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

Abstract

Provided are an organic electronic element with which it is possible to achieve improved hole transport capacity, a material for an organic electronic element, and an imide compound for use in the organic electronic element, with which it is possible to achieve improved hole transport capacity.　This organic electronic element comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer containing a compound with a partial structure represented by formula (Q). (In the formula (Q), * represents a bond, the bond constituting a partial structure of an annular imide structure; R1 represents an aliphatic hydrocarbon group having 1-15 carbon atoms, wherein the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6-20 carbon atoms, a heteroaromatic group having 3-20 carbon atoms, and an aliphatic hydrocarbon group having 1-15 carbon atoms, and the aliphatic hydrocarbon group may be linear, branched, or cyclic; and n represents 1, 2, or 3.)

Description

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

[0001] The present invention relates to an imide compound having an imide skeleton as a partial structure, a material for an organic electronic device containing the compound, and an organic electronic device.

[0002] Currently, active efforts are being made to create new, highly functional devices using organic materials. Research and development is particularly active on organic electronic devices, such as photoelectric conversion devices and organic electroluminescence (EL) devices, with advances being made in material and device design aimed at improving device performance. For example, in photoelectric conversion devices used for video recording, a problem exists in that slow transport of carriers (electrons and holes) generated in the light-receiving layer to the electrode can cause image retention. In organic EL devices, slow transport of carriers from the electrode to the light-emitting layer can increase the driving voltage. Therefore, highly efficient carrier movement within the device is required to achieve high device performance.

[0003] Incidentally, imide compounds have been disclosed as compounds for use as electron transport materials in electrophotographic photoreceptors (see Patent Document 1). However, further improvements in performance are required in the field of organic electronic devices, and therefore further improvements are necessary.

[0004] JP 2019-182789 A

[0005] An object of the present invention is to provide an organic electronic element capable of improving the hole transport capability, a material for an organic electronic element, and an imide compound for use in the organic electronic element capable of improving the hole transport capability.

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

[0007] That is, the present invention includes the following aspects: [1] An organic electronic device including a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a partial structure represented by the following formula (Q): (In formula (Q), * represents a bond, and the bond constitutes a partial structure of a cyclic imide structure. R １ represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, which may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, which aliphatic hydrocarbon group may be linear, branched, or cyclic, and n represents 1, 2, or 3. [2] An organic electronic device comprising a first electrode, a second electrode, and an organic layer and a light-receiving layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having the partial structure represented by formula (Q). [3] The organic electronic device according to [2], wherein the light-receiving layer is a layer containing at least two organic components. [4] The organic electronic device according to any one of [1] to [3], wherein the organic layer comprises a hole transport layer and a hole transport promoting layer containing a compound having the partial structure represented by formula (Q), or comprises a layer formed by mixing a hole transport material with a compound having the partial structure represented by formula (Q). [5] The organic electronic device according to [4], wherein the hole transport layer and the hole transport promoting layer are disposed adjacent to each other between the first electrode and the second electrode. [6] The organic electronic device according to [4], wherein R in formula (Q) １is a methylene group or an ethylene group, and the methylene group and the ethylene group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. [7] The organic electronic device according to any one of [1] to [5], １ [8] The organic electronic device according to any one of [1] to [7], wherein the compound having a partial structure represented by formula (Q) is a compound represented by the following formula (1): (In formula (1), R ２ and R ３each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group being optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and m and n each independently represent 1, 2, or 3. ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms, the aromatic hydrocarbon ring and the heteroaromatic ring may each be a monocycle, a condensed ring, or a linked ring, and the linked ring may be bonded to a methylene group substituted with a trifluoromethyl group, the aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms, the aromatic hydrocarbon ring and the heteroaromatic ring may be bonded to the aromatic hydrocarbon group or the heteroaromatic group by one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group, The aromatic hydrocarbon group and the heteroaromatic group may each be a monocyclic ring, a fused ring, or a linked ring.) [9] The organic electronic device according to [8], wherein the ring A in the formula (1) is any one of the following (A-1) to (A-17) optionally substituted with one or more groups:

[10] R in the formula (1) ２ and R ３are each independently a methylene group or an ethylene group, and the methylene group and the ethylene group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

[11] The organic electronic device according to [8] or [9], ２ and R ３

[12] A material for an organic electronic device, comprising a compound represented by the following formula (2): (In formula (2), R ４ and R ５each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group being optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and m and n each independently represent 1, 2, or 3. ring B represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms, the aromatic hydrocarbon ring and the heteroaromatic ring may each be a monocycle, a condensed ring, or a linked ring, and the linked ring may be bonded to a methylene group substituted with a trifluoromethyl group, the aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms, the aromatic hydrocarbon ring and the heteroaromatic ring may be bonded to the aromatic hydrocarbon group or the heteroaromatic group by one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group, The aromatic hydrocarbon group and the heteroaromatic group may each be a single ring, a fused ring, or a linked ring.

[13] The material for an organic electronic device according to

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

[14] The material for an organic electronic device according to

[12] , which is a material for an imaging photoelectric conversion device.

[15] R in the formula (2) ４ and R ５are each independently a methylene group or an ethylene group, and the methylene group and the ethylene group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

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

[12] to

[14] , ４ and R ５

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

[12] to

[16] , wherein the ring B in the formula (2) is any one of the following (B-1) to (B-17) optionally substituted with one or more groups:

[18] An imide compound represented by the following formula (3) or (4): (In formula (3), T １ and T ２ R each independently represents a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. ６ and R ７each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and m and n each independently represent 1, 2, or 3. In formula (4), T ３ ~T ６ R each independently represents a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. ８ and R ９ each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and m and n each independently represent 1, 2, or 3. However, T ３ =T ４ =T ５ =T ６ = hydrogen atom, and when m = n = 1, R ８ =R ９ = not an unsubstituted methylene group, T ３ =T ４ =T ５ =T ６ = hydrogen atom, and when m = n = 1, R ８ =R ９= not a methylene group substituted with an isobutyl group, T ３ =T ４ =T ５ =T ６ = hydrogen atom, and when m = n = 1, R ８ =R ９ = not an unsubstituted ethylene group.)

[19] R in the formula (3) or (4) ６ ~R ９ are each independently a methylene group or an ethylene group, and the methylene group and the ethylene group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

[20] The imide compound according to

[18] , ６ ~R ９

[21] The imide compound according to

[18] , wherein R in the formula (3) or (4) is independently an unsubstituted methylene group or an unsubstituted ethylene group. ６ ~R ９ are each independently a methylene group substituted with a phenyl group, a cyanophenyl group, or a pyridyl group.

[0008] According to the present invention, it is possible to provide an organic electronic element capable of improving the hole transport capability, a material for an organic electronic element, and an imide compound for use in the organic electronic element capable of improving the hole transport capability.

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

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

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

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

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

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

[0015] The photoelectric conversion element according to the present invention may have, for example, a first electrode, a hole transport promoting layer, a hole transport layer, and a second electrode laminated in this order, or a first electrode, a layer formed by mixing a hole transport material forming the hole transport layer with the compound represented by formula (Q), 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 comprises 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 comprises 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 other layers 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 Device> The organic EL device according to the present invention includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer including a hole transport region. The hole transport region refers to the region between the first electrode and the light-emitting layer, and includes, for example, a hole transport layer and a hole injection layer. In the present invention, the compound represented by the above formula (Q) 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 device may include other layers. Examples of the other layers include layers commonly used in organic EL devices. 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 (Q), 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 of the present invention comprises a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, and a second electrode stacked in this order. In another embodiment, the organic EL device of the present invention comprises a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a second electrode stacked in this order. The layers may be stacked adjacent to each other, or other layers 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 (Q) in the organic electronic device of the present invention will be described.

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

[0025]

[0026] In formula (Q), * represents a bond and constitutes a partial structure of a cyclic imide structure. １ represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. Furthermore, the aliphatic hydrocarbon group may be a group in which a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group are combined. Examples of saturated aliphatic hydrocarbon groups include alkylene groups having 1 to 15 carbon atoms. In this specification, the term "alkylene group" refers to a divalent group generated by the loss of two hydrogen atoms from an aliphatic hydrocarbon (alkane) such as methane, ethane, or propane, and is generally -C ｘ H ２ｘ- (where x is a positive integer). Examples of unsaturated aliphatic hydrocarbon groups include alkenylene groups having 2 to 15 carbon atoms and alkynylene groups having 2 to 15 carbon atoms. The unsaturated aliphatic hydrocarbon group may have two or more carbon-carbon double bonds, may have two or more carbon-carbon triple bonds, or may have both a carbon-carbon double bond and a carbon-carbon triple bond. In this specification, the term "alkenylene group" refers to a divalent group generated by the loss of two hydrogen atoms from an aliphatic hydrocarbon having one carbon-carbon double bond in the molecule, such as ethylene, and is generally represented by -C ｘ H ２ｘ－２ In this specification, the term "alkynylene group" refers to a divalent group generated by the loss of two hydrogen atoms from an aliphatic hydrocarbon having one carbon-carbon triple bond in the molecule, such as acetylene, and is generally represented by -C ｘ H ２ｘ－４ - (where x is an integer of 2 or greater).

[0027] Examples of alkylene groups having 1 to 15 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, adamantylene, tert-butylene, and isopropylene. Examples of alkenylene groups having 2 to 15 carbon atoms include ethenylene (-CH=CH-), propenylene (-CH ２ CH═CH—), butenylene group (—CH ２ CH=CHCH ２ Here, "=" represents a carbon-carbon double bond. Examples of the alkynylene group having 2 to 15 carbon atoms include an ethynylene group (-C≡C-), a propynylene group (-CH ２ C≡C-), butynylene group (-CH ２ C≡CCH ２-), etc. Here, "≡" represents a carbon-carbon triple bond. As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred in that the compound is stable, a methylene group or an ethylene group is more preferred in that synthesis is easy, and a methylene group is even more preferred in that device performance is excellent.

[0028] The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched, or cyclic. n represents 1, 2, or 3. As n, 1 or 2 is preferred in terms of ease of synthesis, and 1 is more preferred in terms of the stability of the compound.

[0029] Examples of aromatic hydrocarbon groups having 6 to 20 carbon atoms include phenyl, naphthyl, anthryl, phenanthrenyl, pyrenyl, perylenyl, triphenylenyl, tetracenyl, chrysenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, biphenylyl, terphenyl, naphthylphenyl, phenylnaphthyl, binaphthyl, anthrylphenyl, phenylanthryl, naphthylanthryl, etc. As aromatic hydrocarbon groups having 6 to 20 carbon atoms, phenyl or naphthyl groups are preferred in terms of excellent device performance.

[0030] Examples of heteroaromatic groups having 3 to 20 carbon atoms include pyridyl, pyrazyl, pyrimidyl, triazyl, quinolyl, isoquinolyl, quinoxalyl, quinazolinyl, pyridopyrimidinyl, benzoquinolyl, benzoisoquinolyl, phenanthrolyl, phenanthridyl, acridyl, phenazinyl, phenoxazinyl, phenothiazinyl, benzoquinoxalyl, hexaazatriphenylenyl, thienyl, furyl, benzothienyl, benzofuryl, isobenzofuryl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, pyrrole, indole, isoindole, indolizinyl, purine, imidazolyl, carbazolyl, thiazolyl, and thiadiazolyl groups. As the heteroaromatic group having 3 to 20 carbon atoms, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, or an isoquinolyl group is preferred in terms of excellent device performance, and a pyridyl group or a pyrazyl group is more preferred in terms of ease of synthesis.

[0031] -R in formula (Q) １ - (CN) ｎ As examples of the aryl group, the following (R-1) to (R-56) can be mentioned as preferred examples.

[0032]

[0033]

[0034] Among the above (R-1) to (R-56), (R-1), (R-2), (R-8) and (R-26) are more preferred examples, and (R-1), (R-8) and (R-26) are even more preferred examples, with (R-1) and (R-26) being particularly preferred in terms of ease of synthesis. １is preferably an unsubstituted methylene group, a methylene group substituted with a cyano group, an aromatic hydrocarbon group, a heteroaromatic group or an aliphatic hydrocarbon group, or an unsubstituted ethylene group, more preferably an unsubstituted methylene group, a methylene group substituted with a cyano group, a methylene group substituted with a phenyl group, a methylene group substituted with a cyanophenyl group, a methylene group substituted with a pyridyl group, or an unsubstituted ethylene group, and from the viewpoint of ease of synthesis, an unsubstituted methylene group, an unsubstituted ethylene group, or a methylene group substituted with a phenyl group is even more preferred.

[0035] The organic electronic element of the present invention is not particularly limited, but may be an organic EL element or 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.

[0036] The compound represented by formula (Q) is used as a part of an organic electronic device. The part of the organic electronic device is not particularly limited, but examples thereof include an electron transport layer, an emitting layer, a light receiving layer, a hole injection layer, and a hole transport promoting layer. Among these, the compound represented by formula (Q) is preferably used in the hole transport promoting layer.

[0037] An example of the compound represented by formula (Q) is a compound represented by the following formula (1).

[0038]

[0039] In formula (1), R ２ and R ３each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group in formula (1) is the same as the aliphatic hydrocarbon group in formula (Q) described above. As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred in terms of the stability of the compound, a methylene group or an ethylene group is more preferred in terms of ease of synthesis, and a methylene group is even more preferred in terms of excellent device performance. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched, or cyclic. In formula (1), m represents 1, 2, or 3. m is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (1), n ​​represents 1, 2, or 3. n is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (1), ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms. The aromatic hydrocarbon ring having 6 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring. The heteroaromatic ring having 4 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring. The linked ring may be bonded by a methylene group substituted with a trifluoromethyl group. The fused ring may be a fused ring between aromatic hydrocarbon rings, a fused ring between an aromatic hydrocarbon ring and a heteroaromatic ring, or a fused ring between heteroaromatic rings. The connecting ring may be a connecting ring between aromatic hydrocarbon rings, a connecting ring between an aromatic hydrocarbon ring and a heteroaromatic ring, or a connecting ring between heteroaromatic rings.

[0040] Examples of aromatic hydrocarbon rings having 6 to 20 carbon atoms include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, a triphenylene ring, a tetracene ring, a chrysene ring, a fluorene ring, a 9,9-dimethylfluorene ring, a 9,9-diphenylfluorene ring, a spirobifluorene ring, a biphenyl ring, and a terphenyl ring. As aromatic hydrocarbon rings having 6 to 20 carbon atoms, a benzene ring, a naphthyl ring, and a perylene ring are preferred in terms of ease of synthesis, and a benzene ring and a naphthalene ring are more preferred in terms of excellent device performance.

[0041] Examples of heteroaromatic rings having 4 to 20 carbon atoms include a pyridine ring, a pyrazine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a benzoquinoline ring, a benzoisoquinoline ring, a phenanthroline ring, a phenanthridine ring, an acridine ring, a phenazine ring, a phenoxazine ring, a phenothiazine ring, a benzoquinoxaline ring, a thienyl ring, a furyl ring, a benzothiophene ring, a benzofuran ring, an isobenzofuran ring, a dibenzothiophene ring, a dibenzofuran ring, a benzoxazole ring, a pyrrole ring, an indole ring, an isoindole ring, a carbazolyl ring, etc. As heteroaromatic rings having 4 to 20 carbon atoms, a pyridine ring and a pyrazine ring are preferred in terms of excellent device performance.

[0042] The aromatic hydrocarbon ring having 6 to 20 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon ring having 6 to 20 carbon atoms may be bonded to the aromatic hydrocarbon group having 6 to 20 carbon atoms or the heteroaromatic group having 3 to 20 carbon atoms via one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0043] The heteroaromatic ring having 4 to 20 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. The heteroaromatic ring having 4 to 20 carbon atoms may be bonded to the aromatic hydrocarbon group having 6 to 20 carbon atoms or the heteroaromatic group having 3 to 20 carbon atoms via one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0044] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include the same aromatic hydrocarbon groups as the aromatic hydrocarbon group having 6 to 20 carbon atoms in the compound represented by the above formula (Q). The aromatic hydrocarbon group having 6 to 20 carbon atoms may be a monocyclic ring, a condensed ring, or a linked ring.

[0045] Examples of the heteroaromatic group having 3 to 20 carbon atoms include the same heteroaromatic group having 3 to 20 carbon atoms as the heteroaromatic group having 3 to 20 carbon atoms in the compound represented by the above formula (Q). The heteroaromatic group having 3 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring.

[0046] Examples of the fluoroalkyl group having 1 to 10 carbon atoms include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a difluoroethyl group, a trifluoroethyl group, a tetrafluoroethyl group, a perfluoroethyl group, a fluoropropyl group, a perfluoropropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, and a perfluorooctyl group.

[0047] Examples of the fluoroalkoxy group having 1 to 10 carbon atoms include a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a fluoroethoxy group, a difluoroethoxy group, a trifluoroethoxy group, a tetrafluoroethoxy group, a perfluoroethoxy group, a fluoropropoxy group, a perfluoropropoxy group, a perfluorobutoxy group, a perfluoropentyloxy group, a perfluorohexyloxy group, a perfluoroheptyloxy group, and a perfluorooctyloxy group.

[0048] Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

[0049] -R in formula (1) ２ - (CN) ｍ and -R ３ - (CN) ｎ As for R in formula (1), the above-mentioned (R-1) to (R-45) are preferably mentioned as examples. Among these, (R-1), (R-2) and (R-8) are more preferable, and (R-1) and (R-8) are even more preferable in terms of ease of synthesis. ２ and R ３ are each independently preferably an unsubstituted methylene group, a methylene group substituted with a cyano group, or an unsubstituted ethylene group, and are more preferably an unsubstituted methylene group or an unsubstituted ethylene group in terms of ease of synthesis.

[0050] Examples of ring A in formula (1) include the following (A-1) to (A-17). These (A-1) to (A-17) may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. Furthermore, these (A-1) to (A-17) may be bonded to the aromatic hydrocarbon group having 6 to 20 carbon atoms or the heteroaromatic group having 3 to 20 carbon atoms via one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0051]

[0052] Of the above (A-1) to (A-17), (A-1), (A-2), (A-4), (A-5), (A-6), (A-8), (A-9), and (A-10) are preferred, with (A-1), (A-2), (A-8), (A-9), and (A-10) being more preferred in terms of having sufficient acceptor properties and expected performance. Furthermore, (A-1) and (A-2) are preferred in terms of ease of synthesis, and (A-1) is more preferred in terms of ease of raw material availability.

[0053] The compound represented by formula (Q) may be used as a material for an organic electronic device. Examples of the material for an organic electronic device include a material containing a compound represented by the following formula (2):

[0054]

[0055] In formula (2), R ４ and R ５each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group in formula (2) is the same as the aliphatic hydrocarbon group in formula (Q) described above. As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred in terms of the stability of the compound, a methylene group or an ethylene group is more preferred in terms of ease of synthesis, and a methylene group is even more preferred in terms of excellent device performance. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched, or cyclic. In formula (2), m represents 1, 2, or 3. m is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (2), n represents 1, 2, or 3. n is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (2), ring B represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a heteroaromatic ring having 4 to 20 carbon atoms. The aromatic hydrocarbon ring having 6 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring. The heteroaromatic ring having 4 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring. The linked rings may be bonded via a methylene group substituted with a trifluoromethyl group.

[0056] Examples of the aromatic hydrocarbon ring having 6 to 20 carbon atoms include aromatic hydrocarbon rings similar to the aromatic hydrocarbon ring having 6 to 20 carbon atoms in the compound represented by formula (1) above. The aromatic hydrocarbon ring having 6 to 20 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. The aromatic hydrocarbon ring having 6 to 20 carbon atoms may be bonded to the aromatic hydrocarbon group having 6 to 20 carbon atoms or the heteroaromatic group having 3 to 20 carbon atoms via one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0057] Examples of the heteroaromatic ring having 4 to 20 carbon atoms include heteroaromatic rings similar to the heteroaromatic ring having 4 to 20 carbon atoms in the compound represented by formula (1) above. The heteroaromatic ring having 4 to 20 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. The heteroaromatic ring having 4 to 20 carbon atoms may be bonded to the aromatic hydrocarbon group having 6 to 20 carbon atoms or the heteroaromatic group having 3 to 20 carbon atoms via one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0058] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include the same aromatic hydrocarbon groups as the aromatic hydrocarbon group having 6 to 20 carbon atoms in the compound represented by the above formula (Q). The aromatic hydrocarbon group having 6 to 20 carbon atoms may be a monocyclic ring, a condensed ring, or a linked ring.

[0059] Examples of the heteroaromatic group having 3 to 20 carbon atoms include the same heteroaromatic group having 3 to 20 carbon atoms as the heteroaromatic group having 3 to 20 carbon atoms in the compound represented by the above formula (Q). The heteroaromatic group having 3 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring.

[0060] Examples of the fluoroalkyl group having 1 to 10 carbon atoms include the same fluoroalkyl groups as the fluoroalkyl groups having 2 to 10 carbon atoms in the compound represented by the above formula (1).

[0061] Examples of the fluoroalkoxy group having 1 to 10 carbon atoms include the same fluoroalkoxy groups as the fluoroalkoxy groups having 1 to 10 carbon atoms in the compound represented by the above formula (1).

[0062] Examples of the alkyl group having 1 to 10 carbon atoms include the same alkyl groups as those having 1 to 10 carbon atoms in the compound represented by the above formula (1).

[0063] -R in formula (2) ４ - (CN) ｍ and -R ５ - (CN) ｎ As for R, the above (R-1) to (R-56) are each independently preferred. Among these, (R-1), (R-2), (R-8) and (R-26) are more preferred, (R-1), (R-8) and (R-26) are even more preferred, and (R-1) and (R-26) are particularly preferred from the viewpoint of ease of synthesis. ４ and R ５ are each independently preferably an unsubstituted methylene group, a methylene group substituted with a cyano group, an aromatic hydrocarbon group, a heteroaromatic group, or an aliphatic hydrocarbon group, or an unsubstituted ethylene group; more preferably an unsubstituted methylene group, a methylene group substituted with a cyano group, a methylene group substituted with a phenyl group, a methylene group substituted with a cyanophenyl group, a methylene group substituted with a pyridyl group, or an unsubstituted ethylene group; and from the viewpoint of ease of synthesis, an unsubstituted methylene group, an unsubstituted ethylene group, or a methylene group substituted with a phenyl group is even more preferable.

[0064] Examples of ring B in formula (2) include the following (B-1) to (B-17). These (B-1) to (B-17) may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms. Furthermore, these (B-1) to (B-17) may be bonded to the aromatic hydrocarbon group having 6 to 20 carbon atoms or the heteroaromatic group having 3 to 20 carbon atoms via one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group.

[0065]

[0066] Of the above (B-1) to (B-17), (B-1), (B-2), (B-4), (B-5), (B-6), (B-8), (B-9), and (B-10) are preferred, with (B-1), (B-2), (B-8), (B-9), and (B-10) being more preferred in terms of having sufficient acceptor properties and expected performance. Furthermore, (B-1) and (B-2) are preferred in terms of ease of synthesis, and (B-1) is more preferred in terms of easy availability of raw materials.

[0067] The compound represented by formula (2) is used as a material for an organic electronic device. Among these, it is preferably a material for a photoelectric conversion device, and more preferably a material for an imaging photoelectric conversion device. Furthermore, the compound represented by formula (2) is preferably used as a hole transport promoting material in each device. That is, the compound represented by formula (2) is more preferably a hole transport promoting material.

[0068] A more preferred embodiment of the compound represented by the above formula (1) or (2) is a compound represented by the following formula (X-1). In formula (X-1), ring G is selected from the group consisting of the following (G-1), (G-2), (G-8), (G-9), and (G-10), and R １１ , R １２each independently represents a methylene group or an ethylene group which may be substituted with one or more groups selected from the group consisting of a cyano group, an aromatic hydrocarbon group having 6 carbon atoms, a heteroaromatic group (e.g., a pyridyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, etc.), and an aliphatic hydrocarbon group having 1 to 6 carbon atoms (which may be a linear, branched, or cyclic aliphatic hydrocarbon group). )

[0069] Examples of the imide compound capable of improving the hole transport ability and used in the organic electronic device or the material for an organic electronic device of the present invention include imide compounds represented by the following formula (3) or (4):

[0070]

[0071]

[0072] In formula (3), T １ and T ２ represents a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. Here, "a substituent formed by combining two or more of these" refers to, for example, a substituent in which one or more hydrogen atoms of an aromatic hydrocarbon group having 6 to 20 carbon atoms are substituted with a cyano group. In formula (3), R ６ and R ７each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group in formula (3) is the same as the aliphatic hydrocarbon group in formula (Q) described above. As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred in terms of the stability of the compound, a methylene group or an ethylene group is more preferred in terms of ease of synthesis, and a methylene group is even more preferred in terms of excellent device performance. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched, or cyclic. In formula (3), m represents 1, 2, or 3. m is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (3), n represents 1, 2, or 3. n is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound.

[0073] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include the same aromatic hydrocarbon groups as the aromatic hydrocarbon group having 6 to 20 carbon atoms in the compound represented by the above formula (Q). The aromatic hydrocarbon group having 6 to 20 carbon atoms may be a monocyclic ring, a condensed ring, or a linked ring.

[0074] Examples of the heteroaromatic group having 3 to 20 carbon atoms include the same heteroaromatic group having 3 to 20 carbon atoms as the heteroaromatic group having 3 to 20 carbon atoms in the compound represented by the above formula (Q). The heteroaromatic group having 3 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring.

[0075] Examples of the fluoroalkyl group having 1 to 10 carbon atoms include the same fluoroalkyl groups as the fluoroalkyl groups having 2 to 10 carbon atoms in the compound represented by the above formula (1).

[0076] Examples of the fluoroalkoxy group having 1 to 10 carbon atoms include the same fluoroalkoxy groups as the fluoroalkoxy groups having 1 to 10 carbon atoms in the compound represented by the above formula (1).

[0077] Examples of the alkyl group having 1 to 10 carbon atoms include the same alkyl groups as those having 1 to 10 carbon atoms in the compound represented by the above formula (1).

[0078] In formula (4), T ３ ~T ６ each independently represents a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. ８ and R ９each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group in formula (4) is the same as the aliphatic hydrocarbon group in formula (Q) described above. As the aliphatic hydrocarbon group having 1 to 15 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred in terms of the stability of the compound, a methylene group or an ethylene group is more preferred in terms of ease of synthesis, and a methylene group is even more preferred in terms of excellent device performance. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The aliphatic hydrocarbon group having 1 to 15 carbon atoms may be linear, branched, or cyclic. In formula (4), m represents 1, 2, or 3. m is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (4), n represents 1, 2, or 3. n is preferably 1 or 2 in terms of ease of synthesis, and more preferably 1 in terms of the stability of the compound. In formula (4), T ３ =T ４ =T ５ =T ６ = hydrogen atom, and when m = n = 1, R ８ =R ９ = not an unsubstituted methylene group. ３ =T ４ =T ５ =T ６ = hydrogen atom, and when m = n = 1, R ８ =R ９ = a methylene group substituted with an isobutyl group. ３ =T ４ =T ５ =T ６ = hydrogen atom, and when m = n = 1, R ８ =R ９ = Not an unsubstituted ethylene group.

[0079] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include the same aromatic hydrocarbon groups as the aromatic hydrocarbon group having 6 to 20 carbon atoms in the compound represented by the above formula (Q). The aromatic hydrocarbon group having 6 to 20 carbon atoms may be a monocyclic ring, a condensed ring, or a linked ring.

[0080] Examples of the heteroaromatic group having 3 to 20 carbon atoms include the same heteroaromatic group having 3 to 20 carbon atoms as the heteroaromatic group having 3 to 20 carbon atoms in the compound represented by the above formula (Q). The heteroaromatic group having 3 to 20 carbon atoms may be a monocyclic ring, a fused ring, or a linked ring.

[0081] Examples of the fluoroalkyl group having 1 to 10 carbon atoms include the same fluoroalkyl groups as the fluoroalkyl groups having 2 to 10 carbon atoms in the compound represented by the above formula (1).

[0082] Examples of the fluoroalkoxy group having 1 to 10 carbon atoms include the same fluoroalkoxy groups as the fluoroalkoxy groups having 1 to 10 carbon atoms in the compound represented by the above formula (1).

[0083] Examples of the alkyl group having 1 to 10 carbon atoms include the same alkyl groups as those having 1 to 10 carbon atoms in the compound represented by the above formula (1).

[0084] In formula (3) or formula (4), T １ ~T ６ As the groups, a cyano group, a phenyl group which may be substituted, a pyridyl group, a pyrazyl group, a triazyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, a phenyloxy group, a pyridineoxy group, a pyrazineoxy group, a pyrimidinoxy group, and a triazineoxy group are each independently preferred in terms of excellent device performance.

[0085] T １ ~T ６Preferred specific examples of the above are each independently a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a tert-butyl group, an isopropyl group, a phenyl group, a cyanophenyl group, a dicyanophenyl group, a tricyanophenyl group, a methylphenyl group, a dimethylphenyl group, group, trimethylphenyl group, fluorophenyl group, difluorophenyl group, trifluorophenyl group, perfluorophenyl group, biphenyl group, pyridylphenyl group, bispyridylphenyl group, trifluoromethylphenyl group, bistrifluoromethylphenyl group, pyridyl group, cyanopyridyl group, dicyanopyridyl group, tricyanopyridyl group, methylpyridyl group, dimethylpyridyl group, trimethylpyridyl group, fluoropyridyl group, difluoropyridyl group, trifluoropyridyl group, tetrafluoropyridyl group, phenylpyridyl group, diphenylpyridyl group group, bipyridyl group, terpyridyl group, trifluoromethylpyridyl group, bistrifluoromethylpyridyl group, pyrimidyl group, cyanopyrimidyl group, dicyanopyrimidyl group, tricyanopyrimidyl group, methylpyrimidyl group, dimethylpyrimidyl group, trimethylpyrimidyl group, fluoropyrimidyl group, difluoropyrimidyl group, trifluoropyrimidyl group, tetrafluoropyrimidyl group, phenylpyrimidyl group, diphenylpyrimidyl group, pyridylpyrimidyl group, bispyridylpyrimidyl group, trifluoromethylpyrimidyl group, bistrifluoromethylpyrimidyl group a pyrazyl group, a cyanopyrazyl group, a dicyanopyrazyl group, a tricyanopyrazyl group, a methylpyrazyl group, a dimethylpyrazyl group, a trimethylpyrazyl group, a fluoropyrazyl group, a difluoropyrazyl group, a trifluoropyrazyl group, a tetrafluoropyrazyl group, a phenylpyrazyl group, a pyridylpyrazyl group, a trifluoromethylpyrazyl group, a bistrifluoromethylpyrazyl group, a triazyl group, a cyanotriazyl group, a dicyanotriazyl group, a methyltriazyl group, a dimethyltriazyl group, a fluorotriazyl group, a difluorotriazyl group, a phenyltriazyl group,diphenyltriazyl group, pyridyltriazyl group, bispyridyltriazyl group, trifluoromethyltriazyl group, bistrifluoromethyltriazyl group, phenoxy group, biphenyloxy group, cyanophenyloxy group, dicyanophenyloxy group, naphthaleneoxy group, cyanonaphthaleneoxy group, pyridineoxy group, cyanopyridineoxy group, dicyanopyridineoxy group, phenylpyridineoxy group, diphenylpyridineoxy group, pyrazineoxy group, cyanopyrazineoxy group, dicyanopyrazineoxy group, phenylpyrazineoxy group, pyrimidineoxy group, cyanopyrimidineoxy group, dicyanopyrimidinoxy group, quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolinyl group, a pyridopyrimidinyl group, a benzoquinolyl group, a benzoisoquinolyl group, a phenanthrolyl group, a phenanthridyl group, an acridyl group, a phenazinyl group, a phenoxazinyl group, a phenothiazinyl group, a benzoquinoxalyl group, a hexaazatriphenylenyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, an isobenzofuryl group, a dibenzothiophenyl group, a dibenzofuranyl group, a benzoxazolyl group, a pyrrole group, an indole group, an isoindole group, an indolizinyl group, a purine group, an imidazolyl group, a carbazolyl group, a thiazolyl group, a thiadiazolyl group, and the like.

[0086] For example, in formula (3), T １ and T ２ is a hydrogen atom, n and m are 1, and R ６ and R ７ are each independently a methylene group or an ethylene group optionally substituted with one or more groups selected from the group consisting of a cyano group, an aromatic hydrocarbon group having 6 carbon atoms, a heteroaromatic group (e.g., a pyridyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, etc.), and an aliphatic hydrocarbon group having 1 to 6 carbon atoms (which may be a linear, branched, or cyclic aliphatic hydrocarbon group).

[0087] Also, for example, in formula (4), T ３ and T ４ and T ５ and T ６ is a hydrogen atom, n and m are 1, and R ８ and R９ are each independently a methylene group or an ethylene group optionally substituted with one or more groups selected from the group consisting of a cyano group, an aromatic hydrocarbon group having 6 carbon atoms, a heteroaromatic group (e.g., a pyridyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, etc.), and an aliphatic hydrocarbon group having 1 to 6 carbon atoms (which may be a linear, branched, or cyclic aliphatic hydrocarbon group), with the proviso that R ８ and R ９ It is more preferable to exclude cases where both are unsubstituted methylene groups, both are unsubstituted ethylene groups, or both are methylene groups substituted with an isobutyl group.

[0088] Preferred examples of the compound represented by formula (Q) include the following (C-1) to (C-250), however, the compound of the present invention is not limited to these.

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] [Production Method] The compound represented by formula (1) can be synthesized by a known method or a combination thereof. For example, a tetracarboxylic dianhydride represented by formula (5) below is reacted with an amine compound represented by formula (6) below to obtain a compound represented by formula (7) below. The obtained compound represented by formula (7) below is then reacted with an amine compound represented by formula (8) below to synthesize the imide compound represented by formula (1). The imide compound represented by formula (1) can be synthesized in two steps as described above, or in one step.

[0113] (In the formula, R ２ , R ３ , m, n and ring A have the same definitions as in formula (1).

[0114] The reaction conditions in this production method can be similar to those used in general imide-forming reactions (e.g., Electrochemistry Communications 76 (2017) 47-50; Chem. Soc. Rev., 2008, 37, 331-342, etc.). Preferred examples of the reaction solvent include dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), methanol, ethanol, propanol, butanol, water, acetic acid, formic acid, trifluoromethanesulfonic acid, imidazole, and naphthalene, and a mixed solvent of a combination of these solvents may also be used. In addition, a general acid, base, or condensation promoter can also be added as a reaction additive.

[0115] <<Action and Effect of the Compound Represented by Formula (1)>> The compound represented by formula (1) has a pyromellitic diimide skeleton or a specific skeleton structure similar thereto, and therefore this strong acceptor skeleton is expected to have a strong interaction with the HOMO orbital of the hole transport material. In other words, when a layer (e.g., a hole transport promotion layer) in an organic electronic device (e.g., a photoelectric conversion device) contains a compound represented by formula (1), it is expected that the interaction with the HOMO orbital of an adjacent hole transport layer will be enhanced, and carrier exchange between the hole transport layer and the hole transport promotion layer will be promoted. In this way, the compound represented by formula (1) has an extremely deep LUMO level, and therefore it is expected that the exchange of holes between the hole transport layer and the electrode will be smooth. Furthermore, since the compound represented by formula (1) has a pyromellitic diimide skeleton or a specific skeleton structure similar thereto, thermal stability, high reduction resistance, and the like can also be expected. In addition, since the compound represented by formula (1) has a cyano group bonded to the imide skeleton, it is expected to have a strong interaction with the hole transport material, and thus to facilitate smoother exchange of holes between the hole transport layer and the electrode.

[0116] As described above, the present inventors have found that the compound represented by formula (Q) 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 enhanced when the compound represented by formula (Q) (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 (Q), which is the hole transport promoting material of the present invention.

[0117] <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".

[0118] 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.

[0119] <<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.

[0120] 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 on the top surface of the first electrode 11 is omitted in 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.

[0121] [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.

[0122] 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.

[0123] 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.

[0124] [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.

[0125] [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.

[0126] 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.

[0127] [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.

[0128] 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).

[0129] 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, phthalocyanine and its derivatives, etc. 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 can 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, phthalocyanine and its derivatives, (ii) fullerene and its derivatives, other acceptor materials, and (iii) hole-transport materials. The light-receiving layer 14 made of these materials can be formed by vapor deposition of a premixed powder or by co-evaporation in any ratio.

[0130] (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.

[0131] 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).

[0132] [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.

[0133] 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.

[0134] 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.

[0135] [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.

[0136] [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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] <<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 other layers may be added.

[0142] [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).

[0143] [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.

[0144] [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.

[0145] [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 together 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.

[0146] [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.

[0147] [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.

[0148] 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.

[0149] [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.

[0150] <<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.

[0151] [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.

[0152] The organic electronic element may emit light from either the first electrode 21 or the second electrode 26, or from both sides. The electrode from which light is extracted is formed 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.

[0153] [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.

[0154] [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.

[0155] [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.

[0156] [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.

[0157] [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.

[0158] [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.

[0159] 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 be replaced with a layer formed by mixing a compound represented by formula (Q) with a hole transport material.

[0160] The present invention will be described in more detail below with reference to examples, but the present invention should not be construed as being limited to these examples.

[0161] (Synthesis Example 1: Synthesis of Compound (C-2)) Under an argon stream, 2.70 g (10.1 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 2.80 g (30.2 mmol) of acetoaminonitrile hydrochloride, and 1.11 g (8.56 mmol) of isoquinoline were suspended in 101 mL of DMF and stirred at 120°C for 5 hours. After cooling to room temperature, excess amounts of toluene and ethanol were added to cause crystallization, and the precipitate (crude product) was collected by filtration. The obtained crude product was purified by recrystallization from DMF to obtain the target compound (C-2) (2.60 g, yield 75%). The obtained compound (C-2) was identified as follows: １ H-NMR was used. １ H-NMR (DMSO-d6) δ (ppm): 5.11 (s, 4H), 8.76 (s, 4H).

[0162]

[0163] (Synthesis Example 2: Synthesis of Compound (C-72)) Under an argon stream, 2.00 g (7.46 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride, 1.07 g (15.3 mmol) of 2-cyanoethylamine, and 0.82 g (6.34 mmol) of isoquinoline were suspended in 30 mL of m-cresol and stirred at 120°C for 6 hours. After cooling to room temperature, the precipitate (crude product) was collected by filtration. The obtained crude product was purified by recrystallization from DMF to obtain the target compound (C-72) (2.30 g, yield 83%). The obtained compound (C-72) was identified as follows: １ H-NMR was used. １ H-NMR (DMSO-d6) δ (ppm): 2.97 (t, J = 6.6 Hz, 4H), 4.35 (t, J = 6.6 Hz, 4H), 8.74 (s, 4H).

[0164]

[0165] (Synthesis Example 3: Synthesis of Compound (C-42)) Under an argon stream, 0.93 g (3.47 mmol) of naphthalene-1,4,5,8-tetracarboxylic dianhydride and 1.40 g (8.30 mmol) of 2-amino-2-phenylacetonitrile hydrochloride were suspended in 35 mL of pyridine and stirred at 120°C for 7 hours. After cooling to room temperature, 70 mL of ethanol was added to the reaction solution, and the precipitate (crude product) was collected by filtration. The obtained crude product was purified by recrystallization from DMF to obtain the target compound (C-42) (1.00 g, yield 58%). １ H-NMR (DMSO-d6) δ (ppm): 7.37-7.46 (m, 6H), 7.57-7.61 (m, 6H), 8.74 (s, 4H).

[0166]

[0167] (Comparative Synthesis Example 2: Synthesis of Compound (R-1)) The following compound (R-1) was synthesized by the method described in Journal of the American Chemical Society (2011), 133(39), 15256-15259. １ H-NMR (DMSO-d ６ ) δ (ppm): 8.72 (s, 4H), 8.75 (s, 4H), 7.59-7.45 (m, 10H).

[0168]

[0169] [Compounds used in evaluation]

[0170] <Fabrication and Evaluation of Hole-Only Device (HOD)> [HOD 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.

[0171] (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.

[0172] (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 (C-2) was formed to prepare a hole transport promotion layer.

[0173] (Fabrication of Second Electrode) A 80 nm thick Au film was formed to fabricate a second electrode.

[0174] (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 HOD Example 1, respectively. ２ The voltage value at a current density of 1000 kJ / s was measured. The results are shown in Table 1.

[0175] [HOD Example 2] A hole-only device was fabricated in the same manner as in HOD Example 1, except that compound (C-72) was used instead of compound (C-2) used in the preparation of the hole transport promotion layer in HOD Example 1. The hole transport ability of the resulting hole-only device was evaluated in the same manner as in HOD Example 1. The results are shown in Table 1.

[0176] [HOD Example 3] A hole-only device was prepared in the same manner as in HOD Example 1, except that compound (C-42) was used instead of compound (C-2) used in preparing the hole transport promotion layer in HOD Example 1. The hole transport ability of the obtained hole-only device was evaluated in the same manner as in HOD Example 1. The results are shown in Table 1.

[0177] [HOD Comparative Example 1] A hole-only device was fabricated in the same manner as in HOD Example 1, except that compound (NPT) was used instead of compound (C-2) used in the preparation of the hole transport promotion layer in HOD Example 1. The hole transport ability of the resulting hole-only device was evaluated in the same manner as in HOD Example 1. The results are shown in Table 1.

[0178] [HOD Comparative Example 2] A hole-only device was fabricated in the same manner as in HOD Example 1, except that the hole transport promotion layer was not provided. The hole transport ability of the resulting hole-only device was evaluated in the same manner as in HOD Example 1. The results are shown in Table 1.

[0179]

[0180] The device of HOD Example 1 using compound (C-2) as the hole transport promoting material (HOD voltage: 0.58 V), the device of HOD Example 2 using compound (C-72) as the hole transport promoting material (HOD voltage: 0.93 V), and the device of HOD Example 3 using compound (C-42) as the hole transport promoting material (HOD voltage: 0.65 V) showed lower HOD voltages than the device of HOD Comparative Example 1 using the known material NPT (HOD voltage: 2.27 V) and the device of HOD Comparative Example 2 using no hole transport promoting material (HOD voltage: 4.42 V).

[0181] <Preparation and Evaluation of Photoelectric Conversion Element> [Element Example 1] 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.

[0182] (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 －５ The 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 (C-2) 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.

[0183] 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 1 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.

[0184] [Element Example 2] Photoelectric conversion element 1 was prepared in the same manner as in Element Example 1, except that compound (C-72) was used instead of compound (C-2) 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 1. The results are shown in Table 2.

[0185] [Element Example 3] Photoelectric conversion element 1 was prepared in the same manner as in Element Example 1, except that compound (C-42) was used instead of compound (C-2) 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 1. The results are shown in Table 2.

[0186] A photoelectric conversion element of Comparative Example 1 was prepared in the same manner as in Example 1, except that compound (NPT) was used instead of compound (C-2) 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 1. The results are shown in Table 2.

[0187] [Element Comparative Example 2] A photoelectric conversion element of Element Comparative Example 2 was prepared in the same manner as Element Example 1, except that the hole transport promotion layer 12 was not provided, and the dark current was measured in the same manner as Element Example 2. The results are shown in Table 2. In Element Comparative Example 2, the dark current was too large to measure the external quantum efficiency.

[0188] A photoelectric conversion element of Comparative Example 3 was prepared in the same manner as in Example 1, except that compound (R-1) was used instead of compound (C-2) 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 1. The results are shown in Table 2.

[0189]

[0190] As shown in Table 2, in the element examples 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 element examples of the element comparison examples.

[0191] <Film Quality Evaluation of Hole Transport Promotion Layer> [Example A-1] A Si substrate (with a native oxide film) was placed in a vacuum deposition chamber, and a 1.0 × 10 －４ The pressure was reduced to 100 Pa. Then, a film of 30 nm was formed on a substrate using the sublimation-purified compound (C-42), and the surface condition of the film was observed using an atomic force microscope (Shimadzu Corporation, SPM-9600). The arithmetic mean roughness (Ra) in the surface roughness measurement was 0.24 nm.

[0192] [Example A-2] Measurement was carried out in the same manner as in Example A-1, except that compound (C-2) was used instead of compound (C-42). The arithmetic mean roughness (Ra) in the surface roughness measurement was 6.67 nm.

[0193] [Comparative Example B-1] Measurement was carried out in the same manner as in Example A-1, except that compound (R-1) was used instead of compound (C-42). The arithmetic mean roughness (Ra) in the surface roughness measurement was 12.05 nm.

[0194] When the film quality was evaluated, it was found that, as described above, when the compounds of the examples were used, the surface roughness (Ra) could be suppressed to 10 nm or less, and the film quality could be improved compared to the compounds of the comparative examples.

[0195] By including the compound represented by formula (Q), the organic electronic device of the present invention can improve hole transport ability, and when used in a photoelectric conversion device, can perform photoelectric conversion more efficiently. Furthermore, by including the compound represented by formula (Q), the organic electronic device of the present invention can suppress dark current, and is expected to reduce noise when used in a photoelectric conversion device such as an imaging device. Furthermore, by including the compound represented by formula (Q), the organic electronic device of the present invention can have high external quantum efficiency and can convert light into current without loss, and is expected to achieve high sensitivity when used in, for example, a photoelectric conversion device.

[0196] 1. Photoelectric conversion element 11. First electrode 12. Hole transport promoting layer 13. Hole transport layer 14. Light receiving layer 15. Electron transport layer 16. Second electrode 2. Organic EL element 21. First electrode 22. Hole injection layer 23. Hole transport layer 24. Light emitting layer 25. Electron transport layer 26. Second electrode

Claims

1. An organic electronic device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a partial structure represented by the following formula (Q): In formula (Q), * represents a bond, and the bond constitutes a partial structure of a cyclic imide structure. １ represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and n represents 1, 2, or 3.

2. The organic electronic device according to claim 1, comprising a first electrode, a second electrode, and an organic layer and a light receiving layer disposed between the first electrode and the second electrode, wherein the organic layer contains a compound having a partial structure represented by formula (Q).

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

4. The organic electronic device according to any one of claims 1 to 3, wherein the organic layer comprises a hole transport layer and a hole transport promotion layer containing a compound having the partial structure represented by formula (Q), or comprises a layer comprising a mixture of a hole transport material and a compound having the partial structure represented by formula (Q).

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

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

7. R in the above formula (Q) １ The organic electronic device according to any one of claims 1 to 3, wherein is an unsubstituted methylene group or an unsubstituted ethylene group.

8. The organic electronic device according to any one of claims 1 to 3, wherein the compound having a partial structure represented by formula (Q) is a compound represented by the following formula (1): (In formula (1), R ２ and R ３ each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group being optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and each independently m and n represents 1, 2, or 3. ring A represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms, each of the aromatic hydrocarbon ring and the heteroaromatic ring may be a monocycle, a condensed ring or a linked ring, and the linked ring may be bonded through a methylene group substituted with a trifluoromethyl group, the aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms, the aromatic hydrocarbon ring and the heteroaromatic ring may be bonded to the aromatic hydrocarbon group or the heteroaromatic group through one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group, The aromatic hydrocarbon group and the heteroaromatic group may each be a single ring, a condensed ring, or a linked ring.

9. The organic electronic device according to claim 8, wherein the ring A in the formula (1) is any one of the following (A-1) to (A-17) which may be substituted with one or more groups.

10. R in the above formula (1) ２ and R ３ are each independently a methylene group or an ethylene group, and the methylene group and the ethylene group are optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms. The organic electronic device according to claim 8, 11. R in the above formula (1) ２ and R ３ The organic electronic device according to claim 8 , wherein each of the is independently an unsubstituted methylene group or an unsubstituted ethylene group.

12. A material for an organic electronic device, comprising a compound represented by the following formula (2): (In formula (2), R ４ and R ５ each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group being optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and each independently m and n represents 1, 2, or 3. ring B represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms, each of the aromatic hydrocarbon ring and the heteroaromatic ring may be a monocycle, a condensed ring or a linked ring, and the linked ring may be bonded to a methylene group substituted with a trifluoromethyl group, the aromatic hydrocarbon ring and the heteroaromatic ring may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and a heteroaromatic group having 3 to 20 carbon atoms, the aromatic hydrocarbon ring and the heteroaromatic ring may be bonded to the aromatic hydrocarbon group or the heteroaromatic group by one or more groups selected from an oxygen atom, a carbonyl group, and a thiocarbonyl group, The aromatic hydrocarbon group and the heteroaromatic group may each be a single ring, a condensed ring, or a linked ring.

13. The material for organic electronic devices according to claim 12, which is a material for photoelectric conversion devices.

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

15. R in the above formula (2) ４ and R ５ are each independently a methylene group or an ethylene group, and the methylene group and the ethylene group are optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

16. R in the above formula (2) ４ and R ５ The material for organic electronic devices according to any one of claims 12 to 15, wherein each of the is independently an unsubstituted methylene group or an unsubstituted ethylene group.

17. The material for organic electronic devices according to any one of claims 12 to 15, wherein the ring B in the formula (2) is any one of the following (B-1) to (B-17) which may be substituted with one or more groups.

18. An imide compound represented by the following formula (3) or (4): (In formula (3), T １ and T ２ R each independently represents a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. ６ and R ７ each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and each of m and n independently represents 1, 2, or 3. In formula (4), T ３ ~T ６ R each independently represents a hydrogen atom, a hydroxy group, a carboxy group, a formyl group, a nitro group, an amino group, a cyano group, a fluoro group, a chloro group, a bromo group, an iodo group, a fluoroalkyl group having 1 to 10 carbon atoms, a fluoroalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, or a substituent formed by combining two or more of these. ８ and R ９ each independently represents an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms, the aliphatic hydrocarbon group may be linear, branched, or cyclic, and m and n each independently represent 1, 2, or 3. However, T ３ = T ４ = T ５ = T ６ = hydrogen atom, and when m = n = 1, R ８ = R ９ = Not an unsubstituted methylene group, T ３ = T ４ = T ５ = T ６ = hydrogen atom, and when m = n = 1, R ８ = R ９ = Not a methylene group substituted with an isobutyl group, T ３ = T ４ = T ５ = T ６ = hydrogen atom, and when m = n = 1, R ８ = R ９ = Not an unsubstituted ethylene group.) 19. R in the formula (3) or (4) ６ ~R ９ are each independently a methylene group or an ethylene group, and the methylene group and the ethylene group are optionally substituted with one or more groups selected from a hydroxy group, a carboxy group, a formyl group, a nitro group, a fluoro group, a chloro group, a bromo group, an iodo group, a trifluoromethyl group, a cyano group, a carbon-oxygen double bond, a carbon-sulfur double bond, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, and an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

20. R in the formula (3) or (4) ６ ~R ９ The imide compound according to claim 18 , wherein each of the is independently an unsubstituted methylene group or an unsubstituted ethylene group.

21. R in the formula (3) or (4) ６ ~R ９ The imide compound according to claim 18 , wherein each independently is a methylene group substituted with a phenyl group, a cyanophenyl group, or a pyridyl group.

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