Organic electronic element, hole transport promoting material, and imide compound

Abstract

The present invention provides an organic electronic element capable of improving hole transport capability, and an imide compound.　Provided is 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 an imide compound having a structure represented by formula (1). (In the formula; Ar1 and Ar2 represent arbitrary organic groups; at least one of Ar1 and Ar2 is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group which is represented by formula (Q1) and in which Cy1 is bonded at the ortho position; ring A represents a monocyclic or fused-ring aromatic hydrocarbon ring; and the aromatic hydrocarbon ring may be obtained by linking a plurality of aromatic hydrocarbon rings directly or via a linking group, and may be substituted with one or more groups selected from the group consisting of a cyano group, F, Cl, and Br.) (In formula (Q1), Cy1 and X1 to X4 are prescribed groups.)

Description

Organic electronic devices, hole transport promoting materials, and imide compounds

[0001] This invention relates to organic electronic devices, hole transport-promoting materials, and imide compounds.

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

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

[0004] Japanese Patent Publication No. 2019-182789

[0005] The present invention provides an organic electronic element, a hole transport-promoting material, and an imide compound that can improve the hole transport capability.

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

[0007] In other words, the present invention encompasses the following embodiments: [1] An organic electronic element comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains an imide compound having a structure represented by the following formula (1). (Ar １ Ar２ represents an arbitrary organic group. However, Ar １ or Ar ２ at least one of which is represented by the following formula (Q1) and is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group in which the following Cy １ is bonded to the ortho position. Ring A represents a monocyclic or condensed aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be one in which a plurality of aromatic hydrocarbon rings are linked directly or via a linking group, and may be substituted with one or more selected from the group consisting of a cyano group, F, Cl, and Br.) (In formula (Q1), Cy １ represents an organic group having a cyclic structure which may be substituted with R １ . X １ to X ４ each independently represents N, C—H or C—R ２ . R １ and R ２ each independently represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, a nitro group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and these substituents may be a group in which a plurality of them are combined.) [2] Ar １ , Ar ２ [[ID=二十九]] are the same group in formula (1), the organic electronic element according to [1]. [3] Ar １ , Ar ２ are different groups from each other in formula (1), the organic electronic element according to [1]. [4] In formula (Q1), X １ , X ２ , X ３ , and X ４ in which one or more of C—CN or N are present, the organic electronic element according to [1]. [5] Ar ２ [[ID=四十七]] is a group represented by formula (Q1), and Ar １ is an aromatic hydrocarbon group having 6 to １ which may be substituted with R １The organic electronic device according to [1], [3] or [4], which is a heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure. [6] Cy in formula (1) １ However, R １ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １ A heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with R １ [1] to [5] any organic electronic element, wherein the alkyl group having 3 to 30 carbon atoms has a cyclic structure which may be substituted with [1]. [7] The organic electronic element according to any (In formulas (A-1) to (A-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in ring A. １ When Z has １ (These may be the same or different.)

[11] An organic electronic element according to any one of [1] to

[10] , wherein the ring A in formula (1) is (A-1) or (A-2).

[12] A hole transport promoting material represented by the following formula (2). (Ar ２１ Ar ２２ represents any organic group. However, Ar ２１ or Ar ２２ At least one of these is represented by the following formula (Q2), and the following Cy is in the ortho position. ２Ring B is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group to which the two groups are bonded. Ring B represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups, and may be substituted with one or more groups selected from the group consisting of cyano groups, F, Cl, and Br. (In formula (Q2), Cy ２ R ２１ This represents an organic group having a cyclic structure that may be substituted with X. ２１ ~X ２４ These are, independently, N, C-H, or C-R ２１ Represents R ２１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ , represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents.)

[13] Ar in formula (2) ２１ Ar ２２ The hole transport promoting material described in

[12] , wherein the group is the same.

[14] Ar in formula (2) ２１ Ar ２２ A hole transport promoting material according to

[12] , wherein the groups are different from each other.

[15] In formula (Q2), X ２１ , X ２２ , X ２３ , and X ２４ Among these, one C-CN or N is present, as described in any of

[12] to

[14] .

[16] Ar in formula (2) ２２ The base is represented by formula (Q2), and Ar ２１ However, R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ The hole transport promoting material according to

[12] ,

[14] or

[15] , which is a heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure.

[17] Cy in formula (2) ２ However, R ２１A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ A heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with R ２１ A hole transport promoting material according to any one of

[12] to

[16] , wherein the ring B in formula (2) is represented by any one of the following (B-1) to (B-10). (In formulas (B-1) to (B-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in ring B. １ When Z has １ (These may be the same or different.)

[19] The hole transport promoting material according to any one of

[12] to

[18] , wherein the ring B in formula (2) is (B-1) or (B-2).

[20] An imide compound represented by the following formula (3). (Ar ３１ and Ar ３２ R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ This represents a heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure. However, Ar ３１ or Ar ３２ At least one of these is represented by the following formula (Q3), and the following Cy is in the ortho position. ３ The compound is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group bonded to a ring. Ring C represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by the direct linkage of multiple aromatic hydrocarbon rings or via linking groups, and may be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br. (In equation (Q3), Cy ３ R ３１ This represents an organic group having a cyclic structure that may be substituted with X. ３１ ~X ３４is, independently of each other, N, C—H or C—R ３１ represents. R ３１ is an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, a nitro group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 3 to 30 carbon atoms having a cyclic structure, and these substituents may be a group in which a plurality of them are combined. )

[21] Ar in formula (3) ３１ , Ar ３２ is the same group as described in

[20] , the imide compound.

[22] Ar in formula (3) ３１ , Ar ３２ are different groups from each other, the imide compound described in

[20] .

[23] In formula (Q3), X ３１ , X ３２ , X ３３ , and X ３４ among them, there is one of C—CN or N, the imide compound according to any one of

[20] to

[22] .

[24] Ar in formula (3) ３２ is a group represented by formula (Q3), and Ar ３１ is an aromatic hydrocarbon group having 6 to 30 carbon atoms (which may be substituted with a cyano group, CF ３ , F), a heteroaromatic group having from 3 to 30 carbon atoms (which may be substituted with a cyano group, CF ３ , F), or a group in which these are combined, the imide compound according to

[20] ,

[22] or

[23] .

[25] Ar in formula (3) ３１ is a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazolyl group, a quinolyl group, or an isoquinolyl group, and these groups are a cyano group, a cyanophenyl group, a dicyanophenyl group, a cyanopyridyl group, a dicyanopyridyl group, a fluoro group, and a trifluoromethyl group. The imide compound according to any one of

[20] to

[24] , which may be substituted with one or more groups selected from the group consisting of.

[26] Cy in formula (3) ３ is an aromatic hydrocarbon group having 6 to 30 carbon atoms which may be substituted with R ３１ , a heteroaromatic group having 3 to 30 carbon atoms which may be substituted with R ３１ , or R ３１An imide compound according to any one of

[20] to

[25] , which is an alkyl group having 3 to 30 carbon atoms and having a cyclic structure that may be replaced.

[27] Cy in formula (3) ３ is a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazyl group, a quinolyl group, or an isoquinolyl group, and these groups are each independently selected from a cyano group, a cyanophenyl group, a dicyanophenyl group, a cyanopyridyl group, a dicyanopyridyl group, a fluoro group, or a trifluoromethyl group An imide compound according to any one of

[20] to

[26] , which may be substituted with one or more of them.

[28] R in formula (3) ３１ is a cyano group, CF ３ , F, a phenyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, or a group formed by combining these, an imide compound according to any one of

[20] to

[27] .

[29] In the above formula (3), the ring C is represented by any one of the following (C-1) to (C-10), an imide compound according to any one of

[20] to

[28] .[[]]END]] (In formulas (C-1) to (C-10), Z １ represents a cyano group, F, Cl or Br. m represents 0, 1 or 2, n represents 0, 1 or two, and 0 ≦ m + n ≦ 4. When there are two or more Z １ ?in the ring C, Z １ may be the same or different from each other.)

[30] In the above formula (3), the ring C is (C-1) or (C-2), an imide compound according to any one of

[20] to

[29] .[[]]END]] <00004!7> According to the present invention, an organic electronic device, a hole transport promoting material, and an imide compound capable of improving the hole transport ability can be provided.[[]]END]] <00004!9>It is a schematic cross-sectional view showing an example of the laminated structure of the photoelectric conversion element according to the present invention. It is a schematic cross-sectional view showing an example of the laminated structure of the organic EL element according to the present invention.[[]]END]]

[0010] (Organic electronic device) The organic electronic device of the present invention includes a photoelectric conversion element and an organic electroluminescent element (organic EL element). A 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, and the like.[[]]END]]

[0011] The organic electronic device of the present invention comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode. The organic layer contains an imide compound having the structure represented by the following formula (1) (hereinafter also referred to as the imide compound represented by formula (1)).

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

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

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

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

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

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

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

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

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

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

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

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

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

[0025]

[0026] In formula (1), Ar １ Ar ２ represents any organic group. However, Ar １ or Ar ２ At least one of these is represented by the following formula (Q1), and the following Cy is in the ortho position. １ The ring A is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group to which the ring A is bonded. Ring A represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups. The aromatic hydrocarbon ring may also be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br.

[0027] The structure represented by equation (1) has Cy at the ortho position. １ The structure has a six-membered ring aromatic hydrocarbon group or a six-membered ring heteroaromatic group, characterized by the bonding of an organic group having a cyclic structure as shown in formula (1). In such a structure represented by formula (1), a bulky substituent Ar is attached to the central structure having ring A. １ Ar ２It has a structure represented by formula (1) at its end. From this point of view, imide compounds having the structure represented by formula (1) in the organic layer tend to exhibit amorphous properties, maintain surface smoothness, and easily improve adhesion with adjacent layers. Organic electronic devices containing such imide compounds are expected to have improved yield due to their high film quality. Furthermore, high film quality suppresses leakage current, making it possible to significantly reduce dark current, which is one of the challenges of photoelectric conversion elements. Moreover, according to the present inventors, when used as an organic electronic device, imide compounds having a six-membered ring with an organic group having a cyclic structure bonded to the ortho position tend to have a fast response speed (the time it takes for the current value to return to its pre-irradiation state after irradiation with a light pulse). The imide compound of the present application has good adhesion with adjacent layers due to its structural characteristics, and is expected to promote the exchange of carriers (electrons or holes) at the interface. It is presumed that this improves the external quantum efficiency and response speed (the time it takes for the current value to return to its pre-irradiation state after irradiation with a light pulse). Here, in the present invention, "ortho position" is a term indicating a substitution position, and in the six-membered ring of the group represented by formula (Q1), when the carbon atom bonded to the N atom in the imide ring of formula (1) is designated as position 1, it refers to the carbon atom at position 2.

[0028] Ar １ and Ar ２ Of these, at least one is a group represented by formula (Q1) described below. Ar in formula (1) １ Ar ２ These may be the same group or different groups. １ and Ar ２ It is preferable that the two groups be the same in that it is possible to reduce the manufacturing process and thus lower manufacturing costs. On the other hand, when used as a material for vapor deposition, Ar is preferable in that it is possible to lower the vapor deposition temperature. １ and Ar ２ It is preferable that these are different groups. Note that "different groups" refers to Ar １ and Ar ２ The difference is, Ar １ and Ar ２ The groups represented by may have the same type and number of substituents, differing only in the positions of the substituents, and Ar １ and Ar２ The groups represented by may have different numbers or types of substituents, or different numbers and types of substituents.

[0029] Ar １ and Ar ２ These are different groups, Ar ２ If is a substituent represented by formula (Q1), then Ar １ It may have any organic group. In this case, Ar １ Ar ２ The group may be represented by formula (Q1) with a different structure, or it may be a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heteroaromatic group, or an alkyl group which may have a branched or cyclic structure. The alkyl group may have a branched and cyclic structure. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. For example, R １ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １ Preferred examples include heteroaromatic groups having 3 to 30 carbon atoms that may be substituted with, or alkyl groups having 1 to 30 carbon atoms that may have a branched or cyclic structure. Considering the availability of raw materials and ease of synthesis, R １ A phenyl group which may be substituted with R １ Naphthyl group, R may be substituted with １ A pyridyl group may be substituted with R １ A pyrazyl group which may be substituted with R １ A pyrimidyl group which may be substituted with R １ A triazyl group may be substituted with R １ A quinolyl group which may be substituted with R １Isoquinolyl group, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, heptyl group, hexyl group, cyclohexyl group, adamantyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylethyl group, diadamantylmethyl group, or dicyclohexylmethyl group may be substituted with a phenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, bistrifluoromethylphenyl group, biphenylyl group, cyanobiphenylyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, It is even more preferable that the substituent is anonaphthyl, fluoronaphthyl, pyridyl, cyanopyridyl, dicyanopyridyl, fluoropyridyl, difluoropyridyl, tetrafluoropyridyl, trifluoromethylpyridyl, bistrifluoromethylpyridyl, cyanopyrimidyl, dicyanopyrimidyl, trifluoromethylpyrimidyl, bistrifluoromethylpyrimidyl, quinolyl, cyanoquinolyl, trifluoromethylquinolyl, fluoroquinolyl, difluoroquinolyl, cyanoisoquinolyl, trifluoromethylisoquinolyl, fluoroisoquinolyl, or difluoroisoquinolyl. Furthermore, if heat resistance of the film is required, it is effective to increase the glass transition temperature (Tg) of the material. Increasing the rotational energy of the substituent is effective in increasing Tg, and Ar １ or Ar ２ It is preferable that one of the components has a fused ring structure as a substructure. Preferred examples of the fused ring structure include naphthyl groups, quinolyl groups, isoquinolyl groups, etc., with quinolyl groups being the most preferred.

[0030] Let's explain the base represented by formula (Q1). In formula (Q1), Cy １ R １ This represents an organic group having a cyclic structure that may be substituted with X. １ ~X ４ These are, independently, N, C-H, or C-R ２ It represents.

[0031] X １ , X２ , X ３ , and X ４ Of these, it is preferable that there be one or more C-CN or N atoms, more preferably one to two, and particularly preferable that there be one C-CN or N atom. To enhance interaction with adjacent layers, it is preferable to have one to two C-CN or N atoms, and considering ease of manufacturing, it is preferable that there be one C-CN or N atom.

[0032] Cy １ R １ This represents an organic group having a cyclic structure which may be substituted with Cy. １ For example, R １ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １ A heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with R １ A preferred example is an alkyl group having 3 to 30 carbon atoms having a cyclic structure, which may be substituted with R. The organic group having a cyclic structure may be a monocycle, a fused ring, or a linked ring, and may be a fused ring or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. Furthermore, the organic group having a cyclic structure may be R １ If it is replaced with R １ You may have multiple of them. １ When there are multiple, R １ They may be the same or different.

[0033] When using the present imide compound as a vapor deposition material, the heat resistance of the material is required, Cy １ It is preferable that the organic group has a cyclic structure of a 6-membered ring. Considering the availability of raw materials and ease of synthesis, Cy １ For example, R １ A phenyl group which may be substituted with R １ Naphthyl group, R may be substituted with １ A pyridyl group may be substituted with R １ A pyrazyl group which may be substituted with R １ A pyrimidyl group which may be substituted with R １ A triazyl group may be substituted with R １ A quinolyl group which may be substituted with R１ Isoquinolyl group, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, heptyl group, hexyl group, cyclohexyl group, adamantyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylethyl group, diadamantylmethyl group, dicyclohexylmethyl group are preferred, and phenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, bistrifluoromethylphenyl group, biphenylyl group, cyanobiphenylyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group Anonaphthyl group, fluoronaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, cyanopyrimidyl group, dicyanopyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, fluoroquinolyl group, difluoroquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, fluoroisoquinolyl group, or difluoroisoquinolyl group are more preferred.

[0034] Preferred examples of the structure represented by formula (Q1) include, for example, (E-1) to (E-169) below.

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] Of the above, (E-3), (E-4), (E-5), (E-6), (E-7), (E-19), (E-21), (E-22), (E-23), (E-24), (E-31), (E-58), (E-59), (E-76), (E-77), (E-109), (E-116), (E-126), and (E-127) are even more preferred in terms of superior element performance. Furthermore, the introduction of cyano groups is effective in enhancing interaction with adjacent layers, and among these, (E-5), (E-6), (E-7), (E-19), (E-23), and (E-77) are particularly preferred.

[0046] In equations (1) and (Q1) explained above, R １ and R ２ These are, independently, aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, and CF. ３ X represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may be a group formed by a combination of multiple substituents. Note that in formula (1), X １ ~X ４ R joins as ２ (C-R ２ In R ２ ), Ar １ and / or Ar ２ When Cy is a base represented by formula (Q1) １ R bonded １ , and also, Ar １ When R is a group other than the group represented by formula (Q1) １ They may be the same in part or in whole, or they may be different in part or in whole.

[0047] R １ and R ２ These are, independently, aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F (fluorine), Cl (chlorine), Br (bromine), and CF. ３(Trifluoromethyl), a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, may be a group formed by a combination of multiple substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. １ and R ２ Each of them independently consists of a cyano group, F, and CF. ３ Phenyl group, naphthyl group, pyridyl group, pyrazyl group, triazyl group, quinolyl group, isoquinolyl group, adamantyl group, cyclohexyl group, cyclopentyl group, cyclobutyl group, cyclopropyl group, methyl group, ethyl group, or a combination thereof is preferred. In terms of good element performance, R １ This includes cyano group, trifluoromethyl group, phenyl group, cyanophenyl group, dicyanophenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, naphthyl group, cyanonaphthyl group, dicyanonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, bistrifluoromethylnaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, pyrimidyl group, Cyanopyrimidyl group, dicyanopyrimidyl group, fluoropyrimidyl group, difluoropyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, pyrazyl group, cyanopyramyrazyl group, dicyanopyramyrazyl group, fluoropyramyrazyl group, difluoropyramyrazyl group, trifluoromethylpyramyrazyl group, bistrifluoromethylpyramyrazyl group, triazyl group, cyanotriazyl group, dicyanotriazyl group, fluorotriazyl group, difluorotriazyl group, trifluoromethyltriazyl group, bistrifluoromethyltriazyl group, adamantyl group, cyclohexyl group, or methyl group are preferred. Considering the availability of raw materials and ease of synthesis, R １The group is preferably a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a pyridyl group, or a cyanopyridyl group, and more preferably a cyano group. １ and R ２ In this context, examples of the C6-C30 aromatic hydrocarbon groups include, independently, phenyl group, naphthyl group, anthryl group, phenantrenyl group, pyrenyl group, perilenyl group, triphenylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, biphenylyl group, terphenyl group, naphthylphenyl group, phenylnaphthyl group, binaphthyl group, anthrylphenyl group, phenylanthryl group, naphthylanthryl group, and the like. Phenyl or naphthyl groups are preferred for their superior element performance. １ and R ２ In the above, the heteroaromatic groups having 3 to 30 carbon atoms are, independently of each other, pyridyl group, pyrazyl group, pyrimidyl group, triazyl group, quinolyl group, isoquinolyl group, quinazolyl group, naphthyridyl group, quinoxalyl group, pyridopyradyl group, pteridyl group, pyrazinopyradyl group, pyrimidopyridyl group, benzoquinolyl group, benzoisoquinolyl group, benzoquinoxalyl group, phenantrolyl group, phenanthridyl group, and acridyl group. Examples include phenazinyl group, phenoxazinyl group, phenothiazinyl group, hexaazatoriphenylenyl group, thienyl group, furyl group, benzothienyl group, benzofuryl group, isobenzofuryl group, dibenzothiophenyl group, dibenzofuranyl group, benzoxazolyl group, pyrrole group, indole group, isoindole group, indolidinyl group, purine group, imidazolyl group, carbazolyl group, thiazolyl group, thiadiazolyl group, etc. Pyridyl group, pyrazyl group, pyrimidyl group, quinolyl group, or isoquinolyl group are preferred in terms of excellent device performance, and pyridyl group or pyrazyl group are even more preferred in terms of ease of synthesis. １ and R ２In this context, the perfluoroalkyl groups having 2 to 15 carbon atoms include, independently, perfluoroethyl, perfluoropropyl, perfluorobutyl, perfluoropentane, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorononane, perfluorodecane, perfluoroundecane, perfluorododecane, tridecane, perfluorotetradecane, and perfluoropentadecane, and these may be branched or cyclic perfluoroalkyl groups. １ and R ２ Examples of C1-C30 alkyl groups that may have a cyclic structure include, independently, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, tert-butyl, and isopropyl groups. C1-C10 alkyl groups that may have a cyclic structure are preferred because they are easy to synthesize, and examples include adamantyl, methyl, or ethyl groups. Methyl groups are even more preferred because they offer superior device performance.

[0048] In equation (1), X １ ~X ４ R joins as ２ (C-R ２ In R ２ The preferred group is a cyano group, fluoro group, trifluoromethyl group, phenyl group, pyridyl group, quinolyl group, or a combination thereof, with the cyano group being the most preferred. １ and / or Ar ２ When Cy is a base represented by formula (Q1) １ R bonded １ , and Ar １ When R is a group other than the group represented by formula (Q1) １ The preferred groups are cyano groups, fluoro groups, trifluoromethyl groups, phenyl groups, pyridyl groups, quinolyl groups, or combinations thereof, with cyano groups, phenyl groups, pyridyl groups, cyanophenyl groups, and cyanopyridyl groups being the most preferred.

[0049] Ring A represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups. The aromatic hydrocarbon ring may also be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br. Preferred examples of ring A are (A-1) to (A-10) below. (A-1) or (A-2) are even more preferred as ring A in terms of superior hole transport promotion performance. (A-2) is particularly preferred as ring A in terms of low raw material cost. (In formulas (A-1) to (A-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in ring A. １ When Z has １ These may be the same or different.

[0050] Preferred ring fusion positions (A-1) to (A-10) in ring A include, for example, (A-1') to (A-10') below. (In formulas (A-1') to (A-10'), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. In formulas (A-1') to (A-10'), there are 2 or more Z １ When Z has １ These elements may be the same or different.) Substituents on ring A include a cyano group, F, Cl, or Br. Of these, a cyano group or Br is preferred, and Br is even more preferred because it is easy to synthesize. In addition, while up to four substituents can be substituted on ring A, it is preferable to have 0, 1, or 2 substituents in order to keep the molecular weight down and lower the deposition temperature.

[0051] The organic electronic element of the present invention is not particularly limited, but examples include organic EL elements and photoelectric conversion elements (solar cells, photodiodes, photoelectric conversion elements for image sensors, etc.). Photoelectric conversion elements are preferred as the organic electronic element, and photoelectric conversion elements for image sensors are more preferred.

[0052] The imide compound represented by formula (1) is used as part of an organic electronic device. While not particularly limited, examples of parts of an organic electronic device include electron transport layers, light-emitting layers, light-receiving layers, hole injection layers, and hole transport-enhancing layers. Among these, the imide compound represented by formula (1) is preferably used in the hole transport-enhancing layer.

[0053] Preferred examples of imide compounds represented by formula (1) include, for example, (D-1) to (D-354) below. However, the imide compounds of the present invention are not limited to these.

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] Of the above, compounds having at least one cyano group are more preferable in order to enhance interaction with adjacent layers such as hole transport layers. Furthermore, compounds having nitrogen-containing heteroaromatic groups are more preferable in order to improve adhesion to electrodes.

[0085] [Manufacturing Method] The imide compound represented by formula (1) can be synthesized by known methods or a combination thereof. For example, a tetracarboxylic dianhydride represented by formula (4) below and an amine compound represented by formula (5) below are reacted to obtain a compound represented by formula (1a) below (Step 1). Furthermore, the obtained compound represented by formula (1a) below and an amine compound represented by formula (6) below are reacted to synthesize the imide compound represented by formula (1) below (Step 2). The imide compound represented by formula (1) can be synthesized in two steps (Steps 1 and 2) in this way, or it can be synthesized in one step.

[0086] (In the formula, Ar １ Ar ２(and ring A has the same definition as in formula (1) above.) The amino compound represented by formula (5) or (6) above may be a commercially available product, or it can be synthesized by combining conventionally known coupling reactions (for example, Journal of Organic Chemistry (2009), 74(8), 3225-3228). Examples of coupling reactions here include the Suzuki coupling reaction, Still coupling reaction, Kumada coupling reaction, and Hiyama coupling reaction, with the Suzuki coupling reaction being preferred because it yields a product of high purity.

[0087] The compound represented by formula (1a) or the imide compound represented by (1) above can be synthesized by referring to known methods, for example (Organic Chemistry Frontiers, 2021, Vol. 8, pp. 522-530; Chemistry A European Journal, 2006, Vol. 12, pp. 6592-6606; Journal of Materials Chemistry A, 2015, Vol. 3, pp. 878-885, etc.).

[0088] The reactions in steps 1 and 2 may be carried out in a reaction solvent. Preferred reaction solvents include: haloalkanes such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, and tetrachloroethane; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; heteroaromatic compounds such as imidazole, pyridine, pyrazine, and quinoline; and carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate. Examples of solvents include esters such as ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); sulfoxides such as dimethyl sulfoxide (DMSO); alcohols such as methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; and phenols such as phenol, naphthol, and cresol. These can be used individually or in any ratio, and there are no particular restrictions on the amount of solvent used. Among these, DMF, DMAc, pyridine, quinoline, and mixed solvents thereof are preferred in terms of good reaction yield.

[0089] Furthermore, the reaction in steps 1 and 2 can be accelerated by carrying out the reaction in the presence of a condensing agent. Examples of such condensing agents include solid acids such as alumina and silica gel; metal chlorides such as titanium tetrachloride, tin tetrachloride, and antimony pentachloride; organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, diazabicycloundecene, tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane; and carbodiimides such as 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, and 1,1'-carbonyldi(1,2,4-triazole). Of these, the condensing agent used in step 1 is more preferably triethylamine, pyridine, or EDC in that it yields a good reaction yield of the compound represented by formula (1a). Furthermore, the condensing agent used in step 2 is preferably an organic base in that it yields a good reaction yield of the imide compound represented by formula (1), and more preferably 1,4-diazabicyclo[2.2.2]octane.

[0090] The amount of condensing agent used is preferably in the range of 0.1 to 10 moles, and more preferably in the range of 0.5 to 5 moles, per mole of the compound represented by formula (1a) or the tetracarboxylic dianhydride represented by formula (4). The amount of amine compound represented by formula (6) used is preferably in the range of 1.0 to 1.2 moles, per mole of the compound represented by formula (1a), in terms of reaction yield and production efficiency. Furthermore, the amount of amine compound represented by formula (5) used is preferably in the range of 0.3 to 1.5 moles, and more preferably in the range of 0.5 to 1.1 moles, per mole of the tetracarboxylic dianhydride represented by formula (4).

[0091] The reaction temperature and reaction time vary depending on the amount of organic solvent and condensing agent used, but are usually selected from the ranges of -50 to 250°C and 1 to 48 hours, respectively. A reaction temperature of -20°C or higher is preferable for sufficient reaction, and a temperature of 180°C or lower is preferable for economic reasons. A reaction time of 1 to 24 hours is preferable.

[0092] <<Effects of Imide Compounds Having the Structure Represented by Formula (1)>> Imide compounds having the structure represented by formula (1) have a naphthalenetetracarboxylic acid diimide skeleton or a similar specific skeleton structure. Due to the strong electron-accepting properties of this skeleton, strong interaction with the HOMO orbital of an electron-donor hole transport material is expected. In other words, by containing the above imide compound (1) in a layer (e.g., a hole transport-promoting layer) in an organic electronic device (e.g., a photoelectric conversion device), the interaction between the LUMO orbital of the above imide compound (1) and the HOMO orbital of the adjacent hole transport layer is increased, and carrier transfer between the hole transport layer and the hole transport-promoting layer is expected to be promoted. Thus, because the above imide compound has an extremely deep LUMO level, it is expected that the exchange of holes between the hole transport layer and the electrode will be smoother. Furthermore, because the above imide compound has a naphthalenetetracarboxylic acid diimide skeleton or a similar specific skeleton structure, thermal stability and high reduction resistance can also be expected. In addition, the above imide compound has a six-membered ring structure with a substituent having a cyclic structure at the ortho position, as represented by formula (Q1). Therefore, the strength of the interaction with adjacent layers can be arbitrarily adjusted by appropriately selecting the substituent at the end. Furthermore, it is expected to suppress dark current and improve response speed when used in photoelectric conversion elements, as well as achieve a high glass transition temperature and suppress thermal decomposition during vacuum deposition. Moreover, it is expected to smooth the surface of films deposited by vacuum deposition and other methods.

[0093] As described above, the inventors have found that the imide compound represented by formula (1) can be effectively used as a hole transport promoting material to facilitate the exchange of holes between the hole transport layer and the electrode. They have also confirmed that when the imide compound represented by formula (1) (hole transport promoting material) is combined with a hole transport material in a photoelectric conversion element, the hole transport capability is enhanced. In other words, they have confirmed that the energy barrier when extracting carriers generated in the light-receiving layer to the electrode side in a photoelectric conversion element can be reduced by the imide compound represented by formula (1), which is the hole transport promoting material of this application.

[0094] (Hole Transport Promoting Material) The present invention relates to a hole transport promoting material represented by the following formula (2). In formula (2), Ar ２１ Ar ２２ represents any organic group. However, Ar ２１ or Ar ２２ At least one of these is represented by the following formula (Q2), and the following Cy is in the ortho position. ２ The ring B is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group to which the other groups are bonded. Ring B represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups, and may be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br.

[0095] Ar ２１ and Ar ２２ Of these, at least one is a group represented by formula (Q2) described below. Ar in formula (2) ２１ Ar ２２ These may be the same group or different groups. ２１ and Ar ２２ It is preferable that the group be the same because it is easy to synthesize. On the other hand, when used as a material for vapor deposition, Ar is used to suppress the vapor deposition temperature. ２１ and Ar ２２ It is preferable that the groups are different from each other. ２１ and Ar ２２ These are different groups, Ar ２２ If the group is represented by formula (Q2), then Ar ２１ It may have any organic group. In this case, Ar ２１ Ar ２２ The group may be represented by formula (Q2) with a different structure, or it may be a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heteroaromatic group, or an alkyl group which may have a cyclic structure. ２１ For example, R ２1 A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２1Preferred examples include heteroaromatic groups having 3 to 30 carbon atoms that may be substituted with , or alkyl groups having 1 to 30 carbon atoms that may have a branched or cyclic structure. The alkyl groups may have branched and cyclic structures. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be fused or linked rings of the aromatic hydrocarbon group and the heteroaromatic group. Considering the availability of raw materials and ease of synthesis, the above Ar ２１ R ２1 A phenyl group which may be substituted with R ２1 Naphthyl group, R may be substituted with ２1 A pyridyl group may be substituted with R ２1 A pyrazyl group which may be substituted with R ２1 A pyrimidyl group which may be substituted with R ２1 A triazyl group may be substituted with R ２1 A quinolyl group which may be substituted with R ２1Isoquinolyl group, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, heptyl group, hexyl group, cyclohexyl group, adamantyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylethyl group, diadamantylmethyl group, dicyclohexylmethyl group are preferred, and phenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, bistrifluoromethylphenyl group, biphenylyl group, cyanobiphenylyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanobiphenyl group, trifluoromethylbiphenylyl group Anonaphthyl group, fluoronaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, cyanopyrimidyl group, dicyanopyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, fluoroquinolyl group, difluoroquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, fluoroisoquinolyl group, or difluoroisoquinolyl group are more preferred.

[0096] Let's explain the base represented by formula (Q2). In formula (Q2), Cy ２ R ２１ This represents an organic group having a cyclic structure that may be substituted with X. ２１ ~X ２４ These are, independently, N, C-H, or C-R ２１ It represents.

[0097] Cy ２ R ２１ This represents an organic group having a cyclic structure which may be substituted with Cy. ２ The Cy １ Similar groups are cited as preferred examples.

[0098] A preferred example of the structure represented by formula (Q2) is, for example, an example similar to the example given for formula (Q1) above. Among the preferred examples of the structure represented by formula (Q2), substituents whose electron-withdrawing properties are enhanced by cyano groups or nitrogen-containing heteroaromatic compounds are preferred as hole transport promoting materials. In particular, (E-3), (E-4), (E-5), (E-6), (E-7), (E-19), (E-21), (E-22), (E-23), (E-24), (E-31), (E-59), (E-58), (E-76), (E-77), (E-109), (E-116), (E-126), and (E-127) are more preferred, and (E-5), (E-6), (E-7), (E-19), (E-23), and (E-77) having cyano groups are especially preferred.

[0099] In equations (2) and (Q2) explained above, R ２１ These include aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, and CF. ３ This represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms which may have a cyclic structure, and may also be a group formed by a combination of multiple substituents. The aromatic hydrocarbon group and the heteroaromatic group may be monocyclic, fused, or linked rings, and may be a fused or linked ring of the aromatic hydrocarbon group and the heteroaromatic group. ２１ A preferred example is the R １ Similar bases can be cited. Note that in equation (2), X ２１ ~X ２４ R joins as ２１ (C-R ２１ In R ２１ ), Ar ２１ and / or Ar ２２ When Cy is a base represented by formula (Q2) ２ R bonded ２１ , and also, Ar ２１ When R is a group other than the group represented by formula (Q2) ２１ They may be the same in part or in whole, or they may be different in part or in whole.

[0100] Ring B represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups, and may be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br. Preferred examples of ring B are (B-1) to (B-10) below. (B-1) or (B-2) is even more preferred as ring B in terms of superior hole transport promotion performance. (B-2) is even more preferred as ring B in terms of low raw material cost. (In formulas (B-1) to (B-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in ring B. １ When Z has １ These may be the same or different.

[0101] (Imide Compounds) The present invention relates to imide compounds represented by the following formula (3). In formula (3), Ar ３１ and Ar ３２ R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ This represents a heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure. However, Ar ３１ or Ar ３２ At least one of these is represented by the following formula (Q3), and the following Cy is in the ortho position. ３ The compound is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group to which C is bonded. Ring C represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups, and may be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br.

[0102] Ar ３１ Ar ３２ R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１This represents a heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with , or a cyclic or branched alkyl group having 1 to 30 carbon atoms. However, Ar ３１ or Ar ３２ At least one of them is a group represented by formula (Q3) described below. Ar in formula (3) ３１ Ar ３２ These may be the same group or different groups. ３１ and Ar ３２ It is preferable that the groups be the same in terms of ease of synthesis. On the other hand, when used as a material for vapor deposition, Ar is preferred in order to suppress the vapor deposition temperature. ３１ and Ar ３２ It is preferable that these are different groups from each other.

[0103] However, Ar ３１ and Ar ３２ The same group (Ar ３１ =Ar ３２ ) If Ar ３１ and Ar ３２ Preferably, it is not one of the following formulas (Q3-1), (Q3-2), or (Q3-3). Formula (Q3-1) has rotational isomers due to having two orthobiphenyl groups and lacks polar groups, making it difficult to efficiently synthesize a single component. Furthermore, formulas (Q3-2) and (Q3-3) have phenyl groups substituted with phenyl groups at positions 2 and 6, resulting in extremely low yields during synthesis. Thus, Ar ３１ and Ar ３２ If the formula is any of equations (Q3-1), (Q3-2), or (Q3-3), challenges tend to remain from the perspective of mass production.

[0104] Ar ３１ and Ar ３２ These are different groups, Ar ３２ If the base is represented by formula (Q3), then Ar ３１ These are aromatic hydrocarbon groups (cyano groups, CF) having 6 to 30 carbon atoms. ３ (may be substituted with F), heteroaromatic groups (cyano groups, CF) having 3 to 30 carbon atoms. ３It represents a group that is either substituted with F, or a combination of these. For example, Ar ３１ R ３１ A phenyl group which may be substituted with R ３１ Naphthyl group, R may be substituted with ３１ A pyridyl group may be substituted with R ３１ A pyrazyl group which may be substituted with R ３１ A pyrimidyl group which may be substituted with R ３１ A triazyl group may be substituted with R ３１ A quinolyl group which may be substituted with R ３１ Isoquinolyl group, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, heptyl group, hexyl group, cyclohexyl group, adamantyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylethyl group, diadamantylmethyl group, or dicyclohexylmethyl group, which may be substituted with Ar. ３１ These include phenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethylphenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, bistrifluoromethylphenyl group, biphenylyl group, cyanobiphenylyl group, trifluoromethylbiphenylyl group, naphthyl group, cyanonaphthyl group, fluoronaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, tetrafluoropyridyl group, trifluoromethylpyridyl group, and bistrifluoromethylphenyl group. It is even more preferable that the group is a lysyl group, pyrimidyl group, cyanopyrimidyl group, dicyanopyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, triazyl group, cyanotriazyl group, dicyanotriazyl group, bistrifluoromethyltriazyl group, quinolyl group, cyanoquinolyl group, trifluoromethylquinolyl group, fluoroquinolyl group, difluoroquinolyl group, isoquinolyl group, cyanoisoquinolyl group, trifluoromethylisoquinolyl group, fluoroisoquinolyl group, or difluoroisoquinolyl group. ３１ and Ar ３２When is an alkyl group, the alkyl group is not substituted. For example, Ar ３１ and Ar ３２ It is not an alkyl group having a cyano group (alkylcyano group).

[0105] Let's explain the base represented by formula (Q3). In equation (Q3), Cy ３ R ３１ This represents an organic group having a cyclic structure that may be substituted with X. ３１ ~X ３４ These are, independently, N, C-H, or C-R ３１ Represents R ３１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ This represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 3 to 30 carbon atoms having a cyclic structure, and may also be a group formed by a combination of multiple substituents.

[0106] Cy ３ R ３１ This represents an organic group having a cyclic structure which may be substituted with Cy. ３ The Cy １ Similar groups are cited as preferred examples.

[0107] Preferred examples of the structure represented by formula (Q3) are the same examples as those given for formula (Q1) above. Among the preferred examples of the structure represented by formula (Q3), (E-1), (E-3), (E-4), (E-5), (E-6), (E-7), (E-19), (E-21), (E-22), (E-23), (E-24), (E-31), (E-59), (E-58), (E-76), (E-77), (E-109), (E-110), (E-116), (E-124), (E-125), (E-126), and (E-127) are even more preferred because the raw materials are readily available and the synthesis is easy. In particular, (E-5), (E-6), (E-7), (E-19), (E-23), and (E-77) are especially preferred because the purification during synthesis is easy.

[0108] In equations (3) and (Q3) explained above, R ３１These include aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, and CF. ３ This represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 3 to 30 carbon atoms having a cyclic structure, and may also be a group formed by a combination of multiple substituents.

[0109] R ３１ is a cyano group, F, CF ３ Preferably, the group is a phenyl group, naphthyl group, pyridyl group, pyrazyl group, triazyl group, quinolyl group, isoquinolyl group, adamantyl group, cyclohexyl group, cyclopentyl group, cyclobutyl group, cyclopropyl group, or a combination thereof. In terms of good device performance, R ３１ This includes cyano group, trifluoromethyl group, phenyl group, cyanophenyl group, dicyanophenyl group, fluorophenyl group, difluorophenyl group, perfluorophenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, naphthyl group, cyanonaphthyl group, dicyanonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, bistrifluoromethylnaphthyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, fluoropyridyl group, difluoropyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, pyrimidi A cyclohexyl group, cyanopyrimidyl group, dicyanopyrimidyl group, fluoropyrimidyl group, difluoropyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group, pyrazyl group, cyanopyramyladyl group, dicyanopyramyladyl group, fluoropyramyladyl group, difluoropyramyladyl group, trifluoromethylpyramyladyl group, bistrifluoromethylpyramyladyl group, triazyl group, cyanotriazyl group, dicyanotriazyl group, fluorotriazyl group, difluorotriazyl group, trifluoromethyltriazyl group, bistrifluoromethyltriazyl group, adamantyl group, or cyclohexyl group is preferred. Considering the availability of raw materials and ease of synthesis, R ３１ The group is preferably a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a pyridyl group, or a cyanopyridyl group, with a cyano group being more preferred.

[0110] Ring C represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be a combination of multiple aromatic hydrocarbon rings linked directly or via linking groups. Preferred examples of ring C include (C-1) to (C-10) listed below. (C-1) or (C-2) are even more preferred as ring C in terms of superior hole transport promotion performance. (C-2) is even more preferred as ring C in terms of low raw material cost. (In formulas (C-1) to (C-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in the ring C. １ When Z has １ These may be the same or different.

[0111] <Embodiments> Examples of the stacked configuration of the organic electronic element (for example, a photoelectric conversion element) of the present invention include the following configurations (i) or (ii): (i): First electrode / hole transport promoting layer / hole transport layer / light receiving layer / second electrode (ii): First electrode / hole transport promoting layer / hole transport layer / light receiving layer / electron transport layer / second electrode Note that if the organic electronic element is, for example, an organic EL element, then in the above configuration (i) or (ii), the "light receiving layer" can be read as the "light emitting layer".

[0112] Hereinafter, the photoelectric conversion element and organic EL element according to the present invention will be described in more detail with reference to Figures 1 and 2, using the configuration described in (ii) above as an example. Figure 1 is a schematic cross-sectional view showing an example of the stacked configuration of the photoelectric conversion element according to the present invention, and Figure 2 is a schematic cross-sectional view showing an example of the organic EL element according to the present invention.

[0113] <<First Embodiment>> The photoelectric conversion element according to the first embodiment is an organic image sensor or photosensor having the stacked structure shown in Figure 1. The photoelectric conversion element 1 comprises a first electrode 11 (first electrode), a hole transport promoting layer 12, a hole transport layer 13, a light receiving layer 14, an electron transport layer 15, and a second electrode 16 (second electrode) in this order. However, some of these layers may be omitted, or other layers may be added.

[0114] In the photoelectric conversion element 1 shown in Figure 1, light is incident from above the transparent first electrode 11 and received by the light-receiving layer 14. For convenience, Figure 1 shows the light incident from the side of the light-receiving layer 14. Furthermore, a voltage is applied to the photoelectric conversion element 1 so that the holes (positive and negative charges) generated by photoelectric conversion in the light-receiving layer 14 are moved to the first electrode 11 and the electrons are moved to the second electrode 16. That is, the first electrode 11 is used as a hole-collecting electrode and the second electrode 16 is used as an electron-collecting electrode. Note that in Figure 1, the substrate provided on the upper surface of the first electrode 11 is omitted. There are no particular limitations on the substrate here, and examples include glass plates, quartz plates, plastic plates, etc. Also, in the configuration where light is incident from the substrate side, the substrate is transparent with respect to the wavelength of light. The above layers will be described below.

[0115] [First Electrode 11] A first electrode 11 or a second electrode 16 is provided on the substrate. In the case of a photoelectric conversion element configured such that light passes through the first electrode 11 and is incident on the light-receiving layer 14, the first electrode is formed of a transparent material that transmits or substantially transmits the light. Here, "transmits light" means that the average transmittance is 80% or more, and "substantially transmits light" means that the average transmittance is 50% or more. In other words, in this specification, "transparent" means that the average transmittance is 50% or more.

[0116] The transparent material used for the first electrode 11 or the second electrode 16 is not particularly limited, but examples include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, aluminum-doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide.

[0117] In the case of a photoelectric conversion element configured such that light enters the light-receiving layer 14 only from the second electrode 16 side, the transmission characteristics of the first electrode 11 are not important. Therefore, examples of materials that can be used for the first electrode in this case include gold, iridium, molybdenum, palladium, platinum, etc.

[0118] [Hole Transport Promoting Layer 12] A hole transport promoting layer 12 is provided between the first electrode 11 and the hole transport layer 13, which will be described later. The hole transport promoting layer 12 is provided to promote hole transport from the hole transport layer 13 to the first electrode 11. The hole transport promoting layer 12 contains an imide compound represented by formula (1) above. It is also possible to include compounds other than the imide compound represented by formula (1) together with the hole transport promoting layer 12. Examples of compounds that can be included in the hole transport promoting layer 12 include conventionally known hole transport materials, such as the compounds used in the hole transport layer 13 described later.

[0119] [Hole Transport Layer 13] A hole transport layer 13 is provided between the hole transport enhancement layer 12 and the light receiving layer 14. The hole transport layer 13 has the role of transporting holes generated in the light receiving layer 14 from the light receiving layer 14 to the first electrode 11, and blocking electrons generated in the light receiving layer 14 from moving toward the first electrode 11. Depending on the application, it may also have the role of blocking electron injection from the first electrode 11.

[0120] The hole transport layer 13 may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. The hole transport material that can be contained in the hole transport layer 13 may be a known hole transport material. Examples of known hole transport materials include aromatic tertiary amine compounds, naphthalene compounds, anthracene compounds, tetracene compounds, pentacene compounds, phenanthrene compounds, pyrene compounds, perylene compounds, fluorene compounds, carbazole compounds, indole compounds, pyrrole compounds, picene compounds, thiophene compounds, benzotrifuran compounds, benzotrithiophene compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodithiophene compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, crisenodithiophene compounds, benzothienobenzothiophene compounds, indolocarbazole compounds, and the like. Among these, fluorene compounds, carbazole compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, crisenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds are preferred, with fluorene compounds, carbazole compounds, crisenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds being particularly preferred.

[0121] [Light-receiving layer 14] A light-receiving layer 14 is provided between the hole transport layer 13 and the electron transport layer 15, which will be described later. The material for the light-receiving layer 14 is a material that has a photoelectric conversion function.

[0122] The light-receiving layer 14 may be a single-layer structure made of one or more materials, or a laminated structure made of multiple layers with the same or different compositions. In particular, in order to increase the photoelectric conversion efficiency, it is preferable that the light-receiving layer consists of layers containing at least two materials (organic components).

[0123] Examples of materials used in a light-receiving layer 14, which is a single-layer structure made of one type of material, include (i) coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, etc. Examples of materials used in a light-receiving layer 14, which is a single-layer structure made of two types of materials, include combinations of the aforementioned (i) coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, and (ii) fullerene and its derivatives, and other acceptor materials. The light-receiving layer 14 made of these materials may be formed by pre-mixing the powders and then depositing them, or by co-depositing them in any proportion. Examples of materials used in a light-receiving layer 14, which is a single-layer structure made of three types of materials, include combinations of the aforementioned (i) coumarin and its derivatives, quinacridone and its derivatives, phthalocyanine and its derivatives, (ii) fullerene and its derivatives, other acceptor materials, and (iii) hole transport materials. The light-receiving layer 14, made of these materials, may be formed by pre-mixing the powders and then depositing them, or by co-depositing them in any proportion.

[0124] (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 imide compounds and specific examples of hole transport materials are the same as those used in the hole transport layer 13 described above.

[0125] Furthermore, the material having photoelectric conversion functionality is not limited to being contained only in the light-receiving layer. For example, the material having photoelectric conversion functionality may also be contained in a layer adjacent to the light-receiving layer 14 (the hole transport layer 13 or the electron transport layer 15).

[0126] [Electron Transport Layer 15] An electron transport layer 15 is provided between the light-receiving layer 14 and the second electrode 16, which will be described later. The electron transport layer 15 has the role of transporting electrons generated in the light-receiving layer 14 to the second electrode 16, and blocking the movement of holes from the second electrode 16 to the light-receiving layer 14. Depending on the application, it may also have the role of blocking hole injection from the second electrode 16.

[0127] Furthermore, the electron transport material that can be contained in the electron transport layer 15 may be a known electron transport material, and examples of electron transport materials include fullerene, fullerene derivatives, triazine derivatives, bis(8-hydroxyquinolinate)manganese, tris(8-hydroxyquinolinate)aluminum, tris(2-methyl-8-hydroxyquinolinate)aluminum, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bp Examples include hen(4,7-diphenyl-1,10-phenanthroline), BAlq(bis(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum), 4,6-bis(3,5-di(pyridine-4-yl)phenyl)-2-methylpyrimidine, N,N'-diphenyl-1,4,5,8-naphthalenetetracarboxylic acid diimide, and N,N'-di(4-pyridyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide.

[0128] The electron transport layer 15 may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions.

[0129] [Second Electrode 16] A second electrode 16 is provided on the electron transport layer 15. The material of the second electrode 16 may be, for example, indium-tin oxide (ITO), indium-zinc oxide (IZO), sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ２ O ３Examples include mixtures, indium, lithium / aluminum mixtures, gold, platinum, rare earth metals, molybdenum oxide, etc. The first electrode 11 and the second electrode 16 may be the same or different.

[0130] [Method for forming each layer] Each layer, excluding the first electrode 11 and the second electrode 16 described above, can be formed by thinning the material of each layer (along with binder resin and other materials and solvents as needed) using known methods such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett method. There are no particular restrictions on the thickness of each layer formed in this way, and it can be appropriately selected depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0131] The first electrode 11 and the second electrode 16 can be formed by thinning the electrode material using methods such as vapor deposition or sputtering. A pattern may be formed via a mask of a desired shape during vapor deposition or sputtering, or a pattern of a desired shape may be formed by photolithography after the thin film has been formed by vapor deposition or sputtering.

[0132] The film thickness of the first electrode 11 and the second electrode 16 is preferably 1 μm or less, and more preferably 10 nm to 200 nm.

[0133] The first electrode 11 and the second electrode 16 may be made of different materials as needed (this is also called an inverse structure). In such a structure, the light passes through the second electrode 16 and enters the light-receiving layer 14, resulting in a photoelectric conversion element.

[0134] The image sensor equipped with the photoelectric conversion element of this embodiment can be applied, for example, to the image sensors of digital cameras and digital video cameras, and to the image sensors built into mobile phones, etc. The light sensor can be applied, for example, to television remote controls, air conditioner switches, automatic door opening and closing, etc.

[0135] <<Second Embodiment>> The photoelectric conversion element according to the second embodiment of the present invention is a solar cell having the stacked structure shown in Figure 1. The solar cell 1 has a hole transport promoting layer 12 and a hole transport layer 13 between the first electrode 11 and the light receiving layer 14, and an electron transport layer 15 between the second electrode 16 and the light receiving layer 14. However, some of these layers may be omitted, or other layers may be added.

[0136] [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).

[0137] [Hole Transport Promoting Layer 12] The material of the hole transport promoting layer 12 is the same as the material of the hole transport promoting layer 12 in the first embodiment (an imide compound represented by formula (1)). The material of the hole transport promoting layer 12 may also contain conventionally known hole transport materials in addition to the material in the first embodiment.

[0138] [Hole Transport Layer 13] The material of the hole transport layer 13 is the same as the material of the hole transport layer 13 in the first embodiment. In addition to the hole transport material in the first embodiment, the material of the hole transport layer 13 may also contain conventionally known hole transport materials.

[0139] [Light-receiving layer 14] The material of the light-receiving layer 14 may be any material using an electron-donating material and an electron-accepting material, and may be a planar-bonded type in which the electron-donating material and the electron-accepting material are bonded to each other in a planar manner, or a bulk hetero-bonded type in which the electron-donating material and the electron-accepting material are mixed and formed into a film. The electron-donating material is not particularly limited, but an organic semiconductor is preferred. Examples of electron-donating materials include polymer compounds such as polythiophene derivatives, polyfluorene derivatives, and polyphenylene vinylene derivatives and copolymers thereof, or low molecular weight compounds such as phthalocyanine derivatives and their metal complexes, porphyrin derivatives and their metal complexes, acene derivatives such as pentacene, and diamine derivatives. The electron-donating material may also be an inorganic semiconductor in addition to an organic semiconductor, as long as it does not impair the effects of the present invention. The electron-accepting material is not particularly limited, but an organic semiconductor is preferred. Examples of electron-accepting materials include fullerene derivatives, perylene derivatives, and naphthalene derivatives.

[0140] [Electron Transport Layer 15] The material for the electron transport layer 15 can be the electron transport material from the first embodiment. Alternatively, alkali metal halides such as sodium fluoride and cesium fluoride, alkaline earth metal halogen compounds such as calcium fluoride, carbonates such as cesium carbonate, and inorganic n-type semiconductors such as titanium dioxide and zinc oxide may be used as the electron transport material.

[0141] [Second Electrode 16] The second electrode 16 may be, but is not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof.

[0142] The first electrode 11 and the second electrode 16 may be made of different materials as needed (this is also called an inverse structure). In such a structure, the light passes through the second electrode 16 and enters the light-receiving layer 14, resulting in a photoelectric conversion element.

[0143] [Method for forming each layer] The method for forming each layer is not particularly limited. For example, the first electrode 11, hole transport enhancement layer 12, hole transport layer 13, light receiving layer 14, electron transport layer 15, and second electrode 16 may be sequentially laminated on a substrate using a vapor deposition method, spin coating method, casting method, pattern transfer method, etc. Alternatively, after laminating the hole transport enhancement layer 12, hole transport layer 13, light receiving layer 14, and electron transport layer 15, the first electrode 11 and second electrode 16 may be formed on this laminate by transfer, vapor deposition, sputtering, etc., respectively.

[0144] <<Third Embodiment>> The organic electronic element according to the third embodiment of the present invention is an organic EL element having the stacked structure shown in Figure 2. That is, the organic EL element 2 is provided with a first electrode 21, a hole injection layer 22, a hole transport layer 23, a light-emitting layer 24, an electron transport layer 25, and a second electrode 26 in this order. However, some of these layers may be omitted, or other layers may be added.

[0145] [First Electrode 21] The first electrode 21 has the role of injecting holes from the hole transport layer to the light-emitting layer. The first electrode 21 can be, but is not limited to, transparent electrodes such as indium tin oxide (ITO), indium zinc oxide (IZO), gold, silver, platinum, and copper, metals and alloys such as aluminum, molybdenum, chromium, and nickel, polythiophene derivatives and polyaniline derivatives that have high charge transport properties.

[0146] The organic electronic device may emit light from either side of the first electrode 21 and the second electrode 26, or from both sides. The electrode that extracts light is formed from a transparent material such as ITO or IZO. For convenience, Figure 2 shows the light being emitted from the side of the light-emitting layer 24.

[0147] [Hole Injection Layer 22] A hole injection layer 22 is provided between the first electrode 21 and the hole transport layer 23, which will be described later. The hole injection layer 22 is provided to promote hole transport from the first electrode 21 to the hole transport layer 23. The hole injection layer 22 contains an imide compound represented by formula (1) above as a hole injection material. The hole injection layer 22 may also contain compounds other than the imide compound represented by formula (1) above. Examples of compounds that can be contained in the hole injection layer 22 include conventionally known hole transport materials.

[0148] [Hole Transport Layer 23] A hole transport layer 23 is provided between the hole injection layer 22 and the light-emitting layer 24. The hole transport layer 23 has the role of transporting holes injected from the first electrode 21 to the light-emitting layer 24. The hole transport layer 23 may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. The hole transport material that can be contained in the hole transport layer 23 may be the same as the material of the hole transport layer 13 in the first embodiment.

[0149] [Emitting layer 24] The emissive layer 24 plays a role in generating light (phosphorescence or fluorescence) by the recombination of holes injected from the first electrode 21 and electrons injected from the second electrode 26, and includes an emissive material and, if necessary, an emissive host material. The emissive material and the emissive host material can be appropriately selected from known materials. Examples of luminescent materials and luminescent host materials include carbon condensed ring dyes such as triazine derivatives (including TADF materials substituted with carbazole, etc.), pyrimidine derivatives, carbazole derivatives, anthracene derivatives, tetracene derivatives, pyrene derivatives, rubrene derivatives, and decacycline derivatives; perylene derivatives such as perylenediimide, xanthene dyes such as rhodamine B, cyanine dyes, coumarin dyes such as coumarin 6 and C545T, quinacridone dyes such as Qd4 and DEQ, squarium dyes, styryl dyes, pyrazolone derivatives, phenoxazone dyes such as NileRed, carbazole, triarylamine, and tris(2-phenylpyridine). Examples of iridium complexes include, but are not limited to, iridium(III) (Ir(ppy)3), tris[2-phenyl-4-(2-ethylcyclohexyloxy)pyridine]iridium(III) (Ir(ehppy)3), aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrin zinc complexes, europium complexes, metal complexes composed of a central metal made of Al, Zn, Be or rare earth metals such as Tb, Eu, Dy, and ligands such as oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, and quinoline structures.

[0150] [Electron Transport Layer 25] The electron transport layer 25 is provided between the second electrode and the light-emitting layer and has the function of transporting electrons injected from the second electrode to the light-emitting layer, and includes an electron transport material. Examples of electron transport materials include, but are not limited to, triazine derivatives, tris(8-quinolinolato)aluminum (Alq3), bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminum (BAlq), 1,4,4'-bis(2,2'-diphenylvinyl)-1,1'-bipheny (DPVBi), (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole) (PBD), triazole derivatives (TAZ), basocuproine (BCP), silole derivatives, etc.

[0151] [Second Electrode 26] The second electrode 26 has the role of injecting electrons from the electron transport layer 25 to the light-emitting layer 24. The second electrode 26 can be made of aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium, cesium-doped ITO, etc., but is not limited to these.

[0152] [Method for Forming Each Layer] The method for forming each layer of the organic EL element 2 is as follows: First, a thin film made of the material for the first electrode 21 is formed on a suitable translucent substrate (not shown) by methods such as vapor deposition and sputtering. A hole injection layer 22 and a hole transport layer 23 are then deposited on the first electrode 21 in this order. The hole injection layer 22 and the hole transport layer 23 can be deposited by methods such as vacuum deposition, spin coating, casting, and LB. Next, an emissive layer 24 is provided on the hole transport layer 23. The emissive layer 24 can also be formed by thinning an organic emissive material using a desired organic emissive material by methods such as vacuum deposition, sputtering, spin coating, and casting. Next, an electron transport layer 25 is formed on the emissive layer 24. The electron transport layer 25 can be formed by the same method as the hole transport layer and the emissive layer. Finally, a second electrode 26 is laminated on the electron transport layer 25. The second electrode 26 can be formed from a desired metal material by methods such as vapor deposition and sputtering. The method for forming each layer of an organic EL element is not limited to the method described above. For example, known methods such as vacuum deposition, molecular beam deposition (MBE), dipping using a solution of the material dissolved in a solvent, spin coating, casting, bar coating, roll coating, and other coating methods can be appropriately employed.

[0153] The organic electronic elements (photoelectric conversion elements, organic EL elements, etc.) of the present invention, and the methods for forming each layer of the elements, are not limited to the elements and methods shown in the embodiments described above. For example, the materials of the first electrode, the light-receiving layer (or light-emitting layer), the electron transport layer, and the second electrode can be appropriately replaced with other known materials. Furthermore, the hole injection layer and the hole transport layer can be replaced with layers formed by mixing an imide compound represented by formula (1) with a hole transport material.

[0154] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. The obtained imide compound is １ Identification was made based on the H-NMR spectrum (400 MHz). １ For the measurement of the H-NMR spectrum, a Bruker Ascend 400 (400 MHz; manufactured by BRUKER) was used. １The H-NMR spectrum is deuterated chloroform (CDCl). ３ ) or didimethyl sulfoxide (DMSO-d ６ The measurement was performed using ) as the solvent and tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0155] (Synthesis Example 1: Synthesis of Imide Compound (D-10)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (4.40 g, 16.4 mmol), 2'-amino[1,1'-biphenyl]-4-carbonitrile (7.01 g, 36.1 mmol), and 1,4-diazabicyclo[2.2.2]octane (1.84 g, 16.4 mmol) were suspended in N,N-dimethylformamide (82 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, 100 mL of water and 100 mL of ethanol were added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-10) as a pale yellow solid (5.80 g, yield 57%). １ H-NMR (DMSO-d6) δ (ppm): 8.62 (s, 4H), 7.72 (d, J = 8.7Hz, 4H), 7.65-7.68 (m, 4H), 7.56-7.61 (m, 4H), 7.40 (d, J = 8.7Hz, 4H).

[0156] (Synthesis Example 2: Synthesis of Imide Compound (D-34)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.70 g, 6.34 mmol), 4-(4-amino-3-pyridinyl)benzonitrile (2.72 g, 13.9 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.711 g, 6.34 mmol) were suspended in N,N-dimethylformamide (49 mL) and stirred at 140°C for 7 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-34) as a white solid (2.90 g, yield 73%). １H-NMR (DMSO-d6) δ (ppm): 8.91 (d, J = 5.3 Hz, 2H), 8.86 (brs, 2H), 8.66 (s, 4H), 7.78 (d, J=8.5Hz, 4H), 7.71 (d, J=5.3Hz, 2H), 7.49 (d, J=8.5Hz, 4H).

[0157] (Synthesis Example 3: Synthesis of Imide Compound (D-139)) Under an argon atmosphere, 4-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isochromeno[6,5,4-def]isoquinoline-7-yl)benzonitrile (1.42 g, 3.84 mmol), 4-(4-amino-3-pyridinyl)benzonitrile (900 mg, 4.61 mmol), and 1,4-diazabicyclo[2.2.2]octane (215 mg, 1.92 mmol) were suspended in N,N-dimethylformamide (38 mL) and stirred at 120°C for 4 hours. After cooling to room temperature, the low-boiling components were removed by distillation, and the resulting solid was purified by recrystallization (N,N-dimethylformamide / toluene) to obtain the target imide compound (D-139) as a pale yellow solid (yield 2.05 g, 98%). １ H-NMR (DMSO-d ６ ) δ (ppm): 8.91 (d, J = 5.2 Hz, 1 H), 8.86 (d, J = 0.6 Hz, 1 H), 8.69 (m, 4 H), 8.07 (d, J = 8.7 H z, 2H), 7.80 (dd, J=5.2, 0.6Hz, 1H), 7.78 (m, 2H), 7.68 (d, J=8.7Hz, 2H), 7.48 (m, 2H).

[0158] (Synthesis Example 4: Synthesis of Imide Compound (D-152)) Under an argon atmosphere, 4-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isochromeno[6,5,4-def]isoquinoline-7-yl)benzonitrile (1.47 g, 4.00 mmol), 4-amino-3-(4-pyridinyl)benzonitrile (937 mg, 4.80 mmol), and 1,4-diazabicyclo[2.2.2]octane (224 mg, 2.00 mmol) were suspended in N,N-dimethylformamide (40 mL) and stirred at 120°C for 5 hours. After cooling to room temperature, the solvent was removed by vacuum distillation, and toluene was added and the mixture was stirred at room temperature for 30 minutes to precipitate a solid. The obtained solid was recovered by filtration and washed with toluene. The recovered solid was purified by recrystallization (N,N-dimethylformamide / toluene) to obtain the target imide compound (D-152) as a pale yellow solid (yield 1.57 g, yield 72%). １ H-NMR (CDCl ３ ) δ (ppm): 8.82 (d, J = 8.0Hz, 2H), 8.75 (d, J = 8.0Hz, 2H), 8.53-8.43 (m, 2H), 7.95 (dd, J = 8.0, 2.0Hz, 1H), 7.9 1-7.85 (m, 2H), 7.83 (d, J = 2.0Hz, 1H), 7.56 (d, J = 8.0Hz, 1H), 7.46 (d, J = 8.0Hz, 2H), 7.22 (d, J = 8.0Hz, 2H).

[0159] (Synthesis Example 5: Synthesis of Imide Compound (D-36)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.93 g, 7.20 mmol), 3-(4-amino-3-pyridinyl)benzonitrile (3.09 g, 15.8 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.81 g, 7.2 mmol) were suspended in N,N-dimethylformamide (72 mL) and stirred at 140°C for 7 hours. After cooling to room temperature, 72 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-36) as a pale red solid (2.50 g, yield 56%). １H-NMR (DMSO-d6) δ (ppm): 8.90 (d, J = 5.2 Hz, 2H), 8.87 (s, 2H), 8.67 (s, 4H), 7.78 (dd, J = 1.7, 0.6 Hz, 2H), 7.7 4 (dd, J=7.7, 1.3Hz, 2H), 7.71 (dd, J=5.1, 0.5Hz, 2H), 7.58 (dd, J=7.8, 1.5Hz, 2H), 7.47 (brd, J=7.8Hz, 2H).

[0160] (Synthesis Example 6: Synthesis of Imide Compound (D-12)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.88 g, 7.01 mmol), 2'-amino[1,1'-biphenyl]-3-carbonitrile (7.01 g, 15.4 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.79 g, 7.01 mmol) were suspended in N,N-dimethylformamide (35 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, 35 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-12) as a pale yellow solid (1.50 g, yield 34%). １ H-NMR (DMSO-d6) δ (ppm): 8.63 (s, 4H), 7.64-7.68 (m, 8H), 7.59-7.62 (m, 4H), 7.51 (ddd, J = 7.8, 2.0, 1.3Hz, 2H), 7.41 (t, J = 7.8Hz, 2H).

[0161] (Synthesis Example 7: Synthesis of Imide Compound (D-22)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.00 g, 7.46 mmol), 4-(3-amino-2-pyridinyl)benzonitrile (3.20 g, 16.4 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.84 g, 7.46 mmol) were suspended in N,N-dimethylformamide (75 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, 150 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-22) as a white solid (1.50 g, yield 32%).１ H-NMR (DMSO-d6) δ (ppm): 8.88 (dd, J = 4.8, 1.6 Hz, 2H), 8.68 (s, 4H), 8 .10 (dd, J=8.0, 1.6Hz, 2H), 7.75-7.78 (m, 6H), 7.59 (d, J=8.6Hz, 4H).

[0162] (Synthesis Example 8: Synthesis of Imide Compound (D-46)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.00 g, 7.46 mmol), 2-amino[1,1'-biphenyl]-4,4'-dicarbonitrate (3.93 g, 17.9 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.84 g, 7.46 mmol) were suspended in N,N-dimethylformamide (75 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-46) as a white solid (1.60 g, yield 32%). １ H-NMR (DMSO-d6) δ (ppm): 8.66 (s, 4H), 8.19 (dd, J = 8.1, 1.8Hz, 2H), 8.13 (d, J = 1 .8Hz, 2H), 7.85 (d, J=8.1Hz, 2H), 7.78 (d, J=8.4Hz, 4H), 7.44 (d, J=8.4Hz, 4H).

[0163] (Synthesis Example 9: Synthesis of Imide Compound (D-58)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.31 g, 8.60 mmol), 2-amino[1,1'-biphenyl]-5,4'-dicarbonitric acid (4.15 g, 18.9 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.96 g, 8.60 mmol) were suspended in N,N-dimethylformamide (86 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, 100 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-58) as a white solid (3.20 g, yield 55%). １H-NMR (DMSO-d6) δ (ppm): 8.64 (s, 4H), 8.19 (dd, J = 8.3, 1.7Hz, 2H), 8.16 (d, J = 1 .7Hz, 2H), 7.84 (d, J=8.3Hz, 2H), 7.76 (d, J=8.6Hz, 4H), 7.45 (d, J=8.6Hz, 4H).

[0164] (Synthesis Example 10: Synthesis of Imide Compound (D-38)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (5.66 g, 21.1 mmol), 2-amino[1,1'-biphenyl]-4-carbonitrile (9.02 g, 46.4 mmol), and 1,4-diazabicyclo[2.2.2]octane (2.37 g, 21.1 mmol) were suspended in N,N-dimethylformamide (211 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, 200 mL of ethanol and 200 mL of water were added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-38) as a white solid (4.70 g, yield 36%). １ H-NMR (DMSO-d6) δ (ppm): 8.64 (s, 4H), 8.13 (dd, J = 8.0, 1.8Hz, 2H), 8.07 (d, J = 1.7Hz, 2H), 7.79 (d, J = 8.0Hz, 2H), 7.22-7.26 (m, 10H).

[0165] (Synthesis Example 11: Synthesis of Imide Compound (D-2)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.71 g, 10.1 mmol), 2-aminobiphenyl (3.76 g, 22.2 mmol), and 1,4-diazabicyclo[2.2.2]octane (1.13 g, 10.1 mmol) were suspended in N,N-dimethylformamide (50 mL) and stirred at 140°C for 13 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-2) (3.20 g, yield 56%). １ H-NMR (DMSO-d6) δ (ppm): 8.60 (s, 4H), 7.50-7.64 (m, 8H), 7.12-7.26 (m, 10H).

[0166] (Synthesis Example 12: Synthesis of Imide Compound (D-20)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (3.19 g, 11.9 mmol), [2,4'-bipyridine]-3-amine (4.49 g, 26.2 mmol), and 1,4-diazabicyclo[2.2.2]octane (1.33 g, 11.9 mmol) were suspended in N,N-dimethylformamide (119 mL) and stirred at 140°C for 10 hours. After cooling to room temperature, 250 mL of ethanol was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with acetic acid to obtain the target imide compound (D-20) as a white solid (1.20 g, yield 18%). １ H-NMR (DMSO-d6) δ (ppm): 8.89 (dd, J = 4.8, 1.5 Hz, 2H), 8.69 (s, 4H), 8.48 (dd, J = 4.4, 1.7 Hz, 4H), 8.11 (dd, J=8.1, 1.5Hz, 2H), 7.78 (dd, J=8.1, 4.8Hz, 2H), 7.39 (dd, J=4.4, 1.6Hz, 4H).

[0167] (Synthesis Example 13: Synthesis of Imide Compound (D-8)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.57 g, 9.60 mmol), 2-(4-pyridinyl)benzeneamine (3.60 g, 21.1 mmol), and 1,4-diazabicyclo[2.2.2]octane (1.08 g, 9.60 mmol) were suspended in N,N-dimethylformamide (96 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, 100 mL of ethanol and 100 mL of water were added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF to obtain the target imide compound (D-8) as a white solid (1.10 g, yield 20%). １ H-NMR (DMSO-d6) δ (ppm): 8.63 (s, 4H), 8.41 (dd, J = 4.3, 1.6Hz, 4H), 7.66-7.69 (m, 4H), 7.58-7.62 (m, 4H), 7.21 (dd, J = 4.3, 1.6Hz, 4H).

[0168] (Synthesis Example 14: Synthesis of Imide Compound (D-32)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (268 mg, 1.00 mmol), [3,4'-bipyridine]-4-amine (377 mg, 2.20 mmol), and 1,4-diazabicyclo[2.2.2]octane (112 mg, 1.00 mmol) were suspended in N,N-dimethylformamide (10 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with toluene to obtain the target imide compound (D-32) as a white solid (420 mg, yield 73%). １ H-NMR (DMSO-d6) δ (ppm): 8.92 (d, J = 5.2 Hz, 2H), 8.88 (d, J = 0.6 Hz, 2H), 8.67 (s, 4H ), 8.48 (dd, J=4.3, 1.7Hz, 4H), 7.72 (d, J=7.7Hz, 2H), 7.31 (dd, J=4.3, 1.7Hz, 4H).

[0169] (Synthesis Example 15: Synthesis of Imide Compound (D-353)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.40 g, 5.22 mmol), 2-(4-quinolyl)benzeneamine (2.53 g, 11.5 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.59 g, 5.22 mmol) were suspended in N,N-dimethylformamide (52 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target imide compound (D-353) as a pale yellow solid (2.27 g, yield 65%). １ H-NMR (DMSO-d6) δ (ppm): 8.62 (dd, J = 4.3, 1.8 Hz, 2H), 8.35 (brs, 4H), 8.13 (dd, J = 8.6, 1.8 Hz, 2H), 7.74 (dd, J = 8.2, 1 .5Hz, 2H), 7.56-7.62 (m, 8H), 7.51 (dd, J=7.1, 1.5Hz, 2H), 7.40 (dd, J=8.3, 7.2Hz, 2H), 7.28 (dd, J=8.6, 4.2Hz, 2H).

[0170] (Synthesis Example 16: Synthesis of Imide Compound (D-44)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.71 g, 10.1 mmol), 3-amino-4-(4-pyridyl)benzonitrile (4.31 g, 22.1 mmol), and 1,4-diazabicyclo[2.2.2]octane (1.13 g, 10.1 mmol) were suspended in N,N-dimethylformamide (101 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with DMF and acetic acid to obtain the target imide compound (D-44) as a pale yellow solid (2.80 g, yield 45%). １ H-NMR (DMSO-d6) δ (ppm): 8.67 (s, 4H), 8.47 (dd, J = 4.5, 1.6Hz, 4H), 8.20 (dd, J = 8.1, 1. 7Hz, 2H), 8.15 (brd, J=1.7Hz, 2H), 7.87 (d, J=8.1Hz, 2H), 7.23 (dd, J=4.5, 1.6Hz, 4H).

[0171] (Synthesis Example 17: Synthesis of imide compound (D-224)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (320 mg, 1.19 mmol), 2-(9-phenantrenyl)benzeneamine (707 mg, 2.63 mmol), and 1,4-diazabicyclo[2.2.2]octane (134 mg, 1.19 mmol) were suspended in N,N-dimethylformamide (11.8 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was purified with ethanol and hexane to obtain the target imide compound (D-224) as a pale yellow solid (590 mg, yield 64%). １ H-NMR (DMSO-d6) δ (ppm): 8.64-8.70 (m, 4H), 8.52 (s, 1H), 8.40, (d, J =7.6Hz, 1H), 8.24 (d, J = 7.5Hz, 1H), 8.11 (s, 1H), 7.46-7.73 (m, 22H).

[0172] (Synthesis Example 18: Synthesis of imide compound (D-218)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.16 g, 4.33 mmol), 4'-(1-adamantyl)-1,1'-biphenyl-2-amine (2.89 g, 9.52 mmol), and 1,4-diazabicyclo[2.2.2]octane (485 mg, 4.33 mmol) were suspended in N,N-dimethylformamide (43.4 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with toluene, ethanol, and hexane, and then purified by recrystallization with toluene to obtain the target imide compound (D-218) as a pale yellow solid (1.11 g, yield 31%). １ H-NMR (DMSO-d6) δ (ppm): 8.64 (s, 4H), 7.50-7.62 (m, 8H), 7.16-7.22 (m, 8H), 1.94 (brs, 6H), 1.59-1.67 (m, 24H).

[0173] (Synthesis Example 19: Synthesis of imide compound (D-230)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (290 mg, 1.08 mmol), 2-(4-phenyl-1-naphthalenyl)benzeneamine (703 mg, 2.38 mmol), and 1,4-diazabicyclo[2.2.2]octane (121 mg, 1.08 mmol) were suspended in N,N-dimethylformamide (10.8 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was washed with ethanol and hexane to obtain the target imide compound (D-230) as a pale yellow solid (710 mg, yield 80%). Mass spectrometry (FD-MS): 822 (M+)

[0174] (Synthesis Example 20: Synthesis of imide compound (D-232)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (580 mg, 2.16 mmol), 4'-(1-naphthalenyl)-[1,1'-biphenyl]-2-amine (1.41 g, 4.76 mmol), and 1,4-diazabicyclo[2.2.2]octane (243 g, 2.16 mmol) were suspended in N,N-dimethylformamide (21.5 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was washed with ethanol and hexane to obtain the target imide compound (D-232) as a pale yellow solid (920 mg, yield 52%). １ H-NMR (DMSO-d6) δ (ppm): 8.68 (s, 4H), 7.94 (brd, J = 8.3Hz, 2H), 7.88 (d, J = 8.3Hz, 2H), 7.60-7.67 (m, 6H), 7.56 (brd, J=7.7Hz, 2H), 7.45-7.51 (m, 4H), 7.32-7.39 (m, 8H), 7.28 (d, J=7.3Hz, 4H), 7.23 (dd, J=7.1, 1.1Hz, 2H).

[0175] (Synthesis Example 21: Synthesis of imide compound (D-62)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.20 g, 4.47 mmol), 2-(1-naphthalenyl)benzeneamine (2.16 g, 9.84 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.50 g, 4.47 mmol) were suspended in N,N-dimethylformamide (45.0 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with toluene, ethanol, and hexane to obtain the target imide compound (D-62) as a pale yellow solid (2.38 g, yield 79%). Mass spectrometry (FD-MS): 670 (M+)

[0176] (Synthesis Example 22: Synthesis of imide compound (D-267)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.00 g, 7.46 mmol), 2-(2-naphthalenyl)benzeneamine (3.60 g, 16.4 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.84 g, 7.46 mmol) were suspended in N,N-dimethylformamide (37.3 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with ethanol, hexane, and toluene to obtain the target imide compound (D-267) as a pale yellow solid (0.67 g, yield 48%). １ H-NMR (DMSO-d6) δ (ppm): 8.55 (s, 4H), 7.54-7.77 (m, 16H), 7.28-7.46 (m, 4H).

[0177] (Synthesis Example 23: Synthesis of imide compound (D-206)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (140 mg, 0.52 mmol), 3-(1-naphthalenyl)-2-pyridineamine (253 mg, 1.15 mmol), and 1,4-diazabicyclo[2.2.2]octane (58.6 mg, 0.52 mmol) were suspended in N,N-dimethylformamide (5.2 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was washed with ethanol and hexane to obtain the target imide compound (D-206) as a pale yellow solid (300 mg, yield 86%). Mass spectrometry (FD-MS): 672 (M+)

[0178] (Synthesis Example 24: Synthesis of Imide Compound (D-268)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.40 g, 8.95 mmol), 3-(2-naphthalenyl)-2-pyridineamine (4.33 g, 19.7 mmol), and 1,4-diazabicyclo[2.2.2]octane (1.00 g, 8.95 mmol) were suspended in N,N-dimethylformamide (89.5 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with ethanol, hexane, and toluene to obtain the target imide compound (D-268) as a pale yellow solid (2.38 g, yield 40%). １ H-NMR (DMSO-d6) δ (ppm): 8.76 (dd, J = 4.8, 1.8 Hz, 2H), 8.60 (s, 4H), 8.18 (dd, J = 7.7, 1.9 Hz, 2 H), 7.87 (brs, 2H), 7.76-7.83 (m, 8H), 7.45 (dd, J=6.4, 3.2, 4H), 7.37 (dd, J=8.6, 1.8Hz, 2H).

[0179] (Synthesis Example 25: Synthesis of Imide Compound (D-228)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.00 g, 7.46 mmol), [1,1':4',1''-terphenyl]-2-amine (4.03 g, 16.4 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.84 g, 7.46 mmol) were suspended in N,N-dimethylformamide (74.6 mL) and stirred at 140°C for 9 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with toluene, ethanol, and hexane to obtain the target imide compound (D-228) as a pale yellow solid (2.38 g, yield 48%). １ H-NMR (DMSO-d6) δ (ppm): 8.62 (s, 4H), 7.51-7.64 (m, 14H), 7.28-7.43 (m, 12H).

[0180] (Synthesis Example 26: Synthesis of imide compound (D-341)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.10 g, 4.14 mmol), 2-(2-quinolinyl)benzeneamine (2.01 g, 9.11 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.46 g, 4.14 mmol) were suspended in N,N-dimethylformamide (41.3 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with ethanol and hexane, and then purified by recrystallization with DMF and acetic acid to obtain the target imide compound (D-341) as a pale yellow solid (1.76 g, yield 63%). １ H-NMR (DMSO-d6) δ (ppm): 8.62 (s, 4H), 8.35 (d, J = 8.7Hz, 2H), 8.05-8.07 (m, 2H ), 7.83-7.86 (m, 4H), 7.66-7.74 (m, 6H), 7.39-7.42 (m, 4H), 7.92-7.94 (m, 2H).

[0181] (Synthesis Example 27: Synthesis of Imide Compound (D-343)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.42 g, 5.29 mmol), [3,4'-bipyridine]-2-amine (1.99 g, 11.6 mmol), and triethoxyvinylsilane (1.01 g, 5.29 mmol) were suspended in N,N-dimethylformamide (53.1 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with toluene and hexane, and then purified by recrystallization using DMF and toluene to obtain the target imide compound (D-343) as a pale yellow solid (2.31 g, yield 76%). １ H-NMR (DMSO-d6) δ (ppm): 8.81 (dd, J = 4.9, 1.7 Hz, 2H), 8.67 (s, 4H), 8.49 (dd, J = 4.4, 1.7 Hz, 4H), 8.17 (dd, J=7.9, 1.7Hz, 2H), 7.81 (dd, J=7.8, 4.8Hz, 2H), 7.30 (dd, J=4.4, 1.7Hz, 4H).

[0182] (Synthesis Example 28: Synthesis of imide compound (D-344)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.35 g, 8.76 mmol), [3,3'-bipyridine]-2-amine (3.30 g, 19.3 mmol), and triethoxyvinylsilane (1.67 g, 8.76 mmol) were suspended in N,N-dimethylformamide (43.8 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with ethanol and hexane, and then purified by recrystallization using toluene to obtain the target imide compound (D-344) as a pale yellow solid (3.92 g, yield 78%). １ H-NMR (DMSO-d6) δ (ppm): 8.79 (dd, J = 4.9, 1.8 Hz, 2H), 8.67 (s, 4H), 8.48 (dd, J = 2.4, 0.9 Hz, 2H), 8.44 (dd, J = 4.9, 1.5 Hz, 2H), 8 .17 (dd, J=7.7, 1.8Hz, 2H), 7.79 (dd, J=7.9, 4.8Hz, 2H), 7.70 (ddd, J=7.8, 2.5, 1.6Hz, 2H), 7.32 (ddd, J=7.8, 4.9, 0.8Hz, 2H).

[0183] (Synthesis Example 29: Synthesis of Imide Compound (D-346)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (2.30 g, 8.58 mmol), 3-phenylpyridine-2-amine (3.21 g, 18.9 mmol), and triethoxyvinylsilane (1.63 g, 8.58 mmol) were suspended in quinoline (57.2 mL) and stirred at 150°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was sequentially washed with ethanol, hexane, toluene, and methanol to obtain the target imide compound (D-346) as a pale yellow solid (4.74 g, yield 97%). １ H-NMR (DMSO-d6) δ (ppm): 8.71-8.74 (m, 2H), 8.66 (d, J = 5.1Hz, 4H), 8.07 (dd d, J = 7.6, 2.7, 1.8 Hz, 2H), 7.74 (dd, J = 7.8, 4.8 Hz, 2H), 7.23-7.31 (m, 10H).

[0184] (Synthesis Example 30: Synthesis of imide compound (D-349)) Under an argon atmosphere, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.25 g, 4.66 mmol), 2-(1-pyrenyl)benzeneamine (3.01 g, 10.3 mmol), and 1,4-diazabicyclo[2.2.2]octane (523 mg, 4.66 mmol) were suspended in N,N-dimethylformamide (46.5 mL) and stirred at 140°C for 8 hours. After cooling to room temperature, the precipitate (crude product) was filtered off. The obtained crude product was washed with ethanol and then purified by recrystallization with toluene to obtain the target imide compound (D-349) as a pale red solid (1.69 g, yield 44%). １ H-NMR (DMSO-d6) δ (ppm): 8.55 (s, 1H), 8.32 (d, J = 7.7Hz, 1H), 8.16-8.23 (m, 5H), 7.96-8.08 (m, 10H), 7.93 (s, 1 H), 7.84 (d, J=9.1Hz, 1H), 7.81 (d, J=9.1Hz, 1H), 7.74 (d, J=7.8Hz, 1H), 7.68-7.72 (m, 5H), 7.57-7.62 (m, 4H).

[0185] (Synthesis Example 31: Synthesis of imide compound (D-288)) Under an argon atmosphere, 5-(1,3,6,8-tetrahydro-1,3,6,8-tetraoxo-7H-isocumeno[6,5,4-def]isoquinoline-7-yl)-1,3-benzodicarbonitric acid (2.36 g, 6.00 mmol), 3-amino-4-(4-pyridinyl)benzonitrile (1.29 g, 6.60 mmol), and benzoic acid (1.10 g, 9.00 mmol) were suspended in nitrobenzene (40 mL) and stirred at 120°C for 14 hours. After cooling to room temperature, the precipitated solid was collected by filtration and washed with ethanol and ether. The collected solid was suspended in saturated sodium bicarbonate aqueous solution (100 mL) and water (100 mL) and stirred at room temperature for 1 hour. The solid was recovered by filtration and washed with water, ethanol, and ether to obtain the target imide compound (D-288) as a pale yellow solid (yield 1.76 g, yield 34%). １H-NMR (DMSO-d6) δ (ppm): 8.73 (brs, 4H), 8.67 (t, J = 1.5Hz, 1H), 8.47 (AA'BB'system, pseudo-dd, 2H), 8.35 (brs, 2H ), 8.25 (d, J=1.7Hz, 1H), 8.20 (dd, J=8.0, 1.7Hz, 1H), 7.86 (d, J=8.0Hz, 1H), 7.25 (AA'BB'system, pseudo-dd, 2H).

[0186] (Synthesis Example 32: Synthesis of Imide Compound (D-282)) Under an argon atmosphere, 5-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isocumeno[6,5,4-def]isoquinoline-7-yl)-1,3-benzodicarbonitric acid (100 mg, 0.25 mmol), 6-amino-[1,1'-biphenyl]-3,4'-dicarbonitric acid (67 mg, 0.31 mmol), and 1,4-diazabicyclo[2.2.2]octane (14 mg, 0.13 mmol) were suspended in N,N-dimethylformamide (3 mL) and stirred at 120°C for 16 hours. After cooling to room temperature, the low-boiling components were removed by distillation, and the resulting solid was purified by recrystallization (N,N-dimethylformamide / ethanol / hexane) to obtain the target imide compound (D-282) as a pale yellow solid (yield 112 mg, yield 74%). １ H-NMR (DMSO-d6) δ (ppm): 8.73-8.68 (m, 4H), 8.67 (t, J = 1.6Hz, 1H), 8.35 (brs, 2H), 8.19 (dd, J = 8.3, 1 9Hz, 1H), 8.15 (d, J = 1.9Hz, 1H), 7.93 (d, J = 8.3Hz, 1H), 7.75 (d, J = 8.4Hz, 2H), 7.44 (d, J = 8.4Hz, 2H).

[0187] (Synthesis Example 33: Synthesis of Imide Compound (D-350)) Under an argon atmosphere, 5-(1,3,6,8-tetrahydro-1,3,6,8-tetraoxo-7H-isocumeno[6,5,4-def]isoquinoline-7-yl)-1,3-benzodicarbonitric acid (98.3 mg, 0.250 mmol) and 4-amino-3-(4-cyanophenyl)pyridine (63.5 mg, 0.325 mmol) were suspended in pyridine (2 mL) and stirred at 120°C for 13 hours. After cooling to room temperature, ethanol was added, and the precipitated solid was collected by filtration and washed with ethanol and ether to obtain the target imide compound (D-350) as a colorless solid (yield 108 mg, yield 76%). １ H-NMR (DMSO-d6) δ (ppm): 8.92 (d, J = 5.2 Hz, 1H), 8.86 (d, J = 0.7 Hz, 1H), 8.80-8.69 (m, 4H), 8. 67 (t, J=1.5Hz, 1H), 8.36 (brs, 2H), 7.81-7.75 (m, 3H), 7.48 (AA'BB'system, pseudo-dd, 2H).

[0188] (Synthesis Example 34: Synthesis of Imide Compound (D-351)) Under an argon atmosphere, 5-(1,3,6,8-tetrahydro-1,3,6,8-tetraoxo-7H-isocumeno[6,5,4-def]isoquinoline-7-yl)-1,3-benzodicarbonitric acid (98.3 mg, 0.250 mmol) and 4-amino-3-(5-pyrimidyl)pyridine (56.0 mg, 6.60 mmol) were suspended in pyridine (2 mL) and stirred at 120°C for 13 hours. After cooling to room temperature, ethanol was added, and the precipitated solid was collected by filtration and washed with ethanol and ether to obtain the target imide compound (D-351) as a colorless solid (yield 93.0 mg, yield 68%). １ H-NMR (DMSO-d6) δ (ppm): 9.07 (s, 1H), 8.97 (d, J = 5.2Hz, 1H), 8.96 (d, J = 0.7Hz, 1H), 8.74 (s , 2H), 8.73-8.70 (m, 4H), 8.67 (t, J=1.5Hz, 1H), 8.36 (brs, 2H), 7.83 (dd, J=5.2, 0.7Hz, 1H).

[0189] (Synthesis Reference Example - 1: Synthesis of Intermediate Products) 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 stirred at 120°C for 16 hours. After cooling to room temperature, the low-boiling components were removed by distillation, and water was added to the resulting suspension. The precipitated solid was filtered off. The filtered solid was washed with hot chloroform, and the low-boiling components were removed from the resulting filtrate. The obtained solid was suspended in acetic anhydride (10 mL) and heated and stirred at 120°C for 1 hour. After cooling to room temperature, the precipitated solid was filtered to obtain 4-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-7H-isochromeno[6,5,4-def]isoquinoline-7-yl)benzonitrile (yield 1.50 g, yield 16%). １ H-NMR (CDCl3) δ (ppm): 8.91-8.88 (m, 4H), 7.91 (d, J = 8.6 Hz, 2H), 7.49 (d, J = 8.6 Hz, 2H).

[0190] (Synthesis Reference Example - 2: Synthesis of Intermediates) Under an argon atmosphere, 4-amino-3-bromobenzonitrile (10.0 g, 50.8 mmol), 4-cyanophenylboronic acid (8.96 g, 61.0 mmol), and tetrakis(triphenylphosphine)palladium (2.54 g, 2.94 mmol) were suspended in a mixed solvent of 2 M aqueous sodium carbonate (75 mL), toluene (254 mL), and ethanol (114 mL), and stirred at 90°C for 8 hours. After cooling to room temperature, 500 mL of water was added to the reaction mixture, and the precipitate (crude product) was filtered off. The obtained crude product was purified by recrystallization with toluene to obtain the target 2-amino[1,1'-biphenyl]-5,4'-dicarbonitride as a white solid (8.60 g, yield 77%). １H-NMR (DMSO-d6) δ (ppm): 7.93 (d, J = 8.6 Hz, 2H), 7.63 (d, J = 8.6 Hz, 2H), 7.47 (dd, J=8.6, 2.0Hz, 1H), 7.41 (d, J=2.0Hz, 1H), 6.83 (d, J=8.6Hz, 1H), 6.03 (brs, 2H).

[0191] (Synthesis Reference Example - 3: Synthesis of Intermediate Products) Under an argon atmosphere, 2-bromoaniline (3.00 g, 17.4 mmol), 1-pyreneboronic acid (5.58 g, 22.7 mmol), and a dichloromethane complex of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.57 g, 0.70 mmol) were suspended in a mixed solvent of 2 M aqueous sodium carbonate (35 mL) and dioxane (87 mL), and stirred at 80°C for 8 hours. After cooling to room temperature, the low-boiling components were removed by vacuum distillation, and then ethyl acetate and saturated brine were added and stirred. After removing the organic layer of the resulting mixed solution by vacuum distillation, the crude product was purified by silica gel column chromatography using toluene and hexane (mixture ratio 1:1) to obtain the target 2-(1-pyrenyl)benzeneamine as a pale yellow viscous liquid (3.54 g, yield 69%). １ H-NMR (DMSO-d6) δ (ppm): 8.37 (d, J = 8.1 Hz, 1H), 8.32 (brd, J = 7.6 Hz, 1H), 8.28 (brd, J=7.1Hz, 1H), 8.23 ​​(d, J=2.1Hz, 2H), 8.14 (d, J=9.2Hz, 1H), 8.09 (t, J=7.6Hz, 1H), 7 .. 95 (d, J=7.8Hz, 1H), 7.81 (d, J=9.2Hz, 1H), 7.23 (brt, J=7.5Hz, 1H), 7.11 (dd, J=7.4 , 1.5Hz, 1H), 6.91 (dd, J=8.2, 1.0Hz, 1H), 6.77 (dt, J=7.4, 1.2Hz, 1H), 4.58 (s, 2H).

[0192] (Evaluation Example 1: Film Quality Evaluation of Imide Compound (D-10)) A Si substrate (with native oxide film) was introduced into a vacuum deposition chamber, and 1.0 × 10 －４The pressure was reduced to Pa. Then, a 30 nm film of sublimation-purified imide compound (D-10) was deposited on the substrate, and the surface condition of the film was observed using an atomic force microscope (Shimadzu SPM-9600). The arithmetic mean roughness (Ra) measured in the surface roughness test was 0.33 nm.

[0193] (Evaluation Example 2: Film Quality Evaluation of Imide Compound (D-34)) The measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-34) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.37 nm.

[0194] (Evaluation Example 3: Film Quality Evaluation of Imide Compound (D-12)) The measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-12) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.17 nm.

[0195] (Evaluation Example 4: Film Quality Evaluation of Imide Compound (D-22)) The measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-22) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.19 nm.

[0196] (Evaluation Example 5: Film Quality Evaluation of Imide Compound (D-46)) The measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-46) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.39 nm.

[0197] (Evaluation Example 6: Film Quality Evaluation of Imide Compound (D-139)) The measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-139) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.31 nm.

[0198] (Evaluation Example 7: Film Quality Evaluation of Imide Compound (D-152)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-152) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.19 nm. (Evaluation Example 8: Film Quality Evaluation of Imide Compound (D-20)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-20) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.19 nm. (Evaluation Example 9: Film Quality Evaluation of Imide Compound (D-8)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-8) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.26 nm. (Evaluation Example 10: Film Quality Evaluation of Imide Compound (D-353)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-353) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.19 nm. (Evaluation Example 11: Film Quality Evaluation of Imide Compound (D-44)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-44) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.24 nm. (Evaluation Example 12: Film Quality Evaluation of Imide Compound (D-228)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-228) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.39 nm. (Evaluation Example 13: Film Quality Evaluation of Imide Compound (D-343)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-343) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.44 nm. (Evaluation Example 14: Film Quality Evaluation of Imide Compound (D-344)) Measurement was performed in the same manner as in Evaluation Example 1, except that imide compound (D-344) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.30 nm.(Evaluation Example 15: Film Quality Evaluation of Imide Compound (D-346)) The measurement was carried out in the same manner as in Evaluation Example 1, except that imide compound (D-346) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.20 nm.

[0199] (Evaluation Reference Example 1: Film Quality Evaluation of Imide Compound (R-1)) The measurement was carried out in the same manner as in Evaluation Example 1, except that the following imide compound (R-1) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 5.07 nm.In addition, the imide compound (R-1) was purchased from Tokyo Chemical Industry and used after sublimation purification.

[0200] (Evaluation Reference Example 2: Film Quality Evaluation of Imide Compound (R-2)) The measurement was carried out in the same manner as in Evaluation Example 1, except that the following imide compound (R-2) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.52 nm.In addition, the imide compound (R-2) was synthesized according to the method disclosed in International Publication No. WO2008 / 072586 and used after sublimation purification.

[0201] From the above film quality evaluations, it was confirmed that the films formed using the imide compounds (D-10, D-34) in Evaluation Examples 1 and 2 had higher film smoothness than the films formed using the imide compounds (R-1, R-2) in Evaluation Reference Examples 1 and 2.

[0202] (Evaluation Reference Example 3: Film Quality Evaluation of Imide Compound (R-3)) The measurement was carried out in the same manner as in Evaluation Example 1, except that the following imide compound (R-3) was used instead of imide compound (D-10). The arithmetic mean roughness (Ra) in the surface roughness measurement was 10.0 nm.In addition, the imide compound (R-3) was synthesized according to the method described in J. Am. Chem. Soc. 2011, 133, 15256-15259.

[0203] From the above film quality evaluation, it was confirmed that the film formed using the imide compound of the evaluation example had higher film smoothness than the films formed using the imide compounds (R-1, R-2, R-3) of Evaluation Reference Examples 1, 2, and 3.

[0204] <Fabrication and Evaluation of Photovoltaic Devices> [Device Example 1] A photovoltaic device 1 having a stacked structure composed of a substrate / second electrode 16 / electron transport layer 15 / light-receiving layer 14 / hole transport layer 13 / hole transport promoting layer 12 / first electrode 11 was fabricated, and the dark current and external quantum efficiency of the photovoltaic device were evaluated.

[0205] (Preparation of Substrate and Second Electrode 16) As a substrate having the second electrode on its surface, a glass substrate with an indium tin oxide (ITO) transparent electrode (ITO film width: 2 mm, film thickness: 110 nm) patterned in a stripe shape was prepared. Then, this substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet cleaning.

[0206] (Preparation for Vacuum Deposition) On the substrate subjected to the surface treatment after cleaning, vacuum deposition of each layer was performed by the vacuum deposition method to form each layer by stacking. First, the above glass substrate was introduced into the vacuum deposition chamber and evacuated to 7.0×10 －５ Pa. Then, each layer was fabricated according to the film formation conditions of each layer in the following order.

[0207] (Fabrication of Electron Transport Layer 15) The sublimation-purified imide compound, 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine, was formed into a 10-nm film at a rate of 0.03 nm / second to fabricate the electron transport layer 15.

[0208] (Fabrication of Light-Receiving Layer 14) N,N-dimethylquinacridone and fullerene C60 were formed into a 250-nm film at a ratio of 4:1 (mass ratio) to fabricate the photovoltaic conversion layer (light-receiving layer) 14. The film formation rate was 0.13 nm / second.

[0209] (Fabrication of Hole Transport Layer 13) As a hole transport material, (HTL-1) was formed into a 10-nm film at a rate of - 0.10 nm / second to fabricate the hole transport layer 13. Incidentally, (HTL-1) was synthesized by the method described in JP-A-2018-193371.

[0210] (Preparation of hole transport promoting layer 12) An imide compound (D-10) was deposited at a rate of 0.20 nm / second to a thickness of 10 nm to prepare the hole transport promoting layer 12.

[0211] (Fabrication of the first electrode 11) Finally, a metal mask was placed perpendicular to the ITO stripe on the substrate, and the first electrode 11 was deposited. The first electrode was deposited with 80 nm of Au. The deposition rate of Au was 0.1 nm / second.

[0212] Therefore, the area is 4 mm². ２ A photoelectric conversion element 1, as shown in Figure 1, was fabricated. When a voltage of 2.5V (absolute value) was applied to the photoelectric conversion element fabricated as described above, such that electrons were transported to the second electrode 16 side and holes to the first electrode 11 side, the dark current (dark current, mA / cm²) was measured. ２ The dark current and external quantum efficiency were evaluated. Dark current was measured using a Keithley Source Measure Unit 2636B. A solar cell spectroscopic sensitivity analyzer (manufactured by Soma Optical Co., Ltd.) was used to measure the external quantum efficiency. The wavelength of the irradiated light was 560 nm, and the intensity was 1.6 μW / cm². ２ Measurements were performed using the following method: Response time: wavelength 560 nm, intensity 1.6 μW / cm². ２ The light was irradiated, and after stopping the irradiation, the time it took for the current value to return to the level before irradiation was measured.

[0213] The results are shown in Table 1. Note that the dark current and external quantum efficiency are relative values, with the results from Comparative Example 1 (described later) set as the baseline value (100). A lower dark current value indicates better performance, while a higher external quantum efficiency value indicates better performance.

[0214] [Device Example 2] A photoelectric conversion element 1 was fabricated in the same manner as in Device Example 1, except that imide compound (D-34) was used instead of imide compound (D-10) in the fabrication of the hole transport-promoting layer 12. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1. [Device Example 3] A photoelectric conversion element 1 was fabricated in the same manner as in Device Example 1, except that imide compound (D-46) was used instead of imide compound (D-10) in the fabrication of the hole transport-promoting layer 12. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1. [Device Example 4] A photoelectric conversion element 1 was fabricated in the same manner as in Device Example 1, except that imide compound (D-44) was used instead of imide compound (D-10) in the fabrication of the hole transport-promoting layer 12. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1. [Device Example 5] A photoelectric conversion device 1 was fabricated in the same manner as in Device Example 1, except that imide compound (D-152) was used instead of imide compound (D-10) in the fabrication of the hole transport promoting layer 12. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1. [Device Example 6] A photoelectric conversion device 1 was fabricated in the same manner as in Device Example 1, except that imide compound (D-288) was used instead of imide compound (D-10) in the fabrication of the hole transport promoting layer 12. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1.

[0215] [Device Comparative Example 1] A photoelectric conversion element of Device Comparative Example 1 was fabricated in the same manner as Device Example 1, except that an imide compound (R-1) was used instead of an imide compound (D-10) in the fabrication of the hole transport promoting layer 12. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1. [Device Comparative Example 2] A photoelectric conversion element of Device Comparative Example 2 was fabricated in the same manner as in Device Example 1, except that the hole transport promoting layer 12 was not provided. The dark current and external quantum efficiency were measured in the same manner as in Device Example 1. The results are shown in Table 1.

[0216]

[0217] As shown in Table 1, the elements of Examples 1 to 6 using the photoelectric conversion element material for image sensors of the present invention showed suppressed dark current and high external quantum efficiency compared to the elements of Comparative Example 1 and Comparative Example 2. Furthermore, the elements of Examples 1 to 6 using the photoelectric conversion element material for image sensors of the present invention showed improved response speed compared to the elements of Comparative Example 1 and Comparative Example 2.

[0218] The organic electronic element of the present invention, by containing the imide compound represented by formula (1) above, can improve the hole transport capability and, when used in a photoelectric conversion element, can perform photoelectric conversion more efficiently. Furthermore, by containing the imide compound represented by formula (1) above, the organic electronic element of the present invention suppresses dark current, and is expected to reduce noise when used in a photoelectric conversion element such as an image sensor. Moreover, by containing the imide compound represented by formula (1) above, the organic electronic element of the present invention can have high external quantum efficiency and can convert light into electric current without loss, so, for example, when used in a photoelectric conversion element, high sensitivity can be expected.

[0219] 1. Photoelectric conversion element 11. First electrode 12. Hole transport enhancement layer 13. Hole transport layer 14. Light receiving layer 15. Electron transport layer 16. Second electrode 2. Organic EL element 21. First electrode 22. Hole injection layer 23. Hole transport layer 24. Light emitting layer 25. Electron transport layer 26. Second electrode

Claims

1. An organic electronic 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 an imide compound having a structure represented by the following formula (1). (Ar １ , Ar ２ represents an arbitrary organic group. However, at least one of Ar １ or Ar ２ is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group represented by the following formula (Q1) and having Cy １ bonded to the ortho position. Ring A represents a monocyclic or condensed aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be one in which a plurality of aromatic hydrocarbon rings are connected directly or via a linking group, and may be substituted with one or more selected from the group consisting of a cyano group, F, Cl, and Br.) (In formula (Q1), Cy １ represents an organic group having a cyclic structure which may be substituted with R １ . X １ to X ４ each independently represents N, C-H or C-R ２ . R １ and R ２ each independently represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, a nitro group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having a cyclic structure which may have 1 to 30 carbon atoms, and these substituents may be a group in which a plurality are combined.) 2. Ar in equation (1) １ Ar ２ The organic electronic element according to claim 1, wherein the two groups are the same.

3. Ar in equation (1) １ Ar ２ The organic electronic element according to claim 1, wherein the groups are different from each other.

4. In formula (Q1), X １ , X ２ , X ３ , and X ４ The organic electronic element according to claim 1, wherein one or more of the elements are C-CN or N.

5. Ar in equation (1) ２ The group is represented by formula (Q1), and Ar １ However, R １ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １ The organic electronic device according to claim 3, wherein the heteroaromatic group having 3 to 30 carbon atoms may be substituted with, or the alkyl group having 1 to 30 carbon atoms may have a branched or cyclic structure.

6. Cy in equation (Q1) １ However, R １ A C6-C30 aromatic hydrocarbon group, which may be substituted with R １ A heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with R １ The organic electronic device according to claim 1, wherein the alkyl group having 3 to 30 carbon atoms has a cyclic structure that may be substituted with a carbon atom.

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

8. The organic electronic device according to claim 1, wherein the organic layer includes a hole transport layer and a hole transport promoting layer containing an imide compound having the structure represented by formula (1), or includes a layer obtained by mixing a hole transport material and an imide compound having the structure represented by formula (1).

9. The organic electronic element according to claim 7, wherein the hole transport layer and the hole transport promoting layer are arranged adjacent to each other between the first electrode and the second electrode.

10. The organic electronic element according to claim 1, wherein the ring A in formula (1) is represented by any of the following (A-1) to (A-10). (In formulas (A-1) to (A-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in ring A. １ When Z has １ These may be the same or different.

11. The organic electronic element according to any one of claims 1 to 10, wherein the ring A in formula (1) is (A-1) or (A-2).

12. A hole transport-promoting material represented by the following formula (2). (Ar ２１ Ar ２２ represents any organic group. However, Ar ２１ or Ar ２２ At least one of these is represented by the following formula (Q2), and the following Cy is in the ortho position. ２ Ring B is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group to which the two groups are bonded. Ring B represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by linking multiple aromatic hydrocarbon rings directly or via linking groups, and may be substituted with one or more groups selected from the group consisting of cyano groups, F, Cl, and Br. (In formula (Q2), Cy ２ R ２１ This represents an organic group having a cyclic structure that may be substituted with X. ２１ ~X ２４ These are, independently, N, C-H, or C-R ２１ Represents R ２１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ This represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 30 carbon atoms, which may have a cyclic structure, and may also be a group formed by a combination of multiple substituents.

13. Ar in equation (2) ２１ Ar ２２ The hole transport promoting material according to claim 12, wherein the two groups are the same.

14. Ar in equation (2) ２１ Ar ２２ The hole transport promoting material according to claim 12, wherein the groups are different from each other.

15. In formula (Q2), X ２１ , X ２２ , X ２３ , and X ２４ The hole transport promoting material according to claim 12, wherein one of the components is C-CN or N.

16. Ar in equation (2) ２２ The base is represented by formula (Q2), and Ar ２１ However, R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ The hole transport promoting material according to claim 14, which is a heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure.

17. Cy in equation (2) ２ However, R ２１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ２１ A heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with R ２１ The hole transport promoting material according to claim 12, which is an alkyl group having 3 to 30 carbon atoms having a cyclic structure that may be substituted with a carbon atom.

18. The hole transport promoting material according to claim 12, wherein the ring B in formula (2) is represented by any of the following (B-1) to (B-10). (In formulas (B-1) to (B-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in ring B. １ When Z has １ These may be the same or different.

19. The hole transport promoting material according to any one of claims 12 to 18, wherein the ring B in formula (2) is (B-1) or (B-2).

20. An imide compound represented by the following formula (3). (Ar ３１ and Ar ３２ R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ This represents a heteroaromatic group having 3 to 30 carbon atoms that may be substituted with, or an alkyl group having 1 to 30 carbon atoms that may have a branched or cyclic structure. However, Ar ３１ or Ar ３２ At least one of these is represented by the following formula (Q3), and the following Cy is in the ortho position. ３ The compound is a six-membered aromatic hydrocarbon group or a six-membered heteroaromatic group bonded to a ring. Ring C represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be formed by the direct linkage of multiple aromatic hydrocarbon rings or via linking groups, and may be substituted with one or more elements selected from the group consisting of cyano groups, F, Cl, and Br. (In equation (Q3), Cy ３ R ３１ This represents an organic group having a cyclic structure that may be substituted with X. ３１ ~X ３４ These are, independently, N, C-H, or C-R ３１ Represents R ３１ These are aromatic hydrocarbon groups with 6 to 30 carbon atoms, heteroaromatic groups with 3 to 30 carbon atoms, cyano groups, nitro groups, F, Cl, Br, CF ３ This represents a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 3 to 30 carbon atoms with a cyclic structure, and may also be a group formed by a combination of multiple substituents.

21. Ar in equation (3) ３１ Ar ３２ The imide compound according to claim 20, wherein the groups are the same.

22. Ar in equation (3) ３１ Ar ３２ The imide compound according to claim 20, wherein the groups are different from each other.

23. In equation (Q3), X ３１ , X ３２ , X ３３ , and X ３４ The imide compound according to claim 20, wherein one of the components is C-CN or N.

24. Ar in equation (3) ３２ The base is represented by formula (Q3), and Ar ３１ However, aromatic hydrocarbon groups (cyano groups, CF) with 6 to 30 carbon atoms ３ (may be substituted with F), heteroaromatic groups (cyano groups, CF) having 3 to 30 carbon atoms. ３ The imide compound according to claim 22, wherein the group is a combination of the following: (which may be substituted with F), or a combination thereof.

25. Ar in formula (3) ３１ is a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazolyl group, a quinolyl group, or an isoquinolyl group, and these groups may be substituted with one or more groups selected from the group consisting of a cyano group, a cyanophenyl group, a dicyanophenyl group, a cyanopyridyl group, a dicyanopyridyl group, a fluoro group, and a trifluoromethyl group, the imide compound according to claim 24.

26. Cy in equation (3) ３ However, R ３１ A C6-C30 aromatic hydrocarbon group, which may be substituted with R ３１ A heteroaromatic group having 3 to 30 carbon atoms, which may be substituted with R ３１ The imide compound according to claim 20, which is an alkyl group having 3 to 30 carbon atoms having a cyclic structure that may be substituted with a carbon atom.

27. Cy in equation (3) ３ The imide compound according to claim 26, wherein the group is a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a triazyl group, a quinolyl group, or an isoquinolyl group, and these groups may be substituted with one or more of the following: a cyano group, a cyanophenyl group, a dicyanophenyl group, a cyanopyridyl group, a dicyanopyridyl group, a fluoro group, or a trifluoromethyl group.

28. R in formula (3) ３１ is a cyano group, CF ３ , F, phenyl group, pyridyl group, pyrimidyl group, pyrazyl group, triazyl group, or a group formed by combining these, the imide compound according to claim 20.

29. The imide compound according to any one of claims 20 to 28, wherein the ring C in formula (3) is represented by any of the following (C-1) to (C-10). (In formulas (C-1) to (C-10), Z １ represents a cyano group, F, Cl, or Br. m represents 0, 1, or 2, and n represents 0, 1, or 2, where 0 ≤ m + n ≤ 4. There are 2 or more Z in the ring C. １ When Z has １ These may be the same or different.

30. The imide compound according to claim 29, wherein the ring C in formula (3) is (C-1) or (C-2).

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