Organic electronic element, imide compound, acid anhydride derivative, and method for producing same

Abstract

The present invention provides: an organic electronic element and an imide compound which are capable of improving hole transport ability; and an acid anhydride derivative, and a method for producing the same.　The organic electronic element comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a moiety represented by formula (1). In formula (1), X1 and X2 are each bonded to a divalent group represented by formula (2) or formula (3), and * represents bonding site.　In addition, Y1 represents an oxygen atom or one of formulae (a)-(h).

Description

Organic electronic devices, imide compounds, acid anhydride derivatives, and methods for producing the same.

[0001] The present invention relates to organic electronic devices, imide compounds, acid anhydride derivatives, and methods for producing the same.

[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 hole transport capability, as well as an acid anhydride derivative and a method for producing the same.

[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 substructure can improve the hole 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 contains a compound having a substructure represented by the following formula (1). (In formula (1), X １ and X ２ are each bonded to a divalent group represented by the following formula (2) or (3), and * represents a bond.) R a are each independently 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, and the alkyl group, the aromatic hydrocarbon group and the heteroaromatic group may have a substituent. n represents an integer of 0 to 2. L １ represents a single bond, a linear, branched or cyclic (n + 1)-valent aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n + 1)-valent aromatic hydrocarbon group having 6 to 18 carbon atoms, or an (n + 1)-valent heteroaromatic group having 3 to 20 carbon atoms, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group and the heteroaromatic group may have a substituent. R １ to R ６ are each independently 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, and the aromatic hydrocarbon group and the heteroaromatic group may have one or more of a substituent and a linking group. Y １ represents an oxygen atom or any one of the following formulas (a) to (h).) [2] The R a the L １ and the R １ to R ６The organic electronic element according to [1], wherein the substituent which may be present is 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, an 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, or a heteroaromatic group having 3 to 20 carbon atoms. [3] The organic electronic element according to [1] or [2], comprising a first electrode, a second electrode, and an organic layer and a light-receiving layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a substructure represented by formula (1). [4] The organic electronic element according to [3], wherein the light-receiving layer is a layer containing at least two organic components. [5] 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 a hole transport layer and a hole transport promoting layer containing a compound having a substructure represented by formula (1), or a layer obtained by mixing a hole transport material and a compound having a substructure represented by formula (1), as described in any of [1] to [4]. [6] The organic electronic element according to [5], wherein the hole transport layer and the hole transport promoting layer are disposed adjacent to each other between the first electrode and the second electrode. [7] The organic electronic element according to any of [1] to [6], wherein formula (1) is formula (1a) or (1b) below. (In formula (1a) or (1b), 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. n represents an integer from 0 to 2. L １R 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, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups. １ represents any of the above formulas (a) to (h). ) [8] In formula (1a) or (1b), R １ and R ２ The organic electronic element described in [7], wherein each is independently a hydrogen atom or a phenyl group. [9] In formula (1a) or (1b), R １ , R ２ , R ３ , R ４ and R ６ is a hydrogen atom, R ５ The organic electronic element according to [7] or [8], 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.

[10] In formula (1a), Y １ An organic electronic element according to any one of [1] to [9], wherein is the above formula (a).

[11] An imide compound represented by the following formula (4). (In formula (4), R ｂEach 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. n represents an integer from 0 to 2. L 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 an (n+1) valency heteroaromatic group having 3 to 20 carbon atoms, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and / or linking groups. ２ This represents one of the following equations (a) to (h).

[12] In formula (4), the R ｂ , said L ２ , and the R １１ ~R １６ In the present invention, the substituent which may be present is 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, an 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, or a heteroaromatic group having 3 to 20 carbon atoms, the imide compound according to

[11] .

[13] In formula (4), the R ｂHowever, 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 each group may have a substituent. The imide compound according to

[11] or

[12] .

[14] L ２ The imide compound according to any one of

[11] to

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

[15] In formula (4), R １１ and R １２ However, each is independently a hydrogen atom or a phenyl group, an imide compound according to any one of

[11] to

[14] .

[16] In formula (4), R １１ , R １２ , R １３ , R １４ and R １６ is a hydrogen atom, R １５ The imide compound according to any one of

[11] to

[15] , 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.

[17] In formula (4), Y ２ An imide compound according to any one of

[11] to

[16] , wherein is the above formula (a).

[18] An acid anhydride derivative represented by the following formula (5). (In formula (5), R ２１ ~R ２６Each 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups.)

[19] In formula (5), R ２１ and R ２２ The acid anhydride derivative described in

[18] , wherein each is independently a hydrogen atom or a phenyl group.

[20] In formula (5), R ２１ , R ２２ , R ２３ , R ２４ and R ２６ is a hydrogen atom, R ２５ An acid anhydride derivative according to

[18] or

[19] , 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.

[21] A method for producing an acid anhydride derivative according to any one of

[18] to

[20] , comprising reacting a biphenyl derivative represented by the following general formula (6) in the presence of an acid catalyst to perform ring closure. (In formula (6), R ２１ ~R ２６ 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, a monocyclic, linking, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monocyclic, linking, or fused heteroaromatic group having 3 to 20 carbon atoms, and the aromatic hydrocarbon group and the heteroaromatic group may have substituents. ３１ ~R ３３ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

[0008] According to the present invention, it is possible to provide an organic electronic element, a hole transport promoting material, and an imide compound that can improve the hole transport capability.

[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 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 contains a compound having a substructure represented by the following formula (1) (hereinafter also referred to as the compound represented by formula (1)).

[0012] A detailed explanation of the compound represented by formula (1) above will be given later. The organic layer preferably includes a hole transport layer and a hole transport promoting layer containing the compound represented by formula (1) above, or a layer obtained by mixing a hole transport material and the compound represented by formula (1) above. Here, the hole transport layer has the role of transporting holes and contains a hole transport material. The hole transport promoting layer is placed between the first electrode and the hole transport layer and has the role of facilitating hole transport and the exchange of holes between the electrode and the electrode, and contains a hole transport promoting material. In the present invention, the compound represented by formula (1) above is not particularly limited, but can be used as a hole transport promoting material.

[0013] A photoelectric conversion element is a preferred embodiment of the organic electronic element of the present invention. The photoelectric conversion element 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 a hole transport region. The hole transport region refers to the region between the first electrode and the light-receiving layer, and includes, for example, a hole transport layer and a hole transport-promoting layer. In the present invention, a compound represented by the above formula (1) can be used as the hole transport-promoting material contained in the hole transport-promoting layer. The hole transport region is preferably adjacent to the first electrode. The photoelectric conversion element may include other layers. Examples of other layers include, but are not limited to, a light-receiving layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a buffer layer, etc.

[0015] The photoelectric conversion element according to the present invention may be configured such that, for example, a first electrode, a hole transport enhancement layer, a hole transport layer, and a second electrode are stacked in this order, or a first electrode, a layer formed by mixing a hole transport material that forms the hole transport layer with a compound represented by formula (1) above, and a second electrode are stacked in this order. Alternatively, the photoelectric conversion element may be configured such that, for example, a first electrode, a hole transport enhancement layer, and a hole transport layer are stacked adjacent to each other in this order, or other layers such as a buffer layer may be interposed between the first electrode and the hole transport enhancement layer, or between the hole transport enhancement layer and the hole transport layer.

[0016] In one 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, 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 a hole transport region. The hole transport region refers to the region between the first electrode and the light-emitting layer, and includes, for example, a hole transport layer and a hole injection layer. In the present invention, a compound represented by the above formula (1) can be used as the material contained in the hole injection layer. The hole transport region is preferably adjacent to the first electrode. The organic EL element may include other layers. Other layers include, but are not limited to, layers commonly used in organic EL elements. Examples include, a light-emitting layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a buffer layer, etc.

[0020] The organic EL element according to the present invention is, for example, stacked in the order of a first electrode, a hole injection layer, a hole transport layer, and a second electrode, or stacked in the order of a first electrode, a layer formed by mixing a hole transport material that forms the hole transport layer with a compound represented by formula (1), and a second electrode. Alternatively, the organic EL element may be stacked adjacent to each other in the order of a first electrode, a hole injection layer, and a hole transport layer, or other layers such as a buffer layer may be interposed between the first electrode and the hole injection layer, or between the hole injection layer and the hole transport layer.

[0021] In one 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, 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) (imide compound)> The organic layer in the organic electronic device of the present invention contains a compound represented by the following formula (1) (imide compound).

[0025]

[0026] In formula (1), X １ and X ２ Y bonds with a divalent group represented by the following formulas (2) or (3). １ represents either an oxygen atom or one of the following formulas (a) to (h).

[0027] X １ and X ２ X bonds with a divalent group represented by the following formulas (2) or (3). １ and X ２ It is preferable that each of these bonds with the divalent group represented by formula (2) above. In the following formula, * represents a bond.

[0028] 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents.

[0029] In this specification, examples of linear, branched, or cyclic alkyl groups having 3 to 18 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, heptyl, 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.

[0030] R aIn this context, preferred substituents that the alkyl group, aromatic hydrocarbon group, and heteroaromatic group described above may have include cyano group, fluoro group, chloro group, bromo group, iodo group, trifluoromethyl group, methyl group, methoxy group, cyanoalkyl group having 2 to 10 carbon atoms, fluoroalkyl group having 2 to 10 carbon atoms, fluoroalkoxy group having 1 to 10 carbon atoms, alkyl group having 2 to 10 carbon atoms, alkoxy group having 2 to 18 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, aromatic hydrocarbon group having 6 to 30 carbon atoms, or heteroaromatic group having 3 to 20 carbon atoms. In terms of ease of synthesis, the substituents that alkyl groups, aromatic hydrocarbon groups, and heteroaromatic groups may have are more preferably cyano, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy, isopropyl, tert-butyl, phenoxy, phenyl, cyanophenyl, fluorophenyl, (trifluoromethyl)phenyl, pyridyl, cyanopyridyl, fluoropyridyl, and (trifluoromethyl)pyridyl groups, and particularly preferably cyano, fluoro, trifluoromethyl, methyl, tert-butyl, phenoxy, phenyl, cyanophenyl, (trifluoromethyl)phenyl, pyridyl, cyanopyridyl, and (trifluoromethyl)pyridyl groups.

[0031] R aIn terms of ease of synthesis, methyl group, cyano group, cyanomethyl group, dicyanomethyl group, ethyl group, cyanoethyl group, fluoroethyl group, propyl group, bromopropyl group, butyl group, isobutyronitrile 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, isopropyl Phenyl 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, pentyloxyphenyl group, isopentyloxy Phenyl 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, shea No-(trifluoromethyl)phenyl 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, crisenyl 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 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, methylpyridyl 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, cyanopyridyl group, fluoropyridyl group, (trifluoromethyl)pyridyl group, pyrimidyl group, methylpyridyl group, dimethylpyridyl group, cyanopyridyl group, dicyanopyridyl group Anopyrimidyl 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, methylcarbazolyl group, phenylcarbazolyl group,A thianthrenyl group, phenothiazinyl group, phenylphenothiazinyl group, phenoxazinyl group, or phenylphenoxazinyl group is preferred.

[0032] Also, R aThese include cyanomethyl group, cyanoethyl group, n-propyl group, n-butyl 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, and 3,5-di-tert-butylphenyl Phenyl 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, p-terphenyl group, m-terphenyl group, o-terphenyl 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 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, 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'-spirobifluoren-2-yl group, 9,9'-spirobifluoren-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-Crysenyl group, 6-Crysenyl 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-Dicyano-1-Imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 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 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-oxazolyl 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 group, 5-(trifluoromethyl)-2-benzo[d]oxazolyl group, 6-(trifluoromethyl (L)-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, 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 Fluoropropyl 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-trifluoromethyl-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-bi Su(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)-1,35-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, 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 It is even more preferable that the group is a 2-furanyl group, a 3-furanyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 2-dibenzofuranyl group, a 4-dibenzofuranyl group, a 9-methylcarbazole-2-yl group, 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.

[0033] And R aExamples include cyanomethyl group, n-propyl group, n-butyl 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, 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 1-L group, 2-naphthyl group, 4-cyanonaphthalen-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, 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-thiazolyl 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 Dyl 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, pyrazyl group, 5-cyanopyrazine-2- Iyl 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-2-yl group, 4,A 6-bis(3-pyridyl)-1,3,5-triazine-2-yl group, a 4-quinolyl group, a 5-quinolyl group, an 8-quinolyl group, a 6-quinoxalyl group, a 2-quinazolyl group, a 4-quinazolyl group, a 1,10-phenanthroline-5-yl group, a 2-dibenzothienyl group, a 4-dibenzothienyl group, a 2-dibenzofuranyl group, or a 4-dibenzofuranyl group is particularly preferred.

[0034] n represents an integer between 0 and 2. For ease of composition, n is preferably 1 or 2, and particularly preferably 1.

[0035] L １ L 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, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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, 2,4-pyridylene group, 2,5-pyridylene group or 2,6-pyridylene group) being even more preferred. Each group may have substituents, and preferred substituents are methyl groups, cyano groups, fluoro groups or trifluoromethyl groups.

[0036] Y １ represents either an oxygen atom or one of the following formulas (a) to (h).

[0037] Y １ From the viewpoint of raw material availability, (a), (e), (f), (g), or (h) are preferred, (a), (e), (f), or (h) are more preferred, and (a) is particularly preferred.

[0038] R １ ~R ６is, independently of each other, 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, and the aromatic hydrocarbon group and the heteroaromatic group may have one or more of a substituent and a linking group. R １ ~R ６ From the viewpoints of synthesis and device performance, R １ and R ２ are each preferably independently a hydrogen atom or a phenyl group, and it is also preferable that R １ , R ２ , R ３ , R ４ and R ６ are hydrogen atoms, and R ５ 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.

[0039] L １ , and R １ ~R ６ In, the substituents that may be possessed include the same ones as the substituents that may be possessed in the above R a .

[0040] The compound represented by the formula (1) described above is preferably a compound represented by the following formula (1a) or (1b).

[0041] In the formula (1a) or (1b), R a are each independently 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, and the alkyl group, the aromatic hydrocarbon group and the heteroaromatic group may have a substituent. n represents an integer of 0 to 2.

[0042] L １ represents a single bond, a linear, branched, or cyclic (n + 1)-valent aliphatic hydrocarbon group having 1 to 18 carbon atoms, an (n + 1)-valent aromatic hydrocarbon group having 6 to 18 carbon atoms, or an (n + 1)-valent heteroaromatic group having 3 to 20 carbon atoms, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. L １ From the viewpoint of device performance, it is preferably a single bond, (n + 1)-valent benzene, (n + 1)-valent naphthalene, (n + 1)-valent pyridine, or (n + 1)-valent pyrimidine, particularly preferably a single bond, (n + 1)-valent benzene, or (n + 1)-valent pyridine, and more preferably 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). Each group may have a substituent, and the substituent is preferably a methyl group, a cyano group, a fluoro group, or a trifluoromethyl group.

[0043] R １ ~R ６ each 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, and the aromatic hydrocarbon group and the heteroaromatic group may have one or more of a substituent and a linking group. R １ ~R ６ From the viewpoints of synthesis and device performance, R １ and R ２ are each independently preferably a hydrogen atom or a phenyl group, and it is also preferable that R １ , R ２ , R ３ , R ４ and R ６ are hydrogen atoms, and R ５ 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. R１ and R ２ Each of these is more preferably a hydrogen atom or a phenyl group, independently of the others. １ , R ２ , R ３ , R ４ and R ６ is a hydrogen atom, R ５ It is particularly 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.

[0044] Y １ This represents one of the above formulas (a) to (h). Y １ From the viewpoint of raw material availability, (a), (e), (f), (g), or (h) are preferred, (a), (e), (f), or (h) are more preferred, and (a) is particularly preferred.

[0045] 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.

[0046] 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 as a hole transport-enhancing layer.

[0047] Preferred examples of imide compounds represented by formula (1) include, for example, (A1) to (A135) below. However, the compounds of the present invention are not limited to these.

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Of the above, (A1) to (A3), (A6) to (A10), (A15) to (A24), (A28) to (A90), (A97) to (A101), (A106) to (A117), and (A121) to (A130) are even more preferable in order to enhance interaction with adjacent layers such as hole transport layers. Furthermore, from the viewpoint of smoothness during film formation, (A1), (A2), (A3), (A7), (A8), (A9), (A10), (A15), (A16), (A18), (A20), (A23), (A24), (A28), (A29), (A31), (A32), (A33), (A34), (A35), (A37), (A39), (A40), (A41), (A43), (A45), (A46), (A52), (A53), (A54), (A55), (A56) (A57), (A65), (A66), (A67), (A68), (A71), (A72), (A77), (A78), (A79), (A81), (A82), (A84), (A87), (A88), (A89), (A97), (A100), (A106), (A107), (A112), (A114), (A115), (A116), (A117), (A121), (A122), (A123), (A124), (A129) are particularly preferred.

[0058] [Manufacturing method] For example, Y １When is represented by formula (a), the compound represented by formula (1a') can be synthesized by known methods or combinations thereof. For example, an acid anhydride derivative represented by formula (1b) is reacted with an amine compound represented by formula (11) to obtain a compound represented by formula (12) (Step 1). Furthermore, the obtained compound represented by formula (12) is reacted with a malononitrile represented by formula (a) to synthesize an imide compound represented by formula (1a') (Step 2). The imide compound represented by formula (1a') can be synthesized in two steps (Steps 1 and 2) in this way, or it can be synthesized in one step.

[0059] (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.

[0060] The reactions in steps 1 and 2 may be carried out in a reaction solvent. Preferred 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 carbonates 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, cresol, DMF, DMAc, DMSO, pyridine, quinoline, and mixed solvents thereof are preferred for their good reaction yield.

[0061] Furthermore, the reaction in steps 1 and 2 can be accelerated by carrying out the reaction 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, isoquinoline, 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). Of these, isoquinoline or 1,4-diazabicyclo[2.2.2]octane is more preferred as the condensing agent used in step 1 because it yields a good reaction yield of the compound represented by formula (12). Furthermore, pyridine or titanium tetrachloride is more preferred as the condensing agent used in step 2 because it yields a good reaction yield of the imide compound represented by formula (1a').

[0062] 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 (12) or the acid anhydride derivative represented by formula (1b). The amount of amine compound represented by formula (11) used is preferably 1.0 to 1.2 moles per mole of the compound represented by formula (1b) in terms of reaction yield and production efficiency. The amount of formula (a) used is preferably 1.0 to 2.0 moles per mole of the compound represented by formula (12) in terms of reaction yield and production efficiency.

[0063] 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.

[0064] <<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 this strong acceptor skeleton is expected to facilitate strong interaction with the HOMO orbitals of hole transport materials. In other words, by containing the above compound in a layer (e.g., a hole transport-promoting layer) in an organic electronic device (e.g., a photoelectric conversion device), the interaction with the HOMO orbitals of the adjacent hole transport layer is increased, and it is expected that carrier transfer between the hole transport layer and the hole transport-promoting layer will be promoted. Thus, because the above compound has an extremely deep LUMO level, it is expected that the exchange of holes between the hole transport layer and the electrode will be smoother. Furthermore, because the above compound has an imide structure containing a fluorene ring, thermal stability and high reduction resistance can also be expected.

[0065] As described above, the inventors have found that the compound represented by formula (1) can be effectively used as a hole transport promoting material to facilitate the exchange of holes between the hole transport layer and the electrode. They have also confirmed that when the compound represented by formula (1) (hole transport promoting material) is combined with a hole transport material in a photoelectric conversion element, the hole 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 hole transport promoting material of this application.

[0066] (Imide Compounds) The present invention relates to imide compounds represented by the following formula (4). In formula (4), R 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and / or linking groups. ２This represents one of the following equations (a) to (h).

[0067] 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. n represents an integer from 0 to 2. Also, R ｂ In this context, examples of substituents that may be present include cyano groups, fluoro groups, chloro groups, bromo groups, iodo groups, trifluoromethyl groups, methyl groups, methoxy groups, cyanoalkyl groups having 2 to 10 carbon atoms, fluoroalkyl groups having 2 to 10 carbon atoms, fluoroalkoxy groups having 1 to 10 carbon atoms, alkyl groups having 2 to 10 carbon atoms, alkoxy groups having 2 to 18 carbon atoms, trialkylsilyl groups having 3 to 18 carbon atoms, aromatic hydrocarbon groups having 6 to 30 carbon atoms, or heteroaromatic groups having 3 to 20 carbon atoms.

[0068] 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 each group may have substituents.

[0069] R ｂIn terms of ease of synthesis, methyl group, cyano group, cyanomethyl group, dicyanomethyl group, ethyl group, cyanoethyl group, fluoroethyl group, propyl group, bromopropyl group, butyl group, isobutyronitrile 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, isopropyl Phenyl 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, pentyloxyphenyl group, isopentyloxy Phenyl 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, shea No-(trifluoromethyl)phenyl 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, crisenyl 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 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, methylpyridyl 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, cyanopyridyl group, fluoropyridyl group, (trifluoromethyl)pyridyl group, pyrimidyl group, methylpyridyl group, dimethylpyridyl group, cyanopyridyl group, dicyanopyridyl group Anopyrimidyl 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, methylcarbazolyl group, phenylcarbazolyl group,A thianthrenyl group, phenothiazinyl group, phenylphenothiazinyl group, phenoxazinyl group, or phenylphenoxazinyl group is preferred.

[0070] Also, R ｂThese include cyanomethyl group, cyanoethyl group, n-propyl group, n-butyl 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, and 3,5-di-tert-butylphenyl Phenyl 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, p-terphenyl group, m-terphenyl group, o-terphenyl 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 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, 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'-spirobifluoren-2-yl group, 9,9'-spirobifluoren-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-Crysenyl group, 6-Crysenyl 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-Dicyano-1-Imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 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 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-oxazolyl 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 group, 5-(trifluoromethyl)-2-benzo[d]oxazolyl group, 6-(trifluoromethyl (L)-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, 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 Fluoropropyl 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-trifluoromethyl-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-bi Su(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)-1,35-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, 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 It is even more preferable that the group is a 2-furanyl group, a 3-furanyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 2-dibenzofuranyl group, a 4-dibenzofuranyl group, a 9-methylcarbazole-2-yl group, 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.

[0071] And R ｂExamples include cyanomethyl group, n-propyl group, n-butyl 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, 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 1-L group, 2-naphthyl group, 4-cyanonaphthalen-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, 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-thiazolyl 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 Dyl 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, pyrazyl group, 5-cyanopyrazine-2- Iyl 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-2-yl group, 4,A 6-bis(3-pyridyl)-1,3,5-triazine-2-yl group, a 4-quinolyl group, a 5-quinolyl group, an 8-quinolyl group, a 6-quinoxalyl group, a 2-quinazolyl group, a 4-quinazolyl group, a 1,10-phenanthroline-5-yl group, a 2-dibenzothienyl group, a 4-dibenzothienyl group, a 2-dibenzofuranyl group, or a 4-dibenzofuranyl group is particularly preferred.

[0072] L ２ L 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, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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. Each group may have substituents, and preferred substituents are methyl groups, cyano groups, fluoro groups, or trifluoromethyl groups.

[0073] R 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and / or linking groups. １１ ~R １６ From the standpoint of synthesis and device performance, R １１ and R １２However, each is preferably independently a hydrogen atom or a phenyl group, R １１ , R １２ , R １３ , R １４ and R １６ is a hydrogen atom, R １５ It is also 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.

[0074] Y ２ Y represents one of the following equations (a) to (h). ２ From the viewpoint of raw material availability, (a), (e), (f), (g), or (h) are preferred, (a), (e), (f), or (h) are more preferred, and (a) is particularly preferred.

[0075] (Acid anhydride derivatives) The present invention relates to an acid anhydride derivative represented by the following formula (5). In formula (5), R ２１ ~R ２６ 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and / or linking groups.

[0076] The acid anhydride derivative represented by formula (5), like the compound having the structure represented by formula (1), has an acid anhydride structure containing a fluorene ring. This strong acceptor skeleton is expected to facilitate strong interaction with the HOMO orbitals of hole transport materials. In other words, by containing the above compound in a layer (e.g., a hole transport-promoting layer) in an organic electronic device (e.g., a photoelectric conversion device), the interaction with the HOMO orbitals of the adjacent hole transport layer is enhanced, and carrier transfer between the hole transport layer and the hole transport-promoting layer is expected to be promoted. Thus, because the above compound has an extremely deep LUMO level, it is expected that the exchange of holes between the hole transport layer and the electrode will be smoother. Because the above compound has an acid anhydride structure containing a fluorene ring, thermal stability and high reduction resistance can also be expected.

[0077] Furthermore, the acid anhydride derivative represented by formula (5) is suitably used as an intermediate for producing compounds having the structure represented by formula (1). It is also useful as an electronic material, a heat-resistant resin, a pharmaceutical or agricultural chemical intermediate, and the like.

[0078] In formula (5), R ２１ ~R ２６ From the perspective of raw material availability, R ２１ and R ２２ However, each is preferably independently a hydrogen atom or a phenyl group, R ２１ , R ２２ , R ２３ , R ２４ and R ２６ is a hydrogen atom, R ２５ It is also 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.

[0079] Preferred examples of acid anhydride derivatives represented by formula (4) include, for example, (B1) to (B15) below. However, acid anhydride derivatives are not limited to these.

[0080]

[0081] Of the above, (B1) to (B7), (B14), and (B15) are even more preferable in order to enhance interaction with adjacent layers such as hole transport layers. Furthermore, from the viewpoint of usefulness as a manufacturing intermediate, (B1), (B2), (B5), (B6), (B7), and (B14) are particularly preferable.

[0082] (Method for producing acid anhydride derivatives) The present invention relates to a method for producing acid anhydride derivatives by reacting a biphenyl derivative represented by the following general formula (6) in the presence of an acid catalyst to perform ring closure. In formula (6), R ２１ ~R ２６ 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, a monocyclic, linking, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monocyclic, linking, or fused heteroaromatic group having 3 to 20 carbon atoms, and the aromatic hydrocarbon group and the heteroaromatic group may have substituents. ３１ ~R ３３ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

[0083] In formula (6), R ２１ ~R ２６ From the viewpoint of raw material availability, it is preferable that each of them independently be a hydrogen atom, a methoxy group, a cyano group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, a phenyl group, and a pyridyl group, R ２１ and R ２２ It is more preferably a hydrogen atom or a phenyl group, R ２３ ~R ２６ More preferably, the group is a hydrogen atom, a methoxy group, a trifluoromethyl group, a fluoro group, a chloro group, a bromo group, or a phenyl group. ３１ ~R ３３ From the viewpoint of reaction yield, each is preferably a hydrogen atom and an alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom or a methyl group.

[0084] Preferred acid catalysts include Lewis acids such as boron trifluoride, boron trifluoride ether complex, boron tribromide, boron trichloride, aluminum chloride, aluminum bromide, iron(III) chloride, iron(III) bromide, antimony trichloride, antimony pentachloride, titanium trichloride, titanium tetrachloride, zinc chloride, and various zeolites, as well as Brønsted acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, polyphosphate, and trifluoromethanesulfonic acid, with polyphosphate being more preferred. The amount of acid catalyst is preferably in the range of 0.1 to 100 times the molar amount relative to the biphenyl derivative, and more preferably in the range of 0.1 to 10 times the molar amount.

[0085] There are no particular restrictions on the reaction temperature, but 50 to 200°C is preferred for efficiently obtaining acid anhydride derivatives. The solvent used in the reaction is not particularly restricted as long as it does not inhibit the reaction. In fact, no solvent may be used at all.

[0086] <Embodiments> Examples of the stacked configuration of the organic electronic element (for example, a photoelectric conversion element) of the present invention include the following configurations (i) or (ii): (i): First electrode / hole transport promoting layer / hole transport layer / light receiving layer / second electrode (ii): 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) or (ii), the "light receiving layer" can be read as the "light emitting layer".

[0087] 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 (ii) 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 the organic EL element according to the present invention.

[0088] <<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.

[0089] 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.

[0090] [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.

[0091] 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.

[0092] 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.

[0093] [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 contains the compound represented by formula (1) described above. It is also possible to include compounds other than the compound represented by formula (1). Examples of compounds that can be included 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.

[0094] [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.

[0095] 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.

[0096] [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.

[0097] 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).

[0098] 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.

[0099] (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). Other acceptor materials include non-fullerene derivatives (ITIC compounds, etc.). (iii) Preferred compounds and specific examples of hole transport materials are the same as those used in the hole transport layer 13 described above.

[0100] 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).

[0101] [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.

[0102] Furthermore, the electron transport material that can be contained in the electron transport layer 15 may be a known electron transport material, and examples of electron transport materials 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), Bp Examples include hen(4,7-diphenyl-1,10-phenanthroline), BAlq(bis(2-methyl-8-quinolinolate)-4-(phenylphenolate)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.

[0103] 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.

[0104] [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 ３Examples 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.

[0105] [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.

[0106] 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.

[0107] 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.

[0108] 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 light passes through the second electrode 16 and enters the light-receiving layer 14, resulting in a photoelectric conversion element.

[0109] The image sensor equipped with the photoelectric conversion element of this embodiment can be applied, for example, to the image sensors of digital cameras and digital video cameras, and to the 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.

[0110] <<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.

[0111] [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).

[0112] [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.

[0113] [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.

[0114] [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.

[0115] [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.

[0116] [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.

[0117] 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 light passes through the second electrode 16 and enters the light-receiving layer 14, resulting in a photoelectric conversion element.

[0118] [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.

[0119] <<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.

[0120] [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.

[0121] 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.

[0122] [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 a compound represented by formula (1) above as a hole injection material (e.g., p-dopant). 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.

[0123] [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.

[0124] [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.

[0125] [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 layer 25 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. 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.

[0126] [Electron injection layer 26'] An electron injection layer 26' may be provided between the electron transport layer 25 and the second electrode 26, which will be described later. The electron injection layer has the function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0127] Examples of materials for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluolenylidenemethane, anthraquinodimethane, anthrone, and Liq(8-hydroxyquinolinolatolithium). Furthermore, SiO ２ , AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, Li, Na, Ca, Mg, CsF, CaCO ３ Other examples include various oxides such as C and Yb, as well as inorganic compounds such as fluorides, nitrides, and oxidized nitrides.

[0128] [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.

[0129] [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.

[0130] The organic electronic elements (photoelectric conversion elements, organic EL elements, etc.) of the present invention, and the methods for forming each layer of said 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.

[0131] 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. １ The 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. For mass spectrometry, an ESI-Qq-TOF MS compact (manufactured by BRUKER) was used.

[0132]

[0133] (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).

[0134] (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).

[0135] (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).

[0136] (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).

[0137] (Synthesis Example 1: Synthesis of Compound (B1)) 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).

[0138] (Synthesis Example 2: Synthesis of Compound (B6)) 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 (B6) (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).

[0139] (Synthesis Example 3: Synthesis of Compound (A2)) Under a nitrogen atmosphere, 1.3 g (5.2 mmol) of the compound (B1) obtained in Synthesis Example 1, 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, 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 (precursor of A2) (1.4 g, yield 78%). １ H-NMR (DMSO-d ６ ) 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

[0140] Next, 1.4 g (4.0 mmol) of the obtained compound (precursor of A2), 0.40 g (6.0 mmol) of malononitrile, and 40 mL of dimethyl sulfoxide were added, and the mixture was stirred at 130°C for 12 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 (A2) (1.2 g, yield 75%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.65 (d, 2H), 8.35 (d, 1H), 8.28 (d, 1H), 8.06 (d, 2H), 7.79-7.73 (m, 3H), 7.64 (ddd, 1H). Mass spectrometry (QTOF-MS): 398

[0141] (Synthesis Example 4: Synthesis of Compound (A7)) The same procedure as in Synthesis Example 3 was followed, 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 (precursor of A7) (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).

[0142] Next, using 0.56 g (1.5 mmol) of the obtained compound (precursor of A7), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A7) (0.33 g, yield 52%). Mass spectrometry (QTOF-MS): 423

[0143] (Synthesis Example 5: Synthesis of Compound (A8)) The same procedure as in Synthesis Example 3 was followed, 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 (precursor of A8) (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

[0144] Next, using 1.7 g (4.0 mmol) of the obtained compound (precursor of A8), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A8) (1.2 g, yield 65%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.70 (s, 1H), 8.67 (s, 1H), 8.47 (d, 1H), 8.36 (d, 1H), 8.36 (d, 1H), 8.22 (s, 1H), 8.09 (dd, 1H), 7.79 (ddd, 1H), 7.66 (ddd, 1H). Mass spectrometry (QTOF-MS): 466

[0145] (Synthesis Example 6: Synthesis of Compound (A16)) The same procedure as in Synthesis Example 3 was followed, 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 (precursor of A16) (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).

[0146] Next, using 1.5 g (3.5 mmol) of the obtained compound (precursor of A16), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A16) (1.1 g, yield 66%). 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).

[0147] (Synthesis Example 7: Synthesis of Compound (A18)) The procedure was the same as in Synthesis Example 3, except that 1.4 g (6.2 mmol) of 2-amino-[1,1'-biphenyl]-4,4'-dicarbonitride was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (precursor of A18) (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).

[0148] Next, using 1.6 g (3.5 mmol) of the obtained compound (precursor of A18), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A18) (1.3 g, yield 75%). １ H-NMR (CDCl ３ ) δ (ppm): 8.82 (s, 1H), 8.51 (d, 1H), 8.01 (s, 1H), 7.90 (dd, 1H), 7.75-7.73 (m, 2H), 7.68-7.61 (m, 4H), 7.53 (ddd, 1H), 7.38 (d, 2H).

[0149] (Synthesis Example 8: Synthesis of Compound (A28)) The procedure was the same as in Synthesis Example 3, 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 (precursor of A28) (1.4 g, yield 55%). Mass spectrometry (QTOF-MS): 477

[0150] Next, using 1.2 g (2.5 mmol) of the obtained compound (precursor of A28), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A28) (0.81 g, yield 62%). Mass spectrometry (QTOF-MS): 525

[0151] (Synthesis Example 9: Synthesis of Compound (A32)) Under a nitrogen atmosphere, 1.3 g (5.2 mmol) of the compound (B1) obtained in Synthesis Example 1, 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 collected by filtration and washed with ethanol. Next, the obtained solid was recrystallized with dimethylformamide / toluene to obtain the target compound (precursor of A32) (1.4 g, yield 50%). Mass spectrometry (QTOF-MS): 527

[0152] Next, 1.2 g (2.3 mmol) of the obtained compound (precursor of A32), 0.23 g (3.5 mmol) of malononitrile, and 20 mL of dimethyl sulfoxide were added, and the mixture was stirred at 130°C for 12 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 (A32) (0.79 g, yield 60%). Mass spectrometry (QTOF-MS): 575

[0153] (Synthesis Example 10: Synthesis of Compound (A39)) The same procedure as in Synthesis Example 9 was followed, 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 (precursor of A39) (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)

[0154] Next, using 0.70 g (2.0 mmol) of the obtained compound (precursor of A39), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A39) (0.54 g, yield 67%). １ H-NMR (CDCl ３ ) δ (ppm): 8.98 (s, 1H), 8.86 (d, 1H), 8.55 (d, 1H), 8.20-8.18 (m, 2H), 7.99 (dd, 1H), 7.82 (d, 1H), 7.20 (ddd, 1H), 7.56 (ddd, 1H).

[0155] (Synthesis Example 11: Synthesis of Compound (A41)) The procedure was the same as in Synthesis Example 9, 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 (precursor of A41) (1.1 g, yield 59%). １H-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).

[0156] Next, using 1.1 g (3.1 mmol) of the obtained compound (precursor of A41), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A41) (0.72 g, yield 58%). Mass spectrometry (QTOF-MS): 399

[0157] (Synthesis Example 12: Synthesis of Compound (A57)) The procedure was the same as in Synthesis Example 9, 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 (precursor of A57) (1.4 g, yield 70%). Mass spectrometry (QTOF-MS): 376

[0158] Next, using 1.3 g (3.5 mmol) of the obtained compound (precursor of A57), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A57) (0.82 g, yield 55%). Mass spectrometry (QTOF-MS): 424

[0159] (Synthesis Example 13: Synthesis of Compound (A65)) The procedure was the same as in Synthesis Example 9, 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 (precursor of A65) (1.7 g, yield 68%). Mass spectrometry (QTOF-MS): 478

[0160] Next, using 1.7 g (3.5 mmol) of the obtained compound (precursor of A65), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A65) (0.59 g, yield 32%). Mass spectrometry (QTOF-MS): 526

[0161] (Synthesis Example 14: Synthesis of Compound (A68)) The same procedure as in Synthesis Example 3 was followed, except that 0.91 g (6.2 mmol) of 2-amino-1-methyl-1H-imidazole-4,5-dicarbonitrile was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (precursor of A68) (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).

[0162] Next, using 0.65 g (1.7 mmol) of the obtained compound (precursor of A68), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A68) (0.36 g, yield 50%). Mass spectrometry (QTOF-MS): 427

[0163] (Synthesis Example 15: Synthesis of Compound (A78)) The same procedure as in Synthesis Example 3 was followed, except that 0.78 g (6.2 mmol) of 2-amino-4-cyanothiazole was used instead of 0.74 g (6.2 mmol) of 4-aminobenzonitrile to obtain the target compound (precursor of A78) (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).

[0164] Next, using 1.2 g (3.3 mmol) of the obtained compound (precursor of A78), the same procedure as in Synthesis Example 3 was carried out to obtain the target compound (A78) (0.83 g, yield 62%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.85 (s, 1H), 8.70 (s, 1H), 8.65 (s, 1H), 8.35 (d, 1H), 8.30 (d, 1H), 7.78 (ddd, 1H), 7.65 (ddd, 1H).

[0165] (Synthesis Example 16: Synthesis of Compound (A97)) The procedure was the same as in Synthesis Example 9, 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 (precursor of A97) (0.77 g, yield 43%). Mass spectrometry (QTOF-MS): 288

[0166] Next, using 0.35 g (1.2 mmol) of the obtained compound (precursor of A97), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A97) (0.10 g, yield 24%). Mass spectrometry (QTOF-MS): 336

[0167] (Synthesis Example 17: Synthesis of Compound (A107)) The same procedure as in Synthesis Example 9 was followed, 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 (precursor of A107) (0.60 g, yield 24%). Mass spectrometry (QTOF-MS): 479

[0168] Next, using 0.58 g (1.2 mmol) of the obtained compound (precursor of A107), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A107) (0.39 g, yield 62%). Mass spectrometry (QTOF-MS): 527

[0169] (Synthesis Example 18: Synthesis of Compound (A121)) The procedure was the same as in Synthesis Example 9, 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 (precursor of A121) (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).

[0170] Next, using 0.98 g (2.3 mmol) of the obtained compound (precursor of A121), the same procedure as in Synthesis Example 9 was carried out to obtain the target compound (A121) (0.84 g, yield 77%). Mass spectrometry (QTOF-MS): 475

[0171] (Synthesis Example 19: Synthesis of Compound (B2)) Under a nitrogen atmosphere, 5.0 g (28.1 mmol) of ninhydrin, 6.5 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 (precursor of B2) (5.7 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).

[0172] Next, 0.50 g (1.5 mmol) of the obtained compound (precursor of B2) was mixed with 1.0 g (9.0 mmol) of acetylenedicarboxylic acid and 5 mL of xylene, and the mixture was stirred at 140°C for 18 hours. After cooling to room temperature, the precipitated solid was filtered and washed with hexane. Then, the obtained solid was stirred with 10 mL of xylene, cooled to room temperature, and filtered to obtain the target compound (B2) (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).

[0173] (Evaluation Example 1: Film Quality Evaluation of Compound (A16)) A Si substrate (with native oxide film) was introduced into a vacuum deposition chamber, and 1.0 × 10 －４ The pressure was reduced to Pa. Then, a 30 nm film of the sublimation-purified compound (A16) 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 0.20 nm.

[0174] (Evaluation Example 2: Film Quality Evaluation of Compound (B2)) The measurement was performed in the same manner as in Evaluation Example 1, except that compound (B2) was used instead of compound (A16). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.88 nm.

[0175] (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 (A16). 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 used after sublimation purification.

[0176] (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 (A16). 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.

[0177] (Evaluation Comparative Example 2: Film Quality Evaluation of Compound (D2)) The measurement was performed in the same manner as in Evaluation Example 1, except that compound (D2) was used instead of compound (A16). The arithmetic mean roughness (Ra) in the surface roughness measurement was 8.78 nm. Compound (D2) was synthesized according to the method described below and purified by sublimation.

[0178] Under a nitrogen atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.34 g, 5.0 mmol), 4-fluoroaniline (1.17 g, 10.5 mmol), isoquinoline (0.56 g, 4.3 mmol), and 20 mL of m-cresol were added to a 100 mL three-necked flask and stirred at 150 °C for 12 hours. After cooling to room temperature, the precipitated solid was filtered and washed with ethanol. Next, the obtained solid was recrystallized with dimethylformamide to obtain the target compound (D2) (1.02 g, yield 45%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.73 (s, 4H), 7.55-7.38 (m, 8H).

[0179]

[0180] Based on the above film quality evaluation, it was confirmed that the films prepared using compound (A16) from Evaluation Example 1 and compound (B2) from Evaluation Example 2 exhibited even higher film smoothness than the films prepared using compound (C1) from Evaluation Comparative Example 1, compound (D1) from Evaluation Reference Example 1, and compound (D2) from Evaluation Comparative Example 2.

[0181] <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.

[0182] [Compounds used for evaluation]

[0183] (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 －５The pressure was reduced to Pa. Then, each layer was fabricated in the following order according to the deposition conditions for each layer. (Fabrication of electron transport layer 15) The electron transport layer 15 was fabricated by depositing a 10 nm film of the sublimation-purified compound 4,6-bis(3,5-di(pyridine-4-yl)phenyl)-2-methylpyrimidine at a rate of 0.03 nm / second. (Fabrication of light-receiving layer 14) The photoelectric conversion layer 14 was fabricated by depositing a 250 nm film of N,N-dimethylquinacridone and fullerene C60 in a ratio of 4:1 (mass ratio). The deposition rate was 0.13 nm / second. (Fabrication of hole transport layer 13) The hole transport layer 13 was fabricated by depositing a 10 nm film of (HTL-1) as the hole transport material at a rate of 0.10 nm / second. (Fabrication of hole transport-promoting layer 12) Compound (A8) was deposited at a rate of 0.20 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 80 nm of Au. The deposition rate of Au was 0.1 nm / second.

[0184] Therefore, the area is 4 mm². ２ A 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.

[0185] 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 (100). A lower dark current value indicates better performance, while a higher external quantum efficiency value indicates better performance.

[0186] [Device Example 2] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A16) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0187] [Device Example 3] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (A18) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0188] [Element Example 4] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A28) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0189] [Element Example 5] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A39) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0190] [Element Example 6] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A68) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0191] [Element Example 7] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A78) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0192] [Element Example 8] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A97) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0193] [Element Example 9] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A107) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0194] [Element Example 10] A photoelectric conversion element was fabricated in the same manner as in Element Example 1, except that compound (A121) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0195] [Device Example 11] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (B2) was used instead of compound (A8) in the fabrication of the hole transport promoting layer 12. 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.

[0196] [Device Comparative Example 1] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (C1) was used instead of compound (A8) in the fabrication of the hole transport-promoting layer 12. 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. [Device Reference Example 1] A photoelectric conversion device was fabricated in the same manner as in Device Example 1, except that compound (D1) was used instead of compound (A8) in the fabrication of the hole transport-promoting layer 12. 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.

[0197]

[0198] As shown in Table 2, the elements of Examples 1 to 11 using the material for photoelectric conversion elements for image sensors of the present invention showed suppressed dark current and high external quantum efficiency compared to Comparative Example 1.

[0199] The organic electronic element of the present invention, by containing the compound represented by formula (1) above, can improve the hole 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.

[0200] <Fabrication and Evaluation of Organic EL Elements> [Element Example 12] An organic EL element 2 having a laminated structure consisting of a substrate, a first electrode 21, a hole injection layer 22, a hole transport layer 23-1, a hole transport layer 23-2, a light-emitting layer 24, an electron transport layer 25-1, an electron transport layer 25-2, an electron injection layer 26', and a second electrode 26 was fabricated. The voltage and power efficiency of the organic EL element were measured, and the element lifespan during continuous lighting was measured.

[0201] [Compounds used for evaluation]

[0202] (Preparation of the substrate and the first electrode 21) A glass substrate with a transparent ITO electrode was prepared, on which a 2 mm wide indium-tin (ITO) film (thickness 110 nm) was patterned in stripes, with the first electrode mounted on its surface. Next, this substrate was ultrasonically cleaned with ultrapure water, and then surface-treated by ozone ultraviolet cleaning.

[0203] (Preparation for vacuum deposition) After cleaning and surface treatment, each layer was deposited by vacuum deposition on the substrate using the vacuum deposition method to form a laminated structure. First, the glass substrate was introduced into the vacuum deposition tank, and 1.0 × 10 －４The pressure was reduced to Pa. Then, each layer was fabricated according to the deposition conditions for each layer in the following order. Each organic material was deposited using the resistance heating method.

[0204] (Fabrication of hole injection layer 22) A hole injection layer 22 was fabricated by depositing HTL-2 and compound (A2) in a ratio of 90:10 (mass ratio) to a thickness of 10 nm. The deposition rate was 0.1 nm / second.

[0205] (Fabrication of hole transport layer 23-1) Hole transport layer 23-1 was fabricated by depositing HTL-2 at a rate of 0.2 nm / second to a thickness of 85 nm.

[0206] (Fabrication of hole transport layer 23-2) A hole transport layer 23-2 was fabricated by depositing HTL-3 at a rate of 0.15 nm / second to a thickness of 5 nm. This hole transport layer also functions as an electron blocking layer that prevents the inflow of electrons.

[0207] (Fabrication of the light-emitting layer 24) A light-emitting layer 24 was fabricated by depositing BH and BD in a ratio of 97:3 (mass ratio) to a thickness of 20 nm. The deposition rate was 0.1 nm / second.

[0208] (Fabrication of electron transport layer 25-1) ETL-1 was deposited at a rate of 0.05 nm / second to a thickness of 6 nm to fabricate electron transport layer 25-1. This electron transport layer also functions as a hole blocking layer that prevents the inflow of holes.

[0209] (Fabrication of electron transport layer 25-2) ETL-2 and 8-hydroxyquinolinolatrium were deposited in a 50:50 (mass ratio) layer at a thickness of 25 nm to fabricate electron transport layer 25-2. The deposition rate was 0.15 nm / second.

[0210] (Fabrication of electron injection layer 26') Yb was deposited at a rate of 0.02 nm / second to a thickness of 1 nm to fabricate the electron injection layer 26'.

[0211] (Fabrication of the second electrode 26) Finally, a metal mask was placed perpendicular to the ITO stripe on the substrate, and the second electrode was deposited. The cathode was made of silver / magnesium (mass ratio 10 / 1) and silver, deposited in that order at 80 nm and 20 nm, respectively, to form a two-layer structure. The deposition rate of silver / magnesium was 0.2 nm / second, and the deposition rate of silver was 0.2 nm / second.

[0212] As a result, the light-emitting area is 4 mm² as shown in Figure 2. ２ Organic electroluminescent devices were fabricated. The film thickness of each device was measured using a stylus-type film thickness analyzer (DEKTAK, Bruker).

[0213] Furthermore, this element was sealed in a nitrogen atmosphere glove box with an oxygen and moisture concentration of 1 ppm or less. The sealing was performed using a Moresco Moisture Cut (manufactured by Moresco) to seal the glass sealing cap and the film-deposited substrate (element).

[0214] A direct current was applied to the organic EL element fabricated as described above, and its luminescence characteristics were evaluated using the luminance meter of a spectroradiometer (SR-3) manufactured by TOPCON Corporation.

[0215] As for the luminescence characteristics, the current density is 10 mA / cm². ２ The voltage (V) and power efficiency (lm / A) were measured when the current was applied, and the element lifespan during continuous operation was measured. The element lifespan was determined by an initial brightness of 1000 cd / m². ２ The brightness decay time during continuous lighting when driven by was measured, and the brightness (cd / m²) was measured. ２ The time required for the voltage to decrease by 5% was measured. The values ​​for voltage, power efficiency, and lifespan are expressed as relative values ​​with the value of comparative example 2 set to 100. The results are shown in Table 3. The measurements were performed in an atmosphere of 23°C and 50% RH. A smaller voltage value indicates better performance, while a larger efficiency and lifespan value indicates better performance, respectively.

[0216] [Element Example 13] An organic EL element was fabricated in the same manner as in Element Example 12, except that compound (A7) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and element lifetime were measured in the same manner as in Element Example 12. The results are shown in Table 3.

[0217] [Element Example 14] An organic EL element was fabricated in the same manner as in Element Example 12, except that compound (A8) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and element lifetime were measured in the same manner as in Element Example 12. The results are shown in Table 3.

[0218] [Element Example 15] An organic EL element was fabricated in the same manner as in Element Example 12, except that compound (A18) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and element lifetime were measured in the same manner as in Element Example 12. The results are shown in Table 3.

[0219] [Element Example 16] An organic EL element was fabricated in the same manner as in Element Example 12, except that compound (A32) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and element lifetime were measured in the same manner as in Element Example 12. The results are shown in Table 3.

[0220] [Element Example 17] An organic EL element was fabricated in the same manner as in Element Example 12, except that compound (A121) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and element lifetime were measured in the same manner as in Element Example 12. The results are shown in Table 3.

[0221] [Device Comparative Example 2] An organic EL device was fabricated in the same manner as in Device Example 12, except that compound (D1) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and device lifetime were measured in the same manner as in Device Example 12. The results are shown in Table 3.

[0222] [Device Comparative Example 3] An organic EL device was fabricated in the same manner as in Device Example 12, except that compound (D2) was used instead of compound (A2) in the fabrication of the hole injection layer 22. Voltage, power efficiency, and device lifetime were measured in the same manner as in Device Example 12. The results are shown in Table 3.

[0223]

[0224] As shown in Table 3, in the devices of Examples 12 to 17 using the organic EL device material of the present invention, it was confirmed that the voltage, power efficiency, and device lifespan were all improved compared to Comparative Examples 2 and 3.

[0225] The organic electronic element of the present invention, by containing the compound represented by formula (1) above, can improve the hole injection capability and further promote the hole transport capability. Furthermore, when used in an organic EL element, the organic electronic element of the present invention can provide a more efficient light-emitting element.

[0226] <Fabrication and Evaluation of Photoelectric Conversion Element> [Element Example 18] 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, external quantum efficiency, and response time of the photoelectric conversion element were evaluated.

[0227] [Compounds used for evaluation]

[0228] (Preparation of the substrate and the second electrode 16) A glass substrate with a transparent ITO electrode was prepared, on which a 2 mm wide indium-tin (ITO) film (thickness 110 nm) was patterned in stripes, with the second electrode mounted on its surface. Next, this substrate was cleaned with isopropyl alcohol and then surface-treated by ozone ultraviolet cleaning.

[0229] (Preparation for vacuum deposition) After cleaning and surface treatment, each layer was deposited using the vacuum deposition method on the substrate to form a laminated structure. 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 deposition conditions for each layer, in the following order.

[0230] (Fabrication of electron transport layer 15) Compound (A18) was deposited at a rate of 0.03 nm / second to a thickness of 10 nm to fabricate the electron transport layer 15.

[0231] (Fabrication of the light-receiving layer 14) 2Ph-BTBT, F6-SubPc-OC6F5, and fullerene (C60) were co-deposited at a deposition rate ratio of 4:4:2 to a thickness of 200 nm. The deposition rate was 0.15 nm / second.

[0232] (Fabrication of hole transport layer 13) A hole transport layer 13 was fabricated by depositing a 10 nm film of the hole transport material (HTL-1 used in Element Example 1) at a speed of 0.10 nm / second.

[0233] (Preparation of hole transport-promoting layer 12) A hole transport-promoting layer 12 was prepared by depositing a compound (HAT-CN) at a rate of 0.20 nm / second to a thickness of 10 nm.

[0234] (Fabrication of the 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 deposited with 80 nm of Au. The deposition rate of Au was 0.1 nm / second.

[0235] Therefore, the area is 4 mm². ２ A 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 50 μW / cm². ２ The measurement was performed using [this method].

[0236] The response time was measured at a wavelength of 560 nm and an intensity of 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.

[0237] The results are shown in Table 4. Note that the dark current, external quantum efficiency, and response time are relative values, with the results from Comparative Example 4 (described later) set as the baseline (100). Lower values ​​for dark current and response time indicate better performance, while higher values ​​for external quantum efficiency indicate better performance.

[0238] [Device Example 19] A photoelectric conversion device was fabricated in the same manner as in Device Example 18, except that compound (A57) was used instead of compound (A18) in the fabrication of the electron transport layer 15. The dark current, external quantum efficiency, and response time were measured in the same manner as in Device Example 18. The results are shown in Table 4.

[0239] [Device Comparative Example 4] The photoelectric conversion device of Device Comparative Example 1 was fabricated in the same manner as Device Example 18, except that compound (E1) was used instead of compound (A18) in the fabrication of the electron transport layer 15. The dark current, external quantum efficiency, and response time were measured in the same manner as in Device Example 18. The results are shown in Table 4. Compound (E1) was synthesized by the method described in Journal of the American Chemical Society (2011), 133(39), 15256-15259, and then purified by sublimation.

[0240]

[0241] As shown in Table 4, the elements of Element Example 18 and Element Example 19, which use the material for photoelectric conversion elements for image sensors of the present invention, exhibited suppressed dark current, higher external quantum efficiency, and faster response time compared to Element Comparative Example 4.

[0242] The photoelectric conversion element of the present invention, by containing a compound having a deep LUMO level represented by formula (1) above, not only promotes carrier transfer between the hole transport layer and the hole transport enhancement layer, but also improves the electron transport capability, enabling more efficient photoelectric conversion when used as an electron transport layer in a photoelectric conversion element. Furthermore, by containing the compound represented by formula (1) above, the dark current of the photoelectric conversion element of the present invention is suppressed, and it is expected that noise will be reduced when used as a photoelectric conversion element such as an image sensor. Moreover, by containing the compound represented by formula (1) above, the photoelectric conversion element of the present invention can have a high external quantum efficiency and can convert light into current without loss, so high sensitivity can be expected as a photoelectric conversion element.

[0243] 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 contains a compound having a substructure represented by the following formula (1). (In formula (1), X １ and X ２ Each of these groups bonds with a divalent group represented by formula (2) or (3) below, where * represents a bond. 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. n represents an integer from 0 to 2. L 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 an (n+1) valency heteroaromatic group having 3 to 20 carbon atoms, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups. １ (This represents either an oxygen atom or one of the following formulas (a) to (h).) 2. The R a , the L １ , and the R １ to R ６ In the case where the organic electronic device according to claim 1 may have the substituent, the substituent may be 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, an 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, or a heteroaromatic group having 3 to 20 carbon atoms.

3. An organic electronic element comprising a first electrode, a second electrode, and an organic layer and a light-receiving layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a substructure represented by formula (1).

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

5. 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 a hole transport layer and a hole transport promoting layer containing a compound having a substructure represented by formula (1), or a layer obtained by mixing a hole transport material and a compound having a substructure represented by formula (1), according to claim 1.

6. The organic electronic element according to claim 5, wherein the hole transport layer and the hole transport enhancement layer are arranged adjacent to each other between the first electrode and the second electrode.

7. The organic electronic element according to claim 1, wherein formula (1) is the following formula (1a) or (1b). (In formula (1a) or (1b), 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. n represents an integer from 0 to 2. L 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 an (n+1) valency heteroaromatic group having 3 to 20 carbon atoms, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and linking groups. １ (This represents one of the above formulas (a) to (h).) 8. In formula (1a) or (1b), R １ and R ２ The organic electronic element according to claim 7, wherein each is independently a hydrogen atom or a phenyl group.

9. In formula (1a) or (1b), R １ , R ２ , R ３ , R ４ and R ６ is a hydrogen atom, R ５ The organic electronic element according to claim 7, 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.

10. In the above formula (1a), Y １ The organic electronic element according to any one of claims 1 to 9, wherein is the formula (a) above.

11. An imide compound represented by the following formula (4). (In formula (4), 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, wherein the alkyl group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. n represents an integer from 0 to 2.) L 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 an (n+1) valency heteroaromatic group having 3 to 20 carbon atoms, and the aliphatic hydrocarbon group, the aromatic hydrocarbon group, and the heteroaromatic group may have substituents. 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, wherein the aromatic hydrocarbon group and the heteroaromatic group may have one or more substituents and / or linking groups. ２ This represents one of the following equations (a) to (h).

12. In formula (4) above, R ｂ , said L ２ , and the R １１ ~R １６ The imide compound according to claim 11, wherein the substituents that may be present are 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, an 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, or a heteroaromatic group having 3 to 20 carbon atoms.

13. In formula (4) above, R ｂ The imide compound according to claim 11, 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 each group may have a substituent.

14. L ２ The imide compound according to claim 11, 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 each group may have substituents.

15. In formula (4) above, R １１ and R １２ The imide compound according to claim 11, wherein each is independently a hydrogen atom or a phenyl group.

16. In formula (4) above, R １１ , R １２ , R １３ , R １４ and R １６ is a hydrogen atom, R １５ The imide compound according to claim 11, 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.

17. In the above formula (4), Y ２ The imide compound according to any one of claims 11 to 16, wherein is the formula (a).

18. An acid anhydride derivative represented by the following formula (5). (In formula (5), R ２１ to R ２６ each 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, and the aromatic hydrocarbon group and the heteroaromatic group may each have one or more of a substituent and a linking group.) 19. In the above formula (5), R ２１ and R ２２ The acid anhydride derivative according to claim 18, wherein each is independently a hydrogen atom or a phenyl group.

20. In formula (5), R ２１ , R ２２ , R ２３ , R ２４ and R ２６ is a hydrogen atom, R ２５ The acid anhydride derivative according to claim 18, 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.

21. A method for producing an acid anhydride derivative according to claim 18, comprising reacting a biphenyl derivative represented by the following general formula (6) in the presence of an acid catalyst to cause ring closure. (In formula (6), R ２１ ~R ２６ 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, a monocyclic, linking, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monocyclic, linking, or fused heteroaromatic group having 3 to 20 carbon atoms, and the aromatic hydrocarbon group and the heteroaromatic group may have substituents. ３１ ~R ３３ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

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