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Definitions

• the present invention relates to a photoelectric conversion element, an image sensor, an optical sensor, and a compound.
• Patent Document 1 discloses a specific compound.
• an object of the present invention is to provide a photoelectric conversion element that has excellent quantum efficiency when receiving blue light.
• Another object of the present invention is to provide an image sensor, an optical sensor, and a compound related to the photoelectric conversion element.
• a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order A photoelectric conversion element, wherein the photoelectric conversion film contains a compound represented by formula (1) described below.
• the aromatic ring group S is a group represented by the formula (S-1) described below or the group represented by the formula (S-2) described below, or the aromatic ring group T is a group represented by the formula (S-2) described below.
• the photoelectric conversion element according to [1] which is a group represented by any one of (T-1) to formula (T-3) described below.
• the aromatic ring group S is a group represented by the formula (S-1) described below or the group represented by the formula (S-2) described below, or the aromatic ring group T is a group represented by the formula (S-2) described below.
• the present invention it is possible to provide a photoelectric conversion element that has excellent quantum efficiency when receiving blue light. Further, according to the present invention, it is possible to provide an image sensor, an optical sensor, and a compound related to the photoelectric conversion element.
• 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 (eg, 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 This means that the substituents and the like may be the same or different from each other. This point also applies to the definition of the number of substituents, etc.
• the "substituent” includes a group exemplified by the substituent W described below.
• the substituent W in this specification will be described.
• 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 (heterocyclic groups), cyano groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclicoxy groups, acyloxy groups, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, secondary or tertiary amino group (including anilino group), alkylthio group, arylthio group, heterocycl
• 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.
• the aromatic ring or the aromatic ring constituting the aromatic ring group may be either monocyclic or polycyclic (eg, 2 to 6 rings, etc.).
• a monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as a ring structure.
• a polycyclic (eg, 2-6 rings, etc.) aromatic ring is an aromatic ring in which a plurality of (eg, 2-6, etc.) aromatic ring structures are condensed as a ring structure.
• the number of ring members in the aromatic ring is preferably 5 to 15.
• the aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocycle.
• the number of heteroatoms it has as ring member atoms is, for example, 1 to 10.
• the heteroatoms include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom, and 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, and a triazine ring (for example, a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring).
• tetrazine ring e.g., 1,2,4,5-tetrazine ring, etc.
• quinoxaline ring pyrrole ring, furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, benzopyrrole ring, benzofuran ring, benzothiophene ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, naphtopyrrole ring, naphthofuran ring, naphthothiophene ring, naphthoimidazole ring, naphthoxazole ring, 3H-pyrrolidine ring, pyrroloimidazole ring (e.g., 5H- pyrrolo[1,2-a]imidazole ring, etc.), imidazoxazole ring (e.g., imidazo[2,
• examples of the type of substituent which the aromatic ring may have include the groups exemplified by the substituent W.
• the number of substituents may be 1 or more (eg, 1 to 4, etc.).
• the aromatic ring group includes, for example, a group obtained by removing one or more (eg, 1 to 5, etc.) hydrogen atoms from the above aromatic ring.
• the term aryl group includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings.
• heteroaryl group includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings.
• arylene group includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings.
• heteroarylene group includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings.
• examples of the types of substituents that these groups may have include the groups exemplified by the substituent W.
• the number of substituents may be 1 or more (eg, 1 to 4, etc.).
• the bonding direction of the divalent group (for example, -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. Among these, it is preferable that the specific compound is a trans isomer.
• the photoelectric conversion element of the present invention is a photoelectric conversion element having 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 "specific compound”). (also called).
• specific compound a compound represented by formula (1)
• the inventors of the present invention speculate as follows.
• examples of donor sites that play a role in donating electrons include basic skeletons such as benzene rings.
• Patent Document 1 The present inventors have discovered that the compounds disclosed in Patent Document 1 tend to aggregate, and as a result, charge separation in the photoelectric conversion film is not performed efficiently, which is one cause of the decrease in the quantum efficiency of photoelectric conversion elements.
• the above specific compound has Ar 1 and Ar 2 bonded to each other via a double bond or triple bond, and has specific B 1 and B 2 . It is thought that aggregation of such specific compounds is difficult to occur, and it is presumed that efficient charge separation can be achieved and the quantum efficiency of the photoelectric conversion element is improved.
• 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 specific compound.
• Ar 1 and Ar 2 represent combination 1 or combination 2.
• Combination 1 One of Ar 1 and Ar 2 represents a monocyclic divalent aromatic ring group S that may have a substituent, and the other represents a monocyclic heterocyclic group that may have a substituent. Represents an arylene group.
• Combination 2 One of Ar 1 and Ar 2 represents a bicyclic divalent aromatic ring group T which may have a substituent, and the other represents an aromatic ring group S, which may have a substituent.
• a good two-ring arylene group, or a two-ring heteroarylene group hereinafter referred to as , also referred to as "heteroarylene group T").
• L represents a group represented by formula (L-1) or a group represented by formula (L-2).
• R 1 and R 2 each independently represent a hydrogen atom or a substituent.
• B 1 and B 2 each independently represent a group represented by any one of formulas (B-1) to (B-3).
• Combination 1 is preferred as Ar 1 and Ar 2 .
• Combination 1 will be explained in detail below.
• one of Ar 1 and Ar 2 represents a monocyclic divalent aromatic ring group S which may have a substituent, and the other represents a monocyclic divalent aromatic ring group S which may have a substituent.
• the number of ring members of the aromatic ring group S is preferably 3 to 10, more preferably 4 to 8, and even more preferably 5 to 6.
• the number of carbon atoms in the aromatic ring group S is preferably 2 to 30, more preferably 3 to 12, and even more preferably 3 to 9.
• the number of carbon atoms includes the number of carbon atoms of the substituent.
• the aromatic ring group S may be either a monocyclic arylene group that may have a substituent or a monocyclic heteroarylene group that may have a substituent. Examples of the monocyclic arylene group include a phenylene group which may have a substituent.
• heteroatom contained in the monocyclic heteroarylene group examples include an oxygen atom, a sulfur atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom; Atoms are preferred.
• the number of heteroatoms in the monocyclic heteroarylene group is preferably 1 to 5, more preferably 1 or 2.
• Examples of the above-mentioned monocyclic heteroarylene group include a pyrrolylene group, an imidazolylene group, a pyrazolylene group, an oxazorylene group, a thiazorylene group, a selenophenylene group, a triazorylene group, a furanylene group, a thienylene group, which may have a substituent, Examples include a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, and a triazinylene group, and a furanylene group that may have a substituent or a thienylene group that may have a substituent is preferred.
• Examples of the substituent that the aromatic ring group S may have include the groups exemplified by the substituent W, and a halogen atom, an alkyl group, an aromatic ring group, or an alkoxy group are preferable.
• the alkyl group, aromatic ring group, and alkoxy group may further have a substituent.
• the other of Ar 1 and Ar 2 represents a monocyclic heteroarylene group which may have a substituent.
• the number of ring members in the monocyclic heteroarylene group is preferably 3 to 10, more preferably 4 to 8, and even more preferably 5 to 6.
• the number of carbon atoms in the monocyclic heteroarylene group is preferably 2 to 30, more preferably 3 to 12, and even more preferably 3 to 8.
• the monocyclic heteroarylene group has a substituent, the number of carbon atoms includes the number of carbon atoms of the substituent.
• Examples of the monocyclic heteroarylene group include monocyclic heteroarylene groups of the aromatic ring group S.
• the above substituents may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the aliphatic hydrocarbon ring and the aliphatic heterocycle include the aliphatic hydrocarbon ring and aliphatic heterocycle formed by bonding R Y1s to each other, which will be described later.
• the aromatic ring group S is preferably a group represented by formula (S-1) or a group represented by formula (S-2), and a group represented by formula (S-3) or a group represented by formula (S-4). ) is more preferable.
• R Y1 represents a hydrogen atom or a substituent. When a plurality of R Y1s exist, R Y1s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• Z 1 represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom.
• R Y2 represents a hydrogen atom or a substituent. When a plurality of R Y2s exist, R Y2s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R Y1 represents a hydrogen atom or a substituent. When a plurality of R Y1s exist, R Y1s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle. Examples of the substituent represented by R Y1 include the groups exemplified by the substituent W, and a halogen atom, an alkyl group, an aromatic ring group, or an alkoxy group are preferable.
• the halogen atom is preferably a fluorine atom or a chlorine atom.
• the alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1 to 4.
• the aromatic ring group is preferably an aryl group which may have an alkyl group.
• an alkyl group represented by R Y1 is preferable.
• the alkyl group constituting the alkoxy group is preferably an alkyl group represented by R Y1 .
• the alkyl group, aromatic ring group, and alkoxy group may further have a substituent (for example, substituent W, etc.).
• R Y1s may be the same or different.
• the number of ring members of the aliphatic hydrocarbon ring formed by bonding R Y1 to each other is preferably 5 to 20, more preferably 5 to 12, even more preferably 5 to 8.
• Examples of the aliphatic hydrocarbon ring include a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring.
• the number of ring members of the aliphatic heterocycle formed by R Y1s bonding to each other is preferably 5 to 20, more preferably 5 to 12, and even more preferably 6 to 8.
• heteroatom contained in the aliphatic heterocycle 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. preferable.
• Examples of the aliphatic heterocycle include a pyrrolidine ring, oxolane ring, thiolane ring, piperidine ring, tetrahydrofuran ring, tetrahydropyran ring, thiane ring, piperazine ring, morpholine ring, quinuclidine ring, pyrrolidine ring, azetidine ring, oxetane ring, Examples include an aziridine ring, a dioxane ring, a pentamethylene sulfide ring, and a ⁇ -butyrolactone ring.
• the aliphatic hydrocarbon ring and the aliphatic heterocycle may further have a substituent. Examples of the above-mentioned substituent include groups exemplified by substituent W.
• Z 1 represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom.
• Z 1 an oxygen atom or a sulfur atom is preferable.
• R Y2 represents a hydrogen atom or a substituent.
• R Y2s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the substituent represented by R Y2 include the substituent represented by R Y1 .
• R Y2s may be the same or different.
• the aliphatic hydrocarbon ring and aliphatic heterocycle formed by bonding R Y2 to each other include aliphatic hydrocarbon rings and aliphatic heterocycle formed by bonding R Y1 to each other. .
• * represents the bonding position.
• R SY1 represents a hydrogen atom or a substituent. When a plurality of R SY1s exist, R SY1s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• * represents the bonding position.
• Z S1 represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom.
• R SY2 represents a hydrogen atom or a substituent. When a plurality of R SY2s exist, R SY2s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R SY1 represents a hydrogen atom or a substituent.
• R SY1s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R SY1 has the same meaning as R Y1 in formula (S-1), and preferred embodiments are also the same.
• the R SY1s may be the same or different. Examples of the aliphatic hydrocarbon ring and aliphatic heterocycle formed by bonding R SY1 to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by bonding R SY1 to each other. .
• Z S1 represents an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• Z S1 has the same meaning as Z 1 in formula (S-2), and preferred embodiments are also the same.
• R SY2 represents a hydrogen atom or a substituent.
• R SY2s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R SY2 has the same meaning as R Y2 in formula (S-2), and preferred embodiments are also the same.
• the R SY2s may be the same or different. Examples of the aliphatic hydrocarbon ring and aliphatic heterocycle formed by bonding R SY2 to each other include an aliphatic hydrocarbon ring and aliphatic heterocycle formed by bonding R Y1 to each other. .
• one of Ar 1 and Ar 2 represents a bicyclic divalent aromatic ring group T which may have a substituent, and the other represents an aromatic ring group S, which has a substituent. or a two-ring heteroarylene group which may have a substituent and which contains at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom. represent.
• one of Ar 1 and Ar 2 represents a bicyclic divalent aromatic ring group T which may have a substituent.
• the aromatic ring group T is preferably a condensed ring.
• the number of ring members of the aromatic ring group T is preferably 8 to 20, more preferably 8 to 15, and even more preferably 10 to 15.
• the above-mentioned number of ring members is the total number of ring members of the two rings constituting the aromatic ring group T.
• the number of carbon atoms in the aromatic ring group T is preferably 2 to 30, more preferably 3 to 20, and even more preferably 3 to 15.
• the number of carbon atoms includes the number of carbon atoms of the substituent.
• the aromatic ring group T may be either a bicyclic arylene group which may have a substituent or a bicyclic heteroarylene group which may have a substituent.
• the above-mentioned two-ring heteroarylene group which may have a substituent may be a heteroarylene group T.
• the two-ring arylene group include a naphthalenyl group which may have a substituent.
• the two-ring heteroarylene group may have at least one aromatic heterocycle among the two rings constituting the heteroarylene group.
• the two-ring heteroarylene group may be either a benzothienylene group or a thienothienylene group.
• heteroatom contained in the above two-ring heteroarylene group examples include an oxygen atom, a sulfur atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom; Atoms are preferred.
• the number of heteroatoms in the two-ring heteroarylene group is preferably 1 to 5, more preferably 1 to 3.
• Examples of the above two-ring heteroarylene group include a thienothiophenyl group, a quinolinylene group, an isoquinolylene group, a quinoxarylene group, an indolylene group, a benzofuranylene group, a benzothienylene group, and a benzothiazolylene group, which may have a substituent.
• a thienothiophenyl group which may have a substituent, a benzofuranylene group which may have a substituent, or a benzothienylene group which may have a substituent are preferred.
• Examples of the substituent that the aromatic ring group T may have include the groups exemplified by the substituent W, with a halogen atom, an alkyl group, an aromatic ring group, or an alkoxy group being preferred.
• the alkyl group, aromatic ring group, and alkoxy group may further have a substituent.
• the other is an aromatic ring group S, a bicyclic arylene group that may have a substituent, or an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom that may have a substituent.
• the aromatic ring group S is as described above.
• Examples of the two-ring arylene group include a two-ring arylene group that may have a substituent among the aromatic ring groups T.
• the heteroarylene group T is, for example, a heteroarylene containing at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom among the two-ring heteroarylene groups of the aromatic ring group T. Examples include groups.
• the heteroarylene group T preferably contains at least one selected from the group consisting of an oxygen atom and a sulfur atom, and more preferably a sulfur atom.
• the heteroarylene group T may contain at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom, and may further contain at least one atom other than an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom. may contain a heteroatom (for example, a nitrogen atom, etc.).
• the heteroarylene group T may be a benzothiazolylene group.
• the above substituents may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the aliphatic hydrocarbon ring and the aliphatic heterocycle include an aliphatic hydrocarbon ring and an aliphatic heterocycle formed by bonding R Y1 to each other.
• the aromatic ring group T is preferably a group represented by any one of formulas (T-1) to (T-3), and preferably a group represented by any one of formulas (T-4) to (T-6). More preferred are groups such as
• Z 2 represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom.
• R Y3 represents a hydrogen atom or a substituent.
• R Y3s When a plurality of R Y3s exist, R Y3s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R Y4 represents a hydrogen atom or a substituent.
• R Y5 represents a hydrogen atom or a substituent.
• R Y5s When a plurality of R Y5s exist, R Y5s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• Z 2 represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom.
• Z 2 an oxygen atom or a sulfur atom is preferable.
• R Y3 represents a hydrogen atom or a substituent.
• R Y3s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the substituent represented by R Y3 include the substituent represented by R Y1 .
• R Y3s may be the same or different.
• Examples of aliphatic hydrocarbon rings and aliphatic heterocycles formed by R Y3s bonding to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by R Y1s bonding to each other. .
• the broken line in the ring containing -Z 3 -Y 13 -Z 4 - means that the ring is an aromatic ring.
• R Y4 represents a hydrogen atom or a substituent.
• R Y4s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the substituent represented by R Y4 include the substituent represented by R Y1 .
• R Y4s may be the same or different.
• the aliphatic hydrocarbon ring and aliphatic heterocycle formed by bonding R Y4 to each other include aliphatic hydrocarbon rings and aliphatic heterocycle formed by bonding R Y1 to each other. .
• R Y5 represents a hydrogen atom or a substituent.
• R Y5s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the substituent represented by R Y5 include the substituent represented by R Y1 .
• R Y5s may be the same or different.
• the aliphatic hydrocarbon ring and aliphatic heterocycle formed by R Y5s bonding to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by R Y1s bonding to each other. .
• * represents the bonding position.
• R T1 represents a hydrogen atom or a substituent.
• Z T1 and Z T2 each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• * represents the bonding position.
• R T2 represents a hydrogen atom or a substituent. When a plurality of R T2s exist, the R T2s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• Z T3 represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom.
• * represents the bonding position.
• R T3 represents a hydrogen atom or a substituent. When a plurality of R T3s exist, the R T3s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R T1 represents a hydrogen atom or a substituent.
• ⁇ CR T1 is preferable.
• Examples of the substituent represented by R T1 include the substituent represented by R Y1 .
• the RT1s may be the same or different.
• Z T1 and Z T2 each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• Z T1 and Z T2 are preferably oxygen atoms or sulfur atoms.
• ⁇ CR T2 is preferable.
• R T2 represents a hydrogen atom or a substituent.
• the R T2s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the substituent represented by R T2 include the substituent represented by R Y1 .
• the RT2s may be the same or different.
• the aliphatic hydrocarbon ring and aliphatic heterocycle formed by R T2s bonding to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by R Y1s bonding to each other. .
• Z T3 represents an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• Z T3 is preferably an oxygen atom or a sulfur atom.
• ⁇ CR T3 is preferable.
• R T3 represents a hydrogen atom or a substituent.
• the R T3s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• the substituent represented by R T3 include the substituent represented by R Y1 .
• the RT3s may be the same or different.
• Examples of aliphatic hydrocarbon rings and aliphatic heterocycles formed by R T3s bonding to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by R Y1s bonding to each other. .
• At least one of Ar 1 and Ar 2 preferably represents an aromatic ring group S.
• L represents a group represented by formula (L-1) or a group represented by formula (L-2).
• L is preferably a group represented by formula (L-1).
• R L1 and R L2 each independently represent a hydrogen atom, a halogen atom, a monovalent aliphatic hydrocarbon group that may have a substituent, or a monovalent aromatic ring group that may have a substituent.
• -OR L3 or -SR L4 R L3 and R L4 each independently represent a monovalent aliphatic hydrocarbon group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• * represents the bonding position.
• Ar 1 and Ar 2 are bonded via the group represented by formula (1), and the bond configuration is either cis configuration or trans configuration.
• a transformer arrangement is preferred.
• the compound represented by formula (1) is preferably in the trans form with respect to the group represented by formula (L-1).
• R L1 and R L2 each independently have a hydrogen atom, a halogen atom, a monovalent aliphatic hydrocarbon group that may have a substituent, or a substituent. represents an optional monovalent aromatic ring group, -OR L3 or -SR L4 .
• R L3 and R L4 each independently represent a monovalent aliphatic hydrocarbon group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• the halogen atom is preferably a fluorine atom or a chlorine atom.
• the monovalent aliphatic hydrocarbon group which may have a substituent represented by R L1 to R L4 above is preferably an alkyl group having 1 to 4 carbon atoms.
• an aryl group which may have an alkyl group is preferable.
• the alkyl group that the aryl group may have is preferably an alkyl group having 1 to 4 carbon atoms.
• Examples of the substituents that the aliphatic hydrocarbon group and the aromatic ring group may have include the groups exemplified by the substituent W.
• R L1 and R L2 are preferably a hydrogen atom, a halogen atom or -OR L3 , and more preferably a hydrogen atom.
• R 1 and R 2 each independently represent a hydrogen atom or a substituent.
• substituent W examples of the above-mentioned substituent include groups exemplified by substituent W. Hydrogen atoms are preferred as R 1 and R 2 .
• B 1 and B 2 each independently represent a group represented by any one of formulas (B-1) to (B-3).
• B 1 and B 2 are preferably a group represented by formula (B-1), more preferably a group represented by formula (B-4) or a group represented by formula (B-5).
• C 1 represents a ring containing two or more carbon atoms and X 1 and which may have a substituent.
• R B1 represents a hydrogen atom or a substituent.
• R B2 and R B3 each independently represent a cyano group, -SO 2 R B4 , -COOR B5 or -COR B6 .
• R B4 to R B6 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• X 1 represents an oxygen atom, a sulfur atom, -CO-, -CS-, -SO-, or -SO 2 -.
• * represents the bonding position.
• A represents a monovalent aliphatic hydrocarbon group which may have a substituent or a monovalent aromatic ring group which may have a substituent.
• * represents the bonding position.
• C 2 represents a ring containing two or more carbon atoms, N, X 2 and X 3 and optionally having a substituent.
• R B7 each independently represents a hydrogen atom or a substituent.
• R B8 represents a hydrogen atom or a substituent.
• R B9 and R B10 each independently represent a cyano group, -SO 2 R B11 , -COOR B12 or -COR B13 .
• R B11 to R B13 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• R B14 and R B15 each independently represent a hydrogen atom or a substituent.
• R B16 and R B17 each independently represent a hydrogen atom or a substituent.
• C 1 represents a ring containing two or more carbon atoms and X 1 and which may have a substituent.
• the above ring is a ring containing two or more carbon atoms and containing -X 1 - as specified in formula (B-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. Note that the above carbon number is a number that includes two carbon atoms specified in the formula.
• 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 above ring may contain a heteroatom. Examples of the heteroatom include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom, and boron atom, with oxygen atom, sulfur atom, or nitrogen atom being preferred.
• the number of heteroatoms in the ring is preferably 0 to 10, more preferably 0 to 5.
• Examples of the substituent that the ring may have include the groups exemplified by the substituent W above, 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.
• an oxygen atom is preferable.
• X 1 -CO- is preferable.
• * represents the bonding position.
• R Z1 represents a hydrogen atom or a substituent.
• R Z2 and R Z3 each independently represent a cyano group, -SO 2 R Z4 , -COOR Z5 or -COR Z6 .
• R Z4 to R Z6 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• X B2 represents an oxygen atom or a sulfur atom.
• C3 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
• * represents the bonding position.
• R Z7 represents a hydrogen atom or a substituent.
• R Z8 and R Z9 each independently represent a cyano group, -SO 2 R Z10 , -COOR Z11 or -COR Z12 .
• R Z10 to R Z12 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• X B4 represents an oxygen atom or a sulfur atom.
• R X1 and R X2 each independently represent a hydrogen atom or a substituent.
• X B1 has the same meaning as D 1 in formula (B-1), and preferred embodiments are also the same.
• R Z1 to R Z6 have the same meanings as R B1 to R B6 in formula (B-1), respectively, and preferred embodiments are also the same.
• X B2 represents an oxygen atom or a sulfur atom.
• X B2 an oxygen atom is preferable.
• C 3 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
• the number of carbon atoms in the aromatic ring is preferably 5 to 30, more preferably 5 to 12, and even more preferably 6 to 8. Note that the above carbon number is a number that includes two carbon atoms specified in the formula.
• the aromatic ring may be either monocyclic or polycyclic.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, and an aromatic hydrocarbon ring is preferred.
• the aromatic ring is preferably a benzene ring, a naphthalene ring, an anthracene ring or a pyrene ring, and more preferably a benzene ring.
• Examples of the substituent that the aromatic ring may have include the groups exemplified by the substituent W above.
• the group represented by formula (B-4) is preferably a group represented by formula (B-6).
• R Z13 represents a hydrogen atom or a substituent.
• R Z14 and R Z15 each independently represent a cyano group, -SO 2 R Z16 , -COOR Z17 or -COR Z18 .
• R Z16 to R Z18 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• X B7 represents an oxygen atom or a sulfur atom.
• R X3 to R X6 each independently represent a hydrogen atom, an alkyl group that may have a substituent, a halogen atom, or an alkoxy group.
• X B6 has the same meaning as D 1 in formula (B-1), and preferred embodiments are also the same.
• R Z13 to R Z18 have the same meanings as R B1 to R B6 in formula (B-1), respectively, and preferred embodiments are also the same.
• X B7 has the same meaning as X B2 in formula (B-1), and preferred embodiments are also the same.
• R X3 to R X6 are preferably a hydrogen atom, an alkyl group or a halogen atom.
• R Z7 represents a hydrogen atom or a substituent.
• R Z8 and R Z9 each independently represent a cyano group, -SO 2 R Z10 , -COOR Z11 or -COR Z12 .
• R Z10 to R Z12 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• X B4 represents an oxygen atom or a sulfur atom.
• X B3 and X B5 have the same meaning as D 1 in formula (B-1), and preferred embodiments are also the same.
• R Z13 to R Z18 have the same meanings as R B1 to R B6 in formula (B-1), respectively, and preferred embodiments are also the same.
• X B4 has the same meaning as X B2 in formula (B-4), and preferred embodiments are also the same.
• R X1 and R X2 each independently represent a hydrogen atom or a substituent.
• substituent W preferably an alkyl group, and more preferably an alkyl group having 1 to 3 carbon atoms.
• A represents a monovalent aliphatic hydrocarbon group which may have a substituent or a monovalent aromatic ring group which may have a substituent.
• the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 15.
• the aliphatic hydrocarbon group is preferably an alkyl group. Further, the aliphatic hydrocarbon group may be linear, branched, or cyclic.
• the aromatic ring group is preferably an aryl group that may have a halogen atom or an aryl group that may have an alkyl group.
• the alkyl group that the aryl group may have is preferably an alkyl group having 1 to 4 carbon atoms. Examples of the substituents that the aliphatic hydrocarbon group and the aromatic ring group may have include the groups exemplified by the substituent W.
• C 2 represents a ring containing two or more carbon atoms, N, X 2 and X 3 and which may have a substituent.
• the above ring is a ring containing two or more carbon atoms, -N-X 2 - and -X 3 - bonds, as specified in formula (B-3).
• 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. Note that the above carbon number is a number that includes two carbon atoms specified in the formula.
• 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.
• examples of the heteroatoms contained in the ring include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom, and boron atom.
• An oxygen atom, a sulfur atom or a nitrogen atom is preferred.
• the number of heteroatoms in the ring is preferably 1 to 10, more preferably 1 to 5.
• substituents that the ring may have include the groups exemplified by the substituent W above, and preferably a halogen atom, an alkyl group, an aromatic ring group, a cyano group, or a silyl group.
• R B7 each independently represents a hydrogen atom or a substituent.
• substituents include the substituent represented by R Y1 .
• R B8 represents a hydrogen atom or a substituent.
• R B9 and R B10 each independently represent a cyano group, -SO 2 R B11 , -COOR B12 or -COR B13 .
• R B11 to R B13 each independently represent an alkyl group that may have a substituent or a monovalent aromatic ring group that may have a substituent.
• D 2 has the same meaning as D 1 in formula (B-1), and preferred embodiments are also the same.
• R B8 to R B13 have the same meanings as R B1 to R B6 in formula (B-1), respectively, and preferred embodiments are also the same.
• R B14 and R B15 each independently represent a hydrogen atom or a substituent.
• R B16 and R B17 each independently represent a hydrogen atom or a substituent.
• Examples of the above substituent include the substituent represented by R Y1 .
• the compound represented by formula (1) is preferably a compound represented by formula (2) or a compound represented by formula (3).
• Z 7 and Z 8 each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• R Y6 represents a hydrogen atom or a substituent. When a plurality of R Y6s exist, R Y6s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R 1 and R 2 each independently represent a hydrogen atom or a substituent.
• L represents a group represented by formula (L-1) or a group represented by formula (L-2).
• B 1 and B 2 each independently represent a group represented by any one of formulas (B-1) to (B-3).
• Z 9 represents an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• R Y7 represents a hydrogen atom or a substituent. When a plurality of R Y7s exist, R Y7s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R 1 and R 2 each independently represent a hydrogen atom or a substituent.
• L represents a group represented by formula (L-1) or a group represented by formula (L-2).
• B 1 and B 2 each independently represent a group represented by any one of formulas (B-1) to (B-3).
• Z 7 and Z 8 each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• Z 7 and Z 8 are preferably oxygen atoms or sulfur atoms.
• R Y6 represents a hydrogen atom or a substituent.
• R Y6s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R Y6 include the substituent represented by R Y1 .
• R Y6s may be the same or different.
• the aliphatic hydrocarbon ring and aliphatic heterocycle formed by R Y6 bonding to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by bonding R Y1 to each other. .
• R 1 , R 2 , L, B 1 and B 2 have the same meanings as R 1 , R 2 , L, B 1 and B 2 in formula (1), and preferred embodiments also include It's the same.
• Z 9 represents an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.
• Z 9 is preferably an oxygen atom or a sulfur atom.
• R Y7 represents a hydrogen atom or a substituent.
• R Y7s may be bonded to each other to form an aliphatic hydrocarbon ring or an aliphatic heterocycle.
• R Y7 include the substituent represented by R Y1 .
• R Y7s may be the same or different.
• the aliphatic hydrocarbon ring and aliphatic heterocycle formed by R Y7s bonding to each other include aliphatic hydrocarbon rings and aliphatic heterocycles formed by R Y1s bonding to each other. .
• R 1 , R 2 , L, B 1 and B 2 have the same meanings as R 1 , R 2 , L, B 1 and B 2 in formula (1), and preferred embodiments also include It's the same.
• 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.
• examples of the specific compound include the following compounds.
• 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 400 to 600 nm, more preferably in the range of 400 to 500 nm.
• the above-mentioned 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 maximum absorption wavelength of the specific compound is determined by vapor-depositing the specific compound and using the specific compound in a film state.
• 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.
• 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 photoelectric conversion film contains an n-type organic semiconductor in addition to the above-mentioned specific compound.
• the n-type organic semiconductor is a compound different from the above-mentioned specific compound.
• An n-type organic semiconductor is an acceptor organic semiconductor material (compound), and refers to an organic compound that has the property of easily accepting electrons. That is, an n-type organic semiconductor refers to an organic compound that has a larger electron affinity when two organic compounds are used in contact with each other. That is, any organic compound can be used as the acceptor organic semiconductor as long as it has electron-accepting properties.
• n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof; fused aromatic carbocyclic compounds (for example, naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, fluoranthene derivatives, etc.); 5- to 7-membered heterocyclic compounds having at least one member 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, pyrazole, imidazole and thiazole, etc.
• fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred.
• fullerenes include fullerene C 60 , fullerene C 70 , fullerene C 76 , fullerene C 78 , fullerene C 80 , fullerene C 82 , fullerene C 84 , fullerene C 90 , fullerene C 96 , fullerene C 240 , fullerene C 540 , and Mixed fullerenes are mentioned.
• fullerene derivatives include compounds obtained by adding a substituent to the above-mentioned 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 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 40 to 80% by volume.
• the content of the specific compound is preferably 15 to 75% by volume, more preferably 30 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% by volume, preferably 95 to 100% by 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, the 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 JP-A No. 2011-225544, compounds described in paragraphs [0119] to [0158] of JP-A No.
• TPD N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
• ⁇ -NPD 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl
• JP-A-2015-153910 Compounds described in [0051] and compounds described in paragraphs [0086] to [0090] of JP 2012-094660, JP 2022-123944, JP 2022-122839, JP 2022-120323 No.
• 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 semiconductor compounds are listed 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 materials 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 25-50% 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 acceptor-donor-acceptor type dyes, donor-acceptor-donor type dyes, imidazoquinoxaline dyes (WO 2020/013246, WO 2022/168856, JP 2023-010305, Compounds described in JP-A No.
• cyanine dyes styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes , squarylium dye, croconium dye, azamethine dye, coumarin dye, arylidene dye, anthraquinone dye, triphenylmethane dye, azo dye, azomethine dye, metallocene dye, fluorenone dye, fulgide dye, perylene dye, phenazine dye, phenothiazine dye, quinone dye , diphenylmethane dye, polyene dye, acridine dye, acridinone dye, diphenylamine dye, quinophthalone dye, phenoxazine dye, phthaloper
• 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 450 to 650 nm.
• the dyes may be used alone or in combination of two or more.
• the film thickness (layer equivalent) ⁇ 100) is preferably 15 to 75% by volume, more preferably 20 to 60% by volume, and even more preferably 25 to 50% by volume.
• Dry film forming methods include, for example, physical vapor deposition methods such as evaporation methods (especially vacuum evaporation methods), sputtering methods, ion plating methods, and MBE (Molecular Beam Epitaxy) methods, as well as CVD (Chemical) methods such as plasma polymerization. Vapor Deposition) method is mentioned, and vacuum evaporation method is preferable.
• manufacturing conditions such as the degree of vacuum and the evaporation 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. and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, 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 (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
• conductive metal oxides metals such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN), etc.); mixtures or laminates of 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 a plurality of 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. Note that the hole blocking film may be composed of a plurality of films.
• Examples of the method for manufacturing the charge blocking film include a dry film forming method and a wet film forming method.
• Examples of the dry film forming method 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, and a physical vapor deposition method such as a vacuum vapor deposition method is preferable.
• Examples of wet film forming methods include inkjet method, spray method, nozzle printing method, spin coating method, dip coating method, casting method, die coating method, roll coating method, bar coating method, and gravure coating method. In terms of patterning, the inkjet method is preferred.
• 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 deteriorate significantly due to the presence of deterioration factors such as water molecules. Therefore, the entire photoelectric conversion film is covered with a sealing layer made of dense ceramics such as metal oxide, metal nitride, or metal nitride oxide, or diamond-like carbon (DLC), which does not allow water molecules to penetrate. The above deterioration can be prevented by sealing.
• the sealing layer include the descriptions in paragraphs [0210] to [0215] of JP-A No. 2011-082508, the contents of which are incorporated herein.
• 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 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 a compound (EB-1) is further vacuum-heated and vapor-deposited on the lower electrode 11.
• An electron blocking film 16A was formed by a method.
• each compound shown in Table 1 compound D-1 as a p-type organic semiconductor, and C 60 as an n-type organic semiconductor, were added in a predetermined ratio onto the electron blocking film 16A. (1:1:1, thickness conversion) was codeposited using a vacuum evaporation method to form a film. As a result, a photoelectric conversion film 12 having a bulk heterostructure with a thickness of 240 nm was formed. Furthermore, a compound (EB-2) was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm).
• Amorphous ITO was deposited on the hole blocking film 16B by sputtering to form the upper electrode 15 (transparent conductive film) (thickness: 10 nm).
• an SiO film as a sealing layer on the upper electrode 15 by vacuum evaporation
• an aluminum oxide (Al 2 O 3 ) layer was formed thereon by ALCVD (Atomic Layer Chemical Vapor Deposition).
• ALCVD Atomic Layer Chemical Vapor Deposition
• 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 determine the quantum efficiency (photoelectric conversion) at a wavelength of 460 nm. efficiency) was evaluated, and the quantum efficiency was determined according to equation (S1).
• Quantum efficiency (relative ratio) (Quantum efficiency at wavelength 460 nm of each example or each comparative example) / (Quantum efficiency at wavelength 460 nm 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 at a wavelength of 460 nm at that time is measured with an oscilloscope, and the signal intensity 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 460 nm of each example or each comparative example) / (Rise time at wavelength 460 nm of Example 1-1)
• Example 1-1 the rise time at 7.5 ⁇ 10 4 V/cm at a wavelength of 460 nm in Example 1-1 and the rise time at 2.0 ⁇ 10 5 V at a wavelength of 460 nm in Example 1-1 Compare the rise time at /cm.
• Table 1 shows the evaluation results of Test X above. Each notation in Table 1 indicates the following.
• the "Combination 1 or Combination 2" column indicates whether Ar 1 and Ar 2 are combination 1 or combination 2.
• the "Aromatic ring group S” column the case where at least one of Ar 1 and Ar 2 represents the aromatic ring group S was marked as "A”, and the other cases were marked as "B".
• the "Formula (B-1)” column cases where B 1 and B 2 were groups represented by formula (B-1) were marked as "A”, and other cases were marked as "B”.
• In the "Formula (L-1)” column cases where L is a group represented by formula (L-1) are marked as "A”, and other cases are marked as "B”.
• R L1 and R L2 are hydrogen atoms
• the case where R L1 and R L2 are hydrogen atoms is marked as "A”
• the other cases are marked as "B”.
• 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 wavelengths of 460 nm and 600 nm. was evaluated, and the quantum efficiency was determined according to equation (S4). Note that when determining the quantum efficiency, the numerator and denominator are the quantum efficiencies at the same wavelength.
• Quantum efficiency (relative ratio) (Quantum efficiency at wavelength 460 nm or wavelength 600 nm of each example or each comparative example) / (Quantum efficiency at wavelength 460 nm or wavelength 600 nm of Example 2-1)
• Quantum efficiency is less than 0.4
• Relative response speed (Rise time at wavelength 460 nm or wavelength 600 nm of each example or each comparative example) / (Rise time at wavelength 460 nm or wavelength 600 nm of Example 2-1)
• Relative response speed is 2.0 or more
• Electric field strength dependence of response speed (rise time at 7.5 ⁇ 10 4 V/cm at wavelength 460 nm or wavelength 600 nm of each example or each comparative example)/(each example or each comparison Rise time at 2.0 ⁇ 10 5 V/cm at wavelength 460 nm or wavelength 600 nm)
• the dependence of response speed on electric field strength is 5.0 or more
• Table 2 shows the evaluation results of Test Y. Each notation in Table 2 is the same as each notation in Table 1 described above.

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