JP2023010305A - Photoelectric converter, imager, photosensor, and compound - Google Patents

Abstract

To provide a photoelectric converter excellent in manufacturing suitability and also excellent in photoelectric conversion efficiency for a specific wavelength; and an imager, a photosensor and a compound.SOLUTION: The photoelectric converter has a conductive film, a photoelectric conversion film and a transparent conductive film in this order, where the photoelectric conversion film contains a compound represented by formula (1).SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a photoelectric conversion device, an imaging device, an optical sensor, and a compound.

In recent years, the development of devices having a photoelectric conversion film has progressed. For example, Patent Document 1 discloses a compound represented by the following formula as a material applied to a photoelectric conversion element.

WO2020/013246

2. Description of the Related Art In recent years, along with the demand for improved performance of imaging devices, optical sensors, and the like, there is a demand for further improvement in various characteristics required of photoelectric conversion devices used in these devices. For example, in the photoelectric conversion element, the photoelectric conversion film possessed by the photoelectric conversion element must be excellent in manufacturing aptitude, and the photoelectric conversion element for green light (e.g., wavelength 500 nm) and red light (e.g., wavelength 600 nm). Excellent conversion efficiency (hereinafter also referred to as “photoelectric conversion efficiency for a specific wavelength”) is required.
The manufacturability means that a photoelectric conversion element having excellent photoelectric conversion efficiency can be obtained even when the film formation speed of the photoelectric conversion film is increased.

The present inventors have studied photoelectric conversion elements using compounds disclosed in Patent Document 1 and the like, and have found that it is difficult to achieve both manufacturing suitability and photoelectric conversion efficiency for a specific wavelength.

Accordingly, an object of the present invention is to provide a photoelectric conversion element that is excellent in manufacturability and also excellent in photoelectric conversion efficiency with respect to a specific wavelength. Another object of the present invention is to provide an imaging device, an optical sensor, and a compound.

As a result of intensive studies on the above problems, the present inventors have found that the above problems can be solved by using a compound having a predetermined structure in a photoelectric conversion film, and have completed the present invention.

[1]
A photoelectric conversion element having a conductive film, a photoelectric conversion film and a transparent conductive film in this order,
A photoelectric conversion device, wherein the photoelectric conversion film contains a compound represented by formula (1) described later.
[2]
The photoelectric conversion device according to [1], wherein Y ^a11 is an oxygen atom.
[3]
The photoelectric conversion device according to [1] or [2], wherein Ar ^a11 is a five-membered ring.
[4]
The photoelectric conversion device according to any one of [1] to [3], wherein A ¹ is a group represented by formula (2A) described later or a group represented by formula (3A) described later.
[5]
The photoelectric conversion element according to any one of [1] to [4], wherein D ¹ is a group represented by any one of formulas (1D) to (3D) described below.
[6]
The photoelectric conversion element according to [5], wherein D ¹ is a group represented by formula (1D) described later.
[7]
The photoelectric conversion device according to any one of [1] to [6], wherein D ¹ is a group represented by formula (4D) described later.
[8]
The photoelectric conversion device according to any one of [1] to [7], wherein D ¹ is a group represented by formula (5D) described later.
[9]
The photoelectric conversion device according to any one of [1] to [8], wherein D ¹ is a group represented by formula (6D) described later.
[10]
The photoelectric conversion film further contains an n-type organic semiconductor,
Any one of [1] to [9], wherein the photoelectric conversion film has a bulk heterostructure formed in a state where the compound represented by the formula (1) described later and the n-type organic semiconductor are mixed. or the photoelectric conversion element according to one.
[11]
The photoelectric conversion device according to [10], wherein the n-type organic semiconductor contains fullerenes selected from the group consisting of fullerenes and derivatives thereof.
[12]
The photoelectric conversion element according to [10] or [11], wherein the photoelectric conversion film further contains a p-type organic semiconductor.
[13]
The photoelectric conversion element according to any one of [1] to [12], which has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
[14]
An imaging device comprising the photoelectric conversion device according to any one of [1] to [13].
[15]
An optical sensor comprising the photoelectric conversion element according to any one of [1] to [13].
[16]
A compound represented by formula (1) described later.
[17]
The compound of [16], wherein Y ^a11 is an oxygen atom.
[18]
The compound of [16] or [17], wherein Ar ^a11 is a 5-membered ring.
[19]
The compound according to any one of [16] to [18], wherein A ¹ is a group represented by formula (2A) described below or a group represented by formula (3A) described below.
[20]
The compound according to any one of [16] to [19], wherein D ¹ is a group represented by any one of formulas (1D) to (3D) described below.
[21]
The compound according to [20], wherein D ¹ is a group represented by formula (1D) described later.
[22]
The compound according to any one of [16] to [21], wherein D ¹ is a group represented by formula (4D) described later.
[23]
The compound according to any one of [16] to [22], wherein D ¹ is a group represented by formula (5D) described later.
[24]
The compound according to any one of [16] to [23], wherein D ¹ is a group represented by formula (6D) described below.

ADVANTAGE OF THE INVENTION According to this invention, the photoelectric conversion element which is excellent in the manufacturing aptitude, and is excellent also in the photoelectric conversion efficiency with respect to a specific wavelength can be provided. Further, according to the present invention, an imaging device, an optical sensor, and a compound can be provided.

It is a cross-sectional schematic diagram which shows one structural example of a photoelectric conversion element. It is a cross-sectional schematic diagram which shows one structural example of a photoelectric conversion element.

Preferred embodiments of the photoelectric conversion device of the present invention are described below.
In the present specification, a numerical range represented using "to" means a range including the numerical values described before and after "to" as lower and upper limits.
In this specification, when there are multiple substituents, linking groups, etc. (hereinafter also referred to as "substituents, etc.") indicated by specific symbols, or when multiple substituents, etc. are defined at the same time, each It means that 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 and the like.
As used herein, the hydrogen atom may be a protium atom (ordinary hydrogen atom) or a deuterium atom (eg, a double hydrogen atom, etc.).
In the present specification, unless otherwise specified, the "substituent" includes groups exemplified for the substituent W described later.

(Substituent W)
The substituent W in this specification is described.
Substituent W is, for example, a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), alkyl group (including cycloalkyl group, bicycloalkyl group, and tricycloalkyl group), alkenyl group ( cycloalkenyl groups and bicycloalkenyl groups), alkynyl groups, aryl groups, heteroaryl groups (also referred to as heterocyclic groups), cyano groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocycles oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, secondary or tertiary amino group (including anilino group), alkylthio group, arylthio group, heterocyclic thio group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, aryl or heterocyclic azo group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, A phosphono group, a silyl group, a carboxy group, a phosphate group, a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, a ureido group, a boronic acid group and a primary amino group. In addition, each group described above may further have a substituent (for example, one or more groups among the groups described above), if possible. For example, an alkyl group which may have a substituent is also included as one form of the substituent W.
Further, when the substituent W has carbon atoms, the carbon number of the substituent W is, for example, 1 to 20.
The number of atoms other than hydrogen atoms possessed by the substituent W is, for example, 1-30.
In addition, the specific compound has, as a substituent, 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, a ureido group, a boron It is also preferred not to have acid groups (-B(OH) ₂ ) and/or primary amino groups.

As used herein, halogen atoms include, for example, fluorine, chlorine, bromine and iodine atoms.

In this specification, unless otherwise specified, the number of carbon atoms in the alkyl group is preferably 1-20, more preferably 1-10, and even more preferably 1-6.
Alkyl groups may be linear, branched or cyclic.
Alkyl groups include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, n-hexyl and cyclopentyl groups.
Also, the alkyl group may be, for example, a cycloalkyl group, a bicycloalkyl group, or a tricycloalkyl group, and may have a cyclic structure thereof as a partial structure.
In the alkyl group which may have a substituent, the substituent which the alkyl group may have is not particularly limited. has 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).

In this specification, unless otherwise specified, the alkyl group moiety in the alkoxy group is preferably the above alkyl group. The alkyl group portion in the alkylthio group is preferably the alkyl group described above.
In the alkoxy group which may have a substituent, examples of the substituent which the alkoxy group may have are the same as those of the alkyl group which may have a substituent. In the alkylthio group which may have a substituent, examples of the substituent which the alkylthio group may have are the same as those of the alkyl group which may have a substituent.

In this specification, unless otherwise specified, alkenyl groups may be linear, branched or cyclic. The alkenyl group preferably has 2 to 20 carbon atoms. In the alkenyl group which may have a substituent, examples of the substituent which the alkenyl group may have are the same as those of the alkyl group which may have a substituent.
In this specification, unless otherwise specified, alkynyl groups may be linear, branched or cyclic. The alkynyl group preferably has 2 to 20 carbon atoms. In the alkynyl group which may have a substituent, examples of the substituent which the alkynyl group may have are the same as those of the alkyl group which may have a substituent.

In the present specification, unless otherwise specified, examples of silyl groups which may have substituents include groups represented by —Si(R ^S1 )(R ^S2 )(R ^S3 ). R ^S1 , R ^S2 and R ^S3 each independently represent a hydrogen atom or a substituent, an optionally substituted alkyl group, an optionally substituted alkoxy group, or a substituted It preferably represents an alkylthio group which may be substituted, an aryl group which may be substituted, or a heteroaryl group which may be substituted.

In the present specification, unless otherwise specified, aromatic rings may be either monocyclic or polycyclic (eg, 2 to 6 rings). A monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as a ring structure. A polycyclic (eg, 2 to 6, etc.) aromatic ring is an aromatic ring in which a plurality of (eg, 2 to 6, etc.) aromatic ring structures are condensed as a ring structure.
The number of ring member atoms in the aromatic ring is preferably 5-15.
The aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
When the above aromatic ring is an aromatic heterocyclic ring, the number of heteroatoms it has as ring member atoms is, for example, 1-10. Examples of the heteroatom include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom and boron atom.
Examples of the aromatic hydrocarbon ring include benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring.
Examples of the aromatic heterocyclic ring include pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring (1,2,3-triazine ring, 1,2,4-triazine ring, 1,3,5-triazine ring, ring, etc.) and tetrazine ring (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, naphthopyrrole ring, naphthofuran ring, naphthothiophene ring, naphthoimidazole ring, naphthoxazole ring, 3H-pyrrolidine ring, pyrroloimidazole ring (5H-pyrrolo[1,2- a] imidazole ring, etc.), imidazooxazole ring (imidazo[2,1-b]oxazole ring, etc.), thienothiazole ring (thieno[2,3-d]thiazole ring, etc.), benzothiadiazole ring, benzodithiophene ring ( benzo[1,2-b:4,5-b′]dithiophene ring, etc.), thienothiophene ring (thieno[3,2-b]thiophene ring, etc.), thiazolothiazole ring (thiazolo[5,4-d] thiazole ring, etc.), naphthodithiophene ring (naphtho[2,3-b:6,7-b′]dithiophene ring, naphtho[2,1-b:6,5-b′]dithiophene ring, naphtho[1, 2-b: 5,6-b′]dithiophene ring, 1,8-dithiadicyclopenta[b,g]naphthalene ring, etc.), benzothienobenzothiophene ring, dithieno[3,2-b: 2′,3 '-d]thiophene ring and 3,4,7,8-tetrathiadicyclopenta[a,e]pentalene ring.
In the aromatic ring which may have a substituent, the type of substituent which the aromatic ring may have is not particularly limited, and examples thereof include a substituent W. Substitution when the aromatic ring has a substituent The number of groups may be 1 or more (eg, 1 to 4).
In the present specification, the aromatic ring group includes, for example, a group obtained by removing one or more (eg, 1 to 5) hydrogen atoms from the above aromatic ring.
In the present specification, an 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.
In the present specification, the term "heteroaryl group" includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocyclic ring among the above aromatic rings.
In the present specification, the term arylene group includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings.
In the present specification, the term "heteroarylene group" includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocyclic ring among the above aromatic rings.
An aromatic ring group which may have a substituent, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an arylene group which may have a substituent, and a substituent In the heteroarylene group which may have, the type of substituent which these groups may have is not particularly limited, and examples thereof include the substituent W. When these groups which may have substituents have substituents, the number of substituents may be 1 or more (eg, 1 to 4).

In this specification, in one formula (general formula) representing a chemical structure, when there are multiple the same symbols indicating the type or number of groups, unless otherwise specified, a plurality of the same The contents of the symbols are independent, and the contents of the same symbols may be the same or different.
In this specification, when a plurality of groups of the same type (such as an alkyl group) are present in one formula (general formula) representing a chemical structure, unless otherwise specified, The specific contents are independent of each other, and the specific contents of groups of the same type may be the same or different.

The bonding direction of the divalent groups (eg, --CO--O--) described herein is not limited unless otherwise specified. For example, when Y is -CO-O- in a compound represented by the general formula "X-Y-Z", the compound may be "X-O-CO-Z". —CO—O—Z”.

[Photoelectric conversion element]
The photoelectric conversion element of the present invention is a photoelectric conversion element having a conductive film, a photoelectric conversion film and a transparent conductive film in this order, wherein the photoelectric conversion film is a compound represented by formula (1) (hereinafter, " Also referred to as "specific compounds").
A feature of the present invention is that it contains a specific compound.
The present inventor speculates that the particular compound has a group represented by formula (1A), and therefore has excellent photoelectric conversion efficiency for green light and red light in the visible light region. In addition, it is considered that the production aptitude is also excellent due to the influence of the overall structure and overall physical properties (for example, molecular weight, etc.) of the specific compound.
Hereinafter, when at least one of the photoelectric conversion efficiency and manufacturability with respect to a specific wavelength is more excellent, it is also referred to as "the effect of the present invention is more excellent".

FIG. 1 shows a schematic cross-sectional view of one embodiment of the photoelectric conversion element of the present invention.
A photoelectric conversion element 10a shown in FIG. 1 includes a conductive film (hereinafter also referred to as a “lower electrode”) 11 functioning as a lower electrode, an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and an upper electrode. A transparent conductive film (hereinafter, also referred to as an “upper electrode”) 15 that functions as an electrode is laminated in this order.
FIG. 2 shows a configuration example of another photoelectric conversion element. The photoelectric conversion element 10b shown in FIG. 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 on a lower electrode 11 in this order. 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 appropriately changed according to the application and characteristics.

In the photoelectric conversion element 10 a (or 10 b ), light is preferably incident on the photoelectric conversion film 12 via the upper electrode 15 .
Moreover, 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. From the viewpoint of performance and power consumption, the applied voltage is more preferably 1×10 ⁻⁴ to 1×10 ⁷ V/cm, further preferably 1×10 ⁻³ to 5×10 ⁶ V/cm.
1 and 2, it is preferable to apply the voltage so that the electron blocking film 16A side becomes the cathode and the photoelectric conversion film 12 side becomes the anode. When the photoelectric conversion element 10a (or 10b) is used as an optical sensor, or incorporated in an imaging device, a voltage can be applied by a similar method.
As will be described later in detail, the photoelectric conversion element 10a (or 10b) is suitable for use as an imaging element.
The form of each layer constituting the photoelectric conversion element of the present invention will be described in detail below.

[Photoelectric conversion film]
A photoelectric conversion element has a photoelectric conversion film.

<Specific compound>
A photoelectric conversion film contains a specific compound as a photoelectric conversion material.
A specific compound is a compound represented by Formula (1).

For geometric isomers that can be distinguished based on the C═C double bond consisting of the carbon atom to which R ¹ is attached to a particular compound in formula (1) and the carbon atoms adjacent thereto, formula (1) Including both. In other words, both the cis isomer and the trans isomer, which are distinguished based on the C=C double bond, are included in the compound represented by formula (1).

In formula ( ¹ ), A1 represents a group represented by formula (1A). D ¹ represents a substituent having an aromatic ring. R ¹ represents a hydrogen atom or a substituent.

R ¹ represents a hydrogen atom or a substituent.
Examples of the substituent include groups exemplified for the substituent W.
R ¹ is preferably a hydrogen atom.

A ¹ represents a group represented by formula (1A).
A ¹ is preferably a group represented by formula (2A) or a group represented by formula (3A).

In formula (1A), * represents a binding position. Y ^a11 represents an oxygen atom, a sulfur atom, =NR ^Y11 or =CR ^Y12 R ^Y13 . ^RY11 represents a hydrogen atom or a substituent. R ^Y12 and R ^Y13 each independently represent a cyano group or —COOR ^Y14 . ^RY14 represents an optionally substituted alkyl group or an optionally substituted aromatic ring group. X ^a11 and X ^a12 each independently represent a nitrogen atom or =C<. A bond represented by a solid line and a dotted line between ^Xa11 and ^Xa12 represents a single bond or a double bond. However, when the bond between X ^a11 and X ^a12 represents a double bond, X ^a11 and X ^a12 represent =C<. When the bond between X ^a11 and X ^a12 represents a single bond, one of X ^a11 and X ^a12 represents a nitrogen atom and the other represents a nitrogen atom or =C<. Ar ^a11 represents a ring containing X ^a11 and X ^a12 . The ring represented by Ar ^a11 may further have a substituent. X ^a13 represents a nitrogen atom or —CR ^X11 =. R ^X11 represents a hydrogen atom or a substituent.

Y ^a11 represents an oxygen atom, a sulfur atom, =NR ^Y11 or =CR ^Y12 R ^Y13 .
^RY11 represents a hydrogen atom or a substituent. R ^Y12 and R ^Y13 each independently represent a cyano group or —COOR ^Y14 . ^RY14 represents an optionally substituted alkyl group or an optionally substituted aromatic ring group.
Y ^a11 is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.
Examples of the optionally substituted aromatic ring group represented by R ^Y14 include an optionally substituted aryl group and an optionally substituted heteroaryl group. .
The substituent represented by R ^Y11 , the substituent which the aromatic ring group represented by R ^Y14 may have, and the substituent which the alkyl group represented by R ^Y14 may have include: For example, groups exemplified for the substituent W can be mentioned.

X ^a11 and X ^a12 each independently represent a nitrogen atom or =C<. The bonds of ^Xa11 and ^Xa12 represented by solid lines and dotted lines represent single bonds or double bonds. However, when the bond between X ^a11 and X ^a12 represents a double bond, X ^a11 and X ^a12 represent =C<. When the bond between X ^a11 and X ^a12 represents a single bond, one of X ^a11 and X ^a12 represents a nitrogen atom and the other represents a nitrogen atom or =C<.
At least one of X ^a11 and X ^a12 preferably represents =C<.
Specifically, aspects of portions corresponding to X ^a11 and X ^a12 in formulas (1A-1) to (1A-4) described below are mentioned.

X ^a13 represents a nitrogen atom or —CR ^X11 =. R ^X11 represents a hydrogen atom or a substituent.
X ^a13 is preferably —CR ^X11 =.
Examples of the substituent represented by R ^X11 include groups exemplified for the substituent W, a halogen atom (preferably a fluorine atom), an alkyl group, or an alkyl group having a halogen atom (preferably a fluorine atom) An alkyl group having 1 to 3 carbon atoms or an alkyl group having 1 to 3 carbon atoms having a fluorine atom is more preferable. The alkyl group may be linear, branched or cyclic, preferably linear.

Ar ^a11 represents a ring containing X ^a11 and X ^a12 . The ring represented by Ar ^a11 may further have a substituent.
Ar ^a11 is a ring containing X ^a11 and X ^a12 . In other words, the ring represented by Ar ^a11 includes X ^a11 and X ^a12 as ring member atoms.
Examples of the substituent that the ring represented by Ar ^a11 may have include groups exemplified for the substituent W, an alkyl group optionally having a substituent, a halogen atom or a cyano groups are preferred. The alkyl group may be linear, branched or cyclic, preferably linear.
Ar ^a11 may be either monocyclic or polycyclic, preferably monocyclic. The polycyclic ring may be a condensed ring.
Ar ^a11 preferably has 2 to 20 carbon atoms, more preferably 2 to 5 carbon atoms.
Ar ^a11 may have a heteroatom as a ring member atom. Examples of the heteroatom include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom and boron atom, with nitrogen atom being preferred.
Ar ^a11 may be either aromatic or non-aromatic, preferably aromatic.
Ar ^a11 preferably contains a 5- or 6-membered ring, more preferably a 5-membered ring, and even more preferably a 5-membered ring (monocyclic 5-membered ring).

Ar ^a11 includes, for example, an aromatic ring such as an aromatic hydrocarbon ring and an aromatic heterocyclic ring, and a non-aromatic ring, preferably an aromatic ring, more preferably an aromatic heterocyclic ring.
Ar ^a11 includes, for example, aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring and phenanthrene ring; pyrrole ring, pyrazole ring, triazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, thiophene ring; Aromatic heterocycles such as furan ring, pyran ring, thiazole ring, oxazole ring, selenophene ring, imidazole ring, benzofuran ring, benzothiophene ring, benzotriazole ring and benzoxazole ring; cycloalkane ring, pyrrolidine ring, pyrroline ring, imidazo Non-aromatic rings such as lysine ring and tetrafuran ring are included.

Examples of the group represented by formula (1A) include groups represented by any one of formulas (1A-1) to (1A-4).

In formulas (1A-1) to (1A-4), each notation is as described above.

In formula (2A), * represents a binding position. R ^a21 represents a hydrogen atom or a substituent. X ^a21 to X ^a23 each independently represent a nitrogen atom or —CR ^X21 =. R ^X21 represents a hydrogen atom or a substituent.

R ^a21 is the same as R ^X11 above, and the preferred embodiments are also the same.

X ^a21 to X ^a23 each independently represent a nitrogen atom or —CR ^X21 =. R ^X21 represents a hydrogen atom or a substituent.
Examples of the substituent represented by R ^X21 include groups exemplified for the substituent W.
R ^X21 is preferably a hydrogen atom.
At least one of X ^a21 to X ^a23 preferably represents —CR ^X21 =, and more preferably all of X ^a21 to X ^a23 represent —CR ^X21 =.

In formula (3A), * represents a binding position. R ^a31 and R ^a32 each independently represent a hydrogen atom or a substituent. X ^a31 and X ^a32 each independently represent a nitrogen atom or —CR ^X22 =. R ^X22 represents a hydrogen atom or a substituent.

R ^a31 is the same as R ^X11 above, and the preferred embodiments are also the same.
Examples of the substituent represented by R ^a32 include groups exemplified for the substituent W, preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms. The alkyl group may be linear, branched or cyclic, preferably linear.

X ^a31 and X ^a32 each independently represent a nitrogen atom or —CR ^X22 =. R ^X22 represents a hydrogen atom or a substituent.
R ^X22 is the same as R ^X21 above, and the preferred embodiments are also the same.
One of X ^a31 and X ^a32 preferably represents a nitrogen atom and the other preferably represents —CR ^X22 =.

D ¹ represents a substituent having an aromatic ring.
A substituent having an aromatic ring means that a part or all of the substituent has an aromatic ring. That is, the substituent having an aromatic ring may be a group having an aromatic ring and a substituent or an aromatic ring group having only an aromatic ring.
D ¹ is preferably an optionally substituted aryl group or an optionally substituted heteroaryl group, more preferably an optionally substituted heteroaryl group. Examples of the substituents that the aryl group and the heteroaryl group may have include groups exemplified for the substituent W, and optionally substituted aryl groups (preferably alkyl groups ) or a heteroaryl group optionally having a substituent (preferably a heteroaryl group optionally having an alkyl group).

D ¹ may be either monocyclic or polycyclic. The polycyclic ring may be a condensed ring.
The number of ring members of the aromatic ring of D ¹ is preferably 5-40, more preferably 10-30, even more preferably 20-30.
Aromatic rings include, for example, aromatic hydrocarbon rings, aromatic heterocyclic rings, and rings in which these are combined.
Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene and combinations thereof.
Examples of aromatic heterocyclic rings include thiophene ring, furan ring, pyran ring, thiazole ring, pyrrole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, oxazole ring, selenophene ring, imidazole ring, quinoxaline ring, and benzothiazole ring. Rings and rings in which these are combined are included.
D ¹ may have other rings in addition to the above aromatic ring. Other rings may be condensed with the aromatic ring to form a condensed ring.
Examples of the other rings include cycloalkane rings, piperidine rings, piperazine rings, imidazolidine rings, and rings in which these are combined.

D ¹ is preferably a group represented by any one of formulas (1D) to (3D), more preferably a group represented by formula (1D), and even more preferably a group represented by formula (4D). , a group of formula (5D) is particularly preferred, and a group of formula (6D) is most preferred.

In formula (1D), * represents a binding position. Ar ^d11 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d11 may further have a substituent. R ^d11 and R ^d12 each independently represent —C(R ^L11 ) (R ^L12 ) (R ^L13 ) or an optionally substituted aromatic ring group. R ^L11 to R ^L13 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L11 to R ^L13 may combine with each other to form a ring. R ^d13 represents a hydrogen atom or a substituent.

Ar ^d11 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d11 may further have a substituent.
Ar ^d11 is preferably an aromatic heterocyclic ring, more preferably a quinoxaline ring or a pyrazine ring.
The substituents possessed by the aromatic ring represented by Ar ^d11 include, for example, groups exemplified for the substituent W, an optionally substituted alkyl group, a chlorine atom, a fluorine atom or a cyano group. preferable.

R ^d11 and R ^d12 each independently represent —C(R ^L11 ) (R ^L12 ) (R ^L13 ) or an optionally substituted aromatic ring group.
The optionally substituted aromatic ring group represented by R ^d11 and R ^d12 is preferably an optionally substituted aryl group or an optionally substituted heteroaryl group. , an optionally substituted aryl group is more preferable.

The aryl group which may have a substituent is preferably a phenyl group, a naphthyl group or a fluorenyl group which may have a substituent, and a phenyl group or a substituent which may have a substituent. An optional naphthyl group is more preferred.
When the aryl group optionally having substituents is a phenyl group optionally having substituents, the phenyl group preferably has a substituent. The above substituents are each independently preferably an alkyl group (preferably having 1 to 3 carbon atoms).
When the aryl group optionally having substituents is a phenyl group optionally having substituents, the number of substituents the phenyl group has is preferably 1 to 5, more preferably 2 or 3. .

R ^L11 to R ^L13 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group.
The optionally substituted aromatic ring group represented by R ^L11 to R ^L13 is preferably an optionally substituted aryl group or an optionally substituted heteroaryl group. .
At least two of R ^L11 to R ^L13 are each independently an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted hetero group. It preferably represents an aryl group.
The alkyl group optionally having substituents, the aryl group optionally having substituents and the heteroaryl group optionally having substituents represented by R ^L11 to R ^L13 are bonded to each other. may form a ring.
For example, optionally substituted alkyl groups may bond together to form a ring. A substituent in the aryl group which may have a substituent and an alkyl group which may have a substituent may combine with each other to form a ring. A substituent in the heteroaryl group which may have a substituent and an alkyl group which may have a substituent may combine with each other to form a ring. A substituent in an aryl group which may have a substituent and a substituent in another aryl group which may have a substituent may combine with each other to form a ring. A substituent in the aryl group which may have a substituent and a substituent in the heteroaryl group which may have a substituent may combine with each other to form a ring. A substituent in an optionally substituted heteroaryl group and a substituent in another optionally substituted heteroaryl group may be combined to form a ring.
A substituent of the ring thus formed, another alkyl group optionally having a substituent, a substituent in another aryl group optionally having a substituent, or a substituent A substituent of another heteroaryl group which may be present may be combined to further form a ring.
In addition, as described above, a substituent and a substituent (for example, a substituent in an aryl group which may have a substituent and a substituent in a heteroaryl group which may have a substituent) are bonded to each other. The group formed by combining may be a single bond.
An optionally substituted alkyl group represented by R ^L11 to R ^L13 , an optionally substituted aromatic ring group (preferably an optionally substituted aryl group or optionally substituted heteroaryl group) are bonded to each other to form a ring, and —C(R ^L11 )(R ^L12 )(R ^L13 ) is a group other than an aryl group and a heteroaryl group preferable.

The alkyl groups represented by R ^L11 to R ^L13 may each independently be linear, branched or cyclic. In the alkyl groups represented by R ^L11 to R ^L13 , two alkyl groups are preferably bonded to each other to form a ring.
More specifically, the alkyl group represented by ^{RL11 and the alkyl group represented by RL12 may} combine with each other to form a ring. Further, a substituent of a ring formed by bonding an alkyl group represented by R ^L11 and an alkyl group represented by R ^L12 (for example, a monocyclic cycloalkane ring) and a substituent represented by R ^L13 may be bonded to each other to form a polycyclic ring (for example, a polycyclic cycloalkane ring, etc.).
That is, —C(R ^L11 )(R ^L12 )(R ^L13 ) may be an optionally substituted cycloalkyl group (preferably a cyclohexyl group). The number of ring members of the cycloalkyl group is preferably 3 to 12, more preferably 5 to 8, and even more preferably 6.
The cycloalkyl group may be monocyclic (eg, cyclohexyl group, etc.) or polycyclic (eg, 1-adamantyl group, etc.).
The cycloalkyl group preferably has a substituent. When the cycloalkyl group has a substituent, the carbon atom directly bonded to the nitrogen atom specified in formula (1D) (that is, specified in "-C (R ^L11 ) (R ^L12 ) (R ^L13 )" It is preferred that the carbon atoms adjacent to the "C" atom where the group is substituted) have substituents.
Examples of the substituent that the cycloalkyl group may have include an alkyl group (preferably having 1 to 3 carbon atoms).
The substituents of the cycloalkyl group may be bonded to each other to form a ring, and the ring formed by the substituents to be bonded to each other may be a ring other than a cycloalkane ring.

R ^d11 and R ^d12 are each independently a group represented by formula (X), —C(R ^L11 )(R ^L12 )(R ^L13 ), an optionally substituted polycyclic aryl group or an optionally substituted polycyclic heteroaryl group.
R ^d11 and R ^d12 are each independently a group represented by formula (X), —C(R ^L11 ) (R ^L12 ) (R ^L13 ), from the viewpoint of better suitability for manufacturing the photoelectric conversion element of the present invention. or an optionally substituted polycyclic aryl group is preferred. The group represented by formula (X) is preferably a group represented by formula (Z) described below, and more preferably a group represented by formula (ZB) described below.

In formula (X), C ¹ represents a monocyclic aromatic ring optionally having a substituent other than R ^d1 . R ^d1 represents an alkyl group, silyl group, alkoxy group, alkylthio group, cyano group, halogen atom, aryl group, heteroaryl group, alkenyl group or alkynyl group. These groups may further have a substituent if possible. * represents a binding position.

C ¹ represents a monocyclic aromatic ring optionally having a substituent other than R ^d1 .
Examples of the monocyclic aromatic ring include a monocyclic aromatic hydrocarbon ring and a monocyclic aromatic heterocyclic ring. Aromatic hydrocarbon rings include, for example, benzene rings. Aromatic heterocycles include, for example, pyrrole, furan, thiophene, imidazole and oxazole rings.
The monocyclic aromatic ring is preferably an aromatic hydrocarbon ring, and more preferably a benzene ring, from the viewpoint that the photoelectric conversion element has better heat resistance.

R ^d1 represents an alkyl group, silyl group, alkoxy group, alkylthio group, cyano group, halogen atom, aryl group, heteroaryl group, alkenyl group or alkynyl group. These groups may further have a substituent if possible.
The number of carbon atoms in the alkyl group represented by R ^d1 is preferably 1-12, more preferably 1-6, and even more preferably 1-3.
The silyl group represented by R ^d1 preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and more preferably 3 carbon atoms.
The number of carbon atoms in the alkoxy group represented by R ^d1 is preferably 1-12, more preferably 1-6, and even more preferably 1-3.
The number of carbon atoms in the alkylthio group represented by R ^d1 is preferably 1-12, more preferably 1-6, even more preferably 1-3.
Halogen atoms represented by R ^d1 include, for example, a fluorine atom, an iodine atom, a bromine atom and a chlorine atom.
The alkenyl group represented by R ^d1 preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and still more preferably 2 to 3 carbon atoms.
The alkynyl group represented by R ^d1 preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and still more preferably 2 to 3 carbon atoms.

The substituents of R ^d1 and C ¹ may combine with each other to form a non-aromatic ring.
The aromatic ring of C ¹ is directly attached to the nitrogen atom specified in formula (1D).

In formula (Z), T ¹ to T ⁴ each independently represent -CR ^e12 = or a nitrogen atom (=N-). R ^e12 represents a hydrogen atom or a substituent.

It is preferable that "at least one of T ¹ to T ⁴ represents -CR ^e12 = and at least one of R ^e12 represents a substituent", and "at least T ⁴ represents -CR ^e12 = and T ^{4 Re12} in represents an alkyl group, an aryl group or a heteroaryl group" is more preferable.
The substituent represented by R ^e12 is preferably an alkyl group, an aryl group, a heteroaryl group, a silyl group, a halogen atom or a cyano group. These groups may further have a substituent (for example, a halogen atom such as a fluorine atom).
The number of carbon atoms in the alkyl group represented by R ^e12 is preferably 1-12, more preferably 1-6, even more preferably 1-3.
Examples of the silyl group represented by R ^e12 include the silyl groups described as the silyl group represented by R ^d1 .
Halogen atoms represented by R ^e12 include, for example, a fluorine atom, an iodine atom, a bromine atom and a chlorine atom.
In addition, when a plurality of R ^e12 are present in the formula (Z), the R ^e12 may be the same or different.

In formula (Z), R ^f2 represents an alkyl group, silyl group, alkoxy group, alkylthio group, cyano group, halogen atom, aryl group, heteroaryl group, alkenyl group or alkynyl group. It has the same meaning as R ^d1 in Formula (X), and the preferred embodiments are also the same.
R ^f2 and R ^e12 in T ¹ may combine with each other to form a non-aromatic ring.
The number of carbon atoms in the alkyl group represented by R ^f2 is preferably 1-12, more preferably 1-6, even more preferably 1-3.

In formula (ZB), T ¹ to T ³ each independently represent —CR ^e12 = or a nitrogen atom. R ^e12 represents a hydrogen atom or a substituent.
R ^e12 in formula (ZB) is the same as R ^e12 in formula (Z).

In formula (ZB), R ^f3 and R ^f4 each independently represent an alkyl group, an aryl group, or a heteroaryl group. These groups may further have a substituent if possible. * represents a binding position.
The number of carbon atoms in the alkyl group represented by R ^f3 and R ^f4 is preferably 1-12, more preferably 1-6, and still more preferably 1-3.

The number of rings constituting the optionally substituted polycyclic aryl group and the optionally substituted polycyclic heteroaryl group is 2 or more, preferably 2 to 4, and 2 to 3 is more preferred, and 2 is even more preferred.
The optionally substituted polycyclic aryl group and the optionally substituted polycyclic heteroaryl group may have a non-aromatic ring. .
As the optionally substituted polycyclic aryl group, for example, an optionally substituted naphthyl group is preferable.

R ^d13 represents a hydrogen atom or a substituent.
Examples of the substituent represented by R ^d13 include groups exemplified for the substituent W.
R ^d13 is preferably a hydrogen atom.

In formula (2D), * represents a binding position. Ar ^d21 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d21 may further have a substituent. Z ^d21 represents a chalcogen atom or -NR ^Z21 -. R ^Z21 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. Z ^d22 represents a nitrogen atom or -CR ^Z22 =. R ^Z22 represents a hydrogen atom or a substituent.

Ar ^d21 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d21 may further have a substituent.
Ar ^d21 includes, for example, an aromatic ring represented by Ar ^d11 , preferably an aromatic heterocyclic ring.
Examples of the substituent that the aromatic ring represented by Ar ^d21 may have include groups exemplified for the substituent W, and an alkyl group or an aryl group is preferable.
Ar ^d21 may be either monocyclic or polycyclic. The polycyclic ring may be a condensed ring.
The number of ring members of the aromatic ring represented by Ar ^d21 is preferably 5-6, more preferably 5.
Examples of the aromatic heterocyclic ring include a quinoxaline ring, a pyrazine ring, a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, and rings in which these are combined. A ring is preferred.

Z ^d21 represents a chalcogen atom or -NR ^Z21 -. R ^Z21 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group.
The chalcogen atom includes, for example, an oxygen atom, a sulfur atom, a selenium atom and a tellurium atom, preferably an oxygen atom or a sulfur atom.
R ^Z21 is preferably an optionally substituted alkyl group or an optionally substituted aryl group, more preferably an optionally substituted alkyl group, unsubstituted alkyl groups are more preferred. Examples of the substituent include groups exemplified for the substituent W, and an alkyl group is preferable.
Z ^d21 is preferably -NR ^Z21 -.

Z ^d22 represents a nitrogen atom or -CR ^Z22 =. R ^Z22 represents a hydrogen atom or a substituent.
Examples of the substituent include groups exemplified for the substituent W, and an alkyl group is preferable.
R ^Z22 is preferably a hydrogen atom.

In formula (3D), * represents a binding position. Ar ^d31 and Ar ^d32 each independently represent an aromatic ring containing two or more carbon atoms. The aromatic rings represented by Ar ^d31 and Ar ^d32 may further have a substituent. Z ^d31 represents -CR ^Z31 R ^Z32 -, -SiR ^Z31 R ^Z32 - or >C=R ^Z33 . R ^Z31 and R ^Z32 each independently represent a hydrogen atom or a substituent. R 2 ^Z31 and R 2 ^Z32 may combine with each other to form a ring. R ^Z33 represents an oxygen atom, a sulfur atom or =CR ^Z34 R ^Z35 . R ^Z34 and R ^Z35 each independently represent a hydrogen atom or a substituent. At least one of R ^Z34 and R ^Z35 and at least one of Ar ^d31 and Ar ^d32 may be condensed with each other to form a condensed ring. R ^d31 represents a hydrogen atom or a substituent.

Ar ^d31 and Ar ^d32 each independently represent an aromatic ring containing two or more carbon atoms. The aromatic rings represented by Ar ^d31 and Ar ^d32 may further have a substituent.
The above aromatic ring may be either monocyclic or polycyclic. The polycyclic ring may be a condensed ring.
One of Ar ^d31 and Ar ^d32 is preferably monocyclic and the other is polycyclic, more preferably Ar ^d31 is monocyclic and Ar ^d32 is polycyclic, Ar ^d31 is a benzene ring and Ar More preferably, ^d32 is a naphthalene ring.
The number of ring members of the monocyclic ring is preferably 5-12, more preferably 5-6.
The total number of ring members of the polycyclic ring is preferably 10 or more, more preferably 12 or more. The upper limit is often 20 or less.
The number of carbon atoms in the aromatic rings represented by Ar ^d31 and Ar ^d32 is each independently 2 or more, preferably 6 or more. The upper limit is often 20 or less, preferably 12 or less.
Examples of the substituent that the aromatic rings represented by Ar ^d31 and Ar ^d32 may have include groups exemplified for the substituent W, and an alkyl group is preferable.
The aromatic rings represented by Ar ^d31 and Ar ^d32 also preferably have no substituents.
Examples of the aromatic rings represented by Ar ^d31 and Ar ^d32 include aromatic hydrocarbon rings and aromatic heterocycles represented by Ar ^a11 .
The aromatic ring is preferably an aromatic hydrocarbon ring, more preferably a benzene ring or a naphthalene ring.

Z ^d31 represents -CR ^Z31 R ^Z32 -, -SiR ^Z31 R ^Z32 - or >C=R ^Z33 . R ^Z31 and R ^Z32 each independently represent a hydrogen atom or a substituent. R 2 ^Z31 and R 2 ^Z32 may combine with each other to form a ring.
Z ^d31 is preferably -CR ^Z31 R ^Z32 -.
Examples of the substituents represented by R 2 ^Z31 and R 2 ^Z32 include groups exemplified for the substituent W, and alkyl groups (preferably alkyl groups having 1 to 3 carbon atoms) are preferred. The alkyl group may be linear, branched or cyclic, preferably linear.

R ^Z33 represents an oxygen atom, a sulfur atom or =CR ^Z34 R ^Z35 ; R ^Z34 and R ^Z35 each independently represent a hydrogen atom or a substituent.
Examples of substituents represented by R 2 ^Z34 and R 2 ^Z35 include groups exemplified for substituent W.

At least one of R ^Z34 and R ^Z35 and at least one of Ar ^d31 and Ar ^d32 may be condensed with each other to form a condensed ring.
Specifically, Ar ^d31 and R ^Z34 or R ^Z35 , Ar ^d32 and R ^Z34 or R ^Z35 , and Ar ^d31 , Ar ^d32 , R ^Z34 and R ^Z35 are condensed with each other to form condensed rings. may

In formula (4D), * represents a binding position. R ^d41 and R ^d42 each independently represent —C(R ^L41 ) (R ^L42 ) (R ^L43 ) or an optionally substituted aromatic ring group. R ^L41 to R ^L43 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L41 to R ^L43 may combine with each other to form a ring. R ^d43 represents a hydrogen atom or a substituent. E ^d41 to E ^d44 each independently represent a nitrogen atom or —CR ^E41 =. R ^E41 represents a hydrogen atom or a substituent. When multiple R ^E41 are present, the multiple R ^E41 may be bonded to each other to form a ring.

R ^d41 and R ^d42 each independently represent —C(R ^L41 ) (R ^L42 ) (R ^L43 ) or an optionally substituted aromatic ring group.
R ^d41 and R ^d42 are the same as R ^d11 and R ^d12 above, and the preferred embodiments are also the same.
R ^d43 represents a hydrogen atom or a substituent.
R ^d43 is the same as R ^d13 above, and the preferred embodiments are also the same.

E ^d41 to E ^d44 each independently represent a nitrogen atom or —CR ^E41 =. R ^E41 represents a hydrogen atom or a substituent. When multiple R ^E41 are present, the multiple R ^E41 may be bonded to each other to form a ring.
At least two of E ^d41 to E ^d44 are preferably nitrogen atoms, more preferably at least E ^d41 and E ^d44 are nitrogen atoms, and even more preferably only E ^d41 and E ^d44 are nitrogen atoms.
The ring formed by combining a plurality of ^RE41s is preferably an aromatic ring, more preferably a benzene ring or a pyridine ring. The ring formed above may further have a substituent (eg, a group exemplified for the substituent W).

In formula (5D), * represents a binding position. R ^d51 and R ^d52 each independently represent —C(R ^L51 ) (R ^L52 ) (R ^L53 ) or an optionally substituted aromatic ring group. R ^L51 to R ^L53 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L51 to R ^L53 may combine with each other to form a ring. R ^d53 to R ^d55 each independently represent a hydrogen atom or a substituent. R ^d54 and R ^d55 may combine with each other to form a ring.

R ^d51 and R ^d52 are the same as R ^d11 and R ^d12 above, and the preferred embodiments are also the same.
R ^d53 to R ^d55 each independently represent a hydrogen atom or a substituent.
R ^d53 is the same as R ^d13 above, and the preferred embodiments are also the same.
Examples of substituents represented by R ^d54 and R ^d55 include groups exemplified for substituent W, and alkyl groups are preferred.
The ring formed by combining R ^d54 and R ^d55 is preferably an aromatic ring, more preferably a benzene ring. The ring formed above may further have a substituent (eg, a group exemplified for the substituent W).

In formula (6D), * represents a binding position. R ^d61 and R ^d62 each independently represent —C(R ^L61 ) (R ^L62 ) (R ^L63 ) or an optionally substituted aromatic ring group. R ^L61 to R ^L63 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L61 to R ^L63 may combine with each other to form a ring. R ^d63 to R ^d65 each independently represent a hydrogen atom or a substituent. R ^d64 and R ^d65 may combine with each other to form a ring. E ^d61 and E ^d62 each independently represent a nitrogen atom or -CR ^E61 =. R ^E61 represents a hydrogen atom or a substituent.

R ^d61 and R ^d62 are the same as R ^d41 and R ^d42 above, and the preferred embodiments are also the same.
R ^d63 to R ^d65 each independently represent a hydrogen atom or a substituent.
R ^d63 is the same as R ^d13 above, and the preferred embodiments are also the same.
Examples of substituents represented by R ^d64 and R ^d65 include groups exemplified for substituent W.
R ^d64 and R ^d65 are preferably a hydrogen atom, a halogen atom or a cyano group.

E ^d61 and E ^d62 each independently represent a nitrogen atom or -CR ^E61 =. R ^E61 represents a hydrogen atom or a substituent.
One of E ^d61 and E ^d62 preferably represents -CR ^E61 = and the other preferably represents a nitrogen atom or -CR ^E61 =, and preferably E ^d61 and E ^d62 represent -CR ^E61 =.
Examples of the substituent represented by R ^E61 include groups exemplified for the substituent W.

Preferred aspects of the specific compound include, for example, the following aspects.
As preferred embodiments of the specific compound, Aspect A is preferred, Aspect B is more preferred, Aspect C is still more preferred, and Aspect D is particularly preferred.
Aspect A: D ¹ is a substituent containing an aromatic ring, and A ¹ is a group represented by formula (2A).
Mode B: D ¹ is a group represented by any one of formulas (1D) to (3D), and A ¹ is a group represented by formula (2A) or a group represented by formula (3A) .
Mode C: D ¹ is a group represented by formula (5D), and A ¹ is a group represented by formula (2A) or a group represented by formula (3A).
Mode D: D ¹ is a group represented by formula (6D), and A ¹ is a group represented by formula (2A) or a group represented by formula (3A).

Specific compounds are exemplified below.
In addition, when the specific compounds exemplified below are applied to formula ( ¹ ), the geometric With respect to isomers, the specific compounds exemplified below include both. That is, both the cis isomer and the trans isomer, which are distinguished based on the C=C double bond, are included in the specific compounds exemplified below.

Although the molecular weight of the specific compound is not particularly limited, it is preferably from 400 to 1200, more preferably from 400 to 1000, and even more preferably from 400 to 800, from the viewpoint of excellent production aptitude.
In the case of the above molecular weight, the sublimation temperature of the specific compound is low, and it is presumed that the photoelectric conversion efficiency is excellent even when the photoelectric conversion film is formed at high speed.

The specific compound is particularly useful as a material for photoelectric conversion films used in imaging devices, optical sensors, or photoelectric cells. In addition, the specific compound often functions as a p-type organic semiconductor in the photoelectric conversion film. The specific compound can also be used as a coloring material, a liquid crystal material, an organic semiconductor material, a charge transport material, a pharmaceutical material, and a fluorescent diagnostic agent material.

The specific compound is a compound having 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 preferably

The maximum absorption wavelength of the specific compound is preferably in the range of 500-600 nm, more preferably in the range of 530-580 nm.
The maximum absorption wavelength is a value measured in the state of a film of a specific compound (for example, a vapor-deposited film of a specific compound).

A particular compound may be purified if desired.
Although the method for purifying the specific compound is not particularly limited, sublimation purification is preferred.
The purity of the specific compound after sublimation purification (for example, purity measured by HPLC or GC) is not particularly limited, but is preferably 95% or higher, more preferably 98% or higher, and even more preferably 99% or higher.

Prior to sublimation purification of the specific compound, the specific compound may be purified by other methods. For example, for the specific compound, purification using silica gel column chromatography, purification using GPC (GEL Permeation CHROMATOGRAPHY). , reslurry washing, reprecipitation purification, purification using an adsorbent such as activated carbon, and recrystallization purification are preferably performed.
The purity of the specific compound before sublimation purification (for example, purity measured by HPLC or GC) is not particularly limited, but is preferably 95% or higher, more preferably 98% or higher, and even more preferably 99% or higher.
The solvent (recrystallization solvent) used during recrystallization purification is not particularly limited, but examples include methanol, ethanol, isopropanol, butanol, toluene, xylene, anisole, 1,2-dimethoxybenzene, tetralin, chlorobenzene, and dichlorobenzene. , hexane, heptane, octane, acetonitrile, benzonitrile, acetic acid, chloroform, dichloromethane, ethyl acetate, butyl acetate, tetrahydrofuran, 4-methyltetrahydropyran, and cyclopentyl methyl ether.
The recrystallization solvent may be a mixture of multiple solvents.

The amount of residual solvent contained in the crude material containing the specific compound to be subjected to sublimation purification is not particularly limited, but the amount of residual solvent is preferably 10 mol% or less, and 5 mol% or less based on the total molar amount of the specific compound in the crude material. is more preferable, and 2 mol % or less is even more preferable.

Elements (for example, Li, Na, K, Mg, Ca, Al, Si, P, Sn, transition metal elements, etc.) that do not constitute the specific compound contained in the crude body containing the specific compound to be subjected to sublimation purification Impurities included are not particularly limited, but are preferably 1000 mass ppm or less, more preferably 100 mass ppm or less, and still more preferably 10 mass ppm or less, relative to the total mass of the crude product.
Methods for measuring the above elements include ICP (Inductively Coupled Plasma) emission spectrometry.

A specific compound can be synthesized by a known method.
In order to improve the purity of the specific compound, the purity of the raw materials used in the synthesis of the specific compound including intermediates (for example, the purity measured by HPLC or GC) is not particularly limited, but is preferably 97% or more, and 98% or more. More preferably, 99% or more is even more preferable.
When the purity of commercially available raw materials and synthetic intermediates is low, those purified by known methods may be used.

You may use a specific compound individually by 1 type or in 2 or more types.
The content of the specific compound in the photoelectric conversion film (=thickness of the specific compound in terms of a single layer/thickness of the photoelectric conversion film×100) is preferably 15 to 75% by volume, more preferably 20 to 60% by volume. , 25 to 50% by volume is more preferred.

<n-type organic semiconductor>
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), and refers to an organic compound having a property of easily accepting electrons. That is, the n-type organic semiconductor refers to an organic compound having 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 is an organic compound having an electron-accepting property.
Examples of n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof, condensed aromatic carbocyclic compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives and fluoranthene derivatives, etc.); 5- to 7-membered heterocyclic compounds having at least one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline) , quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole and thiazole, etc.); polyarylene compounds; fluorene compounds; cyclopentadiene compounds; silyl compounds; Tetracarboxylic anhydrides; 1,4,5,8-naphthalenetetracarboxylic anhydride imide derivatives and oxadiazole derivatives; anthraquinodimethane derivatives; diphenylquinone derivatives; bathocuproine, bathophenanthroline and their derivatives; triazole compounds; metal complexes having a nitrogen-containing heterocyclic compound as a ligand; silole compounds; and compounds described in paragraphs [0056] to [0057] of JP-A-2006-100767.

As the n-type organic semiconductor (compound), fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred.
Fullerenes include, for example, fullerene C60, fullerene C70, fullerene C76, fullerene C78, fullerene C80, fullerene C82, fullerene C84, fullerene C90, fullerene C96, fullerene C240, fullerene C540 and mixed fullerene.
Fullerene derivatives include, for example, compounds in which substituents are added to the above fullerenes. The above substituent is preferably an alkyl group, an aryl group or a heterocyclic group. As the fullerene derivative, compounds described in JP-A-2007-123707 are preferred.

An organic dye may be used as the n-type organic semiconductor.
Examples of organic dyes include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squarium dyes, croconium dyes, Azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, Examples include acridine dyes, acridinone dyes, diphenylamine dyes, quinophthalone dyes, phenoxazine dyes, phthaloperylene dyes, dioxane dyes, porphyrin dyes, chlorophyll dyes, phthalocyanine dyes, subphthalocyanine dyes, and metal complex dyes.

The molecular weight of the n-type organic semiconductor is preferably 200-1200, more preferably 200-900.

It is also preferred that the n-type organic semiconductor is colorless or has an absorption maximum wavelength and/or absorption waveform close to that of a specific compound. As a specific numerical value, it is preferable that the maximum absorption wavelength of the n-type organic semiconductor is 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 the specific compound and the n-type organic semiconductor. A bulk heterostructure is a layer in which a specific compound and an n-type organic semiconductor are mixed and dispersed in a photoelectric conversion film. 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-A-2005-303266.

When the photoelectric conversion film contains an n-type organic semiconductor, the content of the n-type organic semiconductor in the photoelectric conversion film (=thickness of the n-type organic semiconductor in terms of a single layer/thickness of the photoelectric conversion film×100) is 15 to 75% by volume is preferred, 20 to 60% by volume is more preferred, and 25 to 50% by volume is even more preferred.
In addition, n-type semiconductor materials may be used individually by 1 type, and may be used 2 or more types.

In addition, when the n-type semiconductor material contains fullerenes, the content of fullerenes with respect to the total content of the n-type semiconductor material (= film thickness in terms of single layer of fullerenes / each n-type semiconductor in terms of single layer The total thickness of the material×100) is preferably 50 to 100% by volume, more preferably 80 to 100% by volume.
In addition, fullerenes may be used individually by 1 type, and may be used 2 or more types.

The difference in electron affinity between the specific compound and the n-type organic semiconductor is preferably 0.1 eV or more.

From the viewpoint of the responsiveness of the photoelectric conversion element, the content of the specific compound with respect to the total content of the specific compound and the n-type organic semiconductor (= film thickness in terms of a single layer of the specific compound / (in terms of a single layer of the specific compound The film thickness of the n-type organic semiconductor + the film thickness in terms of a single layer of the n-type organic semiconductor)×100) is preferably 20 to 80 volume %, more preferably 40 to 80 volume %.
Further, when the photoelectric conversion film contains a p-type organic semiconductor to be described later, the content of the specific compound (= film thickness of the specific compound in terms of a single layer / (thickness of the specific compound in terms of a single layer + n-type organic semiconductor The film thickness in terms of a single layer + the film thickness in terms of a single layer of the p-type organic semiconductor)×100) is preferably 15 to 75% by volume, more preferably 30 to 75% by volume.
The photoelectric conversion film is preferably substantially composed of a specific compound, an n-type organic semiconductor, and optionally a p-type organic semiconductor. Substantially means that the total content of the specific compound, the n-type organic semiconductor, and optionally the p-type organic semiconductor contained in the total mass of the photoelectric conversion film is 90 to 100% by volume (preferably 95 to 100 % by volume, more preferably 99-100% by volume).

<p-type organic semiconductor>
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), and refers to an organic compound having a property of easily donating electrons. In other words, the p-type organic semiconductor refers to an organic compound having a smaller ionization potential when two organic compounds are used in contact with each other.
The p-type organic semiconductor may be used singly or in combination of two or more.

Examples of p-type organic semiconductors include triarylamine compounds (eg, N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), compounds described in paragraphs [0128] to [0148] of JP-A-2011-228614, JP-A-2011-176259 The compounds described in paragraphs [0052] to [0063] of JP-A-2011-225544, the compounds described in paragraphs [0119] to [0158] of JP-A-2015-153910, [0044] to [ 0051] and compounds described in paragraphs [0086] to [0090] of JP-A-2012-94660), pyrazoline compounds, styrylamine compounds, hydrazone compounds, polysilane compounds, thiophene compounds (e.g., thienothiophene derivatives, dibenzothiophene derivatives, benzodithiophene derivatives, dithienothiophene derivatives, [1]benzothieno[3,2-b]thiophene (BTBT) derivatives, thieno[3,2-f:4,5-f′]bis[ 1] Benzothiophene (TBBT) derivatives, compounds described in paragraphs [0031] to [0036] of JP-A-2018-014474, compounds described in paragraphs [0043] to [0045] of WO2016-194630, WO2017-159684 The compounds described in paragraphs [0025] to [0037] and [0099] to [0109] of JP-A-2017-076766, the compounds described in paragraphs [0029] to [0034] of JP-A-2017-076766, the paragraph [ 0015] to [0025], compounds described in paragraphs [0045] to [0053] of JP-A-2019-054228, compounds described in paragraphs [0045] to [0055] of WO2019-058995, WO2019-081416 The compound described in paragraphs [0063] to [0089] of JP-A-2019-80052, the compound described in paragraphs [0033] to [0036], the compound described in paragraphs [0044] to [0054] of WO2019-054125, Compounds described in paragraphs [0041] to [0046] of WO2019-093188), paragraphs [0034] to [0037] of JP-A-2019-050398, paragraph [0033] of JP-A-2018-206878 - compound of [0036], JP-A-20 18-190755 paragraph [0038] compound, JP 2018-026559 paragraph [0019] ~ [0021] compound, JP 2018-170487 paragraph [0031] ~ [0056] compounds , Compounds of paragraphs [0036] to [0041] of JP-A-2018-078270, compounds of paragraphs [0055]-[0082] of JP-A-2018-166200, paragraph [0041 of JP-A-2018-113425 ] ~ [0050] compounds, compounds of paragraphs [0044] ~ [0048] of JP-A-2018-85430, compounds of paragraphs [0041] ~ [0045] of JP-A-2018-056546, JP 2018- Compounds of paragraphs [0042] to [0049] of JP-A-046267, compounds of paragraphs [0031] to [0036] of JP-A-2018-014474, paragraphs [0036] to [0046] of WO2018-016465 compound, paragraphs [0045] to [0048] of JP-A-2020-010024, etc.), cyanine compound, oxonol compound, polyamine compound, indole compound, pyrrole compound, pyrazole compound, polyarylene compound, condensed aromatic carbon Ring compounds (e.g., naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives, fluoranthene derivatives, etc.), porphyrin compounds, phthalocyanine compounds, triazole compounds, oxadiazole compounds, imidazole compounds, polyaryls Examples thereof include alkane compounds, pyrazolone compounds, amino-substituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having nitrogen-containing heterocyclic compounds as ligands.
Examples of the p-type organic semiconductor include compounds having a smaller ionization potential than that of the n-type organic semiconductor. If this condition is satisfied, the organic dyes exemplified as the n-type organic semiconductor can be used.
Compounds that can be used as the p-type semiconductor compound are exemplified below.

The difference in ionization potential between the specific compound and the p-type organic semiconductor is preferably 0.1 eV or more.

When the photoelectric conversion film contains a p-type organic semiconductor, the content of the p-type organic semiconductor in the photoelectric conversion film (=film thickness of the p-type organic semiconductor in terms of a single layer/thickness of the photoelectric conversion film×100) is 15 to 75% by volume is preferred, 20 to 60% by volume is more preferred, and 25 to 50% by volume is even more preferred.
The p-type semiconductor material may be used singly or in combination of two or more.

A photoelectric conversion film containing a specific compound is a non-luminous film and has characteristics different from those of an organic electroluminescent device (OLED: Organic Light Emitting Diode). A non-luminous film is intended to be a film having a luminescence quantum efficiency of 1% or less, preferably 0.5% or less, more preferably 0.1% or less. The lower limit is often 0% or more.

<Deposition method>
Examples of a method for forming a photoelectric conversion film include a dry film forming method.
Examples of dry film formation methods include vapor deposition (especially vacuum vapor deposition), sputtering, ion plating, MBE (Molecular Beam Epitaxy) and other physical vapor deposition methods, and plasma polymerization and other CVD (Chemical Vapor Deposition) method is mentioned, and a vacuum deposition method is preferable. When forming a photoelectric conversion film by a vacuum deposition method, manufacturing conditions such as the degree of vacuum and deposition temperature can be set according to conventional methods.

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

[electrode]
The photoelectric conversion element preferably has electrodes.
The electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Conductive materials 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. Materials constituting the upper electrode 15 include, for example, antimony or fluorine-doped tin oxide (ATO: Antimony Tin Oxide, FTO: Fluorine doped Tin Oxide), tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO). Conductive metal oxides such as Indium Tin Oxide (IZO) and Indium Zinc Oxide (IZO); Metal thin films such as gold, silver, chromium and nickel; Mixtures or laminates of these metals and conductive metal oxides and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and conductive metal oxides are preferred from the viewpoint of high conductivity and transparency.

Generally, when the conductive film is made thinner than a certain range, the resistance value increases abruptly in many cases. In the solid-state imaging device incorporating the photoelectric conversion device according to this embodiment, the sheet resistance may be 100 to 10000Ω/□, and the degree of freedom in the range of film thickness that can be reduced is large.
Also, the thinner the upper electrode (transparent conductive film) 15, the less light it absorbs, and generally the light transmittance increases. An increase in light transmittance is preferable because it increases the light absorption in the photoelectric conversion film and increases the photoelectric conversion performance. Considering the suppression of leakage current, the increase in the resistance value of the thin film, and the increase in transmittance due to thinning, the thickness of the upper electrode 15 is preferably 5 to 100 nm, more preferably 5 to 20 nm.

Depending on the application, the lower electrode 11 may be transparent or may reflect light without transparency. Materials constituting the lower electrode 11 include, for example, tin oxide (ATO, FTO) doped with antimony or fluorine, 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 (e.g., titanium nitride (TiN), etc.); and conductive metal oxides; and organic conductive materials such as polyaniline, polythiophene and polypyrrole.

A method for forming the electrodes can be appropriately selected according to the electrode material. Specific examples include wet methods such as printing methods and coating methods; physical methods such as vacuum deposition methods, sputtering methods and ion plating methods; and chemical methods such as CVD and plasma CVD methods.
When the electrode material is ITO, methods such as an electron beam method, a sputtering method, a resistance heating vapor deposition method, a chemical reaction method (such as a sol-gel method), and application of an indium tin oxide dispersion can be used.

[Charge blocking film: electron blocking film, hole blocking film]
The photoelectric conversion element preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
Examples of the intermediate layer include a charge blocking film. If the photoelectric conversion element has this film, the characteristics (photoelectric conversion efficiency, responsiveness, etc.) of the obtained photoelectric conversion element are more excellent. Charge blocking films include, for example, electron blocking films and hole blocking films.

<Electron blocking film>
The electron blocking film is a donor organic semiconductor material (compound), and the above p-type organic semiconductor can be used.
Polymeric materials can also be used as the electron blocking film.
Examples of polymeric materials include polymers such as phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene and diacetylene, and derivatives thereof.

Note that the electron blocking film may be composed of a plurality of films.
The electron blocking film may be composed of an inorganic material. In general, an inorganic material has a higher dielectric constant than an organic material. Therefore, when an inorganic material is used for an electron blocking film, a large voltage is applied to the photoelectric conversion film, resulting in a high photoelectric conversion efficiency. Examples of inorganic materials that can serve as an electron blocking film include calcium oxide, chromium oxide, chromium copper oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, gallium copper oxide, strontium copper oxide, niobium oxide, molybdenum oxide, and indium oxide. Copper, indium silver oxide and iridium oxide are mentioned.

<Hole blocking film>
The hole blocking film is an acceptor organic semiconductor material (compound), and can use the above n-type y organic semiconductor.
Note that the hole blocking film may be composed of a plurality of films.

Examples of methods for manufacturing the charge blocking film include dry film formation methods and wet film formation methods. Dry film-forming methods include, for example, a vapor deposition method and a sputtering method. The vapor deposition method may be 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 formation methods include inkjet, spray, nozzle printing, spin coating, dip coating, casting, die coating, roll coating, bar coating, and gravure coating, and high precision. From the viewpoint of patterning, the inkjet method is preferable.

The thickness of the charge blocking film (electron blocking film and hole blocking film) is preferably 3 to 200 nm, more preferably 5 to 100 nm, and even more preferably 5 to 30 nm.

<Substrate>
The photoelectric conversion element may further have a substrate.
Substrates include, for example, semiconductor substrates, glass substrates, and plastic substrates.
Although the position of the substrate is not particularly limited, the conductive film, the photoelectric conversion film and the transparent conductive film are usually laminated in this order on the substrate.

<Sealing layer>
The photoelectric conversion element may further have a sealing layer.
The performance of the photoelectric conversion material may be remarkably deteriorated due to the presence of deterioration factors such as water molecules. Therefore, the entire photoelectric conversion film is covered with a sealing layer such as dense ceramics such as metal oxide, metal nitride or metal oxynitride, or diamond-like carbon (DLC) that does not allow water molecules to permeate. The above deterioration can be prevented by sealing.
The sealing layer is described, for example, in paragraphs [0210] to [0215] of JP-A-2011-082508, the contents of which are incorporated herein.

[Image sensor]
An example of an application of a photoelectric conversion element is an imaging element.
An image pickup device is a device that converts optical information of an image into an electrical signal. Usually, a plurality of photoelectric conversion devices are arranged in a matrix on the same plane. is converted into an electric signal, and the electric signal can be sequentially output to the outside of the image sensor for each pixel. Therefore, each pixel is composed of one or more photoelectric conversion elements and one or more transistors.

[Optical sensor]
Other applications of the photoelectric conversion element include, for example, photoelectric cells and optical sensors, and the photoelectric conversion element of the present invention is preferably used as an optical sensor. As the optical sensor, the photoelectric conversion element may be used alone, or may be used as a line sensor in which the photoelectric conversion elements are linearly arranged or a two-dimensional sensor in which the photoelectric conversion elements are arranged on a plane.

〔Compound〕
The present invention also includes compound inventions. The compound of the present invention is the specific compound described above.

The present invention will be described in more detail based on examples below. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the gist of the present invention. Therefore, the scope of the present invention should not be construed to be limited by the examples shown below.

[Compound used for photoelectric conversion film]
[Synthesis of compound (D-1)]
Compound (D-1) was synthesized according to the following scheme.

1-aminopyrrole (3.0 g, 35.8 mmol), ethyl 4,4,4-trifluoroacetoacetate (7.25 g, 39.4 mmol), p-toluenesulfonic acid-hydrate (1.34 g, 7 .16 mmol) and toluene (120 mL) were stirred at 100° C. for 1 hour. The resulting reaction solution was allowed to cool to room temperature, insoluble matter was removed by Celite filtration, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent (volume ratio): dichloromethane/ethyl acetate = 80:20) to give compound (D-1-1) (1.50 g, yield 21%). got

To a mixture of 2,6-xylidine (300 g, 2.48 mol) and isopropanol (300 mL), 30% hydrochloric acid (288 mL, 2.73 mol) was added dropwise, and the resulting reaction mixture was heated under reflux and stirred for 1 hour. . The mixture was cooled to 2° C., and the resulting crystals were filtered and washed with isopropanol and hexane in that order to give 2,6-xylidine hydrochloride (350 g, yield 90%). Subsequently, to a mixture of 2,6-xylidine hydrochloride (300 g, 1.90 mol) and water (600 mL), 50% aqueous sodium hydroxide solution (199 g, 2.48 mol) was added dropwise, and the resulting reaction mixture was allowed to cool to room temperature. Stir at (25° C.) for 1 hour. The resulting mixed solution was transferred to a separating funnel, hexane (150 mL) was added for washing, and then the aqueous phase was removed. The resulting organic phase was concentrated under reduced pressure to give 2,6-xylidine (200 g, 87%).

2,3-dichloroquinoxaline (8.0 g, 40.2 mmol), hexamethyldisilazane sodium 35% tetrahydrofuran solution (1.9 mol / L) (90.4 mL, 181 mol) and tetrahydrofuran (80 mL) were mixed, 2,6-Xylidine (11 mL, 88.2 mmol) obtained above was added dropwise. After stirring at 60° C. for 1 hour, the mixture was allowed to cool to room temperature, and water (40 mL) was added dropwise. Further, 20 wt% brine (80 mL) was added and the organic phase was extracted. The resulting organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was recrystallized using a mixture of toluene/2-propanol to obtain intermediate (D-1-2) (9.95 g, yield 67%).

p-Toluenesulfonic acid-hydrate (9.3 g, 48.9 mmol), acetic anhydride (16 mL) and intermediate (D-1-2) (6.0 g, 16.3 mmol) were added and stirred at 130°C for 1 Stirred for an hour. The resulting reaction solution was allowed to cool to room temperature, added dropwise to a mixture of 50% by mass/volume sodium hydroxide aqueous solution (48 mL) and ice (143 g), and stirred for 30 minutes. Acetic acid was added to the reaction mixture to adjust the pH to 8 and stirred for an additional 20 minutes. The resulting precipitate was filtered and washed with water and methanol in that order. Intermediate (D-1-3) (6.2 g, yield 98%) was obtained by reprecipitating the resulting crude product from a mixture of dichloromethane/methanol.

To a mixture of (chloromethylene)dimethyliminium chloride (5.87 g, 45.9 mmol) and acetonitrile (60 mL) was added intermediate (D-1-3) (6.0 g, 15.3 mmol), Stir at 50° C. for 2 hours. The reaction solution allowed to cool to room temperature was added dropwise to a mixture of 1 mol/L sodium hydroxide aqueous solution (90 mL) and ice (90 g), and stirred for 1 hour. The resulting precipitate was filtered and washed with water and methanol in that order. Intermediate (D-1-4) (4.4 g, yield 68%) was obtained by reprecipitating the resulting crude product from a mixture of dichloromethane/acetonitrile.

Intermediate (D-1-4) (0.80 g, 1.64 mmol), Intermediate (D-1-1) (0.43 g, 2.13 mmol) and acetic anhydride (375 mL) were mixed and heated at 130°C. Stirred for 30 hours. After allowing the reaction solution to cool to room temperature, the resulting precipitate was filtered and washed with methanol. The obtained crude product was purified by silica gel chromatography (eluent (volume ratio): dichloromethane/ethyl acetate=96:4) to obtain compound (D-1) (0.41 g, yield 37%). rice field.

The compounds used in the photoelectric conversion film other than the compound (D-1) were synthesized by referring to the method for synthesizing the compound (D-1).
Each compound is shown below.
Compounds (D-1) to (D-13) correspond to specific compounds, and compounds (R-1) to (R-2) correspond to comparative compounds.

[n-type organic semiconductor]
C60: Fullerene ₍ C60)

[p-type organic semiconductor]

〔evaluation〕
[Production of photoelectric conversion element]
Using the obtained compound, a photoelectric conversion device having the configuration shown in FIG. 1 was produced. Here, the photoelectric conversion element is composed of a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12 and an upper electrode 15. FIG.
Specifically, an amorphous ITO film is formed on a glass substrate by a sputtering method to form a lower electrode 11 (thickness: 30 nm), and the following compound (EB-1) is applied on the lower electrode 11 in a vacuum. An electron blocking film 16A (thickness: 30 nm) was formed by depositing by a heating vapor deposition method.
Furthermore, with the temperature of the substrate controlled at 25° C., each specific compound and n-type organic semiconductor (fullerene (C ₆₀ )) were deposited on the electron blocking film 16A so as to have a thickness of 80 nm in terms of a single layer by vacuum deposition. A film was formed by co-depositing with. As a result, a photoelectric conversion film 12 having a bulk heterostructure of 160 nm (240 nm when a p-type semiconductor material is also used) was formed.
Further, an amorphous ITO film was formed on the photoelectric conversion film 12 by a sputtering method to form an upper electrode 15 (transparent conductive film) (thickness: 10 nm). After forming a SiO film as a sealing layer on the upper electrode 15 by a vacuum deposition method, an aluminum oxide (Al ₂ O ₃ ) layer is formed thereon by an ALCVD (Atomic Layer Chemical Vapor Deposition) method to obtain a photoelectric conversion element. (Device (A)) was produced.

[Evaluation of photoelectric conversion efficiency (external quantum efficiency)]
Driving of each photoelectric conversion element (element (A)) obtained was confirmed. A voltage was applied to each photoelectric conversion element so as to have an electric field intensity of 2.0×10 ⁵ V/cm. After that, light is irradiated from the upper electrode (transparent conductive film) side, IPCE (Incident photon-to-current conversion efficiency) is measured, and each photoelectric conversion efficiency (external quantum efficiency) at a wavelength of 500 nm and a wavelength of 600 nm is extracted. bottom. The photoelectric conversion efficiency was measured using an Optel constant energy quantum efficiency measurement device. The amount of irradiated light was 50 μW/cm ² . The photoelectric conversion efficiency of each photoelectric conversion element was determined when the photoelectric conversion efficiency of the photoelectric conversion element of Example 1 was normalized to 1, and was evaluated in the following categories based on the determined photoelectric conversion efficiency.
A: 0.9 or more B: 0.8 or more and less than 0.9 C: 0.7 or more and less than 0.8 D: less than 0.7 For both wavelengths of 500 nm and 600 nm, C It is preferable that it becomes above, and it is most preferable that it becomes A.
In addition, the photoelectric conversion element (element (A)) of each example or each comparative example exhibits a photoelectric conversion efficiency of 40% or more at a wavelength of 500 nm and a wavelength of 600 nm, and has a certain or higher external quantum efficiency as a photoelectric conversion element. It was confirmed to have

[Evaluation of manufacturability (photoelectric conversion efficiency during high-speed film formation)]
A photoelectric conversion element (element (B)) of each example or comparative example was produced in the same manner as the element (A), except that the film formation rate of the photoelectric conversion film 12 was set to 3.0 Å/sec. Using the obtained device (B), photoelectric conversion efficiency (external quantum efficiency) was evaluated in the same manner as shown in the item [Evaluation of photoelectric conversion efficiency (external quantum efficiency)].
Comparing the photoelectric conversion efficiency of the element (A) and the element (B) of the same example or comparative example, calculating the value of "photoelectric conversion efficiency of element (B) / photoelectric conversion efficiency of element (A)", The manufacturing suitability of each photoelectric conversion element was evaluated in light of the obtained values according to the following criteria.
A: 0.90 or more B: less than 0.90

[Evaluation of responsiveness]
Responsiveness of each device (A) obtained was evaluated. A voltage of 2.0×10 ⁵ V/cm was applied to each device (A). After that, the LED (light emitting diode) is turned on momentarily to irradiate light from the upper electrode (transparent conductive film) side, and the photocurrent at a wavelength of 580 nm is measured with an oscilloscope, and the signal intensity changes from 0% to 97%. The rise time to rise to signal strength was timed. Then, the rise time of the photoelectric conversion element when using the compound (D-1) at a wavelength of 580 nm is normalized to 1, and each element ( The relative value of the rise time of A) (the relative value of the rise time of each element (A) / the rise time of the element (A) when using the compound (D-1)) is obtained, and the obtained value is measured according to the following criteria. Evaluated by In addition, D or more is preferable practically, and A is the most preferable.
A: Less than 1.0 B: 1.0 or more and less than 2.0 C: 2.0 or more and less than 3.0 D: 3.0 or more

Table 1 shows the evaluation results.
Each notation in Table 1 indicates the following.
The column of "D ¹ " means the formula of the lowest concept among the formulas to which D ¹ corresponds. Specifically, in the case of the specific compound (D-1), D ¹ corresponds to all of formula (1D) and formula (4D) to formula (6D), but the most subordinate concept among the above formula ( 6D) only.
^The order of the concepts in D1 is the lower concepts in the order of formula (1D) to formula (3D)/formula (4D)/formula (5D)/formula (6D).
The column of "A ¹ " means the formula of the lowest concept among the formulas to which A ¹ corresponds. Specifically, in the case of the specific compound (D-1), A ¹ corresponds to both formula (1A) and formula (2A), but only formula (2A), which is the most subordinate concept among the above shall be described.
Note that the order of the concepts in A1 above is a subordinate concept in the order of formula ( ^1A )/formula (2A) and formula (3A).
In the column of "Y ^a11 ", when "A ¹ " corresponds to formula (1A) and Y ^a11 in formula (1A) or the portion corresponding to Y ^a11 in the specific compound is an oxygen atom, "O", and "S" when it is a sulfur atom.
In the column of "Number of ring members of Ar ^a11 ", "A ¹ " corresponds to formula (1A), and the number of ring members of the portion corresponding to Ar ^a11 in formula (1A) or Ar ^a11 in the specific compound is When it was 5, it was set to "5", and when it was 6, it was set to "6".

From the results shown in the table above, it was confirmed that the photoelectric conversion element of the present invention can achieve the desired effects.
It was confirmed that when Y ^a11 was an oxygen atom, the effects of the present invention were more excellent (comparison of Examples 1-6 and 1-7, etc.).
It was confirmed that the effects of the present invention are more excellent when Ar ^a11 is a five-membered ring (comparison with Examples 1-5 to 1-9, etc.).
It was confirmed that when A ¹ is a group represented by formula (2A) or a group represented by formula (3A), the responsiveness is more excellent (Examples 1-1 to 1-2 and 1-6 comparison, etc.).
It was confirmed that the effects of the present invention are more excellent when D ¹ is a group represented by any one of formulas (1D) to (3D) (Examples 1-1 and 1-10 to 1- 13 comparisons, etc.). Further, from a similar comparison, when D ¹ is a group represented by formula (1D) (preferably formula (5D), more preferably formula (6D)), it is confirmed that the effects of the present invention are more excellent. was done.
It was confirmed that the responsiveness was more excellent when the photoelectric conversion film further contained an n-type organic semiconductor and a p-type organic semiconductor (comparison of Examples 1-1, 1-14 and 1-15, etc.).

10a, 10b photoelectric conversion element 11 conductive film (lower electrode)
12 photoelectric conversion film 15 transparent conductive film (upper electrode)
16A electron blocking film 16B hole blocking film

Claims (24)

A photoelectric conversion element having a conductive film, a photoelectric conversion film and a transparent conductive film in this order,
A photoelectric conversion device, wherein the photoelectric conversion film contains a compound represented by formula (1).

In formula ( ¹ ), A1 represents a group represented by formula (1A). D ¹ represents a substituent having an aromatic ring. R ¹ represents a hydrogen atom or a substituent.

In formula (1A), * represents a binding position. Y ^a11 represents an oxygen atom, a sulfur atom, =NR ^Y11 or =CR ^Y12 R ^Y13 . ^RY11 represents a hydrogen atom or a substituent. R ^Y12 and R ^Y13 each independently represent a cyano group or —COOR ^Y14 . ^RY14 represents an optionally substituted alkyl group or an optionally substituted aromatic ring group.
X ^a11 and X ^a12 each independently represent a nitrogen atom or =C<. The bonds of ^Xa11 and ^Xa12 represented by solid lines and dotted lines represent single bonds or double bonds. However, when the bond between X ^a11 and X ^a12 represents a double bond, X ^a11 and X ^a12 represent =C<. When the bond between X ^a11 and X ^a12 represents a single bond, one of X ^a11 and X ^a12 represents a nitrogen atom and the other represents a nitrogen atom or =C<. X ^a13 represents a nitrogen atom or —CR ^X11 =. R ^X11 represents a hydrogen atom or a substituent. Ar ^a11 represents a ring containing X ^a11 and X ^a12 . The ring represented by Ar ^a11 may further have a substituent. The photoelectric conversion device according to claim 1, wherein Y ^a11 is an oxygen atom. 3. The photoelectric conversion device according to claim 1, wherein Ar ^a11 is a five-membered ring. The photoelectric conversion device according to any one of claims 1 to 3, wherein A ¹ is a group represented by formula (2A) or a group represented by formula (3A).

In formula (2A), * represents a binding position. R ^a21 represents a hydrogen atom or a substituent. X ^a21 to X ^a23 each independently represent a nitrogen atom or —CR ^X21 =. R ^X21 represents a hydrogen atom or a substituent.
In formula (3A), * represents a binding position. R ^a31 and R ^a32 each independently represent a hydrogen atom or a substituent. X ^a31 and X ^a32 each independently represent a nitrogen atom or —CR ^X22 =. R ^X22 represents a hydrogen atom or a substituent. The photoelectric conversion device according to any one of claims 1 to 4, wherein D ¹ is a group represented by any one of formulas (1D) to (3D).

In formula (1D), * represents a binding position. Ar ^d11 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d11 may further have a substituent. R ^d11 and R ^d12 each independently represent —C(R ^L11 ) (R ^L12 ) (R ^L13 ) or an optionally substituted aromatic ring group. R ^L11 to R ^L13 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L11 to R ^L13 may combine with each other to form a ring. R ^d13 represents a hydrogen atom or a substituent.
In formula (2D), * represents a binding position. Ar ^d21 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d21 may further have a substituent. Z ^d21 represents a chalcogen atom or -NR ^Z21 -. R ^Z21 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. Z ^d22 represents a nitrogen atom or -CR ^Z22 =. R ^Z22 represents a hydrogen atom or a substituent.
In formula (3D), * represents a binding position. Ar ^d31 and Ar ^d32 each independently represent an aromatic ring containing two or more carbon atoms. The aromatic rings represented by Ar ^d31 and Ar ^d32 may further have a substituent. Z ^d31 represents -CR ^Z31 R ^Z32 -, -SiR ^Z31 R ^Z32 - or >C=R ^Z33 . R ^Z31 and R ^Z32 each independently represent a hydrogen atom or a substituent. R 2 ^Z31 and R 2 ^Z32 may combine with each other to form a ring. R ^Z33 represents an oxygen atom, a sulfur atom or =CR ^Z34 R ^Z35 . R ^Z34 and R ^Z35 each independently represent a hydrogen atom or a substituent. At least one of R ^Z34 and R ^Z35 and at least one of Ar ^d31 and Ar ^d32 may be condensed with each other to form a condensed ring. R ^d31 represents a hydrogen atom or a substituent. The photoelectric conversion device according to claim 5, wherein D1 is ^a group represented by formula (1D). The photoelectric conversion device according to any one of claims 1 to 6, wherein D ¹ is a group represented by formula (4D).

In formula (4D), * represents a binding position. R ^d41 and R ^d42 each independently represent —C(R ^L41 ) (R ^L42 ) (R ^L43 ) or an optionally substituted aromatic ring group. R ^L41 to R ^L43 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L41 to R ^L43 may combine with each other to form a ring. R ^d43 represents a hydrogen atom or a substituent. E ^d41 to E ^d44 each independently represent a nitrogen atom or —CR ^E41 =. R ^E41 represents a hydrogen atom or a substituent. When multiple R ^E41 are present, the multiple R ^E41 may be bonded to each other to form a ring. The photoelectric conversion device according to any one of claims 1 to 7, wherein D ¹ is a group represented by formula (5D).

In formula (5D), * represents a binding position. R ^d51 and R ^d52 each independently represent —C(R ^L51 ) (R ^L52 ) (R ^L53 ) or an optionally substituted aromatic ring group. R ^L51 to R ^L53 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L51 to R ^L53 may combine with each other to form a ring. R ^d53 to R ^d55 each independently represent a hydrogen atom or a substituent. R ^d54 and R ^d55 may combine with each other to form a ring. The photoelectric conversion device according to any one of claims 1 to 8, wherein D ¹ is a group represented by formula (6D).

In formula (6D), * represents a binding position. R ^d61 and R ^d62 each independently represent —C(R ^L61 ) (R ^L62 ) (R ^L63 ) or an optionally substituted aromatic ring group. R ^L61 to R ^L63 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L61 to R ^L63 may combine with each other to form a ring. R ^d63 to R ^d65 each independently represent a hydrogen atom or a substituent. R ^d64 and R ^d65 may combine with each other to form a ring. E ^d61 and E ^d62 each independently represent a nitrogen atom or -CR ^E61 =. R ^E61 represents a hydrogen atom or a substituent. The photoelectric conversion film further includes an n-type organic semiconductor,
The photoelectric conversion film according to any one of claims 1 to 9, wherein the compound represented by the formula (1) and the n-type organic semiconductor have a bulk heterostructure formed in a mixed state. The photoelectric conversion device described. 11. The photoelectric conversion device according to claim 10, wherein said n-type organic semiconductor contains fullerenes selected from the group consisting of fullerenes and derivatives thereof. 12. The photoelectric conversion device according to claim 10, wherein said photoelectric conversion film further contains a p-type organic semiconductor. 13. The photoelectric conversion element according to claim 1, further comprising one or more intermediate layers in addition to said photoelectric conversion film between said conductive film and said transparent conductive film. An imaging device comprising the photoelectric conversion device according to any one of claims 1 to 13. An optical sensor comprising the photoelectric conversion element according to any one of claims 1 to 13. A compound represented by formula (1).

In formula ( ¹ ), A1 represents a group represented by formula (1A). D ¹ represents a substituent having an aromatic ring. R ¹ represents a hydrogen atom or a substituent.

In formula (1A), * represents a binding position. Y ^a11 represents an oxygen atom, a sulfur atom, =NR ^Y11 or =CR ^Y12 R ^Y13 . ^RY11 represents a hydrogen atom or a substituent. R ^Y12 and R ^Y13 each independently represent a cyano group or —COOR ^Y14 . ^RY14 represents an optionally substituted alkyl group or an optionally substituted aromatic ring group.
X ^a11 and X ^a12 each independently represent a nitrogen atom or =C<. The bonds of ^Xa11 and ^Xa12 represented by solid lines and dotted lines represent single bonds or double bonds. However, when the bond between X ^a11 and X ^a12 represents a double bond, X ^a11 and X ^a12 represent =C<. When the bond between X ^a11 and X ^a12 represents a single bond, one of X ^a11 and X ^a12 represents a nitrogen atom and the other represents a nitrogen atom or =C<. X ^a13 represents a nitrogen atom or —CR ^X11 =. R ^X11 represents a hydrogen atom or a substituent. Ar ^a11 represents a ring containing X ^a11 and X ^a12 . The ring represented by Ar ^a11 may further have a substituent. 17. The compound of claim 16, wherein Y ^a11 is an oxygen atom. 18. The compound of claim 16 or 17, wherein Ar ^a11 is a 5-membered ring. The compound according to any one of claims 16 to 18, wherein A ¹ is a group represented by formula (2A) or a group represented by formula (3A).

In formula (2A), * represents a binding position. R ^a21 represents a hydrogen atom or a substituent. X ^a21 to X ^a23 each independently represent a nitrogen atom or —CR ^X21 =. R ^X21 represents a hydrogen atom or a substituent.
In formula (3A), * represents a binding position. R ^a31 and R ^a32 each independently represent a hydrogen atom or a substituent. X ^a31 and X ^a32 each independently represent a nitrogen atom or —CR ^X22 =. R ^X22 represents a hydrogen atom or a substituent. The compound according to any one of claims 16 to 19, wherein D ¹ is a group represented by any one of formulas (1D) to (3D).

In formula (1D), * represents a binding position. Ar ^d11 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d11 may further have a substituent. R ^d11 and R ^d12 each independently represent —C(R ^L11 ) (R ^L12 ) (R ^L13 ) or an optionally substituted aromatic ring group. R ^L11 to R ^L13 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L11 to R ^L13 may combine with each other to form a ring. R ^d13 represents a hydrogen atom or a substituent.
In formula (2D), * represents a binding position. Ar ^d21 represents an aromatic ring containing two or more carbon atoms. The aromatic ring represented by Ar ^d21 may further have a substituent. Z ^d21 represents a chalcogen atom or -NR ^Z21 -. R ^Z21 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. Z ^d22 represents a nitrogen atom or -CR ^Z22 =. R ^Z22 represents a hydrogen atom or a substituent.
In formula (3D), * represents a binding position. Ar ^d31 and Ar ^d32 each independently represent an aromatic ring containing two or more carbon atoms. The aromatic rings represented by Ar ^d31 and Ar ^d32 may further have a substituent. Z ^d31 represents -CR ^Z31 R ^Z32 -, -SiR ^Z31 R ^Z32 - or >C=R ^Z33 . R ^Z31 and R ^Z32 each independently represent a hydrogen atom or a substituent. R 2 ^Z31 and R 2 ^Z32 may combine with each other to form a ring. R ^Z33 represents an oxygen atom, a sulfur atom or =CR ^Z34 R ^Z35 ; R ^Z34 and R ^Z35 each independently represent a hydrogen atom or a substituent. At least one of R ^Z34 and R ^Z35 and at least one of Ar ^d31 and Ar ^d32 may be condensed with each other to form a condensed ring. R ^d31 represents a hydrogen atom or a substituent. 21. The compound according to claim 20, wherein D1 is ^a group represented by formula (1D). The compound according to any one of claims 16 to 21, wherein D ¹ is a group represented by formula (4D).

In formula (4D), * represents a binding position. R ^d41 and R ^d42 each independently represent —C(R ^L41 ) (R ^L42 ) (R ^L43 ) or an optionally substituted aromatic ring group. R ^L41 to R ^L43 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L41 to R ^L43 may combine with each other to form a ring. R ^d43 represents a hydrogen atom or a substituent. E ^d41 to E ^d44 each independently represent a nitrogen atom or —CR ^E41 =. R ^E41 represents a hydrogen atom or a substituent. When multiple R ^E41 are present, the multiple R ^E41 may be bonded to each other to form a ring. A compound according to any one of claims 16 to 22, wherein D ¹ is a group represented by formula (5D).

In formula (5D), * represents a binding position. R ^d51 and R ^d52 each independently represent —C(R ^L51 ) (R ^L52 ) (R ^L53 ) or an optionally substituted aromatic ring group. R ^L51 to R ^L53 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L51 to R ^L53 may combine with each other to form a ring. R ^d53 to R ^d55 each independently represent a hydrogen atom or a substituent. R ^d54 and R ^d55 may combine with each other to form a ring. The compound according to any one of claims 16 to 23, wherein D ¹ is a group represented by formula (6D).

In formula (6D), * represents a binding position. R ^d61 and R ^d62 each independently represent —C(R ^L61 ) (R ^L62 ) (R ^L63 ) or an optionally substituted aromatic ring group. R ^L61 to R ^L63 each independently represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aromatic ring group. The alkyl groups optionally having substituents or the aromatic ring groups optionally having substituents represented by R ^L61 to R ^L63 may combine with each other to form a ring. R ^d63 to R ^d65 each independently represent a hydrogen atom or a substituent. R ^d64 and R ^d65 may combine with each other to form a ring. E ^d61 and E ^d62 each independently represent a nitrogen atom or -CR ^E61 =. R ^E61 represents a hydrogen atom or a substituent.

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