Compounds and solar cells using them

Abstract

Compounds that can be used as hole transport materials for perovskite solar cells are not well known. A new compound is proposed as a compound capable of forming a hole transport layer. 【Solution means】 It is a compound represented by the general formula (1). [In the general formula (1), X is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 carbon atoms, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, an alkynyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 9 carbon atoms, etc., and may be substituted with a substituent.]

Description

[Technical Field]

[0001] This invention relates to a novel compound that can be used in organic solar cells such as dye-sensitized solar cells and perovskite solar cells, and to a solar cell using the same. [Background technology]

[0002] Most solar cells currently in practical use are silicon-based or compound-based. While these solar cells offer high durability and high energy conversion efficiency, they have drawbacks such as high raw material costs and manufacturing costs, and in the case of silicon-based solar cells, the thick silicon and lack of panel flexibility limit their installation locations.

[0003] Therefore, in 2009, the first lead halide-based perovskite solar cell was developed (see Non-Patent Document 1). Solar cells based on such organic thin-film materials are excellent in terms of resource conservation and can be manufactured over large areas, making them superior in terms of manufacturing cost.

[0004] Perovskite solar cells use perovskite crystals, such as methylammonium lead iodide (NH3CH3PbI3; MAPI), as the photoelectric conversion layer for sunlight. Perovskite solar cells have an electron transport layer in their photoelectric conversion layer that carries electrons generated by light to the anode and a hole transport layer that transports holes generated by light to the cathode, and the electron transport layer and hole transport layer are joined to the photoelectric conversion layer.

[0005] For example, in a solar cell having the structure of a transparent electrode (FTO) / electron transport layer (dense TiO2) / perovskite photoconversion layer (meso-TiO2-MAPI / MAPI) / hole transport layer (Spiro-OMeTAD) / electrode (Au), when light is incident from the transparent electrode side, electrons and holes are generated in the perovskite photoconversion layer. Electrons are transported to the transparent electrode (anode) through the electron transport layer, and holes are transported to the electrode (cathode) through the hole transport layer. Solar cells with this structure are nip-type (forward-direction) photoconversion elements, similar to solid-state dye-sensitized solar cells.

[0006] On the other hand, for example, transparent electrode (FTO) / hole transport layer (PEDOT:PSS) / perovskite photoelectric conversion layer (MAPI) 3-x Cl x ) / electron transport layer (PCBM / TiO x Solar cells are known to have a structure consisting of a transparent electrode (cathode) such as an electrode (Al), a hole transport layer, a perovskite photoelectric conversion layer, an electron transport layer, and an electrode (anode). Solar cells with such a structure are pin-type (reverse-direction) photoelectric conversion elements.

[0007] Because the perovskite crystals described above can be easily fabricated, it is expected that manufacturing costs can be reduced compared to conventional solar cells. Furthermore, because flexible and lightweight solar cells can be realized, they are expected to be able to be installed in a variety of locations. Perovskite solar cells have attracted attention because they have been reported to have high photoelectric conversion efficiencies (24.4%) and high voltage outputs of 1.15V or higher, comparable to those of silicon-based and compound-based solar cells (see Non-Patent Literature 2). [Prior art documents] [Patent Documents]

[0008] [Non-Patent Document 1] Kojima, A. et al., J. Am. Chem. Soc. 2009, 131, 6050-6051 [Non-Patent Document 2] M.A.Green, et al., Prog.Photovolt. 2023, 31, 651-663 [Non-Patent Document 3] A, Magomedov. et al., al Adv. Energy Mater. 2018, 8, 1801892 [Non-Patent Document 4] A, Al-Ashouri Energy Environ. Sci., 2019, 12, 3356-3369 [Summary of the Invention] [Problems to be Solved by the Invention]

[0009] However, the reported photoelectric conversion efficiency and voltage output mentioned above are considered to be the values in the initial short time. That is, Non-Patent Document 2 does not mention anything about the durability (light resistance, heat resistance, solvent resistance, etc.) of perovskite solar cells. In order to improve the durability of perovskite solar cells, it is considered necessary to examine each of the light absorption layer, electron transport layer, and hole transport layer that constitute it.

[0010] As described above, Spiro-OMeTAD is known as a hole transport material for perovskite solar cells. When Spiro-OMeTAD is used as the hole transport layer, for example, dopants such as lithium bis(trifluoromethane)sulfonimide (LiTFSI) and / or 4-tert-butylpyridine (4-tert-butyl pyridine; TBP) are added. Pure Spiro-OMeTAD has relatively low hole mobility and conductivity, so the addition of these dopants adjusts the electronic properties of Spiro-OMeTAD, but has the disadvantage of promoting the degradation of Spiro-OMeTAD.

[0011] [Chemical Formula]

[0012] In recent years, hole transport materials consisting of carbazole derivatives containing phosphonic acid groups have been reported (see Non-Patent Document 3). Such compounds are generally used in pin-type photovoltaic devices, forming self-assembled monolayers (SAMs) on transparent indium tin (ITO) electrodes and exhibiting hole transport capabilities. Solar cells using SAM-based hole transport materials have been reported to achieve conversion efficiencies exceeding 20% ​​even without the use of dopants (see Non-Patent Document 4), and furthermore, they can be manufactured inexpensively with less material usage. However, Non-Patent Documents 3 and 4 do not mention the durability of the hole transport materials.

[0013] [ka]

[0014] As mentioned above, the types of compounds that can be used as hole transport materials to form the hole transport layer in perovskite solar cells are limited. Ideally, compounds that can form a hole transport layer with excellent photoelectric conversion efficiency and durability (light resistance, heat resistance, solvent resistance, etc.) are desired. To further develop perovskite solar cells, it is necessary to increase the types of compounds that can form the hole transport layer, and there is a need to propose new compounds. The chemical structure and properties of such compounds are of academic and industrial interest. [Means for solving the problem]

[0015] In view of the above problems, the present inventors conducted extensive research and, as a result, surprisingly discovered that compounds in which silatran groups are linked to a cyclic indole trimer skeleton and an indolocarbazole skeleton can be used as hole transport materials. Furthermore, they found that these compounds can form a hole transport layer with excellent photoelectric conversion efficiency and durability.

[0016] More specifically, this specification relates to the following [1] to [7]. [1] A compound represented by any one of the following general formulas (1), (2), (3), (4), (5), (6) and (7). [Chemical formula] [In general formula (1), X 1 ~X 3 are each independently a hydrogen atom or the following structural formula (A). However, at least one of X 1 ~X 3 represents the following structural formula (A). [Chemical formula] (In structural formula (A), L 1 is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with a substituent, and * represents a bond.) Also, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8 , R 9 , R 10 , R 11 and R 12 Two adjacent elements within the ring may be joined together to form a ring. [ka] [In general formula (2), X 4 ~X 6 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 4 ~X 6 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1(wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 and R 24 These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 and R 24 Two adjacent elements within the ring may be joined together to form a ring. [ka] [In general formula (3), X 7 ~X 8 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 7 ~X 8 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R 2 5 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 25 and R 26 and R 27 and R 28 and R 29 and R 30 and R 31 and R 32 and R 33 and R 34 Any two adjacent ones among them may be bonded to each other to form a ring.] [Chemical formula] [In general formula (4), X 9 ~X 10 are each independently a hydrogen atom or the following structural formula (A). However, at least one of X 9 ~X 10 represents the following structural formula (A). [Chemical formula] (In structural formula (A), L 1 is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with a substituent, and * represents a bond.) Also, R 35 and R 36 and R 37 and R 38 and R 39 and R 40 and R 41 and R 42 and R 43 and R 44These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 and R 44 Two adjacent elements within the ring may be joined together to form a ring. [ka] [In general formula (5), X 11 ~X 12 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 11 ~X 12 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1(wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R and R 54 These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R and R 54 Two adjacent elements within the ring may be joined together to form a ring. [ka] [In general formula (6), X13 ~X 14 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 13 ~X 14 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 and R 64 These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 55 , R 56 , R 57 , R 58 , R 59 , R60 , R 61 , R 62 , R 63 and R 64 Two adjacent elements within the ring may be joined together to form a ring. [ka] [In general formula (7), X 15 ~X 16 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 15 ~X 16 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R 65 , R 66 , R 67 , R 68 , R 69 , R 70 , R 71 , R 72 , R 63 and R 74These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. 65 , R 66 , R 67 , R 68 , R 69 , R 70 , R 71 , R 72 , R 63 and R 74 Two adjacent elements within the ring may be joined together to form a ring. [2] L of the above structural formula (A) 1 However, the compounds described in [1] have the following structural formula (i) or (ii). [ka] (In structural formula (i), a is an integer between 1 and 8, and * indicates a bond.) [ka] (In structural formula (ii), * indicates a bond.) A hole transport material comprising the compound described in [3] [1] or [2]. [4] A photoelectric element comprising a first electrode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a second electrode in this order, wherein the hole transport layer contains the compound described in [1] or [2]. [5] A photoelectric conversion element described in [4], which has a pin-type structure. [6] The photoelectric element according to [4] or [5], wherein the photoelectric conversion layer is a perovskite layer. A solar cell comprising a photoelectric conversion element described in any one of [7], [4], to [6]. [Effects of the Invention]

[0017] Compounds in which silatran groups are linked to a cyclic indole trimer skeleton or an indolocarbazole skeleton can be used as hole transport materials for photoelectric conversion elements. Furthermore, these compounds can form a hole transport layer that is highly durable while maintaining sufficient photoelectric conversion efficiency. [Brief explanation of the drawing]

[0018] [Figure 1] Figure 1 is a schematic cross-sectional view illustrating an example of the configuration of a photoelectric conversion element in an embodiment of the present invention. [Figure 2] Figure 2 shows a compound according to an embodiment of the present invention. [Modes for carrying out the invention]

[0019] The present invention will be described in further detail. However, the present invention is not limited to the following description.

[0020] The compounds of the embodiments of the present invention are represented by any one of the following general formulas: (1), (2), (3), (4), (5), (6), and (7). [ka] [In general formula (1), X 1 ~X 3 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 1 ~X3 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0021] In general formula (1), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0022] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, alkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0023] In this specification, "ring-forming carbon number" refers to the number of carbon atoms that form an aromatic ring, such as an aryl group, arylene group, heteroaryl group, and heteroarylene group, and does not include the number of carbon atoms of substituents on the aromatic ring. For example, the ring-forming carbon number of a phenyl group, phenylene group, 4-methylphenyl group, 2,4-dimethylphenyl group, and 2,3-dimethylphenylene group is 6.

[0024] Also, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0025] In general formula (1), R 1 ~R 12The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. Examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, t-pentyl, hexyl, heptyl, octyl, nonyl, isononyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups.

[0026] In general formula (1), R 1 ~R 12 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms, such as ethynyl(vinyl) group, 1-propenyl group, 2-propenyl(allyl) group, 1-butenyl group, 1-pentenyl group, 3-methyl-1-butenyl group, 1-hexenyl group, isopropenyl group, 1-heptenyl group, 1-octenyl group, etc.

[0027] In general formula (1), R 1 ~R 12 The term "alkynyl group having 1 to 8 carbon atoms" refers to linear or branched alkynyl groups having 1 to 8 carbon atoms, such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 1-pentynyl group, 2-pentynyl group, 1-hexynyl group, 1-heptynyl group, and 1-octinyl group.

[0028] In general formula (1), R 1 ~R 12 Examples of "alkoxy groups having 1 to 8 carbon atoms" include methoxy groups, ethoxy groups, propoxy groups, n-butoxy groups, n-pentyloxy groups, n-hexyloxy groups, heptyloxy groups, and octyloxy groups.

[0029] In general formula (1), R 1 ~R 12Examples of "alkoxycarbonyl groups having 1 to 9 carbon atoms" include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, heptyloxycarbonyl group, and octyloxycarbonyl group.

[0030] In general formula (1), R 1 ~R 12 The "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by ∫ includes methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, isopropoxycarbonylamino group, butoxycarbonylamino group, pentyloxycarbonylamino group, hexyloxycarbonylamino group, heptyloxycarbonylamino group, and octyloxycarbonylamino group.

[0031] In general formula (1), R 1 ~R 12 Examples of "acyl groups with 1 to 9 carbon atoms" represented by this formula include the formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, pivaloyl group, and benzoyl group.

[0032] In general formula (1), R 1 ~R 12 Examples of "acylamino groups with 1 to 9 carbon atoms" include formylamino group, acetylamino group, propionylamino group, butyrylamino group, isobutyrylamino group, valerylamino group, isovalerylamino group, pivaloylamino group, and benzoylamino group.

[0033] In general formula (1), R 1 ~R 12 Examples of "acyloxy groups with 1 to 9 carbon atoms" include formyloxy group, acetyloxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, valeryloxy group, isovaleryloxy group, pivaloyloxy group, and benzoyloxy group.

[0034] In general formula (1), R 1 ~R 12 Examples of the "alkylthio group having 1 to 8 carbon atoms" represented by include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, s-butylthio group, t-butylthio group, pentylthio group, isopentylthio group, t-pentylthio group, hexylthio group, heptylthio group, octylthio group, nonylthio group, isononylthio group, decylthio group, cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group, and cyclooctylthio group.

[0035] In general formula (1), R 1 ~R 12 Examples of "alkylamino groups having 1 to 8 carbon atoms" include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, s-butylamino group, t-butylamino group, pentylamino group, isopentylamino group, t-pentylamino group, hexylamino group, heptylamino group, and octylamino group.

[0036] In general formula (1), R 1 ~R 12 Examples of "dialkylamino groups having 2 to 16 carbon atoms" include dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, diisobutylamino group, di-s-butylamino group, di-t-butylamino group, dipentylamino group, diisopentylamino group, di-t-pentylamino group, dihexylamino group, diheptylamino group, dioctylamino group, and so on.

[0037] In general formula (1), R 1 ~R 12 Examples of "aminoalkyl groups having 1 to 8 carbon atoms" include aminomethyl, aminoethyl, aminopropyl, aminobutyl, aminopentyl, aminohexyl, aminoheptyl, and aminooctyl groups.

[0038] In general formula (1), R 1 ~R 12 Examples of "thioalkyl groups having 1 to 8 carbon atoms" include thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl, thioheptyl, and thiooctyl groups.

[0039] In general formula (1), R 1 ~R 12 The "aryl group with 6 to 18 ring-forming carbon atoms" represented by can be, for example, a phenyl group, naphthyl group, biphenyl group, terphenyl group, anthryl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, triphenyl group, etc. It may also have substituents, and if substituents are present, examples of substituents can be halogen atoms such as fluorine, chlorine, bromine, and iodine atoms, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, a carbonalkoxycarbonylamino group, an acyl group, an acylamino group, an acyloxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an aminoalkyl group, or a thioalkyl group.

[0040] In general formula (1), R 1 ~R 12The "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by can be, for example, a phenyloxy group, naphthyloxy group, biphenyloxy group, terphenyloxy group, anthryloxy group, phenanthryloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, triphenyloxy group, etc. They may also have substituents, and examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, a carbonalkoxycarbonylamino group, an acyl group, an acylamino group, an acyloxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an aminoalkyl group, and a thioalkyl group.

[0041] In general formula (1), R 1 ~R 12 The "arylthio group with 6 to 18 ring-forming carbon atoms" represented by can be, for example, a phenylthio group, naphthylthio group, biphenylthio group, terphenylthio group, anthrylthio group, phenanthrylthio group, fluorenylthio group, indenylthio group, pyrenylthio group, triphenylthio group, etc. It may also have substituents, and examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, a carbonalkoxycarbonylamino group, an acyl group, an acylamino group, an acyloxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an aminoalkyl group, and a thioalkyl group.

[0042] In general formula (1), R 1 ~R 12The "arylamino group with 6 to 18 ring-forming carbon atoms" represented by can be, for example, a phenylamino group, naphthylamino group, biphenylamino group, terphenylamino group, anthrylamino group, phenanthrylamino group, fluorenylamino group, indenylamino group, pyrenylamino group, triphenylamino group, etc. It may also have substituents, and examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, a carbon alkoxycarbonylamino group, an acyl group, an acylamino group, an acyloxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an aminoalkyl group, and a thioalkyl group.

[0043] In general formula (1), R 1 ~R 12 The "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by can be, for example, a diphenylamino group, a dinaphthylamino group, a dibiphenylamino group, a diterphenyl amino group, a diantryl amino group, a diphenanthrylamino group, a difluorenylamino group, a diindenylamino group, a dipyrenylamino group, a ditriphenylamino group, and a ditriphenylamino group. They may also have substituents, and examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, a carbon alkoxycarbonylamino group, an acyl group, an acylamino group, an acyloxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an aminoalkyl group, and a thioalkyl group.

[0044] In general formula (1), R 1 ~R 12Examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by include pyrrolidyl group, pyridyl group, furanyl group, thiophenyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, pyridadinyl group, triazinyl group, naphthilidinyl group, sinnolinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, benzocarbazolyl group, carbolinyl group, indrocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, dihydroindenocarbazolyl group, benzoquinolinyl group, acridinyl group, benzimidazolyl group, imidazopyridyl group, benzoxazolyl group, benzothiazolyl group, and phenanthrolinyl group. The molecule may also have substituents. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl groups, nitro groups, sulfonyl groups, cyano groups, amino groups, sulfonylamino groups, thio groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, alkoxycarbonyl groups, carbonalkoxycarbonylamino groups, acyl groups, acylamino groups, acyloxy groups, alkylthio groups, alkylamino groups, dialkylamino groups, aminoalkyl groups, and thioalkyl groups.

[0045] In general formula (1), R 1 ~R 12 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields compound (1) for which the present invention is intended, and may or may not form an aromatic ring.

[0046] [ka] [In general formula (2), X 4 ~X 6 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 4 ~X 6 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0047] In general formula (2), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0048] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, carbonalkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0049] Also, R 13 , R 14 , R 15 , R 16 , R 17, R 18 , R 19 , R 20 , R 21 , R 22 , R 23 and R 24 These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0050] In general formula (2), R 13 ~R 24 The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkyl groups with 1 to 10 carbon atoms".

[0051] In general formula (2), R 13 ~R 24 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkenyl groups with 1 to 8 carbon atoms".

[0052] In general formula (2), R 13 ~R 24 The term "alkynyl group having 1 to 8 carbon atoms" refers to a linear or branched alkynyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkynyl groups with 1 to 8 carbon atoms".

[0053] In general formula (2), R 13 ~R 24 For specific examples of the "alkoxy group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxy groups with 1 to 8 carbon atoms".

[0054] In general formula (2), R 13 ~R 24 For specific examples of the "alkoxycarbonyl group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonyl groups with 1 to 8 carbon atoms".

[0055] In general formula (2), R 13 ~R 24 For specific examples of the "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonylamino group having 1 to 8 carbon atoms".

[0056] In general formula (2), R 13 ~R 24 For specific examples of the "acyl group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyl groups with 1 to 9 carbon atoms".

[0057] In general formula (2), R 13 ~R 24 For specific examples of the "acylamino group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12You may also refer to the example of "acylamino group with 1 to 9 carbon atoms".

[0058] In general formula (2), R 13 ~R 24 For specific examples of the "acyloxy group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyloxy groups with 1 to 9 carbon atoms".

[0059] In general formula (2), R 13 ~R 24 For specific examples of the "alkylthio group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylthio groups with 1 to 8 carbon atoms".

[0060] In general formula (2), R 13 ~R 24 For specific examples of the "alkylamino group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylamino groups with 1 to 8 carbon atoms".

[0061] In general formula (2), R 13 ~R 24 For specific examples of the "dialkylamino group with 2 to 16 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "dialkylamino group with 2 to 16 carbon atoms".

[0062] In general formula (2), R 13 ~R 24 For specific examples of the "aminoalkyl group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aminoalkyl groups with 1 to 8 carbon atoms".

[0063] In general formula (2), R 13 ~R 24 For specific examples of the "thioalkyl group with 1 to 8 carbon atoms" represented by the above R 1 ~R12 You may also refer to the example of "thioalkyl groups with 1 to 8 carbon atoms".

[0064] In general formula (2), R 13 ~R 24 For specific examples of the "aryl group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryl groups with 6 to 18 carbon atoms forming a ring".

[0065] In general formula (2), R 13 ~R 24 For specific examples of the "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryloxy groups with 6 to 18 carbon atoms forming a ring".

[0066] In general formula (2), R 13 ~R 24 For specific examples of the "arylthio group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylthio groups with 6 to 18 ring-forming carbon atoms".

[0067] In general formula (2), R 13 ~R 24 For specific examples of the "arylamino group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylamino groups with 6 to 18 ring-forming carbon atoms".

[0068] In general formula (2), R 13 ~R 24 For specific examples of the "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "diarylamino groups with 12 to 36 ring-forming carbon atoms".

[0069] In general formula (2), R 13 ~R 24For specific examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by the above R 1 ~R 12 You may also refer to the example of "heteroaryl groups with 5 to 18 carbon atoms forming a ring". In general formula (2), R 13 ~R 24 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields compound (2) for which the present invention is intended, and may or may not form an aromatic ring.

[0070] [ka] [In general formula (3), X 7 ~X 8 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 7 ~X 8 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0071] In general formula (3), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0072] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, carbonalkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0073] Also, R 2 5 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0074] In general formula (3), R 25 ~R 34 The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkyl groups with 1 to 10 carbon atoms".

[0075] In general formula (3), R 25 ~R 34 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkenyl groups with 1 to 8 carbon atoms".

[0076] In general formula (3), R 25 ~R 34The term "alkynyl group having 1 to 8 carbon atoms" refers to a linear or branched alkynyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkynyl groups with 1 to 8 carbon atoms".

[0077] In general formula (3), R 25 ~R 34 For specific examples of the "alkoxy group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxy groups with 1 to 8 carbon atoms".

[0078] In general formula (3), R 25 ~R 34 For specific examples of the "alkoxycarbonyl group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonyl groups with 1 to 8 carbon atoms".

[0079] In general formula (3), R 25 ~R 34 For specific examples of the "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonylamino group having 1 to 8 carbon atoms".

[0080] In general formula (3), R 25 ~R 34 For specific examples of the "acyl group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyl groups with 1 to 9 carbon atoms".

[0081] In general formula (3), R 25 ~R 34 For specific examples of the "acylamino group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acylamino group with 1 to 9 carbon atoms".

[0082] In general formula (3), R 25 ~R 34 For specific examples of the "acyloxy group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyloxy groups with 1 to 9 carbon atoms".

[0083] In general formula (3), R 25 ~R 34 For specific examples of the "alkylthio group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylthio groups with 1 to 8 carbon atoms".

[0084] In general formula (3), R 25 ~R 34 For specific examples of the "alkylamino group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylamino groups with 1 to 8 carbon atoms".

[0085] In general formula (3), R 25 ~R 34 For specific examples of the "dialkylamino group with 2 to 16 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "dialkylamino group with 2 to 16 carbon atoms".

[0086] In general formula (3), R 25 ~R 34 For specific examples of the "aminoalkyl group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aminoalkyl groups with 1 to 8 carbon atoms".

[0087] In general formula (3), R 25 ~R 34 For specific examples of the "thioalkyl group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "thioalkyl groups with 1 to 8 carbon atoms".

[0088] In general formula (3), R 25 ~R 34 For specific examples of the "aryl group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryl groups with 6 to 18 carbon atoms forming a ring".

[0089] In general formula (3), R 25 ~R 34 For specific examples of the "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryloxy groups with 6 to 18 carbon atoms forming a ring".

[0090] In general formula (3), R 25 ~R 34 For specific examples of the "arylthio group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylthio groups with 6 to 18 ring-forming carbon atoms".

[0091] In general formula (3), R 25 ~R 34 For specific examples of the "arylamino group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylamino groups with 6 to 18 ring-forming carbon atoms".

[0092] In general formula (3), R 25 ~R 34 For specific examples of the "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "diarylamino groups with 12 to 36 ring-forming carbon atoms".

[0093] In general formula (3), R 25 ~R 34 For specific examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by the above R 1 ~R 12You may also refer to the example of "heteroaryl groups with 5 to 18 carbon atoms forming a ring".

[0094] In general formula (3), R 2 5 ~R 34 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields compound (3) for which the present invention is intended, and may or may not form an aromatic ring.

[0095] [ka] [In general formula (4), X 9 ~X 10 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 9 ~X 10 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0096] In general formula (4), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0097] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, carbonalkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0098] Also, R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 and R 44These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0099] In general formula (4), R 35 ~R 44 The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkyl groups with 1 to 10 carbon atoms".

[0100] In general formula (4), R 35 ~R 44 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkenyl groups with 1 to 8 carbon atoms".

[0101] In general formula (4), R 35 ~R 44The term "alkynyl group having 1 to 8 carbon atoms" refers to a linear or branched alkynyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkynyl groups with 1 to 8 carbon atoms".

[0102] In general formula (4), R 35 ~R 44 For specific examples of the "alkoxy group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxy groups with 1 to 8 carbon atoms".

[0103] In general formula (4), R 35 ~R 44 For specific examples of the "alkoxycarbonyl group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonyl groups with 1 to 8 carbon atoms".

[0104] In general formula (4), R 35 ~R 44 For specific examples of the "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonylamino group having 1 to 8 carbon atoms".

[0105] In general formula (4), R 35 ~R 44 For specific examples of the "acyl group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyl groups with 1 to 9 carbon atoms".

[0106] In general formula (4), R 35 ~R 44 For specific examples of the "acylamino group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acylamino group with 1 to 9 carbon atoms".

[0107] In general formula (4), R 35 ~R 44 For specific examples of the "acyloxy group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyloxy groups with 1 to 9 carbon atoms".

[0108] In general formula (4), R 35 ~R 44 For specific examples of the "alkylthio group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylthio groups with 1 to 8 carbon atoms".

[0109] In general formula (4), R 35 ~R 44 For specific examples of the "alkylamino group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylamino groups with 1 to 8 carbon atoms".

[0110] In general formula (4), R 35 ~R 44 For specific examples of the "dialkylamino group with 2 to 16 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "dialkylamino group with 2 to 16 carbon atoms".

[0111] In general formula (4), R 35 ~R 44 For specific examples of the "aminoalkyl group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aminoalkyl groups with 1 to 8 carbon atoms".

[0112] In general formula (4), R 35 ~R 44 For specific examples of the "thioalkyl group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "thioalkyl groups with 1 to 8 carbon atoms".

[0113] In general formula (4), R 35 ~R 44 For specific examples of the "aryl group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryl groups with 6 to 18 carbon atoms forming a ring".

[0114] In general formula (4), R 35 ~R 44 For specific examples of the "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryloxy groups with 6 to 18 carbon atoms forming a ring".

[0115] In general formula (4), R 35 ~R 44 For specific examples of the "arylthio group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylthio groups with 6 to 18 ring-forming carbon atoms".

[0116] In general formula (4), R 35 ~R 44 For specific examples of the "arylamino group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylamino groups with 6 to 18 ring-forming carbon atoms".

[0117] In general formula (4), R 35 ~R 44 For specific examples of the "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "diarylamino groups with 12 to 36 ring-forming carbon atoms".

[0118] In general formula (4), R 35 ~R 44 For specific examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by the above R 1 ~R 12You may also refer to the example of "heteroaryl groups with 5 to 18 carbon atoms forming a ring".

[0119] In general formula (4), R 35 ~R 44 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields the compound (4) targeted by the present invention, and may or may not form an aromatic ring.

[0120] [ka] [In general formula (5), X 11 ~X 12 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 11 ~X 12 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0121] In general formula (5), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0122] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, carbonalkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0123] Also, R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0124] In general formula (5), R 45 ~R 54 The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkyl groups with 1 to 10 carbon atoms".

[0125] In general formula (5), R 45 ~R 54 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkenyl groups with 1 to 8 carbon atoms".

[0126] In general formula (5), R 45 ~R 54The term "alkynyl group having 1 to 8 carbon atoms" refers to a linear or branched alkynyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkynyl groups with 1 to 8 carbon atoms".

[0127] In general formula (5), R 45 ~R 54 For specific examples of the "alkoxy group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxy groups with 1 to 8 carbon atoms".

[0128] In general formula (5), R 45 ~R 54 For specific examples of the "alkoxycarbonyl group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonyl groups with 1 to 8 carbon atoms".

[0129] In general formula (5), R 45 ~R 54 For specific examples of the "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonylamino group having 1 to 8 carbon atoms".

[0130] In general formula (5), R 45 ~R 54 For specific examples of the "acyl group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyl groups with 1 to 9 carbon atoms".

[0131] In general formula (5), R 45 ~R 54 For specific examples of the "acylamino group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acylamino group with 1 to 9 carbon atoms".

[0132] In general formula (5), R 45 ~R 54 For specific examples of the "acyloxy group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyloxy groups with 1 to 9 carbon atoms".

[0133] In general formula (5), R 45 ~R 54 For specific examples of the "alkylthio group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylthio groups with 1 to 8 carbon atoms".

[0134] In general formula (5), R 45 ~R 54 For specific examples of the "alkylamino group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylamino groups with 1 to 8 carbon atoms".

[0135] In general formula (5), R 45 ~R 54 For specific examples of the "dialkylamino group with 2 to 16 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "dialkylamino group with 2 to 16 carbon atoms".

[0136] In general formula (5), R 45 ~R 54 For specific examples of the "aminoalkyl group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aminoalkyl groups with 1 to 8 carbon atoms".

[0137] In general formula (5), R 45 ~R 54 For specific examples of the "thioalkyl group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "thioalkyl groups with 1 to 8 carbon atoms".

[0138] In general formula (5), R 45 ~R 54 For specific examples of the "aryl group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryl groups with 6 to 18 carbon atoms forming a ring".

[0139] In general formula (5), R 45 ~R 54 For specific examples of the "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryloxy groups with 6 to 18 carbon atoms forming a ring".

[0140] In general formula (5), R 45 ~R 54 For specific examples of the "arylthio group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylthio groups with 6 to 18 ring-forming carbon atoms".

[0141] In general formula (5), R 45 ~R 54 For specific examples of the "arylamino group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylamino groups with 6 to 18 ring-forming carbon atoms".

[0142] In general formula (5), R 45 ~R 54 For specific examples of the "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "diarylamino groups with 12 to 36 ring-forming carbon atoms".

[0143] In general formula (5), R 45 ~R 54 For specific examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by the above R 1 ~R 12You may also refer to the example of "heteroaryl groups with 5 to 18 carbon atoms forming a ring".

[0144] In general formula (5), R 45 ~R 54 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields the compound (5) targeted by the present invention, and may or may not form an aromatic ring.

[0145] [ka] [In general formula (6), X 13 ~X 14 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 13 ~X 14 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0146] In general formula (6), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0147] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, carbonalkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0148] Also, R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 and R 64These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0149] In general formula (6), R 55 ~R 64 The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkyl groups with 1 to 10 carbon atoms".

[0150] In general formula (6), R 55 ~R 64 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkenyl groups with 1 to 8 carbon atoms".

[0151] In general formula (6), R 55 ~R 64The term "alkynyl group having 1 to 8 carbon atoms" refers to a linear or branched alkynyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkynyl groups with 1 to 8 carbon atoms".

[0152] In general formula (6), R 55 ~R 64 For specific examples of the "alkoxy group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxy groups with 1 to 8 carbon atoms".

[0153] In general formula (6), R 55 ~R 64 For specific examples of the "alkoxycarbonyl group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonyl groups with 1 to 8 carbon atoms".

[0154] In general formula (6), R 55 ~R 64 For specific examples of the "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonylamino group having 1 to 8 carbon atoms".

[0155] In general formula (6), R 55 ~R 64 For specific examples of the "acyl group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyl groups with 1 to 9 carbon atoms".

[0156] In general formula (6), R 55 ~R 64 For specific examples of the "acylamino group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acylamino group with 1 to 9 carbon atoms".

[0157] In general formula (6), R 55 ~R 64 For specific examples of the "acyloxy group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyloxy groups with 1 to 9 carbon atoms".

[0158] In general formula (6), R 55 ~R 64 For specific examples of the "alkylthio group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylthio groups with 1 to 8 carbon atoms".

[0159] In general formula (6), R 55 ~R 64 For specific examples of the "alkylamino group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylamino groups with 1 to 8 carbon atoms".

[0160] In general formula (6), R 55 ~R 64 For specific examples of the "dialkylamino group with 2 to 16 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "dialkylamino group with 2 to 16 carbon atoms".

[0161] In general formula (6), R 55 ~R 64 For specific examples of the "aminoalkyl group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aminoalkyl groups with 1 to 8 carbon atoms".

[0162] In general formula (6), R 55 ~R 64 For specific examples of the "thioalkyl group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "thioalkyl groups with 1 to 8 carbon atoms".

[0163] In general formula (6), R 55 ~R 64 For specific examples of the "aryl group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryl groups with 6 to 18 carbon atoms forming a ring".

[0164] In general formula (6), R 55 ~R 64 For specific examples of the "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryloxy groups with 6 to 18 carbon atoms forming a ring".

[0165] In general formula (6), R 55 ~R 64 For specific examples of the "arylthio group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylthio groups with 6 to 18 ring-forming carbon atoms".

[0166] In general formula (6), R 55 ~R 64 For specific examples of the "arylamino group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylamino groups with 6 to 18 ring-forming carbon atoms".

[0167] In general formula (6), R 55 ~R 64 For specific examples of the "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "diarylamino groups with 12 to 36 ring-forming carbon atoms".

[0168] In general formula (6), R 55 ~R 64 For specific examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by the above R 1 ~R 12You may also refer to the example of "heteroaryl groups with 5 to 18 carbon atoms forming a ring".

[0169] In general formula (6), R 55 ~R 64 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields the compound (6) targeted by the present invention, and may or may not form an aromatic ring.

[0170] [ka] [In general formula (7), X 15 ~X 16 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 15 ~X 16 At least one of them exhibits the following structural formula (A). [ka] (In structural formula (A), L 1 (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.)

[0171] In general formula (7), L 1 This refers to an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. "Alkylene group" refers to a linear or branched alkylene group having 1 to 8 carbon atoms, such as methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, s-butylene group, t-butylene group, n-pentylene group, isopentylene group, n-hexylene group, 2-ethylhexyl group, heptylene group, octylene group, etc. More preferably, a linear alkylene group having 1 to 8 carbon atoms is used, and most preferably, a linear alkylene group having 2 to 4 carbon atoms is used.

[0172] "Arylene group" refers to an arylene group having 6 to 18 ring-forming carbon atoms, which may have substituents. Examples include phenylene group, naphthylene group, biphenylene group, terphenylene group, anthrylene group, phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, and triphenylene group. Examples of substituents include halogen atoms such as fluorine, chlorine, bromine, and iodine, hydroxyl group, nitro group, sulfonyl group, cyano group, amino group, sulfonylamino group, thio group, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkoxycarbonyl group, carbonalkoxycarbonylamino group, acyl group, acylamino group, acyloxy group, alkylthio group, alkylamino group, dialkylamino group, aminoalkyl group, and thioalkyl group. More preferably, the arylene group is an unsubstituted phenylene group.

[0173] Also, R 65 , R 66 , R 67 , R 68 , R 69 , R 70 , R 71 , R 72 , R 73 and R 74These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents.

[0174] In general formula (7), R 65 ~R 74 The term "alkyl group having 1 to 10 carbon atoms" refers to a linear, branched, or cyclic alkyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkyl groups with 1 to 10 carbon atoms".

[0175] In general formula (7), R 65 ~R 74 The term "alkenyl group having 1 to 8 carbon atoms" refers to a linear or branched alkenyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkenyl groups with 1 to 8 carbon atoms".

[0176] In general formula (7), R 65 ~R 74The term "alkynyl group having 1 to 8 carbon atoms" refers to a linear or branched alkynyl group having 1 to 8 carbon atoms. For specific examples, see the above R 1 ~R 12 You may also refer to the example of "alkynyl groups with 1 to 8 carbon atoms".

[0177] In general formula (7), R 65 ~R 74 For specific examples of the "alkoxy group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxy groups with 1 to 8 carbon atoms".

[0178] In general formula (7), R 65 ~R 74 For specific examples of the "alkoxycarbonyl group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonyl groups with 1 to 8 carbon atoms".

[0179] In general formula (7), R 65 ~R 74 For specific examples of the "alkoxycarbonylamino group having 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkoxycarbonylamino group having 1 to 8 carbon atoms".

[0180] In general formula (7), R 65 ~R 74 For specific examples of the "acyl group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyl groups with 1 to 9 carbon atoms".

[0181] In general formula (7), R 65 ~R 74 For specific examples of the "acylamino group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acylamino group with 1 to 9 carbon atoms".

[0182] In general formula (7), R 65 ~R 74 For specific examples of the "acyloxy group with 1 to 9 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "acyloxy groups with 1 to 9 carbon atoms".

[0183] In general formula (7), R 65 ~R 74 For specific examples of the "alkylthio group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylthio groups with 1 to 8 carbon atoms".

[0184] In general formula (7), R 65 ~R 74 For specific examples of the "alkylamino group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "alkylamino groups with 1 to 8 carbon atoms".

[0185] In general formula (7), R 65 ~R 74 For specific examples of the "dialkylamino group with 2 to 16 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "dialkylamino group with 2 to 16 carbon atoms".

[0186] In general formula (7), R 65 ~R 74 For specific examples of the "aminoalkyl group having 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aminoalkyl groups with 1 to 8 carbon atoms".

[0187] In general formula (7), R 65 ~R 74 For specific examples of the "thioalkyl group with 1 to 8 carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "thioalkyl groups with 1 to 8 carbon atoms".

[0188] In general formula (7), R 65 ~R 74 For specific examples of the "aryl group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryl groups with 6 to 18 carbon atoms forming a ring".

[0189] In general formula (7), R 65 ~R 74 For specific examples of the "aryloxy group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "aryloxy groups with 6 to 18 carbon atoms forming a ring".

[0190] In general formula (7), R 65 ~R 74 For specific examples of the "arylthio group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylthio groups with 6 to 18 ring-forming carbon atoms".

[0191] In general formula (7), R 65 ~R 74 For specific examples of the "arylamino group with 6 to 18 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "arylamino groups with 6 to 18 ring-forming carbon atoms".

[0192] In general formula (7), R 65 ~R 74 For specific examples of the "diarylamino group with 12 to 36 ring-forming carbon atoms" represented by the above R 1 ~R 12 You may also refer to the example of "diarylamino groups with 12 to 36 ring-forming carbon atoms".

[0193] In general formula (7), R 65 ~R 74 For specific examples of "heteroaryl groups with 5 to 18 ring-forming atoms" represented by the above R 1 ~R 12You may also refer to the example of "heteroaryl groups with 5 to 18 carbon atoms forming a ring".

[0194] In general formula (7), R 65 ~R 74 Two adjacent molecules within the ring may bond to each other to form a ring. The ring formed is not particularly limited as long as it yields the compound (7) targeted by the present invention, and may or may not form an aromatic ring.

[0195] Specific examples of compounds (1) to (7) of the embodiments of the present invention include, for example, compounds represented by the following formulas (1)a to (7)a. However, compounds (1) to (7) of the embodiments of the present invention are not limited to these specific examples.

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] [ka]

[0203] The compounds represented by general formulas (1) to (7) in embodiments of the present invention can be synthesized by the following steps.

[0204] [ka] [L in the formula 1 However, the structure is (i) or (ii) below. [ka] (In structural formula (i), a is an integer between 1 and 8, and * indicates a bond.) [ka] (In structural formula (ii), * indicates a bond.)

[0205] Compound (12) can be synthesized by reacting a synthetic or commercially available compound (11) with triethanolamine.

[0206] [ka] In the second reaction scheme (Reaction Scheme (1)), L 1 R is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms. 1 ~R 12These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C16 di group. The group is selected from the group consisting of alkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, and the arylene group, aryl group, aryloxy group, arylthio group, arylamino group, diarylamino group, and heteroaryl group may be substituted with substituents.

[0207] Compounds (1) to (7) of the embodiments of the present invention can be synthesized by reacting synthetic or commercially available compounds (21) to (27) with compound (12) obtained in the first reaction scheme (Reaction Scheme (1)).

[0208] [Photoelectric conversion elements and solar cells] Compounds (1) to (7) of the embodiments of the present invention can be used in the hole transport layer of a photoelectric conversion element comprising a first electrode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a second electrode in this order. The present invention can provide a photoelectric conversion element comprising compounds (1) to (7) of the embodiments of the present invention in the photoelectric conversion layer (see Figure 1). The photoelectric conversion element is preferably used as a solar cell, and more preferably as a perovskite solar cell. The structure of the solar cell may be a nip-type structure (where the second electrode is a transparent electrode) or a pin-type structure (where the first electrode is a transparent electrode), as long as it comprises a first electrode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a second electrode in this order, but a pin-type structure is preferred.

[0209] The method for manufacturing the photoelectric conversion element and solar cell according to the embodiments of the present invention is not particularly limited and may be a general method for manufacturing the photoelectric conversion element and solar cell. For example, it may include the steps of forming a hole transport layer on a transparent electrode substrate (conductive layer) on which a mixture of indium oxide and tin oxide, ITO (Indium Tin Oxide), has been deposited; forming a photoelectric conversion layer by applying a perovskite solution on the hole transport layer; and forming an electron transport layer on the photoelectric conversion layer.

[0210] The process of forming the hole transport layer is not particularly limited, but may be carried out in the same manner as hole transport layers used in general solar cells. For example, the hole transport layer is introduced by coating a solution obtained by dissolving or dispersing compounds (1) to (7) of the embodiment of the present invention in a solvent onto a transparent electrode film and drying it. The method of coating the prepared solution is not particularly limited, and examples include spin coating, bar coating, immersion, and spraying. The temperature during coating is not particularly limited, but 0 to 50°C is preferred.

[0211] The solvent used to dissolve or disperse compounds (1) to (7) of the embodiments of the present invention is not particularly limited, but for example, alcoholic solvents such as water, methanol, ethanol, and isopropyl alcohol; ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; hydrocarbon solvents such as n-hexane, cyclohexane, benzene, toluene, xylene, chlorobenzene, and dichlorobenzene; ether solvents such as tetrahydrofuran and 2-methyltetrahydrofuran; ester solvents such as gamma-butyrolactone; sulfo solvents such as dimethyl sulfoxide; amide solvents such as N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMAC); chlorine-based solvents such as dichloromethane and chloroform; or mixed solvents thereof can be used, but amide solvents such as N,N-dimethylformamide are particularly preferred. The concentration of the solution of compound (1) of the embodiments of the present invention is not particularly limited, but for example, 0.001 to 500 mM is preferred, and 0.01 to 50 mM is more preferred.

[0212] The drying conditions after application are not particularly limited, but the drying temperature is preferably 20 to 200°C, and more preferably 60 to 150°C. The drying time is preferably 1 minute to 5 hours, and more preferably 3 minutes to 1 hour.

[0213] The hole transport layer may be formed solely from compounds (1) to (7) of the embodiments of the present invention, or it may contain compounds other than compounds (1) to (7) of the embodiments of the present invention. The compounds used in combination are not particularly limited, but may include compounds having bonding groups such as phosphonic acid groups, silanol groups, silatoran groups, trialkoxysilyl groups, trihalogenated silyl groups, sulfo groups, carboxyl groups, and boronic acid groups. The compound used in combination may also be, for example, a salt of compound (1) to (7) of the embodiment of the present invention.

[0214] The process for forming the photoelectric conversion layer is not particularly limited, but may be carried out in the same manner as photoelectric conversion elements used in general solar cells, for example. The photoelectric conversion layer may contain, for example, a perovskite compound. Perovskite crystals useful for obtaining highly efficient photoelectric conversion elements are known to have a three-dimensional structure and be represented by the compositional formula: ABX3 (wherein A is a monovalent cation of an amine compound or alkali metal element, B is a divalent cation of a metal element, and X is a monovalent anion of a halogen element), but may contain two or more types of perovskite compounds.

[0215] In the above compositional formula, A is not particularly limited, but for example, methylammonium (CH3NH3 + ) and formamidinium (HC(NH2)2 + Examples include organic ammonium compounds such as ) or at least one monovalent cation selected from alkali metals such as lithium (Li), sodium (Na), potassium (K), rubidium (Rb), and cesium (Cs). B is a divalent cation of at least one metallic element selected from, for example, magnesium (Mg), tin (Sn), and lead (Pb), although this is not particularly limited. X is at least one selected from chlorine (Cl), bromine (Br), and iodine (I). [Examples]

[0216] The compounds of the present invention can be synthesized through various routes, but an example of an embodiment for synthesizing the hole transport material of the present invention is shown below. However, the present invention is not limited to these embodiments.

[0217] <Example 1> Preparation of compound (1)a Compound (1)a was prepared based on the following reaction formulas (1)a and (2)a. [ka]

[0218] 0.125 g (3 mol%) of KOH, 19.5 g of toluene, and 9.2 g (1 equivalent) of triethanolamine were charged and stirred at 100°C for 1 hour to dissolve the KOH. After cooling to 90°C, 15.0 g of 3-bromotrimethoxysilane (11)a was added dropwise, stirred for 30 minutes, and then cooled to room temperature. The precipitated crystals were filtered, washed with 10 g of toluene, and dried under reduced pressure to obtain 17.0 g (93% yield) of white crystals of compound (12)a. 1 H NMR(300 MHz,CDCl3)δ3.76(t,J=6.0Hz,6H),3.39(t,J=7.5Hz,2H),2.81(t,J=5.7Hz,6H),1.62-2.02(m,2H),0.48(t,J=8.3z,2H)

[0219] [ka]

[0220] 1.5 g of 10,15-Dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole(21)a, 1.1 g of NaH (60% purity, 6.2 equivalents), 30 g of THF, and 4.11 g of compound (12)a (3.2 equivalents) were charged and the mixture was heated to 60°C. After stirring for 57 hours, the mixture was cooled to room temperature. 2.9 g of ammonium chloride was added to quench the mixture, and the precipitated crystals were filtered off. The crystals were washed with 51.0 g of chloroform and then concentrated. 17.9 g of THF was added to the concentrated solution, and the filtered crystals were dried to obtain 0.41 g of white crystals of compound (1)a (yield 9.5%). 1 H NMR(300 MHz,CDCl3)δ8.36(d,J=7.2Hz,3H), 7.69(d,J=8.4Hz,3H), 7.26-7.364(m,6H), 4.81(m,6H),3.69-3.75(m,18H),2.71-2.75(m,18H),2.20(m,6H),0.63-0.68(m,6H)

[0221] <Example 2> Manufacturing of a photoelectric conversion element of Example 2, containing compound (1)a of Example 1. Using a standard manufacturing process, a photoconversion element (perovskite solar cell) of Example 2, having the structure shown in Figure 1, was fabricated, containing compound (1)a of Example 1 in the hole transport layer.

[0222] [Preparation of compound solutions] Compound (1)a was dissolved in DMF to prepare a 0.25 mg / mL solution.

[0223] Next, the ITO substrate was subjected to UV ozone treatment, and a solution of compound (1)a was dropped onto it and spin-coated (at 3000 rpm for 30 seconds). The substrate was then heated on a hot plate at 120°C for 30 minutes to form a hole transport layer.

[0224] [Creating a Perovskite Layer] Formamidinium iodide (FAI) 542 mg, Lead(II) iodide (PbI2) 1.60 g of methylammonium bromide (MABr), 71 mg of methylammonium bromide (MABr), and 231 mg of lead(II) bromide (PbBr2) were dissolved in 2.8 mL of DMF and 0.7 mL of DMSO by stirring. 3.4 mL of this solution was measured out, and 128 μL of CsI solution (1.5 M, DMSO solvent) was added to prepare the perovskite solution. This solution was dropped onto the hole transport layer and allowed to stand for 20 seconds. Spin coating was performed at 1000 rpm for 10 seconds, and then at 4000 rpm for 30 seconds. 40 seconds after the start of spin coating, 700 μL of chlorobenzene (CB) was added dropwise to form a film, and the film was then heated at 100°C for 60 minutes to create the perovskite layer.

[0225] [Creating the electron transport layer] PCBM (30 mg / mL, CB solvent) was dropped onto the perovskite layer and spin-coated at 3000 rpm for 30 seconds. Subsequently, a zinc oxide solution (zinc oxide propanol dispersion diluted to half its concentration by adding IPA) was dropped and the mixture was rotated at 4000 rpm for 30 seconds. After that, gold was deposited as an electrode. Finally, the material was sealed using a coverslip and UV-curing resin to fabricate the photoconversion element (perovskite solar cell) of Example 2.

[0226] <Comparative Example 1> Manufacturing of the photoelectric conversion element of Comparative Example 1, containing the compound of Comparative Example 1 (3PATAT-C3). A photoconversion element (perovskite solar cell) for Comparative Example 1 was manufactured using the same method as in Example 2, except that the solution of compound (1)a was replaced with a solution of 3PATAT-C3 (0.7 mg / mL, ethanol solvent) and the deposition temperature of the hole transport layer was changed to heating on a hot plate at 100°C for 10 minutes.

[0227] [ka]

[0228] [Durability evaluation of the hole transport layer] Using the same method as described above, hole transport layers containing compound (1)a from Example 1 or compound 3PATAT-C3 from Comparative Example 1 were deposited on an ITO substrate. A thermal stability test was performed at 85°C for each hole transport layer to verify its durability over time. A constant-temperature drying oven FV-430 (manufactured by Advantec Toyo Co., Ltd.) was used for the tests. The contact angle between the substrate and water was measured before and after heating, and the retention rate of the contact angle (contact angle after the test / initial contact angle) was calculated to evaluate durability. A retention rate closer to 1 indicates less change and higher durability. The contact angle was measured using a contact angle meter DMs-401 (manufactured by Kyowa Interface Co., Ltd.) by dropping 1 μL of water onto the contact angle. The results are shown in Table 1.

[0229] [Table 1]

[0230] Table 1 shows that the hole transport layer using the compound of Example 1 had a higher contact angle retention rate compared to the hole transport layer using the compound of Comparative Example 1. It was also confirmed that the properties of the hole transport layer were better maintained even after UV irradiation, and a higher percentage of adhesion to the ITO substrate was maintained.

[0231] [Evaluation of solar cell performance] Table 2 shows the photoelectric conversion efficiency (PCE) of solar cells using each compound. A solar simulator (XIL-05B100KP, manufactured by Seric Co., Ltd.) was used for the measurements, at AM1.5G and 100mW / cm². 2 The IV characteristics were evaluated by irradiating solar cells with simulated sunlight.

[0232] [Table 2]

[0233] Table 2 confirms that a solar cell using the compound of the embodiment of the present invention in the hole transport layer has power generation performance.

[0234] From the above results, it was confirmed that the compounds of the embodiments of the present invention can be used as compounds that form a hole transport layer, that a new photoelectric conversion element can be obtained by using this hole transport layer, and that a more durable photoelectric conversion element and solar cell can be obtained than those using conventional compounds. [Industrial applicability]

[0235] The compounds of the embodiments of the present invention can be used as hole transport materials in perovskite solar cells. Furthermore, a tandem solar cell can be constructed in which perovskite utilizes short-wavelength light and silicon utilizes long-wavelength light, thereby achieving higher photoelectric conversion efficiency. Such solar cells can be used in a wide variety of fields, including roof-mounted panels (houses, buildings, factories), roof-integrated panels (houses, buildings, factories, garages, greenhouses), wall-mounted panels (houses, buildings, factories), window panes, blinds, shading sheets, solar power plants, power supplies for IoT devices (RFID tags, sensors, small electronic devices), mobile solar chargers, artificial satellites, automobiles, drones, and solar-powered aircraft.

Claims

1. A compound represented by any of the following general formulas (1), (2), (3), (4), (5), (6), and (7). 【Chemistry 1】 [In general formula (1), X １ ~X ３ Each of these is independently a hydrogen atom or the following structural formula (A). However, X １ ~X ３ At least one of them shows the following structural formula (A). 【Chemistry 2】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ are each independently a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, an alkynyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 9 carbon atoms, an alkoxycarbonylamino group having 1 to 9 carbon atoms, an acyl group having 1 to 9 carbon atoms, an acylamino group having 1 to 9 carbon atoms, an acyloxy group having 1 to 9 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 16 carbon atoms, an aminoalkyl group having 1 to 8 carbon atoms, a thioalkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, an aryloxy group having 6 to 18 ring-forming carbon atoms, an arylthio group having 6 to 18 ring-forming carbon atoms, an arylamino group having 6 to 18 ring-forming carbon atoms, a diarylamino group having 12 to 36 ring-forming carbon atoms, and a heteroaryl group having 5 to 18 ring-forming atoms, and the aryl group, aryloxy group, arylthio group, arylamino group, diarylamino group, heteroaryl group may be substituted with a substituent. R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ８ , R ９ , R １０ , R １１ and R １２ Any two adjacent ones of may be bonded to each other to form a ring. ] 【Transformation 3】 [In general formula (2), X ４ ~X ６ Each of these is independently a hydrogen atom or the following structural formula (A). However, X ４ ~X ６ At least one of them shows the following structural formula (A). 【Chemistry 4】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R １３ , R １４ , R １５ , R １６ , R １７ , R １８ , R １９ , R ２０ , R ２１ , R ２２ , R ２３ and R ２４ These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. １３ , R １４ , R １５ , R １６ , R １７ , R １８ , R １９ , R ２０ , R ２１ , R ２２ , R ２３ and R ２４ Two adjacent elements within the ring may be joined together to form a ring. 【Transformation 5】 [In general formula (3), X 7 ~X 8 Each of these is independently a hydrogen atom or the following structural formula (A). However, X 7 ~X 8 At least one of them shows the following structural formula (A). 【Transformation 6】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R ２ ５ , R ２６ , R ２７ , R ２８ , R ２９ , R ３０ , R ３１ , R ３２ , R ３３ and R ３４ These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. ２ ５ , R ２６ , R ２７ , R ２８ , R ２９ , R ３０ , R ３１ , R ３２ , R ３３ and R ３４ Two adjacent elements within the ring may be joined together to form a ring. 【Transformation 7】 [In general formula (4), X ９ to X １０ are each independently a hydrogen atom or the following structural formula (A). However, at least one of X ９ to X １０ represents the following structural formula (A). 【Transformation 8】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R ３５ , R ３６ , R ３７ , R ３８ , R ３９ , R ４０ , R ４１ , R ４２ , R ４３ [[ID=1N]]and R ４４ are each independently a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, an alkynyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 9 carbon atoms, an alkoxycarbonylamino group having 1 to 9 carbon atoms, an acyl group having / to 9 carbon atoms, an acylamino group having 1 to 9 carbon atoms, an acyloxy group having 1 to 9 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 16 carbon atoms, an aminoalkyl group having 1 to 8 carbon atoms, a thioalkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, an aryloxy group having 6 to 18 ring-forming carbon atoms, an arylthio group having 6 to 18 ring-forming carbon atoms, an arylamino group having 6 to 18 ring-forming carbon atoms, a diarylamino group having 12 to 36 ring-forming carbon atoms, and a heteroaryl group having 5 to 18 ring-forming atoms, and the aryl group, aryloxy group, arylthio group, arylamino group, diarylamino group, heteroaryl group may be substituted with a substituent. R ３５ ,R ３６ , R ３７ ,R ３８ ,R ３９ ,R ４０ ,R ４１ ,R ４２ ,R ４３ and R<J000111>two adjacent ones of may be bonded to each other to form a ring. ] It should be noted that there may be some inaccuracies in the translation due to the complexity and potential errors in the original text. It is recommended to double-check with the original professional content for more accurate understanding and use. 【Chemistry 9】 [In general formula (5), X １１ ~X １２ Each of these is independently a hydrogen atom or the following structural formula (A). However, X １１ ~X １２ At least one of them shows the following structural formula (A). 【Chemistry 10】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R ４５ , R ４６ , R ４７ , R ４８ , R ４９ , R ５０ , R ５１ , R ５２ , R ５３ , R and R ５４ These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. ４５ , R ４６ , R ４７ , R ４８ , R ４９ , R ５０ , R ５１ , R ５２ , R ５３ and R ５４ Two adjacent elements within the ring may be joined together to form a ring. 【Chemistry 11】 [In general formula (6), X １３ ~X １４ Each of these is independently a hydrogen atom or the following structural formula (A). However, X １３ ~X １４ At least one of them shows the following structural formula (A). 【Chemistry 12】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R ５５ , R ５６ , R ５７ , R ５８ , R ５９ , R ６０ , R ６１ , R ６２ , R ６３ and R ６４ These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. ５５ , R ５６ , R ５７ , R ５８ , R ５９ , R ６０ , R ６１ , R ６２ , R ６３ and R ６４ Two adjacent elements within the ring may be joined together to form a ring. 【Chemistry 13】 [In general formula (7), X １５ ~X １６ Each of these is independently a hydrogen atom or the following structural formula (A). However, X １５ ~X １６ At least one of them shows the following structural formula (A). 【Chemistry 14】 (In structural formula (A), L １ (wherein is an alkylene group having 1 to 8 carbon atoms or an arylene group having 6 to 18 ring-forming carbon atoms, and the arylene group may be substituted with substituents, and * indicates a bond.) Also, R ６５ , R ６６ , R ６７ , R ６８ , R ６９ , R ７０ , R ７１ , R ７２ , R ６３ and R ７４ These are, independently, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a sulfonyl group, a cyano group, an amino group, a sulfonylamino group, a thio group, a C1-C10 alkyl group, a C1-C8 alkenyl group, a C1-C8 alkynyl group, a C1-C8 alkoxy group, a C1-C9 alkoxycarbonyl group, a C1-C9 alkoxycarbonylamino group, a C1-C9 acyl group, a C1-C9 acylamino group, a C1-C9 acyloxy group, a C1-C8 alkylthio group, a C1-C8 alkylamino group, and a C2-C1 A group selected from the group consisting of 6 dialkylamino groups, C1-C8 aminoalkyl groups, C1-C8 thioalkyl groups, C6-C18 aryl groups, C6-C18 aryloxy groups, C6-C18 arylthio groups, C6-C18 arylamino groups, C12-C36 diarylamino groups, and C5-C18 heteroaryl groups, wherein the aryl groups, aryloxy groups, arylthio groups, arylamino groups, diarylamino groups, and heteroaryl groups may be substituted with substituents. ６５ , R ６６ , R ６７ , R ６８ , R ６９ , R ７０ , R ７１ , R ７２ , R ６３ and R ７４ Two adjacent elements within the ring may be joined together to form a ring.

2. L of the above structural formula (A) １ The compound according to claim 1, wherein the structural formula is (i) or (ii) shown below. 【Chemistry 15】 (In structural formula (i), a is an integer from 1 to 8, and * indicates a bond.) 【Chemistry 16】 (In structural formula (ii), * indicates a bond.)

3. A hole transport material comprising the compound according to claim 1 or 2.

4. A photoelectric conversion element comprising a first electrode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a second electrode in this order, wherein the hole transport layer contains the compound described in claim 1.

5. The photoelectric conversion element according to claim 4, having a p-i-n type structure.

6. The photoelectric conversion element according to claim 4, wherein the photoelectric conversion layer is a perovskite layer.

7. A solar cell comprising a photoelectric conversion element according to any one of claims 4 to 6.

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