Organic compound and preparation method thereof, hole transport material, perovskite cell and laminated cell

Abstract

The invention relates to an organic compound and a preparation method thereof, a hole transport material, a perovskite cell and a laminated cell. The structure of the organic compound is as shown in a formula (I): # imgabs0 #; wherein n is an integer from 10 to 1000, and Ar is selected from one of the structures shown in the formula (II): # imgabs 1 #; r < 1 > to R < 2 > are respectively and independently selected from substituted or unsubstituted C < 1 > to C < 18 > alkyl groups; r < 3 > to R < 8 > are respectively and independently selected from one of hydrogen, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C1-C18 alkylthio, halogen atoms, trifluoromethyl, hydroxyl, sulfydryl, cyano, amino and substituted or unsubstituted C6-C18 aryl; R < 3 > to R < 8 > are independently selected from one of hydrogen, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C1-C18 alkylthio, halogen atoms, trifluoromethyl, hydroxyl, sulfydryl, cyano and substituted or unsubstituted C6-C18 aryl; m is independently selected from integers from 1 to 4 when appearing each time; x is selected from one of a single bond, an oxygen atom, C (R9) 2 and NR10, and R9-R10 are respectively and independently selected from hydrogen and substituted or unsubstituted C1-C18 alkyl; each substituted substituent is independently selected from one of C1-C4 alkyl, amino, halogen, nitryl, hydroxyl, sulfydryl, carboxyl and cyano.

Description

Technical Field

[0001] The present application relates to the technical field of batteries, and particularly to an organic compound, a preparation method thereof, a hole transport material, a perovskite battery and a tandem battery. Background Art

[0002] In a perovskite battery, as an important transport layer material between the perovskite light-absorbing layer and the electrode, the hole transport material is not only responsible for hole extraction and transport to improve the photoelectric conversion efficiency of the perovskite battery, but also can modify the interface and block the flow of electrons to enhance the stability of the perovskite battery. However, the stability of traditional hole transport materials still needs to be further improved. Summary of the Invention

[0003] Based on this, the present application provides an organic compound with good stability, a preparation method thereof, a hole transport material, a perovskite battery and a tandem battery.

[0004] The technical solution for the present application to solve the above technical problems is as follows.

[0005] In the first aspect of the present application, an organic compound is provided, and the structure of the organic compound is shown in formula (I):

[0006]

[0007] Wherein, n is an integer from 10 to 1000, and Ar is selected from one of the structures shown in formula (II):

[0008]

[0009] R 1 ~R 2 are each independently selected from substituted or unsubstituted C 1 ~C 18 alkyl;

[0010] R 3 ~R 8 are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 18 alkyl, substituted or unsubstituted C 1 ~C 18 alkoxy, substituted or unsubstituted C 1 ~C 18 alkylthio, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano, amino and substituted or unsubstituted C 6 ~C 18 aryl;

[0011] Each time m appears, it is independently selected from an integer of 1 to 4;

[0012] X is selected from one of a single bond, an oxygen atom, C(R 9 ) 2 and NR 10 , and R 9 ~R 10 are each independently selected from hydrogen and substituted or unsubstituted C 1 ~C 18 alkyl;

[0013] Each of the substituents of each said substitution is independently selected from one of C 1 ~C 4 alkyl, amino, halogen, nitro, hydroxyl, mercapto, carboxyl and cyano.

[0014] In some embodiments, in the organic compound, R 1 ~R 2 are each independently selected from substituted or unsubstituted C 1 ~C 4 alkyl;

[0015] and / or, R 3 ~R 8 are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 4 alkyl, substituted or unsubstituted C 1 ~C 4 alkoxy, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano and amino;

[0016] and / or, X is selected from one of a single bond, an oxygen atom and C(R 9 ) 2 , and R 9 is selected from hydrogen and substituted or unsubstituted C 1 ~C 4 alkyl.

[0017] In some embodiments, in the organic compound, R 1 ~R 2 are each independently selected from one of methyl and ethyl; optionally, R 1 ~R 2 are all methyl;

[0018] and / or, R 3 ~R 8 are each independently selected from one of hydrogen, methyl and ethyl; optionally, R 3 ~R 8 are all hydrogen;

[0019] and / or, R 9 is selected from one of methyl and ethyl; optionally, R 9 is methyl.

[0020] In some of these embodiments, in the organic compound, the structure of the organic compound is as shown in formula (I-1):

[0021] .

[0022] In some of these embodiments, in the organic compound, Ar is selected from one of the structures shown in formula (II-1) to formula (II-3):

[0023] .

[0024] The second aspect of the present application provides a method for preparing an organic compound, comprising the following steps:

[0025] Polymerize a norbornene monomer under the action of a catalyst to prepare an organic compound;

[0026] The structure of the norbornene monomer is as shown in formula (III), and the structure of the organic compound is as shown in formula (I):

[0027]

[0028] Wherein, n is an integer from 10 to 1000, and Ar is selected from one of the structures shown in formula (II):

[0029]

[0030] R 1 ~R 2 Are each independently selected from substituted or unsubstituted C 1 ~C 18 alkyl;

[0031] R 3 ~R 8 Are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 18 alkyl, substituted or unsubstituted C 1 ~C 18 alkoxy, substituted or unsubstituted C 1 ~C 18 alkylthio, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano, amino and substituted or unsubstituted C 6 ~C 18 aryl;

[0032] Each time m appears, it is independently selected from an integer from 1 to 4;

[0033] X is selected from one of a single bond, an oxygen atom, C(R 9 ) 2 and NR 10 , R9 ~R 10 are each independently selected from hydrogen and substituted or unsubstituted C 1 ~C 18 alkyl;

[0034] Each of the substituents of each said substitution is independently selected from one of C 1 ~C 4 alkyl, amino, halogen, nitro, hydroxyl, mercapto, carboxyl and cyano.

[0035] In some embodiments, in the method for preparing an organic compound, the preparation of the norbornene monomer comprises the following steps:

[0036] Mixing the compound shown in formula (IV), the compound shown in formula (V) and the compound shown in formula (VI) to carry out a Suzuki coupling reaction to prepare the norbornene monomer;

[0037]

[0038] wherein Y is a halogen atom.

[0039] The third aspect of the present application provides a hole transporting material, comprising the organic compound provided in the first aspect or the organic compound prepared by the preparation method provided in the second aspect.

[0040] The fourth aspect of the present application provides a perovskite solar cell, comprising a first electrode, a hole transporting layer, a perovskite light absorbing layer and a second electrode. The hole transporting layer is located between the first electrode and the perovskite light absorbing layer, the perovskite light absorbing layer is located between the hole transporting layer and the second electrode, and the hole transporting layer comprises the hole transporting material provided in the third aspect.

[0041] The fifth aspect of the present application provides a tandem solar cell, comprising the perovskite solar cell provided in the fourth aspect.

[0042] The organic compound of the present application, based on the poly(norbornene) main chain structure, by simultaneously introducing alkoxytriphenylamine and a side chain unit of the structure shown in formula (II), enables the organic compound to have high thermal stability.

[0043] Using the organic compound of the present application as the hole transporting material of a perovskite solar cell, it has a good mobility, which is beneficial to the extraction and transport of holes, and has a HOMO energy level that matches the perovskite and is relatively deep, which can effectively improve the photoelectric conversion efficiency and stability of the perovskite solar cell. Description of the Drawings

[0044] To more clearly illustrate the technical solutions in the embodiments of the present application and more comprehensively understand the present application and its beneficial effects, the following will briefly introduce the accompanying drawings required for the description of the embodiments. Obviously, the accompanying drawings in the following description are only some embodiments of the present application. For those skilled in the art, without creative efforts, other accompanying drawings can be obtained based on these drawings.

[0045] Figure 1 Schematic structural diagram of a perovskite solar cell provided for an embodiment;

[0046] Figure 2 1H NMR spectrum of compound 9;

[0047] Figure 3 1H NMR spectrum of compound 13;

[0048] Figure 4 1H NMR spectrum of compound 16.

[0049] Reference numerals:

[0050] 100: Perovskite solar cell; 110: Transparent conductive electrode; 120: Hole transport layer; 130: Perovskite light-absorbing layer; 140: Electron transport layer; 150: Metal electrode. Detailed implementation manners

[0051] The following further details the present application in combination with the implementation manners and embodiments. It should be understood that these implementation manners and embodiments are only used to illustrate the present application and not to limit the scope of the present application. The purpose of providing these implementation manners and embodiments is to make the understanding of the disclosed content of the present application more thorough and comprehensive.

[0052] It should also be understood that the present application can be implemented in many different forms and is not limited to the implementation manners and embodiments described herein. Those skilled in the art can make various changes or modifications without departing from the connotation of the present application, and the equivalent forms obtained also fall within the protection scope of the present application. For example, the features described as part of one implementation manner can be combined in a suitable manner with another implementation manner to generate a new implementation manner. In addition, in the following description, a large number of specific details are given to provide a more thorough understanding of the present application. It should be understood that the present application can be implemented without one or more of these details.

[0053] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field to which the present application belongs. The terms used in the specification of the present application herein are only for the purpose of describing the implementation manners and embodiments and are not intended to limit the present application.

[0054] Unless otherwise specified or there are contradictions, the terms or phrases used in this text have the following meanings:

[0055] In this application, when it comes to "multiple", "multiple kinds", "multiple times", etc., without special limitations, it means greater than 2 or equal to 2 in quantity. For example, "one or more kinds" means one kind or greater than or equal to two kinds.

[0056] In this text, "their combinations", "any combination thereof", "any combination mode thereof", etc. include all suitable combination modes of any two or more than two items among the listed items.

[0057] In this text, for "suitable combination mode", "suitable mode", "any suitable mode", etc., the "suitable" mentioned therein is subject to being able to implement the technical solution of this application, solve the technical problems of this application, and achieve the expected technical effects of this application.

[0058] In this text, "preferred", "better", "more preferable", "it is advisable" are only used to describe the implementation manners or embodiments with better effects, and it should be understood that they do not constitute a limitation on the protection scope of this application. If there are multiple "preferred" in a technical solution, without special instructions and without contradictions or mutual restrictions, each "preferred" is independent.

[0059] In this application, "further", "even further", "especially", etc. are used for descriptive purposes, indicating differences in content, but should not be understood as a limitation on the protection scope of this application.

[0060] In this application, "optionally", "optional", "optional", mean that it can be there or not, that is, it refers to any one of the two parallel options of "yes" or "no". If there are multiple "optional" in a technical solution, without special instructions and without contradictions or mutual restrictions, each "optional" is independent.

[0061] In this application, in "the first aspect", "the second aspect", "the third aspect", "the fourth aspect", etc., the terms "first", "second", "third", "fourth", etc. are only used for descriptive purposes, and cannot be understood as indicating or implying relative importance or quantity, nor can it be understood as implicitly indicating the importance or quantity of the indicated technical features. Moreover, "first", "second", "third", "fourth", etc. only serve the purpose of non-exhaustive enumeration and description, and it should be understood that they do not constitute a closed limitation on quantity.

[0062] In this application, for the technical features described in an open manner, it includes the closed technical solutions composed of the listed features, and also includes the open technical solutions containing the listed features.

[0063] In this application, when it comes to numerical intervals (i.e., numerical ranges), unless otherwise specified, the distribution of the selectable numerical values within the numerical interval is considered continuous, and includes the two numerical endpoints of the numerical interval (i.e., the minimum value and the maximum value), as well as each numerical value between these two numerical endpoints. Unless otherwise specified, when the numerical interval only refers to the integers within the numerical interval, it includes the two endpoint integers of the numerical range, as well as each integer between the two endpoints, which is equivalent to directly listing each integer. When multiple numerical ranges are provided to describe features or characteristics, these numerical ranges can be combined. In other words, unless otherwise specified, the numerical ranges disclosed herein should be understood to include any and all sub-ranges subsumed therein. The "numerical values" in the numerical interval can be any quantitative values, such as numbers, percentages, ratios, etc. The "numerical interval" is allowed to broadly include numerical interval types such as percentage intervals, ratio intervals, ratio value intervals, etc.

[0064] The temperature parameter in this application, unless otherwise specified, allows both constant temperature treatment and variation within a certain temperature range. It should be understood that the constant temperature treatment allows the temperature to fluctuate within the accuracy range controlled by the instrument. Fluctuations within ranges such as ±5°C, ±4°C, ±3°C, ±2°C, ±1°C are allowed.

[0065] In this application, the terms "room temperature" or "normal temperature" generally refer to 4°C to 35°C, such as 20°C ± 5°C. In some embodiments of this application, "room temperature" or "normal temperature" refers to 10°C to 30°C. In some embodiments of this application, "room temperature" or "normal temperature" refers to 20°C to 30°C.

[0066] In this application, when it comes to the unit of the data range, if the unit is only attached after the right endpoint, it means that the units of the left endpoint and the right endpoint are the same. For example, 3~5 h means that the units of the left endpoint "3" and the right endpoint "5" are both h (hours).

[0067] All the documents mentioned in this application are cited as references in this application, just as if each document is cited separately as a reference. Unless it conflicts with the invention purpose and / or technical solution of this application, the cited documents involved in this application are cited for all their contents and all their purposes. When this application involves cited documents, the definitions of relevant technical features, terms, nouns, phrases, etc. in the cited documents are also cited together. When this application involves cited documents, the examples and preferred ways of the relevant technical features cited can also be incorporated as references into this application, but only to the extent that this application can be implemented. It should be understood that when the cited content conflicts with the description in this application, this application shall prevail or be amended adaptively according to the description of this application.

[0068] In the description of the embodiments of the present application, the mass or weight of the related components mentioned not only can refer to the specific content of each component, but also can represent the proportional relationship of the mass or weight between each component. Therefore, as long as the content of the related components in the description of the embodiments of the present application is enlarged or reduced in proportion, it is within the scope disclosed in the description of the embodiments of the present application. Specifically, the mass or weight described in the description of the embodiments of the present application can be units well-known in the chemical industry such as μg, mg, g, kg, etc.

[0069] In the present application, "substituted" in "substituted or unsubstituted" means that the hydrogen atom in the group is replaced by a substituent, and "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom in the group is not replaced by other atoms or atomic groups.

[0070] Perovskite solar cells (PSCs) include normal perovskite solar cells (n-type) and inverted perovskite solar cells (p-type); the normal perovskite solar cell from bottom to top is a transparent conductive oxide, an electron transport layer, a perovskite photoabsorber layer, a hole transport layer and a metal electrode in sequence; the inverted perovskite solar cell is to reverse the positions of the electron transport layer and the hole transport layer, and its structure from bottom to top is usually a transparent conductive oxide, a hole transport layer, a perovskite photoabsorber layer, an electron transport layer and a metal electrode.

[0071] Compared with the normal perovskite solar cell, the inverted perovskite solar cell uses a hole transport material (HTMs) as the bottom substrate of the perovskite layer, and has the advantages of simple manufacturing process, negligible hysteresis phenomenon, compatibility with tandem devices, etc., and the efficiency of the inverted perovskite solar cell has made remarkable progress and is approaching the efficiency of the normal perovskite solar cell.

[0072] Compared with 3D perovskite, the quasi-2D Ruddlesden-Popper (RP) perovskite with larger organic spacer cations exhibits better environmental stability. Although the stability is better, the larger organic spacer cations may increase the quantum and dielectric confinement of the quasi-2D RP perovskite, which limits the improvement of the power conversion efficiency (PCEs) of the quasi-2D RP PSCs.

[0073] In the inverted perovskite solar cell, the hole transport material (HTMs) as an important transport layer material between the perovskite layer and the transparent electrode is not only responsible for the extraction and transport of holes, blocking the flow of electrons, but also directly affects the crystallization and film formation of perovskite, and plays a decisive role in the improvement of battery performance and the realization of large-area commercial applications.

[0074] The HTMs in perovskite solar cells are mainly divided into three categories: inorganic hole transport materials, organic small molecule hole transport materials, and organic polymer hole transport materials. Polymer hole transport materials have become important charge transport layer materials commonly used in inverted perovskite solar cells due to their excellent film-forming properties, high mobility, and strong solvent tolerance; commonly used ones include poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA), and poly(3,4-ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS); among them, the inherent acidity and hygroscopicity of PEDOT:PSS will corrode and accelerate the degradation of perovskite materials, which will affect the stability of inverted PSCs; problems such as the high cost, strong hydrophobicity, and not deep enough HOMO energy level of PTAA have all increased the instability and cost of the device.

[0075] One embodiment of the present application provides an organic compound, and the structure of the organic compound is shown in formula (I):

[0076]

[0077] Wherein, n is an integer from 10 to 1000, and Ar is selected from one of the structures shown in formula (II):

[0078]

[0079] R 1 ~R 2 are each independently selected from substituted or unsubstituted C 1 ~C 18 alkyl;

[0080] R 3 ~R 8 are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 18 alkyl, substituted or unsubstituted C 1 ~C 18 alkoxy, substituted or unsubstituted C 1 ~C 18 alkylthio, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano, amino, and substituted or unsubstituted C 6 ~C 18 aryl;

[0081] Each time m appears, it is independently selected from an integer from 1 to 4;

[0082] X is selected from a single bond, an oxygen atom, C(R 9 ) 2 and NR 10 one of them, R 9 ~R 10 are each independently selected from hydrogen and substituted or unsubstituted C1 ~C 18 alkyl;

[0083] each substituted substituent is independently selected from C 1 ~C 4 alkyl, amino, halogen, nitro, hydroxyl, mercapto, carboxyl and cyano.

[0084] The organic compound of the present application, based on the poly(norbornene) main chain structure, has high thermal stability by simultaneously introducing alkoxytriphenylamine and side chain units of the structure shown in formula (II).

[0085] Using this organic compound as the hole transporting material in a perovskite solar cell, it has good mobility, which is beneficial to the extraction and transport of holes, and has a HOMO energy level that matches the perovskite and is relatively deep, which can effectively improve the photoelectric conversion efficiency and stability of the perovskite solar cell.

[0086] It can be understood that C 1 ~C 18 refers to the number of carbon atoms being 1 to 18, which can be a straight chain or a branched chain, and this number of carbon atoms does not include the carbon atoms of the substituent when substituting; further, C 1 ~C 18 has the number of carbon atoms including 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18; in some examples, it can be within the range formed by any two of these point values as the end values, the same below; for example, R 1 ~R 2 can be independently selected from substituted or unsubstituted C 1 ~C 15 alkyl, C 2 ~C 10 alkyl, C 3 ~C 6 alkyl, C 1 ~C 4 alkyl, etc.; C 1 ~C 18 alkoxy and C 1 ~C 18 alkylthio and so on; C 6 ~C 18 aryl refers to the number of carbon atoms on the aromatic ring being 6 to 18; m refers to the number of substituents, including 1, 2, 3 or 4; for example, m(R 3 ) refers to the number of R 3 groups can be 1, 2, 3 or 4, respectively substituting the hydrogen on the benzene ring.

[0087] In some of these examples, in the organic compound, R 1 ~R2 are each independently selected from substituted or unsubstituted C 1 ~C 4 alkyl.

[0088] In some examples, in the organic compound, R 1 ~R 2 are each independently selected from one of methyl and ethyl; optionally, R 1 ~R 2 are all methyl.

[0089] In some examples, in the organic compound, R 3 ~R 5 are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 4 alkyl, substituted or unsubstituted C 1 ~C 4 alkoxy, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano and amino.

[0090] In some examples, in the organic compound, R 3 ~R 5 are each independently selected from one of hydrogen, methyl and ethyl; optionally, R 3 ~R 5 are all hydrogen.

[0091] In some examples, in the organic compound, the structure of the organic compound is as shown in formula (I-1):

[0092] .

[0093] In some examples, in the organic compound, R 6 ~R 8 are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 4 alkyl, substituted or unsubstituted C 1 ~C 4 alkoxy, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano and amino.

[0094] In some examples, in the organic compound, R 6 ~R 8 are each independently selected from one of hydrogen, methyl and ethyl; optionally, R 6 ~R 8 are all hydrogen.

[0095] In some examples, in the organic compound, R 9 ~R 10 are each independently selected from hydrogen and substituted or unsubstituted C1 ~C 6 alkyl group

[0096] In some of these examples, in the organic compound, X is selected from a single bond, an oxygen atom, and C(R 9 ) 2 wherein one of R 9 is selected from hydrogen and substituted or unsubstituted C 1 ~C 4 alkyl group. Optionally, R 9 is selected from one of methyl and ethyl; further, R 9 is methyl

[0097] In some of these examples, in the organic compound, Ar is selected from one of the structures shown in Formula (II-1) to Formula (II-3):

[0098] .

[0099] It can be understood that the groups shown in Formula (II-1)) to Formula (II-3) are N-phenylcarbazole, N-phenylcarbazole acridine, and N-phenylphenoxazine, respectively, and Ar is located at the 6 active site of norbornene

[0100] Polymers based on the non-conjugated poly(cis,exo-2,3-diaryl norbornene) backbone (polynorbornenyl) have various advantages. For example, the ROMP ring-opening polymerization process is simple and fast, the degree of polymerization is high, and the material cost is low; based on the polynorbornene backbone structure in this application, by introducing alkoxytriphenylamine and side chain units of the structure shown in Formula (II), the organic compound shown in Formula (I) is designed and synthesized, and it is used as an undoped hole transport material in perovskite cells, especially in inverted (quasi-two-dimensional Quasi-2D) perovskite cells, and a higher photoelectric conversion efficiency can be obtained

[0101] The organic compound of this application can be applied to large-area inverted perovskite cells

[0102] The organic compound of this application has a large molecular weight, a high thermal decomposition temperature and hole mobility, has good wettability to the perovskite precursor solution, has simple synthesis steps, low cost, good thermal stability and film-forming properties, and the energy level matches that of the perovskite, promoting the crystallization and film formation of the perovskite; when used as a hole transport material in inverted perovskite solar cells, no other additives need to be doped, a good photoelectric conversion efficiency can be obtained, and the repeatability is relatively high

[0103] One embodiment of this application provides a preparation method of an organic compound, including step S10:

[0104] Polymerize norbornene monomers under the action of a catalyst to prepare an organic compound

[0105] The structure of the norbornene monomer is shown in Formula (III), and the structure of the organic compound is shown in Formula (I):

[0106]

[0107] Among them, n is an integer from 10 to 1000, and Ar is selected from one of the structures shown in Formula (II):

[0108]

[0109] R 1 ~R 2 are each independently selected from substituted or unsubstituted C 1 ~C 18 alkyl;

[0110] R 3 ~R 8 are each independently selected from hydrogen, substituted or unsubstituted C 1 ~C 18 alkyl, substituted or unsubstituted C 1 ~C 18 alkoxy, substituted or unsubstituted C 1 ~C 18 alkylthio, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano, amino and substituted or unsubstituted C 6 ~C 18 aryl;

[0111] Each time m appears, it is independently selected from an integer from 1 to 4;

[0112] X is selected from one of a single bond, an oxygen atom, C(R 9 ) 2 and NR 10 wherein R 9 ~R 10 are each independently selected from hydrogen and substituted or unsubstituted C 1 ~C 18 alkyl;

[0113] Each substituent of each substitution is independently selected from one of C 1 ~C 4 alkyl, amino, halogen, nitro, hydroxyl, mercapto, carboxyl and cyano.

[0114] It can be understood that the preparation method of the organic compound provided in this application can obtain the above-mentioned organic compound, and the characteristics between the organic compound provided in this application and the preparation method of the organic compound can be mutually applicable. Further, it can be understood that the reaction formula of step S10 is:

[0115]

[0116] In some of these examples, in step S10, the catalyst includes the second-generation Grubbs reagent (2nd Generation Grubbs Catalyst).

[0117] In some of these examples, in step S10, the reaction solution of the polymerization reaction further includes a solvent; further, the solvent includes at least one of tetrahydrofuran (THF) and toluene.

[0118] In some of these examples, in step S10, in the reaction solution of the polymerization reaction, the concentration of the norbornene monomer is 0.1 mol / L to 1.0 mol / L.

[0119] In some of these examples, in step S10, in the reaction solution of the polymerization reaction, the concentration of the catalyst is (1 - 10)×10 -3 mol / L.

[0120] In some of these examples, in step S10, the reaction flask used for the polymerization reaction is soaked and washed in a potassium dichromate cleaning solution, then the salt layer on the inner wall is removed with saturated steam, and finally it is baked in a flame and cooled under nitrogen protection. In this way, the oxygen on the reaction flask wall is removed.

[0121] In some of these examples, in step S10, the polymerization reaction is carried out at room temperature (20°C to 35°C). Further, the time of the polymerization reaction is 0.5 h to 2 h.

[0122] It can be understood that vinyl ethyl ether can be added to terminate the polymerization.

[0123] In some of these examples, in step S10, after the polymerization reaction, it further includes the step of post-treating the reaction solution obtained from the polymerization reaction:

[0124] Separate the organic phase of the reaction solution, extract the obtained organic phase, remove the solvent, and then carry out sedimentation treatment and extraction treatment to obtain an organic compound.

[0125] It can be understood that the obtained organic compound is a poly(norbornene) polymer with a narrow molecular weight distribution.

[0126] In some of these examples, the sedimentation treatment is carried out in methanol, and the extraction treatment is carried out with acetone as the solvent.

[0127] In some of these examples, in the method for preparing an organic compound, the preparation of the norbornene monomer includes step S20:

[0128] The compound represented by formula (IV), the compound represented by formula (V) and the compound represented by formula (VI) are mixed to carry out Suzuki coupling reaction (Suzuki reaction) to prepare norbornene monomer;

[0129]

[0130] Wherein, Y is a halogen atom.

[0131] It can be understood that the compound "Ar-Y" represented by formula (VI) is .

[0132] In some examples, in the compound represented by formula (VI), the halogen atoms include but are not limited to F, Cl, Br, and I; further, the reaction formula of step S20 is:

[0133]

[0134] In some of the examples, in step S20, the Suzuki coupling reaction is carried out under the action of a base and a palladium catalyst; optionally, the base includes but is not limited to at least one of sodium carbonate, potassium carbonate and potassium tert-butoxide; the palladium catalyst includes but is not limited to at least one of tetrakis(triphenylphosphine)palladium and palladium acetate.

[0135] In some of the examples, in step S20, the Suzuki coupling reaction is carried out under the action of potassium carbonate, palladium acetate and tri-tert-butylphosphine.

[0136] In some of the examples, in step S20, the temperature of the Suzuki coupling reaction is 70°C to 80°C.

[0137] In some examples, in step S20, the preparation of the compound represented by formula (VI) includes step S30:

[0138] The compound represented by formula (VII) and the compound represented by formula (VIII) are mixed to carry out a substitution reaction to prepare a compound represented by formula (VI);

[0139]

[0140] Here, Z is a halogen atom.

[0141] It can be understood that in the compound represented by formula (VIII), the halogen atom includes but is not limited to F, Cl, Br, and I; further, the reaction route of step S30 is:

[0142]

[0143] The organic compound provided in the present application has low raw material cost, simple preparation process, can be synthesized in large quantities, and is suitable for industrial production.

[0144] One embodiment of the present application provides the use of the above-mentioned organic compound or the organic compound prepared by the above-mentioned preparation method in preparing a hole transport material.

[0145] One embodiment of the present application provides a hole transport material, comprising the above-mentioned organic compound or the organic compound prepared by the above-mentioned preparation method.

[0146] One 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. The hole transport layer is located between the first electrode and the perovskite light-absorbing layer, and the perovskite light-absorbing layer is located between the hole transport layer and the second electrode. The hole transport layer comprises the above-mentioned hole transport material.

[0147] It can be understood that in the hole transport layer, the above-mentioned organic compound or the organic compound prepared by the above-mentioned preparation method can be used alone as the hole transport material, or the above-mentioned organic compound or the organic compound prepared by the above-mentioned preparation method can be used in combination with other hole transport materials, such as in combination with carbazole-based hole materials (2PACZ, MEO-2PACZ, 4PACz, Me-4PACz, etc.).

[0148] In some examples, in the perovskite solar cell, the perovskite light-absorbing layer ABX 3 crystal structure, ABX 3 The crystal structure is the crystal structure of an organic-inorganic hybrid perovskite material, which is embodied as a cubic or octahedral structure. Among them, A includes at least one of methylammonium (MA), formamidinium (FA), benzylammonium (BA) and cesium (Cs), B includes at least one of lead (Pb), tin (Sn) and copper (Cu), and X includes at least one of bromine (Br), chlorine (Cl) and iodine (I).

[0149] In some examples, in the perovskite solar cell, an electron transport layer is further included, and the electron transport layer is disposed between the perovskite light-absorbing layer and the second electrode. Optionally, the electron transport layer includes but is not limited to at least one of metal oxides, fullerenes and their derivatives, etc.; further, the metal oxides include but are not limited to at least one of tin oxide, zinc oxide, etc.; the fullerenes and their derivatives include at least one of C60, PC61BM, PC71BM, etc.

[0150] In some of these examples, in a perovskite solar cell, at least one of the first electrode and the second electrode is a transparent conductive electrode (transparent conductive oxide TCO), and the other is one of a transparent conductive electrode and a metal electrode; optionally, the transparent conductive electrode includes, but is not limited to, at least one of indium tin oxide (ITO), fluorine-doped tin oxide (FTO), indium tin oxide (ITO), aluminum-doped zinc oxide (AZO), antimony-doped tin oxide (ATO), etc.; the metal electrode includes, but is not limited to, at least one of chromium (Cr), gold (Au), silver (Ag), copper (Cu), aluminum (Al), etc.

[0151] In some of these examples, the perovskite solar cell is a p-i-n perovskite solar cell. That is, the first electrode is a transparent conductive electrode.

[0152] See Figure 1 , in some of these examples, the p-i-n perovskite solar cell 100 includes a transparent conductive electrode 110, a hole transport layer 120, a perovskite light-absorbing layer 130, an electron transport layer 140, and a metal electrode 150 that are sequentially stacked.

[0153] One embodiment of the present application provides a method for manufacturing a perovskite solar cell, including the following steps:

[0154] Prepare a hole transport layer on the first electrode; the hole transport layer includes the above-mentioned organic compound.

[0155] Prepare a perovskite light-absorbing layer on a side of the hole transport layer away from the first electrode;

[0156] Prepare a second electrode on a side of the perovskite light-absorbing layer away from the hole transport layer.

[0157] In some of these examples, in the method for manufacturing a perovskite solar cell, the method for preparing the hole transport layer includes a solution method; further, the solution method includes a solution spin-coating method.

[0158] In some of these examples, in the method for manufacturing a perovskite solar cell, preparing the hole transport layer on the first electrode includes the following steps:

[0159] Dissolve the above-mentioned organic compound in an organic solvent to obtain a mixed solution;

[0160] Spin-coat the mixed solution onto the first electrode and anneal.

[0161] Optionally, the organic solvent includes at least one of dimethyl sulfoxide, N,N'-dimethylformamide, toluene, chlorobenzene, and dichloromethane.

[0162] The organic compound provided by the present application has good solubility in dimethyl sulfoxide, N,N'-dimethylformamide, toluene, chlorobenzene, and dichloromethane.

[0163] Optionally, the concentration of the organic compound in the mixed solution is 3 mg / mL to 15 mg / mL.

[0164] Optionally, the rotation speed of spin coating is 4000 rpm to 5000 rpm.

[0165] Optionally, the annealing temperature is 90 °C to 110 °C.

[0166] In some of these examples, in the method for preparing a perovskite solar cell, before preparing the second electrode, it further includes a step of preparing an electron transport layer on the side of the perovskite light-absorbing layer away from the hole transport layer.

[0167] It can be understood that the present application does not limit the methods for preparing the perovskite light-absorbing layer and the electron transport layer, including but not limited to the solution method; nor does it limit the method for preparing the second electrode, including but not limited to evaporation coating.

[0168] In some of these examples, the method for preparing a perovskite solar cell includes the following steps:

[0169] (1) Cleaning: Ultrasonically clean the transparent conductive electrode TCO successively with water, acetone and ethanol (15 - 20 minutes), then use an N 2 air gun to blow dry the solvent remaining on the surface of the transparent conductive electrode, then perform plasma treatment (10 - 15 minutes), and subsequently transfer the transparent conductive electrode TCO to a nitrogen glove box;

[0170] (2) Preparation of the hole transport layer: Dissolve the organic compound in a chlorobenzene solution, drop the prepared mixed solution onto the transparent conductive electrode TCO, spin coat for 20 - 30 seconds, and then anneal at 90 °C to 110 °C (10 - 15 minutes);

[0171] (3) Preparation of the perovskite light-absorbing layer: Cool the obtained TCO / hole transport layer above to room temperature, preheat it at 130 °C to 140 °C (3 - 5 minutes), place the perovskite precursor solution (50 μL - 80 μL) on the surface of the hole transport layer away from ITO, spin coat (20 - 30 seconds) at (3000 rpm - 5000 rpm), and then anneal at 90 °C to 100 °C (10 - 15 minutes) to prepare a perovskite light-absorbing layer; wherein the perovskite precursor solution includes 3-halobenzylammonium iodide, methylammonium chloride and lead iodide; 3-halobenzylammonium iodide is selected from 3-bromobenzylammonium iodide and / or 3-chlorobenzylammonium iodide; the solvent of the perovskite precursor solution includes but is not limited to at least one of DMF and DMSO;

[0172] (4) Preparation of the electron transport layer: Cool the obtained TCO / hole transport layer / perovskite light-absorbing layer to room temperature, and apply (40 μL - 60 μL) of an electron transport solution (PC61BM) with a concentration of (15 mg / mL - 25 mg / mL) onto the surface of the perovskite light-absorbing layer away from the hole transport layer, and spin-coat it at (1000 rpm - 2000 rpm) for (30 - 50 seconds).

[0173] (5) Preparation of the electrode: Place the above substrate in a vacuum evaporation chamber, and evaporate metals (Cr, 6 nm - 10 nm) and (Au, 80 nm - 100 nm) onto the electron transport layer to obtain a reverse-type quasi-two-dimensional perovskite solar cell.

[0174] One embodiment of the present application provides a tandem cell, including the above perovskite cell.

[0175] It can be understood that the tandem cell includes, but is not limited to, two-terminal tandem cells, three-terminal tandem cells, and four-terminal tandem cells. Further, the tandem cell includes, but is not limited to, a perovskite cell stacked with a crystalline silicon cell, a perovskite cell stacked with a perovskite cell, and a perovskite cell stacked with a thin-film cell; the solar thin-film cell includes, but is not limited to, a perovskite solar thin-film cell, a copper indium selenide solar thin-film cell, a gallium arsenide solar thin-film cell, and a cadmium sulfide solar thin-film cell; the crystalline silicon cell includes, but is not limited to, a PERC cell, an IBC cell, a TOPCon cell, and a HIT / HJT cell.

[0176] One embodiment of the present application provides a photovoltaic module, including the above perovskite cell, or a perovskite cell prepared by the above method for preparing a perovskite cell, or the above tandem cell.

[0177] In some examples, the photovoltaic module includes:

[0178] A string of cells, which is formed by connecting multiple above perovskite cells or perovskite cells prepared by the above method for preparing a perovskite cell, or is formed by connecting multiple above tandem cells;

[0179] An encapsulant film, which is used to cover the surface of the string of cells; and

[0180] A cover plate, which is used to cover the surface of the encapsulant film facing away from the string of cells.

[0181] It can be understood that the perovskite cell or the tandem cell is electrically connected in the form of a whole piece or multiple sub-pieces to form multiple strings of cells, and the multiple strings of cells are electrically connected in series and / or in parallel. Further, the perovskite cell or the tandem cell can be a whole-piece cell or a sliced cell, and the sliced cell refers to a cell formed by cutting a complete whole-piece cell through a cutting process.

[0182] In some examples, the multiple strings of cells can be electrically connected through a conductive strip.

[0183] In some of these examples, the encapsulation film includes a first encapsulation layer and a second encapsulation layer. The first encapsulation layer covers one of the front and back surfaces of the battery, and the second encapsulation layer covers the other of the front and back surfaces of the battery. Further, the first encapsulation layer and the second encapsulation layer can each independently include at least one of organic encapsulation films such as polyvinyl butyral (PVB) film, ethylene-vinyl acetate copolymer (EVA) film, polyoctene copolymer (POE) film, and polyethylene terephthalate (PET) film.

[0184] In some of these examples, the cover plate can be a cover plate with a light-transmitting function such as a glass cover plate or a plastic cover plate.

[0185] It can be understood that photovoltaic modules are widely used, such as in the power station field and building integrated photovoltaic (BIPV). In the power station field, they can be laid on a large scale in centralized power stations or distributed power stations for power generation. Building Integrated Photovoltaic (BIPV) is a technology that integrates photovoltaic power generation products into buildings. By designing solar panels into various building decoration materials to replace traditional decoration materials such as glass curtain walls or roof tiles, for example, photovoltaic tile roofs can provide functions such as protecting from wind and rain, and at the same time can serve as a solar power generation system to provide environmentally friendly electricity. Photovoltaic tiles are an important part of rooftop power stations, used to convert the received solar energy into electrical energy to meet the electrical energy needs of daily production and life.

[0186] An embodiment of the present application provides an electrical device including the above-mentioned photovoltaic module.

[0187] It can be understood that the electrical device can be a vehicle, a mobile phone, a portable device, a laptop computer, a ship, a spacecraft, an electric toy, an electric tool, etc. The vehicle can be a fuel vehicle, a gas vehicle, or a new energy vehicle; the spacecraft includes an airplane, a rocket, a space shuttle, a spaceship, etc.; the electric toy includes stationary or mobile electric toys, for example, game consoles, electric vehicle toys, electric ship toys, electric airplane toys, etc.; the electric tool includes metal cutting electric tools, grinding electric tools, assembly electric tools, and railway electric tools, for example, electric drills, electric grinders, electric wrenches, electric screwdrivers, electric hammers, impact electric drills, concrete vibrators, and electric planers, etc. The embodiments of the present application do not impose special restrictions on the above-mentioned electrical devices.

[0188] The following further describes the present application in detail in conjunction with specific embodiments, but the embodiments of the present application are not limited thereto.

[0189] Example 1

[0190] The synthesis route is as follows:

[0191]

[0192] Synthesis of Compound 3: Add compound 1 (7.0 g, 30.0 mmol), compound 2 (2.61 g, 13.6 mmol), 1,10-phenanthroline (0.50 g, 2.8 mmol), copper(I) iodide (0.48 g, 2.5 mmol), and potassium tert-butoxide (13.82 g, 100 mmol) into a 250 mL two-necked reaction flask. Then add 100 mL of toluene. React at 135 °C for 48 h under N 2 conditions. Cool to room temperature, extract with saturated sodium chloride solution and dichloromethane three times repeatedly. Then dry over anhydrous magnesium sulfate, filter, and distill under reduced pressure. Finally, purify by column chromatography (PE:DCM = 15:1) to obtain 4.1 g of yellow compound 3 with a yield of 73%.

[0193] Synthesis of Compound 4: Weigh compound 3 (3.84 g, 10 mmol) and add it into a 500 mL three-necked flask. Then add 30 mL of dry THF. Cool to -78 °C and stir for 10 min under N 2 conditions. Then slowly add n-butyllithium (3.75 mL, 1.00 equiv, 1.6 M in n-hexane) dropwise. React at -78 °C for 1 h. Then add tert-butylpinacol borate (2.75 mL) and continue to react at -78 °C for 1 h. Finally, transfer to room temperature and react for 12 h. Quench the reaction with 50 mL of deionized water, extract with saturated sodium chloride solution and dichloromethane. Dry the organic phase over anhydrous magnesium sulfate, filter, and distill under reduced pressure. Finally, purify by column chromatography (PE:DCM = 15:1) to obtain 3.4 g of white solid compound 4 with a yield of 79%.

[0194] Synthesis of Compound 7: Stir a mixture of compound 5 (4.6 g, 27.5 mmol) and sodium hydride (1.2 g, 50.0 mmol) in dry N,N-dimethylformamide (100 mL) at room temperature under N 2 conditions. After 30 minutes, add compound 6 (4.38 g, 25 mmol). Stir at 155 °C for 12 h. Cool the mixture to room temperature, pour it into water three times, extract the mixture with dichloromethane, dry the mixture over anhydrous magnesium sulfate, filter, evaporate the solvent, purify the crude product by silica gel column chromatography (eluent: hexane / dichloromethane = 2:1, v / v), and concentrate the mixture under reduced pressure to obtain 6.44 g of compound 7 with a yield of 73%.

[0195] Synthesis of compound 9: Raw material 8 (0.28 g, 3 mmol), compound 4 (0.992 g, 2.3 mmol), compound 7 (0.64 g, 2.0 mmol), and potassium carbonate (0.84 g, 6 mmol) were added to a mixture of THF (15 mL) and deionized water (15 mL) under N 2 The mixture was heated to 80°C under the following conditions, and palladium acetate (0.024 g, 0.1 mmol) and tri-tert-butylphosphine (0.1 mL, 10% in n-pentane) were dissolved in dry THF (6 mL) and added to the reaction mixture, and stirring was continued at 80°C for 24 hours. After cooling to room temperature, the mixture was extracted with DCM three times, the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The crude product was purified by column chromatography (PE:DCM=9:1), and finally the solid was recrystallized from a mixture of dichloromethane and petroleum ether (1 / 10, v / v) to obtain 0.63 g of compound 9 with a yield of 50%. The H NMR spectrum of compound 9 is shown in Figure 2 shown.

[0196] Synthesis of PNB-1: Compound 9 (0.3 g, 0.47 mmol) was dissolved in dry THF (1 mL), and the second-generation Grubbs catalyst was quickly injected into the mixture in the bottle to initiate ring-opening polymerization. After stirring at 25°C for 1 hour, vinyl ethyl ether (0.3 mL) was added to the polymer solution to terminate the polymerization. The reaction mixture was precipitated in an acetone solution, filtered, and dissolved in dichloromethane (50 mL). Hydrogen peroxide solution (10 wt% in water, 75 mL) was added to the solution and stirred at room temperature for 1 hour. The organic layer was separated and extracted with Na 2 SO 4 After drying, the product was extracted with DCM as the eluent, and the solvent was removed under vacuum. Finally, the product was precipitated in methanol and extracted with acetone as the solvent for three days to obtain 170 mg of solid PNB-1.

[0197] Example 2

[0198] The synthetic route is as follows:

[0199]

[0200] Synthesis of compound 12: Under nitrogen atmosphere, compound 10 (0.21 g, 1 mmol), compound 9 (0.59 g, 1.2 mmol), CuI (0.04 g, 0.2 mmol), K 2 CO 3(0.28 g, 2 mmol) and anhydrous N,N-dimethylformamide (DMF, 10 mL) were heated to 140 °C for 12 h, and then the mixture was cooled to room temperature, filtered, extracted with ethyl acetate, dried over magnesium sulfate, filtered, evaporated, and purified by column chromatography using petroleum ether as eluent to obtain compound 12 (0.31 g, 85%).

[0201] Synthesis of compound 13: Raw material 8 (0.28 g, 3 mmol), compound 4 (0.992 g, 2.3 mmol, prepared in Example 1), compound 12 (0.72 g, 2.0 mmol), and potassium carbonate (0.84 g, 6 mmol) were added to a mixture of THF (15 mL) and deionized water (15 mL) under N 2 The mixture was heated to 80°C, palladium acetate (0.024 g, 0.1 mmol) and tri-tert-butylphosphine (0.1 mL, 10% in n-pentane) were dissolved in dry THF (6 mL) and added to the reaction mixture, and stirring was continued at 80°C for 24 hours. The mixture was cooled to room temperature, extracted with DCM three times, and anhydrous Mg was added. 2 SO 4 The organic phase was dried, filtered, and distilled under reduced pressure. The crude product was purified by column chromatography (PE:DCM=9:1), and the solid was recrystallized from a mixture of dichloromethane and petroleum ether (1 / 10, v / v) to obtain 0.75 g of compound 13 with a yield of 55%. The H NMR spectrum of compound 13 is shown in Figure 3 shown.

[0202] Synthesis of PNB-2: Compound 13 (0.3 g, 0.44 mmol) was dissolved in dry THF (1 mL), and the second-generation Grubbs catalyst was quickly injected into the mixture in the bottle to initiate ring-opening polymerization. After stirring at 25°C for 1 hour, vinyl ethyl ether (0.3 mL) was added to the polymer solution to terminate the polymerization. The reaction mixture was precipitated in an acetone solution, filtered, and dissolved in dichloromethane (50 mL). Hydrogen peroxide solution (10 wt% in water, 75 mL) was added to the solution and stirred at room temperature for 1 hour. The organic layer was separated and extracted with Na 2 SO 4 After drying, the product was extracted with DCM as the eluent, and the solvent was removed under vacuum. Finally, the product was precipitated in methanol and extracted with acetone as the solvent for three days to obtain 160 mg of solid PNB-2.

[0203] Example 3

[0204] The synthetic route is as follows:

[0205]

[0206] Synthesis of compound 15: Under nitrogen atmosphere, compound 14 (0.18 g, 1 mmol), compound 15 (0.59 g, 1.2 mmol), CuI (0.04 g, 0.2 mmol), K 2 CO 3 (0.28 g, 2 mmol) and anhydrous N,N-dimethylformamide (DMF, 10 mL) were heated to 140 °C for 12 h, and then the mixture was cooled to room temperature, filtered, extracted with ethyl acetate, dried over magnesium sulfate, filtered, evaporated, and purified by column chromatography using petroleum ether as eluent to obtain compound 15 (0.29 g, 85%).

[0207] Synthesis of compound 16: Raw material 8 (0.28 g, 3 mmol), compound 4 (0.992 g, 2.3 mmol, prepared in Example 1), compound 15 (0.72 g, 2.0 mmol), and potassium carbonate (0.84 g, 6 mmol) were added to a mixture of THF (15 mL) and deionized water (15 mL) under N 2 The mixture was heated to 80°C under 4% ethyl acetate and 1% tert-butylphosphine (0.1 mL, 10% in n-pentane) was dissolved in dry THF (6 mL) and added to the reaction mixture, and stirred at 80°C for 24 hours. The mixture was cooled to room temperature, extracted with DCM three times, the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The crude product was purified by column chromatography (PE:DCM=9:1), and finally the solid was recrystallized from a mixture of dichloromethane and petroleum ether (1 / 10, v / v) to obtain 0.75 g of compound 16 with a yield of 55%. The H NMR spectrum of compound 16 is shown in Figure 4 shown.

[0208] Synthesis of PNB-3: Compound 13 (0.3 g, 0.46 mmol) was dissolved in dry THF (1 mL), and the second-generation Grubbs catalyst was quickly injected into the mixture in the bottle to initiate ring-opening polymerization. After stirring at 25°C for 1 hour, vinyl ethyl ether (0.3 mL) was added to the polymer solution to terminate the polymerization. The reaction mixture was precipitated in acetone solution, filtered, and dissolved in dichloromethane (50 mL). Hydrogen peroxide solution (10 wt% in water, 75 mL) was added to the solution and stirred at room temperature for 1 hour. The organic layer was separated and extracted with Na 2 SO 4 After drying, the product was extracted with DCM as the eluent, and the solvent was removed under vacuum. Finally, the product was precipitated in methanol and extracted with acetone as the solvent for three days to obtain 155 mg of solid PNB-3.

[0209] Comparative Example 1

[0210]

[0211] Synthesis of compound 17: Raw material 8 (3 mmol), compound 4 (2.3 mmol, prepared in Example 1), compound 3 (2.0 mmol), and potassium carbonate (6 mmol) were added to a mixture of THF (15 mL) and deionized water (15 mL) under N 2 The mixture was heated to 80°C under the following conditions, and palladium acetate (0.1 mmol) and tri-tert-butylphosphine (0.1 mL, 10% in n-pentane) were dissolved in dry THF (6 mL) and added to the reaction mixture, and the mixture was stirred at 80°C for 24 hours. The mixture was cooled to room temperature, extracted with DCM three times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The crude product was purified by column chromatography (PE:DCM=9:1), and the solid was recrystallized from a mixture of dichloromethane and petroleum ether (1 / 10, v / v) to obtain compound 17.

[0212] Synthesis of compound 18: Compound 17 (0.46 mmol) was dissolved in dry THF (1 mL), and the second-generation Grubbs catalyst was quickly injected into the mixture in the bottle to initiate ring-opening polymerization. After stirring at 25°C for 1 hour, vinyl ethyl ether (0.3 mL) was added to the polymer solution to terminate the polymerization. The reaction mixture was precipitated in an acetone solution, filtered, and dissolved in dichloromethane (50 mL). Hydrogen peroxide solution (10 wt% in water, 75 mL) was added to the solution and stirred at room temperature for 1 hour. The organic layer was separated and extracted with Na 2 SO 4 After drying, the product was extracted with DCM as the eluent, and the solvent was removed under vacuum. Finally, the product was precipitated in methanol and extracted with acetone as the solvent for three days to obtain compound 18.

[0213] The compounds prepared in each embodiment and comparative example were used as hole transport materials to prepare perovskite cells:

[0214] (1) Cleaning: Use deionized water, acetone and ethanol to ultrasonically clean the ITO glass sheet for 15 to 20 minutes, and then use N 2 The residual solvent on the surface of ITO was blown off with an air gun, and then oxygen plasma treatment was performed for 10 to 15 minutes, and then the ITO glass sheet was transferred to a nitrogen glove box;

[0215] (2) Preparation of the hole transport layer: Weigh 3 - 15 mg of the poly(norbornene) - based hole transport material and completely dissolve it in 1 mL of chlorobenzene solution. Take an appropriate amount of the solution and evenly drop it onto the ITO glass substrate, spin - coat it at 4000 - 5000 rpm for 20 - 30 seconds, and then anneal it at 90 - 110 °C for 10 minutes;

[0216] (3) Preparation of the perovskite light - absorbing layer: Cool the obtained ITO / hole transport layer substrate to room temperature, pre - heat it at 130 - 140 °C for 3 - 5 minutes. Take 50 μl of the perovskite solution (a mixture of 3 - chlorobenzylammonium iodide, methylammonium chloride, and lead iodide in DMF and DMSO) and spread it evenly over the ITO / hole transport layer substrate, spin - coat it at 3000 - 5000 rpm for 20 - 30 seconds, and then anneal it at 90 - 100 °C for 10 minutes to prepare the perovskite light - absorbing layer;

[0217] (4) Preparation of the electron transport layer: Cool the obtained ITO / hole transport layer / perovskite substrate to room temperature. Prepare a solution of PC61BM at a concentration of 15 mg / mL, then take 40 μl of the PC61BM solution and spread it evenly over the ITO / hole transport layer / perovskite substrate, spin - coat it at 1000 rpm for 30 - 50 seconds;

[0218] (5) Preparation of the electrode: Place the above - mentioned substrate in a vacuum evaporation chamber, and deposit Cr (6 nm) and Au (80 nm) on the PC61BM layer respectively to obtain the required inverted quasi - two - dimensional perovskite solar cell.

[0219] The hole mobility can be used to define the ability of the HTL to extract holes, and it is one of the important parameters for measuring the performance of HTMs and even the overall performance of the device. The space - charge - limited current method is used to measure the hole mobility. Fabricate ITO / PEDOT:PSS / HTMs to be tested (PNB - 1 or PNB - 2 or PNB - 3 or Compound 18) / MoO 3 / Ag single - hole devices, and determine the film thickness of each layer by a step profiler. Under dark conditions, obtain the J - V characteristic curve of the device through a Keithley 2450 Source - Measure instrument. Perform non - linear fitting analysis on the curve to obtain the carrier mobility of the sample. The test results are shown in Table 1.

[0220] Table 1

[0221]

[0222] As can be seen from Table 1, the energy levels of PNB-1, PNB-2, and PNB-3 match those of the Quasi-2D perovskite material, enabling the formation of good Ohmic contacts, which is conducive to hole transport. Moreover, compared with Comparative Example 1, PNB-1, PNB-2, and PNB-3 have higher hole mobilities and stronger abilities to extract and transport holes.

[0223] Under the illumination condition of AM 1.5G, the speed is 0.02V s -1 The J-V curves of the best devices measured by forward and reverse scans, and the detailed photovoltaic parameters Voc, short-circuit current density (Jsc), fill factor (FF), and PCE are shown in Table 2.

[0224] Table 2

[0225]

[0226] As can be seen from Table 2, compared with the perovskite solar cells prepared using Compound 18 (based on the poly(norbornene) main chain structure with two identical alkoxytriphenylamine side chains) obtained in Comparative Example 1 as the hole transport material, the perovskite solar cells prepared using PNB-1, PNB-2, and PNB-3 (based on the poly(norbornene) main chain structure with different alkoxytriphenylamine and the side chain shown in formula (II)) obtained in the examples have better photovoltaic performance. Among them, PNB-3 has a HOMO energy level aligned with that of the perovskite, and its hole mobility reaches 4.35×10 -4 cm 2 V -1 s -1 , compared with Comparative Example 1, the PNB-3-based perovskite solar cells show more significant improvements in fill factor and power conversion efficiency. The fill factor reaches 81%, and the power conversion efficiency reaches 21.07%.

[0227] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above embodiments are described. However, as long as these combinations of technical features do not conflict, they should all be considered as within the scope described in this specification.

[0228] The above-described embodiments merely represent several implementation manners of the present application, facilitating a specific and detailed understanding of the technical solution of the present application. However, it should not be construed as a limitation on the protection scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present application, several modifications and improvements can still be made, and these all fall within the protection scope of the present application. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments based on the technical solution provided by the present application are all within the protection scope of the appended claims of the present application. Therefore, the protection scope of the patent of the present application shall be subject to the content of the appended claims, and the specification can be used to interpret the content of the claims.

Claims

1. An organic compound, characterized in that The structure of the organic compound is shown in formula (I): Wherein, n is an integer of 10 to 1000, and Ar is selected from one of the structures shown in formula (II): R1~R2 are independently selected from substituted or unsubstituted C1~C 18 alkyl; R3~R8 are independently selected from hydrogen, substituted or unsubstituted C1~C 18 Alkyl, substituted or unsubstituted C1~C 18 Alkoxy, substituted or unsubstituted C1~C 18 Alkylthio, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano, amino and substituted or unsubstituted C6~C 18 One of the aromatic groups; Each occurrence of m is independently selected from integers from 1 to 4; X is selected from a single bond, an oxygen atom, C(R9)2 and NR 10 One of them, R9~R 10 are independently selected from hydrogen and substituted or unsubstituted C1~C 18 alkyl; Each of the substituted substituents is independently selected from one of C1~C4 alkyl, amino, halogen, nitro, hydroxyl, mercapto, carboxyl and cyano.

2. The organic compound according to claim 1, characterized in that R1~R2 are independently selected from substituted or unsubstituted C1~C4 alkyl; and / or, R3 to R8 are independently selected from one of hydrogen, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkoxy, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano and amino; And / or, X is selected from a single bond, an oxygen atom and C(R9)2, and R9 is selected from hydrogen and a substituted or unsubstituted C1-C4 alkyl group.

3. The organic compound according to claim 2, characterized in that R1~R2 are independently selected from one of methyl and ethyl; optionally, R1~R2 are all methyl; and / or, R3 to R8 are independently selected from one of hydrogen, methyl and ethyl; optionally, R3 to R8 are all hydrogen; And / or, R9 is selected from one of methyl and ethyl; optionally, R9 is methyl.

4. The organic compound according to any one of claims 1 to 3, characterized in that The structure of the organic compound is shown in formula (I-1): 。 5. The organic compound according to claim 4, characterized in that Ar is selected from one of the structures represented by formula (II-1) to formula (II-3): 。 6. A method for preparing an organic compound, characterized in that: The following steps are involved: The norbornene monomer is polymerized under the action of a catalyst to prepare an organic compound; The structure of the norbornene monomer is shown in formula (III), and the structure of the organic compound is shown in formula (I): Wherein, n is an integer of 10 to 1000, and Ar is selected from one of the structures shown in formula (II): R1~R2 are independently selected from substituted or unsubstituted C1~C 18 alkyl; R3~R8 are independently selected from hydrogen, substituted or unsubstituted C1~C 18 Alkyl, substituted or unsubstituted C1~C 18 Alkoxy, substituted or unsubstituted C1~C 18 Alkylthio, halogen atom, trifluoromethyl, hydroxyl, mercapto, cyano, amino and substituted or unsubstituted C6~C 18 One of the aromatic groups; Each occurrence of m is independently selected from integers from 1 to 4; X is selected from a single bond, an oxygen atom, C(R9)2 and NR 10 One of them, R9~R 10 are independently selected from hydrogen and substituted or unsubstituted C1~C 18 alkyl; Each of the substituted substituents is independently selected from one of C1~C4 alkyl, amino, halogen, nitro, hydroxyl, mercapto, carboxyl and cyano.

7. The method for preparing an organic compound according to claim 6, characterized in that: The preparation of the norbornene monomer comprises the following steps: The compound represented by formula (IV), the compound represented by formula (V) and the compound represented by formula (VI) are mixed to carry out Suzuki coupling reaction to prepare the norbornene monomer; Wherein, Y is a halogen atom.

8. A hole transport material, characterized in that The method comprises the organic compound as claimed in any one of claims 1 to 5 or the organic compound prepared by the preparation method as claimed in any one of claims 6 to 7.

9. A perovskite battery, characterized in that: It includes a first electrode, a hole transport layer, a perovskite light absorbing layer and a second electrode, wherein the hole transport layer is located between the first electrode and the perovskite light absorbing layer, the perovskite light absorbing layer is located between the hole transport layer and the second electrode, and the hole transport layer includes the hole transport material as claimed in claim 8.

10. A laminated battery, characterized in that: Comprising the perovskite cell as claimed in claim 9.

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