Organic electronic element, imide compound, and method for producing same

Abstract

[Problem] The present invention provides an organic electronic element and an imide compound that are capable of improving hole transport capability. [Solution] An organic electronic element comprising a first electrode, a second electrode, and an organic layer that is disposed between the first electrode and the second electrode, wherein the organic layer contains a compound that has a partial structure represented by formula (1).　[Chemical formula 1] (In formula (1), ring A represents an optionally substituted monocyclic or fused-ring aromatic hydrocarbon ring having 6 to 30 carbon atoms. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring, which may have a substituent.　Ar1 and Ar2 each independently represent a group which has 1 to 3 optionally substituted unsaturated 6-membered rings that are each composed of an element selected from the group consisting of hydrogen, carbon, and nitrogen (the unsaturated 6-membered rings may be a single ring, a linking ring, a fused ring, or a ring formed by linking and fusing), and Ar1 and Ar2 are different from each other. However, at least one of Ar1 and Ar2 is substituted with at least one group that is selected from among a cyano group and a trifluoromethyl group.)

Description

Organic electronic device, imide compound and method for producing the same

[0001] The present invention relates to an organic electronic device, an imide compound, and a method for producing the same.

[0002] Currently, active efforts are being made to create new high-performance devices using organic materials. In particular, research and development of organic electronic elements such as photoelectric conversion elements and organic EL elements is being actively conducted, and material and device designs are being developed to improve device performance. For example, photoelectric conversion elements used in video recording applications are required to quickly transport carriers (electrons and holes) generated in the light-receiving layer to the electrode in order to suppress the cause of image retention. Furthermore, organic EL elements are required to quickly transport carriers from the electrode to the light-emitting layer in order to suppress an increase in driving voltage. Thus, in order to improve device performance, high efficiency in the movement of carriers within the element is required.

[0003] As a compound for an electron transport material for an electrophotographic photoreceptor to achieve the above-mentioned properties, an imide compound is disclosed in Patent Document 1. However, even for the imide compound described in Patent Document 1, further improvement in performance is required in the field of organic electronic devices.

[0004] JP 2019-182789 A

[0005] The present invention provides an organic electronic device, an imide compound, and a method for producing the same, which can improve hole transport capability.

[0006] As a result of extensive research aimed at solving the above problems, the present inventors have found that a specific compound having an imide skeleton as a partial structure can improve the hole transport ability in organic electronic devices such as photoelectric conversion devices and organic EL devices, and have thus completed the present invention.

[0007] That is, the present invention includes the following aspects: [1] An organic electronic device including a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a structure represented by the following formula (1): In formula (1), ring A represents a monocyclic or fused aromatic hydrocarbon ring having 6 to 30 carbon atoms, which may have a substituent. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring, which may have a substituent. Ar １ and Ar ２ each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of elements selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a ring formed by linking and condensing rings), and Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of the ring A and the Ar is substituted with at least one group selected from a cyano group and a trifluoromethyl group. １ and the Ar ２wherein the substituents are each independently a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, or an alkyl group having 2 to 10 carbon atoms. [3] The organic electronic device according to [1] or [2], further comprising an absorption layer disposed between the first electrode and the second electrode. [4] The organic electronic device according to [3], wherein the absorption layer is a layer containing at least two organic components. [5] The organic electronic device according to [3] or [4], wherein the organic layer comprises a hole transport layer and a hole transport promoting layer containing a compound having a structure represented by formula (1), or comprises a layer comprising a mixture of a hole transport material and a compound having a structure represented by formula (1). [6] The organic electronic device according to [5], wherein the hole transport layer and the hole transport promoting layer are disposed adjacent to each other between the first electrode and the second electrode. [7] The organic electronic device according to any one of [1] to [6], wherein in the formula (1), the ring A is a benzene ring, a naphthalene ring, a phenylbenzene ring, a diphenylbenzene ring, a naphthylbenzene ring, a phenylnaphthalene ring, a pyridylnaphthalene ring, a pyridylbenzene ring, or a dipyridylbenzene ring, each of which may be substituted with a cyano group, a fluoro group, or a trifluoromethyl group. [8] The organic electronic device according to any one of [1] to [6], wherein in the formula (1), the Ar １ and the Ar ２ [9] The organic electronic device according to any one of [1] to [7], wherein each independently represents a group formed by linking, condensing, or linking and condensing 1 to 3 rings of one or more types selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, triazine, quinoline, quinoxaline, and quinazoline, which may have a substituent. １ is a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, and a cyano-trifluoromethylphenyl group, and said Ar ２is a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, a ditrifluoromethylphenyl group, a cyano-trifluoromethylphenyl group, a cyanobiphenyl group, a terphenyl group, a dicyanoterphenyl group, a naphthyl group, a cyanonaphthyl group, a phenanthryl group, a pyridyl group, a cyanopyridyl group, a trifluoromethylpyridyl group, a dicyanopyridyl group, a cyano-trifluoromethylpyridyl group, a diphenylpyridyl group, a terpyridyl group, a pyrazyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a diphenylpyrimidyl group, a diphenyltriazyl group, a dipyridyltriazyl group, a quinolyl group, a cyanoquinolyl group, a quinoxalinyl group, a cyanoquinoxalinyl group, a quinazolyl group, and a cyanoquinazolyl group.

[10] The organic electronic device according to any one of [1] to [9], wherein in the formula (1), the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[11] An imide compound represented by the following formula (1): In formula (1), ring A represents a monocyclic or fused aromatic hydrocarbon ring having 6 to 30 carbon atoms, which may have a substituent. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring, which may have a substituent. Ar １ and Ar ２ each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of elements selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a ring formed by linking and condensing rings), Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of Ar is substituted with at least one group selected from a cyano group and a trifluoromethyl group. １ is a phenyl group which may have a substituent, and Ar ２

[13] The imide compound according to

[11] , wherein the ring A, the Ar are a group having 1 to 3 unsaturated 6-membered rings composed of elements selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered rings may be monocyclic, linked rings, fused rings, or linked and fused rings). １ and the Ar ２ wherein the substituent is a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, or an alkyl group having 2 to 10 carbon atoms.

[14] The imide compound according to any of

[11] to

[13] , wherein in formula (1), the ring A is a benzene ring, a naphthalene ring, a phenylbenzene ring, a diphenylbenzene ring, a naphthylbenzene ring, a phenylnaphthalene ring, a pyridylnaphthalene ring, a pyridylbenzene ring, or a dipyridylbenzene ring, optionally substituted with a cyano group, a fluoro group, or a trifluoromethyl group.

[15] The imide compound according to any of

[11] to

[13] , wherein in formula (1), the Ar ２ is a group in which 1 to 3 rings of one or more types selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, triazine, quinoline, quinoxaline, and quinazoline are linked, fused, or linked and fused.

[16] The imide compound according to any one of

[11] to

[14] . １ is a group selected from the group consisting of a phenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, and a 4-cyano-3-trifluoromethylphenyl group, and ２is a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, a 3,5-bis(4-cyanophenyl)phenyl group, a 4-trifluoromethylphenyl group, a 3,5-ditrifluoromethylphenyl group, a 4-cyano-3-trifluoromethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9-phenanthryl group, a 4-cyano-1-naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 3-cyano-4-pyridyl group, a 4-cyano-3-pyridyl group, a 4-cyano-2- The imide compound according to any one of

[11] to

[15] , wherein the ring A in formula (1) is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[18] The imide compound according to any one of

[11] to

[17] , wherein the ring A in formula (1) is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[19] The imide compound according to any one of

[11] to

[18] , wherein the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[20] The imide compound according to any one of

[11] to

[20] , wherein the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[21] The imide compound according to any one of

[11] to

[21] , wherein the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[22] The imide compound according to any one of

[11] to

[21] , wherein the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[23] The imide compound according to any one of

[11] to

[22] , wherein the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

[19] A method for producing an imide compound represented by the following formula (1), which comprises reacting a compound represented by the following formula (2) with an amine compound represented by the following formula (3): In formulas (1), (2), and (3), ring A represents a monocyclic or fused aromatic hydrocarbon ring having 6 to 30 carbon atoms, which may have a substituent. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring, which may have a substituent. Ar １ and Ar ２each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of elements selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a ring formed by linking and condensing rings), Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of the groups is substituted with at least one group selected from a cyano group and a trifluoromethyl group.

[0008] According to the present invention, it is possible to provide an organic electronic device, an imide compound, and a method for producing the same, which are capable of improving the hole transport capability.

[0009] 1 is a schematic cross-sectional view showing an example of a layer structure of a photoelectric conversion element according to the present invention, and FIG. 2 is a schematic cross-sectional view showing an example of a layer structure of an organic EL element according to the present invention.

[0010] (Organic Electronic Element) The organic electronic element of the present invention includes a photoelectric conversion element and an organic electroluminescent element (organic EL element). The photoelectric conversion element is an element that converts light energy into electrical energy or an electrical signal, and includes an imaging element, a photosensor, a solar cell, etc.

[0011] The organic electronic device of 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 contains a compound having a structure represented by the following formula (1) (hereinafter, also referred to as the compound represented by formula (1)):

[0012] The compound represented by formula (1) will be described in detail later. The organic layer preferably includes a hole transport layer and a hole transport promoting layer containing the compound represented by formula (1), or includes a layer formed by mixing a hole transport material with the compound represented by formula (1). Here, the hole transport layer has a role of transporting holes and contains a hole transport material. The hole transport promoting layer is disposed between the first electrode and the hole transport layer and has a role of facilitating the exchange of holes between the hole transport layer and the electrode and contains a hole transport promoting material. In the present invention, the compound represented by formula (1) can be used as a hole transport promoting material, although it is not particularly limited.

[0013] A preferred embodiment of the organic electronic device of the present invention is a photoelectric conversion device. The photoelectric conversion device 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. Hereinafter, the device configuration of the organic electronic device will be described using the photoelectric conversion device as an example.

[0014] <Configuration of 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 promotion layer. In the present invention, the compound represented by the above formula (1) can be used as the hole transport promotion material contained in the hole transport promotion 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 layers commonly used in photoelectric conversion elements. Examples include, but are not limited to, a light-receiving layer, an electron transport layer, a hole blocking layer, an electron blocking layer, and a buffer layer.

[0015] The photoelectric conversion element according to the present invention may have, for example, a first electrode, a hole transport promoting layer, a hole transport layer, and a second electrode laminated in this order, or a first electrode, a layer formed by mixing a hole transport material forming the hole transport layer with the compound represented by formula (1), and a second electrode laminated in this order. The photoelectric conversion element may also have, for example, the first electrode, the hole transport promoting layer, and the hole transport layer laminated adjacently in this order, or another layer such as a buffer layer may be interposed between the first electrode and the hole transport promoting layer or between the hole transport promoting layer and the hole transport layer.

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

[0017] The photoelectric conversion element may receive 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, the photoelectric conversion element may have a structure in which a transparent electrode (second electrode), an electron transport layer, a light-receiving layer, a hole transport layer, a hole transport promotion layer, and a metal electrode (first electrode) are stacked in this order, or a structure in which a transparent electrode (first electrode), a hole transport promotion layer, a hole transport layer, a light-receiving layer, an electron transport layer, and a metal electrode (second electrode) are stacked in this order. Furthermore, both the first electrode and the second electrode may be transparent electrodes.

[0018] Next, the case where the organic electronic element is an organic EL element will be described.

[0019] <Structure of Organic EL Element> 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, the 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. Examples of the other layers include layers commonly used in organic EL elements. Examples include, but are not limited to, a light-emitting layer, an electron transport layer, a hole-blocking layer, an electron-blocking layer, and a buffer layer.

[0020] The organic EL device according to the present invention may have, for example, a first electrode, a hole injection layer, a hole transport layer, and a second electrode laminated in this order, or a first electrode, a layer formed by mixing a hole transport material forming the hole transport layer with the compound represented by formula (1), and a second electrode laminated in this order. The organic EL device may also have, for example, the first electrode, the hole injection layer, and the hole transport layer laminated adjacently in this order, or another layer 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 device according to the present invention comprises a first electrode, a hole injection layer, a hole transport layer, an emitting layer, and a second electrode stacked in this order. In another embodiment, the organic EL device according to the present invention comprises a first electrode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and a second electrode stacked in this order. The layers may be stacked adjacent to each other, or another layer may be interposed between any of the 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, the organic EL element may have a structure in which a transparent electrode (second electrode), an electron transport layer, an emitting layer, a hole transport layer, a hole injection layer, and a metal electrode (first electrode) are laminated in this order, or a structure in which a transparent electrode (first electrode), a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and a metal electrode (second electrode) are laminated in this order. Furthermore, both the first electrode and the second electrode may be transparent electrodes.

[0023] Next, the compound represented by formula (1) in the organic electronic device of the present invention will be described.

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

[0025]

[0026] In formula (1), ring A represents a monocyclic or fused aromatic hydrocarbon ring having 6 to 30 carbon atoms, which may have a substituent. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring, which may have a substituent. １ and Ar ２ each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of elements selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a ring formed by linking and condensing rings), Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of these is substituted with at least one group selected from a cyano group and a trifluoromethyl group.

[0027] Ar in the imide compound represented by formula (1) １ and Ar ２ are different from each other. "Different" means that Ar １ and Ar ２ The difference between Ar and Ar is １and Ar ２ The types and numbers of the substituents contained in the groups represented by Ar may be the same and only the positions of the substituents may be different. １ and Ar ２ In this way, in the compound having the structure represented by formula (1), it is preferable that the number or type of the substituents contained in the group represented by formula (1), or the number and type of the substituents contained in the group represented by formula (1), are different from each other. １ and Ar ２ When the substituents are different, the cohesive force between molecules is reduced, and the surface of the film formed by vacuum deposition or the like is smoothed, which makes it easier to improve the hole transport ability.

[0028] Ar １ and Ar ２ Examples of Ar include groups each independently having 1 to 3 unsaturated 6-membered rings of one or more kinds. １ In terms of excellent device performance, it is preferable that the unsaturated 6-membered ring is a group having 1 or 2 of the above, and more preferably a group having 1. ２ The unsaturated 6-membered ring is preferably a group having 1 to 3 rings, more preferably a group having 1 ring. The unsaturated 6-membered ring may be a monocyclic ring, a linked ring, a condensed ring, or a ring formed by linking and condensing rings, and a monocyclic ring is preferred from the viewpoint of ease of synthesis.

[0029] The "unsaturated six-membered ring" may be any organic compound containing a double bond or triple bond between the constituent elements of the ring, and the type is not limited. The unsaturated six-membered ring is preferably composed of one or more elements selected from the group consisting of hydrogen, carbon, and nitrogen, in terms of ease of synthesis and excellent device performance. When nitrogen is included as a constituent element of the unsaturated six-membered ring, the number of nitrogen atoms per ring is preferably one to two, and more preferably one, in terms of excellent device performance. Furthermore, the unsaturated six-membered ring is preferably one or more rings selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, triazine, quinoline, quinoxaline, and quinazoline, in terms of excellent device performance, and benzene, pyridine, or quinoline is particularly preferred.

[0030] Ar １ and Ar ２At least one of Ar is substituted with at least one group selected from a cyano group and a trifluoromethyl group. １ , and Ar ２ The substituents in each independently include a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, or an alkyl group having 2 to 10 carbon atoms. １ The substituent of Ar is preferably an unsaturated 6-membered ring substituted with at least one group selected from the group consisting of a cyano group, a fluoro group, a trifluoromethyl group, and a cyanoalkyl group having 2 to 10 carbon atoms, and Ar ２ The substituent of Ar is preferably an unsaturated 6-membered ring substituted with at least one group selected from the group consisting of a cyano group, a fluoro group, a trifluoromethyl group, and a cyanoalkyl group having 2 to 10 carbon atoms. １ , and Ar ２ As the substituent in the above, a cyano group or a fluoro group is more preferable, and a cyano group is particularly preferable, in terms of excellent device performance.

[0031] Ar １ and Ar ２ are each independently preferably a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, a ditrifluoromethylphenyl group, a cyano-trifluoromethylphenyl group, a cyanobiphenyl group, a terphenyl group, a dicyanoterphenyl group, a naphthyl group, a cyanonaphthyl group, a phenanthryl group, a pyridyl group, a cyanopyridyl group, a trifluoromethylpyridyl group, a dicyanopyridyl group, a cyano-trifluoromethylpyridyl group, a diphenylpyridyl group, a terpyridyl group, a pyrazyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a diphenylpyrimidyl group, a diphenyltriazyl group, a dipyridyltriazyl group, a quinolyl group, a cyanoquinolyl group, a quinoxalinyl group, a cyanoquinoxalinyl group, a quinazolyl group and a cyanoquinazolyl group.

[0032] In addition, Ar１ is a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, and a cyano-trifluoromethylphenyl group, and Ar ２ is preferably a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, a ditrifluoromethylphenyl group, a cyano-trifluoromethylphenyl group, a cyanobiphenyl group, a terphenyl group, a dicyanoterphenyl group, a naphthyl group, a cyanonaphthyl group, a phenanthryl group, a pyridyl group, a cyanopyridyl group, a trifluoromethylpyridyl group, a dicyanopyridyl group, a cyano-trifluoromethylpyridyl group, a diphenylpyridyl group, a terpyridyl group, a pyrazyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a diphenylpyrimidyl group, a diphenyltriazyl group, a dipyridyltriazyl group, a quinolyl group, a cyanoquinolyl group, a quinoxalinyl group, a cyanoquinoxalinyl group, a quinazolyl group and a cyanoquinazolyl group, and in terms of excellent device performance, Ar １ is a group selected from the group consisting of phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 3,4-dicyanophenyl, 3,5-dicyanophenyl, and 4-cyano-3-trifluoromethylphenyl, and Ar ２means a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, a 3,5-bis(4-cyanophenyl)phenyl group, a 4-trifluoromethylphenyl group, a 3,5-ditrifluoromethylphenyl group, a 4-cyano-3-trifluoromethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9-phenanthryl group, a 4-cyano-1-naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 3-cyano-4-pyridyl group, a 4-cyano-3-pyridyl group, More preferably, it is a group selected from the group consisting of a 4-cyano-2-pyridyl group, a 3-trifluoromethyl-4-pyridyl group, a 3,5-dicyano-4-pyridyl group, a 4-cyano-5-trifluoromethyl-2-pyridyl group, a 3,5-diphenyl-4-pyridyl group, a 3,5-bis(4-cyanophenyl)-4-pyridyl group, a 3,5-bis(4-pyridyl)-4-pyridyl group, an m-terphenyl-5'-yl group, a 4,6-diphenylpyrimidin-2-yl group, a 4,6-diphenyl-1,3,5-triazin-2-yl group, and a 4-quinolyl group.

[0033] Examples of the monocyclic or fused aromatic hydrocarbon ring having 6 to 30 carbon atoms in Ring A include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a triphenylene ring, a tetracene ring, a chrysene ring, and a fluorene ring. Examples of the linking group include -O-, -S-, -C(=O)-, and -C(-R) ２ -. Examples of R include a methyl group, a trifluoromethyl group, a phenyl group, and a pyridyl group. When R is a phenyl group, the phenyl groups may be bonded to each other to form a fluorene ring. Examples of other aromatic hydrocarbon rings include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a triphenylene ring, a tetracene ring, a chrysene ring, and a fluorene ring. Examples of heteroaromatic rings include a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a thiophene ring, a furan ring, a benzothiophene ring, a benzofuran ring, a dibenzothiophene ring, a dibenzofuran ring, a pyrrole ring, an indole ring, and a carbazole ring.

[0034] Examples of ring A in formula (1) include the following (A1) to (A16).

[0035]

[0036] Of the above (A1) to (A16), (A1), (A2), (A3), (A4), (A5), (A6), (A14), and (A16) are preferred, with (A1), (A2), (A5), (A6), and (A16) being more preferred in terms of having sufficient acceptor properties and expected performance. Furthermore, (A1) and (A2) are preferred in terms of easy availability of raw materials, and (A2) is more preferred in terms of ease of synthesis. When ring A in formula (1) is represented by the above formula (A1), the imide compound of the present invention is represented, for example, by formula (1a) below. When ring A is represented by the above formula (A2), the imide compound of the present invention is represented, for example, by formula (1b) or formula (1c) below. In formula (1a), formula (1b), and formula (1c), R １ ~R １０ each independently represents a hydrogen atom or a substituent.

[0037] Examples of the substituent in ring A include a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, and an alkyl group having 2 to 10 carbon atoms.

[0038] From the viewpoint of excellent device performance, ring A is preferably a benzene ring, a naphthalene ring, a phenylbenzene ring, a diphenylbenzene ring, a naphthylbenzene ring, a phenylnaphthalene ring, a pyridylnaphthalene ring, a pyridylbenzene ring, or a dipyridylbenzene ring, which may be substituted with a cyano group, a fluoro group, or a trifluoromethyl group. In particular, from the viewpoint of ease of synthesis, ring A is more preferably a ring other than a naphthalene ring substituted with a cyano group. Furthermore, from the viewpoint of excellent device performance, when ring A is a benzene ring substituted with a fluoroalkyl group, Ar １ and Ar ２ It is more preferred that both of are other than a phenyl group.

[0039] Examples of cyanoalkyl groups having 2 to 10 carbon atoms include a cyanomethyl group, a dicyanomethyl group, a tricyanomethyl group, a cyanoethyl group, a dicyanoethyl group, a tricyanoethyl group, a tetracyanoethyl group, a percyanoethyl group, a cyanopropyl group, a percyanopropyl group, a percyanobutyl group, a percyanopentyl group, a percyanohexyl group, a percyanoheptyl group, and a percyanooctyl group.

[0040] Examples of the fluoroalkyl group having 1 to 10 carbon atoms include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a difluoroethyl group, a trifluoroethyl group, a tetrafluoroethyl group, a perfluoroethyl group, a fluoropropyl group, a perfluoropropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, and a perfluorooctyl group.

[0041] Examples of the fluoroalkoxy group having 1 to 10 carbon atoms include a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a fluoroethoxy group, a difluoroethoxy group, a trifluoroethoxy group, a tetrafluoroethoxy group, a perfluoroethoxy group, a fluoropropoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a perfluoropentyloxy group, a perfluorohexyloxy group, a perfluoroheptyloxy group, and a perfluorooctyloxy group.

[0042] The organic electronic element of the present invention is not particularly limited, but examples thereof include an organic EL element and a photoelectric conversion element (such as a solar cell, a photodiode, or a photoelectric conversion element for an imaging element). As the organic electronic element, a photoelectric conversion element is preferred, and a photoelectric conversion element for an imaging element is more preferred.

[0043] The compound represented by formula (1) is used as a part of an organic electronic device. The part of the organic electronic device is not particularly limited, but examples thereof include an electron transport layer, a light-emitting layer, a light-receiving layer, a hole injection layer, and a hole transport promotion layer. Among these, the compound represented by formula (1) is preferably used in the hole transport promotion layer.

[0044] Preferable examples of the imide compound represented by formula (1) include the following (B1) to (B210) and (C1) to (C150), although the compound of the present invention is not limited thereto.

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068] Among the above, (B2), (B3), (B4), (B7), (B8), (B9), (B12), (B15), (B16), (B17), (B 18), (B19), (B20), (B21), (B23), (B24), (B27), (B28), (B29), (B31), (B34 ), (B36), (B38), (B39), (B40), (B43), (B44), (B45), (B47), (B48), (B49), (B50), (B61), (B67), (B69), (B72), (B73), (B74), (B75), (B78), (B85), (B9 1), (B99), (B103), (B110), (B116), (B151), (B153), (B155), (B155), (B16 0), (B164), (B165), (B166), (B169), (B170), (B172), (B173), (B177), (B1 78), (B181), (B184), (B189), (B190), (B193), (B200), (B201), (B202), (B 205), (B206), (B207), (B208), (B209), (C1), (C3), (C10), (C16), (C19), (C (B2), (B3), (B4), (B7), (B9), (B12), (B15), (B17), (B18), (B19), (B20), (B23), (B24), (B28), (B29), (B31), (B36), (B38), (B39), (B40), (B43), (B44), (B47), (B48), (B49), (B50), (B61), (B67), (B69), (B72), (B73), (B74), (B75), (B78), (B91), ( B99), (B110), (B151), (B153), (B155), (B160), (B164), (B165), (B166), (B169), (B170), (B172), (B173), (B177), (B178), (B181), (B184), (B189), (B190), (B193), (B200), (B201), (B202), (B205), (B206), (B207), (B208), (B209), (C1), (C3), and (C148) are more preferred, and (B2), (B3), (B4), (B7), (B9), and (B12) are more preferred.(B15), (B17), (B18), (B19), (B23), (B24), (B28), (B31), (B39), (B43), (B44), (B47), (B48), (B72), (B73), (B74), (B151), (B153), (B155), (B160), (B164), (B165), (B166), (B169), (B170), (B172), (B173), (B178), (B181), (B184), (B189), (B200), (B201), (B202), (B207), (C3), and (C148) are more preferred.

[0069] [Production Method] The compound represented by formula (1) can be synthesized by a known method or a combination thereof. For example, a tetracarboxylic dianhydride represented by formula (4) below is reacted with an amine compound represented by formula (5) below to obtain a compound represented by formula (2) below (Step 1). The obtained compound represented by formula (2) below is then reacted with an amine compound represented by formula (3) below to synthesize an imide compound represented by formula (1) (Step 2). The imide compound represented by formula (1) can be synthesized in two steps (Steps 1 and 2) as described above, or in one step.

[0070] (In the formula, Ar １ , Ar ２ and ring A have the same definition as in formula (1).

[0071] The compound represented by the above formula (2) or the imide compound represented by (1) can be synthesized by referring to, for example, known methods (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.).

[0072] The reaction in Step 1 and Step 2 may be carried out in a reaction solvent. Preferred examples of the reaction solvent 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 suitable 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 solvents may be used alone or in any combination, and there are no particular limitations on the amount of solvent used. Among these, DMF, DMAc, pyridine, quinoline, and mixed solvents thereof are preferred in terms of their good reaction yield.

[0073] The reaction can be accelerated by carrying out the reaction in steps 1 and 2 in the presence of a condensing agent. Examples of the condensing agent include solid acids such as alumina and silica gel; metal chlorides such as titanium tetrachloride, tin tetrachloride, and antimony pentachloride; organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, diazabicycloundecene, tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane; and carbodiimides such as 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, and 1,1'-carbonyldi(1,2,4-triazole). Among these, triethylamine, pyridine, or EDC is more preferred as the condensing agent used in step 1, as it provides a good reaction yield of the compound represented by formula (2).Furthermore, an organic base is preferred as the condensing agent used in step 2, as it provides a good reaction yield of the imide compound represented by formula (1), and 1,4-diazabicyclo[2.2.2]octane is more preferred.

[0074] The amount of the condensing agent used is preferably 0.1 to 10 times by mole, more preferably 0.5 to 5 times by mole, per mole of the compound represented by formula (2) or the tetracarboxylic dianhydride represented by formula (4). The amount of the amine compound represented by formula (3) used is preferably 1.0 to 1.2 times by mole, per mole of the compound represented by formula (2), in terms of reaction yield and production efficiency. The amount of the amine compound represented by formula (5) used is preferably 0.3 to 1.5 times by mole, more preferably 0.5 to 1.1 times by mole, per mole of the tetracarboxylic dianhydride represented by formula (4). The reactions in steps 1 and 2 can be carried out in the presence of a moisture scavenger. Examples of moisture scavengers include synthetic crystalline zeolites such as molecular sieves; dried silicas such as silica gel; and organic silanes such as trimethoxyvinylsilane and triethoxyvinylsilane. Among these, organic silanes are preferred due to their high reaction yield, with triethoxyvinylsilane being more preferred. The amount of the moisture scavenger used is preferably in the range of 0.1 to 30 times by mole, more preferably 0.5 to 15 times by mole, per mole of the compound represented by formula (2) or the tetracarboxylic dianhydride represented by formula (4).

[0075] The reaction temperature and reaction time vary depending on the amounts of the 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 allows the reaction to proceed sufficiently, and a reaction temperature of 180°C or lower is economically preferable, and the reaction time is preferably in the range of 1 to 24 hours.

[0076] <<Action and Effect of the Compound Represented by Formula (1)>> The compound represented by formula (1) has a naphthalenetetracarboxylic acid diimide skeleton or a specific skeleton structure similar thereto, and therefore this strong acceptor skeleton is expected to have a strong interaction with the HOMO orbital of the hole transport material. In other words, when a layer (e.g., a hole transport promotion layer) in an organic electronic device (e.g., a photoelectric conversion device) contains a compound represented by formula (1), it is expected that the interaction with the HOMO orbital of an adjacent hole transport layer will be enhanced, and carrier exchange between the hole transport layer and the hole transport promotion layer will be promoted. In this way, the compound represented by formula (1) has an extremely deep LUMO level, and therefore it is expected that the exchange of holes between the hole transport layer and the electrode will be smooth. Furthermore, since the compound represented by formula (1) has a naphthalenetetracarboxylic acid diimide skeleton or a specific skeleton structure similar thereto, thermal stability, high reduction resistance, etc. can also be expected. In addition, since the compound represented by formula (1) has different substituents on the left and right sides of the imide skeleton, it is expected to have a strong interaction with the hole transport material, which is expected to facilitate smoother exchange of holes between the hole transport layer and the electrode. It is also expected to smooth the surface of films formed by vacuum deposition or the like.

[0077] As described above, the present inventors have found that the compound represented by formula (1) can be effectively used as a hole transport promoting material that facilitates the exchange of holes between a hole transport layer and an electrode. They have confirmed that, in a photoelectric conversion element, the hole transport ability is promoted when the compound represented by formula (1) (hole transport promoting material) is combined with a hole transport material. That is, they have confirmed that, in a photoelectric conversion element, the energy barrier when carriers generated in the light-receiving layer are extracted to the electrode side can be reduced by the compound represented by formula (1), which is the hole transport promoting material of the present invention.

[0078] <Embodiments> Examples of the laminate structure of the organic electronic element (e.g., photoelectric conversion element) of the present invention include the following structures (i) and (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 When the organic electronic element is, for example, an organic EL element, the "light-receiving layer" in the structure (i) or (ii) can be read as the "light-emitting layer".

[0079] The photoelectric conversion element and organic EL element according to the present invention will be described in more detail below, taking the above-mentioned configuration (ii) as an example, with reference to Fig. 1 and Fig. 2. Fig. 1 is a schematic cross-sectional view showing an example of the layered configuration of the photoelectric conversion element according to the present invention, and Fig. 2 is a schematic cross-sectional view showing an example of the organic EL element according to the present invention.

[0080] <<First Embodiment>> A photoelectric conversion element according to a first embodiment is an organic imaging element or photosensor having the layered structure shown in Fig. 1. The photoelectric conversion element 1 includes a first electrode 11 (first electrode), a hole transport promotion 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.

[0081] In the photoelectric conversion element 1 shown in FIG. 1 , light is incident from above the transparent first electrode 11 and is received by the light-receiving layer 14. For convenience, FIG. 1 illustrates light as being incident from the side of the light-receiving layer 14. Furthermore, a voltage is applied to the photoelectric conversion element 1 so that, of the charges (holes and electrons) generated by photoelectric conversion in the light-receiving layer 14, the holes are moved to the first electrode 11 and the electrons are moved to the second electrode 16. That is, the first electrode 11 serves as a hole-collecting electrode, and the second electrode 16 serves as an electron-collecting electrode. Note that FIG. 1 does not illustrate the substrate provided on the top surface of the first electrode 11. The substrate here is not particularly limited, and examples include a glass plate, a quartz plate, and a plastic plate. Furthermore, in a configuration in which light is incident from the substrate side, the substrate is transparent to the wavelength of light. Each of the above layers will be described below.

[0082] [First electrode 11] A first electrode 11 or a second electrode 16 is provided on a substrate. In the case of a photoelectric conversion element configured so that light passes through the first electrode 11 and enters 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.

[0083] The transparent material used for the first electrode 11 or the second electrode 16 is not particularly limited, but examples thereof 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.

[0084] In the case of a photoelectric conversion element configured so that light enters the light-receiving layer 14 only from the second electrode 16 side, the transmittance 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, and platinum.

[0085] [Hole Transport Promotion Layer 12] The hole transport promotion layer 12 is provided between the first electrode 11 and the hole transport layer 13 described below. The hole transport promotion layer 12 is provided to promote hole transport from the hole transport layer 13 to the first electrode 11. The hole transport promotion layer 12 contains the compound represented by formula (1) above. The hole transport promotion layer 12 may also contain a compound other than the compound represented by formula (1). Examples of compounds that can be contained in the hole transport promotion layer 12 include conventionally known hole transport materials, such as the compounds used in the hole transport layer 13 described below.

[0086] [Hole Transport Layer 13] The hole transport layer 13 is provided between the hole transport promotion layer 12 and the light-receiving layer 14. The hole transport layer 13 has a role of transporting holes generated in the light-receiving layer 14 from the light-receiving layer 14 to the first electrode 11, and a role of blocking electrons generated in the light-receiving layer 14 from moving toward the first electrode 11. Depending on the application, the hole transport layer 13 may also have a role of blocking electron injection from the first electrode 11.

[0087] The hole transport layer 13 may have a single layer structure made of one or more materials, or may have a laminate 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, benzodifuran compounds, benzodithiophene compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds. Among these, fluorene compounds, carbazole compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, indolocarbazole compounds, etc. are preferred, and fluorene compounds, carbazole compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds are particularly preferred.

[0088] [Light-receiving layer 14] The light-receiving layer 14 is provided between the hole-transporting layer 13 and the electron-transporting layer 15 described below. Examples of materials for the light-receiving layer 14 include materials having a photoelectric conversion function.

[0089] The absorption layer 14 may have a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions. In particular, in order to increase the photoelectric conversion efficiency, the absorption layer is preferably made of a layer containing at least two materials (organic components).

[0090] Examples of materials used for the light-receiving layer 14, which has a single-layer structure made of one material, include (i) coumarin and its derivatives, quinacridone and its derivatives, and phthalocyanine and its derivatives. Examples of materials used for the light-receiving layer 14, which has a single-layer structure made of two materials, include the aforementioned combinations of (i) coumarin and its derivatives, quinacridone and its derivatives, and phthalocyanine and its derivatives with (ii) fullerene and its derivatives and other acceptor materials. The light-receiving layer 4 made of these materials may be formed by vapor deposition of a premixed powder, or by co-evaporation in any ratio. Examples of materials used for the light-receiving layer 14, which has a single-layer structure made of three materials, include the aforementioned combinations of (i) coumarin and its derivatives, quinacridone and its derivatives, and phthalocyanine and its derivatives with (ii) fullerene and its derivatives and other acceptor materials, and (iii) hole-transport materials. The light-receiving layer 14 made of these materials may be formed by depositing a mixture of powders in advance, or by co-depositing the materials in any ratio.

[0091] (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 include the same compounds as those used in the hole transport layer 13 described above.

[0092] Furthermore, the material having a photoelectric conversion function is not limited to being contained only in the light-receiving layer 14. For example, the material having a photoelectric conversion function may be contained in a layer adjacent to the light-receiving layer 14 (hole transport layer 13 or electron transport layer 15).

[0093] [Electron Transport Layer 15] The electron transport layer 15 is provided between the light-receiving layer 14 and the second electrode 16 described below. The electron transport layer 15 has a role of transporting electrons generated in the light-receiving layer 14 to the second electrode 16 and a role of blocking the movement of holes from the second electrode 16, to which the electrons have been transported, to the light-receiving layer 14. Depending on the application, the electron transport layer 15 may also have a role of blocking hole injection from the second electrode 16.

[0094] The electron transport material that can be contained in the electron transport layer 15 may be a known electron transport material. Examples of the electron transport material include fullerene, fullerene derivatives, triazine derivatives, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), and Bp hen(4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum), 4,6-bis(3,5-di(pyridin-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.

[0095] The electron transport layer 15 may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0096] [Second Electrode 16] A second electrode 16 is provided on the electron transport layer 15. Examples of materials for the second electrode 16 include indium-tin oxide (ITO), indium-zinc oxide (IZO), sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium / copper mixture, a magnesium / silver mixture, a magnesium / aluminum mixture, a magnesium / indium mixture, and aluminum / aluminum oxide (Al ２ O ３ ) mixture, indium, lithium / aluminum mixture, gold, platinum, rare earth metals, molybdenum oxide, etc. The first electrode 11 and the second electrode 16 may be the same or different.

[0097] [Method of Forming Each Layer] Each layer except for the first electrode 11 and the second electrode 16 described above can be formed by thinning the material of each layer (together with a material such as a binder resin and a solvent, if necessary) by a known method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc. There are no particular restrictions on the film thickness of each layer formed in this manner and it can be selected appropriately depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0098] The first electrode 11 and the second electrode 16 can be formed by thinning an electrode material by a method such as vapor deposition or sputtering. A pattern may be formed through a mask of a desired shape during vapor deposition or sputtering, or a pattern of a desired shape may be formed by photolithography after forming a thin film by vapor deposition or sputtering.

[0099] The film thickness of the first electrode 11 and the second electrode 16 is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0100] The materials constituting the first electrode 11 and the second electrode 16 may be interchanged as necessary (also called an inverted structure). In such a structure, a photoelectric conversion element is formed in which light passes through the second electrode 16 and enters the light-receiving layer 14.

[0101] An imaging element including the photoelectric conversion element of this embodiment can be applied to, for example, an imaging element of a digital camera or a digital video camera, and an imaging element built into a mobile phone, etc. An optical sensor can be applied to, for example, a television remote control, an air conditioner switch, an automatic door opener, etc.

[0102] <<Second Embodiment>> A photoelectric conversion element according to a second embodiment of the present invention is a solar cell having the layered structure shown in Fig. 1. In the solar cell 1, a hole transport promotion layer 12 and a hole transport layer 13 are provided between a first electrode 11 and a light-receiving layer 14, and an electron transport layer 15 is provided between a second electrode 16 and the light-receiving layer 14. However, some of these layers may be omitted, or conversely, other layers may be added.

[0103] [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).

[0104] [Hole Transport Promotion Layer 12] The material of the hole transport promotion layer 12 is the same as the material of the hole transport promotion layer 12 in the first embodiment (the compound represented by formula (1)). The material of the hole transport promotion layer 12 may contain a conventionally known hole transport material in addition to the material in the first embodiment.

[0105] [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. The material of the hole transport layer 13 may contain a conventionally known hole transport material in addition to the hole transport material in the first embodiment.

[0106] [Light-Receiving Layer 14] The light-receiving layer 14 may be made of an electron-donating material and an electron-accepting material. This may be a planar bond type in which the electron-donating material and the electron-accepting material are bonded to each other at their respective planes, or a bulk heterobond 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 polymeric compounds and copolymers thereof, such as polythiophene derivatives, polyfluorene derivatives, and polyphenylene vinylene derivatives, as well as 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 be an inorganic semiconductor in addition to an organic semiconductor, provided that the effects of the present invention are not impaired. 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.

[0107] [Electron Transport Layer 15] The electron transport material in the first embodiment can be used as the material for the electron transport layer 15. Alternatively, the electron transport material may be an alkali metal halide such as sodium fluoride or cesium fluoride, an alkaline earth metal halide such as calcium fluoride, a carbonate such as cesium carbonate, or an inorganic n-type semiconductor such as titanium oxide or zinc oxide.

[0108] [Second Electrode 16] The second electrode 16 may be made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof, but is not limited to these.

[0109] The materials constituting the first electrode 11 and the second electrode 16 may be interchanged as necessary (also called an inverted structure). In such a structure, a photoelectric conversion element is formed in which light passes through the second electrode 16 and enters the light-receiving layer 14.

[0110] [Method of Forming Each Layer] The method of forming each layer is not particularly limited. For example, the first electrode 11, the hole transport promotion layer 12, the hole transport layer 13, the light-receiving layer 14, the electron transport layer 15, and the second electrode 16 may be sequentially laminated on a substrate using a vapor deposition method, a spin coating method, a casting method, a pattern transfer method, or the like. Alternatively, the hole transport promotion layer 12, the hole transport layer 13, the light-receiving layer 14, and the electron transport layer 15 may be laminated, and then the first electrode 11 and the second electrode 16 may be formed on this laminate by transfer, vapor deposition, sputtering, or the like.

[0111] <<Third Embodiment>> An organic electronic element according to a third embodiment of the present invention is an organic EL element having the layered structure shown in Fig. 2. That is, the organic EL element 2 has 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 provided in this order. However, some of these layers may be omitted, or other layers may be added.

[0112] [First Electrode 21] The first electrode 21 has a role of injecting holes from the hole transport layer to the light emitting layer. As the first electrode 21, a transparent electrode such as indium tin oxide (ITO), indium zinc oxide (IZO), gold, silver, platinum, copper, or the like, a metal or alloy such as aluminum, molybdenum, chromium, nickel, a polythiophene derivative having high charge transportability, a polyaniline derivative, or the like can be used, but is not limited to these.

[0113] The organic electronic element may emit light from either the first electrode 21 or the second electrode 26, or from both the first and second electrodes 21 and 26. The electrode from which light is extracted is made of a transparent material such as ITO or IZO. For convenience, FIG. 2 shows light emitted from the side of the light-emitting layer 24.

[0114] [Hole injection layer 22] The hole injection layer 22 is provided between the first electrode 21 and the hole transport layer 23 described below. 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 the above formula (1) as a hole injection material. The hole injection layer 22 may also contain compounds other than the compound represented by the above formula (1). Examples of compounds that can be contained in the hole injection layer 22 include conventionally known hole transport materials.

[0115] [Hole Transport Layer 23] The hole transport layer 23 is provided between the hole injection layer 22 and the light-emitting layer 24. The hole transport layer 23 has a role of transporting holes injected from the first electrode 21 to the light-emitting layer 24. The hole transport layer 23 may have a single-layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same composition 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.

[0116] [Light-emitting layer 24] The light-emitting layer 24 has a role of generating light emission (phosphorescence or fluorescence) through recombination of holes injected from the first electrode 21 and electrons injected from the second electrode 26, and contains a light-emitting material and, if necessary, a light-emitting host material. The light-emitting material and the light-emitting host material can be appropriately selected from known materials. Examples of the light-emitting material and the light-emitting host material include carbon-fused ring dyes such as triazine derivatives (including TADF materials substituted with carbazole or the like), pyrimidine derivatives, carbazole derivatives, anthracene derivatives, tetracene derivatives, pyrene derivatives, rubrene derivatives, and decacyclene derivatives; perylene derivatives such as perylene diimide; xanthene dyes such as rhodamine B; cyanine dyes; coumarin dyes such as coumarin 6 and C545T; quinacridone dyes such as Qd4 and DEQ; squarylium dyes; styryl dyes; pyrazolone derivatives; phenoxazone dyes such as NileRed; carbazole; triarylamine; and tris(2-phenylpyridine). Examples of suitable metal complexes include, but are not limited to, iridium complexes such as iridium(III) (Ir(ppy)), tris[2-phenyl-4-(2-ethylcyclohexyloxy)pyridine]iridium(III) (Ir(ehppy)), aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrin zinc complexes, europium complexes, and metal complexes composed of a central metal such as Al, Zn, Be, or a rare earth metal such as Tb, Eu, or Dy, and a ligand such as an oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, or quinoline structure.

[0117] [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. Examples of the electron transport material include, but are not limited to, triazine derivatives, tris(8-quinolinolato)aluminum (Alq), bis(2-methyl-8-quinolinolato)-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), bathocuproine (BCP), and silole derivatives.

[0118] [Second Electrode 26] The second electrode 26 has a role of injecting electrons from the electron transport layer 25 to the light-emitting layer 24. The second electrode 26 may be made of aluminum, a magnesium-silver alloy, an aluminum-lithium alloy, lithium, sodium, potassium, cesium, cesium-doped ITO, or the like, but is not limited to these.

[0119] [Method of Forming Each Layer] To form each layer of the organic EL element 2, for example, first, a thin film made of the material of the first electrode 21 is formed on a suitable light-transmitting substrate (not shown) by a method such as vapor deposition or sputtering. A hole injection layer 22 and a hole transport layer 23 are then formed on the first electrode 21 in this order. The hole injection layer 22 and the hole transport layer 23 can be formed by a method such as vacuum deposition, spin coating, casting, or the LB method. Next, an emissive layer 24 is provided on the hole transport layer 23. The emissive layer 24 can also be formed by forming a thin film of a desired organic emissive material by a method such as vacuum deposition, sputtering, spin coating, or 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 by a method such as vapor deposition or sputtering of a desired metal material. The method for forming each layer of the organic EL element is not limited to the above-mentioned methods, and any known method can be appropriately used, such as vacuum deposition, molecular beam deposition (MBE), dipping using a solution in which a material is dissolved in a solvent, spin coating, casting, bar coating, roll coating, or other coating methods.

[0120] The organic electronic device (e.g., photoelectric conversion device, organic EL device) of the present invention and the method for forming each layer of the device are not limited to the device and method described in the above-described embodiment. For example, the materials of the first electrode, light-receiving layer (or light-emitting layer), electron transport layer, and second electrode can be appropriately replaced with other known materials. Furthermore, the hole injection layer and hole transport layer can also be replaced with a layer formed by mixing the compound represented by formula (1) with a hole transport material.

[0121] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. １ Identification was based on H-NMR spectrum (400 MHz) or mass spectrometry. １ H-NMR spectra were measured using a Bruker ASCEND 400 (400 MHz; manufactured by BRUKER). １H-NMR spectra were obtained using deuterated chloroform (CDCl ３ ) or deuterated dimethyl sulfoxide (DMSO-d ６ ) was used as the measurement solvent, and tetramethylsilane (TMS) was used as the internal standard. Commercially available reagents were used. Mass spectrometry was performed using an ESI-Qq-TOF MS compact (manufactured by BRUKER).

[0122] (Synthesis reference example 1) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (10.6 g, 39.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.89 g, 15.1 mmol) were suspended in N,N-dimethylformamide (80 mL) and stirred at 120°C for 1 hour. Then, 4-aminobenzonitrile (2.95 g, 25.0 mmol) was added to the reaction solution, and the mixture was stirred at 120°C for 16 hours. After cooling to room temperature, low boiling points were distilled off, and water was added to the resulting suspension, and the precipitated solid was collected by filtration. The collected solid was extracted with hot chloroform, and the low boiling points were distilled off from the resulting filtrate. The resulting solid was suspended in acetic anhydride (10 mL) and heated with stirring at 120°C for 1 hour. After cooling to room temperature, the precipitated solid was collected by filtration to give 4-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isochromeno[6,5,4-def]isoquinolin-7-yl)benzonitrile (yield 1.50 g, 16%). １ H-NMR (CDCl ３ ) δ (ppm): 8.91-8.88 (m, 4H), 7.91 (d, J=8.6Hz, 2H), 7.49 (d, J=8.6Hz, 2H).

[0123] (Synthesis reference example 2) The same operation as in Reference Synthesis Example 1 was carried out, except that 3-aminobenzonitrile (2.95 g, 25.0 mmol) was used instead of 4-aminobenzonitrile (2.95 g, 25.0 mmol), to obtain 3-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isochromeno[6,5,4-def]isoquinolin-7-yl)benzonitrile (yield 1.40 g, 15%). １ H-NMR (DMSO-d６ ) δ (ppm): 8.78-8.69 (m, 4H), 8.03-7.98 (m, 2H), 7.88-7.77 (m, 2H).

[0124] (Synthesis reference example 3) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (15.0 g, 55.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.02 g, 21.0 mmol) were suspended in N,N-dimethylformamide (500 mL). After stirring this reaction solution at 120°C for 1 hour, 4-aminophthalonitrile (5.00 g, 34.9 mmol) was added and the mixture was stirred at 120°C for an additional 17 hours. After allowing to cool to room temperature, low boiling points were distilled off under reduced pressure, and water was added to the resulting suspension. The precipitated solid was collected by filtration, suspended in acetic anhydride (100 mL), and heated and stirred at 120°C for 1 hour. After allowing to cool to room temperature, the solid was filtered off, and water was added to the filtrate, and the precipitated solid was collected by filtration. The collected solid was purified by recrystallization from 1,4-dioxane to obtain the target compound, 4-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isochromeno[6,5,4-def]isoquinolin-7-yl)phthalonitrile (yield: 4.87 g, 35%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.77-8.70 (m, 4H), 8.40 (d, J = 8.3Hz, 1H), 8.32 (d, J = 1.9Hz, 1H), 8.10 (dd, J = 8.3, 1.9Hz, 1H).

[0125] (Synthesis reference example 4) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (5.99 g, 22.35 mmol), 5-amino-1,3-benzenedicarbonitrile (2.0 g, 13.97 mmol), and dicyclohexylcarbodiimide (3.18 g, 15.37 mmol) were suspended in N,N-dimethylformamide (140 mL) and stirred at 150°C for 6 hours. After cooling to room temperature, the precipitated solid was filtered off. Low-boiling components were distilled off from the obtained filtrate until the total volume was approximately two-thirds. A saturated aqueous solution of sodium bicarbonate (250 mL) was added dropwise to the remaining liquid under ice cooling, and the mixture was stirred at room temperature for 2 hours. Next, the precipitated solid was filtered off, and concentrated hydrochloric acid was added dropwise to the obtained filtrate under ice cooling until the pH reached 2. The precipitated solid was collected by filtration, and acetic anhydride was added. The mixture was stirred at 120°C for 2 hours, and the remaining solid was collected by filtration. The resulting solid was washed with hot 1,4-dioxane, and the remaining solid was filtered off. Low boiling points were removed from the filtrate, and the resulting solid was purified by recrystallization (1,4-dioxane) to give the target compound, 5-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isocumeno[6,5,4-def]isoquinolin-7-yl)-1,3-benzodicarbonitrile (yield: 860 mg, 16%). １ H-NMR (DMSO-D6) δ (ppm): 8.39 (d, J = 1.50 Hz, 2H), 8.67 (t, J = 1.5 Hz, 1H), 8.75 (m, 4H).

[0126] (Synthesis reference example 5) Under a nitrogen atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (10.0 g, 34.4 mmol) and 1-naphthylamine (3.10 g, 21.5 mmol) were dissolved in N,N-dimethylformamide (220 mL) and stirred at 120°C for 1 hour. After cooling to room temperature, crystallization was carried out and the resulting precipitate was collected by filtration. The resulting solid was suspended in saturated aqueous sodium bicarbonate (600 mL) and stirred overnight. Next, the solid was removed by filtration, and concentrated hydrochloric acid was added to the filtrate to adjust the pH to 2 or less, and the resulting precipitate was collected by filtration. The resulting solid was dried, suspended in acetic anhydride, and stirred at 120°C for 2 hours. Acetic acid was added to the heated suspension and heated, and the solid was removed by hot filtration, after which the low-boiling components of the filtrate were distilled off under reduced pressure. The resulting residue was subjected to Soxhlet extraction (solvent: chloroform) to obtain the target 7-(naphth-1-yl)-1H-isochromeno[6,5,4-def]isoquinoline-1,3,6,8(7H)-tetraone (yield: 1.04 g, 12%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.77 (d, J = 7.6 Hz, 2H), 8.72 (d, J = 7.6 Hz, 2H), 8.14-8.06 (m, 2H), 7.97 (d, J = 8.4 Hz, 1H), 7.71 (s , 1H), 7.69 (dd, J=10.5, 7.2Hz, 1H), 7.59 (ddd, J=8.1, 6.9, 1.1Hz, 1H), 7.47 (ddd, J=8.2, 6.8, 1.2Hz, 1H).

[0127] (Synthesis reference example 6) Under an argon atmosphere, pyromellitic anhydride (14.1 g, 64.5 mmol) and 4-amino-2-trifluorobenzonitrile (3.0 g, 16.1 mmol) were suspended in N,N-dimethylformamide (300 mL) and heated with stirring at 150°C for 16 hours. After allowing to cool to room temperature, low boiling points were distilled off until the reaction liquid was reduced to one-third of its original volume, and the precipitated solid was filtered off. Water was added to the obtained filtrate, and the precipitated solid was collected by filtration. The collected solid was suspended in acetic anhydride (5 mL) and heated with stirring at 120°C for 1 hour. After allowing to cool to room temperature, the precipitated solid was collected by filtration, and the obtained solid was washed with chloroform. Low boiling points were distilled off from the filtrate after washing, and the resulting solid was purified by recrystallization (1,4-dioxane) to obtain the target compound, 4-(1,3,5,7-tetraoxo-5,7-dihydro-1H-furo[3,4-f]isoindol-6(3H)-yl)-2-(trifluoromethyl)benzonitrile (yield: 1.49 g, 24%). １ H-NMR (CDCl ３ ) δ (ppm): 7.98 (dd, J=8.5, 2.0Hz, 1H), 8.05 (d, J=8.5Hz, 1H), 8.10 (d, J=2.0Hz, 1H), 8.61 (s, 2H).

[0128] (Synthesis Example 1: Synthesis of Compound (B2)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (1.37 g, 3.73 mmol), 4-aminophthalonitrile (802 mg, 5.60 mmol), and 1,4-diazabicyclo[2.2.2]octane (209 mg, 1.86 mmol) were suspended in N,N-dimethylformamide (37 mL) and stirred at 120°C for 6 hours. After cooling to room temperature, water was added to the reaction solution and the precipitated solid was collected by filtration. The collected solid was washed with water, methanol, and diethyl ether, in that order. The obtained solid was then washed with hot dioxane and diethyl ether, in that order, to obtain the target compound (B2) (yield 1.70 g, 92%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.79-8.73 (m, 4H), 8.41 (d, J = 8Hz, 1H), 8.37 (d, J = 2Hz, 1H), 8.13 (dd, J = 8, 2Hz, 1H), 8.11-8.05 (m, 2H), 7.78-7.71 (m, 2H).

[0129] (Synthesis Example 2: Synthesis of Compound (B3)) The same operations as in Synthesis Example 1 were carried out, except that the compound (1.37 g, 3.73 mmol) and 3-aminophthalonitrile (802 mg, 5.60 mmol) obtained in Synthesis Reference Example 2 were used instead of the compound (1.37 g, 3.73 mmol) and 4-aminophthalonitrile (802 mg, 5.60 mmol) obtained in Synthesis Reference Example 1, respectively, to obtain the target compound (B3) (yield 1.38 g, 75%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.80-8.76 (m, 4H), 8.42 (dd, J = 8.4, 0.4Hz, 1H), 8.37 (dd, J = 2.0, 0.4Hz, 1H), 8.14 (dd, J = 8.4 , 2.0Hz, 1H), 8.05-8.01 (m, 2H), 7.89 (ddd, J=8.0, 1.6, 0.8Hz, 1H), 7.83 (ddd, J=8.0, 8.0, 0.8Hz, 1H).

[0130] (Synthesis Example 3: Synthesis of Compound (B12)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (3.00 g, 8.14 mmol) and 4-aminopyridine (1.15 g, 12.2 mmol) were suspended in pyridine (80 mL) and stirred at 120°C for 2 hours. After cooling to room temperature, water was added to the reaction solution and the precipitated solid was collected by filtration. The obtained solid was purified by recrystallization (DMF / toluene) to obtain the target compound (B12) (yield: 1.73 g, 58%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.85-8.79 (m, 2H), 8.76 (br-s, 4H), 8.08 (d, J = 8.6Hz, 2H), 7.74 (d, J = 8.6Hz, 2H), 7.62-7.56 (m, 2H).

[0131] (Synthesis Example 4: Synthesis of compound (B15)) Under an argon atmosphere, the compound obtained in Reference Synthesis Example 2 (0.95 g, 2.41 mmol) and 4-aminopyridine (272 mg, 2.88 mmol) were suspended in pyridine (24 mL) and stirred at 120°C for 2 hours. After cooling to room temperature, water was added to the reaction solution and the precipitated solid was collected by filtration. The obtained solid was purified by recrystallization (DMF / methanol) to obtain the target compound (B15) (yield: 0.94 g, 83%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.83-8.81 (m, 2H), 8.77-8.75 (m, 4H), 8.41 (d, J = 8.3Hz, 1H), 8.37 (d, J=2.0Hz, 1H), 8.13 (dd, J=8.3, 2.0Hz, 1H), 7.59-7.57 (m, 2H).

[0132] (Synthesis Example 5: Synthesis of Compound (B18)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (1.46 g, 12.2 mmol), 4-aminopicolinonitrile (2.18 g, 18.3 mmol), and 1,4-diazabicyclo[2.2.2]octane (457 mg, 4.08 mmol) were suspended in N,N-dimethylformamide (80 mL) and stirred at 120°C for 3 hours. After cooling to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The resulting solid was purified by recrystallization (DMF / toluene) to obtain the target compound (B18) (yield: 2.34 g, 61%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.04 (d, J = 5.2Hz, 1H), 8.82-8.70 (m, 4H), 8.29 (d, J = 1.8Hz, 1H), 8.08 (d, J=8.4Hz, 2H), 8.00 (dd, J=5.2, 1.8Hz, 1H), 7.73 (d, J=8.4Hz, 2H).

[0133] (Synthesis Example 6: Synthesis of compound (B43)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (0.81 g, 2.20 mmol), 5-aminopicolinonitrile (393 mg, 3.30 mmol), and 1,4-diazabicyclo[2.2.2]octane (123 mg, 1.10 mmol) were suspended in N,N-dimethylformamide (22 mL) and stirred at 120°C for 3 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure to approximately two-thirds of its original volume, water was added, and the precipitated solid was collected by filtration. The collected solid was washed with water, methanol, and diethyl ether, in that order. The obtained solid was then washed with hot dioxane and diethyl ether, in that order, to obtain the target compound (B43) (yield: 0.76 g, 74%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.92 (dd, J = 2.0, 1.0 Hz, 1H), 8.81-8.72 (m, 4H), 8.34 (dd, J = 8.0, 1. 0Hz, 1H), 8.28 (dd, J=8.0, 2.0Hz, 1H), 8.12-8.05 (m, 2H), 7.78-7.71 (m, 2H).

[0134] (Synthesis Example 7: Synthesis of compound (B72)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (100 mg, 0.27 mmol), 4-aminoquinoline (58.4 mg, 0.41 mmol), and 1,4-diazabicyclo[2.2.2]octane (15.0 mg, 0.14 mmol) were suspended in N,N-dimethylformamide (2.7 mL) and stirred at 120°C for 2 hours. After cooling to room temperature, water was added to the reaction solution and the precipitated solid was collected by filtration. The obtained solid was purified by washing with hot dioxane to obtain the target compound (B72) (yield 97.0 mg, 73%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.14 (d, J=4.5Hz, 1H), 8.81-8.73 (m, 4H), 8.20 (dd, J=8.4, 1.0Hz, 1H), 8.16 (dd, J=8.4, 1.0Hz, 1H), 8.09 (d, J=8.6Hz, 2 H), 7.86 (ddd, J=8.4, 6.8, 1.0Hz, 1H), 7.81 (d, J=4.5Hz, 1H), 7.77 (d, J=8.6Hz, 2H), 7.61 (ddd, J=8.4, 6.8, 1.0Hz, 1H).

[0135] (Synthesis Example 8: Synthesis of Compound (B4)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (553 mg, 1.50 mmol), 5-amino-2-cyanobenzotrifluoride (372 mg, 2.00 mmol), and 1,4-diazabicyclo[2.2.2]octane (84.2 mg, 0.75 mmol) were suspended in N,N-dimethylformamide (15 mL) and stirred at 120°C for 16 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure to approximately half its original volume, water was added, and the precipitated solid was collected by filtration. The solid was washed with water, methanol, and diethyl ether, in that order, to obtain the target compound (B4) (yield 695 mg, 87%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.81-8.70 (m, 4H), 8.46 (d, J = 8Hz, 1H), 8.32 (d, J = 2Hz, 1H), 8.15-8.04 (m, 3H), 7.77-7.71 (m, 2H); １９ F-NMR (DMSO-d ６ ) δ (ppm): -60.8.

[0136] (Synthesis Example 9: Synthesis of Compound (B7)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (2.03 g, 5.50 mmol), 3,5-dicyanoaniline (1.02 g, 7.15 mmol), and 1,4-diazabicyclo[2.2.2]octane (309 mg, 2.75 mmol) were suspended in N,N-dimethylformamide (110 mL), and the mixture was stirred at 120°C for 18 hours. After allowing to cool to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was washed with water, methanol, and diethyl ether, in that order, to obtain the target compound (B7) (yield: 2.26 g, 83%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.84-8.71 (m, 4H), 8.68 (t, J=2Hz, 1H), 8.43 (d, J=2Hz, 2H), 8.11-8.06 (m, 2H), 7.77-7.70 (m, 2H).

[0137] (Synthesis Example 10: Synthesis of compound (B9)) Under an argon atmosphere, the compound obtained in Reference Synthesis Example 4 (347 mg, 0.883 mmol), 4-aminophthalonitrile (189 mg, 1.32 mmol), and 1,4-diazabicyclo[2.2.2]octane (49.6 mg, 0.442 mmol) were suspended in N,N-dimethylformamide (9 mL) and stirred at 120°C for 2 hours. After cooling to room temperature, low boiling points were removed by distillation under reduced pressure, and water (25 mL) was added. The solid was collected by filtration and washed with water and diethyl ether to obtain a crude product. The obtained solid was washed successively with hot methanol (20 mL), hot dioxane (8 mL), and diethyl ether to obtain the target compound (B9) (yield 350 mg, 76%). １ H-NMR (DMSO-d6) δ (ppm): 8.82-8.76 (s, 4H), 8.69 (t, J = 1.5Hz, 1H), 8 .45-8.38 (m, 3H), 8.35 (d, J=2.0Hz, 1H), 8.12 (dd, J=8.0, 2.0Hz, 1H). (Synthesis Example 11: Synthesis of compound (B17)) Under an argon atmosphere, the compound obtained in Reference Synthesis Example 4 (72 mg, 0.76 mmol) and 4-aminopyridine (86 mg, 0.91 mmol) were suspended in pyridine (5 mL) and stirred at 120°C for 2 hours. After cooling to room temperature, water was added and the precipitated solid was collected by filtration. The obtained solid was purified by recrystallization (DMF / toluene) to obtain the target compound (B17) (yield 164 mg, 69%). １ H-NMR (CDCl ３ ) δ (ppm): 7.57 (dd, J=1.5, 4.6Hz, 2H), 8.43 (d, J=1.5Hz, 2H), 8.67 (t, J=1.5Hz, 1H), 8.77 (m, 4H), 8.82 (dd, J=1.5, 4.6Hz, 2H).

[0138] (Synthesis Example 12: Synthesis of compound (B19)) Under an argon atmosphere, the compound obtained in Reference Synthesis Example 2 (1.92 g, 5.20 mmol), 4-aminopicolinonitrile (867 mg, 7.28 mmol), and 1,4-diazabicyclo[2.2.2]octane (291 mg, 2.60 mmol) were suspended in N,N-dimethylformamide (52 mL) and stirred at 120°C for 8 hours. After cooling to room temperature, water was added to the reaction solution and the precipitated solid was collected by filtration. The obtained solid was purified by recrystallization (DMF / toluene) to obtain the target compound (B19) (yield: 829 mg, 34%). Mass spectrometry (QTOF-MS): 469

[0139] (Synthesis Example 13: Synthesis of compound (B24)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (1.50 g, 4.05 mmol), 4-amino-2-(trifluoromethyl)pyridine (986 mg, 6.08 mmol), and 1,4-diazabicyclo[2.2.2]octane (225 mg, 2.03 mmol) were suspended in N,N-dimethylformamide (41 mL), and the mixture was stirred at 120°C for 18 hours. After cooling to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The obtained solid was purified by recrystallization (DMF) to obtain the target compound (B24) (yield: 1.39 g, 67%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.05 (d, J = 5.1Hz, 1H), 8.73-8.79 (m, 4H), 8.21 (d, J = 1.2Hz, 1H), 8.08 (d, J=8.7Hz, 2H), 7.96 (dd, J=5.0, 1.4Hz, 1H), 7.74 (d, J=8.7Hz, 2H). １９ F-NMR (DMSO-d ６ ) δ (ppm): -66.1.

[0140] (Synthesis Example 14: Synthesis of compound (B28)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (1.00 g, 2.70 mmol), 4-amino-2,6-pyridinedicarbonitrile (584 mg, 4.05 mmol), and 1,4-diazabicyclo[2.2.2]octane (151 mg, 1.35 mmol) were suspended in quinoline (41 mL), and the mixture was stirred at 150°C for 18 hours. After cooling to room temperature, diethyl ether was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was washed with diethyl ether and then purified by recrystallization (DMF / toluene) to obtain the target compound (B28) (yield: 0.60 g, 45%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.30-8.52 (m, 6H), 8.08 (d, J=8.3Hz, 2H), 7.73 (d, J=8.3Hz, 2H).

[0141] (Synthesis Example 15: Synthesis of compound (B31)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 4 (300 mg, 0.76 mmol), 4-amino-2,6-pyridinedicarbonitrile (165 mg, 1.14 mmol), and 1,4-diazabicyclo[2.2.2]octane (42.7 mg, 0.38 mmol) were suspended in quinoline (7.6 mL), and the mixture was stirred at 150°C for 18 hours. After cooling to room temperature, diethyl ether was added to the reaction solution, and the precipitated solid was collected by filtration. The obtained solid was washed with diethyl ether and then purified by recrystallization (DMF / toluene) to obtain the target compound (B31) (yield 166 mg, 42%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.87-8.73 (m, 4H), 8.68 (t, J=1.5Hz, 1H), 8.63 (s, 2H), 8.41 (d, J=1.5Hz, 2H).

[0142] (Synthesis Example 16: Synthesis of compound (B39)) Under an argon atmosphere, 7-phenyl-1H-isochromeno[6,5,4-def]isoquinoline-1,3,6,8(7H)-tetraone (1.40 g, 4.10 mmol), 4,4'-(4-aminopyridine-2,6-diyl)dibenzonitrile (1.50 g, 4.90 mmol), and 1,4-diazabicyclo[2.2.2]octane (230 mg, 2.00 mmol) were suspended in N,N-dimethylformamide (9 mL) and stirred at 120°C for 12 hours. After cooling to room temperature, the precipitated solid was collected by filtration and washed with water and ethanol. The resulting solid was purified by recrystallization (DMF / toluene) to obtain the target compound (B39) (yield: 1.24 g, 49%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.82-8.76 (m, 4H), 8.48-8.43 (m, 6H), 8.09 (d, J=8.6Hz, 4H), 7.61-7.56 (m, 2H), 7.55-7.46 (m, 3H).

[0143] (Synthesis Example 17: Synthesis of compound (B44)) The same procedure as in Synthesis Example 12 was carried out, except that 5-aminopicolinonitrile (867 mg, 7.28 mmol) was used instead of 4-aminopicolinonitrile (867 mg, 7.28 mmol), to obtain the target compound (B44) (yield: 1.41 g, 58%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.92 (d, J = 2.2 Hz, 1H), 8.81-8.73 (m, 4H), 8.34 (d, J = 8.2 Hz, 1H), 8.28 (dd, J = 8.2, 2.2Hz, 1H), 8.05-7.99 (m, 2H), 7.89 (dt, J=7.9, 1.5Hz, 1H), 7.82 (t, J=7.9Hz, 1H). Mass spectrometry (QTOF-MS): 469

[0144] (Synthesis Example 18: Synthesis of compound (B74)) Under a nitrogen atmosphere, the compound obtained in Synthesis Reference Example 3 (762 mg, 1.82 mmol) and 4-aminoquinoline (319 mg, 2.21 mmol) were dissolved in pyridine (18 mL) and stirred at 110°C for 4 hours. After cooling to room temperature, crystallization was carried out, and the resulting precipitate was collected by filtration and dried under vacuum with heating. The resulting solid was suspended in dioxane, heated to 120°C, cooled to room temperature, and then filtered; this procedure was repeated twice. The resulting solid was then purified by recrystallization (DMF / toluene) to obtain the target compound (B74) (yield: 540 mg, 57%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.15 (d, J = 4.5Hz, 1H), 8.78 (br, 4H), 8.42 (d, J = 8.3Hz, 1H), 8.41 (d, J = 2.0Hz, 1H), 8.22-8.15 (m, 2H), 8.17 (dd, J=8.3, 2.0Hz, 1H), 7.87 (ddd, J=8.4, 6.9, 1.4Hz, 1H), 7.81 (d, J=4.5Hz, 1H), 7.61 (ddd, J=8.2, 6.8, 1.1Hz, 1H).

[0145] (Synthesis Example 19: Synthesis of compound (B151)) Under an argon atmosphere, 7-phenyl-1H-isochromeno[6,5,4-def]isoquinoline-1,3,6,8(7H)-tetraone (1.03 g, 3.00 mmol), 4-aminobenzonitrile (532 mg, 4.50 mmol), and 1,4-diazabicyclo[2.2.2]octane (168 mg, 1.50 mmol) were suspended in N,N-dimethylformamide (30 mL) and stirred at 120° C. for 18 hours. After cooling to room temperature, water (50 mL) was added, and the precipitated solid was collected by filtration and washed with water and diethyl ether to obtain the target compound (B151) (yield 1.10 g, 83%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.74 (s, 4H), 8.08 (AA'BB'system, pseudo-dt, 2H), 7.74 (AA'BB'system, pseudo-dt, 2H), 7.61-7.54 (m, 2H), 7.54-7.45 (m, 3H).

[0146] (Synthesis Example 20: Synthesis of compound (B153)) Under an argon atmosphere, 7-phenyl-1H-isochromeno[6,5,4-def]isoquinoline-1,3,6,8(7H)-tetraone (111 mg, 0.30 mmol), 2-aminobenzonitrile (53.2 mg, 0.45 mmol), and 1,4-diazabicyclo[2.2.2]octane (16.8 mg, 0.10 mmol) were suspended in N,N-dimethylformamide (3 mL) and stirred at 120°C for 18 hours. After cooling to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was washed with water, methanol, and diethyl ether, successively, to obtain the target compound (B153) (yield 52.2 mg, 37%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.23-8.42 (m, 4H), 8.15 (d, J = 7.8Hz, 1H), 8.09 (d, J = 8.2Hz, 2H), 8.00 (t, J=7.8Hz, 1H), 7.85 (d, J=7.8Hz, 1H), 7.78 (t, J=7.8Hz, 1H), 7.73 (d, J=8.2Hz, 2H).

[0147] (Synthesis Example 21: Synthesis of compound (B155)) Under an argon atmosphere, 7-phenyl-1H-isochromeno[6,5,4-def]isoquinoline-1,3,6,8(7H)-tetraone (1.03 g, 3.00 mmol), 3,5-dicyanoaniline (558 mg, 4.50 mmol), and 1,4-diazabicyclo[2.2.2]octane (168 mg, 1.50 mmol) were suspended in N,N-dimethylformamide (30 mL) and stirred at 120° C. for 18 hours. After cooling to room temperature, water (50 mL) was added, and the precipitated solid was collected by filtration and washed with water and diethyl ether to obtain the target compound (B155) (yield 1.22 g, 87%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.76 (s, 4H), 8.68 (t, J=1.5Hz, 1H), 8.44 (d, J=1.5Hz, 2H), 7.61-7.54 (m, 2H), 7.54-7.44 (m, 3H).

[0148] (Synthesis Example 22: Synthesis of compound (B164)) Under an argon atmosphere, 7-phenyl-1H-isochromeno[6,5,4-def]isoquinoline-1,3,6,8(7H)-tetraone (1.00 g, 2.90 mmol), 5'-aminoterphenyl-4,4'-dicarbonitrile (1.00 g, 3.50 mmol), and 1,4-diazabicyclo[2.2.2]octane (160 mg, 1.50 mmol) were suspended in N,N-dimethylformamide (58 mL) and stirred at 120°C for 12 hours. After cooling to room temperature, the precipitated solid was collected by filtration and washed with water and ethanol. The resulting solid was purified by recrystallization (DMF / toluene) to obtain the target compound (B164) (yield: 1.40 g, 78%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.78-8.73 (m, 4H), 8.29 (t, J=2.0Hz, 1H), 8.10-8.00 (m, 10H), 7.61-7.55 (m, 2H), 7.54-7.45 (m, 3H). Mass spectrometry (QTOF-MS): 620

[0149] (Synthesis Example 23: Synthesis of compound (B169)) Under a nitrogen atmosphere, the compound obtained in Reference Synthesis Example 1 (53.0 mg, 0.14 mmol), 4-amino-1-naphthalenecarbonitrile (29.1 mg, 0.17 mmol), and 1,4-diazabicyclo[2.2.2]octane (8.2 mg, 0.07 mmol) were dissolved in N,N-dimethylformamide (1.4 mL), and the mixture was stirred at 120°C for 15 hours. After allowing the mixture to cool to room temperature, the low-boiling components of the reaction solution were distilled off under reduced pressure. The resulting residue was washed with water and then with methanol, and dried in vacuo to obtain a crude product. The crude product was purified by recrystallization (DMF / methanol / water) to obtain the target compound (B169) (yield: 1.0 mg, 1%). １ H-NMR (DMSO-d ６) δ (ppm): 8.76 (br, 4H), 8.42 (d, J = 7.7Hz, 1H), 8.30-8.26 (m, 2H), 8.10 (d, J = 8.5Hz, 2H) ), 7.97 (d, J=7.6Hz, 1H), 7.93-7.88 (m, 1H), 7.77 (d, J=8.5Hz, 2H), 7.74-7.69 (m, 1H).

[0150] (Synthesis Example 24: Synthesis of compound (B170)) Under a nitrogen atmosphere, the compound obtained in Synthesis Reference Example 5 (1.04 g, 2.64 mmol), 4-aminophthalonitrile (573 mg, 3.90 mmol, 1.6 eq.), and 1,4-diazabicyclo[2.2.2]octane (147 mg, 1.32 mmol, 0.5 eq.) were dissolved in N,N-dimethylformamide (27 mL), and the solution was stirred at 120°C for 18 hours. After cooling to room temperature, crystallization was carried out, and the resulting precipitate was collected by filtration and dried under vacuum with heating. The resulting solid was purified by recycled GPC (solvent: DMF) and then purified by recrystallization (DMF / toluene), to obtain the target compound (B170) (yield: 268 mg, 22%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.79 (d, J = 7.6 Hz, 2H), 8.77 (d, J = 7.6 Hz, 2H), 8.42 (d, J = 8.3H z, 1H), 8.41 (d, J = 2.0Hz, 1H), 8.16 (dd, J = 8.3, 2.0Hz, 1H), 8.14-8.08 ( m, 2H), 7.97 (d, J = 8.4Hz, 1H), 7.72 (s, 1H), 7.71 (dd, J = 12.1, 7.3Hz, 1H ), 7.60 (ddd, J=8.1, 6.8, 1.1Hz, 1H), 7.45 (ddd, J=8.3, 6.9, 1.2Hz, 1H).

[0151] (Synthesis Example 25: Synthesis of compound (B173)) Under an argon atmosphere, the compound obtained in Synthesis Reference Example 1 (111 mg, 0.300 mmol), 2-aminobenzonitrile (53.2 mg, 0.450 mmol), and 1,4-diazabicyclo[2.2.2]octane (16.8 mg, 0.100 mmol) were suspended in N,N-dimethylformamide (3 mL), and the mixture was stirred at 120°C for 18 hours. After allowing to cool to room temperature, water was added to the reaction solution, and the precipitated solid was collected by filtration. The solid was washed with water, methanol, and diethyl ether, in that order, to obtain the target compound (B173) (yield 52.2 mg, 37%). １ H-NMR (DMSO-d ６ ) δ (ppm): 9.23-8.42 (m, 4H), 8.15 (d, J = 7.8Hz, 1H), 8.09 (d, J = 8.2Hz, 2H), 8.00 (t, J=7.8Hz, 1H), 7.85 (d, J=7.8Hz, 1H), 7.78 (t, J=7.8Hz, 1H), 7.73 (d, J=8.2Hz, 2H).

[0152] (Synthesis Example 26: Synthesis of compound (B178)) The same procedure as in Synthesis Example 25 was carried out, except that 4,6-diphenylpyrimidin-2-amine (111.3 mg, 0.450 mmol) was used instead of 2-aminobenzonitrile (53.2 mg, 0.450 mmol), to obtain the target compound (B178) (yield: 21.5 mg, 12%). Mass spectrometry (QTOF-MS): 597

[0153] (Synthesis Example 27: Synthesis of compound (B189)) The same procedure as in Synthesis Example 14 was carried out, except that the compound obtained in Synthesis Reference Example 2 (1.00 g, 2.70 mmol) was used instead of the compound obtained in Synthesis Reference Example 1 (1.00 g, 2.70 mmol), to give the target compound (B189) (yield 0.56 g, 42%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.89-8.69 (m, 4H), 8.64 (s, 2H), 8.05-7.99 (m, 2H), 7.91-7.80 (m, 2H).

[0154] (Synthesis Example 28: Synthesis of compound (C148)) Under an argon atmosphere, the compound obtained in Reference Synthesis Example 6 (100 mg, 0.26 mmol) and 4-aminopyridine (29.4 mg, 0.31 mmol) were suspended in N,N-dimethylformamide (3 mL) and heated with stirring at 150°C for 14 hours. After cooling to room temperature, the precipitated solid was filtered off, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain the target compound (C148) (yield: 12.2 mg, 10%). Mass spectrometry (QTOF-MS): 463

[0155] (Synthesis Example 29: Synthesis of Compound (C3)) The same procedure as in Synthesis Example 28 was carried out, except that 4-aminobenzonitrile (37.0 mg, 0.31 mmol) was used instead of 4-aminopyridine (29.4 mg, 0.31 mmol), to obtain the target compound (C3) (yield 19.0 mg, 15%). Mass spectrometry (QTOF-MS): 486

[0156] (Synthesis Example 7: Synthesis of compound (D1)) Under a nitrogen stream, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.34 g, 5.0 mmol), 4-aminobenzonitrile (1.24 g, 10.5 mmol), isoquinoline (0.56 g, 4.3 mmol), and 20 mL of m-cresol were added to a 100 mL three-neck flask and stirred at 180°C for 4 hours. After cooling to room temperature, the precipitated solid was filtered and washed with ethanol. Next, the obtained solid was recrystallized from dimethylformamide to obtain the target compound (D1) (1.64 g, yield 70%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.74 (s, 4H), 8.08 (d, J = 8.6Hz, 4H), 7.74 (d, J = 8.6Hz, 4H)

[0157] (Synthesis Comparative Example 1: Synthesis of Compound (E1)) The same procedure as in Synthesis Reference Example 7 was carried out, except that 4-aminopyridine (0.99 g, 10.5 mmol) was used instead of 4-aminobenzonitrile (1.24 g, 10.5 mmol), to obtain the target compound (E1) (yield 1.43 g, 68%). １H-NMR (DMSO-d ６ ) δ (ppm): 8.81 (dd, J=4.8, 0.8Hz, 4H), 8.75 (s, 4H), 7.59 (dd, J=4.8, 0.8Hz, 4H)

[0158] (Comparative Synthesis Example 2: Synthesis of Compound (E2)) The same procedure as in Synthesis Reference Example 7 was carried out, except that aniline (0.98 g, 10.5 mmol) was used instead of 4-aminobenzonitrile (1.24 g, 10.5 mmol), to obtain the target compound (E2) (yield 0.84 g, 40%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.72 (s, 4H), 7.59-7.45 (m, 10H)

[0159] (Evaluation Example 1: Evaluation of Film Quality of Compound (B2)) A Si substrate (with a native oxide film) was introduced into a vacuum deposition chamber, and a 1.0×10 －４ The pressure was reduced to 100 Pa. Then, a film of 30 nm was formed on a substrate from the sublimation-purified compound (B2), and the surface condition of the film was observed using an atomic force microscope (Shimadzu Corporation, SPM-9600). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.84 nm.

[0160] (Evaluation Example 2: Evaluation of film quality of compound (B3)) Measurement was carried out in the same manner as in Evaluation Example 1, except that compound (B3) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.39 nm.

[0161] (Evaluation Example 3: Film Quality Evaluation of Compound (B18)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B18) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.26 nm. (Evaluation Example 4: Film Quality Evaluation of Compound (B72)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B72) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.29 nm. (Evaluation Example 5: Film Quality Evaluation of Compound (B4)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B4) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.38 nm. (Evaluation Example 6: Film Quality Evaluation of Compound (B17)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B17) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.23 nm. (Evaluation Example 7: Film Quality Evaluation of Compound (B24)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B24) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.32 nm. (Evaluation Example 8: Film Quality Evaluation of Compound (B28)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B28) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.28 nm. (Evaluation Example 9: Film Quality Evaluation of Compound (B164)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (B164) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.18 nm. (Evaluation Example 10: Evaluation of film quality of compound (B170)) Measurement was carried out in the same manner as in Evaluation Example 1, except that compound (B170) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.33 nm.

[0162] (Evaluation Reference Example 1: Evaluation of Film Quality of Compound (D1)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (D1) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 2.17 nm. (Evaluation Comparative Example 1: Evaluation of Film Quality of Compound (E1)) Measurement was performed in the same manner as in Evaluation Example 1, except that compound (E1) was used instead of compound (B2). The arithmetic mean roughness (Ra) in the surface roughness measurement was 8.92 nm.

[0163] From the above film quality evaluation, it was confirmed that the film formed using the compound (D1) of Evaluation Reference Example 1 had high smoothness. Furthermore, it was confirmed that the films formed using the compounds of Evaluation Examples 1 to 3 (B2, B3, B4, B17, B18, B24, B28, B72, B164, B170) had even higher film smoothness than the film formed using the compound (D1) of Evaluation Reference Example 1.

[0164] [Compounds used in evaluation]

[0165] <Fabrication and Evaluation of Hole-Only Device (HOD)> [Element Example 1] A hole-only device (HOD) having a structure consisting of a first electrode / hole injection layer / hole transport layer / hole transport promotion layer / second electrode was fabricated, and the hole transport properties of the device were evaluated. (First Electrode) A glass substrate with an ITO transparent electrode, on whose surface an ITO film (thickness 110 nm) was patterned in a stripe shape, was prepared as a substrate having a first electrode. This substrate was washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet cleaning.

[0166] (Preparation for Vacuum Vapor Deposition) Each layer was vacuum-deposited by a vacuum deposition method on the surface on which the ITO film was formed, of the two surfaces of the substrate that had been subjected to the surface treatment described above. First, the glass substrate was placed in a vacuum deposition chamber, and 1.0 × 10 －４ The pressure was reduced to Pa. Then, each layer was formed in the following order according to the film formation conditions.

[0167] (Fabrication of hole injection layer) MoO ３A 1 nm thick film was formed to prepare a hole injection layer. (Preparation of Hole Transport Layer) A 100 nm thick film of (HTL-1) was formed as a hole transport material to prepare a hole transport layer. (HTL-1) was synthesized by the method described in JP 2018-193371 A. (Preparation of Hole Transport Promotion Layer) A 10 nm thick film of the sublimation-purified compound (B12) was formed to prepare a hole transport promotion layer.

[0168] (Fabrication of Second Electrode) A 80 nm thick Au film was formed to fabricate a second electrode.

[0169] (Evaluation of hole transport capability of hole-only device) A positive electric field and a negative electric field of 10 mA / cm were applied to the first electrode and the second electrode of the hole-only device of Example 1, respectively. ２ The voltage value at a current density of 1000 kJ / s was measured. The results are shown in Table 1.

[0170] [Element Example 2] A hole-only device was fabricated in the same manner as in Element Example 1, except that compound (B72) was used instead of compound (B12) used in the preparation of the hole transport promotion layer in Element Example 1. The hole transport capacity of the resulting hole-only device was evaluated in the same manner as in Element Example 1. The results are shown in Table 1. [Element Reference Example 1] A hole-only device was fabricated in the same manner as in Element Example 1, except that compound (D1) was used instead of compound (B12) used in the preparation of the hole transport promotion layer in Element Example 1. The hole transport capacity of the resulting hole-only device was evaluated in the same manner as in Element Example 1. The results are shown in Table 1.

[0171] [Comparative Element Example 1] A hole-only device was fabricated in the same manner as in Element Example 1, except that the hole-transport promoting layer was not provided. The hole-transport capability of the resulting hole-only device was evaluated in the same manner as in Element Example 1. The results are shown in Table 1.

[0172] A hole-only device was fabricated in the same manner as in Element Example 1, except that compound (NPT) was used instead of compound (B12) used in the preparation of the hole transport promotion layer in Element Example 1. The hole transport ability of the resulting hole-only device was evaluated in the same manner as in Element Example 1. The results are shown in Table 1.

[0173]

[0174] The device of Device Example 1, which used compound (B12) as the hole transport promoting material, and the device of Device Example 2, which used compound (B72), showed lower voltages than the device of Device Comparative Example 1, which did not use a hole transport promoting material, and Device Comparative Example 2, which used the known material NPT. Furthermore, the device of Device Reference Example 1, which used compound (D1) as the hole transport promoting material, showed lower voltages than Device Comparative Examples 1 and 2. It was confirmed that the devices of Device Example 1 and Device Example 2 showed even lower voltages than the device of Device Reference Example 1.

[0175] <Preparation and Evaluation of Photoelectric Conversion Element> [Element Example 3] A photoelectric conversion element 1 having a layered structure consisting of a substrate / second electrode 16 / electron transport layer 15 / light-receiving layer 14 / hole transport layer 13 / hole transport promotion layer 12 / first electrode 11 was prepared, and the dark current and external quantum efficiency of the photoelectric conversion element were evaluated.

[0176] (Preparation of Substrate and Second Electrode 16) A glass substrate with an ITO transparent electrode, on which a 2 mm wide indium-tin oxide (ITO) film (film thickness 110 nm) was patterned in stripes, was prepared as a substrate having a second electrode on its surface. Next, this substrate was washed with isopropyl alcohol, and then subjected to surface treatment by ozone ultraviolet cleaning. (Preparation of Vacuum Vapor Deposition) Each layer was vacuum-deposited by vacuum deposition on the surface-treated substrate after cleaning, and each layer was laminated. First, the glass substrate was placed in a vacuum deposition chamber, and 7.0 × 10 －５The pressure was reduced to 100 Pa. Then, each layer was fabricated in the following order according to the film formation conditions. (Fabrication of Electron Transport Layer 15) The compound 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine, which had been purified by sublimation, was deposited to a thickness of 10 nm at a rate of 0.03 nm / sec to fabricate the electron transport layer 15. (Fabrication of Light Receiving Layer 14) N,N-dimethylquinacridone and fullerene C60 were deposited in a mass ratio of 4:1 to fabricate the photoelectric conversion layer 14, forming a film of 250 nm. The film formation rate was 0.13 nm / sec. (Fabrication of Hole Transport Layer 13) The hole transport material (HTL-1) was deposited to a thickness of 10 nm at a rate of 0.10 nm / sec to fabricate the hole transport layer 13. (Preparation of Hole Transport Promotion Layer 12) Compound (B2) was deposited at a rate of 0.20 nm / sec to a thickness of 10 nm to prepare the hole transport promotion layer 12. (Preparation of First Electrode 11) Finally, a metal mask was placed perpendicular to the ITO stripes on the substrate, and the first electrode 11 was deposited. For the first electrode, an Au film was deposited to a thickness of 80 nm. The Au deposition rate was 0.1 nm / sec.

[0177] From the above, the area is 4 mm ２ A photoelectric conversion element 1 shown in FIG. 1 was fabricated. A voltage of 2.5 V (absolute value) was applied to the photoelectric conversion element fabricated as described above so that electrons were transported to the second electrode 16 side and holes were transported to the first electrode 11 side. The current in the dark (dark current, mA / cm ２ The dark current was measured using a Keithley Source Measure Unit 2636B. The external quantum efficiency was measured using a solar cell spectral response measurement device (Soma Optical Co., Ltd.). The wavelength of the irradiated light was 560 nm, and the intensity was 50 μW / cm. ２ The measurements were carried out at 100°C. The results are shown in Table 2. The dark current and external quantum efficiency are relative values, with the result of Comparative Example 3 of the device described below being set as the reference value (100). The lower the dark current value, the better the performance, and the higher the external quantum efficiency value, the better the performance.

[0178] [Element Example 4] A photoelectric conversion element of Element Example 4 was prepared in the same manner as in Element Example 3, except that compound (B12) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 5] A photoelectric conversion element of Element Example 5 was prepared in the same manner as in Element Example 3, except that compound (B3) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 6] A photoelectric conversion element of Element Example 6 was prepared in the same manner as in Element Example 3, except that compound (B15) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 7] A photoelectric conversion element of Element Example 7 was prepared in the same manner as Element Example 3, except that compound (B18) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 8] A photoelectric conversion element of Element Example 8 was prepared in the same manner as Element Example 3, except that compound (B19) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 9] A photoelectric conversion element of Element Example 9 was prepared in the same manner as Element Example 3, except that compound (B24) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 10] A photoelectric conversion element of Element Example 10 was prepared in the same manner as in Element Example 3, except that compound (B28) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12, and the dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2.[Element Example 11] A photoelectric conversion element of Element Example 11 was prepared in the same manner as in Element Example 3, except that compound (B39) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 12] A photoelectric conversion element of Element Example 12 was prepared in the same manner as in Element Example 3, except that compound (B43) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 13] A photoelectric conversion element of Element Example 13 was prepared in the same manner as in Element Example 3, except that compound (B44) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 14] A photoelectric conversion element of Element Example 14 was prepared in the same manner as Element Example 3, except that compound (B72) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 15] A photoelectric conversion element of Element Example 15 was prepared in the same manner as Element Example 3, except that compound (B164) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Example 16] A photoelectric conversion element of Element Example 16 was prepared in the same manner as Element Example 3, except that compound (B170) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12. The dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2.

[0179] [Element Comparative Example 3] A photoelectric conversion element of Element Comparative Example 3 was prepared in the same manner as Element Example 3, except that compound (NPT) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12, and the dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2. [Element Comparative Example 4] A photoelectric conversion element of Element Comparative Example 4 was prepared in the same manner as Element Example 3, except that compound (E2) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12, and the dark current and external quantum efficiency were measured in the same manner as in Element Example 3. The results are shown in Table 2.

[0180] [Element Comparative Example 5] A photoelectric conversion element of Element Comparative Example 5 was prepared in the same manner as in Element Example 3, except that the hole transport promotion layer 12 was not provided, and the dark current was measured in the same manner as in Element Example 3. The results are shown in Table 2. In Element Comparative Example 4, the dark current was too large to measure the external quantum efficiency.

[0181] A photoelectric conversion element of Reference Example 2 was prepared in the same manner as in Example 3, except that compound (D1) was used instead of compound (B2) in the preparation of the hole transport promotion layer 12, and the dark current and external quantum efficiency were measured in the same manner as in Example 3. The results are shown in Table 2.

[0182]

[0183] As shown in Table 2, in the elements of Element Example 3 to Element Example 16 using the material for a photoelectric conversion element for an imaging element of the present invention, dark current was suppressed and high external quantum efficiency was obtained compared to the elements of Element Comparative Example 3, Element Comparative Example 4, and Element Comparative Example 5. Furthermore, Element Reference Example 2 using Compound D1 also showed suppressed dark current and improved external quantum efficiency compared to the elements of Element Comparative Example 3, Element Comparative Example 4, and Element Comparative Example 5. It was confirmed that Element Examples 3 to 16 further suppressed dark current and had higher external quantum efficiency than Element Reference Example 2.

[0184] By including the compound represented by formula (1), the organic electronic device of the present invention can improve hole transport ability, and when used in a photoelectric conversion device, can perform photoelectric conversion more efficiently. Furthermore, by including the compound represented by formula (1), the organic electronic device of the present invention can suppress dark current, and is expected to reduce noise when used in a photoelectric conversion device such as an imaging device. Furthermore, by including the compound represented by formula (1), the organic electronic device of the present invention can have high external quantum efficiency and can convert light into current without loss, and is expected to achieve high sensitivity when used in, for example, a photoelectric conversion device.

[0185] 1. Photoelectric conversion element 11. First electrode 12. Hole transport promoting 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 device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a structure represented by the following formula (1): In formula (1), ring A represents a monocyclic or condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms which may have a substituent. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring which may have a substituent. １ and Ar ２ each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of an element selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a linked and condensed ring); Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of the groups is substituted with at least one group selected from a cyano group and a trifluoromethyl group.

2. The ring A and the Ar １ and the Ar ２ 2. The organic electronic device according to claim 1, wherein the substituents are each independently a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, or an alkyl group having 2 to 10 carbon atoms.

3. The organic electronic device of claim 1, further comprising a light-receiving layer disposed between said first electrode and said second electrode.

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

5. The organic electronic device according to claim 3, wherein the organic layer includes a hole transport layer and a hole transport promotion layer containing a compound having the structure represented by formula (1), or includes a layer comprising a mixture of a hole transport material and a compound having the structure represented by formula (1).

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

7. The organic electronic device according to claim 1, wherein in formula (1), ring A is a benzene ring, a naphthalene ring, a phenylbenzene ring, a diphenylbenzene ring, a naphthylbenzene ring, a phenylnaphthalene ring, a pyridylnaphthalene ring, a pyridylbenzene ring or a dipyridylbenzene ring, optionally substituted with a cyano group, a fluoro group or a trifluoromethyl group.

8. In the formula (1), the Ar １ and the Ar ２ each independently represents a group in which 1 to 3 rings selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, triazine, quinoline, quinoxaline, and quinazoline, each of which may have a substituent, are linked, condensed, or linked and condensed.

9. In the formula (1), the Ar １ is a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, and a cyano-trifluoromethylphenyl group, and said Ar ２ is a group selected from the group consisting of a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dicyanophenyl group, a ditrifluoromethylphenyl group, a cyano-trifluoromethylphenyl group, a cyanobiphenyl group, a terphenyl group, a dicyanoterphenyl group, a naphthyl group, a cyanonaphthyl group, a phenanthryl group, a pyridyl group, a cyanopyridyl group, a trifluoromethylpyridyl group, a dicyanopyridyl group, a cyano-trifluoromethylpyridyl group, a diphenylpyridyl group, a terpyridyl group, a pyrazyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a diphenylpyrimidyl group, a diphenyltriazyl group, a dipyridyltriazyl group, a quinolyl group, a cyanoquinolyl group, a quinoxalinyl group, a cyanoquinoxalinyl group, a quinazolyl group, and a cyanoquinazolyl group.

10. The organic electronic device according to any one of claims 1 to 9, wherein in the formula (1), the ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

11. An imide compound represented by the following formula (1): In formula (1), ring A represents a monocyclic or condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms which may have a substituent. The aromatic hydrocarbon ring may be linked, directly or via a linking group, to another aromatic hydrocarbon ring or a heteroaromatic ring which may have a substituent. １ and Ar ２ each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of an element selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a ring formed by linking and condensing), Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of the groups is substituted with at least one group selected from a cyano group and a trifluoromethyl group.

12. Ar １ is a phenyl group which may have a substituent, Ar ２ is a group having 1 to 3 unsaturated 6-membered rings composed of elements selected from the group consisting of hydrogen, carbon and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a linked and condensed ring).

13. The ring A and the Ar １ and the Ar ２ 13. The imide compound according to claim 11, wherein the substituent is a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, a cyanoalkyl group having 2 to 10 carbon atoms, a fluoroalkyl group having 2 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, or an alkyl group having 2 to 10 carbon atoms.

14. The imide compound according to claim 11 or 12, wherein in formula (1), ring A is a benzene ring, a naphthalene ring, a phenylbenzene ring, a diphenylbenzene ring, a naphthylbenzene ring, a phenylnaphthalene ring, a pyridylnaphthalene ring, a pyridylbenzene ring, or a dipyridylbenzene ring, each of which may be substituted with a cyano group, a fluoro group, or a trifluoromethyl group.

15. In the formula (1), the Ar ２ is a group in which 1 to 3 rings selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, triazine, quinoline, quinoxaline, and quinazoline, each of which may have a substituent, are linked, condensed, or linked and condensed.

16. In the formula (1), the Ar １ is a group selected from the group consisting of a phenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, and a 4-cyano-3-trifluoromethylphenyl group, ２ are a 2-cyanophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3,4-dicyanophenyl group, a 3,5-dicyanophenyl group, a 3,5-bis(4-cyanophenyl)phenyl group, a 4-trifluoromethylphenyl group, a 3,5-ditrifluoromethylphenyl group, a 4-cyano-3-trifluoromethylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9-phenanthryl group, a 4-cyano-1-naphthyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 3-cyano-4-pyridyl group, a 4-cyano-3-pyridyl group, a 4-cyano The imide compound according to claim 11, which is a group selected from the group consisting of an ano-2-pyridyl group, a 3-trifluoromethyl-4-pyridyl group, a 3,5-dicyano-4-pyridyl group, a 4-cyano-5-trifluoromethyl-2-pyridyl group, a 3,5-diphenyl-4-pyridyl group, a 3,5-bis(4-cyanophenyl)-4-pyridyl group, a 3,5-bis(4-pyridyl)-4-pyridyl group, an m-terphenyl-5'-yl group, a 4,6-diphenylpyrimidin-2-yl group, a 4,6-diphenyl-1,3,5-triazin-2-yl group, and a 4-quinolyl group.

17. The imide compound according to claim 16, wherein in formula (1), ring A is an unsubstituted benzene ring or an unsubstituted naphthalene ring.

18. The imide compound according to claim 17, represented by any one of the following formulas:

19. A method for producing an imide compound represented by the following formula (1), which comprises reacting a compound represented by the following formula (2) with an amine compound represented by the following formula (3). In formulas (1), (2), and (3), ring A represents a monocyclic or condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms which may have a substituent. The aromatic hydrocarbon ring may be linked directly or via a linking group to another aromatic hydrocarbon ring or a heteroaromatic ring which may have a substituent. １ and Ar ２ each independently represents a group having 1 to 3 unsaturated 6-membered rings composed of an element selected from the group consisting of hydrogen, carbon, and nitrogen, which may have a substituent (the unsaturated 6-membered ring may be a monocycle, a linked ring, a condensed ring, or a ring formed by linking and condensing), Ar １ and Ar ２ are different from each other, provided that Ar １ and Ar ２ At least one of the groups is substituted with at least one group selected from a cyano group and a trifluoromethyl group.

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