Organic electronic element and azaimide-based compound

Abstract

The present invention provides: an organic electronic element capable of improving hole transport capability in a p-type region; and an azaimide-based compound used for the organic electronic element.　The organic electronic element comprises a first electrode, a second electrode, and a hole transport region disposed between the first electrode and the second electrode. The hole transport region includes a hole transport layer and a hole transport promoting layer containing a compound represented by formula (1), or includes a layer formed by mixing a hole transport material and a compound represented by formula (1). (In formula (1), X1, X2, X3, and X4 are each independently a nitrogen atom or C-R. At least one among X1 to X4 is a nitrogen atom.　R represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, or an optionally substituted alkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, heteroaryloxy group, alkoxycarbonyl group, aryloxycarbonyl group, or heteroaryloxycarbonyl group.　Ra and Rb each independently represent an optionally substituted alkyl group, aryl group, or heteroaryl group.)

Description

Organic electronic device and azaimide compound

[0001] The present invention relates to an organic electronic device and an azaimide 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 charge carriers (electrons and holes) generated in the light-receiving layer to the electrodes in order to suppress the cause of image retention. Furthermore, organic EL elements are required to quickly transport charge carriers from the electrodes to the light-emitting layer in order to suppress an increase in driving voltage. Thus, in order to improve device performance, high efficiency charge carrier movement within the element is required.

[0003] Incidentally, with regard to an n-type organic semiconductor material, an organic semiconductor film-forming composition containing the same, an organic semiconductor film containing the same, and an organic thin-film transistor, Patent Document 1 discloses the use of azanaphthalenediimide as an n-type organic semiconductor material, a so-called electron transport material.

[0004] International Publication No. 2019-176634

[0005] However, in the field of organic electronic devices, further improvements in performance are required, and there is a constant demand for an organic electronic device capable of improving the hole transport capability in the p-type region. An object of the present invention is to provide an organic electronic device capable of improving the hole transport capability in the p-type region, and an azaimide compound for use in the organic electronic device.

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

[0007] That is, the present invention includes the following aspects: [1] An organic electronic device including a first electrode, a second electrode, and a hole transport region disposed between the first electrode and the second electrode, wherein the hole transport region includes a hole transport layer and a hole transport promoting layer containing a compound represented by the following formula (1), or includes a layer formed by mixing a hole transport material and a compound represented by the following formula (1): (In formula (1), X １ , X ２ , X ３ and X ４ each independently represents a nitrogen atom or C—R. １ ~X ４ At least one of the groups is a nitrogen atom. R represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. R ａ and R ｂ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms.) [2] X １ ~X ４ Among them, X is a nitrogen atom １ ~X ４ [3] The organic electronic device according to [1], wherein the number of X １ ~X ４ Among them, X is a nitrogen atom １ ~X ４ [4] The organic electronic device according to [2], wherein the number of X １ ~X４ Of these, X １ is a nitrogen atom, or X １ and X ３[5] The organic electronic device according to [3], wherein R is a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, a cyanomethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a carboxy group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a fluoropyrimidyl group, a trifluoromethylpyrimidyl group, a triazyl group, a cyanotriazyl group, a fluorotriazyl group, a trifluoromethyltriazyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, [4] The organic electronic device according to any one of [1] to [4], wherein the alkyl group is a methoxy group, an ethoxy group, a perfluoroethoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a phenoxy group, a cyanophenoxy group, a pyridyloxy group, a quinolyloxy group, a methoxycarbonyl group, or an ethoxycarbonyl group.[6] The organic electronic device according to [5], wherein R is a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, a methylpropyl group, an ethylpropyl group, a methylbutyl group, a hexyl group, a cyanomethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a fluoropyrimidyl group, a trifluoromethylpyrimidyl group, a perfluoroethoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a phenoxy group, a cyanophenoxy group, or a pyridyloxy group. [7] The organic electronic device according to [6], wherein R is a hydrogen atom, a cyano group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, or a trifluoromethylpyridyl group. ａ and R ｂeach independently represents a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a fluoronaphthyl group, a trifluoromethylnaphthyl group, The organic electronic device according to any one of [1] to [7], wherein R is a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, a benzimidazolyl group, or a cyanobenzimidazolyl group. [9] R ａ and R ｂare each independently a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a fluoronaphthyl group, a trifluoromethylnaphthyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, or a trifluoromethylimidazolyl group.

[10] R ａ and R ｂ are each independently a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a cyanothiazolyl group, an imidazolyl group, or a cyanoimidazolyl group.

[11] The organic electronic device according to any one of [1] to

[10] , further comprising an absorption layer disposed between the first electrode and the second electrode.

[12] The organic electronic device according to

[11] , wherein the absorption layer is a layer containing at least two organic components.

[13] A compound represented by the following formula (2) or (3): (In formula (2) and formula (3), R １represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, a substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. R ｃ , R ｄ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms, provided that R ｃ , R ｄ is an unsubstituted or fluorine-substituted linear alkyl group having 1 to 10 carbon atoms, a cyclohexyl group, or a fluorine-substituted aryl group, R １ is a substituent other than a hydrogen atom or a phenyl group. ２ , R ３ , R ４ , and R ５ R each independently represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. ｅ , and R ｆeach independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms, provided that R ｅ , R ｆ When R is a cyclohexyl group, ４ and R ５ is a substituent other than a hydrogen atom.)

[14] R １ ~R ５ are each independently a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a triazyl group, a cyanotriazyl group, a quinolyl group, a cyanoquinolyl group, a phenoxy group, a cyanophenoxy group, a pyridyloxy group, a quinolyloxy group, a methoxycarbonyl group, or an ethoxycarbonyl group. １ ~R ５ are each independently a hydrogen atom, a cyano group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, or a cyanoquinolyl group.

[16] The compound according to

[14] , ｃ , R ｄ , R ｅ , and R ｆeach independently represents a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, The compound according to any one of

[13] to

[15] , which is a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, a benzimidazolyl group, or a cyanobenzimidazolyl group.

[17] R ｃ , R ｄ , R ｅ , and R ｆeach independently represents a cyclohexylmethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, The compound according to

[16] , wherein R is a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a thiazolyl group, a cyanothiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a benzimidazolyl group, or a cyanobenzimidazolyl group.

[18] R ｃ , R ｄ , R ｅ , and R ｆ are each independently a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a thiazolyl group, a cyanothiazolyl group, an imidazolyl group, a cyanoimidazolyl group, or a benzimidazolyl group.

[0008] According to the present invention, it is possible to provide an organic electronic device capable of improving the hole transport capability in the p-type region, and an azaimide compound for use in the organic electronic device.

[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 a hole transport region disposed between the first electrode and the second electrode. The hole transport region includes a hole transport layer and a hole transport promoting layer containing a compound represented by the following formula (1), or includes a layer comprising a mixture of a hole transport material and a compound represented by the following formula (1). The organic electronic device of the present invention is an organic device including a hole transport promoting material containing a specific compound represented by formula (1). The organic electronic device of the present invention is a p-type organic semiconductor device that enables hole transport promotion in a p-type region.

[0012] The compound represented by the above formula (1) will be described in detail later. 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 the above formula (1) is used as a hole transport promoting material, as an organic semiconductor material that enables the promotion of hole transport in a p-type region.

[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 a hole transport region 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 a 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 a hole transport region disposed between the first electrode and the second electrode. The hole transport region refers to the region between the first electrode and the light-receiving layer, and includes, for example, a hole transport layer and a hole transport promoting layer. In the present invention, the compound represented by the above formula (1) can be used as the hole transport promoting material contained in the hole transport promoting layer. The hole transport region is preferably adjacent to the first electrode. The photoelectric conversion element may include other layers. Examples of the 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 a hole transport region disposed between the first electrode and the second electrode. 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 hole transport region in the organic electronic device of the present invention contains a compound represented by the following formula (1) (azamide compound).

[0025]

[0026] In formula (1), X １ , X ２ , X ３ and X ４ each independently represents a nitrogen atom or C—R. １ ~X ４At least one of the groups is a nitrogen atom. R represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. R ａ and R ｂ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms.

[0027] In this specification, examples of substituents defined as "optionally substituted" include substituents such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclohexyl group, an ethylhexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a diamantyl group, a cyano group, a cyanomethyl group, a nitro group, an amino group, a hydroxyl group, a fluoro group, a trifluoromethyl group, a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a pyrimidyl group, a triazyl group, a furyl group, a thienyl group, an acetyl group, a methoxycarbonyl group, or an amido group.

[0028] In this specification, examples of the "alkyl group" include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a 2-methylcyclopropyl group, a cyclobutyl group, an n-pentyl group, a 2-pentyl group, a 3-pentyl group, a neopentyl group, an isopentyl group, a 2-methylbutyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a cyclopentyl group, a 2-methylcyclobutyl group, an n-hexyl group, a 2-hexyl group, a 3-hexyl group, and a 2-methylpentyl group. , 3-methylpentyl group, 4-methylpentyl group, 2-ethylbutyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, cyclohexyl group, n-heptyl group, 2-heptyl group, 3-heptyl group, cycloheptyl group, bicyclo[2.2.1]heptyl group, n-octyl group, 2-octyl group, 3-octyl group, 4-octyl group, cyclooctyl group, bicyclo[2.2.2]octyl group, 1-decyl group, adamantyl group, or diamantyl group.

[0029] In this specification, examples of the "aryl group" include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a fluorenyl group, a phenanthryl group, a benzofluorenyl group, a triphenylenyl group, a fluoranthenyl group, etc. Among these, a phenyl group, a biphenyl group, and a naphthyl group are preferred in terms of ease of synthesis, and a phenyl group and a naphthyl group are preferred in terms of good vapor deposition properties of the material.

[0030] In the present specification, examples of the "heteroaryl group" include Examples thereof include a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a phenylpyridyl group, a pyridylphenyl group, a pyrazyl group, a pyrimidyl group, a 1,3,5-triazyl group, a phenanthrolyl group, an indolyl group, a benzothienyl group, a benzofuranyl group, a benzimidazolyl group, an indazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a 2,1,3-benzothiadiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a 2,1,3-benzoxadiazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a carbazolyl group, a dibenzothienyl group, a dibenzofuranyl group, a phenoxazinyl group, a phenothiazinyl group, a phenazine group, and a thianthrenyl group. Among these, a pyridyl group, a thienyl group, a thiazolyl group, a quinolyl group, a pyrazyl group, a pyrimidyl group, and a 1,3,5-triazyl group are preferred in terms of ease of synthesis, and a pyridyl group, a quinolyl group, an imidazolyl group, and a thiazolyl group are more preferred in terms of contributing to improving the performance of organic electronic devices.

[0031] In this specification, examples of the "alkoxy group" include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, a phenoxy group, a naphthoxy group, a pyridyloxy group, a quinolyloxy group, and a phenanthryloxy group.

[0032] X １ ~X ４ Among them, X is a nitrogen atom １ ~X ４ The number of X is preferably 3 or less, and more preferably 2 or less. １ ~X ４ A preferred embodiment of X １ ~X ４ Of these, X １ is a nitrogen atom, or X １ ~X ４ Of these, X １ and X ３ is a nitrogen atom.

[0033] Examples of R include a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a cycloheptyl group, a cyclooctyl group, a cyanomethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a carboxy group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a fluoropyrimidyl group, a trifluoromethylpyrimidyl group, a triazyl group, a cyanotriazyl group, a fluorotriazyl group, a trifluoromethyltriazyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, Examples of the alkyl group include a methoxy group, an ethoxy group, a perfluoroethoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a phenoxy group, a cyanophenoxy group, a pyridyloxy group, a quinolyloxy group, a methoxycarbonyl group, and an ethoxycarbonyl group.

[0034] More preferred examples of R include a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, a methylpropyl group, an ethylpropyl group, a methylbutyl group, a hexyl group, a cycloheptyl group, a cyclooctyl group, a cyanomethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a fluoropyrimidyl group, a trifluoromethylpyrimidyl group, a perfluoroethoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a phenoxy group, a cyanophenoxy group, and a pyridyloxy group.

[0035] More preferred examples of R include a hydrogen atom, a cyano group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, and a trifluoromethylpyridyl group.

[0036] R ａ and R ｂExamples of the groups which can be used herein are, independently, a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, a decyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a fluoronaphthyl group, a trifluoromethylnaphthyl group, Examples of such groups include a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, a benzimidazolyl group, and a cyanobenzimidazolyl group.

[0037] R ａ and R ｂMore preferred examples of the groups independently include a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a fluoronaphthyl group, a trifluoromethylnaphthyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, and a trifluoromethylimidazolyl group.

[0038] R ａ and R ｂ More preferred examples of the groups are each independently a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a cyanothiazolyl group, an imidazolyl group, or a cyanoimidazolyl group.

[0039] 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.

[0040] The compound represented by formula (1) is used as a part of a p-type semiconductor organic electronic device, for example, as a hole injection layer, a hole transport promoting layer, etc. In particular, the compound represented by formula (1) is preferably used in a hole transport promoting layer.

[0041] Preferred examples of the azaimide compound represented by formula (1) include the following (A-1) to (A-314). For example, the embodiments that each group can take will be specifically explained using the following exemplary compounds. In the compound represented by (A-140) below, R １ is an aryl group substituted with a cyano group. In the compound shown in (A-3) below, R ａ , R ｂ is an ethyl group substituted with a cyclohexyl group. In the compound shown below in (A-160), R ａ , R ｂ is an alkyl group substituted with a cyano group. The compounds of the present invention are not limited to the following (A-1) to (A-314).

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] [Production Method] The compound represented by the above formula (1) can be synthesized by a known method or a combination thereof (for example, an oxidation reaction of naphthalenediimide and a condensation reaction with methyleneamine, etc.). For example, the compound represented by formula (1) can be synthesized by the synthetic route shown below.

[0086]

[0087] <<Action and Effect of the Compound Represented by Formula (1)>> The compound represented by formula (1) has an azanaphthalenecarboxylic 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 an azanaphthalenecarboxylic acid diimide skeleton or a specific skeleton structure similar thereto, it is also expected that it will have thermal stability, high reduction resistance, and the like.

[0088] 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 also 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.

[0089] <<Hole Transport Promoting Material>> As described above, the compound represented by formula (1) is used in the hole transport promoting layer as a hole transport promoting material.

[0090] <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".

[0091] 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.

[0092] <<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.

[0093] 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.

[0094] [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.

[0095] 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.

[0096] 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.

[0097] [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.

[0098] [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.

[0099] 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.

[0100] [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.

[0101] 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).

[0102] 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.

[0103] (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.

[0104] 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).

[0105] [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.

[0106] 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.

[0107] 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.

[0108] [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.

[0109] [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.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] 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.

[0114] <<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.

[0115] [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).

[0116] [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.

[0117] [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.

[0118] [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.

[0119] [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.

[0120] [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.

[0121] 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.

[0122] [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.

[0123] <<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.

[0124] [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.

[0125] 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.

[0126] [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.

[0127] [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.

[0128] [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.

[0129] [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.

[0130] [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.

[0131] [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.

[0132] 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.

[0133] (Azamide-Based Compound) The present invention provides an azamide-based compound represented by the following formula (2) or (3) 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 azamide-based compound represented by formula (2) or (3) is limited to a more preferred range of compounds among the compounds represented by formula (1).

[0134]

[0135] (In formula (2) and formula (3), R １ represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, a substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. R ｃ , R ｄ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms, provided that R ｃ , R ｄ is an unsubstituted or fluorine-substituted linear alkyl group having 1 to 10 carbon atoms, a cyclohexyl group, or a fluorine-substituted aryl group, R １ is a substituent other than a hydrogen atom or a phenyl group. ２ , R ３ , R ４ , and R ５R each independently represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. ｅ , and R ｆ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms, provided that R ｅ , R ｆ When R is a cyclohexyl group, ４ and R ５ is a substituent other than a hydrogen atom.)

[0136] R in formula (2) ２ ~R ３ and R in the above formula (1) define the same thing. １ and R in the above formula (1) have almost the same definitions, but R １ The definition of R in formula (2) differs from that of R in formula (1) in that the aryl group in formula (2) is limited to a substituted aryl group. ｃ ~R ｄ and R in the above formula (1) ａ ~R ｂ The formula (2) defines the same content as the formula (1). In addition, the position of N in the naphthalene skeleton is specified, and the formula (2) differs from the formula (1) in that it requires the following proviso: ｃ , R ｄis an unsubstituted or fluorine-substituted linear alkyl group having 1 to 10 carbon atoms, a cyclohexyl group, or a fluorine-substituted aryl group, R １ is a substituent other than a hydrogen atom or a phenyl group. ｃ , R ｄ is an unsubstituted linear alkyl group having 1 to 10 carbon atoms, R ２ , R ３ Even if satisfies the above requirements, R １ When is a hydrogen atom, such a compound is not included in the compounds represented by formula (2).

[0137] Furthermore, R in formula (3) ４ ~R ５ and R in the above formula (1) define the same thing. ｅ ~R ｆ and R in the above formula (1) ａ ~R ｂ The formula (3) specifies the position of N in the naphthalene skeleton, and differs from the formula (1) in that it also requires the following proviso: ｅ , R ｆ When R is a cyclohexyl group, ４ and R ５ is a substituent other than a hydrogen atom."

[0138] R １ ~R ５ Examples of the groups are each independently a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a triazyl group, a cyanotriazyl group, a quinolyl group, a cyanoquinolyl group, a phenoxy group, a cyanophenoxy group, a pyridyloxy group, a quinolyloxy group, a methoxycarbonyl group, or an ethoxycarbonyl group.

[0139] R １ ~R ５More preferred examples of the aryl group include a hydrogen atom, a cyano group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, and a cyanoquinolyl group.

[0140] R ｃ , R ｄ , R ｅ , and R ｆ Examples of the groups which can be used herein are: each independently a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, Examples of such groups include a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, a benzimidazolyl group, and a cyanobenzimidazolyl group.

[0141] R ｃ , R ｄ , R ｅ , and R ｆExamples of the groups which can be used herein are, independently, a cyclohexylmethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, More preferred examples include a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a thiazolyl group, a cyanothiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a benzimidazolyl group, and a cyanobenzimidazolyl group.

[0142] R ｃ , R ｄ , R ｅ , and R ｆ More preferred examples of the groups are each independently a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a thiazolyl group, a cyanothiazolyl group, an imidazolyl group, a cyanoimidazolyl group, or a benzimidazolyl group.

[0143] 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-d６ The measurement was carried out using tetramethylsilane (TMS) as the internal standard. Commercially available reagents were used.

[0144] (Synthesis Example 1: Synthesis of Compound (A-12))

[0145]

[0146] To a 200 mL three-neck flask, 2.68 g (10.0 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 2.02 g (20.0 mmol) of hexylamine, 0.68 g (10.0 mmol) of imidazole, and 50 mL of N,N-dimethylformamide were added and stirred at 120°C for 12 hours. Then, 10 mL of ethanol was added to the reaction solution and filtered. The resulting solid was dried to obtain 3.90 g of a white solid (A-12p). To a 300 mL three-neck flask, 3.90 g (18.0 mmol) of compound (A-12p), 0.37 g (1.80 mmol) of ruthenium trichloride hydrate, 30.8 g (144 mmol) of sodium periodate, 60 mL of dichloromethane, 60 mL of acetonitrile, and 60 mL of pure water were added and stirred at 35°C for 10 hours. The reaction solution was extracted with chloroform, and the resulting organic layer was concentrated. After that, acetone was added to cause crystallization, yielding 4.36 g of a pale yellow solid (A-12q). 4.36 g (9.90 mmol) of compound (A-12q), 1.00 g (10.9 mmol) of aminoacetonitrile hydrochloride, and 100 mL of N,N-dimethylformamide were added to a 200 mL three-neck flask, and the mixture was stirred at 110°C for 9 hours. Pure water was then added to the reaction solution to cause crystallization, yielding a gray solid. The resulting gray solid was recrystallized using acetone, yielding 3.00 g of the target white solid (A-12). The resulting compound (A-12) was identified as follows: １ H-NMR was used. １ H-NMR (DMSO-d6) δ (ppm): 0.90 (t, J = 6.8 Hz, 3H), 0.91 (t, J = 6.8 Hz, 3H), 1.28-1.48 (m, 1 2H), 1.70-1.83 (m, 4H), 4.19-4.30 (m, 4H), 8.93 (d, J = 7.2Hz, 1H), 9.04 (d, J = 7.2Hz, 1H)

[0147] (Synthesis Example 2: Synthesis of Compound (A-315))

[0148]

[0149] To a 200 mL three-neck flask, 2.68 g (10.0 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 2.60 g (20.0 mmol) of octylamine, 0.68 g (10.0 mmol) of imidazole, and 50 mL of N,N-dimethylformamide were added and stirred at 120°C for 12 hours. Then, 10 mL of ethanol was added to the reaction solution and filtered. The resulting solid was dried to obtain 3.52 g of a white solid (A-315p). To a 300 mL three-neck flask, 4.90 g (10.0 mmol) of compound (A-315p), 0.21 g (1.00 mmol) of ruthenium trichloride hydrate, 17.1 g (80 mmol) of sodium periodate, 35 mL of dichloromethane, 35 mL of acetonitrile, and 35 mL of pure water were added and stirred at 35°C for 10 hours. The reaction solution was extracted with chloroform, and the resulting organic layer was concentrated. After that, acetone was added to cause crystallization, yielding 2.50 g of a pale yellow solid (A-315q). 1.49 g (3.00 mmol) of compound (A-315q), 0.30 g (3.30 mmol) of aminoacetonitrile hydrochloride, and 30 mL of N,N-dimethylformamide were added to a 200 mL three-neck flask, and the mixture was stirred at 110°C for 9 hours. Pure water was then added to the reaction solution to cause crystallization, yielding a gray solid. The resulting gray solid was recrystallized using acetone, yielding 1.19 g of the target white solid (A-315). The resulting compound (A-315) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 0.85-0.88 (m, 6H), 1.26-1.41 (m, 20H), 1.46 (t, J = 7.3Hz, 3H), 1.67-1.76 (m, 4H), 4.14 (t, J = 7.8Hz, 2H), 4.22 (t, J = 7.6Hz, 2H), 4.61 (q, J = 7.2Hz, 2H), 8.81 (d, J = 7.6Hz, 1H), 8.94 (d, J = 7.6Hz, 1H)

[0150] (Synthesis Example 3: Synthesis of compound (A-322))

[0151]

[0152] A 200 mL three-neck flask was charged with 2.68 g (10.0 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 2.60 g (20.0 mmol) of 2-ethylhexylamine, 0.68 g (10.0 mmol) of imidazole, and 50 mL of N,N-dimethylformamide, and the mixture was stirred at 120°C for 12 hours. Then, 10 mL of ethanol was added to the reaction solution, and the mixture was filtered. The resulting solid was dried, yielding 2.91 g of a white solid (A-322p). A 100 mL three-neck flask was charged with 0.99 g (2.01 mmol) of compound (A-322p), 49 mg (0.20 mmol) of ruthenium trichloride hydrate, 3.45 g (16.1 mmol) of sodium periodate, 16 mL of 1,2-dichloroethane, 16 mL of acetonitrile, and 16 mL of pure water, and the mixture was stirred at 35°C for 4 days. The reaction solution was extracted with chloroform and dehydrated over anhydrous sodium sulfate. The solvent was distilled off to obtain a brown solid (A-322q). A 100 mL three-neck flask was charged with (A-322q), 0.28 g (1.31 mmol) of glycine ethyl ester hydrochloride, and 30 mL of N,N-dimethylformamide, and the mixture was stirred at 100°C for 10 hours. Water and ethyl acetate were then added to the reaction solution. The organic layer was separated, washed with saturated brine, and dehydrated over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate 50 / 1) to obtain 0.49 g of the desired light brown solid (A-322). The resulting compound (A-322) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 0.86-0.96 (m, 12H), 1.28-1.41 (m, 16H), 1.46 (t, J = 7.1Hz, 3H), 1.89-1.97 (m, 2 H) 4.07-4.24 (m, 4H), 4.61 (q, J = 7.2Hz, 2H), 8.82 (d, J = 7.3Hz, 1H), 8.95 (d, J = 7.3Hz, 1H)

[0153] (Synthesis Example 4: Synthesis of compound (A-324))

[0154]

[0155] To a 20 mL three-neck flask were added 0.30 g (0.60 mmol) of compound (A-315q), 92 mg (0.66 mmol) of glycine ethyl ester hydrochloride, and 7.5 mL of N,N-dimethylformamide, and the mixture was stirred at 110°C for 10 hours. Water and chloroform were then added to the reaction mixture. The mixture was extracted three times with chloroform. After the solvent was distilled off, the resulting residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dehydrated over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate 20 / 1) to obtain 0.17 g of the target pale brown solid (A-324). The resulting compound (A-324) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 0.85-0.88 (m, 6H), 1.26-1.41 (m, 20H), 1.46 (t, J = 7.3Hz, 3H), 1.67-1.76 (m, 4H), 4.14 (t, J = 7.8Hz, 2H), 4.22 (t, J = 7.6Hz, 2H), 4.61 (q, J = 7.2Hz, 2H), 8.81 (d, J = 7.6Hz, 1H), 8.94 (d, J = 7.6Hz, 1H)

[0156] (Synthesis Example 5: Synthesis of compound (A-329))

[0157]

[0158] To a 20 mL three-neck flask were added 56 mg (0.10 mmol) of compound (A-324), 5.0 mL of 1,4-dioxane, and 0.5 mL of concentrated hydrochloric acid, and the mixture was stirred under heating and reflux for 18 hours. 1.0 mL of concentrated hydrochloric acid was further added, and the mixture was stirred under heating and reflux for 2 days. Water was then added to the reaction solution, and the precipitated solid was filtered. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate / hexane 1 / 1 / 4) to obtain 20 mg of the desired pale yellow solid compound (A-329). The resulting compound (A-329) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３) δ (ppm): 0.88 (t, J=6.8Hz, 6H), 1.28-1.43 (m, 20H), 1.71-1.80 (m, 4H), 4. 18-4.27 (m, 4H), 8.79 (d, J = 7.2Hz, 1H), 8.91 (d, J = 7.2Hz, 1H), 9.81 (s, 1H)

[0159] (Synthesis Example 6: Synthesis of compound (A-335))

[0160]

[0161] To a 100 mL three-neck flask were added 0.18 g (0.32 mmol) of compound (A-324), 8 mg (0.03 mmol) of ruthenium trichloride hydrate, 0.53 g (2.48 mmol) of sodium periodate, 6 mL of dichloromethane, 6 mL of acetonitrile, and 6 mL of pure water, and the mixture was stirred at 30°C for 3 days. The reaction solution was extracted with chloroform and dehydrated over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate 1 / 1) to obtain 123 mg of the desired yellow solid (A-324p). To a 100 mL three-neck flask were added 123 mg (0.22 mmol) of (A-324p), 30 mg (0.22 mmol) of glycine ethyl ester hydrochloride, and 20 mL of tert-butanol, and the mixture was stirred under heating and reflux for 16 hours. Thereafter, the solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate 10 / 1) to obtain 72 mg of the target pale yellow solid (A-335). １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 0.86-0.96 (m, 6H), 1.27-1.41 (m, 20H), 1.48 (t, J = 7.2Hz, 6H), 1.68-1 .80 (m, 4H), 4.12 (t, J=7.6Hz, 2H), 4.29 (t, J=7.6Hz, 2H), 4.64 (q, J=7.2Hz, 4H)

[0162] (Synthesis Example 7: Synthesis of Compound (A-3))

[0163]

[0164] To a 200 mL three-neck flask, 2.68 g (10.0 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 2.54 g (20.0 mmol) of 1-cyclohexyethylamine, 0.68 g (10.0 mmol) of imidazole, and 50 mL of N,N-dimethylformamide were added and stirred at 120°C for 12 hours. Then, 10 mL of ethanol was added to the reaction solution and the mixture was filtered. The resulting solid was dried to obtain 3.79 g of a white solid (A-3p). To a 300 mL three-neck flask, 2.43 g (5.00 mmol) of compound (A-3p), 0.11 g (0.50 mmol) of ruthenium trichloride hydrate, 8.50 g (40 mmol) of sodium periodate, 20 mL of dichloromethane, 20 mL of acetonitrile, and 20 mL of pure water were added and the mixture was stirred at 35°C for 10 hours. The reaction solution was extracted with chloroform, and the resulting organic layer was concentrated. After that, acetone was added to cause crystallization, yielding 1.60 g of a pale yellow solid (A-3q). 1.48 g (3.00 mmol) of compound (A-3q), 0.30 g (3.30 mmol) of aminoacetonitrile hydrochloride, and 30 mL of N,N-dimethylformamide were added to a 200 mL three-neck flask, and the mixture was stirred at 110°C for 9 hours. Pure water was then added to the reaction solution to cause crystallization, yielding a gray solid. The resulting gray solid was recrystallized using acetone, yielding 1.15 g of the target white solid (A-3). The resulting compound (A-3) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 8.99 (d, J = 7.6 Hz, 1H), 8.89 (d, J = 7.6 Hz, 1H), 4.88-5.03 (m, 2H), 2.22-2.45 (m, 2H), 1.94-2.08 (m, 2H), 1.74-1.87 (m, 2H), 1.55-1.71 (m, 10H), 0.86-1.48 (m, 12H)

[0165] (Synthesis Example 8: Synthesis of compound (A-320))

[0166]

[0167] To a 200 mL three-neck flask, 2.68 g (10.0 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 2.54 g (20.0 mmol) of cyclooctylamine, 0.68 g (10.0 mmol) of imidazole, and 50 mL of N,N-dimethylformamide were added and stirred at 120°C for 12 hours. Then, 10 mL of ethanol was added to the reaction solution and the mixture was filtered. The resulting solid was dried, yielding 4.08 g of a white solid (A-320p). To a 300 mL three-neck flask, 2.43 g (5.0 mmol) of compound (A-320p), 0.11 g (0.50 mmol) of ruthenium trichloride hydrate, 8.55 g (40 mmol) of sodium periodate, 20 mL of dichloromethane, 20 mL of acetonitrile, and 20 mL of pure water were added and the mixture was stirred at 35°C for 10 hours. The reaction solution was extracted with chloroform, and the resulting organic layer was concentrated. After that, acetone was added to cause crystallization, yielding 1.82 g of a pale yellow solid (A-320q). 1.48 g (3.00 mmol) of compound (A-320q), 0.30 g (3.30 mmol) of aminoacetonitrile hydrochloride, and 30 mL of N,N-dimethylformamide were added to a 200 mL three-neck flask, and the mixture was stirred at 110°C for 9 hours. Pure water was then added to the reaction solution to cause crystallization, yielding a gray solid. The resulting gray solid was recrystallized using acetone, yielding 0.94 g of the target white solid (A-320). The resulting compound (A-320) was identified as follows: １ H-NMR was used. １ H-NMR (CDCl ３ ) δ (ppm): 8.97 (d, J = 7.6Hz, 1H), 8.88 (d, J = 7.6Hz, 1H), 5.25-5.37 (m, 2H), 2.42-2.59 (m, 4H), 1.53-1.93 (m, 24H)

[0168] [Compounds used in evaluation]

[0169] <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.

[0170] (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.

[0171] (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 (A-12) was formed to prepare a hole transport promotion layer.

[0172] (Fabrication of Second Electrode) A 80 nm thick Au film was formed to fabricate a second electrode.

[0173] (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.

[0174] [Element Example 2] Photoelectric conversion element 2 of element example 2 was prepared in the same manner as element example 1, except that compound (A-3) was used (an example in which cyclohexylethyl was used) instead of compound (A-12) in the preparation of the hole transport promotion layer, and was evaluated in the same manner as element example 1. The results are shown in Table 1.

[0175] [Element Example 3] Photoelectric conversion element 3 of element example 3 was prepared in the same manner as element example 1, except that compound (A-320) was used (an example using cyclooctyl) instead of compound (A-12) in the preparation of the hole transport promotion layer, and was evaluated in the same manner as element example 1. The results are shown in Table 1.

[0176] [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.

[0177] [Comparative Element Example 2] Photoelectric conversion element 1 of Comparative Element Example 2 was prepared in the same manner as in Example Element 1, except that the following compound (NTP) was used instead of Compound (A-12) in the preparation of the hole transport promotion layer, and was evaluated in the same manner as in Example Element 1. The results are shown in Table 1.

[0178]

[0179] A hole-only device was produced in the same manner as in Element Example 1, except that the following compound (D1) was used instead of compound (A-12) in the preparation of the hole transport promotion layer. The hole transport ability of the obtained hole-only device was evaluated in the same manner as in Element Example 1. The results are shown in Table 1.

[0180]

[0181]

[0182] The element of Device Example 1 using Compound (A-12) as a hole transport promoting material, the element of Device Example 2 using Compound (A-3), and the element of Device Example 3 using Compound (A-320) showed a lower HOD voltage than the element of Device Comparative Example 1 using no hole transport promoting material, and the element of Device Comparative Example 2 using the known material NPT. Furthermore, the element of Device Example 1 using Compound (A-12) as a hole transport promoting material, the element of Device Example 2 using Compound (A-3), and the element of Device Example 3 using Compound (A-320) were able to improve the evaluation results of the HOD voltage compared to Device Reference Example 1 using Compound (D1).

[0183] <Preparation and Evaluation of Photoelectric Conversion Element> [Element Example 4] 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.

[0184] (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 (A-12) 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.

[0185] From the above, the area is 4 mm ２ A photoelectric conversion element 1 shown in FIG. 1 was fabricated. A voltage of 2.5 V (absolute value) was applied to the photoelectric conversion element fabricated as described above so that electrons were transported to the second electrode 16 side and holes were transported to the first electrode 11 side. The current in the dark (dark current, mA / cm ２ The dark current was measured using a Keithley Source Measure Unit 2636B. The external quantum efficiency was measured using a solar cell spectral response measurement device (Soma Optical Co., Ltd.). The wavelength of the irradiated light was 560 nm, and the intensity was 50 μW / cm. ２ The measurements were carried out at 100°C. The results are shown in Table 2. The dark current and external quantum efficiency are relative values, with the result of Comparative Example 3 of the device described below being set as the reference value (100). The lower the dark current value, the better the performance, and the higher the external quantum efficiency value, the better the performance.

[0186] [Element Example 5] Photoelectric conversion element 5 of element example 5 was prepared in the same manner as element example 4, except that compound (A-3) was used instead of compound (A-12) 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 element example 4. The results are shown in Table 2.

[0187] [Element Example 6] Photoelectric conversion element 6 of Element Example 6 was prepared in the same manner as in Element Example 4, except that compound (A-320) was used instead of compound (A-12) 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 4. The results are shown in Table 2.

[0188] [Element Comparative Example 3] A photoelectric conversion element 1 of Element Comparative Example 3 was prepared in the same manner as in Element Example 4, except that the compound (NTP) was used instead of compound (A-12) 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.

[0189] [Element Comparative Example 4] A photoelectric conversion element of Element Comparative Example 4 was prepared in the same manner as in Element Example 4, 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 4. The results are shown in Table 2. In Element Comparative Example 4, the dark current was too large to measure the external quantum efficiency.

[0190] Photoelectric conversion element 1 of Reference Example Element 2 was prepared in the same manner as in Example Element 4, except that compound (D1) was used instead of compound (A-12) in the preparation of the hole transport promotion layer 12, and the dark current and external quantum efficiency were measured in the same manner as in Example Element 4. The results are shown in Table 2.

[0191]

[0192] As shown in Table 2, in the elements of Element Examples 4 to 6 using the photoelectric conversion element material 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 Examples 3 and 4. As shown in Table 2, in the elements of Element Examples 4 to 6 using the photoelectric conversion element material for an imaging element of the present invention, the evaluation results of dark current and external quantum efficiency were improved compared to the element of Element Reference Example 2.

[0193] The organic electronic device of the present invention contains a compound represented by formula (1) to improve hole transport capability, and when used in a photoelectric conversion device, photoelectric conversion can be performed more efficiently. Furthermore, the organic electronic device of the present invention contains a compound represented by formula (1), which suppresses dark current, and is expected to reduce noise when used in a photoelectric conversion device such as an imaging device. Furthermore, the organic electronic device of the present invention contains a compound represented by formula (1), which can have high external quantum efficiency and can convert light into current without loss, and is expected to achieve high sensitivity when used in a photoelectric conversion device, for example.

[0194] 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 a hole transport region disposed between the first electrode and the second electrode, wherein the hole transport region comprises a hole transport layer and a hole transport promoting layer containing a compound represented by the following formula (1), or an organic electronic device comprising a layer comprising a mixture of a hole transport material and a compound represented by the following formula (1): (In formula (1), X １ , X ２ , X ３ and X ４ each independently represents a nitrogen atom or C—R. １ ~X ４ At least one of the groups is a nitrogen atom. R represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. R ａ and R ｂ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms.

2. X １ ~X ４ Among them, X is a nitrogen atom １ ~X ４ The organic electronic device according to claim 1 , wherein the number of 3. X １ ~X ４ Among them, X is a nitrogen atom １ ~X ４ The organic electronic device according to claim 2 , wherein the number of 4. X １ ~X ４ Of these, X １ is a nitrogen atom, or X １ and X ３ The organic electronic device according to claim 3 , wherein is a nitrogen atom.

5. R is a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, a cyanomethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a carboxy group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a fluoropyrimidyl group, a trifluoromethylpyrimidyl group, a triazyl group, a cyanotriazyl group, a fluorotriazyl group, a trifluoromethyltriazyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, 5. The organic electronic device according to claim 4, wherein the alkyl group is a methoxy group, an ethoxy group, a perfluoroethoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a phenoxy group, a cyanophenoxy group, a pyridyloxy group, a quinolyloxy group, a methoxycarbonyl group, or an ethoxycarbonyl group.

6. The organic electronic device according to claim 5, wherein R is a hydrogen atom, cyano group, fluoro group, trifluoromethyl group, cyclohexylmethyl group, cyclohexylethyl group, methylpropyl group, ethylpropyl group, methylbutyl group, hexyl group, cyanomethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, phenyl group, cyanophenyl group, fluorophenyl group, trifluoromethylphenyl group, pyridyl group, cyanopyridyl group, fluoropyridyl group, trifluoromethylpyridyl group, pyrimidyl group, cyanopyrimidyl group, fluoropyrimidyl group, trifluoromethylpyrimidyl group, perfluoroethoxy group, perfluoropropoxy group, perfluorobutoxy group, phenoxy group, cyanophenoxy group, or pyridyloxy group.

7. The organic electronic device according to claim 6, wherein R is a hydrogen atom, a cyano group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, or a trifluoromethylpyridyl group.

8. R ａ and R ｂ each independently represents a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a fluoronaphthyl group, a trifluoromethylnaphthyl group, 7. The organic electronic device according to claim 6, wherein the aryl group is a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, a benzimidazolyl group, or a cyanobenzimidazolyl group.

9. R ａ and R ｂ wherein each independently represents a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, a fluoronaphthyl group, a trifluoromethylnaphthyl group, a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, or a trifluoromethylimidazolyl group.

10. R ａ and R ｂ wherein each independently represents a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a cyanothiazolyl group, an imidazolyl group, or a cyanoimidazolyl group.

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

12. The organic electronic device according to claim 11, wherein the light-receiving layer is a layer containing at least two organic components.

13. A compound represented by the following formula (2) or (3): (In formula (2) and formula (3), R １ represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, a substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. R ｃ , R ｄ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms, provided that R ｃ , R ｄ is an unsubstituted or fluorine-substituted linear alkyl group having 1 to 10 carbon atoms, a cyclohexyl group, or a fluorine-substituted aryl group, R １ is a substituent other than a hydrogen atom or a phenyl group. ２ , R ３ , R ４ , and R ５ R each independently represents a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, an optionally substituted heteroaryl group having 3 to 17 carbon atoms, an optionally substituted alkoxy group having 1 to 18 carbon atoms, an optionally substituted aryloxy group having 6 to 18 carbon atoms, an optionally substituted heteroaryloxy group having 3 to 17 carbon atoms, an optionally substituted alkoxycarbonyl group having 1 to 18 carbon atoms, an optionally substituted aryloxycarbonyl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryloxycarbonyl group having 3 to 17 carbon atoms. ｅ , and R ｆ each independently represents an optionally substituted alkyl group having 1 to 18 carbon atoms, an optionally substituted aryl group having 6 to 18 carbon atoms, or an optionally substituted heteroaryl group having 3 to 17 carbon atoms, provided that R ｅ , R ｆ When is a cyclohexyl group, R ４ and R ５ is a substituent other than a hydrogen atom.) 14. R １ ~R ５ are each independently a hydrogen atom, a cyano group, a fluoro group, a trifluoromethyl group, a carboxy group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a pyrimidyl group, a cyanopyrimidyl group, a triazyl group, a cyanotriazyl group, a quinolyl group, a cyanoquinolyl group, a phenoxy group, a cyanophenoxy group, a pyridyloxy group, a quinolyloxy group, a methoxycarbonyl group, or an ethoxycarbonyl group.

15. R １ ~R ５ The compound according to claim 14 , wherein each independently represents a hydrogen atom, a cyano group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, or a cyanoquinolyl group.

16. R ｃ , R ｄ , R ｅ , and R ｆ each independently represents a methyl group, a cyclohexylmethyl group, an ethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a heptyl group, a cycloheptyl group, an octyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a diamantyl group, a diamantylmethyl group, a diamantylethyl group, a cyanomethyl group, a cyanoethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a naphthyl group, a cyanonaphthyl group, 16. The compound according to claim 15, which is a pyridyl group, a cyanopyridyl group, a fluoropyridyl group, a trifluoromethylpyridyl group, a quinolyl group, a cyanoquinolyl group, a fluoroquinolyl group, a trifluoromethylquinolyl group, a thiazolyl group, a cyanothiazolyl group, a fluorothiazolyl group, a trifluoromethylthiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a fluorooxazolyl group, a trifluoromethyloxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a fluoroimidazolyl group, a trifluoromethylimidazolyl group, a benzimidazolyl group, or a cyanobenzimidazolyl group.

17. R ｃ , R ｄ , R ｅ , and R ｆ each independently represents a cyclohexylmethyl group, a methylethyl group, a cyclohexylethyl group, a propyl group, a methylpropyl group, an ethylpropyl group, a butyl group, a methylbutyl group, a pentyl group, a methylpentyl group, an ethylpentyl group, a hexyl group, a methylhexyl group, an ethylhexyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, 17. The compound of claim 16, which is a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a thiazolyl group, a cyanothiazolyl group, a benzothiazolyl group, a cyanobenzothiazolyl group, an oxazolyl group, a cyanooxazolyl group, a benzoxazolyl group, a cyanobenzoxazolyl group, an imidazolyl group, a cyanoimidazolyl group, a benzimidazolyl group, or a cyanobenzimidazolyl group.

18. R ｃ , R ｄ , R ｅ , and R ｆ are each independently a cyclohexylmethyl group, a cyclohexylethyl group, a cycloheptyl group, a cyclooctyl group, an adamantylmethyl group, an adamantylethyl group, a cyanomethyl group, a cyanoethyl group, a phenyl group, a cyanophenyl group, a naphthyl group, a cyanonaphthyl group, a pyridyl group, a cyanopyridyl group, a quinolyl group, a cyanoquinolyl group, a thiazolyl group, a cyanothiazolyl group, an imidazolyl group, a cyanoimidazolyl group, or a benzimidazolyl group.

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