Organic compound, preparation method therefor and use thereof, and perovskite solar cell

Abstract

The present application relates to an organic compound, a preparation method therefor and the use thereof, and a perovskite solar cell. The structure of the organic compound is as represented by formula (I), wherein X1-X3 are each independently selected from a single bond, an oxygen atom, a sulfur atom and C(R7)2, and R7 is independently selected from hydrogen and a substituted or unsubstituted C1-C18 alkyl group; L1-L3 are each independently selected from a substituted or unsubstituted C2-C18 alkylene group; R1-R6 and R11-R16 are each independently selected from hydrogen, a substituted or unsubstituted C1-C18 alkyl / alkoxy group, a halogen atom, a substituted or unsubstituted C1-C18 alkylthio group, a hydroxyl group, a sulfydryl group, a cyano group, an amino group, a substituted or unsubstituted C6-C18 aryl group, a substituted or unsubstituted C6-C18 arylamino group, a substituted or unsubstituted C3-C18 heteroaryl group, and a substituted or unsubstituted C3-C18 heteroarylamino group.

Description

Organic compound, preparation method and application thereof, and perovskite solar cell

[0001] Related applications

[0002] The present application claims priority to the Chinese patent application No. 202410865824.9, filed on July 1, 2024, entitled "Organic compound, preparation method and application thereof, and perovskite solar cell", the content of which is incorporated herein by reference in its entirety. TECHNICAL FIELD

[0003] The present application relates to the field of batteries, in particular to an organic compound, a preparation method thereof, a hole transport material, a perovskite solar cell, a preparation method thereof, and a photovoltaic module. BACKGROUND

[0004] Since 2009, the photoelectric conversion efficiency of perovskite solar cells has been increased from the initial 3.8% to more than 26%, becoming the most potential candidate in the next generation of photovoltaic technology. Trans perovskite photovoltaic devices have attracted much attention due to their simple preparation process, weak hysteresis effect, and better suitability for preparing stacked devices. Among the many research hotspots, the management of the hole transport interface of trans perovskite photovoltaic devices is particularly important, including the passivation of interface defects, energy level matching, hole extraction process, and inhibition of non-radiative recombination. The management of the perovskite bottom interface can help further improve the photoelectric conversion efficiency of perovskite photovoltaic devices and improve the stability of the devices, thus having important significance for their industrialization.

[0005] At present, self-assembled monolayer (SAMs) materials represented by [2-(9H-carbazol-9-yl)ethyl]phosphonic acid (2PACz) have many advantages such as simple process, low cost, and low usage, and have become the first choice for preparing efficient and stable trans perovskite solar cells. However, 2PACz has the problem of incomplete coverage on the conductive substrate, which causes the perovskite light-absorbing layer to directly contact the conductive substrate, resulting in poor optical and stability performance of the perovskite photovoltaic device.

[0006] SUMMARY

[0007] Based on this, the present application provides an organic compound, a preparation method thereof, a hole transport material, a perovskite solar cell, a preparation method thereof, and a photovoltaic module, which can effectively improve the optical and stability performance of the perovskite solar cell.

[0008] The technical solution of the present application to solve the above technical problems is as follows.

[0009] The first aspect of the present application provides an organic compound, the structure of which is shown in formula (I):

[0010] wherein X1to X3are each independently selected from a single bond, an oxygen atom, a sulfur atom, and C(R7)2, and R7is each independently selected from hydrogen and a substituted or unsubstituted C1to C4alkyl group. 18 alkyl group;

[0011] L1to L3are each independently selected from a substituted or unsubstituted C2to C8alkylene group. 18 alkylene group;

[0012] R1to R6and R 11 to R 16 are each independently selected from hydrogen, a substituted or unsubstituted C1to C8alkyl group, a substituted or unsubstituted C1to C8alkoxy group, a halogen atom, and an amino group. 18 alkyl group, a substituted or unsubstituted C1to C8alkoxy group, a halogen atom, and an amino group. 18 alkyl group, a substituted or unsubstituted C1to C8alkoxy group, a halogen atom, and an amino group. 18 alkyl group, a substituted or unsubstituted C1to C8alkoxy group, a halogen atom, and an amino group. 18 aryl group, a substituted or unsubstituted C6to C10aryl group, a substituted or unsubstituted C3to C10heteroaryl group, a substituted or unsubstituted C3to C10heteroaromatic amine group, and a substituted or unsubstituted C3to C10heteroaromatic amine group. 18 aryl group, a substituted or unsubstituted C6to C10aryl group, a substituted or unsubstituted C3to C10heteroaryl group, a substituted or unsubstituted C3to C10heteroaromatic amine group, and a substituted or unsubstituted C3to C10heteroaromatic amine group. 18 aryl group, a substituted or unsubstituted C6to C10aryl group, a substituted or unsubstituted C3to C10heteroaryl group, a substituted or unsubstituted C3to C10heteroaromatic amine group, and a substituted or unsubstituted C3to C10heteroaromatic amine group. 18 heteroaromatic amine group;

[0013] each of the substituted groups is independently selected from an amino group, a halogen, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, and a cyano group.

[0014] In some embodiments, in the organic compound, in the structure of formula (I), L1, L2, and L3are each independently selected from a substituted or unsubstituted C2to C8alkylene group.

[0015] In some embodiments, in the organic compound, in the structure of formula (I), R1to R6and R 11 to R 16 are each independently selected from hydrogen, a substituted or unsubstituted C1to C8alkyl group, a substituted or unsubstituted C1to C8alkoxy group, a halogen atom, and an amino group.

[0016] In some embodiments, in the organic compound, in the structure of formula (I), L1, L2, and L3are all the same.

[0017] In some embodiments, in the organic compound, in the structure of formula (I), L1, L2, and L3are all methylene groups.

[0018] In some embodiments, in the organic compound, in the structure of formula (I), L1, L2, and L3are all hexylene groups.

[0019] In some embodiments, in the organic compound, in the structure of formula (I), X1to X3are each independently selected from a single bond, an oxygen atom, a sulfur atom, and a dimethyl-substituted methylene group.

[0020] In some embodiments, the organic compound has the structure of formula (I), wherein X1, X2 and X3 are the same.

[0021] In some embodiments, the organic compound has the structure of formula (I), wherein R1-R6 are selected from hydrogen.

[0022] In some embodiments, the organic compound has the structure of formula (I), wherein R 11 -R 16 are independently selected from hydrogen and methoxy.

[0023] In some embodiments, the organic compound has the structure of formula (I), wherein R 11 -R 16 are selected from hydrogen.

[0024] In some embodiments, the organic compound has the structure of formula (I), wherein R 11 , R 13 and R 15 are selected from methoxy, and R 12 , R 14 , R 16 are selected from hydrogen. In some embodiments, the organic compound comprises at least one of the following compounds of formula (I-1) to (I-6):

[0025] The second aspect of the present application provides a method for preparing an organic compound, comprising the following steps:

[0026] mixing compound M1 and compound M2 to sequentially perform Buchwald-Hartwig coupling reaction and hydrolysis reaction to prepare the organic compound;

[0027] The compound M1 comprises the following compounds of formula (II-1) to (II-3), and the structure of the compound M2 is shown in formula (III):

[0028] wherein X a , X b and X c are independently selected from Br and I; X1-X3, L1-L3, R1-R6 and R 11 -R 16 are defined as in the first aspect.

[0029] The third aspect of the present application provides a hole transport material comprising the above-mentioned organic compound.

[0030] The fourth aspect of the present application provides a perovskite solar cell, comprising a first electrode, a hole transport layer, a perovskite light-absorbing layer and a second electrode, wherein the hole transport layer comprises the organic compound.

[0031] The fifth aspect of the present application provides a method for preparing a perovskite solar cell, comprising the following steps:

[0032] providing a first electrode;

[0033] forming a hole transport layer on the surface of the first electrode, wherein the raw material for preparing the hole transport layer comprises the organic compound;

[0034] forming a perovskite light-absorbing layer on the surface of the hole transport layer away from the first electrode;

[0035] forming a second electrode on the surface of the perovskite light-absorbing layer away from the hole transport layer.

[0036] In some embodiments, in the method for preparing a perovskite solar cell, the hole transport layer is prepared by a solution method.

[0037] The sixth aspect of the present application provides a photovoltaic module, comprising the perovskite solar cell or the perovskite solar cell prepared by the method described above.

[0038] Compared with the prior art, the organic compound provided by the present application has the following beneficial effects:

[0039] The organic compound provided by the present application comprises a rigid conjugated core azatriphenylene structure, a side arm structure connected to the nitrogen atom in the azatriphenylene, and a flexible alkyl phosphonic acid anchoring group, realizing a multi-level structure from rigid to flexible from inside to outside of the molecule; the introduction of the side arm structure effectively increases the conjugation length of the core unit, and when the hole transport material is used to prepare a hole transport layer of a perovskite solar cell, the carrier transport capacity of the hole transport material can be effectively enhanced; especially when the hole transport layer is prepared by a solution method, the steric hindrance effect brought by the side arm structure can effectively inhibit the intermolecular stacking, improve the solubility of the hole transport material in the solution, and thus effectively improve the uniformity of the hole transport layer; part of the flexible alkyl phosphonic acid anchoring group can be anchored with a conductive substrate to enhance the stability of the contact between the hole transport material and the conductive substrate, and the other part of the flexible alkyl phosphonic acid anchoring group can be used to contact the bottom of the perovskite light-absorbing layer, playing multiple roles such as passivation of defects and auxiliary crystallization of perovskite material, thereby effectively improving the optical performance and stability of the perovskite solar cell. BRIEF DESCRIPTION OF DRAWINGS

[0040] In order to more clearly illustrate the technical solutions in the embodiments of the present application or the technical solutions in the prior art, below the accompanying drawings needed to be used in the embodiments or the prior art description will be briefly introduced. Obviously, the accompanying drawings in the following description only represent some of the embodiments of the present application, and for those skilled in the art, other drawings can be obtained without creative effort based on the disclosed drawings.

[0041] Figure 1 is a hydrogen spectrum of the organic compound P1 (I-1). DETAILED DESCRIPTION

[0042] The technical solutions in the embodiments of the present application will be described clearly and completely below in combination with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments only represent some of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative effort belong to the scope of protection of the present application. Unless otherwise defined, all the technical and scientific terms used herein have the same meanings as those commonly understood by those skilled in the art to which the present application belongs. The terms used in the specification of the present application are only for the purpose of describing the specific embodiments and are not intended to limit the present application.

[0043] The terms "comprising", "containing", or any other variant thereof are intended to cover non-exclusive inclusion, so that a process, method, article, or apparatus including a series of elements not only includes those elements, but also includes other elements not explicitly listed, or further includes elements inherent to such a process, method, article, or apparatus. Without more limitations, the element defined by the phrase "including a" does not exclude the presence of additional identical elements in the process, method, article, or apparatus including the element. The indefinite article "a" and "an" before an element or component does not limit the number of the element or component (i.e. the number of occurrences), that is, one or at least one. Therefore, "one" or "an" should be interpreted to include one or at least one, and the singular form of the element or component also includes the plural form, unless the number is obviously only singular. The meaning of "plurality" is at least two, for example, two, three, etc., unless otherwise specifically limited.

[0044] The weight of the related components mentioned in the specification of the embodiments of the present application not only refers to the specific content of each component, but also represents the proportional relationship between the weights of each component. Therefore, as long as the content of the related components in the specification of the embodiments of the present application is enlarged or reduced in proportion, it is within the scope disclosed in the specification of the embodiments of the present application. Specifically, the weight mentioned in the specification of the embodiments of the present application can be μg, mg, g, kg, etc. mass units commonly known in the chemical field.

[0045] Unless otherwise shown or indicated in the operational embodiments, all figures used to represent the amounts, physicochemical properties, etc., of ingredients in the specification and claims are to be understood to be adjusted by the term "about" in all cases. For example, therefore, unless stated to the contrary, the numerical parameters listed in the foregoing specification and appended claims are approximations, and those skilled in the art can appropriately modify these approximations to obtain the desired characteristics by utilizing the teachings disclosed herein. The use of numerical ranges indicated by endpoints includes all numbers within that range and any range within that range; for example, 1 to 5 includes 1, 1.1, 1.3, 1.5, 2, 2.75, 3, 3.80, 4, and 5, etc.

[0046] One embodiment of this application provides an organic compound, the structure of which is shown in formula (I):

[0047] Among them, X1 to X3 are independently selected from single bonds, oxygen atoms, sulfur atoms and C(R7)2, respectively, and R7 is independently selected from hydrogen and substituted or unsubstituted C1 to C2 atoms. 18 alkyl;

[0048] L1 to L3 are independently selected from substituted or unsubstituted C2 to C3 cells, respectively. 18 Alkylene;

[0049] R1~R6 and R 11 ~R 16 Each is independently selected from hydrogen, substituted or unsubstituted C1 to C2. 18 Alkyl, substituted or unsubstituted C1-C 18 Alkoxy group, halogen atom, substituted or unsubstituted C1-C 18 Alkylthio, hydroxyl, mercapto, cyano, amino, substituted or unsubstituted C6-C 18 Aryl, substituted or unsubstituted C6-C 18 Aromatic amino group, substituted or unsubstituted C3-C 18 Heteroaryl groups and substituted or unsubstituted C3-C 18 heteroaryl amines.

[0050] The organic compound provided in the application comprises a rigid conjugated core azatriphenylene structure, a side arm structure connected to the nitrogen atom in the azatriphenylene, and a flexible alkyl phosphonic acid anchoring group, realizing a multi-level structure from inside to outside of the molecule, from rigid to flexible; the introduction of the side arm structure effectively increases the conjugation length of the core unit, and when the hole transport layer of the perovskite solar cell is prepared by using the hole transport material, the carrier transport capacity of the hole transport material can be effectively enhanced; especially when the hole transport layer is prepared by using a solution method, the steric hindrance effect brought by the side arm structure can effectively inhibit the intermolecular stacking, improve the solubility of the hole transport material in the solution, and thus effectively improve the uniformity of the hole transport layer; part of the flexible alkyl phosphonic acid anchoring group can be anchored with the conductive substrate to enhance the stability of the contact between the hole transport material and the conductive substrate, and the other part of the flexible alkyl phosphonic acid anchoring group can be used to contact the bottom of the perovskite light-absorbing layer, and play multiple roles such as passivation of defects and auxiliary crystallization of perovskite materials, thereby effectively improving the optical performance and stability of the perovskite solar cell.

[0051] In the present text, "selected from A and B" means that the involved group can be any one of A and B. "Selected from A, B and C" means that the involved group can be any one of A, B or C. By analogy.

[0052] It can be understood that "independently selected" means that the same group can be selected, or different groups can be selected. Further, when X1-X3 is a single bond, the side arm structure connected to the nitrogen atom in the azatriphenylene is a carbazole structure; the structural formula of the dimethyl-substituted methylene is Alkyl is a group composed of carbon and hydrogen atoms, and when an alkyl group loses a hydrogen atom, an alkylene group is formed; C2-C 18 Alkylene refers to a group obtained by removing one hydrogen atom from an alkyl group with 2-18 carbon atoms, including but not limited to -CH2(CH2)nCH2- (wherein n is an integer from 0 to 12, including but not limited to 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, …), ethylene 1,2-ethylene (-CH2CH2-), isopropylidene , and the like; C1-C 18 Alkylthio has a chemical formula of RS-, wherein R is an alkyl group with 1-18 carbon atoms; C6-C 18 Aryl refers to an aryl group with 6-18 ring carbon atoms; C3-C 18 Heteroaryl refers to a heteroaryl group with 3-18 ring carbon atoms, and the heteroatoms on the ring include at least one of nitrogen, oxygen and sulfur; further, C1-C 18Alkyl includes, but is not limited to, at least one of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and the like, where propyl includes at least one of n-propyl and isopropyl, butyl includes at least one of n-butyl, isobutyl, t-butyl, and sec-butyl; substituted or unsubstituted C1-C 18 Alkyl, substituted or unsubstituted C1-C 18 Alkoxy, substituted or unsubstituted C1-C 18 Alkylthio, substituted or unsubstituted C6-C 18 Aryl, substituted or unsubstituted C6-C 18 Arylamino, substituted or unsubstituted C3-C 18 Heteroaryl, substituted or unsubstituted C3-C 18 Heteroarylamino, substituted or unsubstituted C3-C 18 Alkyl, substituted or unsubstituted C1-C 18 Alkoxy, substituted or unsubstituted C1-C 18 Alkylthio, substituted or unsubstituted C6-C 18 Aryl, substituted or unsubstituted C6-C 18 Arylamino, substituted or unsubstituted C3-C 18 Heteroaryl, substituted or unsubstituted C3-C 18 Heteroarylamino, substituted or unsubstituted C3-C

[0053] In some examples, the organic compound has a structure of Formula (I), wherein L1, L2, and L3 are each independently selected from substituted or unsubstituted C2-C8 alkylene.

[0054] Further, L1, L2, and L3 are each independently selected from substituted or unsubstituted C3-C6 alkylene.

[0055] It can be appreciated that L1, L2, and L3 can each be different, two of them can be the same, and all three of them can be the same.

[0056] In some examples, the organic compound has a structure of Formula (I), wherein L1, L2, and L3 are each the same.

[0057] In some examples, the organic compound has a structure of Formula (I), wherein L1, L2, and L3 are each the same.

[0058] In some examples, the organic compound is one in which, in the structure of formula (I), L1, L2, and L3 are each hexylene.

[0059] In some examples, the organic compound is one in which, in the structure of formula (I), R1-R6 and R 11 R 16 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, halogen, and amino.

[0060] In some examples, the organic compound is one in which, in the structure of formula (I), R1-R6 and R 11 R 16 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C4 alkyl.

[0061] It is understood that R1-R6 and R 11 R 16 may each be different, two or more of which can be the same.

[0062] In some examples, the organic compound is one in which, in the structure of formula (I), R1-R6 are each selected from hydrogen.

[0063] In some examples, the organic compound is one in which, in the structure of formula (I), R 11 R 16 are each independently selected from the group consisting of hydrogen and methoxy.

[0064] Further, in the organic compound, in the structure of formula (I), R 11 R 16 are each hydrogen.

[0065] Further, R 11 , R 13 , and R 15 are selected from methoxy, and R 12 , R 14 , and R 16 are selected from hydrogen.

[0066] In some examples, the organic compound is one in which, in the structure of formula (I), X1-X3 are each independently selected from the group consisting of a single bond, an oxygen atom, a sulfur atom, and a dimethyl-substituted methylene.

[0067] It is understood that X1, X2, and X3 can each be different, two of which can be the same, all three of which can be the same.

[0068] In some examples, the organic compound is one in which, in the structure of formula (I), X1, X2, and X3 are each the same.

[0069] In some examples, the organic compound includes at least one of the compounds shown in the following formulas (I-1) to (I-6):

[0070] An embodiment of the present application provides a method for preparing an organic compound, including the following step S10:

[0071] The compound M1 and the compound M2 are mixed to sequentially perform a Buchwald-Hartwig coupling reaction and a hydrolysis reaction, so as to prepare the organic compound.

[0072] The compound M1 includes the compounds shown in the following formulas (II-1) to (II-3), and the structure of the compound M2 is shown in the following formula (III):

[0073] wherein X a , X b and X c are independently selected from Br and I; X1 to X3, L1 to L3, R1 to R6 and R 11 to R 16 are defined as above.

[0074] The organic compound with the specific structure described above can significantly improve the optical performance and stability of the perovskite solar cell when used as a hole transport material to prepare a hole transport layer of the perovskite solar cell.

[0075] It can be understood that X1 to X3, L1 to L3, R 11 to R 16 in the compounds shown in the formulas (II-1) to (II-3) correspond to X1 to X3, L1 to L3, R 11 to R 16 in the compound shown in the formula (I); it can be further understood that the compounds shown in the formulas (II-1) to (II-3) can all be different, or two or three of them can be the same. For example, when X1, X2 and X3 in the compound shown in the formula (I) are the same, L1, L2 and L3 are the same, R 11 , R 13 and R5 are the same, R 12 , R 14 and R 16 are the same, the formulas (II-1) to (II-3) are the same compound, and when performing the Buchwald-Hartwig coupling reaction, the compound M1 only needs to be mixed with the compound M2.

[0076] The structure of the product obtained by the Buchwald-Hartwig coupling reaction is shown in the following formula (IV):

[0077] In some examples, the Buchwald-Hartwig coupling reaction in step S10 further comprises adding a palladium catalyst, a base, an alkyl phosphine, and an aromatic solvent.

[0078] In some examples, the palladium catalyst includes, but is not limited to, at least one of tris(dibenzylideneacetone)dipalladium and palladium acetate.

[0079] In some examples, the base includes, but is not limited to, an alkali metal alcoholate; further, the alkali metal alcoholate includes, but is not limited to, sodium tert-butoxide.

[0080] In some examples, the alkyl phosphine includes, but is not limited to, tri-tert-butylphosphonium tetrafluoroborate.

[0081] In some examples, the aromatic solvent includes, but is not limited to, toluene.

[0082] In some examples, the Buchwald-Hartwig coupling reaction in step S10 is performed at a temperature of 100°C to 120°C for a time period of 18h to 36h.

[0083] It can be understood that the temperature of the Buchwald-Hartwig coupling reaction includes, but is not limited to, 100°C, 102°C, 105°C, 108°C, 110°C, 112°C, 115°C, 118°C, 120°C, and the time period includes, but is not limited to, 18h, 20h, 22h, 25h, 28h, 30h, 32h, 35h, 36h.

[0084] In some examples, the Buchwald-Hartwig coupling reaction in step S10 is performed under an atmosphere of nitrogen or an inert gas.

[0085] It can be understood that the inert gas includes, but is not limited to, helium (kr), neon (Ne), argon (Ar), krypton (He), xenon (xe), radon (Rn).

[0086] In some examples, after the Buchwald-Hartwig coupling reaction in step S10, a post-processing step S11 is further included.

[0087] The reaction solution after the Buchwald-Hartwig coupling reaction is sequentially quenched with water, extracted with dichloromethane, and the organic phase is concentrated.

[0088] In some examples, in step S11, the concentrated substance is further purified by column chromatography.

[0089] In some examples, the eluent used in the column chromatography is petroleum ether and dichloromethane. Further, the volume ratio of petroleum ether to dichloromethane is 2:1 to 1:3.

[0090] In some examples, in step S10, the hydrolysis reaction includes step S12:

[0091] The compound N prepared by the Buchwald-Hartwig coupling reaction, a Lewis acid, and an organic solvent are mixed to perform the hydrolysis reaction.

[0092] In some examples, in step S12, the Lewis acid includes, but is not limited to, at least one of trimethylchlorosilane, trimethylbromosilane, trimethyliodosilane, and the like.

[0093] In some examples, in step S12, the organic solvent includes, but is not limited to, 1,4-dioxane.

[0094] In some examples, in step S12, the hydrolysis reaction is performed under a nitrogen or inert gas atmosphere.

[0095] In some examples, in step S12, the temperature of the hydrolysis reaction is 20°C to 30°C, and the time is 8h to 15h.

[0096] In some examples, in step S12, after the hydrolysis reaction, a step S13 of post-treatment is further included:

[0097] The organic solvent in the reaction solution after the hydrolysis reaction is removed, methanol is added for dissolution, water is added dropwise until solid is precipitated in the system, the hydrolysis is continued, and then the mixture is filtered and washed.

[0098] It can be understood that the compound M1 can be obtained commercially or prepared by a conventional method.

[0099] In some examples, in step S10, the preparation method of the compound M1 includes step S14:

[0100] The compound M3 and triethyl phosphite are mixed to perform an Arbuzov reaction to prepare the compound M1; the compound M3 includes at least one of the compounds shown in the following formula (V-1) to formula (V-3):

[0101] It can be understood that the compound M3 is a raw material of the compound M1 shown in the formula (II-1) to formula (II-3).

[0102] In some examples, in step S14, the temperature of the Arbuzov reaction is 140°C to 160°C, and the time is 18h to 36h.

[0103] It can be understood that the temperature of the Arbuzov reaction includes, but is not limited to, 140°C, 142°C, 145°C, 148°C, 150°C, 152°C, 155°C, 158°C, 160°C, and the time includes, but is not limited to, 18h, 20h, 22h, 25h, 28h, 30h, 32h, 35h, 36h.

[0104] In some examples, in step S14, it can be understood that the compound M3 can be obtained commercially or prepared by a conventional method.

[0105] In some examples, in step S14, the preparation method of the compound M3 includes step S15:

[0106] The compound M3 is prepared by mixing the compound M4, a dibromoalkane, a base and a phase transfer catalyst to perform an alkylation reaction, and the compound M4 includes at least one of the compounds shown in the following formula (VI-1) to formula (VI-3):

[0107] It can be understood that the dibromoalkane corresponds to L1-L3 in the compound M3, and the dibromoalkane includes Br-L1-Br, Br-L2-Br and Br-L3-Br.

[0108] In some examples, in step S15, the dibromoalkane includes, but is not limited to, at least one of 1,2-dibromoethane, 1,3-dibromoethane and 1,4-dibromobutane.

[0109] An embodiment of the present application provides an application of the above-mentioned organic compound in the preparation of a hole transport material. Another embodiment of the present application provides a hole transport material comprising the above-mentioned organic compound.

[0110] An embodiment of the present application provides a perovskite solar cell comprising a first electrode, a hole transport layer, a perovskite light-absorbing layer and a second electrode, and the hole transport layer comprises the above-mentioned organic compound.

[0111] In some examples, the perovskite solar cell further comprises an electron transport layer arranged between the perovskite light-absorbing layer and the second electrode.

[0112] The above-mentioned organic compound can effectively improve the optical performance and stability of the perovskite solar cell when used as a hole transport material to prepare a hole transport layer of the perovskite solar cell.

[0113] It can be understood that the present application does not limit the types and thicknesses of the materials of the first electrode, the perovskite light-absorbing layer, the electron transport layer and the second electrode in the perovskite solar cell, which are conventional in the art.

[0114] In some examples, the first electrode is a transparent conductive electrode.

[0115] In some examples, the transparent conductive electrode includes, but is not limited to, at least one of indium tin oxide (ITO), indium zinc oxide (IZO), tungsten-doped indium oxide (IWO), and aluminum-doped zinc oxide (AZO).

[0116] In some examples, the perovskite solar cell, the perovskite light-absorbing layer includes a perovskite material of ABX3 type, wherein A is at least one of cesium ion, rubidium ion, potassium ion, methylamine ion, formamidinium ion, methylenediamine ion, benzamidine cation, guanidinium cation, B is at least one of divalent lead ion and divalent tin ion, and X is at least one of fluoride ion, chloride ion, bromide ion, iodide ion, thiocyanate ion, tetrafluoroborate ion, hexafluorophosphate ion, formate ion, and acetate ion.

[0117] In some examples, the perovskite solar cell, the electron transport layer includes, but is not limited to, at least one of fullerene and a derivative thereof.

[0118] Further, the fullerene and the derivative thereof include, but are not limited to, at least one of C60, C70, and PCBM, etc.

[0119] In some examples, the perovskite solar cell, the second electrode includes, but is not limited to, at least one of silver, copper, conductive oxide, and carbon electrode.

[0120] In some examples, the perovskite solar cell further includes a hole blocking layer disposed between the electron transport layer and the second electrode.

[0121] In some examples, the hole blocking layer includes, but is not limited to, at least one of bathocuproine (BCP, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and zirconium acetylacetonate.

[0122] An embodiment of the present application provides a preparation method of a perovskite solar cell, including the following steps:

[0123] providing a first electrode;

[0124] forming a hole transport layer on a surface of the first electrode; the preparation raw material of the hole transport layer includes the organic compound described above

[0125] forming a perovskite light-absorbing layer on a surface of the hole transport layer away from the first electrode;

[0126] forming a second electrode on a surface of the perovskite light-absorbing layer away from the hole transport layer.

[0127] In some examples, the method for preparing the perovskite solar cell further comprises, before the step of forming the second electrode, a step of forming an electron transport layer on a surface of the perovskite light-absorbing layer away from the hole transport layer.

[0128] In some examples, the method for preparing the perovskite solar cell further comprises, after the step of forming the electron transport layer and before the step of forming the second electrode, a step of disposing a hole blocking layer on a surface of the electron transport layer away from the perovskite light-absorbing layer.

[0129] It can be understood that the application does not limit the formation method of each layer, for example, including but not limited to magnetron sputtering, spin coating, slot coating or evaporation, etc.

[0130] In some examples, the method for preparing the perovskite solar cell further comprises, after the step of forming the electron transport layer and before the step of forming the second electrode, a step of disposing a hole blocking layer on a surface of the electron transport layer away from the perovskite light-absorbing layer.

[0131] In some examples, the solution method comprises the following steps S20:

[0132] Mixing the above-mentioned organic compound and solvent to prepare a hole transport solution;

[0133] Spin coating the hole transport solution to the conductive side surface of the first electrode, and forming the hole transport layer through annealing treatment.

[0134] In some examples, in the step S20, the solvent comprises tetrahydrofuran.

[0135] In some examples, in the step S20, the concentration of the hole transport solution is 0.5mg / mL-2mg / mL.

[0136] It can be understood that the concentration of the hole transport solution includes but is not limited to 0.5mg / mL, 1mg / mL, 1.5mg / mL, 2mg / mL.

[0137] In some examples, in the step S20, the annealing treatment is performed at a temperature of 80℃-120℃ for 8min-20min.

[0138] It can be understood that the annealing treatment temperature includes but is not limited to 80℃, 90℃, 100℃, 110℃, 120℃, and the time is 8min, 10min, 12min, 15min, 20min. In some examples, it can be within the range formed by any two of these point values as end values, and the same applies above.

[0139] An embodiment of the application provides an application of the above-mentioned perovskite solar cell or the above-mentioned perovskite tandem cell in preparing a photovoltaic module. Another embodiment of the application provides a photovoltaic module comprising the above-mentioned perovskite solar cell or the above-mentioned perovskite tandem cell.

[0140] An embodiment of the present application provides a photovoltaic module comprising the perovskite solar cell or the perovskite solar cell prepared by the preparation method.

[0141] It can be understood that the photovoltaic module can be applied in a photovoltaic power station, such as a ground power station, a roof power station, a water surface power station, etc., and can also be applied in a device or apparatus for generating power by using solar energy, such as a user solar power source, a solar street lamp, a solar car, a solar building, etc. It can also be understood that the application scenarios of the photovoltaic system include but are not limited to the above, that is, the photovoltaic system can be applied in all fields requiring power generation by using solar energy. Taking a photovoltaic power generation system network as an example, the photovoltaic system can comprise a photovoltaic array, a combiner box and an inverter, the photovoltaic array can be an array combination of a plurality of photovoltaic modules, for example, a plurality of photovoltaic modules can form a plurality of photovoltaic arrays, the photovoltaic arrays are connected to the combiner box, the combiner box can combine the currents generated by the photovoltaic arrays, the combined current flows through the inverter to be converted into an alternating current required by a power grid, and then the alternating current is connected to a power network to realize solar power supply.

[0142] The photovoltaic module provided by the present application can be used in, but is not limited to, an electric device such as a vehicle, a ship or an aircraft.

[0143] The electric device provided by the present application can be, but is not limited to, a mobile phone, a tablet, a notebook computer, an electric toy, an electric tool, an electric vehicle, an electric car, a ship, a spacecraft, etc. The electric toy can include a fixed or mobile electric toy, such as a game console, an electric car toy, an electric ship toy and an electric aircraft toy, etc. The spacecraft can include an airplane, a rocket, a space shuttle and a spacecraft, etc.

[0144] The present application will be further described in detail in combination with specific embodiments, but the embodiments of the present application are not limited thereto.

[0145] The organic compound P1 described in formula (I-1) is prepared, and the synthesis route is as follows:

[0146] Step one: synthesis of intermediate compound M3 (V-11)

[0147] Compound M4 (VI-11) 3-bromocarbazole (2.46 g, 10 mmol) and tetrabutylammonium bromide (0.31 g, 1 mmol) were dissolved in 1,4-dibromobutane (30 mL), and 50% potassium hydroxide solution (10 mL) was added, and the reaction was stirred at 65 °C for 24 hours. After the reaction was completed, water was added for quenching, and dichloromethane was used for extraction. The organic phase was dried over anhydrous sodium sulfate and concentrated, and column chromatography was used for purification. The eluent ratio was petroleum ether: dichloromethane = 1:0 to 1:1, and finally the colorless sticky liquid product was obtained in a yield of 3.50 g, 92%. 1H NMR (400 MHz, DMSO-d6) δ 8.15 (d, J = 8.5 Hz, 1H), 7.99 (d, J = 2.0 Hz, 1H), 7.49 (dd, J = 8.2, 1.7 Hz, 1H), 7.46 - 7.38 (m, 3H), 7.32 - 7.25 (m, 1H), 4.33 (t, J = 5.3 Hz, 2H), 3.60 (t, J = 3.8 Hz, 2H), 1.94 - 1.77 (m, 4H).

[0148] Step two: synthesis of intermediate compound M1 (II-11)

[0149] Intermediate compound M3 (V-11) (3.0 g, 8.0 mmol) was dissolved in triethyl phosphite (25 mL), and the reaction was stirred at 160 °C for 24 hours. After the reaction was completed, the excess triethyl phosphite was removed by rotary evaporation, and column chromatography was used for purification. The eluent ratio was petroleum ether: dichloromethane = 10:1 to 1:3, and finally the light yellow sticky liquid product was obtained in a yield of 3.30 g, 95%. 1H NMR (400 MHz, DMSO-d6) δ 8.15 (d, J = 8.5 Hz, 1H), 7.99 (d, J = 2.0 Hz, 1H), 7.49 (dd, J = 8.2, 1.7 Hz, 1H), 7.45 - 7.39 (m, 3H), 7.31 - 7.25 (m, 1H), 4.28 (t, J = 5.3 Hz, 2H), 4.02 - 3.95 (m, 4H), 2.02 - 1.95 (m, 2H), 1.86 - 1.80 (m, 2H), 1.70 - 1.57 (m, 2H), 1.32 (t, J = 7.1 Hz, 6H).

[0150] Step three: synthesis of intermediate compound N (IV-11)

[0151] Intermediate compound M1 (II-11) (2.90 g, 6.6 mmol), azatriphenylene (0.69 g, 2.0 mmol), sodium tert-butoxide (0.86 g, 9.0 mmol), tri-tert-butylphosphonium tetrafluoroborate (232 mg, 0.8 mmol) and tris(dibenzylideneacetone)dipalladium (183 mg, 0.2 mmol) were dissolved in anhydrous toluene (30 mL) and stirred at 110 °C for 24 h under an inert gas atmosphere. The reaction progress was followed by thin layer chromatography and when the starting material was completely consumed, the reaction was allowed to cool to room temperature, quenched with water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and concentrated. Further purification was achieved by column chromatography. Eluent ratio was petroleum ether: dichloromethane = 2:1 to 1:3. Finally, 1.60 g of yellow solid was obtained with a yield of 57%.1H NMR (400 MHz, DMSO-d6) δ 8.19 - 8.09 (m, 6H), 7.73 - 7.65 (m, 6H), 7.62 - 7.51 (m, 6H), 7.44 - 7.37 (m, 6H), 7.31 (td, J = 6.9, 1.4 Hz, 3H), 7.28 - 7.22 (m, 6H), 4.28 (t, J = 5.1 Hz, 6H), 4.04 - 3.93 (m, 12H), 2.04 - 1.93 (dt, J = 12.1, 8.6 Hz, 6H), 1.88 - 1.77 (ddd, J = 11.7, 6.5, 5.1 Hz, 6H), 1.69 - 1.56 (m, 6H), 1.32 (t, J = 7.1 Hz, 18H).

[0152] Step four: synthesis of organic compound P1 (I-1)

[0153] Intermediate compound N (IV-11) (1.42 g, 1.0 mmol) was dissolved in anhydrous 1,4-dioxane (15 mL) under a nitrogen atmosphere and trimethylsilyl bromide (2.30 g, 15.0 mmol) was added. The reaction was stirred at room temperature for 12 h. After the reaction was completed, the organic solvent was removed by rotary evaporation and then methanol (10 mL) was added to redissolve the product. Deionized water was added dropwise until solid precipitated in the reaction system. The hydrolysis was continued for 3 h with stirring, then the product was obtained by filtration and washing as a yellow solid with a yield of 75%.1H NMR (400 MHz, DMSO-d6) δ 8.18 - 8.10 (m, 6H), 7.72 - 7.65 (m, 6H), 7.61 - 7.50 (m, 6H), 7.44 - 7.37 (m, 6H), 7.31 (m, 3H), 7.29 - 7.21 (m, 6H), 4.28 (t, J = 5.1 Hz, 6H), 2.01 - 1.89 (m, 6H), 1.82 (tt, J = 6.8, 5.2 Hz, 6H), 1.67 - 1.57 (m, 6H).

[0154] The organic compound P2 described in formula (I-2) is prepared, and the synthetic route is basically the same as the above-mentioned synthetic route of P1, except that the raw material 3-bromocarbazole is replaced by an equal molar amount of 3-bromophenothiazine in step one, and P2 is shown in formula (I-2):

[0155] The hydrogen spectrum data of the organic compound P2 is:1H NMR (400 MHz, DMSO-d6) δ 8.13 (dd, J = 7.1, 1.4 Hz, 3H), 7.67 (dd, J = 6.2, 1.8 Hz, 3H), 7.34-7.29 (m, 6H), 7.27-7.17 (m, 15H), 7.14-7.09 (m, 6H), 3.84 (t, J = 5.3 Hz, 6H), 1.94 (ddd, J = 11.9, 10.4, 9.4 Hz, 6H), 1.75 (ttd, J = 6.6, 5.3, 0.9 Hz, 6H), 1.69-1.57 (m, 6H).

[0156] The organic compound P3 shown in formula (I-3) is prepared, and the synthetic route is basically the same as the above-mentioned synthetic route of P1, except that the raw material 3-bromocarbazole is replaced by an equal molar amount of 3-bromophenoxazine in step one, and P3 is shown in formula (I-3):

[0157] The hydrogen spectrum data of the organic compound P3 is:1H NMR (400 MHz, DMSO-d6) δ 8.15-8.10 (m, 3H), 7.67 (dd, J = 6.4, 1.7 Hz, 3H), 7.35-7.22 (m, 6H), 7.22-7.10 (m, 15H), 7.01 (dd, J = 7.3, 2.2 Hz, 3H), 6.92-6.86 (m, 3H), 3.85 (t, J = 5.4 Hz, 6H), 1.94 (ddd, J = 11.9, 10.4, 9.4 Hz, 6H), 1.79-1.71 (m, 6H), 1.68-1.57 (m, 6H).

[0158] The organic compound P4 shown in formula (I-4) is prepared, and the synthetic route is basically the same as the above-mentioned synthetic route of P1, except that the raw material 3-bromocarbazole is replaced by an equal molar amount of 2-bromo-9,9-dimethylindolizine in step one, and P4 is shown in formula (I-4):

[0159] The hydrogen spectrum data of the organic compound P4 is:1H NMR (400 MHz, DMSO-d6) δ 8.13 (dd, J = 7.1, 1.3 Hz, 3H), 7.67 (dd, J = 6.3, 1.7 Hz, 3H), 7.40 (d, J = 2.3 Hz, 3H), 7.34 - 7.17 (m, 9H), 7.15 - 7.07 (m, 6H), 7.07 - 6.98 (m, 6H), 6.85 (dd, J = 6.5, 1.5 Hz, 3H), 3.85 (t, J = 5.4 Hz, 6H), 1.94 (ddd, J = 11.9, 10.4, 9.4 Hz, 6H), 1.75 (ttd, J = 6.6, 5.3, 1.0 Hz, 6H), 1.68 - 1.58 (m, 6H), 1.61 (s, 18H).

[0160] The organic compound P5 shown in formula (I-5) is prepared, and the synthesis route is basically the same as that of P1 described above, except that the raw material 1,4-dibromobutane is replaced by equimolar amount of 1,6-dibromohexane in step one, and P5 is shown in formula (I-5):

[0161] The hydrogen spectrum data of the organic compound P5 is:1H NMR (400 MHz, DMSO-d6) δ 8.17 - 8.11 (m, 6H), 7.70 - 7.63 (m, 6H), 7.60 - 7.48 (m, 6H), 7.42 - 7.35 (m, 6H), 7.30 (m, 3H), 7.27 - 7.20 (m, 6H), 4.27 (t, J = 5.6 Hz, 6H), 2.00 - 1.81 (m, 12H), 1.69 - 1.57 (m, 6H), 1.49 - 1.30 (m, 12H).

[0162] The organic compound P6 shown in formula (I-6) is prepared, and the synthesis route is basically the same as that of P1 described above, except that the raw material 3-bromocarbazole is replaced by equimolar amount of 3-bromo-6-methoxycarbazole in step one, and P6 is shown in formula (I-6):

[0163] The hydrogen spectrum data of organic compound P6 is: 1H NMR (400 MHz, DMSO-d6) δ 8.09 (dd, J = 6.9, 1.5 Hz, 3H), 7.71-7.58 (m, 9H), 7.58-7.50 (m, 6H), 7.37 (d, J = 8.2 Hz, 3H), 7.35-7.25 (m, 6H), 6.89 (dd, J = 8.2, 2.7 Hz, 3H), 4.19 (t, J = 5.1 Hz, 6H), 3.83 (s, 9H), 2.02-1.90 (m, 6H), 1.87-1.78 (m, 6H), 1.74-1.64 (m, 6H).

[0164] Example 1

[0165] A preparation method of a trans perovskite solar cell, comprising the following steps:

[0166] (1) The TCO conductive glass is sequentially cleaned with deionized water, acetone and isopropanol by ultrasonic cleaning for 15 min, and finally placed in a drying box at 75°C for drying standby; the dried TCO glass substrate is placed in an ultraviolet ozone machine for treatment for 5 min to remove organic impurities on the surface and optimize the surface wettability;

[0167] (2) 1 mg of organic compound P1 is dissolved in 1 mL of tetrahydrofuran, spin-coated at 3000 rpm for 30 s, then dynamically washed once with 300 uL of isopropanol, and then annealed at 100°C for 10 min to form a self-assembled hole transport layer;

[0168] (3) 922 mg of lead iodide, 348 mg of iodomethanimine, 45.46 mg of cesium iodide, 13.5 mg of chloromethylamine and 55.62 mg of lead chloride are dissolved in 1 mL of a mixed solvent of N,N-dimethylformamide and N-methylpyrrolidone (1000:192), and stirred at room temperature until completely dissolved to obtain a perovskite precursor solution;

[0169] (4) In a nitrogen glove box, 30 uL of the perovskite precursor solution is added dropwise to the ITO conductive glass on which the hole transport layer is formed, spin-coated at 1000 rpm for 10 s, then spin-coated at 5000 rpm for 30 s, and then the TCO glass is placed on a hot stage and heated at 100°C for 40 min to anneal to form a perovskite layer;

[0170] (5) 20 mg of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) is dissolved in 1 mL of chlorobenzene, and stirred at room temperature to obtain a [6,6]-phenyl-C61-butyric acid methyl ester solution;

[0171] (6) Take 30 uL of [6,6]-phenyl-C61-butyric acid methyl ester solution to form a perovskite layer on the ITO conductive glass, spin-coat at 3000 rpm for 60 s to form an electron transport layer;

[0172] (7) Dissolve 0.5 mg of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) in 1 mL of isopropanol, and stir at room temperature to obtain a hole blocking layer solution;

[0173] (8) Take 40 uL of the hole blocking layer solution and drop it onto the electron transport layer, spin-coat at 5000 rpm for 35 s to form a hole blocking layer;

[0174] (9) Transfer the TCO conductive glass with the hole blocking layer, PCBM electron transport layer, perovskite layer, and hole transport layer to a vacuum coating instrument, and wait for the vacuum degree to be 3*10 -4 Pa, and then evaporate silver electrode to form a silver electrode with a thickness of 100 nm to obtain an electrode layer.

[0175] Example 2

[0176] The same as Example 1, except that in step (2), the organic compound P1 is replaced with an equal amount of organic compound P2.

[0177] Example 3

[0178] The same as Example 1, except that in step (2), the organic compound P1 is replaced with an equal amount of organic compound P3.

[0179] Example 4

[0180] The same as Example 1, except that in step (2), the organic compound P1 is replaced with an equal amount of organic compound P4.

[0181] Example 5

[0182] The same as Example 1, except that in step (2), the organic compound P1 is replaced with an equal amount of organic compound P5.

[0183] Example 6

[0184] The same as Example 1, except that in step (2), the organic compound P1 is replaced with an equal amount of organic compound P6.

[0185] Comparative Example 1

[0186] The same as Example 1, except that in step (2), the organic compound P1 is replaced with an equal amount of organic compound Q, which has the structure shown in formula (X):

[0187] Comparative Example 2

[0188] The same as Example 1, except that in step (2), the organic compound P1 was replaced by an equal mass of 2PACz, whose structure is shown below. 2PACz is an abbreviation of [2-(9H-carbazol-9-yl)ethyl]phosphonic acid.

[0189] The perfromance of the perovskite solar cells prepared in each example and comparative example was tested for open-circuit voltage Voc, short-circuit current density Jsc, fill factor FF and energy conversion efficiency PCE a , using I-V curve, under the following test conditions: AM 1.5G standard solar spectrum, irradiance of 1000 W / m 2 . The experimental test results are shown in Table 1.

[0190] Stability test: after the cells were placed at 85℃ for 100h, the performance was tested according to the above conditions to obtain the photoelectric conversion efficiency PCE b , the photoelectric conversion efficiency retention rate = PCE b / PCE a ×100%, and the photoelectric conversion efficiency retention rate is shown in Table 1.

[0191] Table 1

[0192] As can be seen from Table 1, compared with Comparative Examples 1-2, the perovskite solar cells prepared by using the organic compounds P1-P6 containing the rigid conjugated core azatriphenylene structure, the side arm structure fragment connected to the nitrogen atom in azatriphenylene and the flexible alkyl phosphonic acid anchoring group as the hole transport material in Examples 1-6 have higher photoelectric conversion efficiency and better stability; among them, Comparative Example 1 uses the organic compound Q as the hole transport material, which contains the rigid conjugated core azatriphenylene structure and the flexible alkyl phosphonic acid anchoring group, but does not contain the side arm structure fragment connected to the nitrogen atom in azatriphenylene, which is easy to cause intermolecular π-π stacking, which is not conducive to the film uniformity of the thin film prepared by solution method, so that the photoelectric conversion efficiency and stability of the perovskite solar cells prepared in Comparative Example 1 are slightly better than those of Comparative Example 2 using the traditional hole transport material, but are obviously inferior to Examples 1-6.

[0193] Each technical feature of the above-described examples can be combined arbitrarily, and in order to make the description simple, not all possible combinations of each technical feature in the above-described examples are described, however, as long as the combination of these technical features does not exist contradictory, it should be considered as the scope of the present disclosure.

[0194] The above embodiments only express several implementation ways of the present application, and the description is relatively specific and detailed, but it should not be understood as a limitation to the patent scope of the application. It should be pointed out that for ordinary skilled persons in the art, several modifications and improvements can be made without departing from the concept of the present application, which all belong to the protection scope of the present application. Therefore, the protection scope of the patent of the present application should be subject to the appended claims.

Claims

1. An organic compound, characterized by, The structure of the organic compound is shown as formula (I): wherein X1to X3are each independently selected from a single bond, an oxygen atom, a sulfur atom, and C(R7)2, R7is each independently selected from hydrogen and a substituted or unsubstituted C1to C6alkyl group; 18 alkyl; L1to L3are each independently selected from substituted or unsubstituted C2to C10alkylene; and 18 alkylene; R1~R6 and R 11 ~R 16 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1~C 18 alkyl group, a substituted or unsubstituted C1~C 18 alkoxy group, a halogen atom, a substituted or unsubstituted C1~C 18 alkylthio group, a hydroxyl group, a mercapto group, a cyano group, an amino group, a substituted or unsubstituted C6~C 18 aryl group, a substituted or unsubstituted C3~C 18 aromatic amine group, a substituted or unsubstituted C3~C 18 heteroaryl group, and a substituted or unsubstituted C3~C 18 heteroaromatic amine group; each of said substituted groups is independently selected from the group consisting of amino, halogen, nitro, hydroxyl, thiol, carboxyl and cyano.

2. The organic compound according to claim 1, wherein In the structure of formula (I), L1, L2 and L3 are each independently selected from substituted or unsubstituted C2-C8 alkylene.

3. The organic compound according to claim 1 or 2, wherein In the structure of formula (I), R1to R6and R 11 16 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C1to C8alkyl, substituted or unsubstituted C1to C8alkoxy, halogen, and amino.​ 4. The organic compound according to any one of claims 1 to 3, wherein In the structure of formula (I), L1, L2 and L3 are all the same. Preferably, L1, L2 and L3 are all butylene. Preferably, L1, L2 and L3 are all hexylene.

5. The organic compound according to any one of claims 1 to 4, wherein In the structure of formula (I), X1-X3 are each independently selected from single bond, oxygen atom, sulfur atom and dimethyl-substituted methylene.

6. The organic compound according to any one of claims 1 to 5, wherein In the structure of formula (I), X1, X2 and X3 are all the same.

7. The organic compound according to any one of claims 1 to 6, wherein In the structure of formula (I), R1-R6 are all selected from hydrogen.

8. The organic compound according to any one of claims 1 to 7, wherein In the structure of formula (I), R 11 ~R 16 are each independently selected from hydrogen and methoxy; Preferably, R 11 ~R 16 are each selected from hydrogen; Preferably, R 11 , R 13 and R 15 are selected from methoxy, R 12 , R 14 , R 16 is selected from hydrogen.

9. The organic compound according to any one of claims 1 to 8, wherein The organic compound includes at least one of compounds represented by the following formulas (I-1) to (I-6):

10. The method for producing an organic compound according to any one of claims 1 to 9, wherein comprising the following steps: mixing compound M1 and compound M2 to sequentially perform Buchwald-Hartwig coupling reaction and hydrolysis reaction, to prepare the organic compound; The compound M1 includes compounds represented by the following formulae (II-1) to (II-3), and the compound M2 has a structure represented by the following formula (III): wherein X a , X b and X c are each independently selected from Br and I, X1to X3, L1to L3, R1to R6and R 11 ~R 16 each as defined in claim 1.

11. A hole transporting material, characterized in that, comprising the organic compound according to any one of claims 1-9.

12. A perovskite solar cell, characterized by, comprising a first electrode, a hole transport layer, a perovskite light absorbing layer and a second electrode, wherein the hole transport layer comprises the organic compound according to any one of claims 1-9.

13. A method of manufacturing a perovskite solar cell, characterized by, comprising the following steps: providing a first electrode; forming a hole transport layer on the surface of the first electrode; the raw material for preparing the hole transport layer comprises the organic compound according to any one of claims 1-9; forming a perovskite light absorbing layer on the surface of the hole transport layer away from the first electrode; forming a second electrode on the surface of the perovskite light absorbing layer away from the hole transport layer.

14. The production method according to claim 13, wherein The method for preparing the hole transport layer comprises a solution method.

15. A photovoltaic module, characterized by, comprising the perovskite solar cell according to claim 12 or the perovskite solar cell prepared by the method according to claim 13 or 14.

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