Organic electronic element, material for organic electronic element, and imide compound

Abstract

The present invention provides an organic electronic element and an imide compound, with which hole transport capability can be improved.　Provided is 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 represented by formula (1). (In formula (1): Ar1 is a C6-30 aromatic hydrocarbon group which may be substituted with R11, a C3-30 heteroaromatic group which may be substituted with R11, or a C1-30 unsubstituted alkyl group which may have a branched or cyclic structure, and R1 is a C1-15 aliphatic hydrocarbon group; n represents 1, 2, or 3; and R11 and ring A are prescribed groups.)

Description

Organic electronic devices, materials for organic electronic devices, and imide compounds

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

[0002] Currently, there are active efforts to create new high-performance devices using organic compounds. In particular, research and development on organic electronic elements such as photoelectric converters and organic EL elements is thriving, and material and device designs aimed at improving the performance of these devices are progressing. For example, photoelectric converters used for video recording require a high speed at which carriers (electrons and holes) generated in the light-receiving layer are transported to the electrodes in order to suppress the cause of afterimages. Similarly, organic EL elements require a high speed at which carriers are transported from the electrodes to the light-emitting layer in order to reduce the 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, a hole transport-promoting material, and an imide compound that can improve the hole transport capability.

[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 represented by the following formula (1). (In formula (1), Ar １ R１１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R １１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. １ Y represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group is one or more groups selected from hydroxyl group, carboxyl group, formyl group, nitro group, fluoro group, chloro group, bromo group, iodine group, trifluoromethyl group, cyano group, carbon-oxygen double bond, carbon-sulfur double bond, aromatic hydrocarbon group having 6 to 20 carbon atoms, heteroaromatic group having 3 to 20 carbon atoms, and aliphatic hydrocarbon group having 1 to 15 carbon atoms. １ The aliphatic hydrocarbon group may be substituted with a , and the aliphatic hydrocarbon group may be linear, branched, or cyclic, where n represents 1, 2, or 3. Ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms, and the aromatic hydrocarbon ring and the heteroaromatic ring may each be monocyclic, fused, or linked, and the linked ring may be bonded by a methylene group substituted with a trifluoromethyl group, and the aromatic hydrocarbon ring and the heteroaromatic ring may be one or more groups Y selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. ２may be replaced, and the aromatic hydrocarbon ring and the heteroaromatic ring may be bonded by one or more selected from the aromatic hydrocarbon group or the heteroaromatic group, an oxygen atom, a carbonyl group, and a thiocarbonyl group. ) [2] An organic electronic device including 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 the compound represented by the formula (1), the organic electronic device according to [1]. [3] The organic electronic device according to [2], wherein the light-receiving layer is a layer containing at least two organic components. [4] The organic layer includes a hole transport layer and a hole transport promoting layer containing the compound represented by the formula (1), or includes a layer formed by mixing a hole transport material and the compound represented by the formula (1), the organic electronic device according to any one of [1] to [3]. [5] The organic electronic device according to [4], 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. [6] R in the formula (1) １ is a methylene group or an ethylene group, and the methylene group and the ethylene group are a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, one or more groups Y １ may be substituted, the organic electronic device according to any one of [1] to [5]. [7] R in the formula (1) １ is an unsubstituted methylene group or an unsubstituted ethylene group, the organic electronic device according to any one of [1] to [5]. [8] Ar in the formula (1) １The organic electronic element according to any one of [1] to [7], wherein the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof. [9] Ar in formula (1) １ The organic electronic element according to any one of [1] to [8], wherein the group is a phenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a fluorophenyl group, a difluorophenyl group, a perfluorophenyl group, a cyanophenyl group, a dicyanophenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, a cyanobiphenyl group, a dicyanobiphenyl group, a pyridylphenyl group, a pyridylbenzonitrile group, a pyridyl group, a cyanopyridyl group, a dicyanopyridyl group, a trifluoromethylpyridyl group, a trifluoromethylpyridyl group, a bistrifluoromethylpyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a cyanophenylpyridyl group, a bipyridyl group, a terpyridyl group, a quinolyl group, a cyanoquinolyl group, a trifluoromethylquinolyl group, an isoquinolyl group, a cyanoisoquinolyl group, a trifluoromethylisoquinolyl group, a phenantrenyl group, anthryl group, a phenantrolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, or a spirofluorenyl group.

[10] Ar in formula (1) １ The organic electronic device according to any one of [1] to [9], wherein the ring A in formula (1) is one or more of the groups Y ２ An organic electronic element according to any of [1] to

[10] , which is any of the following (A-1) to (A-17), which may be substituted with. (In formulas (A-1) to (A-17), Y ２l represents the same substituent as described above. l represents 0, 1 or 2, and p represents 0, 1 or 2, where 0 ≤ l + p ≤ 4.)

[12] A material for organic electronic devices containing a compound represented by the following formula (2). (In formula (2), Ar ２ R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R ２１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. ２ Y represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group is one or more groups selected from hydroxyl group, carboxyl group, formyl group, nitro group, fluoro group, chloro group, bromo group, iodine group, trifluoromethyl group, cyano group, carbon-oxygen double bond, carbon-sulfur double bond, aromatic hydrocarbon group having 6 to 20 carbon atoms, heteroaromatic group having 3 to 20 carbon atoms, and aliphatic hydrocarbon group having 1 to 15 carbon atoms. １The aliphatic hydrocarbon group may be substituted with a , and the aliphatic hydrocarbon group may be linear, branched, or cyclic, where n represents 1, 2, or 3. Ring B represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms, and the aromatic hydrocarbon ring and the heteroaromatic ring may each be monocyclic, fused, or linked, and the linked ring may be bonded by a methylene group substituted with a trifluoromethyl group, and the aromatic hydrocarbon ring and the heteroaromatic ring may be one or more groups Y selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. ２ It may be substituted with, and the aromatic hydrocarbon ring and the heteroaromatic ring may be bonded to the aromatic hydrocarbon group or the heteroaromatic group by one or more selected from an oxygen atom, a carbonyl group and a thiocarbonyl group.)

[13] The organic electronic element material according to

[12] , which is a material for a photoelectric conversion element.

[14] The organic electronic element material according to

[12] or

[13] , which is a material for an imaging photoelectric conversion element.

[15] R in formula (2) ２ However, the methylene group or ethylene group is one or more groups selected from hydroxyl groups, carboxyl groups, formyl groups, nitro groups, fluoro groups, chloro groups, bromo groups, iodo groups, trifluoromethyl groups, cyano groups, carbon-oxygen double bonds, carbon-sulfur double bonds, aromatic hydrocarbon groups having 6 to 20 carbon atoms, heteroaromatic groups having 3 to 20 carbon atoms, and aliphatic hydrocarbon groups having 1 to 15 carbon atoms. １ The organic electronic device material according to any one of

[12] to

[14] , which may be substituted with

[16] R in formula (2) ２ The material for an organic electronic device according to any one of

[12] to

[15] , wherein the Ar in formula (2) is an unsubstituted methylene group or an unsubstituted ethylene group.

[17] ２The material for an organic electronic device according to any one of

[12] to

[16] , wherein the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof.

[18] Ar in formula (2) ２ The material for an organic electronic device according to any one of

[12] to

[17] , wherein the group is a phenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a fluorophenyl group, a difluorophenyl group, a perfluorophenyl group, a cyanophenyl group, a dicyanophenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, a cyanobiphenyl group, a dicyanobiphenyl group, a pyridylphenyl group, a pyridylbenzonitrile group, a pyridyl group, a cyanopyridyl group, a dicyanopyridyl group, a trifluoromethylpyridyl group, a trifluoromethylpyridyl group, a bistrifluoromethylpyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a cyanophenylpyridyl group, a bipyridyl group, a terpyridyl group, a quinolyl group, a cyanoquinolyl group, a trifluoromethylquinolyl group, an isoquinolyl group, a cyanoisoquinolyl group, a trifluoromethylisoquinolyl group, a phenantrenyl group, anthryl group, a phenantrolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, or a spirofluorenyl group.

[19] Ar in formula (2) ２ The material for an organic electronic device according to any one of

[12] to

[18] , wherein the ring B in formula (2) is one or more of the groups Y ２ A material for an organic electronic device according to any of

[12] to

[19] , which may be substituted with any of the following (B-1) to (B-17). (In formulas (B-1) to (B-17), Y２ l represents the same substituent as described above. l represents 0, 1 or 2, and p represents 0, 1 or 2, where 0 ≤ l + p ≤ 4.)

[21] An imide compound represented by the following formula (3) or the following formula (4). (In formula (3), Ar ３ is R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R ３１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. ３ m represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be linear, branched, or cyclic, and m represents 1, 2, or 3. １ and T ２ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. (In formula (4), Ar ４ is R ４１A C6-C30 aromatic hydrocarbon group, which may be substituted with R ４１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R ４１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. ４ m represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be linear, branched, or cyclic, and m represents 1, 2, or 3. ３ , T ４ , T ５ and T ６ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. However, T ３ , T ４ , T ５ and T ６ However, all of them are hydrogen atoms, m=1, and R ４ When it is a methylene group, Ar ４ R in formula (3) above is not an unsubstituted 2-pyridyl group or an unsubstituted 2-pyradyl group.)

[22] ３ Or R in notation (4) ４ However, each is independently a methylene group or an ethylene group, and the methylene group and the ethylene group may be substituted with one or more groups selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, as described in

[21] .

[23] R in formula (3) ３ Or R in formula (4) above ４ The imide compound according to

[21] or

[22] , wherein each is independently an unsubstituted methylene group or an unsubstituted ethylene group.

[24] R in formula (3) ３ Or R in formula (4) above ４ The imide compound according to any one of

[21] to

[23] , wherein each methylene group is independently substituted with a cyano group, a phenyl group, a cyanophenyl group, or a pyridyl group.

[25] Ar in formula (3) ３ or Ar in formula (4) above ４ The imide compound according to any one of

[21] to

[24] , wherein each is independently a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof.

[26] Ar in formula (3) ３ or Ar in formula (4) above ４The imide compound according to any one of

[21] to

[25] , wherein each is independently a phenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a fluorophenyl group, a difluorophenyl group, a perfluorophenyl group, a cyanophenyl group, a dicyanophenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, a cyanobiphenyl group, a dicyanobiphenyl group, a pyridylphenyl group, a pyridylbenzonitrile group, a pyridyl group, a cyanopyridyl group, a dicyanopyridyl group, a trifluoromethylpyridyl group, a bistrifluoromethylpyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a cyanophenylpyridyl group, a bipyridyl group, a terpyridyl group, a quinolyl group, a cyanoquinolyl group, a trifluoromethylquinolyl group, an isoquinolyl group, a cyanoisoquinolyl group, a trifluoromethylisoquinolyl group, a phenantrenyl group, anthryl group, a phenantrolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, or a spirofluorenyl group.

[27] Ar in formula (3) ３ or Ar in formula (4) above ４ However, each independently is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof, as described in any of

[21] to

[26] .

[28] T in formula (3) １ ~T ２ or T in formula (4) above ３ ~T ６ The imide compound according to any one of

[21] to

[27] , wherein the group is a hydrogen atom, a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

[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 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), Ar １ R １１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. １Y represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group is one or more groups selected from hydroxyl group, carboxyl group, formyl group, nitro group, fluoro group, chloro group, bromo group, iodine group, trifluoromethyl group, cyano group, carbon-oxygen double bond, carbon-sulfur double bond, aromatic hydrocarbon group having 6 to 20 carbon atoms, heteroaromatic group having 3 to 20 carbon atoms, and aliphatic hydrocarbon group having 1 to 15 carbon atoms. １ The aliphatic hydrocarbon group may be substituted with a , and the aliphatic hydrocarbon group may be linear, branched, or cyclic. n represents 1, 2, or 3. Ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms, and the aromatic hydrocarbon ring and the heteroaromatic ring may each be monocyclic, fused, or linked rings, and the linked ring may be bonded by methylene groups substituted with trifluoromethyl groups.

[0027] The compound represented by formula (1) is R １ - (CN) ｎ It has an alkylcyano group represented by . Having such an alkylcyano group makes it easier to achieve both high intermolecular interaction and a good amorphous film when used as an organic electronic device material. In particular, by combining an easily rotatable alkyl group with a coordinating cyano group, R １ - (CN) ｎ The cyano group in the alkylcyano group represented by can orient itself in any direction, which tends to strengthen intermolecular interactions with adjacent layers. Such strong intermolecular interactions make the transfer of carriers (electrons or holes) more efficient, making it easier to improve the performance of organic electronic devices.

[0028] Furthermore, the compound represented by formula (1) has Ar at one end with ring A at the center. １ On the other hand, R １ It has a left-right asymmetric substructure containing -(CN)n. Imide compounds with such left-right asymmetric substructures tend to undergo random orientation during vapor deposition, resulting in an amorphous structure. This amorphous nature makes it easier to form films with a lower average surface roughness when used as a vapor deposition material.

[0029] The alkyl cyano group R １ in -(CN)n １ represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. Further, the aliphatic hydrocarbon group may be a group in which a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group are combined. Examples of the saturated aliphatic hydrocarbon group include an alkylene group having 1 to 15 carbon atoms. In the present specification, the "alkylene group" refers to a divalent group formed by losing two hydrogen atoms from an aliphatic hydrocarbon (alkane) such as methane, ethane, or propane, and is generally represented by -C ｘ H ２ｘ -(where x is a positive integer). Examples of the unsaturated aliphatic hydrocarbon group include an alkenylene group having 2 to 15 carbon atoms and an alkynylene group having 2 to 15 carbon atoms. The unsaturated aliphatic hydrocarbon group may have two or more carbon-carbon double bonds, two or more carbon-carbon triple bonds, or both carbon-carbon double bonds and carbon-carbon triple bonds. In the present specification, the "alkenylene group" refers to a divalent group formed by losing two hydrogen atoms from an aliphatic hydrocarbon having one carbon-carbon double bond in the molecule such as ethylene, and is generally represented by -C ｘ H ２ｘ－２ -(where x is an integer of at least 2). In the present specification, the "alkynylene group" refers to a divalent group formed by losing two hydrogen atoms from an aliphatic hydrocarbon having one carbon-carbon triple bond in the molecule such as acetylene, and is generally represented by -C ｘ H ２ｘ－４- represented by (where x is an integer of 2 or more). Examples of the alkylene group having 1 to 15 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, an adamantylene group, a tert-butylene group, an isopropylene group, etc. Examples of the alkenylene group having 2 to 15 carbon atoms include an ethenylene group (—CH═CH—), a propenylene group (—CH ２ CH═CH—), a butenylene group (—CH ２ CH═CHCH ２ —), etc. Here, "═" represents a carbon-carbon double bond. Examples of the alkynylene group having 2 to 15 carbon atoms include an ethynylene group (—C≡C—), a propynylene group (—CH ２ C≡C—), a butynylene group (—CH ２ C≡CCCH ２ —), etc., where "≡" represents a carbon-carbon triple bond. As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, an alkylene group having 1 to The alkylene group having 1 to 15 carbon atoms is preferably used in terms of the stability of the compound, and the methylene group or the ethylene group is more preferably used in terms of ease of synthesis, and the methylene group is even more preferably used in terms of excellent device performance. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched or cyclic. n represents 1, 2 or 3. From the viewpoint of ease of synthesis, n is preferably 1 or 2, and more preferably 1 from the viewpoint of the stability of the compound.

[0030] When used as an organic electronic device, it is preferable that the thin film has heat resistance, and a high glass transition temperature of the compound is preferred. According to the present inventors, from the viewpoint that the glass transition temperature of the compound is difficult to decrease, as the alkylcyano group, R １If it is a linear aliphatic hydrocarbon group, make it relatively small, such as having 2 or fewer carbon atoms, or R １ It is preferable that the group is a branched aliphatic hydrocarbon group. Another approach to increase the glass transition temperature is to introduce an aromatic hydrocarbon group having 6 to 20 carbon atoms that may be substituted with a cyano group, a heteroaromatic group having 3 to 20 carbon atoms that may be substituted with a cyano group, or a cyclic alkyl group (including a spiro structure) that may be substituted with a cyano group to the alkylcyano group. This is because alkylcyano groups like the ones described above tend to suppress molecular motion due to heat.

[0031] Alkylcyano group R １ As preferred examples of -(CN)n, (R-1) to (R-56) below are listed as preferred examples.

[0032]

[0033]

[0034] Ar in equation (1) １ R １１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. １１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F (fluorine), Cl (chlorine), Br (bromine), and CF. ３ (Trifluoromethyl), a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents.

[0035] Ar １Preferably, the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof. Also, Ar １ It is particularly preferable that the group is a phenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, cyanophenyl group, dicyanophenyl group, methylphenyl group, dimethylphenyl group, biphenyl group, cyanobiphenyl group, dicyanobiphenyl group, pyridylphenyl group, pyridylbenzonitrile group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, methylpyridyl group, dimethylpyridyl group, phenylpyridyl group, cyanophenylpyridyl group, bipyridyl group, terpyridyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, isoquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, phenantrenyl group, anthryl group, phenantrolyl group, dimethylfluorenyl group, diphenylfluorenyl group, or spirofluorenyl group. １ It is even more preferable that the group is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

[0036] Considering the availability of raw materials and ease of synthesis, Ar １ R １１ A phenyl group which may be substituted with R １１ Naphthyl group, R may be substituted with １１ A pyridyl group may be substituted with R １１ A pyrazyl group which may be substituted with R １１ A pyrimidyl group which may be substituted with R １１A triazyl group may be substituted with R １１ A quinolyl group which may be substituted with R １１ Isoquinolyl group, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, heptyl group, hexyl group, cyclohexyl group, adamantyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylethyl group, diadamantylmethyl group, or dicyclohexylmethyl group may be substituted with; phenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, bistrifluoromethylphenyl group, biphenylyl group, cyanobiphenylyl group, trifluoromethylbiphenylyl group, naphthyl group, Preferably, the substituent is a cyanonaphthyl group, fluoronaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, cyanopyrimidyl group, dicyanopyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, fluoroquinolyl group, difluoroquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, fluoroisoquinolyl group, or difluoroisoquinolyl group. Furthermore, if heat resistance of the film is required, it is effective to increase the glass transition temperature (Tg) of the material. Increasing the rotational energy of the substituent is effective in increasing Tg, and Ar １ It is preferable that the material has a fused ring structure as a substructure. Preferred examples of the fused ring structure include naphthyl groups, quinolyl groups, isoquinolyl groups, etc., with quinolyl groups being the most preferred.

[0037] R １１ Examples include cyano groups, F, and CF. ３ Phenyl group, naphthyl group, pyridyl group, pyrazyl group, triazyl group, quinolyl group, isoquinolyl group, adamantyl group, cyclohexyl group, cyclopentyl group, cyclobutyl group, cyclopropyl group, methyl group, ethyl group, or a combination thereof is preferred. In terms of good element performance, R１１ This includes cyano group, trifluoromethyl group, phenyl group, cyanophenyl group, dicyanophenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, naphthyl group, cyanonaphthyl group, dicyanonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, bistrifluoromethylnaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, pyrimidyl group, Cyanopyrimidyl group, dicyanopyrimidyl group, fluoropyrimidyl group, difluoropyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, pyrazyl group, cyanopyramyrazyl group, dicyanopyramyrazyl group, fluoropyramyrazyl group, difluoropyramyrazyl group, trifluoromethylpyramyrazyl group, bistrifluoromethylpyramyrazyl group, triazyl group, cyanotriazyl group, dicyanotriazyl group, fluorotriazyl group, difluorotriazyl group, trifluoromethyltriazyl group, bistrifluoromethyltriazyl group, adamantyl group, cyclohexyl group, or methyl group are preferred. Considering the availability of raw materials and ease of synthesis, R １１ The group is preferably a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a pyridyl group, or a cyanopyridyl group, with a cyano group being more preferred.

[0038] R １１ Examples of the C6-C30 aromatic hydrocarbon group in this context include phenyl group, naphthyl group, anthryl group, phenantrenyl group, pyrenyl group, perilenyl group, triphenylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, biphenylyl group, terphenyl group, naphthylphenyl group, phenylnaphthyl group, binaphthyl group, anthrylphenyl group, phenylanthryl group, naphthylanthryl group, and the like. Phenyl or naphthyl groups are preferred in terms of superior element performance. １１In the above, the heteroaromatic groups having 3 to 30 carbon atoms include pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, quinolyl group, isoquinolyl group, quinazolyl group, naphthyridyl group, quinoxalyl group, pyridopyradyl group, pteridyl group, pyrazinopyradyl group, pyrimidopyridyl group, benzoquinolyl group, benzoisoquinolyl group, benzoquinoxalyl group, phenantrolyl group, phenanthridyl group, acridyl group, and phen Examples of groups include nadinyl group, phenoxazinyl group, phenothiazinyl group, hexaazatriphenylenyl group, thienyl group, furyl group, benzothienyl group, benzofuryl group, isobenzofuryl group, dibenzothiophenyl group, dibenzofuranyl group, benzoxazolyl group, pyrrole group, indole group, isoindole group, indolidinyl group, purine group, imidazolyl group, carbazolyl group, thiazolyl group, and thiadiazolyl group. Pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, or isoquinolyl group are preferred in terms of excellent device performance, and pyridyl group or pyrazyl group are even more preferred in terms of ease of synthesis.

[0039] R １１ Examples of the C2-C15 perfluoroalkyl group in this context include perfluoroethyl, perfluoropropyl, perfluorobutyl, perfluoropentane, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorononane, perfluorodecane, perfluoroundecane, perfluorododecane, tridecane, perfluorotetradecane, and perfluoropentadecane groups, which may be branched or cyclic perfluoroalkyl groups. １１ Examples of C1-C30 alkyl groups that may have a cyclic structure include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, tert-butyl, and isopropyl groups. C1-C10 alkyl groups that may have a cyclic structure are preferred because they are easy to synthesize, and examples include adamantyl, methyl, or ethyl groups. Methyl groups are even more preferred because they offer superior device performance.

[0040] Ar explained above １ Preferred examples include (E-1) to (E-348) below.

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms. The aromatic hydrocarbon ring and the heteroaromatic ring may each be a monoring, a fused ring, or a linked ring, and the linked ring may be bonded by methylene groups substituted with trifluoromethyl groups. The aromatic hydrocarbon ring and the heteroaromatic ring are one or more groups Y selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. ２ The aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with the aromatic hydrocarbon group or the heteroaromatic group by one or more selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0058] A preferred example of ring A is one or more of the above-mentioned groups Y. ２ The following (A-1) to (A-17) may be substituted with the above. In terms of excellent hole transport promoting performance, (A-1) to (A-6) and (A-9) to (A-13) are particularly preferred as ring A. In terms of easy availability of raw materials and low-cost manufacturing, (A-1) or (A-2) are even more preferred as ring A. In terms of good synthesis yield, (A-2) is particularly preferred as ring A. (In formulas (A-1) to (A-17), Y ２ (where l represents the same substituent as above, and p represents 0, 1, or 2, and 0 ≤ l + p ≤ 4.)

[0059] Furthermore, preferred ring fusion positions (A-1) to (A-17) in ring A include, for example, (A-1') to (A-17') below. (In formulas (A-1') to (A-17'), Y ２ (where l represents the same substituent as above, and p represents 0, 1, or 2, and 0 ≤ l + p ≤ 4.)

[0060] The compound represented by formula (1) described above has ring A at the center with Ar on one side. １ On the other hand, alkylcyano group R １ It has a left-right asymmetric structure with -(CN)n, which makes it more likely to have amorphous properties.

[0061] 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.

[0062] 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.

[0063] Preferred examples of imide compounds represented by formula (1) include, for example, (D-1) to (D-276) below. However, the compounds of the present invention are not limited to these.

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087] Of the above, compounds having at least eight heteroatoms in the molecule are particularly preferred in order to enhance interaction with adjacent layers such as hole transport layers. Furthermore, compounds having at least four nitrogen atoms in the molecule are even more preferred in order to improve adhesion with electrodes.

[0088] [Manufacturing Method] The compound represented by formula (1) can be synthesized by known methods or a combination thereof. For example, a tetracarboxylic dianhydride represented by formula (1a) below is reacted with an amine compound represented by formula (5) below to obtain a compound represented by formula (1b) below (Step 1). Furthermore, the obtained compound represented by formula (1b) below is reacted with an amine compound represented by formula (6) below to synthesize an imide compound represented by formula (1) below (Step 2). The imide compound represented by formula (1) can be synthesized in two steps (Steps 1 and 2) in this way, or it can be synthesized in one step.

[0089] (In the formula, Ar １ Ar ２(and ring A has the same definition as in formula (1) above.) The amino compound represented by formula (5) or (6) 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.

[0090] The compound represented by formula (1b) or the imide compound represented by (1) above can be synthesized by referring to known methods, for example (Organic Chemistry Frontiers, 2021, Vol. 8, pp. 522-530; Chemistry A European Journal, 2006, Vol. 12, pp. 6592-6606; Journal of Materials Chemistry A, 2015, Vol. 3, pp. 878-885, etc.).

[0091] 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, DMF, DMAc, pyridine, quinoline, and mixed solvents thereof are preferred in terms of good reaction yield.

[0092] 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, 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, the condensing agent used in step 1 is more preferably triethylamine, pyridine, or EDC in that it yields a good reaction yield of the compound represented by formula (1b). Furthermore, the condensing agent used in step 2 is preferably an organic base in that it yields a good reaction yield of the imide compound represented by formula (1), and more preferably 1,4-diazabicyclo[2.2.2]octane.

[0093] 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 (1b) or the tetracarboxylic dianhydride represented by formula (1a). The amount of amine compound represented by formula (6) used is preferably in the range of 1.0 to 1.2 moles, per mole of the compound represented by formula (1b), in terms of reaction yield and production efficiency. Furthermore, the amount of amine compound represented by formula (5) used is preferably in the range of 0.3 to 1.5 moles, and more preferably in the range of 0.5 to 1.1 moles, per mole of the tetracarboxylic dianhydride represented by formula (1a).

[0094] 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.

[0095] <<Effects of Compounds Having the Structure Represented by Formula (1)>> Compounds having the structure represented by formula (1) have a naphthalenetetracarboxylic acid diimide skeleton or a similar specific skeleton structure, 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), it is expected that the interaction with the HOMO orbitals of the adjacent hole transport layer will increase, and 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 a naphthalenetetracarboxylic acid diimide skeleton or a similar specific skeleton structure, thermal stability and high reduction resistance can also be expected.

[0096] 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.

[0097] (Organic Electronic Device Material) The present invention relates to an organic electronic device material represented by the following formula (2). In formula (2), Ar ２ R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. ２Y represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group is one or more groups selected from hydroxyl group, carboxyl group, formyl group, nitro group, fluoro group, chloro group, bromo group, iodine group, trifluoromethyl group, cyano group, carbon-oxygen double bond, carbon-sulfur double bond, aromatic hydrocarbon group having 6 to 20 carbon atoms, heteroaromatic group having 3 to 20 carbon atoms, and aliphatic hydrocarbon group having 1 to 15 carbon atoms. １ The aliphatic hydrocarbon group may be substituted with a , and the aliphatic hydrocarbon group may be linear, branched, or cyclic. n represents 1, 2, or 3. Ring B represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms, and the aromatic hydrocarbon ring and the heteroaromatic ring may each be monocyclic, fused, or linked rings, and the linked ring may be bonded by methylene groups substituted with trifluoromethyl groups.

[0098] Alkylcyano group R ２ - (CN)n R ２ The symbol represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. Furthermore, the aliphatic hydrocarbon group may be a group formed by combining a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group. Examples of saturated aliphatic hydrocarbon groups include alkylene groups having 1 to 15 carbon atoms. Examples of unsaturated aliphatic hydrocarbon groups include alkenylene groups having 2 to 15 carbon atoms and alkylylene groups having 2 to 15 carbon atoms. The unsaturated aliphatic hydrocarbon group may have two or more carbon-carbon double bonds, two or more carbon-carbon triple bonds, or both carbon-carbon double bonds and carbon-carbon triple bonds. Examples of alkylene groups having 1 to 15 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, adamantylene, tert-butylene, and isopropylene. Examples of alkenylene groups having 2 to 15 carbon atoms include ethenylene (-CH=CH-) and propenylene (-CH=CH-).２ CH=CH-), butenylene group (-CH ２ CH = CHCH ２ Examples include the ethylylene group (-C≡C-) and the propynylene group (-CH₂). Examples of alkynylene groups having 2 to 15 carbon atoms include the ethynylene group (-C≡C-) and the propynylene group (-CH₂). ２ C≡C-), butynylene group (-CH ２ C≡CCH ２ Examples include -). As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, alkylene groups having 1 to 15 carbon atoms are preferred in terms of the stability of the compound, methylene groups or ethylene groups are more preferred in terms of ease of synthesis, and methylene groups are even more preferred in terms of superior device performance. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from hydroxyl groups, carboxyl groups, formyl groups, nitro groups, fluoro groups, chloro groups, bromo groups, iodo groups, trifluoromethyl groups, cyano groups, carbon-oxygen double bonds, carbon-sulfur double bonds, aromatic hydrocarbon groups having 6 to 20 carbon atoms, heteroaromatic groups having 3 to 20 carbon atoms, and aliphatic hydrocarbon groups having 1 to 15 carbon atoms. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched, or cyclic. n represents 1, 2, or 3. n is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound.

[0099] Alkylcyano group R ２ As preferred examples of -(CN)n, (R-1) to (R-56) described above are given as preferred examples.

[0100] Ar in equation (2) ２ R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. ２１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F (fluorine), Cl (chlorine), Br (bromine), and CF. ３(Trifluoromethyl), a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents.

[0101] Ar ２ Preferably, the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof. Also, Ar ２ It is particularly preferable that the group is a phenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, cyanophenyl group, dicyanophenyl group, methylphenyl group, dimethylphenyl group, biphenyl group, cyanobiphenyl group, dicyanobiphenyl group, pyridylphenyl group, pyridylbenzonitrile group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, methylpyridyl group, dimethylpyridyl group, phenylpyridyl group, cyanophenylpyridyl group, bipyridyl group, terpyridyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, isoquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, phenantrenyl group, anthryl group, phenantrolyl group, dimethylfluorenyl group, diphenylfluorenyl group, or spirofluorenyl group. ２ It is even more preferable that the group is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

[0102] Considering the availability of raw materials and ease of synthesis, the above Ar ２ R ２1 A phenyl group which may be substituted with R２1 Naphthyl group, R may be substituted with ２1 A pyridyl group may be substituted with R ２1 A pyrazyl group which may be substituted with R ２1 A pyrimidyl group which may be substituted with R ２1 A triazyl group may be substituted with R ２1 A quinolyl group which may be substituted with R ２1 Isoquinolyl group, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, heptyl group, hexyl group, cyclohexyl group, adamantyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylethyl group, diadamantylmethyl group, dicyclohexylmethyl group are preferred, and phenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, bistrifluoromethylphenyl group, biphenylyl group, cyanobiphenylyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group Anonaphthyl group, fluoronaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, cyanopyrimidyl group, dicyanopyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, fluoroquinolyl group, difluoroquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, fluoroisoquinolyl group, or difluoroisoquinolyl group are more preferred.

[0103] R ２１ A preferred example is the R １１ Similar bases can be cited.

[0104] Ar explained above ２ Preferred examples include (E-1) to (E-348) described above.

[0105] A preferred example of ring B is one or more of the above-mentioned groups Y. ２The following (B-1) to (B-17) may be substituted with the above. In terms of excellent hole transport promoting performance, (B-1) to (B-6) and (B-9) to (B-13) are particularly preferred as ring B. In terms of easy availability of raw materials and low-cost manufacturing, (B-1) or (B-2) are even more preferred as ring B. In terms of good synthesis yield, (B-2) is particularly preferred as ring B. (In formulas (B-1) to (B-17), Y ２ (where l represents the same substituent as above, and p represents 0, 1, or 2, and 0 ≤ l + p ≤ 4.)

[0106] Furthermore, preferred ring fusion positions (B-1) to (B-17) in ring B include, for example, the same ring fusion positions as (A-1') to (A-17') described above.

[0107] (Imide Compounds) The present invention relates to imide compounds represented by the following formula (3) or formula (4). In formula (3), Ar ３ is R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. ３ The symbol represents an aliphatic hydrocarbon group with 1 to 15 carbon atoms, and m represents 1, 2, or 3. １ and T ２ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these.

[0108] In formula (4), Ar ４ is R ４１A C6-C30 aromatic hydrocarbon group, which may be substituted with R ４１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. ４ The symbol represents an aliphatic hydrocarbon group with 1 to 15 carbon atoms, and m represents 1, 2, or 3. ３ , T ４ , T ５ and T ６ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. However, T ３ , T ４ , T ５ and T ６ However, all of them are hydrogen atoms, m=1, and R ４ When it is a methylene group, Ar ４ This does not result in an unsubstituted 2-pyridyl group or an unsubstituted 2-pyradyl group.

[0109] R is an alkylcyano group ３ - (CN)m R ３ , and R ４ - (CN)m R ４ R represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. ３ and R ４ The aliphatic hydrocarbon group may be linear, branched, or cyclic. Also, R ３ and R ４The aliphatic hydrocarbon group may be substituted with one or more groups selected from hydroxyl, carboxyl, formyl, nitro, fluoro, chloro, bromo, iodo, trifluoromethyl, cyano, carbon-oxygen double bond, carbon-sulfur double bond, C6-C20 aromatic hydrocarbon group, C3-C20 heteroaromatic group, and C1-C15 aliphatic hydrocarbon group.

[0110] R ３ and R ４ Preferably, the group is methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, adamantylene, tert-butylene, or isopropylene. In order to avoid lowering the glass transition temperature, R ３ and R ４ It is particularly preferable that it be a methylene group or an ethylene group. １ The methylene group or ethylene group may be substituted with one or more groups selected from hydroxyl groups, carboxyl groups, formyl groups, nitro groups, fluoro groups, chloro groups, bromo groups, iodo groups, trifluoromethyl groups, cyano groups, carbon-oxygen double bonds, carbon-sulfur double bonds, aromatic hydrocarbon groups having 6 to 20 carbon atoms, heteroaromatic groups having 3 to 20 carbon atoms, and aliphatic hydrocarbon groups having 1 to 15 carbon atoms. ３ and R ４ In terms of superior device performance, it is preferable that each methylene group is independently substituted with a cyano group, a phenyl group, a cyanophenyl group, or a pyridyl group. In order to lower the deposition temperature during film formation and suppress thermal decomposition, R ３ and R ４ It is more preferable that n is an unsubstituted (without substituents) methylene group or an unsubstituted ethylene group. n represents 1, 2, or 3. In terms of superior device performance, n is preferably 1 or 2, and particularly preferably 1.

[0111] Ar in equation (3) ３ R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１A heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. ４ R ４１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ４１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings. ３１ and R ４１ These include aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F (fluorine), Cl (chlorine), Br (bromine), and CF. ３ (Trifluoromethyl), a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents.

[0112] Ar ３ Preferably, the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof. Also, Ar ３It is particularly preferable that the group is a phenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, cyanophenyl group, dicyanophenyl group, methylphenyl group, dimethylphenyl group, biphenyl group, cyanobiphenyl group, dicyanobiphenyl group, pyridylphenyl group, pyridylbenzonitrile group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, methylpyridyl group, dimethylpyridyl group, phenylpyridyl group, cyanophenylpyridyl group, bipyridyl group, terpyridyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, isoquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, phenantrenyl group, anthryl group, phenantrolyl group, dimethylfluorenyl group, diphenylfluorenyl group, or spirofluorenyl group. ３ It is even more preferable that the group is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

[0113] Ar ４ Preferably, the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof. Also, Ar ４It is particularly preferable that the group is a phenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, cyanophenyl group, dicyanophenyl group, methylphenyl group, dimethylphenyl group, biphenyl group, cyanobiphenyl group, dicyanobiphenyl group, pyridylphenyl group, pyridylbenzonitrile group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, methylpyridyl group, dimethylpyridyl group, phenylpyridyl group, cyanophenylpyridyl group, bipyridyl group, terpyridyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, isoquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, phenantrenyl group, anthryl group, phenantrolyl group, dimethylfluorenyl group, diphenylfluorenyl group, or spirofluorenyl group. ４ It is even more preferable that the group is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

[0114] R ３１ and R ４１ A preferred example is the R １１ Similar bases can be cited.

[0115] T in equation (3) １ and T ２ Furthermore, T in equation (4) ３ , T ４ , T ５ and T ６ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. However, T ３ , T ４ , T ５ and T ６ However, all of them are hydrogen atoms, m=1, and R４ When it is a methylene group, Ar ４ This does not result in an unsubstituted 2-pyridyl group or an unsubstituted 2-pyradyl group. In terms of superior device performance, T in formula (3) １ ~T ２ or T in formula (4) above ３ ~T ６ However, it is preferable that the group is a hydrogen atom, a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

[0116] <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".

[0117] 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.

[0118] <<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.

[0119] 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.

[0120] [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.

[0121] 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.

[0122] 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.

[0123] [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.

[0124] [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.

[0125] 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.

[0126] [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.

[0127] 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).

[0128] 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.

[0129] (i) Specific examples of coumarin derivatives include coumarin 6 and coumarin 30. Specific examples of quinacridone derivatives include N,N-dimethylquinacridone. Specific examples of phthalocyanine derivatives include boron subphthalocyanine chloride and boron subnaphthalocyanine chloride (SubNC). (ii) Specific examples of fullerenes and their derivatives include

[60] fullerene,

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

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

[0130] 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).

[0131] [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.

[0132] 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.

[0133] 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.

[0134] [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.

[0135] [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.

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] <<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.

[0141] [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).

[0142] [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.

[0143] [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.

[0144] [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.

[0145] [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.

[0146] [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.

[0147] 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.

[0148] [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.

[0149] <<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.

[0150] [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.

[0151] 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.

[0152] [Hole Injection Layer 22] A hole injection layer 22 is provided between the first electrode 21 and the hole transport layer 23, which will be described later. The hole injection layer 22 is provided to promote hole transport from the first electrode 21 to the hole transport layer 23. The hole injection layer 22 contains the compound represented by formula (1) above as a hole injection material. The hole injection layer 22 may also contain compounds other than the compound represented by formula (1) above. Examples of compounds that can be contained in the hole injection layer 22 include conventionally known hole transport materials.

[0153] [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.

[0154] [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.

[0155] [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. Examples of electron transport materials include, but are not limited to, triazine derivatives, tris(8-quinolinolato)aluminum (Alq3), bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)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.

[0156] [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.

[0157] [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.

[0158] 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.

[0159] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. The obtained compounds are １ Identification was made based on the H-NMR spectrum (400 MHz). １ For the measurement of the H-NMR spectrum, a Bruker ASCEND 400 (400 MHz; manufactured by BR UKER) was used. １The H-NMR spectrum is deuterated chloroform (CDCl). ３ ) or didimethyl sulfoxide (DMSO-d ６ The measurement was performed using ) as the solvent and tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0160] (Synthesis Example 1: Synthesis of Compound (D-38)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (6.40 g, 20.9 mmol), 4-aminoquinoline (3.62 g, 25.1 mmol), and isoquinoline (2.30 g, 17.8 mmol) were suspended in m-cresol (105 mL) and stirred at 120°C for 10 hours. After cooling to room temperature, 800 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization in a mixed solvent of DMF and acetic acid to obtain the target compound (D-38) as a white solid (4.00 g, yield 89%). １ H-NMR (DMSO-d6) δ (ppm): 5.15 (s, 2H), 7.59 (dd, J = 7.6, 1.2Hz, 1H), 7.79 (d, J = 4.5Hz, 1H), 7.86 (dd, J = 7.7, 1 .4Hz, 1H), 8.19 (dd, J=7.4, 1.0Hz, 2H), 8.74 (d, J=7.6Hz, 2H), 8.81 (d, J=7.6Hz, 2H), 9.14 (d, J=4.5Hz, 1H).

[0161] (Synthesis Example 2: Synthesis of Compound (D-76)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (0.31 g, 1.00 mmol), [3,4'-bipyridine]-4-amine (0.21 g, 1.20 mmol), and isoquinoline (65.9 mg, 0.51 mmol) were suspended in DMF (5 mL) and stirred at 120°C for 6 hours. After cooling to room temperature, the reaction mixture was removed by distillation under reduced pressure, and 50 mL of ethanol was added. The precipitate (crude product) was filtered off. The obtained crude product was washed with ethanol to obtain the target compound (D-76) as a pale yellow solid (0.25 g, yield 53%). １ H-NMR (DMSO-d6) δ (ppm): 5.10 (s, 2H), 7.31 (dd, J = 4.5, 1.6Hz, 2H), 7.79 (d, J = 5.1Hz, 1H), 8.48 (dd, J=4.4, 1.6Hz, 2H), 8.68 (d, J=7.5Hz, 2H), 8.73 (d, J=7.6Hz, 2H), 8.87 (s, 1H), 8.92 (d, J=5.3Hz, 1H).

[0162] (Synthesis Example 3: Synthesis of Compound (D-131)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (3.06 g, 10.0 mmol), 2-amino-4-cyanothiazole (1.50 g, 12.0 mmol), and isoquinoline (1.11 g, 8.60 mmol) were suspended in m-cresol (50 mL) and stirred at 120°C for 8 hours. After cooling to room temperature, 100 mL of toluene was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and toluene to obtain the target compound (D-131) as a pale yellow solid (2.70 g, yield 67%). １ H-NMR (DMSO-d6) δ (ppm): 5.12 (brs, 2H), 8.77 (brs, 4H), 9.14 (s, 1H).

[0163] (Synthesis Example 4: Synthesis of Compound (D-10)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (2.00 g, 6.53 mmol), 3-aminobenzonitrile (0.85 g, 7.18 mmol), and isoquinoline (0.72 g, 5.55 mmol) were suspended in m-cresol (33 mL) and stirred at 120°C for 14 hours. After cooling to room temperature, 90 mL of toluene was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and toluene to obtain the target compound (D-10) as a pale yellow solid (1.70 g, yield 64%). １ H-NMR (DMSO-d6) δ (ppm): 5.13 (s, 2H), 7.81 (t, J = 8.0Hz, 1H), 7.87 (ddd, J =8.1, 2.1, 1.5Hz, 1H), 8.01-8.03 (m, 2H), 8.75 (brs, 2H), 8.78 (brs, 2H).

[0164] (Synthesis Example 5: Synthesis of Compound (D-58)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (1.58 g, 5.16 mmol), 9-aminoacridin (1.20 g, 6.19 mmol), and isoquinoline (0.66 g, 5.16 mmol) were suspended in DMF (33 mL) and stirred at 150°C for 10 hours. After cooling to room temperature, 100 mL of water was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-58) as a reddish-brown solid (0.82 g, yield 33%). １ H-NMR (DMSO-d6) δ (ppm): 5.18 (s, 2H), 7.62 (ddd, J = 8.6, 6.7, 1.2Hz, 2H), 7.94 (ddd, J = 8.9, 6.7, 1. 4Hz, 2H) 8.30 (d, J = 8.8Hz, 2H), 8.33 (d, J = 8.7Hz, 2H), 8.78 (d, J = 7.6Hz, 2H), 8.84 (d, J = 7.7Hz, 2H).

[0165] (Synthesis Example 6: Synthesis of Compound (D-11)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (3.00 g, 9.80 mmol), 4-aminophthalonitrile (1.54 g, 10.8 mmol), and isoquinoline (1.08 g, 8.33 mmol) were suspended in DMF (49 mL) and stirred at 150°C for 13 hours. After cooling to room temperature, 100 mL of water was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-11) as a pale yellow solid (2.00 g, yield 47%). １ H-NMR (DMSO-d6) δ (ppm): 5.13 (s, 2H), 8.11 (dd, J = 8.4, 2.0Hz, 1H), 8.34 (dd, J = 2.0, 0 .4Hz, 1H), 8.40 (dd, J=8.3, 0.4Hz, 1H), 8.75 (d, J=7.7Hz, 2H), 8.80 (d, J=7.7Hz, 2H).

[0166] (Synthesis Example 7: Synthesis of Compound (D-57)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (2.50 g, 8.16 mmol) and 5-aminophenanthroline (1.54 g, 10.8 mmol) were suspended in DMF (82 mL) and stirred at 140°C for 10 hours. After cooling to room temperature, 100 mL of ethanol and 100 mL of water were added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target compound (D-57) as a pale yellow solid (1.50 g, yield 38%). １ H-NMR (DMSO-d6) δ (ppm): 5.16 (s, 2H), 7.75 (dd, J = 8.2, 4.3Hz, 1H), 7.88 (dd, J = 8.0, 4.3Hz, 1H), 8.27 (s, 1H), 8.57 (dd, J = 8.2, 1.5Hz, 1 H), 8.72 (dd, J=8.3, 1.7Hz, 1H), 8.76 (d, J=7.5Hz, 2H), 8.82 (d, J=7 .5Hz, 2H), 9.18 (dd, J=4.4, 1.6Hz, 1H), 9.23 (dd, J=4.4, 1.6Hz, 1H).

[0167] (Synthesis Example 8: Synthesis of Compound (D-65)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (2.20 g, 7.18 mmol), 2'-amino[1,1'-biphenyl]-4-carbonitrile (1.53 g, 7.90 mmol), and imidazole (245 mg, 3.59 mmol) were suspended in DMF (37 mL) and stirred at 120°C for 9 hours. After cooling to room temperature, 37 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-65) as a white solid (2.30 g, yield 66%). １ H-NMR (DMSO-d6) δ (ppm): 5.10 (s, 2H), 7.39 (d, J = 8.6Hz, 2H), 7.56-7.59 (m, 1H), 7.6 6-7.67 (m, 3H), 7.71 (d, J=8.6Hz, 2H), 8.65 (d, J=7.7Hz, 2H), 8.72 (d, J=7.6Hz, 2H).

[0168] (Synthesis Example 9: Synthesis of Compound (D-77)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (1.80 g, 5.88 mmol) and 4-(4-amino-3-pyridinyl)benzonitrile (1.26 g, 6.47 mmol) were suspended in DMF (20 mL) and stirred at 140°C for 4 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF, acetic acid, and ethanol to obtain the target compound (D-77) as a white solid (1.60 g, yield 56%). １ H-NMR (DMSO-d6) δ (ppm): 5.11 (s, 2H), 7.48 (d, J = 8.8Hz, 2H), 7.77-7.79 (m, 3H), 8 .67 (d, J=7.6Hz, 2H), 8.73 (d, J=7.6Hz, 2H), 8.84 (brs, 1H), 8.91 (d, J=5.3Hz, 1H).

[0169] (Synthesis Example 10: Synthesis of Compound (D-44)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (1.50 g, 4.90 mmol), 4-aminoquinoline-2-carbonitride (0.99 g, 5.88 mmol), and 1,4-diazabicyclo[2.2.2]octane (275 mg, 2.55 mmol) were suspended in DMF (25 mL) and stirred at 120°C for 12 hours. After cooling to room temperature, ethanol (75 mL) was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-44) as a white solid (1.60 g, yield 58%). １ H-NMR (DMSO-d6) δ (ppm): 5.15 (s, 2H), 7.82 (ddd, J = 8.7, 6.9, 1.2Hz, 1H), 8.05 (ddd, J = 8.7, 6.9, 1.3Hz, 1H), 8.34 (brd, J=8.6Hz, 1H), 8.38 (s, 1H), 8.43 (brd, J=8.6Hz, 1H), 8.75 (d, J=7.6Hz, 2H), 8.82 (d, J=7.7Hz, 2H).

[0170] (Synthesis Example 11: Synthesis of Compound (D-78)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (1.90 g, 6.20 mmol), 3-(4-amino-3-pyridinyl)benzonitrile (1.45 g, 7.45 mmol), and isoquinoline (401 mg, 3.10 mmol) were suspended in DMF (31 mL) and stirred at 120°C for 8 hours. After cooling to room temperature, 300 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-78) as a pale yellow solid (2.30 g, yield 77%). １H-NMR (DMSO-d6) δ (ppm): 5.10 (s, 2H), 7.46 (t, J = 7.8Hz, 1H), 7.56 (ddd, J = 7.8, 2.0, 1.3Hz, 1H), 7.74 (ddd, J = 7.8, 8. 2, 2.0Hz, 1H), 7.77-7.79 (m, 2H), 8.69 (d, J = 7.7Hz, 2H), 8.73 (d, J = 7.6Hz, 2H), 8.86 (brs, 1H), 8.90 (d, J = 5.2Hz, 1H).

[0171] (Synthesis Example 12: Synthesis of Compound (D-101)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (3.10 g, 10.1 mmol), 2-amino[1,1'-biphenyl]-4,4'-dicarbonitride (2.66 g, 12.1 mmol), and imidazole (345 mg, 5.06 mmol) were suspended in DMF (51 mL) and stirred at 120°C for 9 hours. After cooling to room temperature, 600 mL of ethanol and 300 mL of water were added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-101) as a pale red solid (1.77 g, yield 34%). １ H-NMR (DMSO-d6) δ (ppm): 5.10 (s, 2H), 7.44 (d, J = 8.6Hz, 2H), 7.77 (d, J = 8.6Hz, 2H), 7.84 (d, J = 8.1Hz, 1H), 8.18 (dd, J=8.1, 1.8Hz, 1H), 8.23 ​​(d, J=1.5Hz, 1H), 8.67 (d, J=7.5Hz, 2H), 8.73 (d, J=7.3Hz, 2H).

[0172] (Synthesis Example 13: Synthesis of Compound (D-113)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (2.20 g, 7.18 mmol), 2-amino[1,1'-biphenyl]-5,4'-dicarbonitric acid (1.89 g, 7.18 mmol), and imidazole (464 mg, 3.59 mmol) were suspended in DMF (36 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, 360 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-113) as a pale yellow solid (2.20 g, yield 60%). １ H-NMR (DMSO-d6) δ (ppm): 5.10 (s, 2H), 7.44 (d, J = 7.5 Hz, 2H), 7.75 (d, J = 7.8 Hz, 2H), 7.93 (brd, J = 8.2 Hz, 1 H), 8.15 (d, J=1.8Hz, 1H), 8.19 (dd, J=8.3, 1.8Hz, 1H), 8.66 (brd, J=7.1Hz, 2H), 8.73 (brd, J=6.9Hz, 2H).

[0173] (Synthesis Example 14: Synthesis of Compound (D-89)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (2.50 g, 8.16 mmol), 4-(3-amino-2-pyridinyl)benzonitrile (1.91 g, 9.80 mmol), and isoquinoline (527 mg, 4.08 mmol) were suspended in DMF (41 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, 400 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with acetic acid to obtain the target compound (D-89) as a pale yellow solid (1.60 g, yield 41%). １ H-NMR (DMSO-d6) δ (ppm): 5.11 (brs, 2H), 7.57 (d, J = 8.7, 2H), 7.74-7.77 (m, 3H), 8.1 6 (dd, J=8.0, 1.6Hz, 1H), 8.69 (brs, 2H), 8.74 (brs, 2H), 8.87 (dd, J=4.9, 1.5Hz, 1H).

[0174] (Synthesis Example 15: Synthesis of Compound (D-125)) Under an argon atmosphere, 7-cyanomethyl-1H-2-benzopyrano[6,5,4-Def]isoquinoline-1,3,6,8(7H)-tetraone (1.40 g, 4.57 mmol), 3,5-bis(pyridine-4-yl)aniline (1.36 g, 5.49 mmol), and imidazole (156 mg, 2.29 mmol) were suspended in DMF (46 mL) and stirred at 120°C for 10 hours. After cooling to room temperature, 70 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target compound (D-125) as a white solid (2.10 g, yield 86%). １ H-NMR (DMSO-d6) δ (ppm): 5.14 (s, 2H), 7.89 (dd, J = 4.4, 1.7Hz, 4H), 8.09 (d, J =1.7Hz, 2H), 8.39 (brs, 1H), 8.72 (dd, J=4.5, 1.6Hz, 4H), 8.75-8.83 (m, 4H).

[0175] (Synthesis Reference Example - 1: Synthesis of Intermediate Products) Under an argon atmosphere, 4-amino-3-bromobenzonitrile (10.0 g, 50.8 mmol), 4-cyanophenylboronic acid (8.96 g, 61.0 mmol), and tetrakis(triphenylphosphine)palladium (2.54 g, 2.94 mmol) were suspended in a mixed solvent of 2 M aqueous sodium carbonate (75 mL), toluene (254 mL), and ethanol (114 mL), and stirred at 90°C for 8 hours. After cooling to room temperature, 500 mL of water was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with toluene to obtain the target 2-amino[1,1'-biphenyl]-5,4'-dicarbonitride as a white solid (8.60 g, yield 77%). １ H-NMR (DMSO-d6) δ (ppm): 6.03 (brs, 2H), 6.83 (d, J = 8.6Hz, 1H), 7.41 (d, J = 2.0Hz , 1H), 7.47 (dd, J=8.6, 2.1Hz, 1H), 7.63 (d, J=8.5Hz, 2H), 7.93 (d, J=8.6Hz, 2H).

[0176] (Evaluation Example 1: Film Quality Evaluation of Compound (D-38)) 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 (D-38) 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) in the surface roughness measurement was 0.22 nm.

[0177] (Evaluation Example 2: Film Quality Evaluation of Compound (D-11)) The measurement was performed in the same manner as in Evaluation Example 1, except that compound (D-11) was used instead of compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.41 nm.

[0178] (Evaluation Example 3: Film Quality Evaluation of Compound (D-101)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (D-101) was used instead of compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.12 nm. (Evaluation Example 4: Film Quality Evaluation of Compound (D-77)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (D-77) was used instead of compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.15 nm. (Evaluation Example 5: Film Quality Evaluation of Compound (D-78)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (D-78) was used instead of compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.15 nm. (Evaluation Example 6: Film Quality Evaluation of Compound (D-113)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (D-113) was used instead of compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.15 nm. (Evaluation Example 7: Film Quality Evaluation of Compound (D-89)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (D-89) was used instead of compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.22 nm.

[0179] (Evaluation Reference Example 1: Film Quality Evaluation of Compound (R-1)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (R-1) was used instead of Compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 5.07 nm. Compound (R-1) was purchased from Tokyo Chemical Industry Co., Ltd. and purified by sublimation.

[0180] (Evaluation Reference Example 2: Film Quality Evaluation of Compound (R-2)) The measurement was performed in the same manner as in Evaluation Example 1, except that Compound (R-2) was used instead of Compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.52 nm. Compound (R-2) was synthesized according to the method disclosed in International Publication No. 2008 / 072586 and purified by sublimation.

[0181] (Evaluation Reference Example 3: Film Quality Evaluation of Imide Compound (R-3)) The measurement was performed in the same manner as in Evaluation Example 1, except that the imide compound (R-3) described below was used instead of the imide compound (D-38). The arithmetic mean roughness (Ra) in the surface roughness measurement was 10.0 nm. The imide compound (R-3) was synthesized by the method described in J. Am. Chem. Soc. 2011, 133, 15256-15259.

[0182] Based on the above film quality evaluation, it was confirmed that the films prepared using the compounds from Evaluation Examples 1 to 7 (D-38, D-11, D-101, D-77, D-78, D-113, D-89) exhibited even higher film smoothness than the films prepared using the compounds from Evaluation Reference Examples 1, 2, and 3 (R-1, R-2, R-3).

[0183] <Fabrication and Evaluation of Hole-Only Devices (HODs)> [HOD Example 1] A hole-only device (HOD) having a structure consisting of a first electrode, a hole injection layer, a hole transport layer, a hole transport enhancement layer, and a second electrode was fabricated, and the hole transport characteristics of the device were evaluated. (First Electrode) As a substrate with the first electrode on its surface, a glass substrate with an ITO transparent electrode, on which an ITO film (thickness 110 nm) was patterned in stripes, was prepared. This substrate was cleaned with isopropyl alcohol and then surface-treated by ozone ultraviolet cleaning.

[0184] (Preparation for vacuum deposition) Of the two surfaces of the substrate that had undergone the above surface treatment, each layer was deposited by vacuum deposition on the surface on which the ITO film was formed, thereby laminating each layer. First, the glass substrate was introduced into the vacuum deposition chamber, and 1.0 × 10 －４ The pressure was reduced to Pa. Then, each layer was fabricated according to the deposition conditions for each layer, in the following order.

[0185] (Preparation of hole injection layer) MoO in ITO film ３ A 1 nm film was deposited to create a hole injection layer. (Preparation of hole transport layer) A 100 nm film of (HTL-1) was deposited as a hole transport material to create a hole transport layer. (HTL-1) was synthesized by the method described in Japanese Patent Application Publication No. 2018-193371. (Preparation of hole transport-promoting layer) A hole transport-promoting layer was prepared by depositing a 10 nm film of the sublimation-purified compound (D-38).

[0186] (Fabrication of the second electrode) A second electrode was fabricated by depositing an 80 nm thin film of Au.

[0187] (Evaluation of hole transport capability of hole-only device) A positive and negative electric field was applied to the first and second electrodes of the hole-only device of HOD Example 1, respectively, at 10 mA / cm². ２ The voltage values ​​at the current density were measured. The results are shown in Table 1. Note that the voltage values ​​in the HOD example are relative values ​​with the results in HOD Reference Example 1, described later, set as the reference value (100). A lower voltage value indicates better performance.

[0188] [HOD Example 2] A hole-only device was fabricated in the same manner as in HOD Example 1, except that compound (D-11) was used instead of compound (D-38) which was used to fabricate the hole transport-promoting layer in HOD Example 1. The hole transport capacity of the obtained hole-only device was evaluated in the same manner as in HOD Example 1. The results are shown in Table 1.

[0189] [HOD Reference Example 1] A hole-only device was fabricated using the same method as in HOD Example 1, except that it did not have a hole transport-promoting layer. The hole transport capacity of the obtained hole-only device was evaluated using the same method as in HOD Example 1. The results are shown in Table 1.

[0190]

[0191] It was confirmed that the element in HOD Example 1, which used compound (D-38) as a hole transport promoting material, and the element in HOD Example 2, which used (D-11), exhibited a lower voltage compared to the element in HOD Reference Example 1, which did not use a hole transport promoting material.

[0192] <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.

[0193] (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 (D-38) 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.

[0194] 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 parameters. The response time (ms) 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.

[0195] The results are shown in Table 2. Note that the response time, dark current, and external quantum efficiency are relative values, with the results from Comparative Example 1 (described later) set as the baseline (100). A lower dark current value indicates better performance, and a higher external quantum efficiency value indicates better performance.

[0196] [Device Example 2] A photoelectric conversion element 1 was fabricated in the same manner as in Device Example 1, except that compound (D-11) was used instead of compound (D-38) in the fabrication of the hole transport enhancement 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 Example 3] A photoelectric conversion element 1 was fabricated in the same manner as in Device Example 1, except that compound (D-77) was used instead of compound (D-38) in the fabrication of the hole transport enhancement 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 Example 4] A photoelectric conversion element 1 was fabricated in the same manner as in Device Example 1, except that compound (D-113) was used instead of compound (D-38) in the fabrication of the hole transport enhancement 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] [Device Comparative Example 1] A photoelectric conversion element of Device Comparative Example 1 was fabricated in the same manner as Device Example 1, except that compound (R-1) was used instead of compound (D-38) 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 Comparative Example 2] A photoelectric conversion element of Device Comparative Example 2 was fabricated in the same manner as in Device Example 1, except that the hole transport promoting layer 12 was not provided. 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.

[0198]

[0199] As shown in Table 2, the elements of Element Example 1 and Element Example 2, using the photoelectric conversion element material for image sensors of the present invention, exhibited suppressed dark current and high external quantum efficiency compared to the elements of Comparative Example 1 and Comparative Example 2. Furthermore, the elements of Element Example 1 and Element Example 2, using the photoelectric conversion element material for image sensors of the present invention, showed improved response speed compared to the elements of Comparative Example 1 and Comparative Example 2.

[0200] 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.

[0201] 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 represented by the following formula (1). (In formula (1), Ar １ R １１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R １１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. １ Y represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group is one or more groups selected from hydroxyl group, carboxyl group, formyl group, nitro group, fluoro group, chloro group, bromo group, iodine group, trifluoromethyl group, cyano group, carbon-oxygen double bond, carbon-sulfur double bond, aromatic hydrocarbon group having 6 to 20 carbon atoms, heteroaromatic group having 3 to 20 carbon atoms, and aliphatic hydrocarbon group having 1 to 15 carbon atoms. １ The aliphatic hydrocarbon group may be substituted with a , and the aliphatic hydrocarbon group may be linear, branched, or cyclic, where n represents 1, 2, or 3. Ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms, and the aromatic hydrocarbon ring and the heteroaromatic ring may each be monocyclic, fused, or linked, and the linked ring may be bonded by a methylene group substituted with a trifluoromethyl group, and the aromatic hydrocarbon ring and the heteroaromatic ring may be one or more groups Y selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. ２ The aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with one or more atoms selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

2. 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 represented by formula (1), as described in claim 1.

3. The organic electronic element according to claim 2, wherein the light-receiving layer is a layer containing at least two organic components.

4. The organic electronic element according to any one of claims 1 to 3, wherein the organic layer includes a hole transport layer and a hole transport promoting layer containing a compound represented by formula (1), or includes a layer obtained by mixing a hole transport material and a compound represented by formula (1).

5. The organic electronic element according to claim 4, 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.

6. R in the formula (1) １ is a methylene group or an ethylene group, and the methylene group and the ethylene group are one or more groups Y selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms １ The organic electronic device according to any one of claims 1 to 3, which may be substituted with 7. R in formula (1) above １ The organic electronic element according to any one of claims 1 to 3, wherein the group is an unsubstituted methylene group or an unsubstituted ethylene group.

8. Ar in formula (1) １ The organic electronic device according to any one of claims 1 to 3, wherein the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof.

9. Ar in formula (1) １ The organic electronic element according to any one of claims 1 to 3, wherein the group is a phenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a fluorophenyl group, a difluorophenyl group, a perfluorophenyl group, a cyanophenyl group, a dicyanophenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, a cyanobiphenyl group, a dicyanobiphenyl group, a pyridylphenyl group, a pyridylbenzonitrile group, a pyridyl group, a cyanopyridyl group, a dicyanopyridyl group, a trifluoromethylpyridyl group, a trifluoromethylpyridyl group, a bistrifluoromethylpyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a cyanophenylpyridyl group, a bipyridyl group, a terpyridyl group, a quinolyl group, a cyanoquinolyl group, a trifluoromethylquinolyl group, an isoquinolyl group, a cyanoisoquinolyl group, a trifluoromethylisoquinolyl group, a phenantrenyl group, anthryl group, a phenantrolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, or a spirofluorenyl group.

10. Ar in formula (1) １ The organic electronic element according to any one of claims 1 to 3, wherein the group is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

11. The ring A in formula (1) is one or more of the groups Y. ２ An organic electronic element according to any one of claims 1 to 3, wherein it is any of the following (A-1) to (A-17), which may be substituted with. (In formulas (A-1) to (A-17), Y ２ (where l represents the same substituent as above, and p represents 0, 1, or 2, and 0 ≤ l + p ≤ 4.) 12. A material for organic electronic devices containing a compound represented by the following formula (2). (In formula (2), Ar ２ R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R ２１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. ２ Y represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group is one or more groups selected from hydroxyl group, carboxyl group, formyl group, nitro group, fluoro group, chloro group, bromo group, iodine group, trifluoromethyl group, cyano group, carbon-oxygen double bond, carbon-sulfur double bond, aromatic hydrocarbon group having 6 to 20 carbon atoms, heteroaromatic group having 3 to 20 carbon atoms, and aliphatic hydrocarbon group having 1 to 15 carbon atoms. １ The aliphatic hydrocarbon group may be substituted with a , and the aliphatic hydrocarbon group may be linear, branched, or cyclic, where n represents 1, 2, or 3. Ring B represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms, and the aromatic hydrocarbon ring and the heteroaromatic ring may each be monocyclic, fused, or linked, and the linked ring may be bonded by a methylene group substituted with a trifluoromethyl group, and the aromatic hydrocarbon ring and the heteroaromatic ring may be one or more groups Y selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. ２ (The aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with one or more selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.) 13. The material for an organic electronic element according to claim 12, which is a material for a photoelectric conversion element.

14. The material for an organic electronic element according to claim 12, which is a material for an imaging photoelectric conversion element.

15. R in formula (2) above ２ However, the methylene group or ethylene group is one or more groups selected from hydroxyl groups, carboxyl groups, formyl groups, nitro groups, fluoro groups, chloro groups, bromo groups, iodo groups, trifluoromethyl groups, cyano groups, carbon-oxygen double bonds, carbon-sulfur double bonds, aromatic hydrocarbon groups having 6 to 20 carbon atoms, heteroaromatic groups having 3 to 20 carbon atoms, and aliphatic hydrocarbon groups having 1 to 15 carbon atoms. １ The material for an organic electronic device according to any one of claims 12 to 14, which may be substituted with 16. R in formula (2) above ２ The material for an organic electronic device according to claim 15, wherein the group is an unsubstituted methylene group or an unsubstituted ethylene group.

17. Ar in formula (2) ２ The material for an organic electronic device according to claim 12, wherein the group is a phenyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, phenantrenyl group, fluorenyl group, benzofluorenyl group, spirofluorenyl group, benzoquinolyl group, phenantrolyl group, anthryl group, acridyl group, cyano group, nitro group, fluoro group, trifluoromethyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, adamantyl group, or a group formed by a combination of multiple substituents thereof.

18. Ar in equation (2) above ２ The material for an organic electronic device according to claim 12, wherein the group is a phenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a fluorophenyl group, a difluorophenyl group, a perfluorophenyl group, a cyanophenyl group, a dicyanophenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, a cyanobiphenyl group, a dicyanobiphenyl group, a pyridylphenyl group, a pyridylbenzonitrile group, a pyridyl group, a cyanopyridyl group, a dicyanopyridyl group, a trifluoromethylpyridyl group, a trifluoromethylpyridyl group, a bistrifluoromethylpyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a cyanophenylpyridyl group, a bipyridyl group, a terpyridyl group, a quinolyl group, a cyanoquinolyl group, a trifluoromethylquinolyl group, an isoquinolyl group, a cyanoisoquinolyl group, a trifluoromethylisoquinolyl group, a phenantrenyl group, anthryl group, a phenantrolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, or a spirofluorenyl group.

19. Ar in formula (2) ２ The material for an organic electronic device according to claim 12, wherein the group is a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

20. The ring B in formula (2) is one or more of the groups Y ２ The material for an organic electronic device according to claim 12, which is any of the following (B-1) to (B-17) which may be substituted with. (In formulas (B-1) to (B-17), Y ２ (where l represents the same substituent as above, and p represents 0, 1, or 2, and 0 ≤ l + p ≤ 4.) 21. An imide compound represented by the following formula (3) or formula (4). (In formula (3), Ar ３ is R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R ３１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. ３ m represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be linear, branched, or cyclic, and m represents 1, 2, or 3. １ and T ２ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. (In formula (4), Ar ４ is R ４１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ４１ A heteroaromatic group having 3 to 30 carbon atoms that may be substituted, or an unsubstituted alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure, wherein the aromatic hydrocarbon group and the heteroaromatic group may each be monocyclic, fused, or linked rings, and the R ４１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ R represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. ４ m represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be linear, branched, or cyclic, and m represents 1, 2, or 3. ３ , T ４ , T ５ and T ６ Each of these independently represents a hydrogen atom, a hydroxyl group, a carboxyl group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. However, T ３ , T ４ , T ５ and T ６ However, all of them are hydrogen atoms, m=1, and R ４ When it is a methylene group, Ar ４ (This does not result in an unsubstituted 2-pyridyl group or an unsubstituted 2-pyradyl group.) 22. R in equation (3) above ３ Or R in notation (4) ４ The imide compound according to claim 21, wherein each is independently a methylene group or an ethylene group, and the methylene group and the ethylene group may be substituted with one or more groups selected from a hydroxyl group, a carboxyl group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

23. R in equation (3) above ３ Or R in formula (4) above ４ The imide compound according to claim 21, wherein each is independently an unsubstituted methylene group or an unsubstituted ethylene group.

24. R in equation (3) above ３ Or R in formula (4) above ４ The imide compound according to claim 21, wherein each is independently a methylene group substituted with a cyano group, a phenyl group, a cyanophenyl group, or a pyridyl group.

25. Ar in formula (3) ３ or Ar in formula (4) above ４ The imide compound according to any one of claims 21 to 24, wherein each of the groups is independently a phenyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a triazyl group, a naphthyl group, a quinolyl group, an isoquinolyl group, a phenantrenyl group, a fluorenyl group, a benzofluorenyl group, a spirofluorenyl group, a benzoquinolyl group, a phenantrolyl group, anthryl group, an acridyl group, a cyano group, a nitro group, a fluoro group, a trifluoromethyl group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-hexyl group, a cyclohexyl group, an adamantyl group, or a group formed by a combination of multiple substituents thereof.

26. Ar in formula (3) above ３ or Ar in formula (4) above ４ The imide compound according to any one of claims 21 to 24, wherein each of the following groups is independently a phenyl group, a trifluoromethylphenyl group, a bistrifluoromethylphenyl group, a fluorophenyl group, a difluorophenyl group, a perfluorophenyl group, a cyanophenyl group, a dicyanophenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, a cyanobiphenyl group, a dicyanobiphenyl group, a pyridylphenyl group, a pyridylbenzonitrile group, a pyridyl group, a cyanopyridyl group, a dicyanopyridyl group, a trifluoromethylpyridyl group, a trifluoromethylpyridyl group, a bistrifluoromethylpyridyl group, a methylpyridyl group, a dimethylpyridyl group, a phenylpyridyl group, a cyanophenylpyridyl group, a bipyridyl group, a terpyridyl group, a quinolyl group, a cyanoquinolyl group, a trifluoromethylquinolyl group, an isoquinolyl group, a cyanoisoquinolyl group, a trifluoromethylisoquinolyl group, a phenantrenyl group, anthryl group, a phenantrolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, or a spirofluorenyl group.

27. Ar in equation (3) above ３ or Ar in formula (4) above ４ The imide compound according to any one of claims 21 to 24, wherein each is independently a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

28. T in equation (3) above １ ~T ２ or T in formula (4) above ３ ~T ６ The imide compound according to claim 21, wherein the group is a hydrogen atom, a cyano group, a phenyl group, a pyridyl group, a quinolyl group, or a group formed by a combination of multiple substituents thereof.

Images