyl-1-phenyl-2-pyrazolin-5-one, 1-(2-benzothiazolyl)-3-methyl-2-pyrazolin-5-one, and the like.
• (c) Isoxazolinone nucleus for example, 3-phenyl-2-isoxazolin-5-one, 3-methyl-2-isoxazolin-5-one, and the like.
• (d) Oxindole nucleus for example, 1-alkyl-2,3-dihydro-2-oxindole, etc.
• (e) 2,4,6-trioxohexahydropyrimidine nucleus for example, barbituric acid, 2-thiobarbituric acid, and derivatives thereof.
• the derivatives include 1-alkyl compounds such as 1-methyl and 1-ethyl, 1,3-dialkyl compounds such as 1,3-dimethyl, 1,3-diethyl, and 1,3-dibutyl, 1,3-diaryl compounds such as 1,3-diphenyl, 1,3-di(p-chlorophenyl), and 1,3-di(p-ethoxycarbonylphenyl), 1-alkyl-1-aryl compounds such as 1-ethyl-3-phenyl, and 1,3-diheteroaryl compounds such as 1,3-di(2-pyridyl).
• 2-thio-2,4-thiazolidinedione nucleus for example, rhodanine and its derivatives, etc.
• the derivatives include 3-alkylrhodanines such as 3-methylrhodanine, 3-ethylrhodanine, and 3-allylrhodanine, 3-arylrhodanine such as 3-phenylrhodanine, and 3-heteroarylrhodanine such as 3-(2-pyridyl)rhodanine, etc.
• 2-thio-2,4-oxazolidinedione nucleus (2-thio-2,4-(3H,5H)-oxazoledione nucleus): for example, 3-ethyl-2-thio-2,4-oxazolidinedione.
• 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, etc.
• (j) 2,4-thiazolidinedione nucleus: for example, 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, and 3-phenyl-2,4-thiazolidinedione.
• 2-thio-2,4-imidazolidinedione (2-thiohydantoin) nucleus for example, 2-thio-2,4-imidazolidinedione and 3-ethyl-2-thio-2,4-imidazolidinedione.
• Imidazolin-5-one nucleus for example, 2-propylmercapto-2-imidazolin-5-one, etc.
• 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, and the like.
• Indanone nucleus for example, 1-indanone, 3-phenyl-1-indanone, 3-methyl-1-indanone, 3,3-diphenyl-1-indanone, and 3,3-dimethyl-1-indanone.
• Benzofuran-3-(2H)-one nucleus for example, benzofuran-3-(2H)-one, etc.
• W 1 represents an oxygen atom, a sulfur atom, ⁇ NR W2 , or ⁇ CR W3 R W4 .
• W 1 is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom, in that the effects of the present invention are more excellent.
• R W2 represents a hydrogen atom or a substituent. Examples of the substituent include the groups exemplified as the substituent W above.
• R W3 and R W4 each independently represent a cyano group, —SO 2 R W5 , —COOR W6 or —COR W7 .
• R W5 to R W7 each independently represent 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.
• the aliphatic hydrocarbon group is as defined above, and an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred.
• the aromatic ring group is as defined above, and is preferably an aromatic hydrocarbon group, more preferably a phenyl group.
• the aliphatic heterocyclic group is as defined above, and the heteroatom contained in the aliphatic heterocyclic group is preferably a sulfur atom, an oxygen atom, or a nitrogen atom. Examples of the substituent that may be possessed by each of the groups represented by R W5 to R W7 include the substituents exemplified for the above-mentioned substituent W.
• the group represented by formula (A-1) is preferably a group represented by formula (A-2) in that the effect of the present invention is more excellent.
• C2 represents a ring containing at least 3 carbon atoms which may have a substituent.
• the three carbon atoms included in the above C2 are the three carbon atoms clearly shown in formula (A-2).
• 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 in the ring is the number including the three carbon atoms specified in the formula.
• the ring may be either an aromatic ring or a non-aromatic ring.
• the ring may be either a monocycle or a polycycle, 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 carbon atoms in the fused ring containing at least one of a 5-membered ring and a 6-membered ring is preferably 6 to 20, more preferably 6 to 15, and even more preferably 8 to 10.
• the ring may have a heteroatom, such as a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, or a boron atom, and is preferably a sulfur atom, a nitrogen atom, or an oxygen atom.
• the number of heteroatoms contained in the ring is preferably 0 to 10, and more preferably 0 to 5.
• Preferred embodiments of the substituent that the above ring may have are the same as the substituent that the above ring C1 may have.
• W 2 and W 3 each independently represent an oxygen atom or a sulfur atom, and preferably an oxygen atom in that the effects of the present invention are more excellent.
• the group represented by formula (A-2) is preferably a group represented by formula (C-1) or a group represented by formula (C-2), and more preferably a group represented by formula (C-2), in that the effects of the present invention are more excellent.
• Xc1 and Xc2 each independently represent an oxygen atom or a sulfur atom. In terms of superior effects of the present invention, it is preferable that either Xc1 or Xc2 is an oxygen atom, and it is more preferable that both Xc1 and Xc2 are oxygen atoms.
• C3 represents an aromatic ring which may have a substituent.
• the aromatic ring may be either a monocyclic ring or a polycyclic ring.
• the number of member atoms of the aromatic ring is preferably 4 to 30, more preferably 5 to 12, and even more preferably 5 to 8.
• the number of member atoms of the aromatic ring is the number including the two carbon atoms specified in the formula.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, with an aromatic hydrocarbon ring being preferred.
• the aromatic ring represented by C3 is as described above, and is preferably a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a thiophene ring, a furan ring, a thiazole ring, an oxazole ring, a pyridine ring, a thienothiophene ring, a benzothiophene ring, a benzofuran ring, a pyrazine ring, a pyrimidine ring, or a pyridazine ring, more preferably a benzene ring, a naphthalene ring, or a thiophene ring, and further preferably a benzene ring.
• substituents that the aromatic ring may have include the groups exemplified as the substituent W above, and an alkyl group or a halogen atom is preferred.
• the number of substituents that the aromatic ring may have is not particularly limited, but is preferably 0 to 8, and more preferably 0 to 4.
• X c3 to X c5 each independently represent an oxygen atom or a sulfur atom.
• X c3 and X c4 are oxygen atoms
• X c3 to X c5 are oxygen atoms.
• R c1 and R c2 each independently represent a hydrogen atom or a substituent.
• substituents include the groups exemplified as the substituent W above, and an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.
• the alkyl group may be linear, branched, or cyclic, and is preferably linear.
• the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 3 carbon atoms, and particularly preferably 1 or 2 carbon atoms.
• the aryl group may be either a monocyclic or polycyclic ring, and is preferably a phenyl group.
• the aryl group may further have a substituent, and examples of the substituent include the groups exemplified by the substituent W.
• A represents any one of the following groups.
• the two A's present in the specific compounds exemplified above may be the same or different.
• the molecular weight of the specific compound is preferably from 300 to 1,200, more preferably from 350 to 1,000, and even more preferably from 400 to 800. When the molecular weight is within the above range, it is presumed that the sublimation temperature of the specific compound is low, resulting in excellent suitability for production.
• the specific compound has an ionization potential of -5.0 to -6.0 eV in a single film.
• the maximum absorption wavelength of the specific compound is preferably in the range of 450 to 800 nm, and more preferably in the range of 500 to 650 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 compounds are particularly useful as materials for photoelectric conversion films used in imaging devices, photosensors, or photovoltaic cells.
• the specific compounds often function as dyes within the photoelectric conversion films.
• the specific compounds can also be used as coloring materials, liquid crystal materials, organic semiconductor materials, charge transport materials, medicinal materials, and fluorescent diagnostic materials.
• the particular compound may be purified if necessary.
• methods for purifying the specific compound include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, reslurry washing, reprecipitation purification, purification using an adsorbent such as activated carbon, and recrystallization purification.
• the specific compound may be used alone or in combination of two or more. When two or more types are used, the total amount thereof is preferably within the above 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.,
• Suitable aryl 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 fullerene and derivatives thereof are preferred.
• fullerenes include fullerene C60 , fullerene C70 , fullerene C76 , fullerene C78 , fullerene C80 , fullerene C82 , fullerene C84 , fullerene C90 , fullerene C96 , fullerene C240 , fullerene C540 , and mixed fullerenes.
• the fullerene derivative may be, for example, a compound in which a substituent is added to the fullerene.
• the substituent is preferably an alkyl group, an aryl group, or a heterocyclic group.
• the fullerene derivative is preferably a compound described in JP-A-2007-123707.
• the molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, and more preferably 200 to 900.
• the maximum absorption wavelength of the n-type organic semiconductor is preferably 400 nm or less or in the range of 500 to 600 nm.
• the photoelectric conversion film preferably has a bulk heterostructure formed by mixing a specific compound with an n-type organic semiconductor.
• the bulk heterostructure is a layer in the photoelectric conversion film in which a specific compound and an n-type organic semiconductor are mixed and dispersed.
• a 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.
• 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 semiconductor 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 preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and even more preferably 20 to 50 vol%.
• the content of fullerenes relative to the total content of n-type organic semiconductors is preferably 50 to 100 volume %, more preferably 80 to 100 volume %.
• Fullerenes may be used alone or in combination of two or more types.
• 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 vol%, and more preferably 40 to 80 vol%.
• the content of the specific compound is preferably 10 to 75 vol%, and more preferably 15 to 50 vol%. It is preferable that the photoelectric conversion film is substantially composed of the specific compound, the n-type organic semiconductor, and the p-type organic semiconductor contained as desired.
• the total content of the specific compound, the n-type organic semiconductor, and the p-type organic semiconductor relative to the total mass of the photoelectric conversion film is 90 to 100 volume %, preferably 95 to 100 volume %, and more preferably 99 to 100 volume %.
• the photoelectric conversion film preferably contains a p-type organic semiconductor in addition to the specific compound.
• the p-type organic semiconductor is a compound different from the above specific compound.
• a p-type organic semiconductor is a donor organic semiconductor material (compound) that has the property of easily donating electrons.
• a p-type organic semiconductor is an 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.
• 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 ( ⁇ -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 [0064] to [0065] of JP-A No.
• TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
• TPD 4,4'-bis[N-(naphthyl)-N-phen
• pyrazoline compounds e.g., thienothiophene derivatives, dibenzothiophene derivatives, benzodithiophene derivatives, dithienothiophene derivatives, [1]benzothi eno[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 JP2018-014474A, compounds described in paragraphs [0043] to [0045] of WO2016/194630, compounds described in paragraphs [0025] to [0037] and [0099] to [0109] of WO2017/159684, compounds described in paragraphs [0025] to [0037] and [0099] to [0109] of JP
• Examples of p-type organic semiconductors include benzoxazole compounds (e.g., compounds described in Figures 3 to 7 of JP-A-2022-123944), dicarbazole compounds (e.g., compounds described in Figures 2 to 5 of JP-A-2022-122839), benzoquinazoline compounds (e.g., compounds described in paragraphs [0053] to [0056] of JP-A-2022-120323), azine compounds (e.g., compounds described in paragraphs [0053] to [0056] of JP-A-2022-12027), and the like.
• benzoxazole compounds e.g., compounds described in Figures 3 to 7 of JP-A-2022-123944
• dicarbazole compounds e.g., compounds described in Figures 2 to 5 of JP-A-2022-122839
• benzoquinazoline compounds e.g., compounds described in paragraphs [0053] to [0056] of JP-A-2022-120323
• JP-A-2022-115832 compounds described in paragraphs [0041] to [0042] of JP-A-2022-115832, compounds described in Figures 2 to 10 of JP-A-2022-108268, indolotriphenylene compounds (for example, compounds described in paragraphs [0065] to [0072] of JP-A-2022-108268), and indolocarbazole compounds (for example, compounds described in paragraphs [0052] to [0073] of JP-A-2023-005703).
• p-type organic semiconductors include compounds having a smaller ionization potential than n-type organic semiconductors. If this condition is satisfied, the organic dyes exemplified as n-type organic semiconductors can be used. Examples of compounds that can be used as the p-type organic semiconductor compound are given 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 semiconductor material 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 preferably 15 to 75 vol%, more preferably 20 to 60 vol%, and even more preferably 25 to 50 vol%.
• the photoelectric conversion film containing a 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 with a luminescent quantum efficiency of 1% or less, preferably 0.5% or less, and more preferably 0.1% or less. The lower limit is often 0% or more.
• the photoelectric conversion film preferably contains a dye in addition to the specific compound.
• the dye is a compound different from the above specific compound.
• the dye is preferably 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,
• the maximum absorption wavelength of the dye is preferably in the visible light region, more preferably in the wavelength range of 400 to 650 nm, and even more preferably in the wavelength range of 400 to 550 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 preferably has an electrode.
• the electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Examples of the conductive material include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident from the upper electrode 15, the upper electrode 15 is preferably transparent to the light to be detected.
• Examples of materials constituting the upper electrode 15 include conductive metal oxides such as antimony- or fluorine-doped tin oxide (ATO: Antimony Tin Oxide, FTO: Fluorine doped Tin Oxide), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO: Indium Tin Oxide), and indium zinc oxide (IZO: Indium zinc oxide); thin metal films such as gold, silver, chromium, and nickel; mixtures or laminates of these metals and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, nanocarbon materials such as carbon nanotubes and graphene, and the like. In terms of high conductivity and transparency, conductive metal oxides are preferred.
• the sheet resistance may be 100 to 10,000 ⁇ / ⁇ , and there is a large degree of freedom in the range of the film thickness that can be thinned.
• An increase in light transmittance is preferable because it increases the light absorption in the photoelectric conversion film and increases the photoelectric conversion ability.
• the thickness of the upper electrode 15 is preferably 5 to 100 nm, and more preferably 5 to 20 nm.
• the lower electrode 11 may be made transparent or may be made non-transparent and reflective.
• Materials constituting the lower electrode 11 include, for example, conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metals such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (for example, titanium nitride (TiN)); mixtures or laminates of these metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and carbon materials such as carbon nanotubes and graphene.
• conductive metal oxides such as tin oxide doped with antimony or fluorine (ATO, FTO), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium
• 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.
• wet methods such as printing and coating
• physical methods such as vacuum deposition, sputtering, and ion plating
• chemical methods such as CVD and plasma CVD.
• the electrode material is ITO
• methods such as an electron beam method, a sputtering method, a resistance heating deposition method, a chemical reaction method (such as a sol-gel method), and coating of a dispersion of indium tin oxide can be used.
• the photoelectric conversion element preferably has one or more intermediate layers between the conductive film and the transparent conductive film in addition to the photoelectric conversion film.
• the intermediate layer may be, for example, a charge blocking film.
• the charge blocking film may be, for example, an electron blocking film or a hole blocking film.
• the electron blocking film is a donor organic semiconductor material (compound), and the above-mentioned p-type organic semiconductor can be used. Furthermore, polymeric materials can also be used as the electron blocking film. Examples of the polymeric material include polymers of phenylenevinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, and derivatives thereof.
• the electron blocking film may be made up of multiple films.
• the electron blocking film may be made of an inorganic material.
• 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, and the quantum efficiency is increased.
• examples of inorganic materials that can be used for the electron blocking film include 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, copper indium oxide, silver indium oxide, and iridium oxide.
• the hole blocking film is an acceptor organic semiconductor material (compound), and the above-mentioned n-type organic semiconductor can be used.
• the hole blocking film may be made up 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 a physical vapor deposition method such as a vacuum vapor deposition method 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 of the charge blocking films 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.
• the conductive film, the photoelectric conversion film, and the transparent conductive film are usually laminated on the substrate in this order.
• 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.
• the photoelectric conversion element can be produced by a known production method. Specifically, for example, there is mentioned a method for producing a photoelectric conversion element, which includes 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 producing a photoelectric conversion element may include other steps in addition to those described above (for example, a step of forming a charge blocking film and a step of forming a sealing layer). The method for forming each layer is as described above.
• Photoelectric conversion elements are used, for example, as imaging elements.
• An imaging element is an element that converts the optical information of an image into an electrical signal, and is usually configured with 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 method for producing the imaging element is not particularly limited, but may be a method including the step of producing the above-mentioned photoelectric conversion element.
• 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.
• the photoelectric conversion element may be used alone, or the photoelectric conversion element may be used as a line sensor in which the photoelectric conversion elements are arranged in a straight line, or as a two-dimensional sensor in which the photoelectric conversion elements are arranged on a plane.
• the specific compounds used in the photoelectric conversion film and the comparative compounds used as comparative examples are shown below.
• the compounds (1) to (11) are specific compounds, and the compounds (R-1) to (R-2) are comparative compounds.
• 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.
• amorphous ITO was formed on a glass substrate by sputtering to form a lower electrode 11 (thickness: 30 nm), and a 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).
• each specific compound or each comparative compound shown in Table 1 an n-type organic semiconductor (fullerene (C 60 )), and a p-type organic semiconductor (P-1) were co-evaporated by vacuum evaporation onto the electron blocking film 16A so as to have a thickness of 80 nm in terms of a single layer.
• the film formation speed of the photoelectric conversion film 12 was set to 1.0 ⁇ /sec.
• 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).
• an aluminum oxide (Al 2 O 3 ) layer was formed thereon by atomic layer chemical vapor deposition (ALCVD), and the resulting laminate was heated at 150° C. for 30 minutes in a glove box to obtain a photoelectric conversion element.
• the dark current was measured by the following method. A voltage was applied to the lower and upper electrodes of each photoelectric conversion element to achieve an electric field strength of 2.5 ⁇ 10 5 V/cm, and the current value in a dark place (dark current) was measured. As a result, it was confirmed that the dark current in each photoelectric conversion element was 50 nA/cm 2 or less, which is a sufficiently low dark current.
• Quantum efficiency For each photoelectric conversion element, the quantum efficiency when green and red light was received was measured by the following method. A voltage was applied to each photoelectric conversion element so as to achieve an electric field strength of 2.5 ⁇ 10 5 V/cm, and then light was irradiated from the upper electrode (transparent conductive film) side to evaluate the quantum efficiency (photoelectric conversion efficiency) at a wavelength of 560 nm. As a result, it was confirmed that the quantum efficiency was 50% or more in all photoelectric conversion elements.
• Relative response speed is less than 1.0
• Relative response speed is 1.0 or more and less than 1.5
• Relative response speed is 1.5 or more and less than 2.0
• Relative response speed is 2.0 or more and less than 3.0
• Relative response speed is 3.0 or more
• the photoelectric conversion element (B) and the photoelectric conversion element (A) in the numerator and denominator are photoelectric conversion elements prepared using the same material. The closer the value of the relative ratio B/A is to 1, the less the performance of the photoelectric conversion element is likely to deteriorate even when the film formation speed is increased, that is, the more excellent the manufacturability. In practical terms, the manufacturability is preferably evaluated as C or higher.
• Formula (S4): Relative ratio B/A (photoelectric conversion efficiency of photoelectric conversion element (B))/(photoelectric conversion efficiency of photoelectric conversion element (A))
• the "X 4 " column indicates that in formula (2), X 4 is a sulfur atom, in which case it is indicated as “A,” and otherwise it is indicated as “B.”
• the column “X 1 , X 3 " is marked with “A” if, in formula ( 1 ), X 1 is -C(R c1 R c2 )-, and R c1 and R c2 do not bond to each other to form a ring, and in formula (2), X 1 is -C(R c11 R c12 )-, and R c11 and R c12 do not bond to each other to form a ring, and marked with "B” otherwise.
• the "R c " column indicates that, in formula (1), R c1 and R c2 are different groups, R c3 and R c4 are different groups, R c5 and R c6 are different groups, R c7 and R c8 are different groups, and in formula (2), R c11 and R c12 are different groups, R c13 and R c14 are different groups, R c15 and R c16 are different groups, and R c17 and R c18 are different groups, and indicates "A” otherwise.
• the column “Formula (A-2)" indicates that A 1 and A 2 , and A 3 and A 4 are groups represented by formula (A-2), and indicates "A", and otherwise indicates "B".
• the column “Formula (C-1), Formula (C-2)” indicates that A1 and A2 , and A3 and A4 are groups represented by formula (C-1) or formula (C-2), respectively, and “B” indicates other cases.
• the "X c " column indicates that when X c1 and X c2 in formula (C-1) represent oxygen atoms and X c3 to X c5 in formula (C-2) represent oxygen atoms, the column is marked with "A,” and when they are not marked with "B.”
• Example 10 By comparing Example 10 with the other Examples, it was confirmed that the effect of the present invention is more excellent when X2 in formula (1) represents an oxygen atom or a sulfur atom.
• Example 4 By comparing Example 4 with other Examples, it was confirmed that the effects of the present invention are better when Rc1 and Rc2 , Rc3 and Rc4 , Rc5 and Rc6 , and Rc7 and Rc8 are not bonded to each other to form a ring that may have a substituent, and when Rc1 and Rc2 , Rc3 and Rc4 , Rc5 and Rc6 , and Rc7 and Rc8 are not bonded to each other to form a ring that may have a substituent.
• Example 6 From a comparison of Example 6 with other Examples, it was confirmed that when Xc1 and Xc2 in Formula (C-1) represent oxygen atoms, and Xc3 to Xc5 in Formula (C-2) represent oxygen atoms, the production suitability is superior. Comparison of Example 5 with other Examples confirmed that when A 1 and A 2 , and A 3 and A 4 are groups represented by formula (C-2), the effects and production suitability of the present invention are superior.
• compound (1) as a specific compound, an n-type organic semiconductor (fullerene (C 60 )), a p-type organic semiconductor (compound (P-1)), and any one of dyes (B-1) to (B-8) were co-evaporated by a vacuum evaporation method in a predetermined ratio (specific compound:dye:
• the photoelectric conversion element of the present invention containing the specific compound and dye has a small electric field strength dependency of the response speed to light of wavelengths of 480 nm and 560 nm, and is also excellent in response speed. Furthermore, the spectral sensitivity characteristics (IPCE: incident-photon-to-current conversion efficiency) of each photoelectric conversion element was measured, and it was confirmed that the photoelectric conversion element of the present invention containing the specific compound and dye has excellent quantum efficiency for light with a wavelength of 450 to 650 nm.
• IPCE incident-photon-to-current conversion efficiency
• the IPCE was measured by applying a voltage to each photoelectric conversion element so as to achieve an electric field strength of 2.0 x 105 V/cm, irradiating light from the upper electrode (transparent conductive film) side, and using a constant energy quantum efficiency measurement device manufactured by Optel.
• the amount of irradiated light was 50 ⁇ W/ cm2 .

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