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

Abstract

The present invention provides: an organic electronic element with improved hole transport capability and having good adhesion between layers constituting an organic layer; and an imide compound effective for the formation of the organic electronic element.　The organic electronic element comprises a first electrode, a second electrode, and an organic layer that is disposed between the first electrode and the second electrode, wherein the organic layer contains a compound that has a structure represented by formula (1). (In formula (1), each Ar1 represents a bicyclic, tricyclic or tetracyclic fused-ring heteroaromatic group which is formed only of 6-membered rings and may have one or more substituents R1, or a bicyclic, tricyclic or tetracyclic fused-ring aromatic hydrocarbon group which may have one or more substituents R1, and the two Ar1 are the same.　Ring A represents a monocyclic or fused-ring 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.　R1 represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF3, a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined.)

Description

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

[0001] The present invention relates to an organic electronic device, a hole transport promoting material, and an imide compound.

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

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

[0004] JP 2019-182789 A

[0005] There is a constant demand for an organic electronic element capable of improving hole transport capability. Furthermore, from the viewpoints of practicality and functionality, it is desirable for each organic layer constituting the organic electronic element to have excellent adhesion. Therefore, the present invention provides an organic electronic element capable of improving hole transport capability, in which each layer constituting the organic layer has good adhesion, and an imide compound effective for forming the organic electronic element.

[0006] As a result of extensive research aimed at solving the above problems, the present inventors have found that a specific compound having an imide skeleton as a partial structure can improve the hole transport ability in organic electronic devices such as photoelectric conversion devices and organic EL devices, and can form a layer that has excellent adhesion to adjacent layers, thereby completing the present invention.

[0007] That is, the present invention includes the following aspects: [1] An organic electronic device including a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a structure represented by the following formula (1): (In formula (1), Ar １ is a substituent R １ a fused heteroaromatic group having two, three or four rings formed solely of six-membered rings, which may have one or more substituents R １ represents a fused aromatic hydrocarbon group having two, three or four rings, which may have one or more Ar １ are the same. 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 together directly or via a linking group. R １ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group formed by combining these substituents.) [2] The organic electronic device according to [1], further comprising a light-receiving layer disposed between the first electrode and the second electrode. [3] The organic electronic device according to [1] or [2], wherein the organic layer comprises a hole transport layer and a hole transport promoting layer containing a compound having a structure represented by formula (1), or contains a layer formed by mixing a hole transport material with a compound having a structure represented by formula (1). [4] The organic electronic device according to [3], wherein the hole transport layer and the hole transport promoting layer are disposed adjacent to each other between the first electrode and the second electrode. [5] The organic electronic device according to any one of [1] to [4], wherein the ring A in formula (1) is represented by any one of the following (A-1) to (A-10): [6] The organic electronic device according to [5], wherein in the formula (1), the ring A is (A-1) or (A-2). [7] In the formula (1), the Ar １ is a substituent R １[8] The organic electronic device according to any one of [1] to [6], wherein Ar is a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, a benzofluorenyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, an acridyl group, a naphthyridyl group, a quinoxalyl group, a pyridopyrazyl group, a pteridyl group, a pyrazinopyrazyl group, a pyrimidopyrimidyl group, a benzoquinolyl group, a benzoisoquinolyl group, an acridyl group, a benzoquinazolyl group, a phenanthridyl group, or a phenanthrolyl group, each of which may have one or more of the following: １ has a partial structure represented by the following formula (B): (In formula (B), X １ ~X ７ are N, C—H or C—R, respectively. １１ Represents R １１ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. １１ may be bonded to each other to form a cyclic structure, and two R １１ When two R １１ [9] In the formula (1), R １ is a cyano group, a methyl group, a fluoro group, or CF ３

[10] The organic electronic device according to any one of [1] to [8], wherein the aryl group is a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a quinolyl group, an isoquinolyl group, or a combination of these groups. (In formula (1), Ar １ is a substituent R １a fused heteroaromatic group having two, three or four rings formed solely of six-membered rings, which may have one or more substituents R １ represents a fused aromatic hydrocarbon group having two, three or four rings, which may have one or more Ar １ are the same. 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 together directly or via a linking group. R １ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group formed by combining these substituents.)

[11] The hole transport promoting material according to

[10] , wherein the ring A in the formula (1) is represented by any one of the following (A-1) to (A-10):

[12] The hole transport promoting material according to

[10] or

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

[13] In the formula (1), １ is a substituent R １

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

[10] to

[12] , wherein Ar is a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, a benzofluorenyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, an acridyl group, a naphthyridyl group, a quinoxalyl group, a pyridopyrazyl group, a pteridyl group, a pyrazinopyrazyl group, a pyrimidopyrimidyl group, a benzoquinolyl group, a benzoisoquinolyl group, an acridyl group, a benzoquinazolyl group, a phenanthridyl group, or a phenanthrolyl group, wherein Ar １ The hole transport promoting material according to any one of

[10] to

[13] , wherein the hole transport promoting material has a partial structure represented by the following formula (B): (In formula (B), X １ ~X ７ are N, C—H or C—R, respectively. １１ Represents R １１represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. １１ may be bonded to each other to form a cyclic structure, and two R １１ When two R １１ respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, or an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.)

[15] In the formula (1), R １ is a cyano group, a methyl group, a fluoro group, or CF ３

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

[10] to

[14] , wherein the imide compound is an imide compound represented by the following formula (2): (In formula (2), Y １ ~Y ７ is N, C—H or C—R ２ where Y １ ~Y ７ If there is one or more Ns, then Y １ , Y ２ , and Y ３ Any one of the following is N, and Y １ ~Y ７ If N is 0, then Y １ ~Y ７ At least one of them is C-R ２ Ring C represents a monocyclic or condensed aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be a ring in which a plurality of aromatic hydrocarbon rings are linked together directly or via a linking group. ２ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３, a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. ２ may be bonded to each other to form a cyclic structure, and two R ２ When two R ２ respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, or an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.)

[17] The imide compound according to

[16] , wherein the ring C in the formula (2) is represented by any one of the following (C-1) to (C-10):

[18] The imide compound according to

[17] , wherein in the formula (2), the ring C is (C-1) or (C-2). ３ is N or C-R ２

[16] The imide compound according to any one of

[16] to

[18] ,

[0008] According to the present invention, it is possible to provide an organic electronic element that can improve the hole transport capability and has good adhesion between the layers that constitute the organic layer, and an imide compound that is effective for forming the organic electronic element.

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

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

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

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

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

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

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

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

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

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

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

[0020] The organic EL device according to the present invention may have, for example, a first electrode, a hole injection layer, a hole transport layer, and a second electrode laminated in this order, or a first electrode, a layer formed by mixing a hole transport material forming the hole transport layer with the compound represented by formula (1), and a second electrode laminated in this order. The organic EL device may also have, for example, the first electrode, the hole injection layer, and the hole transport layer laminated adjacently in this order, or another layer such as a buffer layer may be interposed between the first electrode and the hole injection layer or between the hole injection layer and the hole transport layer.

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

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

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

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

[0025]

[0026] In formula (1), Ar １ is a substituent R １ a fused heteroaromatic group having two, three or four rings formed solely of six-membered rings, which may have one or more substituents R １ represents a fused aromatic hydrocarbon group having two, three or four rings, which may have one or more Ar １ are the same. 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 together directly or via a linking group. R １ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may also be a group in which these substituents are combined.

[0027] The R １In the above formula, examples of the aromatic hydrocarbon group having 6 to 30 carbon atoms include a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a tetracenyl group, a chrysenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a biphenylyl group, a terphenyl group, a naphthylphenyl group, a phenylnaphthyl group, a binaphthyl group, an anthrylphenyl group, a phenylanthryl group, a naphthylanthryl group, etc. In view of excellent device performance, a phenyl group or a naphthyl group is preferred.

[0028] The R １ In the above, examples of the heteroaromatic group having 3 to 30 carbon atoms include a pyridyl group, a pyrazyl group, a pyrimidyl group, a triazyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, a naphthyridyl group, a quinoxalyl group, a pyridopyrazyl group, a pteridyl group, a pyrazinopyrazyl group, a pyrimidopyrimidyl group, a benzoquinolyl group, a benzoisoquinolyl group, a benzoquinoxalyl group, a phenanthrolyl group, a phenanthridyl group, an acridyl group, a phenanthro ... Examples of the alkyl group include a pyridinyl group, a phenoxazinyl group, a phenothiazinyl group, a hexaazatriphenylenyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, an isobenzofuryl group, a dibenzothiophenyl group, a dibenzofuranyl group, a benzoxazolyl group, a pyrrole group, an indole group, an isoindole group, an indolizinyl group, a purine group, an imidazolyl group, a carbazolyl group, a thiazolyl group, a thiadiazolyl group, etc. In terms of excellent device performance, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, and an isoquinolyl group are preferred, and in terms of ease of synthesis, a pyridyl group or a pyrazyl group is more preferred.

[0029] The R １In the formula (I), examples of the perfluoroalkyl group having 2 to 15 carbon atoms include a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a perfluoropentane group, a perfluorohexane group, a perfluoroheptane group, a perfluorooctane group, a perfluorononane group, a perfluorodecane group, a perfluoroundecane group, a perfluorododecane group, a tridecane group, a perfluorotetradecane group, and a perfluoropentadecane group, and these may be branched or cyclic perfluoroalkyl groups.

[0030] Examples of the alkyl group having 1 to 15 carbon atoms and optionally having a cyclic structure include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a tert-butyl group, an isopropyl group, etc. In terms of ease of synthesis, an adamantyl group, a methyl group, or an ethyl group is preferred, and in terms of excellent device performance, a methyl group is more preferred.

[0031] Above R １ may be a group in which a plurality of groups of each specific example are combined, or may be a group in which a plurality of the same groups are combined. １ is preferably a cyano group, a fluoro group, a trifluoromethyl group, a pyridyl group, a phenyl group, a quinolyl group, a naphthyl group, or a combination thereof. For example, a cyano group, a fluoro group, a trifluoromethyl group, a phenyl group, a naphthyl group, a cyanophenyl group, a dicyanophenyl group, a cyanopyridyl group, or a dicyanopyridyl group is preferred. In terms of ease of synthesis, a cyano group is more preferred.

[0032] R １ As an example of a combination of multiple groups, for example, an imide compound represented by (D-78) described later, １ Examples of the cyano group include a combination of two groups, a cyano group and a cyanophenyl group.

[0033] Ring A represents a monocyclic or fused aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be one in which a plurality of aromatic hydrocarbon rings are linked together directly or via a linking group. Preferred examples of ring A include the following (A-1) to (A-10). Among these, (A-1) or (A-2) are more preferred in terms of excellent hole transport promoting performance.

[0034]

[0035] Ar １ is a substituent R １ a fused heteroaromatic group having two, three or four rings formed solely of six-membered rings, which may have one or more substituents R １ represents a fused aromatic hydrocarbon group having two, three or four rings, which may have one or more Ar １ are the same. １ In the above, the 2, 3 or 4-ring fused heteroaromatic group formed only by the 6-membered ring can be exemplified by quinolyl group, isoquinolyl group, quinazolyl group, acridyl group, naphthyridyl group, quinoxalyl group, pyridopyrazyl group, pteridyl group, pyrazinopyrazyl group, pyrimidopyrimidyl group, benzoquinolyl group, benzoisoquinolyl group, acridyl group, benzoquinazolyl group, phenanthridyl group, phenanthrolyl group, etc. Among these, quinolyl group, isoquinolyl group, phenanthrolyl group are preferred, and quinolyl group is more preferred in terms of excellent hole transport promoting performance.In addition, when forming a film by vacuum deposition, it is necessary to lower the molecular weight to a certain extent, and in this case, 2- or 3-ring fused heteroaromatic group is preferred, and 2-ring fused heteroaromatic group is more preferred in terms of easy synthesis.

[0036] The Ar １In the formula (I), examples of the fused aromatic hydrocarbon group having two, three or four rings include a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, and a benzofluorenyl group. Among these, a naphthyl group and a phenanthryl group are preferred, and a naphthyl group is more preferred in terms of excellent hole transport promoting performance. Furthermore, when forming a film by vacuum deposition, a certain degree of molecular weight reduction is required, and in this case, a fused aromatic hydrocarbon group having two or three rings is preferred, and a fused aromatic hydrocarbon group having two rings is more preferred in terms of ease of synthesis.

[0037] In addition, the Ar １ Specific examples of the substituent R １ Ar may have one or more of １ Substituent R substituted with １ As described above, is preferably a cyano group, a fluoro group, a trifluoromethyl group, a pyridyl group, a phenyl group, a quinolyl group, a naphthyl group, or a combination thereof, and is more preferably a cyano group in terms of excellent hole transport promoting performance.

[0038] The Ar １ Examples of the group include a group having a partial structure represented by the following formula (B).

[0039] In formula (B), X １ ~X ７ are N, C—H or C—R, respectively. １１ Represents R １１ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. １１ may be bonded to each other to form a cyclic structure, and two R １１ When two R １１respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, and an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.

[0040] Ar １ has a partial structure represented by the above formula (B), and two adjacent R １１ are bonded to each other to form a cyclic structure, and thus may contain a fused ring of three rings, such as a phenanthryl group represented by (E-110) or a phenanthrolyl group represented by (E-118) described later. １ may also include a fused ring of four rings as long as it has a partial structure represented by the above formula (B). １１ The cyclic structure formed by bonding together may be an aromatic ring as shown in (E-110) above, or a heteroaromatic ring as shown in (E-118) above.

[0041] Ar １ Preferred examples of the above include the following (E-1) to (E-171).

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051] The imide compound represented by formula (1) is preferably an imide compound represented by the following formula (1B):

[0052]

[0053] In formula (1B), A is the same as A in formula (1). １ ~X ７ are X in the formula (B), respectively. １ ~X ７ In the formula (1B), the two X １ ~X ７ In other words, in formula (1B), X on the left ３ For example, if it is N, then the X on the right ３ is also N.

[0054] In formula (1B), the group represented by formula (B) also includes a group having a resonance structure. For example, the group of the partial structure represented by formula (B) below also includes groups represented by formula (B)' and formula (B)" below. In the present invention, these groups have the same meaning.

[0055]

[0056] The organic electronic element of the present invention is not particularly limited, but examples thereof include an organic EL element and a photoelectric conversion element (such as a solar cell, a photodiode, or a photoelectric conversion element for an imaging element). As the organic electronic element, a photoelectric conversion element is preferred, and a photoelectric conversion element for an imaging element is more preferred.

[0057] The compound represented by formula (1) is used as a part of an organic electronic device. The part of the organic electronic device is not particularly limited, but examples thereof include an electron transport layer, a light-emitting layer, a light-receiving layer, a hole injection layer, and a hole transport promotion layer. Among these, the compound represented by formula (1) is preferably used in the hole transport promotion layer.

[0058] Preferred examples of the imide compound represented by formula (1) include the following (D-1) to (D-130), although the compound of the present invention is not limited to these.

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] [Manufacturing Method] The compound represented by the above formula (1) or the formula (2) described below can be synthesized by a known method or a combination thereof (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.). For example, the compound represented by formula (1) can be synthesized by the synthetic route shown below.

[0071] (In the formula, Ar １ , ring A is Ar in the formula (1) １The reaction may be carried out in a reaction solvent, and preferred examples of the reaction solvent include haloalkanes such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, and tetrachloroethane; ethers such as diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; heteroaromatic compounds such as imidazole, pyridine, pyrazine, and quinoline; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; and acetic acid. Examples of suitable solvents include esters such as ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); sulfoxides such as dimethyl sulfoxide (DMSO); alcohols such as methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol; and phenols such as phenol, naphthol, and cresol. These solvents may be used alone or in any combination, and there are no particular limitations on the amount of solvent used. Among these, cresol, DMF, DMAc, pyridine, xylene, and mixed solvents thereof are preferred in terms of their good reaction yield. This reaction can be accelerated by carrying out the reaction in the presence of a conventionally known condensing agent.Examples of the condensing agent include solid acids such as alumina and silica gel; metal chlorides such as titanium tetrachloride, tin tetrachloride, and antimony pentachloride; organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, diazabicycloundecene, tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane; and carbodiimides such as 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, and 1,1'-carbonyldi(1,2,4-triazole). The amount of the condensing agent used is preferably 0.1 to 10 moles, more preferably 0.5 to 5 moles, per mole of compound (1a) represented by the above formula. The amount of the amine compound represented by the above formula used is preferably 1.0 to 1.2 moles per mole of compound (1a) in terms of reaction yield and production efficiency. The reaction temperature and reaction time vary depending on the amounts 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 allows the reaction to proceed sufficiently, and a reaction temperature of 180°C or lower is economically preferred, and the reaction time is preferably in the range of 1 to 24 hours.

[0072] <<Action and Effect of the Compound Represented by Formula (1)>> The compound represented by formula (1) has a naphthalenetetracarboxylic acid diimide skeleton or a specific skeleton structure similar thereto, and therefore this strong acceptor skeleton is expected to have a strong interaction with the HOMO orbital of the hole transport material. In other words, when a layer (e.g., a hole transport promotion layer) in an organic electronic device (e.g., a photoelectric conversion device) contains a compound represented by formula (1), it is expected that the interaction with the HOMO orbital of an adjacent hole transport layer will be enhanced, and carrier exchange between the hole transport layer and the hole transport promotion layer will be promoted. In this way, the compound represented by formula (1) has an extremely deep LUMO level, and therefore it is expected that the exchange of holes between the hole transport layer and the electrode will be smooth. Furthermore, since the compound represented by formula (1) has a naphthalenetetracarboxylic acid diimide skeleton or a specific skeleton structure similar thereto, thermal stability, high reduction resistance, etc. can also be expected. In addition, the compound represented by formula (1) has improved amorphous properties due to the effects of the bulky quinolyl group, etc., and therefore can form a flat film and improve adhesion to adjacent layers.

[0073] As described above, the present inventors have found that the compound represented by formula (1) can be effectively used as a hole transport promoting material that facilitates the exchange of holes between a hole transport layer and an electrode. They have confirmed that, in a photoelectric conversion element, the hole transport ability is promoted when the compound represented by formula (1) (hole transport promoting material) is combined with a hole transport material. That is, they have confirmed that, in a photoelectric conversion element, the energy barrier when carriers generated in the light-receiving layer are extracted to the electrode side can be reduced by the compound represented by formula (1), which is the hole transport promoting material of the present invention.

[0074] <<Hole Transport Promoting Material>> As described above, the compound represented by formula (1) is preferably used as a hole transport promoting material in the hole transport promoting layer.

[0075] <Embodiments> Examples of the laminate structure of the organic electronic element (e.g., photoelectric conversion element) of the present invention include the following structures (i) and (ii): (i): first electrode / hole transport promoting layer / hole transport layer / light-receiving layer / second electrode (ii): first electrode / hole transport promoting layer / hole transport layer / light-receiving layer / electron transport layer / second electrode When the organic electronic element is, for example, an organic EL element, the "light-receiving layer" in the structure (i) or (ii) can be read as the "light-emitting layer".

[0076] The photoelectric conversion element and organic EL element according to the present invention will be described in more detail below, taking the above-mentioned configuration (ii) as an example, with reference to Fig. 1 and Fig. 2. Fig. 1 is a schematic cross-sectional view showing an example of the layered configuration of the photoelectric conversion element according to the present invention, and Fig. 2 is a schematic cross-sectional view showing an example of the organic EL element according to the present invention.

[0077] <<First Embodiment>> A photoelectric conversion element according to a first embodiment is an organic imaging element or photosensor having the layered structure shown in Fig. 1. The photoelectric conversion element 1 includes a first electrode 11 (first electrode), a hole transport promotion layer 12, a hole transport layer 13, a light-receiving layer 14, an electron transport layer 15, and a second electrode 16 (second electrode), in this order. However, some of these layers may be omitted, or other layers may be added.

[0078] In the photoelectric conversion element 1 shown in FIG. 1 , light is incident from above the transparent first electrode 11 and is received by the light-receiving layer 14. For convenience, FIG. 1 illustrates light as being incident from the side of the light-receiving layer 14. Furthermore, a voltage is applied to the photoelectric conversion element 1 so that, of the charges (holes and electrons) generated by photoelectric conversion in the light-receiving layer 14, the holes are moved to the first electrode 11 and the electrons are moved to the second electrode 16. That is, the first electrode 11 serves as a hole-collecting electrode, and the second electrode 16 serves as an electron-collecting electrode. Note that the substrate provided above the first electrode or below the second electrode 16 is omitted from FIG. 1 . The substrate here is not particularly limited, and examples include a glass plate, a quartz plate, and a plastic plate. Furthermore, in a configuration in which light is incident from the substrate side, the substrate is transparent to the wavelength of light. Each of the above layers will be described below.

[0079] [First electrode 11] A first electrode 11 or a second electrode 16 is provided on a substrate. In the case of a photoelectric conversion element configured so that light passes through the first electrode 11 and enters the light-receiving layer 14, the first electrode is formed of a transparent material that transmits or substantially transmits the light. Here, "transmits light" means that the average transmittance is 80% or more, and "substantially transmits light" means that the average transmittance is 50% or more. In other words, in this specification, "transparent" means that the average transmittance is 50% or more.

[0080] The transparent material used for the first electrode 11 or the second electrode 16 is not particularly limited, but examples thereof include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide, aluminum-doped tin oxide, magnesium-indium oxide, nickel-tungsten oxide, other metal oxides, metal nitrides such as gallium nitride, metal selenides such as zinc selenide, and metal sulfides such as zinc sulfide.

[0081] In the case of a photoelectric conversion element configured so that light enters the light-receiving layer 14 only from the second electrode 16 side, the transmittance characteristics of the first electrode 11 are not important. Therefore, examples of materials that can be used for the first electrode in this case include gold, iridium, molybdenum, palladium, and platinum.

[0082] [Hole Transport Promotion Layer 12] The hole transport promotion layer 12 is provided between the first electrode 11 and the hole transport layer 13 described below. The hole transport promotion layer 12 is provided to promote hole transport from the hole transport layer 13 to the first electrode 11. The hole transport promotion layer 12 contains the compound represented by formula (1) above. The hole transport promotion layer 12 may also contain a compound other than the compound represented by formula (1). Examples of compounds that can be contained in the hole transport promotion layer 12 include conventionally known hole transport materials, such as the compounds used in the hole transport layer 13 described below.

[0083] [Hole Transport Layer 13] The hole transport layer 13 is provided between the hole transport promotion layer 12 and the light-receiving layer 14. The hole transport layer 13 has a role of transporting holes generated in the light-receiving layer 14 from the light-receiving layer 14 to the first electrode 11, and a role of blocking electrons generated in the light-receiving layer 14 from moving toward the first electrode 11. Depending on the application, the hole transport layer 13 may also have a role of blocking electron injection from the first electrode 11.

[0084] The hole transport layer 13 may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions. The hole transport material that can be contained in the hole transport layer 13 may be a known hole transport material. Examples of known hole transport materials include aromatic tertiary amine compounds, naphthalene compounds, anthracene compounds, tetracene compounds, pentacene compounds, phenanthrene compounds, pyrene compounds, perylene compounds, fluorene compounds, carbazole compounds, indole compounds, pyrrole compounds, picene compounds, thiophene compounds, benzotrifuran compounds, benzotrithiophene compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzodithiophene compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds. Among these, fluorene compounds, carbazole compounds, naphthodithiophene compounds, naphthothienothiophene compounds, benzodifuran compounds, benzothiophene compounds, naphthobisbenzothiophene compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, indolocarbazole compounds, etc. are preferred, and fluorene compounds, carbazole compounds, chrysenodithiophene compounds, benzothienobenzothiophene compounds, and indolocarbazole compounds are particularly preferred.

[0085] [Light-receiving layer 14] The light-receiving layer 14 is provided between the hole-transporting layer 13 and the electron-transporting layer 15 described below. Examples of materials for the light-receiving layer 14 include materials having a photoelectric conversion function.

[0086] The absorption layer 14 may have a single layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions. In particular, in order to increase the photoelectric conversion efficiency, the absorption layer is preferably made of a layer containing at least two materials (organic components).

[0087] Examples of materials used for the light-receiving layer 14, which has a single-layer structure made of one material, include (i) coumarin and its derivatives, quinacridone and its derivatives, and phthalocyanine and its derivatives. Examples of materials used for the light-receiving layer 14, which has a single-layer structure made of two materials, include the aforementioned combinations of (i) coumarin and its derivatives, quinacridone and its derivatives, and phthalocyanine and its derivatives with (ii) fullerene and its derivatives and other acceptor materials. The light-receiving layer 4 made of these materials may be formed by vapor deposition of a premixed powder, or by co-evaporation in any ratio. Examples of materials used for the light-receiving layer 14, which has a single-layer structure made of three materials, include the aforementioned combinations of (i) coumarin and its derivatives, quinacridone and its derivatives, and phthalocyanine and its derivatives with (ii) fullerene and its derivatives and other acceptor materials, and (iii) hole-transport materials. The light-receiving layer 14 made of these materials may be formed by depositing a mixture of powders in advance, or by co-depositing the materials in any ratio.

[0088] (i) Specific examples of coumarin derivatives include coumarin 6 and coumarin 30. Specific examples of quinacridone derivatives include N,N-dimethylquinacridone. Specific examples of phthalocyanine derivatives include boron subphthalocyanine chloride and boron subnaphthalocyanine chloride (SubNC). (ii) Specific examples of fullerenes and their derivatives include

[60] fullerene,

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

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

[0089] Furthermore, the material having a photoelectric conversion function is not limited to being contained only in the light-receiving layer 14. For example, the material having a photoelectric conversion function may be contained in a layer adjacent to the light-receiving layer 14 (hole transport layer 13 or electron transport layer 15).

[0090] [Electron Transport Layer 15] The electron transport layer 15 is provided between the light-receiving layer 14 and the second electrode 16 described below. The electron transport layer 15 has a role of transporting electrons generated in the light-receiving layer 14 to the second electrode 16 and a role of blocking the movement of holes from the second electrode 16, to which the electrons have been transported, to the light-receiving layer 14. Depending on the application, the electron transport layer 15 may also have a role of blocking hole injection from the second electrode 16.

[0091] The electron transport material that can be contained in the electron transport layer 15 may be a known electron transport material. Examples of the electron transport material include fullerene, fullerene derivatives, triazine derivatives, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), and Bp hen(4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum), 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine, N,N'-diphenyl-1,4,5,8-naphthalenetetracarboxylic acid diimide, and N,N'-di(4-pyridyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide.

[0092] The electron transport layer 15 may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions.

[0093] [Second Electrode 16] A second electrode 16 is provided on the electron transport layer 15. Examples of materials for the second electrode 16 include indium-tin oxide (ITO), indium-zinc oxide (IZO), sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium / copper mixture, a magnesium / silver mixture, a magnesium / aluminum mixture, a magnesium / indium mixture, and aluminum / aluminum oxide (Al ２ O ３ ) mixture, indium, lithium / aluminum mixture, gold, platinum, rare earth metals, molybdenum oxide, etc. The first electrode 11 and the second electrode 16 may be the same or different.

[0094] [Method of Forming Each Layer] Each layer except for the first electrode 11 and the second electrode 16 described above can be formed by thinning the material of each layer (together with a material such as a binder resin and a solvent, if necessary) by a known method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc. There are no particular restrictions on the film thickness of each layer formed in this manner and it can be selected appropriately depending on the situation, but it is usually in the range of 5 nm to 5 μm.

[0095] The first electrode 11 and the second electrode 16 can be formed by thinning an electrode material by a method such as vapor deposition or sputtering. A pattern may be formed through a mask of a desired shape during vapor deposition or sputtering, or a pattern of a desired shape may be formed by photolithography after forming a thin film by vapor deposition or sputtering.

[0096] The film thickness of the first electrode 11 and the second electrode 16 is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0097] The materials constituting the first electrode 11 and the second electrode 16 may be interchanged as necessary (also called an inverted structure). In such a structure, a photoelectric conversion element is formed in which light passes through the second electrode 16 and enters the light-receiving layer 14.

[0098] An imaging element including the photoelectric conversion element of this embodiment can be applied to, for example, an imaging element of a digital camera or a digital video camera, and an imaging element built into a mobile phone, etc. An optical sensor can be applied to, for example, a television remote control, an air conditioner switch, an automatic door opener, etc.

[0099] <<Second Embodiment>> A photoelectric conversion element according to a second embodiment of the present invention is a solar cell having the layered structure shown in Fig. 1. In the solar cell 1, a hole transport promotion layer 12 and a hole transport layer 13 are provided between a first electrode 11 and a light-receiving layer 14, and an electron transport layer 15 is provided between a second electrode 16 and the light-receiving layer 14. However, some of these layers may be omitted, or conversely, other layers may be added.

[0100] [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).

[0101] [Hole Transport Promotion Layer 12] The material of the hole transport promotion layer 12 is the same as the material of the hole transport promotion layer 12 in the first embodiment (the compound represented by formula (1)). The material of the hole transport promotion layer 12 may contain a conventionally known hole transport material in addition to the material in the first embodiment.

[0102] [Hole Transport Layer 13] The material of the hole transport layer 13 is the same as the material of the hole transport layer 13 in the first embodiment. The material of the hole transport layer 13 may contain a conventionally known hole transport material in addition to the hole transport material in the first embodiment.

[0103] [Light-Receiving Layer 14] The light-receiving layer 14 may be made of an electron-donating material and an electron-accepting material. This may be a planar bond type in which the electron-donating material and the electron-accepting material are bonded to each other at their respective planes, or a bulk heterobond type in which the electron-donating material and the electron-accepting material are mixed and formed into a film. The electron-donating material is not particularly limited, but an organic semiconductor is preferred. Examples of electron-donating materials include polymeric compounds and copolymers thereof, such as polythiophene derivatives, polyfluorene derivatives, and polyphenylene vinylene derivatives, as well as low-molecular-weight compounds, such as phthalocyanine derivatives and their metal complexes, porphyrin derivatives and their metal complexes, acene derivatives such as pentacene, and diamine derivatives. The electron-donating material may be an inorganic semiconductor in addition to an organic semiconductor, provided that the effects of the present invention are not impaired. The electron-accepting material is not particularly limited, but an organic semiconductor is preferred. Examples of electron-accepting materials include fullerene derivatives, perylene derivatives, and naphthalene derivatives.

[0104] [Electron Transport Layer 15] The electron transport material in the first embodiment can be used as the material for the electron transport layer 15. Alternatively, the electron transport material may be an alkali metal halide such as sodium fluoride or cesium fluoride, an alkaline earth metal halide such as calcium fluoride, a carbonate such as cesium carbonate, or an inorganic n-type semiconductor such as titanium oxide or zinc oxide.

[0105] [Second Electrode 16] The second electrode 16 may be made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof, but is not limited to these.

[0106] The materials constituting the first electrode 11 and the second electrode 16 may be interchanged as necessary (also called an inverted structure). In such a structure, a photoelectric conversion element is formed in which light passes through the second electrode 16 and enters the light-receiving layer 14.

[0107] [Method of Forming Each Layer] The method of forming each layer is not particularly limited. For example, the first electrode 11, the hole transport promotion layer 12, the hole transport layer 13, the light-receiving layer 14, the electron transport layer 15, and the second electrode 16 may be sequentially laminated on a substrate using a vapor deposition method, a spin coating method, a casting method, a pattern transfer method, or the like. Alternatively, the hole transport promotion layer 12, the hole transport layer 13, the light-receiving layer 14, and the electron transport layer 15 may be laminated, and then the first electrode 11 and the second electrode 16 may be formed on this laminate by transfer, vapor deposition, sputtering, or the like.

[0108] <<Third Embodiment>> An organic electronic element according to a third embodiment of the present invention is an organic EL element having the layered structure shown in Fig. 2. That is, the organic EL element 2 has a first electrode 21, a hole injection layer 22, a hole transport layer 23, a light-emitting layer 24, an electron transport layer 25, and a second electrode 26 provided in this order. However, some of these layers may be omitted, or other layers may be added.

[0109] [First Electrode 21] The first electrode 21 has a role of injecting holes from the hole transport layer to the light emitting layer. As the first electrode 21, a transparent electrode such as indium tin oxide (ITO), indium zinc oxide (IZO), gold, silver, platinum, copper, or the like, a metal or alloy such as aluminum, molybdenum, chromium, nickel, a polythiophene derivative having high charge transportability, a polyaniline derivative, or the like can be used, but is not limited to these.

[0110] The organic electronic element may emit light from either the first electrode 21 or the second electrode 26, or from both the first and second electrodes 21 and 26. The electrode from which light is extracted is made of a transparent material such as ITO or IZO. For convenience, FIG. 2 shows light emitted from the side of the light-emitting layer 24.

[0111] [Hole injection layer 22] The hole injection layer 22 is provided between the first electrode 21 and the hole transport layer 23 described below. The hole injection layer 22 is provided to promote hole transport from the first electrode 21 to the hole transport layer 23. The hole injection layer 22 contains the compound represented by the above formula (1) as a hole injection material. The hole injection layer 22 may also contain compounds other than the compound represented by the above formula (1). Examples of compounds that can be contained in the hole injection layer 22 include conventionally known hole transport materials.

[0112] [Hole Transport Layer 23] The hole transport layer 23 is provided between the hole injection layer 22 and the light-emitting layer 24. The hole transport layer 23 has a role of transporting holes injected from the first electrode 21 to the light-emitting layer 24. The hole transport layer 23 may have a single-layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same composition or different compositions. The hole transport material that can be contained in the hole transport layer 23 may be the same as the material of the hole transport layer 13 in the first embodiment.

[0113] [Light-emitting layer 24] The light-emitting layer 24 has a role of generating light emission (phosphorescence or fluorescence) through recombination of holes injected from the first electrode 21 and electrons injected from the second electrode 26, and contains a light-emitting material and, if necessary, a light-emitting host material. The light-emitting material and the light-emitting host material can be appropriately selected from known materials. Examples of the light-emitting material and the light-emitting host material include carbon-fused ring dyes such as triazine derivatives (including TADF materials substituted with carbazole or the like), pyrimidine derivatives, carbazole derivatives, anthracene derivatives, tetracene derivatives, pyrene derivatives, rubrene derivatives, and decacyclene derivatives; perylene derivatives such as perylene diimide; xanthene dyes such as rhodamine B; cyanine dyes; coumarin dyes such as coumarin 6 and C545T; quinacridone dyes such as Qd4 and DEQ; squarylium dyes; styryl dyes; pyrazolone derivatives; phenoxazone dyes such as NileRed; carbazole; triarylamine; and tris(2-phenylpyridine). Examples of suitable metal complexes include, but are not limited to, iridium complexes such as iridium(III) (Ir(ppy)), tris[2-phenyl-4-(2-ethylcyclohexyloxy)pyridine]iridium(III) (Ir(ehppy)), aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrin zinc complexes, europium complexes, and metal complexes composed of a central metal such as Al, Zn, Be, or a rare earth metal such as Tb, Eu, or Dy, and a ligand such as an oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, or quinoline structure.

[0114] [Electron Transport Layer 25] The electron transport layer 25 is provided between the second electrode and the light-emitting layer, and has the function of transporting electrons injected from the second electrode to the light-emitting layer. Examples of the electron transport material include, but are not limited to, triazine derivatives, tris(8-quinolinolato)aluminum (Alq), bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminum (BAlq), 1,4,4'-bis(2,2'-diphenylvinyl)-1,1'-bipheny (DPVBi), (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole) (PBD), triazole derivatives (TAZ), bathocuproine (BCP), and silole derivatives.

[0115] [Second Electrode 26] The second electrode 26 has a role of injecting electrons from the electron transport layer 25 to the light-emitting layer 24. The second electrode 26 may be made of aluminum, a magnesium-silver alloy, an aluminum-lithium alloy, lithium, sodium, potassium, cesium, cesium-doped ITO, or the like, but is not limited to these.

[0116] [Method of Forming Each Layer] To form each layer of the organic EL element 2, for example, first, a thin film made of the material of the first electrode 21 is formed on a suitable light-transmitting substrate (not shown) by a method such as vapor deposition or sputtering. A hole injection layer 22 and a hole transport layer 23 are then formed on the first electrode 21 in this order. The hole injection layer 22 and the hole transport layer 23 can be formed by a method such as vacuum deposition, spin coating, casting, or the LB method. Next, an emissive layer 24 is provided on the hole transport layer 23. The emissive layer 24 can also be formed by forming a thin film of a desired organic emissive material by a method such as vacuum deposition, sputtering, spin coating, or casting. Next, an electron transport layer 25 is formed on the emissive layer 24. The electron transport layer 25 can be formed by the same method as the hole transport layer and the emissive layer. Finally, a second electrode 26 is laminated on the electron transport layer 25. The second electrode 26 can be formed by a method such as vapor deposition or sputtering of a desired metal material. The method for forming each layer of the organic EL element is not limited to the above-mentioned methods, and any known method can be appropriately used, such as vacuum deposition, molecular beam deposition (MBE), dipping using a solution in which a material is dissolved in a solvent, spin coating, casting, bar coating, roll coating, or other coating methods.

[0117] The organic electronic device (e.g., photoelectric conversion device, organic EL device) of the present invention and the method for forming each layer of the device are not limited to the device and method described in the above-described embodiment. For example, the materials of the first electrode, light-receiving layer (or light-emitting layer), electron transport layer, and second electrode can be appropriately replaced with other known materials. Furthermore, the hole injection layer and hole transport layer can also be replaced with a layer formed by mixing the compound represented by formula (1) with a hole transport material.

[0118] (Imide Compound) The present invention provides an imide compound represented by the following formula (2) as a particularly novel compound among hole transport materials used in organic electronic devices such as photoelectric conversion devices to improve the hole transport ability. The compound represented by formula (2) is limited to a more preferred range of compounds among the compounds represented by formula (1B).

[0119]

[0120] (In formula (2), Y １ ~Y ７ is N, C—H or C—R ２ where Y １ ~Y ７ If there is one or more Ns, then Y １ , Y ２ , and Y ３ Any one of the following is N, and Y １ ~Y ７ If N is 0, then Y １ ~Y ７ At least one of them is C-R ２ Ring C represents a monocyclic or condensed aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be a ring in which a plurality of aromatic hydrocarbon rings are linked together directly or via a linking group. ２ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. ２ may be bonded to each other to form a cyclic structure, and two R ２ When two R ２ respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, or an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.

[0121] Y in formula (2) １ ~Y ７ and X in the above formula (1B) １ ~X ７ That is, R ２ and R １１ The same content is specified and they are almost synonymous. The difference is that the following proviso is required in formula (2): "However, Y １ ~Y ７ If there is one or more Ns, then Y １ , Y ２ , and Y ３Any one of the following is N, and Y １ ~Y ７ If N is 0, then Y １ ~Y ７ At least one of them is C-R ２ This means that, for example, Y １ ~Y ７ If there is one N in １ ~Y ３ Not Y ４ ~Y ７ In the compound having N in (for example, in the example compound (D-94) above, Y ４ The compounds represented by formula (2) do not include N.

[0122] Except for the above proviso, the requirements defined in formula (2) and formula (1B) are the same, and ring C in formula (2) and ring A in formula (1B) have the same meaning.

[0123] In formula (2), ring C is preferably, for example, any one of the following (C-1) to (C-10).

[0124]

[0125] In formula (2), ring C is preferably (C-1) or (C-2). ３ is N or C-R ２ It is preferable that:

[0126] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. １ The compound was identified based on its H-NMR spectrum (400 MHz). １ H-NMR spectra were measured using a Bruker ASCEND 400 (400 MHz; manufactured by BRUKER). １ H-NMR spectra were obtained using deuterated chloroform (CDCl ３ ) or deuterated dimethyl sulfoxide (DMSO-d ６ The measurement was carried out using tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0127] (Synthesis Example 1: Synthesis of Compound (D-4))

[0128]

[0129] Under an argon stream, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.50 g, 5.59 mmol), 4-aminoquinoline (1.80 g, 12.5 mmol), and isoquinoline (0.62 g, 4.80 mmol) were suspended in m-cresol (29 mL) and stirred at 120°C for 6 hours. After cooling to room temperature, 60 mL of toluene was added to cause crystallization, and the precipitate was collected by filtration. The obtained crude product was purified by recrystallization from DMF to obtain the target compound (D-4) (2.16 g, yield 74%). The obtained compound (D-26) was identified as follows: １ H-NMR was used. １ H-NMR (DMSO-d6) δ (ppm): 7.63 (t, J = 7.6 Hz, 2H), 7.85 (d, J = 4.5 Hz, 2H), 7.88 (t, J = 7.5 Hz , 2H), 8.17 (d, J = 8.6Hz, 2H), 8.22 (d, J = 8.4Hz, 2H), 8.80 (s, 4H), 9.17 (d, J = 4.5Hz, 2H).

[0130] (Synthesis Example 2: Synthesis of compound (D-26))

[0131] Under an argon stream, naphthalene-1,4,5,8-tetracarboxylic dianhydride (1.80 g, 6.71 mmol), 4-amino-1-naphthalenecarbonitrile (2.50 g, 14.9 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.75 g, 6.71 mmol) were suspended in DMF (34 mL) and stirred at 140°C for 14 hours. After cooling to room temperature, an excess amount of water was added to cause crystallization, and the precipitate was collected by filtration. The obtained crude product was purified by recrystallization from DMF to obtain the target compound (D-26) (2.20 g, yield 58%). The obtained compound (D-26) was identified as follows: １ H-NMR was used. １H-NMR (DMSO-d6) δ (ppm): 7.73 (t, J = 8.0 Hz, 2H), 7.92 (t, J = 8.2 Hz, 2H), 8.02 ( d, d=7.7Hz, 2H), 8.30 (brd, J=9.5Hz, 4H), 8.44 (d, J=7.6Hz, 2H), 8.79 (s, 4H).

[0132] (Synthesis Example 3: Synthesis of Compound (D-2))

[0133]

[0134] Compound D-2 was synthesized in the same manner as in Synthesis Example 1, except that 4-aminoquinoline was replaced with 1-aminonaphthalene. １ H-NMR (DMSO-d6) δ (ppm): 7.50 (t, J = 7.3 Hz, 2H), 7.61 (t, J = 6.9, 2H), 7.69 -7.77 (m, 4H), 7.96 (d, J=7.9Hz, 2H), 8.12 (t, J=7.6Hz, 4H), 8.78 (s, 4H).

[0135] (Synthesis Example 4: Synthesis of compound (D-122))

[0136]

[0137] Compound D-122 was synthesized in the same manner as in Synthesis Example 1, except that 4-aminoquinoline was changed to 5-aminoquinoline. １ H-NMR (DMSO-d6) δ (ppm): 7.54 (dd, J = 8.4, 4.3Hz, 2H), 7.86 (d, J = 7.9Hz, 2H), 7.98 (t, J = 7.9H z, 2H), 8.23 ​​(d, J = 8.4Hz, 2H), 8.54 (d, J = 7.9Hz, 2H), 8.78 (s, 4H), 9.00 (dd, J = 4.3, 1.7Hz, 2H).

[0138] (Synthesis Example 5: Synthesis of compound (D-124))

[0139]

[0140] Compound D-124 was synthesized in the same manner as in Synthesis Example 1, except that 4-aminoquinoline was changed to 5-aminoisoquinoline. １H-NMR (DMSO-d6) δ (ppm): 7.84 (d, J = 6.0 Hz, 2H), 7.89 (t, J = 8.0 Hz, 2H), 7.99 (d, J = 8 0Hz, 2H), 8.32 (d, J=8.0Hz, 2H), 8.48 (d, J=6.0Hz, 2H), 8.79 (s, 4H), 9.47 (s, 2H).

[0141] (Synthesis Example 6: Synthesis of compound (D-22))

[0142]

[0143] Compound D-22 was synthesized in the same manner as in Synthesis Example 1, except that 4-aminoquinoline was replaced with 4-amino-2-quinolinecarbonitrile. Since this compound is poorly soluble in heavy solvents, the structure was confirmed by FT-IR. IR: 2355, 1717, 1678, 1583, 1361, 1314, 1250, 1200, 982, 886, 772, 661, 618 cm －１

[0144] (Synthesis Example 7: Synthesis of Compound (D-1))

[0145]

[0146] Compound D-1 was synthesized in the same manner as in Synthesis Example 1, except that naphthalene-1,4,5,8-tetracarboxylic dianhydride and 4-aminoquinoline were replaced with benzene-1,2,4,5-tetracarboxylic anhydride and 4-aminonaphthalene, respectively. １ H-NMR (DMSO-d6) δ (ppm): 7.60 (t, J = 7.7 Hz, 2H), 7.66 (t, J = 8.2 Hz, 2H), 7.73 (t, J = 7.5 Hz, 2H), 7.78 (d, J = 7.2 Hz, 2H) , 7.89 (d, J = 8.2 Hz, 1H), 7.94 (d, J = 8.2 Hz, 1H), 8.12 (d, J = 8.1 Hz, 2H), 8.17 (d, J = 8.2 Hz, 2H), 8.52 (d, J = 8.5 Hz, 2H).

[0147] (Synthesis Example 8: Synthesis of Compound (D-3))

[0148]

[0149] Compound D-3 was synthesized in the same manner as in Synthesis Example 1, except that naphthalene-1,4,5,8-tetracarboxylic dianhydride was replaced with benzene-1,2,4,5-tetracarboxylic anhydride. １ H-NMR (DMSO-d6) δ (ppm): 7.70 (d, J = 7.7 Hz, 2H), 7.82 (dd, J = 4.7, 3.4 Hz, 2H), 7.91 (t, J = 7.6 Hz, 2H), 8.09 (d, J = 8.4Hz, 1H), 8.12 (d, J = 8.4Hz, 1H), 8.22 (d, J = 8.3Hz, 2H), 8.57 (d, J = 3.7Hz, 2H).

[0150] [Compounds used in evaluation]

[0151] <Fabrication and Evaluation of Hole-Only Device (HOD)> [Element Example 1] A hole-only device (HOD) having a structure consisting of a first electrode / hole injection layer / hole transport layer / hole transport promotion layer / second electrode was fabricated, and the hole transport properties of the device were evaluated. (First Electrode) A glass substrate with an ITO transparent electrode, on whose surface an ITO film (thickness 110 nm) was patterned in a stripe shape, was prepared as a substrate having a first electrode. This substrate was washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet cleaning.

[0152] (Preparation for Vacuum Vapor Deposition) Each layer was vacuum-deposited by a vacuum deposition method on the surface on which the ITO film was formed, of the two surfaces of the substrate that had been subjected to the surface treatment described above. First, the glass substrate was placed in a vacuum deposition chamber, and 1.0 × 10 －４ The pressure was reduced to Pa. Then, each layer was formed in the following order according to the film formation conditions.

[0153] (Fabrication of hole injection layer) MoO ３ A 1 nm thick film was formed to prepare a hole injection layer. (Preparation of Hole Transport Layer) A 100 nm thick film of (HTL-1) was formed as a hole transport material to prepare a hole transport layer. (HTL-1) was synthesized by the method described in JP 2018-193371 A. (Preparation of Hole Transport Promotion Layer) A 10 nm thick film of the sublimation-purified compound (D-4) was formed to prepare a hole transport promotion layer.

[0154] (Fabrication of Second Electrode) A 80 nm thick Au film was formed to fabricate a second electrode.

[0155] (Evaluation of hole transport capability of hole-only device) A positive electric field and a negative electric field of 10 mA / cm were applied to the first electrode and the second electrode of the hole-only device of Example 1, respectively. ２ The voltage value at a current density of 1000 kJ / s was measured. The results are shown in Table 1.

[0156] [Comparative Element Example 1] A hole-only device was fabricated in the same manner as in Element Example 1, except that the hole-transport promoting layer was not provided. The hole-transport capability of the resulting hole-only device was evaluated in the same manner as in Element Example 1. The results are shown in Table 1.

[0157]

[0158] The device of Example 1, which used the compound (D-4) as the hole transport promoting material, exhibited a lower voltage than the device of Comparative Example 1, which did not use the hole transport promoting material.

[0159] <Preparation and Evaluation of Photoelectric Conversion Element> [Element Example 2] A photoelectric conversion element 1 having a layered structure consisting of a substrate / second electrode 16 / electron transport layer 15 / light-receiving layer 14 / hole transport layer 13 / hole transport promotion layer 12 / first electrode 11 was prepared, and the dark current and external quantum efficiency of the photoelectric conversion element were evaluated.

[0160] (Preparation of Substrate and Second Electrode 16) A glass substrate with an ITO transparent electrode, on which a 2 mm wide indium-tin oxide (ITO) film (film thickness 110 nm) was patterned in stripes, was prepared as a substrate having a second electrode on its surface. Next, this substrate was washed with isopropyl alcohol, and then subjected to surface treatment by ozone ultraviolet cleaning. (Preparation of Vacuum Vapor Deposition) Each layer was vacuum-deposited by vacuum deposition on the surface-treated substrate after cleaning, and each layer was laminated. First, the glass substrate was placed in a vacuum deposition chamber, and 7.0 × 10 －５The pressure was reduced to 100 Pa. Then, each layer was fabricated in the following order according to the film formation conditions. (Fabrication of Electron Transport Layer 15) The compound 4,6-bis(3,5-di(pyridin-4-yl)phenyl)-2-methylpyrimidine, which had been purified by sublimation, was deposited to a thickness of 10 nm at a rate of 0.03 nm / sec to fabricate the electron transport layer 15. (Fabrication of Light Receiving Layer 14) N,N-dimethylquinacridone and fullerene C60 were deposited in a mass ratio of 4:1 to fabricate the photoelectric conversion layer 14, forming a film of 250 nm. The film formation rate was 0.13 nm / sec. (Fabrication of Hole Transport Layer 13) The hole transport material (HTL-1) was deposited to a thickness of 10 nm at a rate of 0.10 nm / sec to fabricate the hole transport layer 13. (Preparation of Hole Transport Promotion Layer 12) Compound (D-4) was deposited at a rate of 0.20 nm / sec to a thickness of 10 nm to prepare a hole transport promotion layer 12. (Preparation of First Electrode 11) Finally, a metal mask was placed perpendicular to the ITO stripes on the substrate, and the first electrode 11 was deposited. For the first electrode, an Au film was deposited to a thickness of 80 nm. The Au film deposition rate was 0.1 nm / sec.

[0161] From the above, the area is 4 mm ２ A photoelectric conversion element 1 shown in FIG. 1 was fabricated. A voltage of 2.5 V (absolute value) was applied to the photoelectric conversion element fabricated as described above so that electrons were transported to the second electrode 16 side and holes were transported to the first electrode 11 side. The current in the dark (dark current, mA / cm ２ The dark current was measured using a Keithley Source Measure Unit 2636B. The external quantum efficiency was measured using a solar cell spectral response measurement device (Soma Optical Co., Ltd.). The wavelength of the irradiated light was 560 nm, and the intensity was 50 μW / cm. ２ The measurements were carried out at 100°C. The results are shown in Table 2. The dark current and external quantum efficiency are relative values, with the result of Comparative Example 2 of the device described below being set as the reference value (100). The lower the dark current value, the better the performance, and the higher the external quantum efficiency value, the better the performance.

[0162] [Element Example 3] Photoelectric conversion element 1 of Element Example 3 was prepared in the same manner as in Element Example 2, except that compound (D-26) was used instead of compound (D-4) in the preparation of the hole transport promotion layer 12, and the dark current and external quantum efficiency were measured in the same manner as in Element Example 2. The results are shown in Table 2.

[0163] [Element Comparative Example 2] In the preparation of the hole transport promotion layer 12, the photoelectric conversion element 1 of Element Comparative Example 2 was prepared in the same manner as in Element Example 2, except that the following compound (R-1) was used instead of compound (D-4). The dark current and external quantum efficiency were measured in the same manner as in Element Example 2. The results are shown in Table 2. The compound (R-1) was synthesized by the method described in Dyes and Pigments (2021), 193, 109505.

[0164]

[0165] [Element Comparative Example 3] A photoelectric conversion element of Element Comparative Example 3 was prepared in the same manner as in Element Example 2, except that the hole transport promotion layer 12 was not provided, and the dark current was measured in the same manner as in Element Example 2. The results are shown in Table 2. In Element Comparative Example 3, the dark current was too large to measure the external quantum efficiency.

[0166]

[0167] As shown in Table 2, in the elements of Element Example 2 and Element Example 3 using the material for a photoelectric conversion element for an imaging element of the present invention, dark current was suppressed and high external quantum efficiency was obtained compared to the elements of Element Comparative Example 2 and Element Comparative Example 3. Similar effects were also confirmed for compounds (D-1), (D-2), (D-3), (D-22), (D-122), and (D-124).

[0168] <Film Quality Evaluation of Hole Transport Promotion Layer> [Example A-1] For the laminate in which the hole transport promotion layer was formed on the first electrode in Device Example 1, the arithmetic mean roughness (nm) of the surface of the hole transport promotion layer was measured using an atomic force microscope (Shimadzu Corporation, SPM-9600). The results are shown in Table 3 below.

[0169] [Example A-2] A laminate was prepared by forming a film of compound (D-26) on the first electrode instead of the compound of formula (D-4) used in preparing the hole transport promotion layer in Example A-1, and the film quality was evaluated in the same manner as in Example A-1. The results are shown in Table 3 below.

[0170] Comparative Reference Example B-1 A laminate was prepared by forming a film of the following compound (R-2) on the first electrode instead of the compound of formula (D-4) used in preparing the hole transport promotion layer in Example A-1, and the film quality was evaluated in the same manner as in Example A-1. The results are shown in Table 3 below. Compound (R-2) was synthesized by the method described in WO2008 / 072586.

[0171]

[0172] Comparative Reference Example B-2 A laminate was prepared in which the following compound (R-3) was formed on the first electrode instead of the compound of formula (D-4) used in preparing the hole transport promotion layer in Example A-1, and the film quality was evaluated in the same manner as in Example A-1. The results are shown in Table 3 below. Compound (R-3) was synthesized by the method described in Journal of Materials Chemistry A: Materials for Energy and Sustainability (2015), 3(2), 878-885.

[0173]

[0174]

[0175] By including the compound represented by formula (1), the organic electronic device of the present invention can improve the hole transport capability, and when used in a photoelectric conversion device, photoelectric conversion can be performed more efficiently. Furthermore, by including the compound represented by formula (1), the organic electronic device of the present invention suppresses dark current, and is expected to reduce noise when used in a photoelectric conversion device such as an imaging device. Furthermore, by including the compound represented by formula (1), the organic electronic device of the present invention can have high external quantum efficiency and can convert light into current without loss, so that, for example, when used in a photoelectric conversion device, high sensitivity is expected. From the results in Table 3, it can be seen that the hole transport promotion layer prepared using the compound represented by formula (1) has flatter film quality than the hole transport promotion layer of the comparative example. Because the film quality is flat, good adhesion with adjacent layers can be achieved. This good adhesion is also thought to be effective in efficiently transporting holes.

[0176] 1. Photoelectric conversion element 11. First electrode 12. Hole transport promoting layer 13. Hole transport layer 14. Light receiving layer 15. Electron transport layer 16. Second electrode 2. Organic EL element 21. First electrode 22. Hole injection layer 23. Hole transport layer 24. Light emitting layer 25. Electron transport layer 26. Second electrode

Claims

1. An organic electronic device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a structure represented by the following formula (1): (In formula (1), Ar １ is a substituent R １ a fused heteroaromatic group having two, three or four rings formed solely of six-membered rings, which may have one or more substituents R １ represents a fused aromatic hydrocarbon group having two, three or four rings, which may have one or more Ar １ are the same. 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 together directly or via a linking group. R １ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may also be a group in which these substituents are combined.

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

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

4. The organic electronic device according to claim 3, wherein the hole transport layer and the hole transport promotion layer are disposed adjacent to each other between the first electrode and the second electrode.

5. The organic electronic device according to claim 1, wherein in the formula (1), the ring A is represented by any one of the following (A-1) to (A-10):

6. The organic electronic device according to claim 5, wherein in formula (1), ring A is (A-1) or (A-2).

7. In the formula (1), the Ar １ is a substituent R １ 2. The organic electronic device according to claim 1, wherein the alkyl group is a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, a benzofluorenyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, an acridyl group, a naphthyridyl group, a quinoxalyl group, a pyridopyrazyl group, a pteridyl group, a pyrazinopyrazyl group, a pyrimidopyrimidyl group, a benzoquinolyl group, a benzoisoquinolyl group, an acridyl group, a benzoquinazolyl group, a phenanthridyl group, or a phenanthrolyl group, each of which may have one or more of the following:

8. In the formula (1), Ar １ The organic electronic device according to claim 1 , wherein the organic electronic device has a partial structure represented by the following formula (B): (In formula (B), X １ ~X ７ are N, C—H or C—R, respectively. １１ Represents R １１ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. １１ may be bonded to each other to form a cyclic structure, and two R １１ When two R １１ respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, or an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.

9. In the formula (1), R １ is a cyano group, a methyl group, a fluoro group, or CF ３ 2. The organic electronic device according to claim 1, wherein the alkyl group is a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a quinolyl group, an isoquinolyl group, or a combination of these groups.

10. A hole transport promoting material represented by the following formula (1): (In formula (1), Ar １ is a substituent R １ a fused heteroaromatic group having two, three or four rings formed solely of six-membered rings, which may have one or more substituents R １ represents a fused aromatic hydrocarbon group having two, three or four rings, which may have one or more Ar １ are the same. 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 together directly or via a linking group. R １ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may also be a group in which these substituents are combined.

11. The hole transport promoting material according to claim 10, wherein in formula (1), ring A is represented by any one of the following (A-1) to (A-10):

12. The hole transport promoting material according to claim 10, wherein in formula (1), ring A is (A-1) or (A-2).

13. In the formula (1), the Ar １ is a substituent R １ 11. The hole transport promoting material according to claim 10, wherein the aromatic hydrocarbon group is a naphthyl group, phenanthryl group, anthryl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, benzofluorenyl group, quinolyl group, isoquinolyl group, quinazolyl group, acridyl group, naphthyridyl group, quinoxalyl group, pyridopyrazyl group, pteridyl group, pyrazinopyrazyl group, pyrimidopyrimidyl group, benzoquinolyl group, benzoisoquinolyl group, acridyl group, benzoquinazolyl group, phenanthridyl group, or phenanthrolyl group, each of which optionally has one or more of the following substituents:

14. In the formula (1), Ar １ The hole transport promoting material according to claim 10 , wherein the compound has a partial structure represented by the following formula (B): (In formula (B), X １ ~X ７ are N, C—H or C—R, respectively. １１ Represents R １１ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. １１ may be bonded to each other to form a cyclic structure, and two R １１ When two R １１ respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, or an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.

15. In the formula (1), R １ is a cyano group, a methyl group, a fluoro group, or CF ３ 11. The hole transport promoting material according to claim 10, wherein the aryl group is a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a quinolyl group, an isoquinolyl group, or a combination of these groups.

16. An imide compound represented by the following formula (2): (In formula (2), Y １ ~Y ７ is N, C—H or C—R ２ where Y １ ~Y ７ If there is one or more Ns, then Y １ , Y ２ , and Y ３ Any one of the following is N, and Y １ ~Y ７ If N is 0, then Y １ ~Y ７ At least one of them is C-R ２ Ring C represents a monocyclic or condensed aromatic hydrocarbon ring. The aromatic hydrocarbon ring may be a ring in which a plurality of aromatic hydrocarbon rings are linked together directly or via a linking group. ２ represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, a heteroaromatic group having 3 to 30 carbon atoms, a cyano group, F, Cl, Br, CF ３ , a perfluoroalkyl group having 2 to 15 carbon atoms, or an alkyl group having 1 to 15 carbon atoms which may have a cyclic structure, and may be a group in which these substituents are combined. ２ may be bonded to each other to form a cyclic structure, and two R ２ When two R ２ respectively represent N, O, a hydrocarbon group having 1 to 4 carbon atoms, or an unsaturated hydrocarbon group having 1 to 4 carbon atoms, and may be a group formed by combining these groups.

17. The imide compound according to claim 16, wherein in formula (2), ring C is represented by any one of the following (C-1) to (C-10):

18. The imide compound according to claim 17, wherein in formula (2), ring C is (C-1) or (C-2).

19. In the formula (2), Y ３ is N or C-R ２ The imide compound according to claim 16, wherein

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