Material for photoelectric conversion element and photoelectric conversion element using same

Abstract

Provided are: a material which achieves high sensitivity and high resolution in an imaging photoelectric conversion element; and an imaging photoelectric conversion element which uses the material. A material for photoelectric conversion elements, which contains a compound represented by general formula (1), is used. In the formula (1), Ar1 to Ar3 represent deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl heteroarylamino group having 12 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or the like, at least one of Ar1 to Ar3 is any one of general formulae (2) to (5), or the like, X is C (Ar4Ar5), O, S, or the like, and a and b are integers from 0 to 4. * represents a bond node with general formula (1), and L1 and L2 represent any one of a direct bond, an aromatic hydrocarbon group having 6-18 carbon atoms, an aromatic heterocyclic group having 3-18 carbon atoms, or the like. Ar4 to Ar12 are the same as Ar1 to Ar3, c, e and f each represents an integer of 0 to 3, and d represents an integer of 0 to 2. [chemical] # imgabs0 # [chemical] # imgabs1 #

Description

Technical Field

[0001] The present invention relates to a photoelectric conversion element material and a photoelectric conversion element using the same, and more particularly to a photoelectric conversion element material that can be effectively used in an imaging device.

[0002] In recent years, the development of organic electronic devices using thin films formed of organic semiconductors is being promoted. For example, electric field light-emitting elements, solar cells, transistor elements, photoelectric conversion elements, etc. can be exemplified. In particular, among these, the development of organic electroluminescence (EL) elements, which are electric field light-emitting elements based on organic matter, is the most advanced, and while promoting their application in smart phones or televisions (TV), they continue to be developed with the goal of higher functionality.

[0003] On the other hand, the development and practical application of PN junction elements of inorganic semiconductors such as silicon that were previously used in photoelectric conversion elements for video recording have been promoted, and research on the high-functionality of digital cameras and smartphone cameras, and research on applications in surveillance cameras, automotive sensors, etc., are being conducted. As issues for coping with these various uses, high sensitivity and pixel miniaturization (high resolution) are listed. In previous photoelectric conversion elements using inorganic semiconductors, in order to obtain color images, a method of configuring a color filter corresponding to red, green, and blue (RGB), which are the three primary colors of light, on the light-receiving portion of the photoelectric conversion element is mainly adopted. In the above method, since the RGB color filter is configured on a plane, there are issues in terms of the utilization efficiency or resolution of the incident light (non-patent document 1, non-patent document 2).

[0004] As one of the solutions to the problem of such photoelectric conversion elements, the development of photoelectric conversion elements using organic semiconductors instead of inorganic semiconductors is being carried out (Non-Patent Document 1, Non-Patent Document 2). It utilizes the property of organic semiconductors that they can selectively absorb only light in a specific wavelength region with high sensitivity, and proposes to solve the problem of high sensitivity and high resolution by laminating photoelectric conversion elements obtained by using organic semiconductors corresponding to the three primary colors of light. In addition, an element obtained by laminating a photoelectric conversion element including an organic semiconductor and a photoelectric conversion element including an inorganic semiconductor has also been proposed (Non-Patent Document 3).

[0005] Here, the photoelectric conversion element using an organic semiconductor is an element constructed in the following manner, that is, a photoelectric conversion layer having a thin film containing an organic semiconductor between two electrodes, and a hole blocking layer and / or an electron blocking layer are configured between the photoelectric conversion layer and the two electrodes as needed. In the photoelectric conversion element, excitons are generated by absorbing light with a desired wavelength using the photoelectric conversion layer, and then holes and electrons are generated by charge separation of the excitons. Afterwards, holes and electrons migrate to each electrode to convert light into an electrical signal. For the purpose of promoting the process, a method of applying a bias voltage between the two electrodes is generally used, but reducing the leakage current from the two electrodes generated by applying the bias voltage becomes one of the topics. In this case, it can be said that controlling the migration of holes or electrons in the photoelectric conversion element is the key to the manifestation of the characteristics of the photoelectric conversion element.

[0006] The organic semiconductors used in each layer of the photoelectric conversion element can be roughly divided into P-type organic semiconductors and N-type organic semiconductors. The P-type organic semiconductors are used as hole transport materials, and the N-type organic semiconductors are used as electron transport materials. In order to control the migration of holes and electrons in the photoelectric conversion element, various organic semiconductors with appropriate physical properties, such as hole mobility, electron mobility, energy value of the highest occupied molecular orbital (HOMO), and energy value of the lowest unoccupied molecular orbital (LUMO) have been developed, but it is still not possible to say that they have sufficient characteristics.

[0007] Furthermore, various compounds that are excellent as hole transport materials or electron blocking materials for organic electroluminescent elements or organic solar cells are disclosed, but these compounds are not necessarily excellent as hole transport materials or electron blocking materials for imaging. Specifically, as one of the important characteristics required of hole transport materials for photoelectric conversion elements for imaging, for example, in order for a camera to take clear images in a dark place, it is important to increase the difference between the current value in the state where the shutter is closed and the current value in the state where the shutter is open (brightness-darkness ratio), so the lower the current value in the dark place, the better, and the higher the current value in the bright place, the better. That is, it is important to have a "high brightness-darkness ratio".

[0008] On the other hand, in organic electroluminescent elements, the voltage required to flow a certain current, the luminous efficiency, the element life, etc. are the characteristics to be improved, which are very different from the characteristics required for photoelectric conversion elements for imaging. In addition, it is important for organic solar cells to generate a large amount of current in both dark and bright places, which is different from the characteristics required for photoelectric conversion elements for imaging, which preferably have a low current value in the dark.

[0009] As described above, the required properties are different between the hole transport material or electron blocking material of an organic electric field light-emitting element or an organic solar cell and the hole transport material or electron blocking material of a photoelectric conversion element for imaging. Therefore, it is not clear whether a material that is excellent as a hole transport material or electron blocking material for an organic electric field light-emitting element or an organic solar cell is excellent as a hole transport material or electron blocking material for a photoelectric conversion element for imaging until it is confirmed through experiments.

[0010] Patent Document 1 proposes an element using quinacridone as a P-type organic semiconductor in a photoelectric conversion layer, using subphthalocyanine chloride as an N-type organic semiconductor, and using an indolocarbazole derivative in a first buffer layer disposed between the photoelectric conversion layer and an electrode.

[0011] In addition, Patent Document 2 proposes the following element: The dithiophene derivative is used as a P-type organic semiconductor, and the fullerene or subphthalocyanine derivative is used as an N-type organic semiconductor.

[0012] Furthermore, Patent Documents 3 and 4 propose devices in which a carbazole derivative is used in an electron blocking layer disposed between a photoelectric conversion layer and an electrode.

[0013] Furthermore, Patent Document 5 proposes a device in which a pyrene derivative or a terphenylene derivative is used in an electron blocking layer disposed between a photoelectric conversion layer and an electrode.

[0014] Prior art literature

[0015] Patent Literature

[0016] Patent Document 1: Japanese Patent Application Publication No. 2018-85427

[0017] Patent Document 2: Japanese Patent Application Publication No. 2019-54228

[0018] Patent Document 3: Japanese Patent Application Publication No. 2011-228614

[0019] Patent Document 4: Japanese Patent Application Publication No. 2021-77888

[0020] Patent Document 5: Japanese Patent Application Publication No. 2015-153910

[0021] Non-patent literature

[0022] Non-patent document 1: NHK R&D No. 132, pp. 4-11 (2012.3)

[0023] Non-patent document 2: NHK R&D No. 174, pp. 4-17 (2019.3)

[0024] Non-patent document 3: 2019 Institute of Electrical and Electronics Engineers (IEEE) International Electron Devices Meeting (IEDM), pp. 16.6.1-16.6.4 (2019) Summary of the invention

[0025] Problems to be solved by the invention

[0026] For photoelectric conversion elements for imaging, higher sensitivity and higher resolution have become a problem in order to promote the high functionality of digital cameras and smartphone cameras, or their application in surveillance cameras, automotive sensors, etc. In view of this situation, the present invention aims to provide a material for achieving high sensitivity and high resolution of photoelectric conversion elements for imaging, and a photoelectric conversion element for imaging using the material.

[0027] Means of solving problems

[0028] The present inventors have conducted intensive research and have found that the process of generating holes and electrons by charge separation of excitons in a photoelectric conversion layer and the process of migration of holes and electrons in a photoelectric conversion element can be efficiently promoted by using a specific compound, thereby completing the present invention.

[0029] The present invention is a photoelectric conversion element material characterized by containing a compound represented by the following general formula (1).

[0030] [Chemistry 1]

[0031]

[0032] In the general formula (1),

[0033] Ar 1 ~Ar 3Each of them independently represents deuterium, cyano, halogen, nitro, alkyl having 1 to 20 carbon atoms, aralkyl having 7 to 38 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, acyl having 2 to 20 carbon atoms, acyloxy having 2 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkoxycarbonyl having 2 to 20 carbon atoms, alkoxycarbonyloxy having 2 to 20 carbon atoms, alkylsulfonyl having 1 to 20 carbon atoms, dialkylamino having 2 to 20 carbon atoms, substituted or unsubstituted alkylarylamino having 7 to 28 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 36 carbon atoms, a substituted or unsubstituted arylheteroarylamino group having 12 to 36 carbon atoms, a substituted or unsubstituted diheteroarylamino group having 12 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group in which 2 to 10 aromatic groups of the aromatic hydrocarbon group and the aromatic heterocyclic group are linked, Ar 1 ~Ar 3 At least one of the following general formulae (2) to (8) is represented by any one of the following general formulae (2) to (8). 1 ~Ar 3 In the case of a group having a hydrogen atom, the hydrogen atom may be substituted with deuterium or a halogen.

[0034] X represents C(Ar 4 Ar 5 ), NAr 6 , O, or S.

[0035] a and b represent the number of substitutions, and each independently represents an integer of 0 to 4.

[0036] [Chemistry 2]

[0037]

[0038] In general formula (2) to general formula (8),

[0039] * indicates the bonding point with the general formula (1).

[0040] L 1 and L 2 Each independently represents a direct bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two or three of these aromatic rings are linked.

[0041] Ar 4 ~Ar 12 Separately with Ar 1 ~Ar 3 The narrator is the same as in Ar4 ~Ar 12 When it represents a linked aromatic group, it represents a substituted or unsubstituted linked aromatic group in which two to three aromatic rings are linked. 4 ,Ar 5 They can bond with each other to form a ring structure.

[0042] c to f represent the number of substitutions, c, e, and f each independently represent an integer of 0 to 3, and d represents an integer of 0 to 2.

[0043] The general formula (1) is preferably represented by any one of the following general formulas (9) to (12). The general formula (1) is more preferably represented by any one of the following general formulas (9), (11) and (12), and is further preferably represented by any one of the following general formulas (11) and (12).

[0044] [Chemistry 3]

[0045]

[0046] Furthermore, in the general formulas (9) to (12), Ar 1 ~Ar 6 , and a, b are the same as those described in the general formula (1).

[0047] Preferably, Ar in the general formula (1) 1 ~Ar 3 At least one of them is represented by any one of the general formulae (2) to (8), and more preferably, it is represented by any one of the general formulae (2), (3), (5), (7), and (8).

[0048] In addition, L in the general formulae (2) to (8) 1 A single bond is preferred.

[0049] In the photoelectric conversion element material, the energy level of the highest occupied molecular orbital (HOMO) obtained by structure optimization calculation based on density functional calculation B3LYP / 6-31G(d) is preferably below -4.0 eV, and the energy level of the lowest unoccupied molecular orbital (LUMO) is preferably above -2.5 eV.

[0050] The photoelectric conversion element material preferably has a 1×10 -6 cm 2 / Vs or more. In addition, the photoelectric conversion element material is preferably amorphous.

[0051] The photoelectric conversion element material can be used as a hole transport material.

[0052] In addition, the present invention is a photoelectric conversion element having a photoelectric conversion layer and an electron blocking layer between two electrodes, wherein the photoelectric conversion element for imaging is characterized in that at least one of the photoelectric conversion layer and the electron blocking layer contains the photoelectric conversion element material.

[0053] The photoelectric conversion element of the present invention may contain the above-mentioned photoelectric conversion element material in the electron blocking layer, and may contain an electron transporting material such as a fullerene derivative in the photoelectric conversion layer.

[0054] Effects of the Invention

[0055] The photoelectric conversion element material of the present invention can be applied to the photoelectric conversion element for imaging, and can also be applied to other sensors or solar cells that convert light information into signals. It is believed that when the photoelectric conversion element material of the present invention is applied to the photoelectric conversion element for imaging, appropriate migration of holes or electrons can be achieved, so that the leakage current generated by applying a bias voltage when converting light into electrical energy can be reduced, and as a result, a photoelectric conversion element with a low dark current value and a high light-dark ratio can be obtained. Therefore, the material of the present invention is effectively used as a photoelectric conversion element material for a photoelectric conversion film laminated imaging device. BRIEF DESCRIPTION OF THE DRAWINGS

[0056] [ Figure 1 ] is a cross-sectional schematic diagram showing a structural example of the photoelectric conversion element used in the present invention. DETAILED DESCRIPTION

[0057] The photoelectric conversion element in the present invention is a photoelectric conversion element having at least one organic layer between two electrodes and converting light into electrical energy. The organic layer contains a photoelectric conversion element material containing a compound represented by the general formula (1). Specifically, in a camera photoelectric conversion element having a photoelectric conversion layer and an electron blocking layer between two electrodes, at least one of the photoelectric conversion layer and the electron blocking layer contains a photoelectric conversion element material represented by the general formula (1). Hereinafter, the photoelectric conversion element material containing a compound represented by the general formula (1) is referred to as a photoelectric conversion element material. In addition, it is sometimes referred to as the material of the present invention or the compound represented by the general formula (1).

[0058] The compound represented by the general formula (1) is described below.

[0059] A preferred embodiment of the general formula (1) is represented by the general formulas (9) to (12), and is preferably represented by the general formula (9), (11), or (12), among which it is more preferably represented by the general formula (11) or (12).

[0060] In the general formulas (9) to (12), Ar 1~Ar 6 , and a, b are the same as those described in the general formula (1).

[0061] In the general formula (1), Ar 1 ~Ar 3 At least one of the above general formulae (2) to (8) is represented by any one of the general formulae, but preferably Ar 1 It is represented by any one of the general formulas (2) to (8).

[0062] In the general formula (1), Ar 1 ~Ar 3 At least one of them is represented by any one of the general formulas (2) to (8), but is preferably represented by any one of the general formulas (2), (3), (5), (7), or (8), and is more preferably represented by any one of the general formulas (2), (5), or (8).

[0063] In general formulae (2) to (8), * represents the bonding point with general formula (1), L 1 , L 2 ,Ar 4 ~Ar 12 , c to f are the same as those described in the general formulae (2) to (8).

[0064] Ar 1 ~Ar 3 each independently represents deuterium, cyano, halogen, nitro, alkyl having 1 to 20 carbon atoms, aralkyl having 7 to 38 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, acyl having 2 to 20 carbon atoms, acyloxy having 2 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkoxycarbonyl having 2 to 20 carbon atoms, alkoxycarbonyloxy having 2 to 20 carbon atoms, alkylsulfonyl having 1 to 20 carbon atoms, dialkylamino having 2 to 20 carbon atoms, substituted or unsubstituted alkylarylamino having 7 to 28 carbon atoms, A substituted or unsubstituted diarylamine group having 12 to 36 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 12 to 36 carbon atoms, a substituted or unsubstituted diheteroarylamine group having 12 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking 2 to 10 aromatic groups of the aromatic hydrocarbon group and the aromatic heterocyclic group. Among them, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 6 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking 2 to 10 aromatic groups of the aromatic hydrocarbon group and the aromatic heterocyclic group is preferred. In addition, in Ar 1 ~Ar3 In the case where these groups have hydrogen atoms, the hydrogen atoms may be substituted by deuterium or halogen. 1 ~Ar 3 At least one of the above-mentioned general formulae (2) to (8) is represented by any one of the general formulae (2) to (8).

[0065] Ar 1 ~Ar 3 The alkyl group having 1 to 20 carbon atoms may be any of a linear, branched, or cyclic alkyl group, and is preferably a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms. Specific examples thereof include linear saturated hydrocarbon groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, n-dodecyl, n-tetradecyl, and n-octadecyl, branched saturated hydrocarbon groups such as isopropyl, isobutyl, neopentyl, 2-ethylhexyl, and 2-hexyloctyl, and saturated alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cyclooctyl, and 4-butylcyclohexyl.

[0066] In addition, specific examples of aralkyl groups having 7 to 38 carbon atoms include benzyl, phenethyl, phenylpropyl, phenylbutyl, naphthylmethyl, triphenylmethyl, etc. Specific examples of alkenyl groups having 2 to 20 carbon atoms include ethylene, propylene, butylene, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, octenyl, etc. Specific examples of alkynyl groups having 2 to 20 carbon atoms include ethynyl, propynyl, butynyl, pentynyl, etc. Specific examples of acyl groups having 2 to 20 carbon atoms include formyl, acetyl, propionyl, benzoyl, etc. Specific examples of acyloxy groups having 2 to 20 carbon atoms include formyl, acetyl, propionyl, butyryl, benzoyl, acryloyl, crotonoyl, etc. Specific examples of alkoxy groups having 1 to 20 carbon atoms include methoxy, ethoxy, propoxy, butoxy, etc. Specific examples of the alkoxycarbonyl group having 2 to 20 carbon atoms include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, and pentyloxycarbonyl. Specific examples of the alkoxycarbonyloxy group having 2 to 20 carbon atoms include methoxycarbonyloxy, ethoxycarbonyloxy, propoxycarbonyloxy, butoxycarbonyloxy, and pentyloxycarbonyloxy. Specific examples of the alkylsulfonyl group having 1 to 20 carbon atoms include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, and pentylsulfonyl.

[0067] Yu Ar 1 ~Ar 3In the case of an amino group, a dialkylamino group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylarylamino group having 7 to 28 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 36 carbon atoms, a substituted or unsubstituted arylheteroarylamino group having 12 to 36 carbon atoms, a substituted or unsubstituted diheteroarylamino group having 12 to 36 carbon atoms, etc. are represented. Specific examples of the alkyl group include straight-chain saturated hydrocarbon groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, and n-octyl, branched saturated hydrocarbon groups such as isopropyl, isobutyl, neopentyl, and 2-ethylhexyl, and saturated alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cyclooctyl, and 4-butylcyclohexyl. Specific examples of the aryl group include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene, pyrenyl, fluorenyl, and spirobifluorenyl. Specific examples of heteroaryl groups include pyrrole, pyrrolopyrrole, indole, pyrroloindole, benzindole, naphthopyrrole, isoindole, pyrroloisoindole, benzisoindole, naphthoisopyrrole, carbazole, phenoxazine, phenathiazine, acridine, phenazine, benzocarbazole, indoloindole, indolcarbazole, carbazolecarbazole, benzofuranocarbazole, benzothiophenocarbazole, carboline, thiophene, benzothiophene, naphthothiophene, dibenzothiophene, benzo The dialkylamino group includes a group derived from thieno-naphthalene, benzothienobenzothiophene, benzothieno-dibenzothiophene, dinaphthothiophene, dinaphthothieno-thiophene, naphthobenzothiophene, furan, benzofuran, naphthofuran, dibenzofuran, benzofuranonaphthalene, benzofuranobenzofuran, benzofurano-dibenzofuran, dinaphthofuran, dinaphthofuranofuran, naphthobenzofuran, pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, etc. Specific examples of the dialkylamino group include a group derived from a dimethylamino group, a methylethylamino group, a diethylamino group, a dipropylamino group, a di-n-butylamino group, a di-tert-butylamino group, a dipentylamino group, a dihexylamino group, a dicyclohexylamino group, a diheptylamino group, a dioctylamino group, a dinonylamino group, a didecylamino group, etc. As specific examples of alkylarylamino groups, groups derived from methylphenylamino groups, ethylphenylamino groups, propylphenylamino groups, butylphenylamino groups, cyclohexylphenylamino groups, cyclohexylnaphthylamino groups, cyclohexylfluorenylamino groups, cyclohexylphenanthrylamino groups, cyclohexylfluorenanthrylamino groups, cyclohexyltriphenyleneamino groups, etc. can be cited. As specific examples of diarylamino groups, groups derived from diphenylamino groups, phenylnaphthylamino groups, dinaphthylamino groups, phenylanthrylamino groups, phenylfluorenylamino groups, phenylphenanthrylamino groups, phenylfluorenanthrylamino groups, phenyltriphenyleneamino groups, difluorenylamino groups, naphthyltriphenyleneamino groups, di-triphenyleneamino groups, etc. can be cited. As specific examples of arylheteroarylamino groups, groups derived from phenylpyridylamino groups, phenylindolyl groups, phenyldibenzofuranylamino groups, phenyldibenzophenylthioamino groups, etc. can be cited.Specific examples of the diheteroarylamine group include groups derived from a bis-dibenzofuranylamine group, a bis-dibenzophenylthioamine group, a bis-carbazolylamine group, a dibenzofuranylcarbazolylamine group, a dibenzofuranyldibenzophenylthioamine group, a dibenzophenylthiocarbazolylamine group, and the like.

[0068] In addition, in Ar 1 ~Ar 3 In the unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, there can be mentioned a group obtained by removing one hydrogen atom from a known aromatic hydrocarbon. Examples of such aromatic hydrocarbon groups include monocyclic aromatic hydrocarbons such as benzene, bicyclic aromatic hydrocarbons such as naphthalene, indacene, biphenylene, phenanthrene, anthracene, phenanthrene, tricyclic aromatic hydrocarbons such as fluorene, fluoranthene, acephenanthrylene, aceanthrylene, terphenylene, pyrene, A group derived from tetracyclic aromatic hydrocarbons such as tetraphene, tetraphenylene, and pleiadene. Preferably, the group is a group derived from benzene, naphthalene, anthracene, phenanthrene, triphenylene, or pyrene.

[0069] In addition, in Ar 1 ~Ar 3 In the unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, there can be mentioned a group obtained by removing one hydrogen atom from an aromatic heterocyclic group. Such an aromatic heterocyclic group can be, for example, pyrrole, pyrrolopyrrole, indole, pyrroloindole, benzindole, naphthopyrrole, isoindole, pyrroloisoindole, benzisoindole, naphthoisopyrrole, carbazole, benzocarbazole, indoloindole, carbazolecarbazole, indolicorbazole, a nitrogen-containing aromatic compound having a pyrrole ring such as carboline, thiophene, benzothiophene, naphthothiophene, phenothiazine, dibenzothiophene, benzothieno-naphthalene, benzothienobenzothiophene, benzothieno-dibenzothiophene, dinaphthothiophene, dibenzo ... Examples include sulfur-containing aromatic compounds having a thiophene ring such as naphthothienothiophene, naphthobenzothiophene, and benzothienocarbazole, furan, benzofuran, naphthofuran, phenoxazine, dibenzofuran, benzofuranonaphthalene, benzofuranobenzofuran, benzofuranodibenzofuran, dinaphthofuran, dinaphthofuranofuran, naphthobenzofuran, benzofuranocarbazole, oxygen-containing aromatic compounds having a furan ring such as pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, and quinoxaline. Preferred are groups derived from dibenzofuran, dibenzothiophene, carbazole, phenoxazine, phenoxathiazine, benzothienodibenzothiophene, benzofuranodibenzofuran, benzofuranocarbazole, or benzothienocarbazole.

[0070] Furthermore, in this specification, an unsubstituted linked aromatic group formed by linking aromatic groups of an aromatic hydrocarbon group and an aromatic heterocyclic group refers to an aromatic group formed by linking two or more aromatic groups through a single bond. These linked aromatic groups may be straight-chain or branched. The linking position when the benzene rings are linked to each other may be any of ortho, meta, or para, preferably para or meta. The aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group, and a plurality of aromatic groups may be the same or different.

[0071] Here, in Ar 1 ~Ar 3 When Ar represents a linked aromatic group, the number of linked aromatic groups is 2 to 10, preferably 2 to 8, and more preferably 2 to 6. 1 ~Ar 3 The number of linkages when aromatic groups are linked is two carbazole (CBZ) groups, L 1 , L 2 , and Ar 6 ~Ar 12 The total number of linkages of the aromatic hydrocarbon groups and aromatic heterocyclic groups contained in .

[0072] In the general formula (1) and general formulae (9) to (12), a and b represent the number of substitutions and each independently represents an integer of 0 to 4, preferably 0 to 2, and more preferably 0.

[0073] In general formulae (2) to (8), L 1 and L 2 Each independently represents a direct bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two or three of these aromatic rings are linked. 1 It is preferably a direct bond or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, and more preferably a direct bond. 2 It is preferably a direct bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, and more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms. 1 and L 2 Specific examples of the unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms and the unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms include, except for the group obtained by removing two hydrogen atoms from an aromatic hydrocarbon, 1 ~Ar 3 The same as described in the description.

[0074] Furthermore, in L 1 , and L 2In the case of a linked aromatic group, the two carbazole (CBZ) groups described in formulas (2) to (8) and formula (1) may be bonded by any one of the aromatic hydrocarbon groups or aromatic heterocyclic groups contained in the linked aromatic group, and may be bonded at both ends or in a branched form.

[0075] c to f represent the number of substitutions, and c, e, and f each independently represent an integer of 0 to 3, preferably 0 to 1. d represents an integer of 0 to 2, preferably 0.

[0076] Ar 4 ~Ar 12 Separately with Ar 1 ~Ar 3 The narrator is the same as in Ar 4 ~Ar 12 When it represents a linked aromatic group, it represents a substituted or unsubstituted linked aromatic group formed by linking 2 to 3 aromatic rings. 4 ,Ar 5 They can bond with each other to form a ring structure.

[0077] Yu Ar 1 ~Ar 12 In the case of an alkylarylamine group having 7 to 28 carbon atoms, a diarylamine group having 12 to 36 carbon atoms, an arylheteroarylamine group having 12 to 36 carbon atoms, a diheteroarylamine group having 12 to 36 carbon atoms, an aromatic hydrocarbon group, an aromatic heterocyclic group, or a linked aromatic group, these may have a substituent. As the substituent, deuterium, an alkyl group having 1 to 20 carbon atoms, a cyano group, an alkylsilane group, etc. may be listed. The alkyl group having 1 to 20 carbon atoms may be any one of a linear, branched, or cyclic alkyl group. Among the substituents, deuterium, a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms, or a cyano group is preferred. Specific examples thereof include: straight-chain saturated hydrocarbon groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, n-dodecyl, n-tetradecyl, and n-octadecyl, branched saturated hydrocarbon groups such as isopropyl, isobutyl, neopentyl, 2-ethylhexyl, and 2-hexyloctyl, and saturated alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cyclooctyl, 4-butylcyclohexyl, and 4-dodecylcyclohexyl. In addition, substitution in the present invention is based on an aromatic ring.

[0078] Preferred specific examples of the compound represented by the general formula (1) as the photoelectric conversion element material of the present invention are shown below, but the present invention is not limited to these.

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[0136]

[0137] [Chemistry 33]

[0138]

[0139] [Chemistry 34]

[0140]

[0141] [Chemistry 35]

[0142]

[0143] [Chemistry 36]

[0144]

[0145] [Chemistry 37]

[0146]

[0147] [Chemistry 38]

[0148]

[0149] [Chemistry 39]

[0150]

[0151] [Chemistry 40]

[0152]

[0153] [Chemistry 41]

[0154]

[0155] [Chemistry 42]

[0156]

[0157] [Chemistry 43]

[0158]

[0159] [Chemistry 44]

[0160]

[0161] [Chemistry 45]

[0162]

[0163] [Chemistry 46]

[0164]

[0165] [Chemistry 47]

[0166]

[0167] [Chemistry 48]

[0168]

[0169] [Chemistry 49]

[0170]

[0171] [Chemistry 50]

[0172]

[0173] [Chemistry 51]

[0174]

[0175] [Chemistry 52]

[0176]

[0177] [Chemistry 53]

[0178]

[0179] [Chemistry 54]

[0180]

[0181] The compound represented by the general formula (1) of the present invention can be obtained by synthesizing it by a method based on various organic synthesis reactions established in the field of organic synthetic chemistry including coupling reactions such as Suzuki coupling, Stille coupling, Grignard coupling, Ullmann coupling, Buchwald-Hartwig reaction, and Heck reaction using commercially available reagents as raw materials, and then purifying it by a known method such as recrystallization, column chromatography, and sublimation purification, but the method is not limited to the above methods.

[0182] Regarding the photoelectric conversion element material of the present invention, the energy level of the highest occupied molecular orbital (HOMO) obtained by structure optimization calculation based on density functional calculation B3LYP / 6-31G (D) is preferably below -4.0 eV, more preferably in the range of -6.0 eV to -4.3 eV, and further preferably in the range of -4.9 eV to -4.4 eV.

[0183] Regarding the photoelectric conversion element material of the present invention, the energy level of the lowest unoccupied molecular orbital (LUMO) obtained by structure optimization calculation based on density functional calculation B3LYP / 6-31G (D) is preferably above -2.5 eV, more preferably in the range of -2.0 eV to -0.5 eV, and further preferably in the range of -1.5 eV to -1.0 eV.

[0184] Regarding the photoelectric conversion element material of the present invention, the difference (absolute value) between the HOMO energy level and the LUMO energy level is preferably in the range of 2.0 eV to 5.0 eV, more preferably in the range of 2.5 eV to 4.5 eV, and further preferably in the range of 3.5 eV to 4.5 eV.

[0185] The photoelectric conversion element material of the present invention may have a 1×10 -6 cm 2 / Vs or more, the hole mobility may preferably be 1×10 -5 cm 2 / Vs~1cm 2 / Vs, more preferably has a hole mobility of 1.0×10 -4 cm 2 / Vs~1×10 -2 cm 2 The hole mobility can be evaluated by a known method such as a method based on a field effect transistor (FET) type transistor element, a method based on a time-of-flight method, or a space charge limited current (SCLC) method.

[0186] The photoelectric conversion element material of the present invention is preferably amorphous. The amorphous state can be confirmed by various methods, for example, by not detecting a peak by X-ray diffraction (XRD) or by not detecting an endothermic peak by differential scanning calorimetry (DSC).

[0187] Next, an imaging photoelectric conversion element using the photoelectric conversion element material of the present invention will be described, but the structure of the imaging photoelectric conversion element of the present invention is not limited thereto.

[0188] Figure 1 1 is a cross-sectional view schematically showing a structural example of the imaging photoelectric conversion element of the present invention, wherein 1 represents an electrode, 2 represents a hole blocking layer, 3 represents a photoelectric conversion layer, 4 represents an electron blocking layer, 5 represents an electrode, and 6 represents a substrate. Figure 1 Inverted structure, that is, 1 is an electrode, 2 is an electron blocking layer, 3 is a photoelectric conversion layer, 4 is a hole blocking layer, 5 is an electrode, and 6 is a substrate. Figure 1 The structure can add or omit layers as needed.

[0189] -electrode-

[0190] The electrode used in the imaging photoelectric conversion element using the imaging photoelectric conversion element material of the present invention has the function of capturing holes and electrons generated in the photoelectric conversion layer. In addition, the function of allowing light to enter the photoelectric conversion layer is also required. Therefore, it is ideal that at least one of the two electrodes is transparent or translucent. In addition, the material used as the electrode is not particularly limited as long as it is a conductive material, and examples thereof include: indium tin oxide (ITO), indium zinc oxide (IZO), SnO 2 , antimony dopedtin oxide (ATO), ZnO, aluminum doped zinc oxide (AZO), gallium doped zinc oxide (GZO), TiO 2 Conductive transparent materials such as fluorine doped tin oxide (FTO), metals such as gold, silver, platinum, chromium, aluminum, iron, cobalt, nickel and tungsten, inorganic conductive materials such as copper iodide and copper sulfide, conductive polymers such as polythiophene, polypyrrole and polyaniline, etc. These materials can be mixed and used in multiple ways as needed. In addition, two or more layers can be stacked.

[0191] -Photoelectric conversion layer-

[0192] The photoelectric conversion layer is a layer that generates holes and electrons by charge separation of excitons generated by incident light. It can be formed by a single photoelectric conversion material, or it can be formed by combining with a P-type organic semiconductor material as a hole transport material, or an N-type organic semiconductor material as an electron transport material. In addition, two or more P-type organic semiconductors can be used, and two or more N-type organic semiconductors can also be used. It is ideal that one or more of these P-type organic semiconductors and / or N-type organic semiconductors use a pigment material having the function of absorbing light of a desired wavelength in the visible region. As a P-type organic semiconductor material for a hole transport material, a compound represented by the general formula (1) of the present invention can be used.

[0193] As the P-type organic semiconductor material, any material having hole transport properties may be used, and preferably the material represented by the general formula (1) is used, but other P-type organic semiconductor materials may also be used. In addition, two or more materials represented by the general formula (1) may be used in combination. Furthermore, the compound represented by the general formula (1) and other P-type organic semiconductor materials may also be used in combination.

[0194] As other P-type organic semiconductor materials, any material having hole transport properties may be used, for example, naphthalene, anthracene, phenanthrene, pyrene, Compounds having condensed polycyclic aromatic groups such as condensed tetraphenyl, triphenylene, perylene, fluoranthene, fluorene, and indene; compounds having π-excess aromatic groups such as cyclopentadiene derivatives, furan derivatives, thiophene derivatives, pyrrole derivatives, benzofuran derivatives, benzothiophene derivatives, dinaphthothiophene derivatives, indole derivatives, pyrazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, indolecarbazole derivatives; aromatic amine derivatives, styrylamine derivatives, benzidine derivatives, porphyrin derivatives, phthalocyanine derivatives, and quinacridone derivatives.

[0195] In addition, as polymeric P-type organic semiconductor materials, there can be exemplified: polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, polythiophene derivatives. In addition, two or more selected from the compounds represented by general formula (1), P-type organic semiconductor materials or polymeric P-type organic semiconductor materials can also be used in combination.

[0196] As the N-type organic semiconductor material, any material having electron transport properties may be used, for example, naphthalenetetracarboxylic acid diimide or perylenetetracarboxylic acid diimide, fullerenes, imidazole, thiazole, thiadiazole, oxazole, oxadiazole, triazole and other azole derivatives, etc. In addition, two or more selected from the N-type organic semiconductor materials may be used in combination.

[0197] -Electron blocking layer-

[0198] The electron blocking layer is provided to suppress the dark current generated by injecting electrons from one of the electrodes into the photoelectric conversion layer when a bias voltage is applied between the two electrodes. In addition, it also has the function of transporting holes generated by charge separation in the photoelectric conversion layer to the electrode, and a single layer or multiple layers can be configured as needed. A P-type organic semiconductor material as a hole transport material can be used in the electron blocking layer. As a P-type organic semiconductor material, any material having hole transport properties can be used, preferably a compound represented by general formula (1), and other P-type organic semiconductor materials can also be used. In addition, the compound represented by general formula (1) and other P-type organic semiconductor materials can also be used in combination. As other P-type organic semiconductor materials, any material having hole transport properties can be used, for example, naphthalene, anthracene, phenanthrene, pyrene, Compounds having condensed polycyclic aromatic groups such as condensed tetraphenyl, triphenylene, perylene, fluoranthene, fluorene, and indene; compounds having π-excess aromatic groups such as cyclopentadiene derivatives, furan derivatives, thiophene derivatives, pyrrole derivatives, benzofuran derivatives, benzothiophene derivatives, dinaphthothiophene derivatives, indole derivatives, pyrazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, and carbazole derivatives; aromatic amine derivatives, styrylamine derivatives, benzidine derivatives, porphyrin derivatives, phthalocyanine derivatives, and quinacridone derivatives.

[0199] In addition, as polymeric P-type organic semiconductor materials, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, polythiophene derivatives can be exemplified. In addition, two or more selected from the compounds represented by the general formula (1) of the present invention, P-type organic semiconductor materials or polymeric P-type organic semiconductor materials can also be used in combination.

[0200] -Hole blocking layer-

[0201] The hole blocking layer is provided to suppress the dark current generated by the injection of holes from one of the electrodes into the photoelectric conversion layer when a bias voltage is applied between the two electrodes. In addition, it also has the function of electron transport, which is to transport electrons generated by charge separation in the photoelectric conversion layer to the electrode, and can be configured as a single layer or multiple layers as needed. An N-type organic semiconductor with electron transport properties can be used in the hole blocking layer.

[0202] As the N-type organic semiconductor material, any material having electron transport properties may be used, for example, polycyclic aromatic polycarboxylic acid anhydrides such as naphthalenetetracarboxylic acid diimide or perylenetetracarboxylic acid diimide or imides thereof, fullerenes such as C60 or C70, azole derivatives such as imidazole, thiazole, thiadiazole, oxazole, oxadiazole, triazole, tris(8-hydroxyquinolinol)aluminum(III) derivatives, phosphine oxide derivatives, nitrosubstituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, anthraquinone dimethane derivatives and anthrone derivatives, bipyridine derivatives, quinoline derivatives, indolocarbazole derivatives, etc. In addition, two or more of these N-type organic semiconductor materials may be used in combination.

[0203] As described above, hydrogen in the material of the present invention may be deuterium. That is, in addition to hydrogen on the aromatic ring in the general formula (1) or the general formulas (2) to (8), part or all of the hydrogen in the substituent may be deuterium.

[0204] Furthermore, part or all of the hydrogen contained in the compound used as the N-type organic semiconductor material and the P-type organic semiconductor material may be deuterium.

[0205] The film-forming method of each layer when producing the imaging photoelectric conversion element of the present invention is not particularly limited, and the element can be produced by either a dry process or a wet process.

[0206] The organic layer containing the photoelectric conversion element material of the present invention may be formed into a plurality of layers as necessary.

[0207] Example

[0208] Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

[0209] Calculation Example

[0210] Calculation of HOMO and LUMO

[0211] The HOMO, LUMO, and energy difference between HOMO and LUMO of the compound A4, compound C13, compound D61, compound E42, compound E45, compound E58, compound E126, compound F42, and compound F125 were calculated. Furthermore, the calculation was performed using a calculation based on density functional theory (DFT: Density Functional Theory), using Gaussian as a calculation program, and by a structure optimization calculation based on density functional theory B3LYP / 6-31G (d). The results are shown in Table 1. It can be said that the photoelectric conversion element materials of the present invention all have better HOMO and LUMO values.

[0212] The HOMO, LUMO, and energy difference between HOMO and LUMO of H1, H2, and H3 as comparative compounds were calculated by the same method.

[0213] [Chemistry 55]

[0214]

[0215] [Table 1]

[0216] Compound HOMO[eV] LUMO[eV] Energy difference [eV] A4 -4.9 -0.7 4.2 C13 -4.8 -1.1 3.7 D61 -4.2 -1.0 3.2 E42 -4.4 -1.1 3.3 E45 -4.5 -1.0 3.5 E58 -4.6 -1.2 3.3 E126 -4.5 -1.2 3.3 F42 -4.7 -1.1 3.7 F125 -4.9 -1.2 3.7 H1 -5.3 -1.9 3.4 H2 -5.0 -0.9 4.1 H3 -5.1 -0.8 4.2

[0217] The following is a synthesis example of compound E42 as a representative example. Other compounds were synthesized by similar methods.

[0218] Synthesis Example 1 (Synthesis of Intermediate R3)

[0219] [Chemistry 56]

[0220]

[0221] R1 (19.0 mmol), R2 (19.9 mmol), copper iodide (0.4 mmol), tripotassium phosphate (56.9 mmol) were placed in a 500 ml three-necked flask that had been denitrogenated. 70 ml of dehydrated dioxane was added thereto, and the mixture was stirred at 120°C for 3 hours. After cooling to room temperature, the inorganic matter was removed by filtration, 200 ml of water and 200 ml of dichloromethane were added to the filtrate, and the mixture was transferred to a separatory funnel and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 200 ml of water, and the obtained organic layer was dehydrated with magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by column chromatography to obtain R3 (light yellow solid). Yield: 7.5 g, yield: 81.3%.

[0222] Synthesis Example 2 (Synthesis of E42)

[0223] [Chemistry 57]

[0224]

[0225] In a 300 ml three-necked flask that has been denitrogenated, R3 (10.3 mmol), R4 (13.3 mmol), tri-dibenzylideneacetone dipalladium (0.5 mmol), tri-tert-butylphosphine (2.1 mmol), sodium tert-butoxide (30.8 mmol), and 50 ml of dehydrated xylene synthesized in Synthesis Example 1 were placed, and stirred at 120°C for 2 hours. After cooling to room temperature, the inorganic matter was removed by filtration, and 200 ml of water and 200 ml of dichloromethane were added to the filtrate, and the filtrate was transferred to a separatory funnel and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 200 ml of water, and the obtained organic layer was dehydrated with magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by column chromatography to obtain E42 (light yellow solid). Yield: 4.2 g, yield: 69.4%. The obtained solid was evaluated by the XRD method, but no peak was detected, and thus it was found that the present compound was amorphous.

[0226] Physical property evaluation example

[0227] Compound E42 was deposited as an organic layer by vacuum deposition at a film thickness of about 3 μm on a glass substrate on which a transparent electrode including ITO with a film thickness of 110 nm was formed. Subsequently, a charge mobility measurement was performed by the time-of-flight method using an element formed with aluminum (Al) with a thickness of 70 nm as an electrode. The result showed that the hole mobility was 1.4×10 - 4 cm 2 / Vs.

[0228] The hole mobility was evaluated in the same manner except that compound E42 was replaced with A04, C13, E45, E126, F125, H1, H2, or H3. The results are shown in Table 2.

[0229] [Table 2]

[0230] Compound <![CDATA[Hole mobility [cm 2 / Vs]]]> A04 <![CDATA[5.9×10 -4 ]]> C13 <![CDATA[7.7×10 -5 ]]> E42 <![CDATA[1.4×10 -4 ]]> E45 <![CDATA[1.0×10 -4 ]]> E126 <![CDATA[1.9×10 -4 ]]> F125 <![CDATA[2.3×10 -4 ]]> H1 <![CDATA[4.0×10 -5 ]]> H2 <![CDATA[3.0×10 -5 ]]> H3 <![CDATA[1.0×10 -4 ]]>

[0231] Example 1

[0232] On an electrode including 70 nm thick ITO formed on a glass substrate, a vacuum of 4.0×10 -5 Pa deposited compound E42 with a thickness of 10nm as an electron blocking layer. Then, as a photoelectric conversion layer, 2Ph-BTBT, F6-SubPc-OC6F5, and fullerene (C60) were co-deposited at a deposition rate ratio of 4:4:2 to form a 200nm film. Next, dpy-NDI was deposited at a thickness of 10nm to form a hole blocking layer. Finally, aluminum was deposited at a thickness of 70nm as an electrode to make a photoelectric conversion element. When a voltage of 2.6V was applied using ITO and aluminum as electrodes, the current in the dark (dark current) was 5.1×10 -10 A / cm 2 In addition, when a voltage of 2.6 V was applied and the ITO electrode side was irradiated with light from a height of 10 cm by an LED with a wavelength of 500 nm and 1.6 μW, the current (bright current) was 3.7×10 -7 A / cm 2 The light-dark ratio when 2.6V voltage is applied is 7.3×10 2 These results are shown in Table 3.

[0233] Embodiment 2 to Embodiment 6

[0234] A photoelectric conversion element was prepared in the same manner as in Example 1 except that the compound shown in Table 3 was used as the electron blocking layer.

[0235] Comparative Examples 1 to 3

[0236] A photoelectric conversion element was prepared in the same manner as in Example 1 except that the compound shown in Table 3 was used as the electron blocking layer.

[0237] Table 3 shows the results of Examples 1 to 6 and Comparative Examples 1 to 3.

[0238] The compounds used in Examples and Comparative Examples are shown below.

[0239] [Chemistry 58]

[0240]

[0241] [Table 3]

[0242]

[0243] Description of symbols

[0244] 1: Electrode

[0245] 2: Hole blocking layer

[0246] 3: Photoelectric conversion layer

[0247] 4: Electron blocking layer

[0248] 5: Electrode

[0249] 6: Substrate

Claims

1. A photoelectric conversion element material, characterized in that: It comprises a compound represented by the following general formula (1), [Chemistry 1] In the general formula (1), Ar 1 ~Ar 3 Each of them independently represents deuterium, cyano, halogen, nitro, alkyl having 1 to 20 carbon atoms, aralkyl having 7 to 38 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, acyl having 2 to 20 carbon atoms, acyloxy having 2 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkoxycarbonyl having 2 to 20 carbon atoms, alkoxycarbonyloxy having 2 to 20 carbon atoms, alkylsulfonyl having 1 to 20 carbon atoms, dialkylamino having 2 to 20 carbon atoms, substituted or unsubstituted alkylarylamino having 7 to 28 carbon atoms, a substituted or unsubstituted diarylamine group having 12 to 36 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 12 to 36 carbon atoms, a substituted or unsubstituted diheteroarylamine group having 12 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group in which 2 to 10 aromatic hydrocarbon groups and aromatic heterocyclic groups are linked to each other, Ar 1 ~Ar 3 At least one of the following general formulas (2) to (8) is represented by any one of the following general formulas; and in Ar 1 ~Ar 3 In the case of a group having a hydrogen atom, the hydrogen atom may be substituted by deuterium or halogen; X represents C(Ar 4 Ar 5 ), NAr 6 , O, or S; a, and b represent the number of substitutions, and each independently represents an integer from 0 to 4; [Chemistry 2] [Chemistry 3] In general formulae (2) to (8), * represents the bonding point with general formula (1), L 1 and L 2 Each independently represents a direct bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two or three of these aromatic rings are linked; Ar 4 ~Ar 12 Separately with Ar 1 ~Ar 3 The narrator is the same as in Ar 4 ~Ar 12 When it represents a linked aromatic group, it represents a substituted or unsubstituted linked aromatic group in which two to three aromatic rings are linked; Ar 4 ,Ar 5 Can bond with each other to form a ring structure; c to f represent the number of substitutions, c, e, and f each independently represent an integer of 0 to 3, and d represents an integer of 0 to 2.

2. The photoelectric conversion element material according to claim 1, wherein the general formula (1) is represented by any one of the following general formulas (9) to (12): [Chemistry 4] In general formulas (9) to (12), Ar 1 ~Ar 6 , and a, b are the same as those described in the general formula (1). 3 . The photoelectric conversion element material according to claim 2 , wherein the general formula (1) is represented by any one of the general formula (11) and the general formula (12).

4. The photoelectric conversion element material according to claim 1, wherein Ar in the general formula (1) 1 ~Ar 3 At least one of the above-mentioned general formula (2), general formula (3), general formula (5), general formula (7), and general formula (8) is represented by any one of the general formulas (2), (3), (5), (7), and (8).

5. The photoelectric conversion element material according to claim 1, wherein Ar in the general formula (1) 1 It is represented by any one of the general formula (2), general formula (3), general formula (5), general formula (7), and general formula (8).

6. The photoelectric conversion element material for imaging according to claim 1, wherein L 1 For a single key.

7. The material for a photoelectric conversion element for imaging according to claim 1, wherein the energy level of the highest occupied molecular orbital (HOMO) obtained by structure optimization calculation based on density functional calculation B3LYP / 6-31G(d) is -4.0 eV or less. 8 . The material for an imaging photoelectric conversion element according to claim 1 , wherein the energy level of the lowest unoccupied molecular orbital (LUMO) obtained by the structural optimization calculation is −2.5 eV or more.

9. The imaging photoelectric conversion element material according to claim 1, having a 1×10 -6 cm 2 / Vs and above hole mobility. 10 . The imaging photoelectric conversion element material according to claim 1 , which is amorphous. 11 . The material for an imaging photoelectric conversion element according to claim 1 , which is used as a hole transport material of an imaging photoelectric conversion element.

12. A photoelectric conversion element for imaging, comprising a photoelectric conversion layer and an electron blocking layer between two electrodes, wherein at least one of the photoelectric conversion layer and the electron blocking layer comprises the material for the photoelectric conversion element for imaging as described in any one of claims 1 to 11. 13 . The imaging photoelectric conversion element according to claim 12 , wherein the electron blocking layer contains the imaging photoelectric conversion element material according to claim 1 . 14 . The imaging photoelectric conversion element according to claim 12 , wherein the photoelectric conversion layer contains an electron transporting material. 15 . The imaging photoelectric conversion element according to claim 12 , wherein the electron blocking layer contains the photoelectric conversion element material according to claim 1 , and the photoelectric conversion layer contains a fullerene derivative.

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