Organic electronic element and imide compound

Abstract

The present invention provides an organic electronic element and an imide compound which make it possible to improve electron transport capability.　The organic electronic element comprises a first electrode, a second electrode, and an organic layer that is disposed between the first electrode and the second electrode, wherein the organic layer includes an electron transport layer, and the electron transport layer includes a compound represented by formula (1). In formula (1), each Ra independently represents a hydrogen atom, a hydroxy group, a thiol group, an amino group, a cyano group, a carboxy group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a C3-18 linear, branched, or cyclic alkyl group, a C6-30 aromatic hydrocarbon group, or a C3-20 heteroaromatic group. n represents an integer of 0 to 2. L1 represents a single bond, a C1-18 linear, branched, or cyclic (n +1)-valent aliphatic hydrocarbon group, a C6-18 (n +1)-valent aromatic hydrocarbon group, or a C3-20 (n +1)-valent heteroaromatic group.

Description

Organic electronic devices and imide compounds

[0001] This invention relates to organic electronic devices and imide compounds.

[0002] Currently, there are active efforts to create new high-performance devices using organic materials. In particular, research and development on organic electronic elements such as photoelectric converters and organic EL elements is active, and material and device design aimed at improving the performance of these devices is progressing. For example, photoelectric converters used for video recording require a high speed to transport carriers (electrons and holes) generated in the light-receiving layer to the electrodes in order to suppress the cause of afterimages. Similarly, organic EL elements require a high speed to transport carriers from the electrodes to the light-emitting layer in order to suppress the rise in driving voltage. Thus, improving the efficiency of carrier movement within the element is required to improve the performance of devices.

[0003] Patent Document 1 discloses an imide compound as a compound for electron transport materials used in electrophotographic photoreceptors to achieve the above characteristics. However, even with the imide compound described in Patent Document 1, further performance improvements are required in the field of organic electronic devices.

[0004] Japanese Patent Publication No. 2019-182789

[0005] The present invention provides an organic electronic element and an imide compound that can improve electron transport capability or reduce energy barriers with adjacent layers.

[0006] As a result of diligent research to solve the above problems, the present inventors have discovered that certain compounds having an imide skeleton as a partial structure can improve the electron transport capability in organic electronic devices such as photoelectric conversion elements and organic EL elements, and have completed the present invention.

[0007] In other words, the present invention encompasses the following embodiments: [1] an organic electronic element comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an electron transport layer, and the electron transport layer comprises a compound represented by the following formula (1). (In formula (1), R aeach independently represent a hydrogen atom, a hydroxy group, a thiol group, an amino group, a cyano group, a carboxy group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The alkyl group, the aromatic hydrocarbon group and the heteroaromatic group may have a substituent. The aromatic hydrocarbon group and the heteroaromatic group may be a monocyclic ring, a condensed ring or a linked ring, or may be a condensed ring or a linked ring formed by the aromatic hydrocarbon group and the heteroaromatic group. n represents an integer of 0 to 2. When n is 2, R a may be the same as or different from each other. L １ represents a single bond, a (n+1)-valent linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a (n+1)-valent aromatic hydrocarbon group having 6 to 18 carbon atoms, or a (n+1)-valent heteroaromatic group having 3 to 20 carbon atoms. The aliphatic hydrocarbon group, the aromatic hydrocarbon group and the heteroaromatic group may have a substituent. The aromatic hydrocarbon group and the heteroaromatic group may be a monocyclic ring, a condensed ring or a linked ring. R １ to R ６ each independently represent a hydrogen atom, a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, an iodo group, an aromatic hydrocarbon group having 6 to 30 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon group and the heteroaromatic group may have one or more of a substituent and a linking group.) [2] In the formula (1), the R a , the L １ , and the R １ to R ６The organic electronic element according to [1], wherein the substituents that may be present are, each independently, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, a linear, branched, or cyclic alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a combination thereof. [3] The organic electronic element according to [1] or [2], further comprising a light-receiving layer disposed between the first electrode and the second electrode. [4] The organic electronic element according to [3], wherein the light-receiving layer is a layer containing at least two organic components. [5] The organic electronic element according to any one of [1] to [3], wherein the organic layer further comprises a hole transport layer. [6] In formula (1), the R １ and R ２ The organic electronic element according to any one of [1] to [5], wherein each is independently a hydrogen atom, a phenyl group, or a naphthyl group. [7] In formula (1), the R ３ , the R ４ and R ６ is a hydrogen atom, and the R ５ An organic electronic element according to any one of [1] to [6], wherein is a hydrogen atom, a cyano group, a trifluoromethyl group, a methoxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a phenyl group, or a pyridyl group. [8] An imide compound represented by the following formula (2). (In formula (2), R ｂEach independently represents a hydrogen atom, a hydroxyl group, a thiol group, an amino group, a cyano group, a carboxyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. n represents an integer from 0 to 2. When n is 2, R ｂ They may be the same or different from each other. ２ R represents a single bond, a linear, branched, or cyclic (n+1) valency aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n+1) valency aromatic hydrocarbon group having 6 to 18 carbon atoms, or a (n+1) valency heteroaromatic group having 3 to 20 carbon atoms. The aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings. １１ ~R １６ Each of these independently represents a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, an iodo group, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups. However, L ２ If it is a single bond, R ｂ is a phenyl group (limited to phenyl groups without substituents). ) [9] In formula (2), the R ｂ , said L ２ , and the R １１ ~R １６In the present invention, the substituents that may be present are, independently, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, a linear, branched, or cyclic alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a combination thereof, the imide compound according to [8].

[10] In formula (2), the R ｂ However, each is independently an alkyl group, a cycloalkyl group, an adamantyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a bipyridyl group, a terpyridyl group, a pyrazyl group, a pyrimidyl group, a triazyl group, a quinolyl group, a quinoxalinyl group, a quinazolyl group, an imidazolyl group, a benzimidazolyl group, a thiazolyl group, a benzothiazolyl group, an oxazolyl group, or a benzoxazolyl group, and these groups may have substituents. The imide compound as described in [8] or [9].

[11] In formula (2), the L ２ The imide compound according to any one of [8] to

[10] , wherein R is a single bond, (n+1)-valent benzene, (n+1)-valent naphthalene, (n+1)-valent pyridine, or (n+1)-valent pyrimidine, and these groups may have substituents.

[12] In formula (2), the R １１ and R １２ The imide compound according to claim 8, wherein each is independently a hydrogen atom, a phenyl group, or a naphthyl group.

[13] In formula (2), the R １３ , the R １４ and R １６ is a hydrogen atom, and the R １５ The imide compound according to claim 8, wherein is any of a hydrogen atom, a cyano group, a trifluoromethyl group, a methoxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a phenyl group, or a pyridyl group.

[0008] According to the present invention, it is possible to provide an organic electronic element and an imide compound that can improve electron transport capability or reduce energy barriers with adjacent layers.

[0009] This is a schematic cross-sectional view showing an example of a stacked configuration of a photoelectric conversion element according to the present invention. This is a schematic cross-sectional view showing an example of a stacked configuration of an organic EL element including a photoelectric conversion element according to the present invention.

[0010] (Organic Electronic Elements) The organic electronic elements of the present invention include photoelectric conversion elements and organic electroluminescent elements (organic EL elements). Photoelectric conversion elements are elements that convert light energy into electrical energy or electrical signals, and include image sensors, light sensors, solar cells, etc.

[0011] The organic electronic device of the present invention comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode. The organic layer includes an electron transport layer, and the electron transport layer contains a compound represented by the following formula (1).

[0012] A detailed explanation of the compound represented by formula (1) above will be given later. As described above, the organic layer includes an electron transport layer. Here, the electron transport layer has the role of transporting electrons and contains an electron transport material. The compound represented by formula (1) above is not particularly limited, but can be used as an electron transport material.

[0013] A photoelectric conversion element is a preferred embodiment of the organic electronic element of the present invention. The photoelectric conversion element preferably includes a first electrode, a second electrode, and an organic layer and a light-receiving layer disposed between the first electrode and the second electrode. The element configuration of the organic electronic element will be described below using the photoelectric conversion element as an example.

[0014] <Configuration of the Photoelectric Conversion Element> The photoelectric conversion element according to the present invention includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer including an electron transport layer. In the present invention, a compound represented by the above formula (1) can be used as the electron transport material contained in the electron transport layer. The electron transport layer is preferably adjacent to the second electrode. The photoelectric conversion element may include other layers. Examples of other layers include, but are not limited to, layers used in photoelectric conversion elements. Examples include, but are not limited to, a light-receiving layer, a hole transport layer, a hole transport-enhancing layer, a hole-blocking layer, an electron-blocking layer, a buffer layer, etc.

[0015] The photoelectric conversion element according to the present invention has, for example, a first electrode, an electron transport layer, and a second electrode stacked in this order. Furthermore, the photoelectric conversion element may also have other layers, such as a buffer layer, interposed between the second electrode and the electron transport layer.

[0016] In one embodiment, the photoelectric conversion element according to the present invention has a first electrode, a hole transport layer, a light-receiving layer, an electron transport layer, and a second electrode stacked in this order. In another embodiment, the photoelectric conversion element according to the present invention has a first electrode, a hole transport enhancement layer, a hole transport layer, a light-receiving layer, an electron transport layer, and a second electrode stacked in this order. The above layers may be stacked adjacent to each other, or other layers may be interposed between any of the above layers.

[0017] The photoelectric conversion element may be subjected to light from either the first electrode side or the second electrode side, and either the first electrode or the second electrode may be a transparent electrode. For example, it may have a structure in which a transparent electrode (second electrode), electron transport layer, light receiving layer, hole transport layer, hole transport enhancement layer, and metal electrode (first electrode) are stacked in that order, or it may have a structure in which a transparent electrode (first electrode), hole transport enhancement layer, hole transport layer, light receiving layer, electron transport layer, and metal electrode (second electrode) are stacked in that order. Furthermore, both the first electrode and the second electrode may be transparent electrodes.

[0018] Next, we will explain the case where the organic electronic device is an organic EL device.

[0019] <Organic EL Element Structure> The organic EL element according to the present invention includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer including an electron transport layer. In the present invention, a compound represented by the above formula (1) can be used as the material contained in the electron transport layer. The electron transport layer is preferably adjacent to the second electrode. The organic EL element may include other layers. Other layers include layers generally used in organic EL elements. Examples include, but are not limited to, an emissive layer, a hole transport layer, a hole transport enhancement layer, a hole blocking layer, an electron blocking layer, a buffer layer, etc.

[0020] An organic EL element, for example, has a first electrode, an electron transport layer, and a second electrode stacked in that order. Alternatively, the organic EL element may have other layers, such as a buffer layer, interposed between the second electrode and the electron transport layer.

[0021] In one embodiment, the organic EL element has a first electrode, an emissive layer, an electron transport layer, and a second electrode stacked in this order. In another embodiment, the organic EL element according to the present invention has a first electrode, a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and a second electrode stacked in this order. The above layers may be stacked adjacent to each other, or other layers may be interposed between any of the above layers.

[0022] The organic EL element may extract light from either the first electrode side or the second electrode side, and either the first electrode or the second electrode may be a transparent electrode. For example, it may have a structure in which a transparent electrode (second electrode), electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and metal electrode (first electrode) are stacked in that order, or it may have a structure in which a transparent electrode (first electrode), hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and metal electrode (second electrode) are stacked in that order. Furthermore, both the first electrode and the second electrode may be transparent electrodes.

[0023] Next, we will describe the compound having the structure represented by formula (1) in the organic electronic device of the present invention.

[0024] <Compound represented by formula (1)> The organic layer in the organic electronic device of the present invention contains a compound represented by the following formula (1).

[0025]

[0026] In formula (1), R a Each of these independently represents a hydrogen atom, a hydroxyl group, a thiol group, an amino group, a cyano group, a carboxyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group.

[0027] In this specification, examples of linear, branched, or cyclic alkyl groups having 3 to 18 carbon atoms include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, cyclohexyl, or adamantyl groups. Furthermore, examples of aromatic hydrocarbon groups having 6 to 30 carbon atoms and heteroaromatic groups having 3 to 20 carbon atoms include phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, pyrazolyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenanthryl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, fluoranthenyl group, chrysenyl group, pyrenyl group, carbazolyl group, thienyl group, benzothienyl group, dibenzothienyl group, furyl group, benzofuranyl group, dibenzofuranyl group, imidazolyl group, benzimidazolyl group, thiazolyl group, benzothiazolyl group, oxazolyl group, benzoxazolyl group, phenothiazinyl group, phenoxazinyl group, and thianthrenyl group.

[0028] R aIn terms of ease of synthesis, methyl group, cyano group, cyanomethyl group, dicyanomethyl group, phenylcyanomethyl group, ethyl group, cyanoethyl group, fluoroethyl group, propyl group, bromopropyl group, butyl group, isobutyronitrile group, pentyl group, phenylpropionitrile group, methyl-phenylpropionitrile group, cyclohexyl group, cyanocyclohexyl group, cyclohexylisopropyl group, adamantyl group, adamantylmethyl group, adamantylisopropyl group, pentafluoropropyl group, phenyl group, methylphenyl group, ethylphenyl Group, propylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, pentylphenyl group, isopentylphenyl group, neopentylphenyl group, hexylphenyl group, octylphenyl group, decylphenyl group, dodecylphenyl group, cyclopentylphenyl group, cyclohexylphenyl group, triphenylsilylphenyl group, dimethylphenyl group, trimethylphenyl group, methoxyphenyl group, ethoxyphenyl group, propoxyphenyl group, isopropoxyphenyl group, butoxyphenyl group, isobutoxyphenyl group, pentyl Oxyphenyl group, isopentyloxyphenyl group, neopentyloxyphenyl group, hexyloxyphenyl group, octyloxyphenyl group, decyloxyphenyl group, dodecyloxyphenyl group, tetradecyloxyphenyl group, cyclohexyloxyphenyl group, phenoxyphenyl group, methoxyphenyl group, dimethoxyphenyl group, diethoxyphenyl group, trimethoxyphenyl group, cyanophenyl group, dicyanophenyl group, fluorophenyl group, difluorophenyl group, pentafluorophenyl group, (trifluoromethyl)phenyl group, bis( Trifluoromethyl)phenyl group, cyano-(trifluoromethyl)phenyl group, biphenyl group, terphenyl group, dicyanoterphenyl group, difluoroterphenyl group, bis(trifluoromethyl)terphenyl group, dinaphthylphenyl group, dipyridylphenyl group, naphthyl group, cyanonaphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diethylfluorenyl group, 9,9-di-n-propylfluorenyl group, 9,9-di-n-octylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9'-spirobifluorenyl group,Phenanthryl group, fluoranthenyl group, pyrenyl group, anthryl group, triphenylenyl group, chrysenyl group, perilenyl group, imidazolyl group, methylimidazolyl group, cyanoimidazolyl group, dicyanoimidazolyl group, dicyano-methylimidazolyl group, phenylimidazolyl group, dimethyl-phenylimidazolyl group, dicyano-phenylimidazolyl group, methylbenzo[d]imidazolyl group, phenylbenzo[d]imidazolyl group, cyano-methylbenzo[d]imidazolyl group, methylpyrazolyl group, phenylpyrazolyl group, thiazolyl group, isothiazolyl Calcium group, cyanothiazolyl group, dicyanothiazolyl group, (trifluoromethyl)thiazolyl group, cyanophenylthiazolyl group, benzo[d]thiazolyl group, cyanobenzo[d]thiazolyl group, (trifluoromethyl)benzo[d]thiazolyl group, oxazolyl group, isoxazolyl group, cyanooxazolyl group, dicyanooxazolyl group, (trifluoromethyl)oxazolyl group, cyanophenyloxazolyl group, benzo[d]oxazolyl group, cyanobenzo[d]oxazolyl group, (trifluoromethyl)benzo[d]oxazolyl group, pyridyl group, methyl Lupyridyl group, dimethylpyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, (trifluoromethyl)pyridyl group, bis(trifluoromethyl)pyridyl group, cyano-(trifluoromethyl)pyridyl group, terpyridyl group, diphenylpyridyl group, dicyanophenylpyridyl group, bis(trifluoromethyl)phenylpyridyl group, pyrazyl group, methylpyridyl group, cyanopyradyl group, fluoropyridyl group, (trifluoromethyl)pyridyl group, pyrimidyl group, methylpyridyl group dimethylpyrimidyl group, cyanopyrimidyl group, dicyanopyrimidyl group, fluoropyrimidyl group, difluoropyrimidyl group, (trifluoromethyl)pyrimidyl group, diphenylpyrimidyl group, triazyl group, diphenyltriazyl group, dipyridyltriazyl group, quinolyl group, isoquinolyl group, quinoxalyl group, phenylquinoxalyl group, dimethylquinoxalyl group, diphenylquinoxalyl group, quinazolyl group, acridinyl group, phenantrolyl group, thienyl group, benzothienyl group, dibenzothienyl group, furanyl group, benzofuranyl group, dibenzofuranyl group,A methylcarbazolyl group, a phenylcarbazolyl group, a thianthrenyl group, a phenothiazinyl group, a phenylphenothiazinyl group, a phenoxazinyl group, or a phenylphenoxazinyl group is preferred.

[0029] Also, R aThese include cyanomethyl group, phenylcyanomethyl group, cyanoethyl group, n-propyl group, n-butyl group, 3-pentyl group, isobutyronitrile group, phenylpropionitrile group, cyclohexyl group, 1-adamantyl group, 1-adamantylmethyl group, phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 3,5- Di-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-triphenylsilylphenyl group, 3-triphenylsilylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group Cyphenyl group, 4-neopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2-(2-ethylbutyl)oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl- 5-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methyl C-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 2-cyanophenyl group, 3,4-dicyanophenyl group, 3,5-dicyanophenyl group, 2,4-dicyanophenyl group, 2,5-dicyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, pentafluorophenyl group, 4-(trifluoromethyl)phenyl group, 3-(trifluoromethyl)phenyl group, 2-(trifluoromethyl)phenyl group, 3,5-bis(trifluoromethyl)phenyl group, 4-cyano-3-(trifluoromethyl)phenyl group, 2-(4-fluorophenyl)phenyl group, 2-(3-fluorophenyl)phenyl group, 2-(3,4-difluorophenyl)phenyl group, 2-(3,5-difluorophenyl)phenyl group, 2-(4-cyanophenyl)phenyl group, 2-(3-cyanophenyl 2-(3,4-dicyanophenyl)phenyl group, 2-(3,5-dicyanophenyl)phenyl group, 2-(4-cyanonaphthalene-1-yl)phenyl group, 2-(4-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 2-(4-quinolyl)phenyl group, 2-(5-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 2-(4-cyanophenyl)-4-cyanophenyl group, 2-(3-cyanophenyl)-4-phenyl group, 2-(4-cyanophenyl)-5-cyanophenyl group, 2-(3-cyanophenyl)-5-phenyl group 3,5-bis(4-cyanophenyl)phenyl group, 3,5-bis(3-cyanophenyl)phenyl group, 3,5-bis(4-fluorophenyl)phenyl group, 3,5-bis(1-naphthyl)phenyl group, 3,5-bis(2-naphthyl)phenyl group, 3,5-bis(3-pyridyl)phenyl group, 3,5-bis(4-pyridyl)phenyl group, 3,4-bis(4-cyanophenyl)phenyl group, 3,4-bis(3-cyanophenyl)phenyl group, 3,4-bis(4-fluorophenyl) Phenyl group, 3,4-bis(1-naphthyl)phenyl group, 3,4-bis(2-naphthyl)phenyl group, 3,4-bis(3-pyridyl)phenyl group, 3,4-bis(4-pyridyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 2-cyanonaphthalen-1-yl group, 4-cyanonaphthalen-1-yl group, 6-cyanonaphthalen-2-yl group, 4-(4-pyridyl)naphthalen-1-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group, 9,9-di-n-propyl-2-fluorenyl group, 9,9-di-n-octyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-4-fluorenyl group, 9,9'-spirobifloren-2-yl group, 9,9'-spirobifloren-4-yl group, 9-phenanthryl group, 2-phenanthryl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-pyrenyl group, 2-pyrenyl group, 9-anthryl group, 2-anthryl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-chrysenyl group , 6-crisenyl group, 3-perilenyl group, 1-imidazolyl group, 2-methyl-1-imidazolyl group, 2-methyl-3,4-dimethyl-1-imidazolyl group, 2-methyl-3,4-dicyano-1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2-phenyl-3,4-dicyano-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-dicyano-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dicyano-2-imidazolyl group, 1-methyl-2-benzo[d]imidazolyl group, 1-phenyl-2-benzo[d]imidazolyl group, 5-cyano-1-methyl-2-benzo[d]imidazolyl 4-Cyanol group, 6-Cyano-1-methyl-2-benzo[d]imidazolyl group, 1-Methyl-3-Pyrazolyl group, 1-Phenyl-3-Pyrazolyl group, 1-Methyl-4-Pyrazolyl group, 1-Phenyl-4-Pyrazolyl group, 1-Methyl-5-Pyrazolyl group, 1-Phenyl-5-Pyrazolyl group, 2-Thiazolyl group, 4-Thiazolyl group, 5-Thiazolyl group, 3-Isothiazolyl group, 4-Isothiazolyl group, 5-Isothiazolyl group, 4-Cyano-2-Thiazolyl group, 5-Cyano-2-Thiazolyl group, 4,5-dicyano-2-thiazolyl group, 4-trifluoromethyl-2-thiazolyl group, 5-trifluoromethyl-2-thiazolyl group, 4-cyano-5-phenyl-2-thiazolyl group, 5-cyano-4-phenyl-2-thiazolyl group, 2-benzo[d]thiazolyl group, 5-cyano-2-benzo[d]thiazolyl group, 6-cyano-2-benzo[d]thiazolyl group, 5-(trifluoromethyl)-2-benzo[d]thiazolyl group, 6-(trifluoromethyl)-2-benzo[d]thiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5- xazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 4-cyano-2-oxazolyl group, 5-cyano-2-oxazolyl group, 4,5-dicyano-2-oxazolyl group, 4-trifluoromethyl-2-oxazolyl group, 5-trifluoromethyl-2-oxazolyl group, 4-cyano-5-phenyl-2-oxazolyl group, 5-cyano-4-phenyl-2-oxazolyl group, 2-benzo[d]oxazolyl group, 5-cyano-2-benzo[d]oxazolyl group, 6-cyano-2-benzo[d]oxazolyl 5-(trifluoromethyl)-2-benzo[d]oxazolyl group, 6-(trifluoromethyl)-2-benzo[d]oxazolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-methyl-4-pyridyl group, 3-methyl-4-pyridyl group, 3,5-dimethyl-4-pyridyl group, 2-methyl-3-pyridyl group, 4-methyl-3-pyridyl group, 5-methyl-3-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 2-cyano-4-pyridyl group, 3-cyano-4-pyridyl group Dyl group, 3,5-dicyano-4-pyridyl group, 2-cyano-3-pyridyl group, 4-cyano-3-pyridyl group, 5-cyano-3-pyridyl group, 4,5-dicyano-3-pyridyl group, 3-cyano-2-pyridyl group, 4-cyano-2-pyridyl group, 5-cyano-2-pyridyl group, 2-fluoro-4-pyridyl group, 3-fluoro-4-pyridyl group, 3,5-difluoro-4-pyridyl group, 2,3,5,6-tetrafluoro-4-pyridyl group, 2-fluoro-3-pyridyl group, 4-fluoro-3-pyridyl group, 5-fluoro-3-pyridyl group, 4,5-difluoro-3-pyridyl group, 3-fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 2-trifluoromethyl-4-pyridyl group, 3-trifluoromethyl-4-pyridyl group, 3,5-bis(trifluoromethyl)-4-pyridyl group, 2-trifluoromethyl-3-pyridyl group, 4-trifluoromethyl-3-pyridyl group, 5-trifluoromethyl-3-pyridyl group, 4,5-bis(trifluoromethyl)-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group, 4-trif Luoromethyl-2-pyridyl group, 5-trifluoromethyl-2-pyridyl group, 4-cyano-5-trifluoromethyl-3-pyridyl group, 4-cyano-5-trifluoromethyl-2-pyridyl group, p-terpyridyl group, m-terpyridyl group, o-terpyridyl group, 3,5-diphenyl-4-pyridyl group, 3,5-bis(1-naphthyl)-4-pyridyl group, 3,5-bis(2-naphthyl)-4-pyridyl group, 3,5-bis(4-cyanophenyl)-4-pyridyl group, 3,5-bis(3-cyanophenyl)-4-pyridyl group, 3,5-bis (4-pyridyl)-4-pyridyl group, 3,5-bis(3-pyridyl)-4-pyridyl group, 4,5-diphenyl-3-pyridyl group, 4,5-bis(1-naphthyl)-3-pyridyl group, 4,5-bis(2-naphthyl)-3-pyridyl group, 4,5-bis(4-cyanophenyl)-3-pyridyl group, 4,5-bis(3-cyanophenyl)-3-pyridyl group, 4,5-bis(4-pyridyl)-3-pyridyl group, 4,5-bis(3-pyridyl)-3-pyridyl group, pyrazyl group, 5-methylpyrazine-2-yl group, 5-cyanopyrazine-2-yl Group, 5-fluoropyrazine-2-yl group, 5-(trifluoromethyl)pyrazine-2-yl group, 2-pyrimidyl group, 5-methylpyrimidine-2-yl group, 4,6-dimethylpyrimidine-2-yl group, 5-cyanopyrimidine-2-yl group, 4,6-dicyanopyrimidine-2-yl group, 5-fluoropyrimidine-2-yl group, 4,6-difluoropyrimidine-2-yl group, 5-(trifluoromethyl)pyrimidine-2-yl group, 4,6-diphenylpyrimidine-2-yl group, 4,6-bis(4-pyridyl)pyrimidine-2-yl group, 4,6-bis(3-pyridyl)pyrimidine-2-yl group, 5-pyrimidyl group, 2-methylpyrimidine-5-yl group, 2-tert-butylpyrimidine-5-yl group, 2-cyanopyrimidine-5-yl group, 2-fluoropyrimidine-5-yl group, 2-(trifluoromethyl)pyrimidine-5-yl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazine-2-yl group, 4,6-bis(4-pyridyl)-1,3,5-triazine-2-yl group 4,6-bis(3-pyridyl)-1,3,5-triazine-2-yl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-quinoxalyl group, 3-phenyl-2-quinoxalyl group, 6-quinoxalyl group, 2,3-dimethyl-6-quinoxalyl group, 2,3-diphenyl-6-quinoxalyl group, 2-quinazolyl group, 4-quinazolyl group Lyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, 9-methylcarbazole-2-yl It is even more preferable that the group is a 9-methylcarbazole-3-yl group, a 9-methylcarbazole-4-yl group, a 9-phenylcarbazole-2-yl group, a 9-phenylcarbazole-3-yl group, a 9-phenylcarbazole-4-yl group, a 2-thianthrenyl group, a 10-phenylphenothiazine-3-yl group, a 10-phenylphenothiazine-2-yl group, a 10-phenylphenoxazine-3-yl group, or a 10-phenylphenoxazine-2-yl group.

[0030] And R aExamples include cyanomethyl group, phenylcyanomethyl group, n-propyl group, n-butyl group, 3-pentyl group, isobutyronitrile group, phenylpropionitrile group, cyclohexyl group, adamantyl group, adamantylmethyl group, phenyl group, 4-methylphenyl group, 4-n-propylphenyl group, 4-tert-butylphenyl group, 3,5-di-tert-butylphenyl group, 4-triphenylsilylphenyl group, 4-methoxyphenyl group, 4-phenoxyphenyl group, 3,5-dimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 2-cyanophenyl group, 3,4-dicyanophenyl group, 3,5-dicyanophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, pentafluorophenyl group, 4-(trifluoromethyl)phenyl group, 3-(trifluoromethyl)phenyl group, 3,5-bis(trifluoromethyl)phenyl group, 4-cyano-3-(trifluoromethyl)phenyl group, 2-(4-fluorophenyl)phenyl group, 2-(3-fluorophenyl)phenyl group, 2-(3,5-difluorophenyl)phenyl group, 2-(4-cyanophenyl)phenyl group, 2-(3-cyanophenyl)phenyl group, 2-(3,4-dicyanophenyl)phenyl group, 2-(3,5-dicyanophenyl)phenyl group, 2-(4-cyanonaphthalene-1-yl)phenyl group, 2-(4-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 2-(4-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 2-(4-cyanophenyl)-4-cyanophenyl group, 2-(3-cyanophenyl)-4-phenyl group, 2-(4-cyanophenyl)-5-cyanophenyl group, 2-(3-cyanophenyl)-5-phenyl group, m -Terphenyl group, o-Terphenyl group, 3,5-bis(4-cyanophenyl)phenyl group, 3,5-bis(3-cyanophenyl)phenyl group, 3,5-bis(3-pyridyl)phenyl group, 3,5-bis(4-pyridyl)phenyl group, 3,4-bis(4-cyanophenyl)phenyl group, 3,4-bis(3-cyanophenyl)phenyl group, 3,4-bis(3-pyridyl)phenyl group, 3,4-bis(4-pyridyl)phenyl group, 1-Naphthyl group, 2-Naphthyl group, 4-Cyanonaphthalen-1-yl group, 4-(4-pyridyl)naphthalen-1-yl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9'-spirobifluoren-2-yl group, 9-phenanthryl group, 2-triphenylenyl group, 3-fluoranthenyl group, 1-methyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4,5-dicyano-2-imidazolyl group, 1-phenyl-4,5-dicyano-2-imidazolyl group, 1-methyl-2-benzo[d]imidazolyl group, 1-phenyl-2-benzo[d]imidazolyl group, 4-cyano-2- Azolyl group, 5-cyano-2-thiazolyl group, 4-trifluoromethyl-2-thiazolyl group, 2-benzo[d]thiazolyl group, 4-cyano-2-oxazolyl group, 5-cyano-2-oxazolyl group, 4-trifluoromethyl-2-oxazolyl group, 2-benzo[d]oxazolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 3-cyano-4-pyridyl group, 3,5-dicyano-4-pyridyl group, 4-cyano-3-pyridyl group, 5-cyano-3-pyridyl group, 4-cyano-2-pyridyl group, 3-fluoro-4-pyridyl group, 3,5-difluoro-4 - Pyridyl group, 2,3,5,6-tetrafluoro-4-pyridyl group, 4-fluoro-3-pyridyl group, 3-trifluoromethyl-4-pyridyl group, 3,5-bis(trifluoromethyl)-4-pyridyl group, 4-trifluoromethyl-3-pyridyl group, 4-trifluoromethyl-2-pyridyl group, 4-cyano-5-trifluoromethyl-3-pyridyl group, m-terpyridyl group, o-terpyridyl group, 3,5-diphenyl-4-pyridyl group, 3,5-bis(4-cyanophenyl)-4-pyridyl group, 3,5-bis(3-cyanophenyl)-4-pyridyl group, 3, 5-bis(4-pyridyl)-4-pyridyl group, 3,5-bis(3-pyridyl)-4-pyridyl group, 4,5-diphenyl-3-pyridyl group, 4,5-bis(4-cyanophenyl)-3-pyridyl group, 4,5-bis(3-cyanophenyl)-3-pyridyl group, 4,5-bis(4-pyridyl)-3-pyridyl group, 4,5-bis(3-pyridyl)-3-pyridyl group, pyrazyl group, 5-cyanopyridine-2-yl group, 2-pyrimidyl group, 4,6-dimethylpyrimidine-2-yl group, 5-cyanopyrimidine-2-yl group, 4,6-diphenylpyrimidine-2-yl group, 4,6-bis(4-pyridyl)pyrimidine-2-yl group, 4,6-bis(3-pyridyl)pyrimidine-2-yl group, 5-pyrimidyl group, 2-cyanopyrimidine-5-yl group, 2-(trifluoromethyl)pyrimidine-5-yl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazine-2-yl group, 4,6-bis(4-pyridyl)-1,3,5-triazine- Particularly preferred are 2-yl groups, 4,6-bis(3-pyridyl)-1,3,5-triazine-2-yl groups, 4-quinolyl groups, 5-quinolyl groups, 8-quinolyl groups, 6-quinoxalyl groups, 2-quinazolyl groups, 4-quinazolyl groups, 1,10-phenanthroline-5-yl groups, 2-dibenzothienyl groups, 4-dibenzothienyl groups, 2-dibenzofuranyl groups, or 4-dibenzofuranyl groups.

[0031] n represents an integer between 0 and 2. When n is 2, Ra may be the same or different. For ease of composition, n is preferably 1 or 2, and particularly preferably 1.

[0032] L １ This represents a single bond, a linear, branched, or cyclic (n+1) valency aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n+1) valency aromatic hydrocarbon group having 6 to 18 carbon atoms, or an (n+1) valency heteroaromatic group having 3 to 20 carbon atoms. The aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings.

[0033] L １ From the viewpoint of device performance, the group is preferably a single bond, (n+1) valent benzene, (n+1) valent naphthalene, (n+1) valent pyridine, or (n+1) valent pyrimidine, with a single bond, (n+1) valent benzene, or (n+1) valent pyridine being particularly preferred, and a single bond, divalent benzene (1,4-phenylene group, 1,3-phenylene group, or 1,2-phenylene group) or divalent pyridine (3,4-pyridylene group, 2,5-pyridylene group, or 2,6-pyridylene group) being even more preferred. These groups may have substituents, and preferred substituents are methyl groups, cyano groups, fluoro groups, or trifluoromethyl groups.

[0034] R １ ~R ６ Each of these independently represents a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, an iodo group, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups. From the viewpoint of synthesis and device performance, R １ and R ２ Each of these is preferably independently a hydrogen atom, a phenyl group, or a naphthyl group. ３ , R ４ and R ６ is a hydrogen atom, R ５ It is preferable that the group is one of the following: a hydrogen atom, a cyano group, a trifluoromethyl group, a methoxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a phenyl group, or a pyridyl group.

[0035] R a , L １ , and R １ ~R ６ In this context, preferred substituents that may be present are, independently, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, a linear, branched, or cyclic alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or combinations thereof. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group.

[0036] In terms of ease of synthesis, R a , L １ , and R １ ~R ６In this, the substituents that may be present are more preferably a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, an isopropyl group, a tert-butyl group, a phenoxy group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a (trifluoromethyl)phenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, or a (trifluoromethyl)pyridyl group, and particularly preferably a cyano group, a fluoro group, a trifluoromethyl group, a methyl group, a tert-butyl group, a phenoxy group, a phenyl group, a cyanophenyl group, a (trifluoromethyl)phenyl group, a pyridyl group, a cyanopyridyl group, or a (trifluoromethyl)pyridyl group.

[0037] The organic electronic element of the present invention is not particularly limited, but examples include organic EL elements and photoelectric conversion elements (solar cells, photodiodes, photoelectric conversion elements for image sensors, etc.). Photoelectric conversion elements are preferred as the organic electronic element, and photoelectric conversion elements for image sensors are more preferred.

[0038] The compound represented by formula (1) is used as part of an organic electronic device. While not particularly limited, examples of parts of an organic electronic device include electron transport layers, light-emitting layers, light-receiving layers, hole injection layers, and hole transport-enhancing layers. Among these, the compound represented by formula (1) is preferably used in the electron transport layer.

[0039] Preferred examples of imide compounds represented by formula (1) include, for example, (A1) to (A324) below. However, the compounds of the present invention are not limited to these.

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] Of the above, (A1) to (A21), (A28), (A31) to (A67), (A76) to (A79), (A91) to (A103), (A108) to (A109), (A116) to (A131), (A136) to (A145), (A147) to (A175), (A178) to (A204), and (A280) to (A324) are even more preferable in order to enhance interaction with adjacent layers such as the light-receiving layer. Furthermore, from the viewpoint of smoothness during film formation, (A1), (A2), (A3), (A7), (A9), (A12), (A13), (A16), (A18), (A19), (A20), (A21), (A28), (A31), (A34), (A35), (A39), (A41), (A43), (A46), (A52), (A57), (A65), (A77), (A79), (A92), (A93), (A94), (A97), (A100), (A103), (A118), (A119), (A120), (A121), (A122), (A123) (A124), (A129), (A131), (A137), (A138), (A141), (A142), (A143), (A147), (A148), (A149), (A150), (A157), (A161), (A162), (A170), (A172), (A189), (A192), (A193), (A195), (A196), (A197), (A198), (A272), (A275), (A282), (A284), (A286), (A296), (A309), (A318), and (A324) are particularly preferred.

[0063] A more preferred embodiment of the imide compound represented by formula (1) above is the compound represented by the following formula (X-1). (In formula (X-1), R Ｘ１ and R Ｘ２ Each of these is independently either a hydrogen atom or a phenyl group. Ｘ１ R is a single bond, (n+1)-valent benzene or (n+1)-valent pyridine, and may have a cyano group as a substituent. Ｘａn represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms, which may have a cyano group, a fluoro group, a trifluoromethyl group, a linear, branched, or cyclic alkyl group having 2 to 10 carbon atoms, or a combination of these groups as a substituent. (n represents an integer from 0 to 2.)

[0064] R Ｘ１ and R Ｘ２ These may be the same or different, but it is particularly preferable that they be the same in that they are easy to synthesize. Ｘ１ In terms of ease of synthesis, single-bonded or divalent benzene (1,4-phenylene group, 1,3-phenylene group, or 1,2-phenylene group) is more preferred, and single-bonded benzene is particularly preferred. When n is 2, Ra may be the same or different. In terms of ease of synthesis, n is preferably 1 or 2, and particularly preferred to be 1.

[0065] R Ｘａ For example, (R1) to (R32) below are listed as preferred examples. However, R Ｘａ This is not limited to these. Note that * in the following formula represents L Ｘ１ (L Ｘ１ When it is a single bond, it represents the bond with N).

[0066] From the perspective of enhancing interaction with adjacent layers such as the light-receiving layer, R Ｘａ Of the above, (R1) to (R6), (R22) to (R25), and (R31) to (R32) are particularly preferred.

[0067] [Manufacturing Method] The compound represented by formula (1) can be synthesized by known methods or combinations thereof. For example, a compound represented by formula (12) can be obtained by reacting an acid anhydride derivative represented by formula (1b) with an amine compound represented by formula (11).

[0068] (In the formula, R ａ , L １ , R １ ~R ６(and n have the same definition as in formula (1) above.) The amine compound represented by formula (11) above may be a commercially available product, or it can be synthesized by combining conventionally known coupling reactions (for example, Journal of Organic Chemistry (2009), 74(8), 3225-3228). Examples of coupling reactions here include the Suzuki coupling reaction, Still coupling reaction, Kumada coupling reaction, and Hiyama coupling reaction, with the Suzuki coupling reaction being preferred because it yields a product of high purity.

[0069] The above reaction may be carried out in a reaction solvent, and preferred examples of reaction solvents include: haloalkanes such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, and tetrachloroethane; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; heteroaromatic compounds such as imidazole, pyridine, pyrazine, and quinoline; and carbonate esters such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate. Examples of solvents include esters such as ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); sulfoxides such as dimethyl sulfoxide (DMSO); alcohols such as methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; and phenols such as phenol, naphthol, and cresol. These can be used individually or in any ratio, and there are no particular restrictions on the amount of solvent used. Among these, chloroform, xylene, DMF, DMAc, pyridine, quinoline, and mixed solvents thereof are preferred in terms of good reaction yield.

[0070] Furthermore, the above reaction can be accelerated by carrying it out in the presence of a condensing agent. Examples of such condensing agents include solid acids such as alumina and silica gel; metal chlorides such as titanium tetrachloride, tin tetrachloride, and antimony pentachloride; organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, diazabicycloundecene, tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane; and carbodiimides such as 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, and 1,1'-carbonyldi(1,2,4-triazole). Among these, triethylamine, pyridine, or EDC are more preferred as condensing agents because they yield a good reaction yield of the compound represented by formula (2).

[0071] The amount of condensing agent used is preferably in the range of 0.1 to 10 moles, and more preferably in the range of 0.5 to 5 moles, per mole of the compound represented by formula (2) above.

[0072] The reaction temperature and reaction time vary depending on the amount of organic solvent and condensing agent used, but are usually selected from the ranges of -50 to 250°C and 1 to 48 hours, respectively. A reaction temperature of -20°C or higher is preferable for sufficient reaction, and a temperature of 180°C or lower is preferable for economic reasons. A reaction time of 1 to 24 hours is preferable.

[0073] <<Effects of Compounds Having the Structure Represented by Formula (1)>> Compounds having the structure represented by formula (1) have an imide structure containing a fluorene ring, and due to this strong acceptor skeleton, they have a deep LUMO level. This increases electron acceptivity, allowing electrons generated in the photodetector layer to be received with a small energy barrier. Thus, because compounds represented by formula (1) have a deep LUMO level, it is expected that electron exchange between the photodetector layer and the electrode will be smoother. Furthermore, the compound of this application is also characterized by a wide energy gap and a deep HOMO level. This is expected to suppress reverse charge injection from the electrode and improve hole blocking from the photodetector layer, and when used for image sensors, for example, it is expected to reduce dark current or improve external quantum efficiency. In addition, because compounds represented by formula (1) have an imide structure containing a fluorene ring, thermal stability and high reduction resistance can also be expected.

[0074] As described above, the inventors have found that the compound represented by formula (1) can be effectively used as an electron transport material to facilitate the exchange of electrons between the light-receiving layer and the electrode. They have also confirmed that when the compound represented by formula (1) (electron transport material) is actually used in a photoelectric conversion element, its electron transport capability is enhanced. In other words, they have confirmed that the energy barrier when extracting carriers generated in the light-receiving layer to the electrode side in a photoelectric conversion element can be reduced by the compound represented by formula (1), which is the electron transport material of this application.

[0075] (Imide Compounds) The present invention relates to imide compounds represented by the following formula (2). In formula (2), R ｂ Each of these independently represents a hydrogen atom, a hydroxyl group, a thiol group, an amino group, a cyano group, a carboxyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. However, L ２ If it is a single bond, R ｂis anything other than a phenyl group (limited to phenyl groups without substituents). That is, L ２ If it is a single bond, R ｂ (L) may be a phenyl group having a substituent, but not a phenyl group without a substituent. ２ If it is a single bond, R ｂ (It does not have a phenyl group that does not have a substituent.)

[0076] R ｂ Examples of these groups, independently, include alkyl groups, cycloalkyl groups, adamantyl groups, phenyl groups, biphenyl groups, terphenyl groups, fluorenyl groups, naphthyl groups, phenanthryl groups, pyridyl groups, bipyridyl groups, terpyridyl groups, pyrazyl groups, pyrimidyl groups, triazyl groups, quinolyl groups, quinoxalinyl groups, quinazolyl groups, imidazolyl groups, benzimidazolyl groups, thiazolyl groups, benzothiazolyl groups, oxazolyl groups, or benzoxazolyl groups, and these groups may have substituents.

[0077] R ｂIn terms of ease of synthesis, methyl group, cyano group, cyanomethyl group, dicyanomethyl group, phenylcyanomethyl group, ethyl group, cyanoethyl group, fluoroethyl group, propyl group, bromopropyl group, butyl group, isobutyronitrile group, pentyl group, phenylpropionitrile group, methyl-phenylpropionitrile group, cyclohexyl group, cyanocyclohexyl group, cyclohexylisopropyl group, adamantyl group, adamantylmethyl group, adamantylisopropyl group, pentafluoropropyl group, phenyl group, methylphenyl group, ethylphenyl Group, propylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, pentylphenyl group, isopentylphenyl group, neopentylphenyl group, hexylphenyl group, octylphenyl group, decylphenyl group, dodecylphenyl group, cyclopentylphenyl group, cyclohexylphenyl group, triphenylsilylphenyl group, dimethylphenyl group, trimethylphenyl group, methoxyphenyl group, ethoxyphenyl group, propoxyphenyl group, isopropoxyphenyl group, butoxyphenyl group, isobutoxyphenyl group, pentyl Oxyphenyl group, isopentyloxyphenyl group, neopentyloxyphenyl group, hexyloxyphenyl group, octyloxyphenyl group, decyloxyphenyl group, dodecyloxyphenyl group, tetradecyloxyphenyl group, cyclohexyloxyphenyl group, phenoxyphenyl group, methoxyphenyl group, dimethoxyphenyl group, diethoxyphenyl group, trimethoxyphenyl group, cyanophenyl group, dicyanophenyl group, fluorophenyl group, difluorophenyl group, pentafluorophenyl group, (trifluoromethyl)phenyl group, bis( Trifluoromethyl)phenyl group, cyano-(trifluoromethyl)phenyl group, biphenyl group, terphenyl group, dicyanoterphenyl group, difluoroterphenyl group, bis(trifluoromethyl)terphenyl group, dinaphthylphenyl group, dipyridylphenyl group, naphthyl group, cyanonaphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diethylfluorenyl group, 9,9-di-n-propylfluorenyl group, 9,9-di-n-octylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9'-spirobifluorenyl group,Phenanthryl group, fluoranthenyl group, pyrenyl group, anthryl group, triphenylenyl group, chrysenyl group, perilenyl group, imidazolyl group, methylimidazolyl group, cyanoimidazolyl group, dicyanoimidazolyl group, dicyano-methylimidazolyl group, phenylimidazolyl group, dimethyl-phenylimidazolyl group, dicyano-phenylimidazolyl group, methylbenzo[d]imidazolyl group, phenylbenzo[d]imidazolyl group, cyano-methylbenzo[d]imidazolyl group, methylpyrazolyl group, phenylpyrazolyl group, thiazolyl group, isothiazolyl Calcium group, cyanothiazolyl group, dicyanothiazolyl group, (trifluoromethyl)thiazolyl group, cyanophenylthiazolyl group, benzo[d]thiazolyl group, cyanobenzo[d]thiazolyl group, (trifluoromethyl)benzo[d]thiazolyl group, oxazolyl group, isoxazolyl group, cyanooxazolyl group, dicyanooxazolyl group, (trifluoromethyl)oxazolyl group, cyanophenyloxazolyl group, benzo[d]oxazolyl group, cyanobenzo[d]oxazolyl group, (trifluoromethyl)benzo[d]oxazolyl group, pyridyl group, methyl Lupyridyl group, dimethylpyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, (trifluoromethyl)pyridyl group, bis(trifluoromethyl)pyridyl group, cyano-(trifluoromethyl)pyridyl group, terpyridyl group, diphenylpyridyl group, dicyanophenylpyridyl group, bis(trifluoromethyl)phenylpyridyl group, pyrazyl group, methylpyridyl group, cyanopyradyl group, fluoropyridyl group, (trifluoromethyl)pyridyl group, pyrimidyl group, methylpyridyl group dimethylpyrimidyl group, cyanopyrimidyl group, dicyanopyrimidyl group, fluoropyrimidyl group, difluoropyrimidyl group, (trifluoromethyl)pyrimidyl group, diphenylpyrimidyl group, triazyl group, diphenyltriazyl group, dipyridyltriazyl group, quinolyl group, isoquinolyl group, quinoxalyl group, phenylquinoxalyl group, dimethylquinoxalyl group, diphenylquinoxalyl group, quinazolyl group, acridinyl group, phenantrolyl group, thienyl group, benzothienyl group, dibenzothienyl group, furanyl group, benzofuranyl group, dibenzofuranyl group,A methylcarbazolyl group, a phenylcarbazolyl group, a thianthrenyl group, a phenothiazinyl group, a phenylphenothiazinyl group, a phenoxazinyl group, or a phenylphenoxazinyl group is preferred.

[0078] Also, R ｂThese include cyanomethyl group, phenylcyanomethyl group, cyanoethyl group, n-propyl group, n-butyl group, isobutyronitrile group, 3-pentyl group, phenylpropionitrile group, cyclohexyl group, 1-adamantyl group, 1-adamantylmethyl group, phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 3,5- Di-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-triphenylsilylphenyl group, 3-triphenylsilylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group Cyphenyl group, 4-neopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2-(2-ethylbutyl)oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl- 5-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methyl C-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 2-cyanophenyl group, 3,4-dicyanophenyl group, 3,5-dicyanophenyl group, 2,4-dicyanophenyl group, 2,5-dicyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, pentafluorophenyl group, 4-(trifluoromethyl)phenyl group, 3-(trifluoromethyl)phenyl group, 2-(trifluoromethyl)phenyl group, 3,5-bis(trifluoromethyl)phenyl group, 4-cyano-3-(trifluoromethyl)phenyl group, 2-(4-fluorophenyl)phenyl group, 2-(3-fluorophenyl)phenyl group, 2-(3,4-difluorophenyl)phenyl group, 2-(3,5-difluorophenyl)phenyl group, 2-(4-cyanophenyl)phenyl group, 2-(3-cyanophenyl 2-(3,4-dicyanophenyl)phenyl group, 2-(3,5-dicyanophenyl)phenyl group, 2-(4-cyanonaphthalene-1-yl)phenyl group, 2-(4-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 2-(4-quinolyl)phenyl group, 2-(5-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 2-(4-cyanophenyl)-4-cyanophenyl group, 2-(3-cyanophenyl)-4-phenyl group, 2-(4-cyanophenyl)-5-cyanophenyl group, 2-(3-cyanophenyl)-5-phenyl group 3,5-bis(4-cyanophenyl)phenyl group, 3,5-bis(3-cyanophenyl)phenyl group, 3,5-bis(4-fluorophenyl)phenyl group, 3,5-bis(1-naphthyl)phenyl group, 3,5-bis(2-naphthyl)phenyl group, 3,5-bis(3-pyridyl)phenyl group, 3,5-bis(4-pyridyl)phenyl group, 3,4-bis(4-cyanophenyl)phenyl group, 3,4-bis(3-cyanophenyl)phenyl group, 3,4-bis(4-fluorophenyl) Phenyl group, 3,4-bis(1-naphthyl)phenyl group, 3,4-bis(2-naphthyl)phenyl group, 3,4-bis(3-pyridyl)phenyl group, 3,4-bis(4-pyridyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 2-cyanonaphthalen-1-yl group, 4-cyanonaphthalen-1-yl group, 6-cyanonaphthalen-2-yl group, 2-fluorenyl group, 4-(4-pyridyl)naphthalen-1-yl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group, 9,9-di-n-propyl-2-fluorenyl group, 9,9-di-n-octyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-4-fluorenyl group, 9,9'-spirobifloren-2-yl group, 9,9'-spirobifloren-4-yl group, 9-phenanthryl group, 2-phenanthryl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-pyrenyl group, 2-pyrenyl group, 9-anthryl group, 2-anthryl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-chrysenyl group , 6-crisenyl group, 3-perilenyl group, 1-imidazolyl group, 2-methyl-1-imidazolyl group, 2-methyl-3,4-dimethyl-1-imidazolyl group, 2-methyl-3,4-dicyano-1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2-phenyl-3,4-dicyano-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-dicyano-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dicyano-2-imidazolyl group, 1-methyl-2-benzo[d]imidazolyl group, 1-phenyl-2-benzo[d]imidazolyl group, 5-cyano-1-methyl-2-benzo[d]imidazolyl 4-Cyanol group, 6-Cyano-1-methyl-2-benzo[d]imidazolyl group, 1-Methyl-3-Pyrazolyl group, 1-Phenyl-3-Pyrazolyl group, 1-Methyl-4-Pyrazolyl group, 1-Phenyl-4-Pyrazolyl group, 1-Methyl-5-Pyrazolyl group, 1-Phenyl-5-Pyrazolyl group, 2-Thiazolyl group, 4-Thiazolyl group, 5-Thiazolyl group, 3-Isothiazolyl group, 4-Isothiazolyl group, 5-Isothiazolyl group, 4-Cyano-2-Thiazolyl group, 5-Cyano-2-Thiazolyl group, 4,5-dicyano-2-thiazolyl group, 4-trifluoromethyl-2-thiazolyl group, 5-trifluoromethyl-2-thiazolyl group, 4-cyano-5-phenyl-2-thiazolyl group, 5-cyano-4-phenyl-2-thiazolyl group, 2-benzo[d]thiazolyl group, 5-cyano-2-benzo[d]thiazolyl group, 6-cyano-2-benzo[d]thiazolyl group, 5-(trifluoromethyl)-2-benzo[d]thiazolyl group, 6-(trifluoromethyl)-2-benzo[d]thiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5- xazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 4-cyano-2-oxazolyl group, 5-cyano-2-oxazolyl group, 4,5-dicyano-2-oxazolyl group, 4-trifluoromethyl-2-oxazolyl group, 5-trifluoromethyl-2-oxazolyl group, 4-cyano-5-phenyl-2-oxazolyl group, 5-cyano-4-phenyl-2-oxazolyl group, 2-benzo[d]oxazolyl group, 5-cyano-2-benzo[d]oxazolyl group, 6-cyano-2-benzo[d]oxazolyl 5-(trifluoromethyl)-2-benzo[d]oxazolyl group, 6-(trifluoromethyl)-2-benzo[d]oxazolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-methyl-4-pyridyl group, 3-methyl-4-pyridyl group, 3,5-dimethyl-4-pyridyl group, 2-methyl-3-pyridyl group, 4-methyl-3-pyridyl group, 5-methyl-3-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 2-cyano-4-pyridyl group, 3-cyano-4-pyridyl group Dyl group, 3,5-dicyano-4-pyridyl group, 2-cyano-3-pyridyl group, 4-cyano-3-pyridyl group, 5-cyano-3-pyridyl group, 4,5-dicyano-3-pyridyl group, 3-cyano-2-pyridyl group, 4-cyano-2-pyridyl group, 5-cyano-2-pyridyl group, 2-fluoro-4-pyridyl group, 3-fluoro-4-pyridyl group, 3,5-difluoro-4-pyridyl group, 2,3,5,6-tetrafluoro-4-pyridyl group, 2-fluoro-3-pyridyl group, 4-fluoro-3-pyridyl group, 5-fluoro-3-pyridyl group, 4,5-difluoro-3-pyridyl group, 3-fluoro-2-pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 2-trifluoromethyl-4-pyridyl group, 3-trifluoromethyl-4-pyridyl group, 3,5-bis(trifluoromethyl)-4-pyridyl group, 2-trifluoromethyl-3-pyridyl group, 4-trifluoromethyl-3-pyridyl group, 5-trifluoromethyl-3-pyridyl group, 4,5-bis(trifluoromethyl)-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group, 4-trif Luoromethyl-2-pyridyl group, 5-trifluoromethyl-2-pyridyl group, 4-cyano-5-trifluoromethyl-3-pyridyl group, 4-cyano-5-trifluoromethyl-2-pyridyl group, p-terpyridyl group, m-terpyridyl group, o-terpyridyl group, 3,5-diphenyl-4-pyridyl group, 3,5-bis(1-naphthyl)-4-pyridyl group, 3,5-bis(2-naphthyl)-4-pyridyl group, 3,5-bis(4-cyanophenyl)-4-pyridyl group, 3,5-bis(3-cyanophenyl)-4-pyridyl group, 3,5-bis (4-pyridyl)-4-pyridyl group, 3,5-bis(3-pyridyl)-4-pyridyl group, 4,5-diphenyl-3-pyridyl group, 4,5-bis(1-naphthyl)-3-pyridyl group, 4,5-bis(2-naphthyl)-3-pyridyl group, 4,5-bis(4-cyanophenyl)-3-pyridyl group, 4,5-bis(3-cyanophenyl)-3-pyridyl group, 4,5-bis(4-pyridyl)-3-pyridyl group, 4,5-bis(3-pyridyl)-3-pyridyl group, pyrazyl group, 5-methylpyrazine-2-yl group, 5-cyanopyrazine-2-yl Group, 5-fluoropyrazine-2-yl group, 5-(trifluoromethyl)pyrazine-2-yl group, 2-pyrimidyl group, 5-methylpyrimidine-2-yl group, 4,6-dimethylpyrimidine-2-yl group, 5-cyanopyrimidine-2-yl group, 4,6-dicyanopyrimidine-2-yl group, 5-fluoropyrimidine-2-yl group, 4,6-difluoropyrimidine-2-yl group, 5-(trifluoromethyl)pyrimidine-2-yl group, 4,6-diphenylpyrimidine-2-yl group, 4,6-bis(4-pyridyl)pyrimidine-2-yl group, 4,6-bis(3-pyridyl)pyrimidine-2-yl group, 5-pyrimidyl group, 2-methylpyrimidine-5-yl group, 2-tert-butylpyrimidine-5-yl group, 2-cyanopyrimidine-5-yl group, 2-fluoropyrimidine-5-yl group, 2-(trifluoromethyl)pyrimidine-5-yl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazine-2-yl group, 4,6-bis(4-pyridyl)-1,3,5-triazine-2-yl group 4,6-bis(3-pyridyl)-1,3,5-triazine-2-yl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-quinoxalyl group, 3-phenyl-2-quinoxalyl group, 6-quinoxalyl group, 2,3-dimethyl-6-quinoxalyl group, 2,3-diphenyl-6-quinoxalyl group, 2-quinazolyl group, 4-quinazolyl group Lyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, 9-methylcarbazole-2-yl It is even more preferable that the group is a 9-methylcarbazole-3-yl group, a 9-methylcarbazole-4-yl group, a 9-phenylcarbazole-2-yl group, a 9-phenylcarbazole-3-yl group, a 9-phenylcarbazole-4-yl group, a 2-thianthrenyl group, a 10-phenylphenothiazine-3-yl group, a 10-phenylphenothiazine-2-yl group, a 10-phenylphenoxazine-3-yl group, or a 10-phenylphenoxazine-2-yl group.

[0079] And R ｂExamples include cyanomethyl group, phenylcyanomethyl group, n-propyl group, n-butyl group, isobutyronitrile group, 3-pentyl group, phenylpropionitrile group, cyclohexyl group, adamantyl group, adamantylmethyl group, phenyl group, 4-methylphenyl group, 4-n-propylphenyl group, 4-tert-butylphenyl group, 3,5-di-tert-butylphenyl group, 4-triphenylsilylphenyl group, 4-methoxyphenyl group, 4-phenoxyphenyl group, 3,5-dimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 2-cyanophenyl group, 3,4-dicyanophenyl group, 3,5-dicyanophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, pentafluorophenyl group, 4-(trifluoromethyl)phenyl group, 3-(trifluoromethyl)phenyl group, 3,5-bis(trifluoromethyl)phenyl group, 4-cyano-3-(trifluoromethyl)phenyl group, 2-(4-fluorophenyl)phenyl group, 2-(3-fluorophenyl)phenyl group, 2-(3,5-difluorophenyl)phenyl group, 2-(4-cyanophenyl)phenyl group, 2-(3-cyanophenyl)phenyl group, 2-(3,4-dicyanophenyl)phenyl group, 2-(3,5-dicyanophenyl)phenyl group, 2-(4-cyanonaphthalene-1-yl)phenyl group, 2-(4-pyridyl)phenyl group, 2-(3-pyridyl)phenyl group, 2-(4-quinolyl)phenyl group, 2-(8-quinolyl)phenyl group, 2-(4-cyanophenyl)-4-cyanophenyl group, 2-(3-cyanophenyl)-4-phenyl group, 2-(4-cyanophenyl)-5-cyanophenyl group, 2-(3-cyanophenyl)-5-phenyl group, m -Terphenyl group, o-Terphenyl group, 3,5-bis(4-cyanophenyl)phenyl group, 3,5-bis(3-cyanophenyl)phenyl group, 3,5-bis(3-pyridyl)phenyl group, 3,5-bis(4-pyridyl)phenyl group, 3,4-bis(4-cyanophenyl)phenyl group, 3,4-bis(3-cyanophenyl)phenyl group, 3,4-bis(3-pyridyl)phenyl group, 3,4-bis(4-pyridyl)phenyl group, 1-Naphthyl group, 2-Naphthyl group, 4-Cyanonaphthalen-1-yl group, 4-(4-pyridyl)naphthalen-1-yl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9'-spirobifluoren-2-yl group, 9-phenanthryl group, 2-triphenylenyl group, 3-fluoranthenyl group, 1-methyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4,5-dicyano-2-imidazolyl group, 1-phenyl-4,5-dicyano-2-imidazolyl group, 1-methyl-2-benzo[d]imidazolyl group, 1-phenyl-2-benzo[d]imidazolyl group, 4-cyano-2- Azolyl group, 5-cyano-2-thiazolyl group, 4-trifluoromethyl-2-thiazolyl group, 2-benzo[d]thiazolyl group, 4-cyano-2-oxazolyl group, 5-cyano-2-oxazolyl group, 4-trifluoromethyl-2-oxazolyl group, 2-benzo[d]oxazolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 3-cyano-4-pyridyl group, 3,5-dicyano-4-pyridyl group, 4-cyano-3-pyridyl group, 5-cyano-3-pyridyl group, 4-cyano-2-pyridyl group, 3-fluoro-4-pyridyl group, 3,5-difluoro-4 - Pyridyl group, 2,3,5,6-tetrafluoro-4-pyridyl group, 4-fluoro-3-pyridyl group, 3-trifluoromethyl-4-pyridyl group, 3,5-bis(trifluoromethyl)-4-pyridyl group, 4-trifluoromethyl-3-pyridyl group, 4-trifluoromethyl-2-pyridyl group, 4-cyano-5-trifluoromethyl-3-pyridyl group, m-terpyridyl group, o-terpyridyl group, 3,5-diphenyl-4-pyridyl group, 3,5-bis(4-cyanophenyl)-4-pyridyl group, 3,5-bis(3-cyanophenyl)-4-pyridyl group, 3, 5-bis(4-pyridyl)-4-pyridyl group, 3,5-bis(3-pyridyl)-4-pyridyl group, 4,5-diphenyl-3-pyridyl group, 4,5-bis(4-cyanophenyl)-3-pyridyl group, 4,5-bis(3-cyanophenyl)-3-pyridyl group, 4,5-bis(4-pyridyl)-3-pyridyl group, 4,5-bis(3-pyridyl)-3-pyridyl group, pyrazyl group, 5-cyanopyridine-2-yl group, 2-pyrimidyl group, 4,6-dimethylpyrimidine-2-yl group, 5-cyanopyrimidine-2-yl group, 4,6-diphenylpyrimidine-2-yl group, 4,6-bis(4-pyridyl)pyrimidine-2-yl group, 4,6-bis(3-pyridyl)pyrimidine-2-yl group, 5-pyrimidyl group, 2-cyanopyrimidine-5-yl group, 2-(trifluoromethyl)pyrimidine-5-yl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazine-2-yl group, 4,6-bis(4-pyridyl)-1,3,5-triazine- Particularly preferred are 2-yl groups, 4,6-bis(3-pyridyl)-1,3,5-triazine-2-yl groups, 4-quinolyl groups, 5-quinolyl groups, 8-quinolyl groups, 6-quinoxalyl groups, 2-quinazolyl groups, 4-quinazolyl groups, 1,10-phenanthroline-5-yl groups, 2-dibenzothienyl groups, 4-dibenzothienyl groups, 2-dibenzofuranyl groups, or 4-dibenzofuranyl groups.

[0080] n represents an integer between 0 and 2. When n is 2, Ra may be the same or different. For ease of composition, n is preferably 1 or 2, and particularly preferably 1.

[0081] L ２ This represents a single bond, a linear, branched, or cyclic (n+1) valency aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n+1) valency aromatic hydrocarbon group having 6 to 18 carbon atoms, or a (n+1) valency heteroaromatic group having 3 to 20 carbon atoms. The aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings. L ２ From the viewpoint of device performance, the group is preferably a single bond, (n+1) valent benzene, (n+1) valent naphthalene, (n+1) valent pyridine, or (n+1) valent pyrimidine, with a single bond, (n+1) valent benzene, or (n+1) valent pyridine being particularly preferred, and a single bond, divalent benzene (1,4-phenylene group, 1,3-phenylene group, or 1,2-phenylene group) or divalent pyridine (3,4-pyridylene group, 2,5-pyridylene group, or 2,6-pyridylene group) being even more preferred. These groups may have substituents, and preferred substituents are methyl groups, cyano groups, fluoro groups, or trifluoromethyl groups.

[0082] R １１ ~R１６ each independently represent a hydrogen atom, a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, an iodo group, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon group and the heteroaromatic group may have one or more of a substituent and a linking group. From the viewpoint of synthesis and device performance, R １１ and R １２ are each independently preferably a hydrogen atom, a phenyl group, or a naphthyl group. Further, R １３ , R １４ and R １６ are hydrogen atoms, and R １５ is any one of a hydrogen atom, a cyano group, a trifluoromethyl group, a methoxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a phenyl group, or a pyridyl group, which is also preferable.

[0083] In R ｂ , L ２ , and R １１ to R １６ , examples of optional substituents include a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, a linear, branched or cyclic alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or combinations of these groups. The aromatic hydrocarbon group and the heteroaromatic group may be a single ring, a condensed ring, or a linked ring, and may also be a condensed ring or a linked ring formed of the aromatic hydrocarbon group and the heteroaromatic group.

[0084] In terms of easy synthesis, R ｂ , L ２ , and R １１ to R １６In this, the substituents that may be present are more preferably a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, an isopropyl group, a tert-butyl group, a phenoxy group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a (trifluoromethyl)phenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, or a (trifluoromethyl)pyridyl group, and particularly preferably a cyano group, a fluoro group, a trifluoromethyl group, a methyl group, a tert-butyl group, a phenoxy group, a phenyl group, a cyanophenyl group, a (trifluoromethyl)phenyl group, a pyridyl group, a cyanopyridyl group, or a (trifluoromethyl)pyridyl group.

[0085] <Embodiment> As an example of the stacked configuration of the organic electronic element (for example, a photoelectric conversion element) of the present invention, the following configuration (i) can be cited: (i): First electrode / hole transport promoting layer / hole transport layer / light receiving layer / electron transport layer / second electrode Note that if the organic electronic element is, for example, an organic EL element, then in the above configuration (i), the "light receiving layer" can be read as the "light emitting layer".

[0086] Hereinafter, the photoelectric conversion element and organic EL element according to the present invention will be described in more detail with reference to Figures 1 and 2, using the configuration described in (i) above as an example. Figure 1 is a schematic cross-sectional view showing an example of the stacked configuration of the photoelectric conversion element according to the present invention, and Figure 2 is a schematic cross-sectional view showing an example of an organic EL element.

[0087] <<First Embodiment>> The photoelectric conversion element according to the first embodiment is an organic image sensor or photosensor having the stacked structure shown in Figure 1. The photoelectric conversion element 1 comprises a first electrode 11 (first electrode), a hole transport promoting layer 12, a hole transport layer 13, a light receiving layer 14, an electron transport layer 15, and a second electrode 16 (second electrode) in this order. However, some of these layers may be omitted, or other layers may be added.

[0088] In the photoelectric conversion element 1 shown in Figure 1, light is incident from above the transparent first electrode 11 and received by the light-receiving layer 14. For convenience, Figure 1 shows the light incident from the side of the light-receiving layer 14. Furthermore, a voltage is applied to the photoelectric conversion element 1 so that the holes (positive and negative charges) generated by photoelectric conversion in the light-receiving layer 14 are moved to the first electrode 11 and the electrons are moved to the second electrode 16. That is, the first electrode 11 is used as a hole-collecting electrode and the second electrode 16 is used as an electron-collecting electrode. Note that in Figure 1, the substrate provided on the upper surface of the first electrode 11 is omitted. There are no particular limitations on the substrate here, and examples include glass plates, quartz plates, plastic plates, etc. Also, in the configuration where light is incident from the substrate side, the substrate is transparent with respect to the wavelength of light. The above layers will be described below.

[0089] [First Electrode 11] A first electrode 11 or a second electrode 16 is provided on the substrate. In the case of a photoelectric conversion element configured such that light passes through the first electrode 11 and is incident on the light-receiving layer 14, the first electrode is formed of a transparent material that transmits or substantially transmits the light. Here, "transmits light" means that the average transmittance is 80% or more, and "substantially transmits light" means that the average transmittance is 50% or more. In other words, in this specification, "transparent" means that the average transmittance is 50% or more.

[0090] The transparent material used for the first electrode 11 or the second electrode 16 is not particularly limited, but examples include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, aluminum-doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide.

[0091] In the case of a photoelectric conversion element configured such that light enters the light-receiving layer 14 only from the second electrode 16 side, the transmission characteristics of the first electrode 11 are not important. Therefore, examples of materials that can be used for the first electrode in this case include gold, iridium, molybdenum, palladium, platinum, etc.

[0092] [Hole Transport Promoting Layer 12] A hole transport promoting layer 12 is provided between the first electrode 11 and the hole transport layer 13, which will be described later. The hole transport promoting layer 12 is provided to promote hole transport from the hole transport layer 13 to the first electrode 11. The hole transport promoting layer 12 may contain the compound represented by formula (1) described above. It may also contain compounds other than the compound represented by formula (1). Examples of compounds that can be contained in the hole transport promoting layer 12 include conventionally known hole transport materials, and compounds used in the hole transport layer 13, which will be described later.

[0093] [Hole Transport Layer 13] A hole transport layer 13 is provided between the hole transport enhancement layer 12 and the light receiving layer 14. The hole transport layer 13 has the role of transporting holes generated in the light receiving layer 14 from the light receiving layer 14 to the first electrode 11, and blocking electrons generated in the light receiving layer 14 from moving toward the first electrode 11. Depending on the application, it may also have the role of blocking electron injection from the first electrode 11.

[0094] The hole transport layer 13 may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. The hole transport material that can be contained in the hole transport layer 13 may be a known hole transport material. Examples of known hole transport materials include aromatic tertiary amine compounds, naphthalene compounds, anthracene compounds, tetracene compounds, pentacene compounds, phenanthrene compounds, pyrene compounds, perylene compounds, fluorene compounds, carbazole compounds, indole compounds, pyrrole compounds, picene compounds, thiophene compounds, benzotrifuran compounds, benzotrithiophene compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodithiophene compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, crisenodithiophene compounds, benzothienobenzothiophene compounds, indolocarbazole compounds, and the like. Among these, fluorene compounds, carbazole compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, crisenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds are preferred, with fluorene compounds, carbazole compounds, crisenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds being particularly preferred.

[0095] [Light-receiving layer 14] A light-receiving layer 14 is provided between the hole transport layer 13 and the electron transport layer 15, which will be described later. The material for the light-receiving layer 14 is a material that has a photoelectric conversion function.

[0096] The light-receiving layer 14 may be a single-layer structure made of one or more materials, or a laminated structure made of multiple layers with the same or different compositions. In particular, in order to increase the photoelectric conversion efficiency, it is preferable that the light-receiving layer consists of layers containing at least two materials (organic components).

[0097] Examples of materials used in the light-receiving layer 14, which is a single-layer structure made of one type of material, include (i) coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, etc. Examples of materials used in the light-receiving layer 14, which is a single-layer structure made of two types of materials, include the aforementioned (i) coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, and (ii) fullerene and its derivatives, and other acceptor materials. The light-receiving layer 4 made of these materials may be formed by pre-mixing the powders and then depositing them, or by co-depositing them in any proportion. Examples of materials used in the light-receiving layer 14, which is a single-layer structure made of three types of materials, include the aforementioned (i) coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, (ii) fullerene and its derivatives, other acceptor materials, and (iii) hole transport materials. The light-receiving layer 14, made of these materials, may be formed by pre-mixing the powders and then depositing them, or by co-depositing them in any proportion.

[0098] (i) Specific examples of coumarin derivatives include coumarin 6 and coumarin 30. Specific examples of quinacridone derivatives include N,N-dimethylquinacridone. Specific examples of phthalocyanine derivatives include boron subphthalocyanine chloride and boron subnaphthalocyanine chloride (SubNC). (ii) Specific examples of fullerenes and their derivatives include

[60] fullerene,

[70] fullerene, and [6,6]-phenyl-C61-methyl butyrate (

[60] PCBM). (iii) Preferred compounds and specific examples of hole transport materials are the same as those used in the hole transport layer 13 described above.

[0099] Furthermore, the material having photoelectric conversion functionality is not limited to being contained only in the light-receiving layer. For example, the material having photoelectric conversion functionality may also be contained in a layer adjacent to the light-receiving layer 14 (the hole transport layer 13 or the electron transport layer 15).

[0100] [Electron Transport Layer 15] An electron transport layer 15 is provided between the light-receiving layer 14 and the second electrode 16, which will be described later. The electron transport layer 15 has the role of transporting electrons generated in the light-receiving layer 14 to the second electrode 16 and blocking the movement of holes from the second electrode 16 to the light-receiving layer 14. Depending on the application, it may also have the role of blocking hole injection from the second electrode 16. The electron transport layer 15 may be divided into two or more layers using different materials.

[0101] The electron transport layer 15 contains the compound shown in formula (1) above. The electron transport layer 15 may also contain electron transport materials or metals other than the compound shown in formula (1). Examples of electron transport materials that can be included in the electron transport layer 15 include fullerene, fullerene derivatives, triazine derivatives, bis(8-hydroxyquinolinate)manganese, tris(8-hydroxyquinolinate)aluminum, tris(2-methyl-8-hydroxyquinolinate)aluminum, BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-diphenyl-1,10-phenanthroline), and BAlq(bis(2-methyl-8-quinolinate)-4-(phenyl Examples include phenolate (aluminum), 4,6-bis(3,5-di(pyridine-4-yl)phenyl)-2-methylpyrimidine, N,N'-diphenyl-1,4,5,8-naphthalenetetracarboxylic acid diimide, and N,N'-di(4-pyridyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide, fullerene, fullerene derivatives, Liq(8-hydroxyquinolinolatolithium), Li, Na, K, Rb, Cs, Be, Mg, Ca, Sc, Ba, Ag, Eu, Yb, lithium fluoride, cesium carbonate, etc.

[0102] The electron transport layer 15 may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions.

[0103] [Second Electrode 16] A second electrode 16 is provided on the electron transport layer 15. The material of the second electrode 16 may be, for example, indium-tin oxide (ITO), indium-zinc oxide (IZO), sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ２ O ３ Examples include mixtures, indium, lithium / aluminum mixtures, gold, platinum, rare earth metals, molybdenum oxide, etc. The first electrode 11 and the second electrode 16 may be the same or different.

[0104] [Method for forming each layer] Each layer, excluding the first electrode 11 and the second electrode 16 described above, can be formed by thinning the material of each layer (along with binder resin and other materials and solvents as needed) using known methods such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett method. There are no particular restrictions on the thickness of each layer formed in this way, and it can be appropriately selected depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0105] The first electrode 11 and the second electrode 16 can be formed by thinning the electrode material using methods such as vapor deposition or sputtering. A pattern may be formed via a mask of a desired shape during vapor deposition or sputtering, or a pattern of a desired shape may be formed by photolithography after the thin film has been formed by vapor deposition or sputtering.

[0106] The film thickness of the first electrode 11 and the second electrode 16 is preferably 1 μm or less, and more preferably 10 nm to 200 nm.

[0107] The first electrode 11 and the second electrode 16 may be made of different materials as needed (this is also called an inverse structure). In such a structure, the photoelectric conversion element is configured such that light passes through the second electrode 16 and enters the light-receiving layer 14.

[0108] The image sensor equipped with the photoelectric conversion element of this embodiment can be applied, for example, to image sensors in digital cameras and digital video cameras, and to image sensors built into mobile phones, etc. The light sensor can be applied, for example, to television remote controls, air conditioner switches, automatic door opening and closing, etc.

[0109] <<Second Embodiment>> The photoelectric conversion element according to the second embodiment of the present invention is a solar cell having the stacked structure shown in Figure 1. The solar cell 1 has a hole transport promoting layer 12 and a hole transport layer 13 between the first electrode 11 and the light receiving layer 14, and an electron transport layer 15 between the second electrode 16 and the light receiving layer 14. However, some of these layers may be omitted, or other layers may be added.

[0110] [First Electrode 11] The first electrode 11 is made of, for example, a transparent material, and the transparent material can be the transparent material in the first embodiment. The first electrode 11 may be formed on any substrate (for example, a transparent substrate such as glass, plastic, or polymer film).

[0111] [Hole Transport Promoting Layer 12] The material of the hole transport promoting layer 12 is the same as the material of the hole transport promoting layer 12 in the first embodiment (a compound represented by formula (1)). The material of the hole transport promoting layer 12 may also contain conventionally known hole transport materials in addition to the material in the first embodiment.

[0112] [Hole Transport Layer 13] The material of the hole transport layer 13 is the same as the material of the hole transport layer 13 in the first embodiment. In addition to the hole transport material in the first embodiment, the material of the hole transport layer 13 may also contain conventionally known hole transport materials.

[0113] [Light-receiving layer 14] The material of the light-receiving layer 14 may be any material using an electron-donating material and an electron-accepting material, and may be a planar-bonded type in which the electron-donating material and the electron-accepting material are bonded to each other in a planar manner, or a bulk hetero-bonded type in which the electron-donating material and the electron-accepting material are mixed and formed into a film. The electron-donating material is not particularly limited, but an organic semiconductor is preferred. Examples of electron-donating materials include polymer compounds such as polythiophene derivatives, polyfluorene derivatives, and polyphenylene vinylene derivatives and copolymers thereof, or low molecular weight compounds such as phthalocyanine derivatives and their metal complexes, porphyrin derivatives and their metal complexes, acene derivatives such as pentacene, and diamine derivatives. The electron-donating material may also be an inorganic semiconductor in addition to an organic semiconductor, as long as it does not impair the effects of the present invention. The electron-accepting material is not particularly limited, but an organic semiconductor is preferred. Examples of electron-accepting materials include fullerene derivatives, perylene derivatives, and naphthalene derivatives.

[0114] [Electron Transport Layer 15] The material for the electron transport layer 15 can be the electron transport material from the first embodiment. Alternatively, alkali metal halides such as sodium fluoride and cesium fluoride, alkaline earth metal halogen compounds such as calcium fluoride, carbonates such as cesium carbonate, and inorganic n-type semiconductors such as titanium dioxide and zinc oxide may be used as the electron transport material.

[0115] [Second Electrode 16] The second electrode 16 may be, but is not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof.

[0116] The first electrode 11 and the second electrode 16 may be made of different materials as needed (this is also called an inverse structure). In such a structure, the photoelectric conversion element is configured such that light passes through the second electrode 16 and enters the light-receiving layer 14.

[0117] [Method for forming each layer] The method for forming each layer is not particularly limited. For example, the first electrode 11, hole transport enhancement layer 12, hole transport layer 13, light receiving layer 14, electron transport layer 15, and second electrode 16 may be sequentially laminated on a substrate using a vapor deposition method, spin coating method, casting method, pattern transfer method, etc. Alternatively, after laminating the hole transport enhancement layer 12, hole transport layer 13, light receiving layer 14, and electron transport layer 15, the first electrode 11 and second electrode 16 may be formed on this laminate by transfer, vapor deposition, sputtering, etc., respectively.

[0118] <<Third Embodiment>> The organic electronic element according to the third embodiment of the present invention is an organic EL element having the stacked structure shown in Figure 2. That is, the organic EL element 2 is provided with a first electrode 21, a hole injection layer 22, a hole transport layer 23, a light-emitting layer 24, an electron transport layer 25, and a second electrode 26 in this order. However, some of these layers may be omitted, or other layers may be added.

[0119] [First Electrode 21] The first electrode 21 has the role of injecting holes from the hole transport layer to the light-emitting layer. The first electrode 21 can be, but is not limited to, transparent electrodes such as indium tin oxide (ITO), indium zinc oxide (IZO), gold, silver, platinum, and copper, metals and alloys such as aluminum, molybdenum, chromium, and nickel, polythiophene derivatives and polyaniline derivatives that have high charge transport properties.

[0120] The organic electronic device may emit light from either side of the first electrode 21 and the second electrode 26, or from both sides. The electrode that extracts light is formed from a transparent material such as ITO or IZO. For convenience, Figure 2 shows the light being emitted from the side of the light-emitting layer 24.

[0121] [Hole Injection Layer 22] A hole injection layer 22 is provided between the first electrode 21 and the hole transport layer 23, which will be described later. The hole injection layer 22 is provided to promote hole transport from the first electrode 21 to the hole transport layer 23. The hole injection layer 22 contains the compound represented by formula (1) above as a hole injection material. The hole injection layer 22 may also contain compounds other than the compound represented by formula (1) above. Examples of compounds that can be contained in the hole injection layer 22 include conventionally known hole transport materials.

[0122] [Hole Transport Layer 23] A hole transport layer 23 is provided between the hole injection layer 22 and the light-emitting layer 24. The hole transport layer 23 has the role of transporting holes injected from the first electrode 21 to the light-emitting layer 24. The hole transport layer 23 may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. The hole transport material that can be contained in the hole transport layer 23 may be the same as the material of the hole transport layer 13 in the first embodiment.

[0123] [Emitting layer 24] The emissive layer 24 plays a role in generating light (phosphorescence or fluorescence) by the recombination of holes injected from the first electrode 21 and electrons injected from the second electrode 26, and includes an emissive material and, if necessary, an emissive host material. The emissive material and the emissive host material can be appropriately selected from known materials. Examples of luminescent materials and luminescent host materials include carbon condensed ring dyes such as triazine derivatives (including TADF materials substituted with carbazole, etc.), pyrimidine derivatives, carbazole derivatives, anthracene derivatives, tetracene derivatives, pyrene derivatives, rubrene derivatives, and decacycline derivatives; perylene derivatives such as perylenediimide, xanthene dyes such as rhodamine B, cyanine dyes, coumarin dyes such as coumarin 6 and C545T, quinacridone dyes such as Qd4 and DEQ, squarium dyes, styryl dyes, pyrazolone derivatives, phenoxazone dyes such as NileRed, carbazole, triarylamine, and tris(2-phenylpyridine). Examples of iridium complexes include, but are not limited to, iridium(III) (Ir(ppy)3), tris[2-phenyl-4-(2-ethylcyclohexyloxy)pyridine]iridium(III) (Ir(ehppy)3), aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrin zinc complexes, europium complexes, metal complexes composed of a central metal made of Al, Zn, Be or rare earth metals such as Tb, Eu, Dy, and ligands such as oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, and quinoline structures.

[0124] [Electron Transport Layer 25] The electron transport layer 25 is provided between the second electrode and the light-emitting layer and has the function of transporting electrons injected from the second electrode to the light-emitting layer, and includes an electron transport material. The electron transport material can be the electron transport material of the first embodiment. Examples of electron transport materials include, but are not limited to, triazine derivatives, tris(8-quinolinolate)aluminum (Alq3), bis(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum (BAlq), 1,4,4'-bis(2,2'-diphenylvinyl)-1,1'-bipheny (DPVBi), (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole) (PBD), triazole derivatives (TAZ), basocuproine (BCP), silole derivatives, etc.

[0125] [Second Electrode 26] The second electrode 26 has the role of injecting electrons from the electron transport layer 25 to the light-emitting layer 24. The second electrode 26 can be made of aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium, cesium-doped ITO, etc., but is not limited to these.

[0126] [Method for Forming Each Layer] The method for forming each layer of the organic EL element 2 is as follows: First, a thin film made of the material for the first electrode 21 is formed on a suitable translucent substrate (not shown) by methods such as vapor deposition and sputtering. A hole injection layer 22 and a hole transport layer 23 are then deposited on the first electrode 21 in this order. The hole injection layer 22 and the hole transport layer 23 can be deposited by methods such as vacuum deposition, spin coating, casting, and LB. Next, an emissive layer 24 is provided on the hole transport layer 23. The emissive layer 24 can also be formed by thinning an organic emissive material using a desired organic emissive material by methods such as vacuum deposition, sputtering, spin coating, and casting. Next, an electron transport layer 25 is formed on the emissive layer 24. The electron transport layer 25 can be formed by the same method as the hole transport layer and the emissive layer. Finally, a second electrode 26 is laminated on the electron transport layer 25. The second electrode 26 can be formed from a desired metal material by methods such as vapor deposition and sputtering. The method for forming each layer of an organic EL element is not limited to the method described above. For example, known methods such as vacuum deposition, molecular beam deposition (MBE), dipping using a solution of the material dissolved in a solvent, spin coating, casting, bar coating, roll coating, and other coating methods can be appropriately employed.

[0127] The organic electronic elements (photoelectric conversion elements, organic EL elements, etc.) and the methods for forming each layer of the elements are not limited to the elements and methods shown in the embodiments described above. For example, the materials of the first electrode, the light-receiving layer (or light-emitting layer), the electron transport layer, and the second electrode can be appropriately replaced with other known materials. Furthermore, the hole injection layer and the hole transport layer can be replaced with layers formed by mixing a compound represented by formula (1) with a hole transport material.

[0128] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. The obtained compounds are １ Identification was made based on the H-NMR spectrum (400 MHz). １ For the measurement of the H-NMR spectrum, a Bruker ASCEND 400 (400 MHz; manufactured by BR UKER) was used. １The H-NMR spectrum is deuterated chloroform (CDCl). ３ ) or didimethyl sulfoxide (DMSO-d ６ The measurement was performed using ) as the solvent and tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0129]

[0130] (Synthesis Reference Example 1: Synthesis of Compound (13)) Under a nitrogen stream, 23.5 g (175.0 mmol) of 3,4-dimethylbenzaldehyde, 21.6 g (175.0 mmol) of p-anisidine, and 230 mL of ethanol were added to a 1000 mL three-necked flask and stirred at 80°C for 5 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. 200 mL of hexane was added to the precipitated solid to disperse it, and the mixture was then filtered to obtain the target compound (13) (29.8 g, yield 71%). １ H-NMR (CDCl ３ ) δ (ppm): 8.42 (d, 1H), 7.71 (d, 1H), 7.57 (dd, 1H), 7.24-7.20 (m, 3H), 6.93 (d, 2H), 3.83 (s, 3H), 2.33 (s, 3H), 2.32 (s, 3H).

[0131] (Synthesis Reference Example 2: Synthesis of Compound (14)) Under a nitrogen stream, 20.0 g (83.6 mmol) of Compound (13) obtained in Synthesis Reference Example 1, 26.3 g (167.2 mmol) of bromobenzene, 1.5 g (2.5 mmol) of dichloro(p-cymene)ruthenium(II) dimer, 2.6 g (10.1 mmol) of triphenylphosphine, 23.1 g (167.2 mmol) of potassium carbonate, and 200 mL of N-methylpyrrolidone were added to a 1000 mL three-necked flask and stirred at 135°C for 15 hours. After cooling to room temperature, 100 mL of tetrahydrofuran and 300 mL of 10% hydrochloric acid aqueous solution were added and stirred at room temperature. After extracting the organic layer with 300 mL of toluene, the aqueous layer and the organic layer were separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (using a mixed solvent of toluene and hexane (volume ratio = 3:7)) to obtain the target compound (14) (15.5 g, yield 88%). １ H-NMR (CDCl ３ ) δ (ppm): 9.93 (s, 1H), 7.81 (s, 1H), 7.47-7.42 (m, 3H), 7.37-7.34 (m, 2H), 7.22 (s, 1H), 2.37 (s, 3H), 2.36 (s, 3H).

[0132] (Synthesis Reference Example 3: Synthesis of Compound (15)) Under a nitrogen stream, 15.5 g (73.7 mmol) of Compound (14) obtained in Synthesis Reference Example 2, 23.3 g (147.4 mmol) of potassium permanganate, 250 mL of tert-butyl alcohol, and 250 mL of water were added to a 1000 mL three-necked flask and stirred at 80°C for 1 hour. Then, 46.6 g (294.8 mmol) of potassium permanganate was added in two portions at 1-hour intervals and stirred at 80°C for 12 hours. After the reaction was complete, 20 mL of ethanol was added and it was confirmed that the reddish-purple color of the reaction solution had disappeared. After cooling to room temperature, the solution was filtered by Celite, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 300 mL of water. Next, concentrated hydrochloric acid was added under ice cooling until the pH reached 2-3, and the mixture was stirred at room temperature for 2 hours. The precipitated solid was then collected by filtration to obtain the target compound (15) (14.5 g, yield 69%). １H-NMR (DMSO-d ６ ) δ (ppm): 13.28 (br-s, 3H), 8.02 (s, 1H), 7.60 (s, 1H), 7.47-7.37 (m, 5H).

[0133] (Synthesis Reference Example 4: Synthesis of Compound (16)) The procedure was the same as in Synthesis Reference Example 2 and Synthesis Reference Example 3, except that 47.3 g (167.2 mmol) of p-bromoiodobenzene was used instead of 26.3 g (167.2 mmol) of bromobenzene, to obtain the target compound (16) (17.8 g, yield 66%). １ H-NMR (DMSO-d ６ ) δ (ppm): 13.33 (br-s, 3H), 8.17 (s, 1H), 7.71 (s, 1H), 7.64 (d, 2H), 7.34 (d, 2H).

[0134] (Synthesis Reference Example 5: Synthesis of Compound (17)) Under a nitrogen atmosphere, 12.0 g (41.9 mmol) of compound (15) obtained in Synthesis Reference Example 3 and 200 mL of polyphosphate were added to a 1000 mL three-necked flask and stirred at 130 °C for 10 hours. After cooling to room temperature, 400 mL of water was added, and the precipitated solid was collected by filtration and washed with water and methanol. Next, the obtained solid was heated and washed with acetic anhydride to obtain the target compound (B1) (8.6 g, yield 82%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.61 (s, 1H), 8.18 (dd, 1H), 8.12 (s, 1H), 7.80-7.76 (m, 2H), 7.57 (ddd, 1H).

[0135] (Synthesis Reference Example 6: Synthesis of Compound (18)) The same procedure as in Synthesis Example 1 was followed, except that 15.3 g (41.9 mmol) of compound (16) obtained in Synthesis Reference Example 4 was used instead of 12.0 g (41.9 mmol) of compound (15) obtained in Synthesis Reference Example 3, to obtain the target compound (18) (11.0 g, yield 80%). １ H-NMR (DMSO-d ６) δ (ppm): 8.65 (s, 1H), 8.16 (s, 1H), 8.14 (d, 1H), 8.01 (dd, 1H), 7.93 (d, 1H).

[0136] (Synthesis Reference Example 7: Synthesis of Compound (19)) Under a nitrogen atmosphere, 5.00 g (28.1 mmol) of ninhydrin, 6.49 g (30.9 mmol) of 1,3-diphenyl-2-propanone, and 74 mL of ethanol were added to a 200 mL three-necked flask. 11 mL of 0.5 M potassium hydroxide / ethanol solution was added dropwise, and the mixture was stirred at 80°C for 3 hours. After cooling to room temperature, the solid was filtered. The obtained solid was stirred in 50 mL of dimethylformamide and 50 mL of toluene at 110°C, then cooled to room temperature, and filtered to obtain the target compound (19) (5.67 g, yield 60%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.44 (dd, 2H), 8.17 (d, 1H), 8.05 (d, 1H), 7.95 (td, 1H), 7.91 (dt, 1H), 7.72 (d, 2H), 7.61-7.56 (m, 5H), 7.50 (t, 1H).

[0137] (Synthesis Reference Example 8: Synthesis of Compound (20)) Under a nitrogen atmosphere, 0.500 g (1.50 mmol) of compound (17) obtained in Synthesis Reference Example 5, 1.02 g (8.97 mmol) of acetylenedicarboxylic acid, and 5 mL of xylene were added to a 50 mL three-necked flask and stirred at 140°C for 18 hours. After cooling to room temperature, the precipitated solid was filtered and washed with hexane. Next, the obtained solid was stirred in 10 mL of xylene at 140°C, cooled to room temperature, and then filtered to obtain the target compound (20) (0.40 g, yield 66%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.65-7.64 (m, 3H), 7.60 (dd, 1H), 7.53-7.37 (m, 9H), 6.32 (d, 1H).

[0138] (Synthesis Reference Example 9: Synthesis of Compound (21)) Under a nitrogen atmosphere, 1.25 g (7.03 mmol) of ninhydrin, 1.73 g (7.03 mmol) of 1,3-bis(4-fluorophenyl)-2-propanone, and 12 mL of ethanol were added to a 50 mL two-necked flask. 1.4 mL of 0.5 M potassium hydroxide / ethanol solution was added dropwise, and the mixture was stirred at 80°C for 1 hour. After cooling to room temperature, the mixture was filtered to obtain the target compound (21) (1.85 g, yield 71%). １ H-NMR (CDCl ３ ) δ (ppm): 8.73 (dd, 2H), 8.16 (dd, 1H), 8.09 (dd, 1H), 7.78-7.75 (m, 2H), 7.70 (dd, 2H), 7.26-7.18 (m, 4H). １９ F-NMR (CDCl ３ ) δ (ppm): -106.17, -111.34.

[0139] (Synthesis Reference Example 10: Synthesis of Compound (22)) Under a nitrogen atmosphere, 1.82 g (5.00 mmol) of compound (21) obtained in Synthesis Reference Example 9, 6.19 g (35.0 mmol) of 3-bromofuran-2,5-dione, and 25 mL of xylene were added to a 100 mL three-necked flask and stirred at 140°C for 14 hours. After cooling to room temperature, the precipitated solid was filtered and washed with hexane. Next, the obtained solid was stirred in 15 mL of xylene at 140°C, cooled to room temperature, and then filtered to obtain the target compound (22) (1.06 g, yield 49%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.62-7.55 (m, 5H), 7.50-7.42 (m, 4H), 7.31 (t, 2H), 6.41 (dd, 1H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -113.02, -113.03.

[0140] (Synthesis Reference Example 11: Synthesis of Compound (23)) Under a nitrogen atmosphere, 1.72 g (9.64 mmol) of ninhydrin, 2.72 g (9.64 mmol) of 1,3-bis(3,5-difluorophenyl)-2-propanone, and 64 mL of ethanol were added to a 200 mL two-necked flask. 1.9 mL of 0.5 M potassium hydroxide / ethanol solution was added dropwise, and the mixture was stirred at 80°C for 2 hours. After cooling to room temperature, the mixture was filtered to obtain the target compound (23) (3.23 g, yield 82%). １ H-NMR (CDCl ３ ) δ (ppm): 8.32 (dd, 2H), 8.22 (dd, 1H), 8.13 (dd, 1H), 7.86-7.84 (m, 2H), 7.27-7.45 (m, 2H), 6.98-6.91 (m, 2H). １９ F-NMR (CDCl ３ ) δ (ppm): -108.60.

[0141] (Synthesis Reference Example 12: Synthesis of Compound (24)) Under a nitrogen atmosphere, 1.00 g (2.46 mmol) of compound (23) obtained in Synthesis Reference Example 11, 2.53 g (22.2 mmol) of acetylenedicarboxylic acid, and 12 mL of xylene were added to a 100 mL three-necked flask and stirred at 140 °C for 16 hours. After cooling to room temperature, the precipitated solid was filtered and washed with hexane. The obtained solid was stirred in 10 mL of ethanol and filtered to obtain the target compound (24) (0.53 g, yield 45%). １ H-NMR (CDCl ３ ) δ (ppm): 7.69 (d, 1H), 7.43 (td, 1H), 7.37 (td, 1H), 7.12 (tt, 1H), 7.02-6.90 (m, 5H), 6.58 (d, 1H). １９ F-NMR (CDCl ３ ) δ (ppm): -106.49, -109.19.

[0142] (Synthesis Reference Example 13: Synthesis of Compound (25)) Under a nitrogen atmosphere, 2.76 g (15.5 mmol) of ninhydrin, 4.38 g (14.1 mmol) of 1,3-di(2-naphthyl)-2-propanone, and 47 mL of ethanol were added to a 200 mL two-necked flask. 28.2 mL of 0.5 M potassium hydroxide / ethanol solution was added dropwise, and the mixture was stirred at 80°C for 3 hours. After cooling to room temperature, the mixture was filtered to obtain the target compound (25) (4.10 g, yield 67%). １ H-NMR (CDCl ３ ) δ (ppm): 9.23 (s, 1H), 8.84 (dd, 1H), 8.28-8.27 (m, 2H), 8.14 (d, 1H), 8.03 (d, 2 H), 7.98-7.92 (m, 3H), 7.88-7.85 (m, 2H), 7.81-7.74 (m, 2H), 7.60-7.52 (m, 4H).

[0143] (Synthesis Reference Example 14: Synthesis of Compound (26)) Under a nitrogen atmosphere, 0.50 g (1.15 mmol) of compound (25) obtained in Synthesis Reference Example 13, 2.04 g (11.5 mmol) of 3-bromofuran-2,5-dione, and 5.7 mL of xylene were added to a 50 mL three-necked flask and stirred at 140°C for 24 hours. After cooling to room temperature, the precipitated solid was filtered and washed with hexane. The obtained solid was stirred in 10 mL of xylene at 140°C, cooled to room temperature, and then filtered to obtain the target compound (26) (0.33 g, yield 57%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.20 (d, 1H), 8.13-8.10 (m, 3H), 8.03 (t, 3H), 7.97 (d, 1H), 7.69-7.59 (m, 7H), 7.39 (t, 1H), 7.32 (t, 1H), 6.34 (d, 1H).

[0144] (Synthesis Example 1: Synthesis of Compound (A2)) Under a nitrogen atmosphere, 0.500 g (1.2 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.16 g (1.4 mmol) of 4-aminobenzonitrile, 0.070 g (0.62 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 10 mL of xylene were added to a 100 mL three-necked flask and stirred at 140 °C for 11 hours. After cooling to room temperature, the solid was collected by filtration and washed with ethanol. Next, the obtained solid was recrystallized with dimethylformamide to obtain the target compound (A2) (0.65 g, yield 82%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.94 (s, 2H), 7.61-7.34 (m, 15H), 6.25 (d, 1H).

[0145] (Synthesis Example 2: Synthesis of Compound (A3)) Under a nitrogen atmosphere, 0.402 g (1.0 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.12 g (1.1 mmol) of 3-aminobenzonitrile, 0.084 g (0.75 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the target compound (A3) was obtained by filtration of the solid (0.46 g, yield 92%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.85 (dt, 1H), 7.82 (t, 1H), 7.72-7.64 (m, 2H), 7.62-7.59 (m, 3H), 7.57 (dd, 1H), 7.53-7.33 (m, 9H), 6.25 (dd, 1H).

[0146] (Synthesis Example 3: Synthesis of Compound (A7)) Under a nitrogen atmosphere, 0.300 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.13 g (0.89 mmol) of 4-aminophthalonitrile, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 7 hours. After cooling to room temperature, the target compound (A7) was obtained by filtration of the solid (0.24 g, yield 60%). １H-NMR (DMSO-d ６ ) δ (ppm): 8.23 ​​(d, 1H), 8.12 (d, 1H), 7.92 (dd, 1H), 7.63-7.60 (m, 3H), 7.57 (d, 1H), 7.52-7.34 (m, 9H), 6.26 (d, 1H).

[0147] (Synthesis Example 4: Synthesis of Compound (A12)) Under a nitrogen atmosphere, 0.300 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.12 g (0.89 mmol) of 3,5-difluoroaniline, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the target compound (A12) was obtained by filtration of the solid (0.37 g, yield 98%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.62-7.60 (m, 3H), 7.57 (dd, 1H), 7.52-7.29 (m, 9H), 7.14 (dd, 2H), 7.04 (s, 1H), 6.24 (d, 1H). １９ F-NMR (CDCl ３ ) δ (ppm): -109.54.

[0148] (Synthesis Example 5: Synthesis of Compound (A13)) Under a nitrogen atmosphere, 0.500 g (1.2 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.15 g (1.3 mmol) of 4-fluoroaniline, 0.10 g (0.93 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 12 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 5 hours. After cooling to room temperature, the target compound (A13) was obtained by filtration of the solid (0.55 g, yield 89%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.61-7.58 (m, 3H), 7.56 (d, 1H), 7.52-7.32 (m, 11H), 7.30-7.25 (m, 2H), 6.23 (d, 1H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -113.46.

[0149] (Synthesis Example 6: Synthesis of Compound (A16)) Under a nitrogen atmosphere, 1.01 g (2.5 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.51 g (2.6 mmol) of 2'-amino-[1,1'-biphenyl]-4-carbonilolyl, 0.21 g (1.9 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 13 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 12 hours. After cooling to room temperature, the target compound (A16) was obtained by filtration of the solid (0.76 g, yield 53%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.86 (dd, 2H), 7.59-7.27 (m, 19H), 6.21 (d, 1H).

[0150] (Synthesis Example 7: Synthesis of Compound (A19)) Under a nitrogen atmosphere, 1.45 g (3.6 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.83 g (3.8 mmol) of 2'-amino-[1,1'-biphenyl]-3,5-dicarbonilolyl, 0.30 g (2.7 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 18 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 12 hours. After cooling to room temperature, the target compound (A19) was obtained by filtration of the solid (1.51 g, yield 70%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.50 (t, 1H), 7.92 (d, 2H), 7.60-7.13 (m, 17H), 6.23 (d, 1H).

[0151] (Synthesis Example 8: Synthesis of Compound (A20)) Under a nitrogen atmosphere, 0.500 g (1.2 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.27 g (1.2 mmol) of 6-amino-[1,1'-biphenyl]-3,4'-dicarbonilolyl, 0.070 g (0.62 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 10 mL of xylene were added to a 100 mL three-necked flask and stirred at 140 °C for 7 hours. After cooling to room temperature, the solid was filtered off and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized in hexane / toluene to obtain the target compound (A20) (0.17 g, yield 23%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.08 (d, 1H), 8.05 (d, 1H), 7.91 (d, 2H), 7.73 (d, 1H), 7.60-7.53 (m, 4H), 7.48-7.12 (d, 11H) 6.23 (d, 1H).

[0152] (Synthesis Example 9: Synthesis of Compound (A21)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.13 g (0.89 mmol) of 1-aminonaphthalene, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the target compound (A21) was obtained by filtration of the solid (0.37 g, yield 94%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.01 (t, 2H), 7.82 (d, 1H), 7.63-7.50 (m, 12H), 7.45-7.34 (m, 5H), 6.26 (dd, 1H).

[0153] (Synthesis Example 10: Synthesis of Compound (A28)) Under a nitrogen atmosphere, 1.2 g (2.9 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.65 g (3.0 mmol) of 3-aminofluoranthene, 0.24 g (2.1 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 29 mL of xylene were added to a 100 mL two-necked flask and stirred at 140 °C for 5 hours. After cooling to room temperature, the target compound (A28) was obtained by filtration of the solid (1.6 g, yield 92%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.17 (d, 1H), 8.13 (d, 1H), 8.05-8.03 (m, 2H), 7.83 (d, 1H), 7.69-7.36 (m, 17H), 6.27 (d, 1H).

[0154] (Synthesis Example 11: Synthesis of Compound (A31)) Under a nitrogen atmosphere, 1.01 g (2.5 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.64 g (2.6 mmol) of 5'-amino-m-terphenyl, 0.28 g (2.5 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 13 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 4 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure and recrystallized in a mixed solvent of xylene and ethanol to obtain the target compound (A31) (1.5 g, yield 95%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.90-7.88 (m, 1H), 7.74-7.69 (m, 4H), 7.61-7.32 (m, 21H), 6.22 (d, 1H).

[0155] (Synthesis Example 12: Synthesis of Compound (A32)) Under a nitrogen atmosphere, 0.90 g (2.2 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.79 g (2.6 mmol) of 3,5-bis(4-cyanophenyl)aniline, 0.19 g (1.6 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 22 mL of xylene were added to a 100 mL two-necked flask and stirred at 140 °C for 4 hours. After cooling to room temperature, the target compound (A32) was obtained by filtration of the solid (1.52 g, yield 100%). １ H-NMR (DMSO-d６ ) δ (ppm) 8.11 (s, 1H), 8.00-7.93 (m, 8H), 7.80 (d, 2H), 7.62-7.33 (m, 13H), 6.24 (d, 1H).

[0156] (Synthesis Example 13: Synthesis of Compound (A57)) Under a nitrogen atmosphere, 1.00 g (2.5 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.38 g (2.6 mmol) of 4-aminoquinoline, 0.21 g (1.9 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 25 mL of xylene were added to a 50 mL two-necked flask and stirred at 140°C for 5 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was stirred in 15 mL of xylene at 140°C, cooled to room temperature, and the solid was collected by filtration to obtain the target compound (A57) (1.05 g, yield 80%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.00 (d, 1H), 8.09 (d, 1H), 7.98 (dd, 1H), 7.81 (t, 1H), 7.63 (d, 1H), 7.60-7.52 (m, 9H), 7.45-7.34 (m, 5H), 6.27 (dd, 1H).

[0157] (Synthesis Example 14: Synthesis of Compound (A65)) Under a nitrogen atmosphere, 1.01 g (2.5 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.65 g (2.6 mmol) of 2,6-diphenylpyridine-4-amine, 0.21 g (1.9 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 13 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 9 hours. After cooling to room temperature, the target compound (A65) was obtained by filtration of the solid (1.53 g, yield 97%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.13-8.11 (m, 4H), 7.92 (s, 2H), 7.64-7.37 (m, 19H), 6.25 (d, 1H).

[0158] (Synthesis Example 15: Synthesis of Compound (A77)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.15 g (0.89 mmol) of 2-amino-4-(trifluoromethyl)thiazole, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 7 hours. After cooling to room temperature, the target compound (A77) was obtained by filtration of the solid (0.34 g, yield 82%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.39 (s, 1H), 7.64-7.63 (m, 3H), 7.57 (d, 1H), 7.53-7.47 (m, 6H), 7.42-7.36 (m, 2H), 7.04 (s, 1H), 6.26 (d, 1H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -62.76.

[0159] (Synthesis Example 16: Synthesis of Compound (A79)) Under a nitrogen atmosphere, 0.50 g (1.2 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.16 g (1.3 mmol) of 2-aminothiazole-5-carbonitride, 0.10 g (0.093 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 13 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 5 hours. After cooling to room temperature, the target compound (A79) was obtained by filtration of the solid (0.52 g, yield 81%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.54 (s, 1H), 7.64 (dd, 3H), 7.57 (d, 1H), 7.52-7.26 (m, 9H), 6.26 (d, 1H).

[0160] (Synthesis Example 17: Synthesis of Compound (A91)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.053 g (0.89 mmol) of 1-aminopropane, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the target compound (A91) was obtained by filtration of the solid (0.27 g, yield 81%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.60-7.58 (m, 3H), 7.53 (dd, 1H), 7.49-7.42 (m, 7H), 7.38-7.30 (m, 2H), 6.20 (d, 1H), 3.35 (t, 2H), 1.47 (q, 2H), 0.77 (t, 3H).

[0161] (Synthesis Example 18: Synthesis of Compound (A92)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.078 g (0.89 mmol) of 3-aminopentane, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the target compound (A92) was obtained by filtration of the solid (0.35 g, yield 100%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.51-7.25 (m, 13H), 6.00 (d, 1H), 3.35 (m, 1H), 1.14-1.03 (m, 4H), 0.57 (t, 6H).

[0162] (Synthesis Example 19: Synthesis of Compound (A94)) Under a nitrogen atmosphere, 1.01 g (2.5 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.26 g (2.6 mmol) of cyclohexylamine, 0.21 g (1.9 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 13 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 9 hours. After cooling to room temperature, hexane was added and stirred, and the precipitated solid was collected by filtration. The obtained solid was recrystallized in a mixed solvent of toluene and hexane to obtain the target compound (A94) (0.65 g, yield 54%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.60-7.57 (m, 3H), 7.52 (dd, 1H), 7.50-7.29 (m, 9H), 6.19 (d, 1H), 3.83-3.75 (m, 1H), 1.93-1.84 (m, 2H), 1.71 (d, 2H), 1.61-1.55 (m, 3H), 1.19 (q, 2H), 1.05 (t, 1H).

[0163] (Synthesis Example 20: Synthesis of Compound (A97)) Under a nitrogen atmosphere, 0.81 g (2.0 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.12 g (2.1 mmol) of 2-aminoacetonitrile, 0.34 g (3.0 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 10 mL of DMF were added to a 50 mL two-necked flask and stirred at 140 °C for 7 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was recrystallized in a mixed solvent of xylene and hexane to obtain the target compound (A97) (0.37 g, yield 42%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.66-7.61 (m, 3H), 7.57 (d, 1H), 7.52-7.34 (m, 9H), 6.25 (d, 1H), 4.58 (s, 2H).

[0164] (Synthesis Example 21: Synthesis of Compound (A100)) Under a nitrogen atmosphere, 0.50 g (1.2 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.22 g (1.3 mmol) of 2-amino-2-phenylacetonitrile hydrochloride, 0.24 g (2.2 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 12 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 5 hours. After cooling to room temperature, the target compound (A100) was obtained by filtration of the solid (0.39 g, yield 61%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.61-7.33 (m, 18H), 6.67 (s, 1H), 6.20 (d, 1H).

[0165] (Synthesis Example 22: Synthesis of Compound (A103)) Under a nitrogen atmosphere, 1.45 g (3.6 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.63 g (3.8 mmol) of 1-adamantanemethylamine, 0.30 g (2.7 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 18 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the target compound (A103) was obtained by filtration of the solid (1.20 g, yield 61%). １ H-NMR (DMSO-d ６ ) δ (ppm): 7.61-7.59 (m, 3H), 7.53 (d, 1H), 7.49-7.29 (m, 9H), 6.18 (d, 1H), 3.07 (s, 2H), 1.86 (s, 3H), 1.55 (q, 6H), 1.37 (s, 6H).

[0166] (Synthesis Example 23: Synthesis of Compound (A119)) Under a nitrogen atmosphere, 2.00 g (5.0 mmol) of compound (20) obtained in Synthesis Reference Example 8, 1.50 g (5.1 mmol) of 3,3'-(4-aminopyridine-2,6-diyl)dibenzonitrile, 0.42 g (3.7 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 25 mL of xylene were added to a 100 mL two-necked flask and stirred at 140 °C for 10 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was stirred in 50 mL of toluene at 110 °C, cooled to room temperature, and the solid was collected by filtration to obtain the target compound (A119) (3.25 g, yield 96%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.62 (s, 2H), 8.48 (d, 2H), 8.13 (s, 2H), 7.96 (d, 2H), 7.75 (t, 2H), 7.66-7.35 (m, 13H), 6.25 (d, 1H).

[0167] (Synthesis Example 24: Synthesis of Compound (A120)) Under a nitrogen atmosphere, 1.45 g (3.6 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.92 g (3.8 mmol) of 4-(2-aminophenyl)-1-naphthonitrile, 0.30 g (2.7 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 18 mL of xylene were added to a 100 mL two-necked flask and stirred at 140 °C for 15 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was recrystallized in a mixed solvent of chlorobenzene and 1-butanol to obtain the target compound (A120) (1.30 g, yield 57%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.21-8.13 (m, 2H), 7.80-7.75 (m, 1H), 7.70-7.62 (m, 2H), 7.59-7.26 (m, 16H), 7.01-6.72 (m, 2H), 6.13 (dd, 1H).

[0168] (Synthesis Example 25: Synthesis of Compound (A129)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.22 g (0.89 mmol) of 3,5-di(4-pyridyl)aniline, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the precipitated solid was collected by filtration. After cooling to room temperature, the target compound (A129) was obtained by filtration of the solid (0.45 g, yield 95%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.66 (dd, 4H), 8.20 (s, 1H), 7.87 (d, 2H), 7.80-7.78 (dd, 4H), 7.60-7.45 (m, 13H), 6.24 (d, 1H).

[0169] (Synthesis Example 26: Synthesis of Compound (A131)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (20) obtained in Synthesis Reference Example 8, 0.20 g (0.89 mmol) of 4-(4-pyridyl)naphthalene-1-amine, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the precipitated solid was collected by filtration. After cooling to room temperature, the target compound (A131) was obtained by filtration of the solid (0.43 g, yield 96%). Mass spectrometry (QTOF-MS): 605

[0170] (Synthesis Example 27: Synthesis of Compound (A137)) Under a nitrogen atmosphere, 1.3 g (5.2 mmol) of compound (17) obtained in Synthesis Reference Example 5, 0.74 g (6.2 mmol) of 4-aminobenzonitrile, 0.47 g (3.6 mmol) of isoquinoline, and 35 mL of m-cresol were added to a 100 mL three-necked flask and stirred at 150 °C for 15 hours. After cooling to room temperature, water and ethanol were added, and the precipitated solid was collected by filtration and washed with ethanol. Next, the obtained solid was recrystallized with dimethylformamide / toluene to obtain the target compound (A137) (1.4 g, yield 78%). １ H-NMR (DMSO-d６ ) δ (ppm): 8.56 (s, 1H), 8.17 (dd, 1H), 8.07-8.03 (m, 3H), 7.78-7.72 (m, 4H), 7.55 (ddd, 1H). Mass spectrometry (QTOF-MS): 350

[0171] (Synthesis Example 28: Synthesis of Compound (A141)) The procedure was the same as in Synthesis Example 27, except that 0.89 g (6.2 mmol) of 4-aminophthalonitrile was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (A141) (0.62 g, yield 32%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.61 (s, 1H), 8.36 (d, 1H), 8.28 (s, 1H), 8.19 (d, 1H), 8.10-8.07 (m, 2H), 7.79-7.75 (m, 2H), 7.56 (ddd, 1H).

[0172] (Synthesis Example 29: Synthesis of Compound (A142)) The procedure was the same as in Synthesis Example 27, except that 1.2 g (6.2 mmol) of 5-amino-2-cyanobenzotrifluoride was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (A142) (1.7 g, yield 70%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.60 (s, 1H), 8.41 (d, 1H), 8.22-8.18 (m, 2H), 8.09-8.06 (m, 2H), 7.79-7.75 (m, 2H), 7.56 (ddd, 1H). Mass spectrometry (QTOF-MS): 418

[0173] (Synthesis Example 30: Synthesis of Compound (A147)) The procedure was the same as in Synthesis Example 27, except that 1.2 g (6.2 mmol) of 2'-amino-[1,1'-biphenyl]-4-carbonitrile was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (A147) (1.5 g, yield 67%). １ H-NMR (DMSO-d ６) δ (ppm): 8.43 (s, 1H), 8.10 (d, 1H), 7.93 (s, 1H), 7.80 (d, 2H), 7.75-7.71 (m, 2H), 7.69-7.59 (m, 4H), 7.52 (ddd, 1H), 7.41 (d, 2H).

[0174] (Synthesis Example 31: Synthesis of Compound (A148)) The procedure was the same as in Synthesis Example 27, except that 1.4 g (6.2 mmol) of 2-amino-[1,1'-biphenyl]-4,4'-dicarbonitrile was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (A148) (1.6 g, yield 68%). １ H-NMR (CDCl ３ ) δ (ppm): 8.08 (s, 1H), 7.95 (s, 1H), 7.89 (dd, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.69-7.60 (m, 5H), 7.48 (ddd, 1H), 7.38 (d, 2H).

[0175] (Synthesis Example 32: Synthesis of Compound (A156)) The procedure was the same as in Synthesis Example 27, except that 1.5 g (6.2 mmol) of [1,1':2',1''-terphenyl]-4'-amine was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (A156) (1.4 g, yield 55%). Mass spectrometry (QTOF-MS): 477 １ H-NMR (CDCl ３ ) δ (ppm): 8.08 (s, 1H), 7.95 (s, 1H), 7.89 (dd, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.69-7.60 (m, 5H), 7.48 (ddd, 1H), 7.38 (d, 2H).

[0176] (Synthesis Example 33: Synthesis of Compound (A157)) Under a nitrogen atmosphere, 1.3 g (5.2 mmol) of compound (17) obtained in Synthesis Reference Example 5, 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride, 0.34 g (3.0 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 35 mL of dimethylformamide were added to a 100 mL three-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, water and ethanol were added, and the precipitated solid was filtered and washed with ethanol. Next, the obtained solid was recrystallized with dimethylformamide / toluene to obtain the target compound (A157) (1.4 g, yield 50%). Mass spectrometry (QTOF-MS): 527

[0177] (Synthesis Example 34: Synthesis of Compound (A161)) The procedure was the same as in Synthesis Example 33, except that 0.74 g (6.2 mmol) of 4-aminopicolinonitrile was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride, to obtain the target compound (A161) (0.73 g, yield 40%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.95 (d, 1H), 8.61 (s, 1H), 8.24 (s, 1H), 8.20 (d, 1H), 8.09 (s, 1H), 7.77 (ddd, 1H), 7.56 (ddd, 1H).

[0178] (Synthesis Example 35: Synthesis of Compound (A162)) The procedure was the same as in Synthesis Example 33, except that 0.74 g (6.2 mmol) of 5-aminopicolinonitrile was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride, to obtain the target compound (A162) (1.1 g, yield 59%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.93 (d, 1H), 8.59 (s, 1H), 8.30-8.17 (m, 3H), 8.06 (s, 1H), 7.78-7.75 (m, 2H), 7.55 (ddd, 1H).

[0179] (Synthesis Example 36: Synthesis of Compound (A170)) The procedure was the same as in Synthesis Example 33, except that 0.89 g (6.2 mmol) of 4-aminoquinoline was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride to obtain the target compound (A170) (1.4 g, yield 70%). Mass spectrometry (QTOF-MS): 376

[0180] (Synthesis Example 37: Synthesis of Compound (A172)) The same procedure as in Synthesis Example 33 was followed, except that 1.5 g (6.2 mmol) of 4-amino-2,6-diphenylpyridine was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride to obtain the target compound (A172) (1.7 g, yield 68%). Mass spectrometry (QTOF-MS): 478

[0181] (Synthesis Example 38: Synthesis of Compound (A174)) The same procedure as in Synthesis Example 33 was followed, except that 0.91 g (6.2 mmol) of 2-amino-1-methyl-1H-imidazole-4,5-dicarbonitride was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride to obtain the target compound (A174) (0.67 g, yield 34%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.62 (s, 1H), 8.18 (d, 1H), 8.09 (s, 1H), 7.79-7.76 (m, 2H), 7.56 (ddd, 1H), 3.87 (s, 3H).

[0182] (Synthesis Example 39: Synthesis of Compound (A175)) The same procedure as in Synthesis Example 33 was followed, except that 0.78 g (6.2 mmol) of 2-amino-4-cyanothiazole was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitrile, to obtain the target compound (A175) (1.2 g, yield 65%). １ H-NMR (DMSO-d ６) δ (ppm): 8.84 (s, 1H), 8.61 (s, 1H), 8.19 (d, 1H), 8.08 (s, 1H), 7.79-7.75 (m, 2H), 7.55 (ddd, 1H).

[0183] (Synthesis Example 40: Synthesis of Compound (A180)) The procedure was the same as in Synthesis Example 33, except that 0.61 g (6.2 mmol) of aminoacetonitrile hydrochloride was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride to obtain the target compound (A180) (0.77 g, yield 43%). Mass spectrometry (QTOF-MS): 288

[0184] (Synthesis Example 41: Synthesis of Compound (A189)) The procedure was the same as in Synthesis Example 33, except that 1.5 g (6.2 mmol) of 2-amino-4,6-diphenylpyrimidine was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride to obtain the target compound (A189) (0.60 g, yield 24%). Mass spectrometry (QTOF-MS): 479

[0185] (Synthesis Example 42: Synthesis of Compound (A195)) The procedure was the same as in Synthesis Example 33, except that 1.2 g (6.2 mmol) of 3-amino-4-(pyridine-4-yl)benzonitrile was used instead of 1.8 g (6.2 mmol) of 5'-aminoterphenyl-4,4'-dicarbonitride, to obtain the target compound (A195) (1.1 g, yield 50%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.56 (dd, 2H), 8.47 (s, 1H), 8.21 (d, 1H), 8.18 (dd, 1H), 8.11 (d, 1H) , 7.96 (s, 1H), 7.86 (d, 1H), 7.76-7.72 (m, 2H), 7.53 (ddd, 1H), 7.30 (dd, 2H).

[0186] (Synthesis Example 43: Synthesis of Compound (A284)) Under a nitrogen atmosphere, 1.06 g (2.4 mmol) of compound (22) obtained in Synthesis Reference Example 10, 0.37 g (2.5 mmol) of 4-aminoquinoline, 0.20 g (1.8 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 24 mL of xylene were added to a 100 mL two-necked flask and stirred at 140 °C for 6 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The target compound (A284) was obtained by recrystallizing the obtained solid with xylene (0.80 g, yield 58%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.00 (d, 1H), 8.10 (d, 1H), 7.98 (d, 1H), 7.81 (t, 1H), 7.64-7.56 (m, 6H), 7.45-7.42 (m, 4H), 7.26 (t, 2H), 7.04 (s, 1H), 6.39 (d, 1H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -112.80, -113.77.

[0187] (Synthesis Example 44: Synthesis of Compound (A286)) Under a nitrogen atmosphere, 0.50 g (1.4 mmol) of compound (22) obtained in Synthesis Reference Example 10, 0.27 g (1.4 mmol) of 2'-amino-[1,1'-biphenyl]-4-carbonilolyl, 0.096 g (0.86 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 11 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 12 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was recrystallized in a mixed solvent of xylene and heptane to obtain the target compound (A286) (0.48 g, yield 69%). Mass spectrometry (QTOF-MS): 614

[0188] (Synthesis Example 45: Synthesis of Compound (A272)) Under a nitrogen atmosphere, 0.30 g (0.75 mmol) of compound (26) obtained in Synthesis Reference Example 14, 0.11 g (0.89 mmol) of 4-aminobenzonitrile, 0.063 g (0.56 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 7.5 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 4 hours. After cooling to room temperature, the target compound (A272) was obtained by filtering the precipitated solid (0.33 g, yield 73%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.17 (d, 1H), 8.11-8.07 (m, 3H), 8.03-7.97 (m, 3H), 7.95 (d, 1H) , 7.89 (d, 2H), 7.68-7.53 (m, 9H), 7.36 (t, 1H), 7.30 (t, 1H), 6.28 (d, 1H).

[0189] (Synthesis Example 46: Synthesis of Compound (A296)) Under a nitrogen atmosphere, 0.20 g (0.42 mmol) of compound (24) obtained in Synthesis Reference Example 12, 0.072 g (0.51 mmol) of 4-aminophthalonitrile, 0.035 g (0.32 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 4 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was recrystallized in a mixed solvent of xylene and heptane to obtain the target compound (A296) (0.15 g, yield 61%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.25 (d, 1H), 8.16 (d, 1H), 7.95 (dd, 1H), 7.65 (dd, 1H), 7.55 (tt, 1H), 7.48 (t, 2H), 7.40 (tt, 1H), 7.33-7.26 (m, 4H), 6.50 (d, 1H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -108.54, -111.18.

[0190] (Synthesis Example 47: Synthesis of Compound (A309)) Under a nitrogen atmosphere, 0.20 g (0.42 mmol) of compound (24) obtained in Synthesis Reference Example 12, 0.11 g (0.51 mmol) of 3-aminofluoranthene, 0.035 g (0.32 mmol) of 1,4-diazabicyclo[2.2.2]octane, and 4 mL of xylene were added to a 50 mL two-necked flask and stirred at 140 °C for 8 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The obtained solid was recrystallized in a mixed solvent of xylene and heptane to obtain the target compound (A309) (0.24 g, yield 85%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.20 (d, 1H), 8.15 (d, 1H), 8.08-8.05 (m, 2H), 7.85 (d, 1H), 7.71 (d, 1H), 7.68-7.66 (m, 2H), 7.55-7.31 (m, 10H), 6.51 (d, 1H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -108.61, -108.71. -111.29, -111.34.

[0191] (Synthesis Example 48: Synthesis of Compound (E1)) Under a nitrogen atmosphere, 1.5 g (3.1 mmol) of the compound (A147) obtained in Synthesis Example 30, 0.31 g (4.7 mmol) of malononitrile, and 30 mL of dimethylformamide were added to a 50 mL two-necked flask and stirred at 130 °C for 12 hours. After cooling to room temperature, water and ethanol were added, the precipitated solid was collected by filtration, and washed with ethanol. Next, the obtained solid was recrystallized with dimethylformamide / toluene to obtain the target compound (E1) (1.0 g, yield 68%). １ H-NMR (CDCl ３ ) δ (ppm): 8.81 (s, 1H), 8.50 (d, 1H), 7.99 (s, 1H), 7.72 (d, 1H), 7.66-7.56 (m, 5H), 7.53-7.47 (m, 2H), 7.41-7.37 (m, 3H).

[0192] (Evaluation Example 1: Film Quality Evaluation of Compound (A2)) A Si substrate (with native oxide film) was introduced into a vacuum deposition chamber, and 1.0 × 10 －４The pressure was reduced to Pa. Then, a 30 nm film of the sublimation-purified compound (A2) was deposited on the substrate, and the surface condition of the film was observed using an atomic force microscope (Shimadzu SPM-9600). The arithmetic mean roughness (Ra) measured in the surface roughness test was 0.37 nm.

[0193] (Evaluation Example 2: Film Quality Evaluation of Compound (A3)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A3) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.27 nm.

[0194] (Evaluation Example 3: Film Quality Evaluation of Compound (A16)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A16) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.31 nm.

[0195] (Evaluation Example 4: Film Quality Evaluation of Compound (A57)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A57) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.23 nm.

[0196] (Evaluation Example 5: Film Quality Evaluation of Compound (A65)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A65) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.92 nm.

[0197] (Evaluation Example 6: Film Quality Evaluation of Compound (A103)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A103) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.72 nm.

[0198] (Evaluation Example 7: Film Quality Evaluation of Compound (A147)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A147) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.98 nm.

[0199] (Evaluation Example 8: Film Quality Evaluation of Compound (A272)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A272) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.45 nm.

[0200] (Evaluation Example 9: Film Quality Evaluation of Compound (A284)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (A284) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.65 nm.

[0201] (Evaluation Comparative Example 1: Film Quality Evaluation of Compound (C1)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (C1) was used instead of Compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 5.07 nm. Compound (C1) was purchased from Tokyo Chemical Industry Co., Ltd. and purified by sublimation.

[0202] (Evaluation Reference Example 1: Film Quality Evaluation of Compound (D1)) The measurement was performed in the same manner as in Evaluation Example 1, except that compound (D1) was used instead of compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 3.45 nm. Compound (D1) was synthesized according to the method disclosed in J. Mater. Chem. A, 2015, 3, 878 and purified by sublimation.

[0203] (Evaluation Reference Example 2: Film Quality Evaluation of Compound (17)) The measurement was performed in the same manner as in Evaluation Example 1, except that compound (17) was used instead of compound (A2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 26.48 nm.

[0204]

[0205] Based on the above film quality evaluation, it was confirmed that the films prepared using the compounds of Evaluation Examples 1 to 9 exhibited even higher film smoothness than the films prepared using the compound (C1) of Evaluation Comparative Example 1, the compound (D1) of Evaluation Reference Example 1, and the compound (17) of Evaluation Reference Example 2.

[0206] <Fabrication and Evaluation of Photoelectric Conversion Elements> [Element Example 1] A photoelectric conversion element 1 having a laminated structure consisting of a substrate, a second electrode 16, an electron transport layer 15, a light-receiving layer 14, a hole transport layer 13, a hole transport enhancement layer 12, and a first electrode 11 was fabricated, and the dark current and external quantum efficiency of the photoelectric conversion element were evaluated.

[0207] [Compounds used for evaluation]

[0208] (Preparation of the substrate and second electrode 16) A glass substrate with a transparent ITO electrode, on which a 2 mm wide indium-tin (ITO) film (thickness 110 nm) was patterned in stripes, was prepared as a substrate with a second electrode on its surface. Next, this substrate was cleaned with isopropyl alcohol and then surface-treated by ozone ultraviolet cleaning. (Preparation for vacuum deposition) On the surface-treated substrate after cleaning, each layer was deposited by vacuum deposition using the vacuum deposition method to form a laminate of each layer. First, the glass substrate was introduced into the vacuum deposition chamber, and 7.0 × 10 －５ The pressure was reduced to Pa. Then, each layer was fabricated according to the following deposition conditions in the order below. (Fabrication of electron transport layer 15) The electron transport layer 15 was fabricated by depositing the sublimation-purified compound (A2) at a rate of 0.03 nm / second to a thickness of 10 nm. (Fabrication of light-receiving layer 14) The photoelectric conversion layer 14 was fabricated by depositing N,N-dimethylquinacridone and fullerene C60 in a ratio of 4:1 (mass ratio) to a thickness of 250 nm. The deposition rate was 0.13 nm / second. (Fabrication of hole transport layer 13) The hole transport layer 13 was fabricated by depositing (HTL-1) as the hole transport material at a rate of 0.10 nm / second to a thickness of 10 nm. (Fabrication of hole transport-promoting layer 12) Compound 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN) was deposited at a rate of 0.10 nm / second to a thickness of 10 nm to prepare the hole transport-promoting layer 12. (Fabrication of first electrode 11) Finally, a metal mask was placed perpendicular to the ITO stripe on the substrate, and the first electrode 11 was deposited. The first electrode was made of Au with a thickness of 80 nm. The deposition rate of Au was 0.1 nm / second.

[0209] Therefore, the area is 4 mm². ２A photoelectric conversion element 1, as shown in Figure 1, was fabricated. When a voltage of 2.5V (absolute value) was applied to the photoelectric conversion element fabricated as described above, such that electrons were transported to the second electrode 16 side and holes to the first electrode 11 side, the dark current (dark current, mA / cm²) was measured. ２ The dark current and external quantum efficiency were evaluated. Dark current was measured using a Keithley Source Measure Unit 2636B. A solar cell spectroscopic sensitivity analyzer (manufactured by Soma Optical Co., Ltd.) was used to measure the external quantum efficiency. The wavelength of the irradiated light was 560 nm, and the intensity was 1.6 μW / cm². ２ Measurements were performed using the following method: Response time: wavelength 560 nm, intensity 1.6 μW / cm². ２ The light was irradiated, and after stopping the irradiation, the time it took for the current value to return to the level before irradiation was measured.

[0210] The results are shown in Table 2. Note that the dark current and external quantum efficiency are relative values, with the results from Comparative Example 1 (described later) set as the baseline value (1). A lower dark current value indicates better performance, while a higher external quantum efficiency value indicates better performance.

[0211] [Device Example 2] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A7) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0212] [Device Example 3] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A12) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0213] [Device Example 4] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A16) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0214] [Element Example 5] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A19) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Element Example 1. The results are shown in Table 2.

[0215] [Element Example 6] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A28) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Element Example 1. The results are shown in Table 2.

[0216] [Device Example 7] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A57) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0217] [Device Example 8] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A65) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0218] [Device Example 9] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A97) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0219] [Element Example 10] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A103) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Element Example 1. The results are shown in Table 2.

[0220] [Device Example 11] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A119) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0221] [Device Example 12] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A120) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0222] [Device Example 13] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A147) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0223] [Device Example 14] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A284) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0224] [Device Example 15] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A309) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 2.

[0225] [Reference Element Example 1] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (E1) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Element Example 1. The results are shown in Table 2.

[0226] [Comparative Element Example 1] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (R-1) was used instead of compound (A2) in the fabrication of the electron transport layer 15. The dark current and external quantum efficiency were measured in the same manner as in Element Example 1. The results are shown in Table 2. (R-1) was synthesized by the method described in Journal of the American Chemical Society (2011), 133(39), 15256-15259.

[0227]

[0228] As shown in Table 2, the elements of Examples 1 to 15 using the material for photoelectric conversion elements for image sensors of the present invention showed suppressed dark current and superior responsiveness compared to Comparative Example 1. Furthermore, the devices using compounds (A3), (A13), (A20), (A21), (A31), (A32), (A77), (A79), (A91), (A92), (A94), (A100), (A129), (A131), (A137), (A141), (A142), (A148), (A156), (A157), (A161), (A162), (A170), (A172), (A174), (A175), (A180), (A189), (A195), (A286), and (A296) synthesized in the synthesis example also showed the same ability to suppress dark current and improve responsiveness as in Element Example 1. Furthermore, in Element Example 4 and Element Example 13, dark current was suppressed and excellent responsiveness was observed compared to Element Reference Example 1. Therefore, it is considered that the compound represented by formula (1) can enhance electron transport capability when used in organic electronic devices due to intermolecular interactions mediated by the ketone group.

[0229] The organic electronic element of the present invention, by containing the compound represented by formula (1) above, can improve electron transport capability and, when used in a photoelectric conversion element, can perform photoelectric conversion more efficiently. Furthermore, by containing the compound represented by formula (1) above, the organic electronic element of the present invention suppresses dark current, and is expected to reduce noise when used in a photoelectric conversion element such as an image sensor. Moreover, by containing the compound represented by formula (1) above, the organic electronic element of the present invention can have high external quantum efficiency and can convert light into electric current without loss, so, for example, when used in a photoelectric conversion element, high sensitivity can be expected.

[0230] 1. Photoelectric conversion element 11. First electrode 12. Hole transport enhancement layer 13. Hole transport layer 14. Light receiving layer 15. Electron transport layer 16. Second electrode 2. Organic EL element 21. First electrode 22. Hole injection layer 23. Hole transport layer 24. Light emitting layer 25. Electron transport layer 26. Second electrode

Claims

1. An organic electronic element comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an electron transport layer, and the electron transport layer includes a compound represented by the following formula (1). (In formula (1), R a Each independently represents a hydrogen atom, a hydroxyl group, a thiol group, an amino group, a cyano group, a carboxyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. n represents an integer from 0 to 2. When n is 2, R a They may be the same or different from each other. １ R represents a single bond, a linear, branched, or cyclic (n+1) valency aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n+1) valency aromatic hydrocarbon group having 6 to 18 carbon atoms, or a (n+1) valency heteroaromatic group having 3 to 20 carbon atoms. The aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings. １ ~R ６ Each of these independently represents a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, an iodo group, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups.

2. In the above formula (1), the above R a , the above L １ , and the above R １ to R ６ , the optional substituents are each independently a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, a linear, branched or cyclic alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a combination of these groups. The organic electronic device according to claim 1.

3. The organic electronic element according to claim 1, further comprising a light-receiving layer disposed between the first electrode and the second electrode.

4. The organic electronic element according to claim 3, wherein the light-receiving layer is a layer containing at least two organic components.

5. The organic electronic element according to claim 1, wherein the organic layer further comprises a hole transport layer.

6. In formula (1) above, R １ and R ２ The organic electronic element according to claim 1, wherein each is independently a hydrogen atom, a phenyl group, or a naphthyl group.

7. In formula (1) above, R ３ , the R ４ and R ６ is a hydrogen atom, and the R ５ The organic electronic element according to claim 1, wherein is any of a hydrogen atom, a cyano group, a trifluoromethyl group, a methoxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a phenyl group, or a pyridyl group.

8. An imide compound represented by the following formula (2). (In formula (2), R ｂ Each independently represents a hydrogen atom, a hydroxyl group, a thiol group, an amino group, a cyano group, a carboxyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. n represents an integer from 0 to 2. When n is 2, R ｂ They may be the same or different from each other. ２ R represents a single bond, a linear, branched, or cyclic (n+1) valency aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n+1) valency aromatic hydrocarbon group having 6 to 18 carbon atoms, or a (n+1) valency heteroaromatic group having 3 to 20 carbon atoms. The aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings. １１ ~R １６ Each of these independently represents a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, an iodo group, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups. However, L ２ If it is a single bond, R ｂ (This refers to any group other than a phenyl group (limited to phenyl groups without substituents).) 9. In formula (2) above, R ｂ , said L ２ , and the R １１ ~R １６ The imide compound according to claim 8, wherein the substituents that may be present are, each independently, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a methoxy group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, a linear, branched, or cyclic alkyl group having 2 to 10 carbon atoms, an alkoxy group having 2 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a combination thereof.

10. In formula (2) above, R ｂ The imide compound according to claim 8, wherein each of the groups is independently an alkyl group, a cycloalkyl group, an adamantyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a bipyridyl group, a terpyridyl group, a pyrazyl group, a pyrimidyl group, a triazyl group, a quinolyl group, a quinoxalinyl group, a quinazolyl group, an imidazolyl group, a benzimidazolyl group, a thiazolyl group, a benzothiazolyl group, an oxazolyl group, or a benzoxazolyl group, and these groups may have substituents.

11. In formula (2) above, L ２ The imide compound according to claim 8, wherein the group is a single bond, (n+1)-valent benzene, (n+1)-valent naphthalene, (n+1)-valent pyridine, or (n+1)-valent pyrimidine, and these groups may have substituents.

12. In formula (2) above, R １１ and R １２ The imide compound according to claim 8, wherein each is independently a hydrogen atom, a phenyl group, or a naphthyl group.

13. In formula (2) above, R １３ , the R １４ and R １６ is a hydrogen atom, and the R １５ The imide compound according to claim 8, wherein is any of a hydrogen atom, a cyano group, a trifluoromethyl group, a methoxy group, a fluoro group, a chloro group, a bromo group, an iodo group, a phenyl group, or a pyridyl group.

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