Carbazole organic compound, and preparation method therefor and use thereof

Abstract

Disclosed are a carbazole organic compound, and a preparation method therefor and the use thereof. The carbazole organic compound has a general structural formula as represented by formula (1), and is used as a material for a hole transport layer in a perovskite solar cell.

Description

Carbazole organic compounds and their preparation methods and applications

[0001] This application claims priority to Chinese patent application No. 2023112929840, filed on October 8, 2023, entitled “Carbazole organic compounds, preparation methods and applications thereof,” the entire text of which is hereby incorporated by reference. Technical Field

[0002] The present application relates to the field of organic optoelectronic materials, and in particular to a carbazole organic compound and a preparation method and application thereof. Background Art

[0003] Organic-inorganic hybrid perovskite solar cells (PSCs) are attracting widespread attention as a new type of high-efficiency, low-cost solar cell. They can be efficiently and scalably produced through solution processing methods such as slot coating, spray coating, doctor blade coating, and roll-to-roll. Compared to traditional silicon-based solar cells, organic-inorganic hybrid perovskite solar cells offer advantages such as low manufacturing costs and simplified processing, and hold great commercial promise.

[0004] Thanks to advances in perovskite film formation technology and its own material technologies, the photoelectric conversion efficiency of perovskite solar cells has increased from 3.8% to 25.7% over the past decade. The development of efficient, stable, and low-cost charge transport materials, particularly hole transport materials (HTMs), is crucial for improving the photoelectric conversion efficiency of cells and promoting the commercialization of PSCs. However, currently reported hole transport materials still suffer from insufficient stability and poor wettability, which poses a significant obstacle to the rational design of more effective HTMs.

[0005] Summary of the Invention

[0006] According to various embodiments of the present application, the present application provides a carbazole organic compound, the general structural formula of which is shown in Formula (1):

[0007] Wherein, R1 is selected from one of the following groups:

[0008] R2 is selected from an aryl group having 6 to 15 ring atoms or a heteroaryl group having 5 to 15 ring atoms;

[0009] Each R3 is independently selected from one of the following groups:

[0010] Each R4 is independently selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, -CN, -NH2 or

[0011] * indicates the attachment site.

[0012] In some embodiments, the general structural formula of the carbazole organic compound is shown in Formula (2):

[0013] In some embodiments, the R1 is selected from one of the following groups:

[0014] In some embodiments, the R2 is selected from one of the following groups:

[0015] In some embodiments, the R2 is selected from one of the following groups:

[0016] In some embodiments, each R4 is independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, -CN or -NH2.

[0017] The present application also provides a method for preparing the above-mentioned carbazole organic compound, comprising the following steps:

[0018] The aromatic amine represented by formula (I-1) or the arylphenylboronic acid represented by formula (I-2) and the dibromocarbazole represented by formula (II) are reacted under alkaline conditions to prepare the compound represented by formula (III);

[0019] reacting the compound represented by formula (III) with a brominated aryl ester, brominated aryl phosphate, brominated aryl sulfonate, or brominated aryl cyanoacetate represented by formula (IV) under alkaline conditions to prepare a compound represented by formula (V);

[0020] The compound represented by formula (V) is hydrolyzed by a hydrolysis reaction to prepare a compound represented by formula (1), wherein R1 is selected from one of the following groups:

[0021] or

[0022] The compound represented by formula (III) is reacted with a brominated aryl glycol or brominated aryl thiol represented by formula (IV) under alkaline conditions to prepare a compound represented by formula (1), wherein R1 is selected from one of the following groups:

[0023] in, Each X is independently selected from absence, a single bond, -O or S-;

[0024] X1 is a halogen;

[0025] X2 is halogen, and R5 is selected from one of the following groups:

[0026] The present application also provides a hole transport material, which comprises the carbazole organic compound described above.

[0027] The present application also provides a photoelectric device, comprising stacked functional layers, wherein the material of one or more of the functional layers is selected from the carbazole organic compound or the hole transport material as described above.

[0028] In some embodiments, the optoelectronic device is a perovskite solar cell or module, comprising a stacked conductive glass layer, a hole transport layer, a perovskite light absorbing layer, an electron transport layer and a metal electrode, characterized in that the material of the hole transport layer is selected from the above-mentioned carbazole organic compound or the above-mentioned hole transport material.

[0029] In some embodiments, a hole blocking layer is further provided between the electron transport layer and the metal electrode.

[0030] In some embodiments, the material of the electron transport layer is selected from one or more combinations of [6,6]-phenyl-C61-butyric acid methyl ester, C60 and tin oxide.

[0031] The material of the perovskite light absorbing layer includes a first perovskite material and a second perovskite material;

[0032] The first perovskite material is selected from a combination of one or more lead halide salts and cesium halide salts, and the second perovskite material is selected from a combination of one or more formamidine halide salts and methylamine halide salts.

[0033] In some embodiments, the hole blocking layer is made of a material selected from a combination of one or more of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline and zirconium acetylacetonate.

[0034] In some embodiments, the material of the electrode layer is selected from one or more combinations of silver, copper, conductive oxides, and carbon electrodes.

[0035] In some embodiments, the perovskite solar cell module comprises the perovskite solar cell described above.

[0036] In some embodiments, the optoelectronic device is a light-emitting diode, which comprises a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, wherein the material of the one or more organic functional layers is selected from the carbazole organic compounds described above.

[0037] The details of one or more embodiments of the present application are set forth in the accompanying drawings and the description below. Other features, objects, and advantages of the present application will become apparent from the description, drawings, and claims. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] In order to better describe and illustrate the embodiments and / or examples of the inventions disclosed herein, reference may be made to one or more of the accompanying drawings. The additional details or examples used to describe the accompanying drawings should not be considered to limit the scope of the disclosed inventions, the presently described embodiments and / or examples, and any of the best modes currently understood for these inventions.

[0039] FIG1 is a schematic structural diagram of a perovskite solar cell provided in an embodiment of the present application;

[0040] FIG2 is a schematic structural diagram of another perovskite solar cell provided in an embodiment of the present application. DETAILED DESCRIPTION

[0041] The present application will be further described in detail below with reference to specific embodiments. The present application can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to provide a more thorough and comprehensive understanding of the present application's disclosure.

[0042] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this application pertains. The terms used herein in the specification of this application are for the purpose of describing specific embodiments only and are not intended to limit this application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0043] Where “including,” “having,” and “comprising” are used herein, it is intended to cover a non-exclusive inclusion, and another component may also be added unless a clear limiting term such as “only,” “consisting of,” etc. is used.

[0044] In this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood to indicate or imply relative importance or implicitly specify the number of technical features indicated. Therefore, features specified as "first" or "second" may explicitly or implicitly include more than one such feature.

[0045] The words "preferably", "more preferably", "preferably", "better", etc. in this application refer to embodiments of the present application that may provide certain beneficial effects in certain circumstances. However, other embodiments may also be preferred under the same circumstances or other circumstances. In addition, the statement of one or more preferred embodiments does not imply that other embodiments are not available, nor is it intended to exclude other embodiments from the scope of this application. That is, in this application, "preferably", "more preferably", "preferably", "better", etc. are merely descriptions of implementation methods or examples with better effects, but do not constitute a limitation on the scope of protection of this application.

[0046] In the present application, “further”, “further”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be understood as limiting the scope of protection of the present application.

[0047] In the present application, “above” or “below” includes the number itself, for example, below 1 means less than or equal to 1 (≤1), and above 1 means greater than or equal to 1 (≥1).

[0048] In this application, "one or more combinations" means more than one, such as one, two, or more than two. "Multiple" or "several" means more than two, such as two, three, etc., and "multi-layer" means more than two layers, such as two layers, three layers, etc., unless otherwise specifically defined. In the description of this application, "several" means more than one, such as one, two, etc., unless otherwise specifically defined.

[0049] When a numerical range is disclosed in this application, the above range is considered continuous and includes the minimum and maximum values ​​of the range, as well as every value between such minimum and maximum values. Further, when a range refers to an integer, every integer between the minimum and maximum values ​​of the range is included. In addition, when multiple ranges are provided to describe a feature or characteristic, the ranges can be combined. In other words, unless otherwise indicated, all ranges disclosed herein should be understood to include any and all subranges included therein. And only some numerical ranges are specifically disclosed herein. However, any lower limit can be combined with any upper limit to form an unspecified range; and any lower limit can be combined with other lower limits to form an unspecified range, and similarly, any upper limit can be combined with any other upper limit to form an unspecified range. In addition, each separately disclosed point or single value itself can be combined as a lower limit or upper limit with any other point or single value or with other lower limits or upper limits to form an unspecified range.

[0050] Unless otherwise specified, all steps of the present application may be performed sequentially or randomly. For example, the method includes steps (a) and (b), which means that the method may include steps (a) and (b) performed sequentially, or may include steps (b) and (a) performed sequentially. For example, the method may further include step (c), which means that step (c) may be added to the method in any order. For example, the method may include steps (a), (b) and (c), or may include steps (a), (c) and (b), or may include steps (c), (a) and (b), etc.

[0051] It should be noted that, in the description of the present invention, directional words such as the terms "center", "horizontal", "longitudinal", "length", "width", "thickness", "up", "down", "front", "back", "left", "right", "vertical", "horizontal", "top", "bottom", "inside", "outside", "clockwise", "counterclockwise" and the like indicating directions and positional relationships are based on the directions or positional relationships shown in the accompanying drawings, and are only for the convenience of describing the present invention and simplifying the description, and do not indicate or imply that the device or element referred to must have a specific direction, be constructed and operated in a specific direction, and should not be understood as limiting the specific scope of protection of the present invention.

[0052] When describing positional relationships, unless otherwise specified, when an element, such as a layer, film, or substrate, is referred to as being "on" another layer, it can be directly on the other layer or intervening layers may also be present. Furthermore, when a layer is referred to as being "under" another layer, it can be directly under or one or more intervening layers may also be present. It will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present.

[0053] Unless mentioned otherwise, terms in the singular may include plural forms and should not be construed as having one number.

[0054] The temperature parameters in this application, unless otherwise specified, allow for both constant temperature treatment and treatment within a certain temperature range. The constant temperature treatment allows for temperature fluctuations within the precision range of instrument control.

[0055] The weights of the relevant components mentioned in the examples of this application specification may not only refer to the specific content of each component, but also represent the weight ratio between the components. Therefore, as long as the content of the relevant components in the examples of this application specification is proportionally enlarged or reduced according to the scope disclosed in the examples of this application specification, it is within the scope disclosed in the examples of this application specification. Specifically, the weights described in the examples of this application specification may be mass units known in the chemical industry, such as μg, mg, g, and kg.

[0056] In this application, when referring to a data range, if the unit is followed only by the right endpoint, it means that the units of the left and right endpoints are the same. For example, 800-850nm means that the units of the left endpoint "800" and the right endpoint "850" are both nm (nanometers).

[0057] In this application, "A and B are independently selected from x, y, or z" means that A and B are independent events, and event A does not affect the occurrence of event B. Therefore, when A is selected from x, B can be selected from any of x, y, or z; when A is selected from y, B can be selected from any of x, y, or z; and when A is selected from z, B can be selected from any of x, y, or z. Similarly, in this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R groups, then R can be independently selected from different groups.

[0058] In this application, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0059] In this application, "alkyl" can refer to a linear, branched, and / or cyclic alkyl group. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "C1-9 alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantane, and the like.

[0060] The term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above connected to a parent core structure via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to, methoxy (-O-CH or -OMe), ethoxy (-O-CHCH or -OEt), and tert-butoxy (-OC(CH) or -OtBu).

[0061] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one ring is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to a substituted or unsubstituted aromatic group containing 6 to 40 ring atoms, preferably an aromatic group having 6 to 30 ring atoms, more preferably an aromatic group having 6 to 18 ring atoms, and particularly preferably an aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to, benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0062] "Heteroaryl or heteroaromatic group" means that at least one carbon atom in an aromatic group is replaced by a non-carbon atom, and the non-carbon atom may be a nitrogen atom, an oxygen atom, or a sulfur atom. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to a substituted or unsubstituted heteroaryl group containing 5 to 40 ring atoms, preferably a heteroaryl group having 6 to 30 ring atoms, more preferably a heteroaryl group having 6 to 18 ring atoms, and particularly preferably a heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include, but are not limited to, triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienothiophene, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and derivatives thereof.

[0063] In the present application, "*" connected to a single bond indicates a connection site; in the present application, a single bond connected to a substituent runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R2 is connected to any substitutable position of the benzene ring.

[0064] Thanks to advances in perovskite film formation and materials technology, the photoelectric conversion efficiency of perovskite solar cells (PSCs) has increased from 3.8% to 25.7% over the past decade. The development of efficient, stable, and low-cost charge transport materials, particularly hole transport materials (HTMs), is crucial for improving the photoelectric conversion efficiency of PSCs and advancing their commercialization. Anchor-based self-assembly strategies have been demonstrated to construct efficient hole transport layers for high-performance pin-structured PSCs. This process utilizes molecular HTMs containing anchoring groups (e.g., carboxyl groups) that spontaneously adsorb onto the surface of oxide substrates to form a monolayer. Compared to conventional thick hole transport layers (HTLs) fabricated by spin coating or spray pyrolysis, self-assembled monolayers offer the advantages of minimal material consumption and low parasitic absorption. Furthermore, chemical bath deposition is a low-cost and scalable process that has been successfully applied to small modules as well as large-area perovskite-silicon tandem solar cells. Fundamentally, anchoring groups can significantly influence the adsorption kinetics, loading density, and binding strength of HTM molecules on the substrate, thereby determining the performance and stability of the resulting perovskite solar cell. However, the self-assembled molecular layers reported so far still suffer from insufficient stability and poor wettability, which leaves a major obstacle for the rational design of more effective HTMs.

[0065] In view of the above problems, the present application provides a carbazole organic compound and its preparation method and application, aiming to provide a new type of organic optoelectronic functional material with good hole transport properties and good stability, thereby improving the efficiency and stability of the device.

[0066] The technical solution is as follows:

[0067] A carbazole organic compound, the general structural formula of which is shown in formula (1):

[0068] Wherein, R1 is selected from one of the following groups:

[0069] R2 is selected from an aryl group having 6 to 15 ring atoms or a heteroaryl group having 5 to 15 ring atoms;

[0070] Each R3 is independently selected from one of the following groups:

[0071] Each R4 is independently selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, -CN, -NH2 or

[0072] * indicates the attachment site.

[0073] The carbazole organic compound provided in the present application comprises a carbazole core and specific R1, R2 and R3, wherein the presence of the carbazole group can increase the hole transport performance; the introduction of R1 and R2 can significantly reduce the contact angle, reduce the surface tension, and improve the wettability and stability; the introduction of R3 with large π conjugation can cooperate with the carbazole core to further enhance the hole transport ability.

[0074] In some embodiments, the general structural formula of the carbazole organic compound is shown in Formula (2):

[0075] When R3 is substituted at the 3 or 6 position on carbazole, it is more conducive to improving the hole transport property.

[0076] In some embodiments, the R1 is selected from one of the following groups:

[0077] Compared to carboxylic acid or monohydroxyl, R1 is selected from other groups in the present application:

[0078] The multi-coordinated physical and chemical interaction with the conductive oxide substrate is stronger, and a layer of hole-transporting small molecules can be more effectively formed on the substrate. This allows the organic compound to be anchored to the conductive oxide substrate, increasing the coverage of the molecule on the substrate while passivating the defects of the conductive oxide. This further enhances the stability of the interface, further improving the stability of the device under working conditions. This increases the interaction between the perovskite and the hole-transporting material, further reduces the contact angle, and increases the wettability of the perovskite and hole-transporting layers, which is conducive to the preparation of large-area perovskite solar cell components or modules.

[0079] In some embodiments, the R2 is selected from one of the following groups:

[0080] In some embodiments, the R2 is selected from one of the following groups:

[0081] In the present application, each R3 is independently selected from one of the following groups:

[0082] In some embodiments, each R3 is independently selected from one of the following groups:

[0083] In some embodiments, each R4 is independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, -CN, or -NH2. Further, each R4 is independently selected from hydrogen, methyl, methoxy, -CN, or -NH2.

[0084] In some embodiments, the carbazole organic compound described in the present application has any of the following structures:

[0085] The present application also provides a method for preparing the above-mentioned carbazole organic compound, comprising the following steps:

[0086] The aromatic amine represented by formula (I-1) or the arylphenylboronic acid represented by formula (I-2) and the dibromocarbazole represented by formula (II) are reacted under alkaline conditions to prepare the compound represented by formula (III);

[0087] reacting the compound represented by formula (III) with a brominated aryl ester, brominated aryl phosphate, brominated aryl sulfonate, or brominated aryl cyanoacetate represented by formula (IV) under alkaline conditions to prepare a compound represented by formula (V);

[0088] The compound represented by formula (V) is hydrolyzed by a hydrolysis reaction to prepare a compound represented by formula (1), wherein R1 is selected from one of the following groups: or

[0089] The compound represented by formula (III) is reacted with a brominated aryl glycol or brominated aryl thiol represented by formula (IV) under alkaline conditions to prepare a compound represented by formula (1), wherein R1 is selected from one of the following groups:

[0090] in, Each X is independently selected from absence, a single bond, -O- or -S-;

[0091] X1 is a halogen;

[0092] X2 is halogen, and R5 is selected from one of the following groups:

[0093] It can be understood that if X does not exist, then (I-1) means express If X is a single bond, then (I-1) represents express

[0094] It is understood that X1 is a halogen, that is, X1 is selected from F, Cl, Br or I, preferably Br.

[0095] It is understood that X2 is a halogen, that is, X2 is selected from F, Cl, Br or I, preferably Br.

[0096] It is understood that the brominated aryl compound represented by (IV) is selected from brominated aryl esters, brominated aryl phosphates, brominated aryl sulfonates, brominated aryl glycols, brominated aryl thiols, or brominated aryl cyanoacetates. For ester compounds, a further hydrolysis reaction is required to prepare the carbazole organic compound represented by formula (1), while for alcohol compounds, no hydrolysis step is required.

[0097] In some embodiments, the reaction conditions for preparing the compound of formula (III) include:

[0098] The molar ratio of the arylphenylboronic acid represented by formula (I) to the dibromocarbazole represented by formula (II) is 1:(2-4), and the base is selected from a combination of one or more of sodium methoxide, sodium ethoxide and sodium tert-butoxide.

[0099] The molar ratio of the aromatic amine represented by formula (I) to the dibromocarbazole represented by formula (II) is 1:(2-4), and the base is selected from a combination of one or more of sodium methoxide, sodium ethoxide and sodium tert-butoxide.

[0100] In some embodiments, the reaction conditions for preparing the compound of formula (V) include:

[0101] The ratio of 1:(1 to 3) of the compound represented by formula (III) and the brominated aryl compound represented by formula (IV) is 1:(1 to 3), and the brominated aryl compound represented by (IV) is selected from brominated aryl esters, brominated aryl phosphates, brominated aryl sulfonates or brominated aryl cyanoacetates.

[0102] In some embodiments, the hydrolysis reaction comprises hydrolysis under alkaline conditions. Furthermore, the molar ratio of the compound represented by formula (V) to the base is 1:(2-5). Furthermore, the base used in the hydrolysis reaction is selected from a combination of one or more of lithium hydroxide, sodium hydroxide, and potassium hydroxide.

[0103] In some embodiments, the reaction conditions for preparing the compound of formula (V) include:

[0104] The ratio of 1:(1-3) of the compound represented by formula (III) and the brominated aryl compound represented by formula (IV) is:(1-3), and the brominated aryl compound represented by (IV) is selected from brominated aryl glycol or brominated aryl thiol.

[0105] This application also provides the application of the above-mentioned carbazole organic compound. The technical solution is as follows:

[0106] A hole transport material comprises the carbazole organic compound described above.

[0107] A photoelectric device comprises stacked functional layers, wherein the material of one or more functional layers is selected from the above-mentioned carbazole organic compound or the above-mentioned hole transport material.

[0108] The carbazole organic compound described above is used in perovskite solar cells: ① Introducing R1 and R2 (such as aromatic carboxylic acid, aromatic phosphoric acid, aromatic sulfuric acid, or aromatic phenol) as anchoring groups, through multi-coordinate synergistic physical and chemical interactions with the conductive oxide (TCO) substrate, can effectively form a hole-transporting small molecule interface on the substrate, anchoring the organic compound to the conductive oxide substrate, improving the molecule's coverage on the substrate, and passivating the defects of the conductive oxide. In addition, due to the strong interaction between R1 and the conductive oxide substrate, the interfacial stability is enhanced, thereby improving the stability of the device under operating conditions. ② Introducing a series of aromatic conjugated groups R3 on the side arms of the carbazole core can cooperate with the carbazole core to improve the molecule's hole extraction performance, regulate the interface energy level, and make it more compatible with the valence band of the perovskite, thereby improving its hole extraction ability. ③ Introducing large polar groups increases the interaction between the perovskite and the hole-transporting material, reduces the contact angle, and increases the wettability of the perovskite and the hole-transporting layer, which is conducive to the preparation of large-area perovskite solar cell components or modules.

[0109] That is, the use of the carbazole organic compounds described in this application in perovskite solar cells can simultaneously improve device stability and efficiency, reduce synthesis costs, and is expected to be used in large-area perovskite solar cell modules.

[0110] In some embodiments, the optoelectronic device is a perovskite solar cell or module, or a light emitting diode. A detailed description of the optoelectronic device is as follows:

[0111] A perovskite solar cell comprises a stacked conductive glass layer, a hole transport layer, a perovskite light absorbing layer, an electron transport layer and a metal electrode, characterized in that the material of the hole transport layer is selected from the above-mentioned carbazole organic compound or the above-mentioned hole transport material.

[0112] FIG1 is a schematic diagram of the structure of a perovskite solar cell according to an embodiment of the present application, wherein 101 represents a glass substrate, 102 represents a TCO, 103 represents a hole transport layer, 104 represents a perovskite light absorbing layer, 105 represents an electron transport layer, and 106 represents a metal electrode.

[0113] In some embodiments, the material of the electron transport layer is selected from one or more combinations of [6,6]-phenyl-C61-butyric acid methyl ester, C60 and tin oxide.

[0114] The material of the perovskite light absorbing layer includes a first perovskite material and a second perovskite material;

[0115] The first perovskite material is selected from a combination of one or more lead halide salts and cesium halide salts, and the second perovskite material is selected from a combination of one or more formamidine halide salts and methylamine halide salts.

[0116] Furthermore, the material of the perovskite light absorption layer is a mixture of the first perovskite material and the second perovskite material in a mass ratio of (0.01-99.99):1. Preferably, the material of the perovskite light absorption layer is a mixture of the first perovskite material and the second perovskite material in a mass ratio of (1-10):1.

[0117] In some embodiments, a hole blocking layer is further provided between the electron transport layer and the metal electrode.

[0118] FIG2 is a schematic diagram of another structure of a perovskite solar cell shown in an embodiment, wherein 201 represents a glass substrate, 202 represents a TCO, 203 represents a hole transport layer, 204 represents a perovskite light absorbing layer, 205 represents an electron transport layer, 206 represents a hole blocking layer, and 207 represents a metal electrode.

[0119] In some embodiments, the hole blocking layer is made of a material selected from a combination of one or more of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline and zirconium acetylacetonate.

[0120] In some embodiments, the material of the electrode layer is a combination of one or more of silver, copper, conductive oxide and carbon electrode.

[0121] The present application also provides a method for preparing the perovskite solar cell as described above, comprising the following steps:

[0122] preparing a hole transport layer on a substrate;

[0123] preparing a perovskite light absorbing layer on the hole transport layer;

[0124] preparing an electron transport layer on the perovskite light absorbing layer;

[0125] A metal electrode layer is prepared on the electron transport layer.

[0126] In some embodiments, the method for preparing a perovskite solar cell comprises the following steps:

[0127] dissolving a carbazole organic compound in a solvent to prepare an organic hole transport material solution, and coating the organic hole transport material solution on a substrate to prepare a hole transport layer;

[0128] preparing a perovskite precursor solution, and coating the perovskite precursor solution on the hole transport layer to prepare a perovskite light absorbing layer;

[0129] preparing an electron transport material solution and coating it on the perovskite light absorbing layer to prepare an electron transport layer;

[0130] A metal electrode layer is prepared on the electron transport layer.

[0131] For a perovskite solar cell containing a hole blocking layer, the preparation method thereof comprises the following steps:

[0132] dissolving a carbazole organic compound in a solvent to prepare an organic hole transport material solution, and coating the organic hole transport material solution on a substrate to prepare a hole transport layer;

[0133] preparing a perovskite precursor solution, and coating the perovskite precursor solution on the hole transport layer to prepare a perovskite light absorbing layer;

[0134] preparing an electron transport material solution and coating it on the perovskite light absorbing layer to prepare an electron transport layer;

[0135] preparing a hole blocking material solution and coating it on the electron transport layer to prepare a hole blocking layer;

[0136] A metal electrode layer is formed on the hole blocking layer.

[0137] In some embodiments, the organic hole transport material solution is prepared by dissolving the carbazole organic compound in one or a mixed solvent of chlorobenzene, toluene, ethyl acetate, chloroform, isopropanol, ethanol, tetrahydrofuran, N,N-dimethylformamide, and stirring to dissolve the organic hole transport material, wherein the mass volume ratio of the carbazole organic compound to the solvent is 2 mg: (1 to 3) mL.

[0138] In some embodiments, the perovskite precursor solution is prepared by dissolving 10 mg of methylamine hydrochloride, 8 mg of methylamine hydrobromide, 28.8 mg of lead bromide, 16.7 mg of cesium iodide, 235.25 mg of formamidine hydroiodide and 687.4 mg of lead iodide in 1 ml to 2 ml of a mixed solvent of DMF and DMSO, wherein the mixed volume ratio is (4 to 8):1.

[0139] In some embodiments, the electron transport material solution is prepared by dissolving PCBM in chlorobenzene, with the mass volume ratio of the electron transport material to the chlorobenzene being 20 mg:(1-3) mL.

[0140] In some embodiments, C60 or ALD tin oxide may be directly evaporated to form the electron transport layer with a thickness of 10 nm to 50 nm.

[0141] In some embodiments, the hole blocking material solution is prepared by dissolving BCP or zirconium acetylacetonate in isopropanol, with the mass volume ratio of the electron transport material to the isopropanol being 0.5 mg:(1-3) mL.

[0142] In some embodiments, BCP or zirconium acetylacetonate may be directly evaporated to form a hole blocking layer with a thickness of 3 nm to 8 nm.

[0143] The present application also provides a perovskite solar cell module, comprising the perovskite solar cell described above.

[0144] The present application also provides a light-emitting diode, which includes a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, wherein the material of the one or more organic functional layers is selected from the carbazole organic compounds described above.

[0145] The carbazole organic compound described in the present application is used in a light-emitting diode, thereby achieving the purpose of improving the stability and efficiency of the light-emitting diode.

[0146] In some embodiments, the light-emitting diode is an organic light-emitting diode (OLED), which includes a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, and the material of the one or more organic functional layers is selected from the carbazole organic compounds described above.

[0147] It is understood that an OLED also includes a substrate, which can be opaque or transparent. A transparent substrate can be used to manufacture a transparent light-emitting device.

[0148] In some embodiments, the first electrode is an anode and the second electrode is a cathode. Furthermore, the anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light-emitting layer. The cathode can comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the electron injection layer (EIL), the electron transport layer (ETL), or directly into the light-emitting layer (EML).

[0149] OLEDs may further include other functional layers such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0150] In some embodiments, the light-emitting diode is a quantum dot light-emitting diode (QLED), which includes a first electrode, a quantum dot light-emitting layer, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, and the material of the one or more organic functional layers is selected from the carbazole organic compounds described above.

[0151] The present application will be further described in detail below with reference to specific embodiments, but the present application is not limited to the following examples.

[0152] 1. Synthesis of compounds

[0153] synthesis The steps for P1 are as follows:

[0154] Synthesis step 1: Dibromocarbazole (5mmol), diphenylamine (2mmol), Pd(PPh3)4 (116mg, 0.1mmol), sodium tert-butoxide (2.76g, 20mmol) and 70mL of dry toluene were added to a 150mL dry three-necked round-bottom flask in sequence. Under an N2 atmosphere, heat to reflux and stir to react for 24h. After the reaction is completed, cool to room temperature, add CH2Cl2 and deionized water. Repeatedly extract with CH2Cl2 3-4 times, and collect the organic phase in a conical flask. The combined organic layer is dried over anhydrous Na2SO4, and the organic phase is dried under reduced pressure and then separated and purified by silica gel column chromatography (petroleum ether: dichloromethane = 3:1) to obtain an orange solid, namely intermediate 2: 1 H NMR (500 MHz, CDCl3) δ7.57 (d, J = 2.1 Hz, 2H), 7.48 (d, J = 6.5 Hz, 2H), 7.25 (tt, J = 7.8, 1.5 Hz, 8H), 7.08 (dt, J = 7.5, 1.6 Hz, 8H), 7.02 (tt, J = 8.0, 1.4 Hz, 4H), 6.97 (dd, J = 6.5, 2.1 Hz, 2H). The molecular ion peak of the mass spectrum was 502.3382, which was consistent with the theoretical value [M+H + ]C 36 H 28 N3=502.3360 is consistent;

[0155] Synthesis Step 2: Compound 2 (2 mmol), bromophenyl phosphate (3 mmol), Pd(PPh3)4 (115.5 mg, 0.1 mmol), triethylamine (3-5 mL), and 30 mL of dry toluene were added sequentially to a 100 mL dry three-necked round-bottom flask. Under an N2 atmosphere, the mixture was heated to 85°C and stirred for 12 h. After the reaction was completed, the mixture was cooled to room temperature and extracted repeatedly with CH2Cl2 3-4 times. The organic phase was collected in an Erlenmeyer flask. The combined organic layers were dried over anhydrous Na2SO4, and the organic phase was evaporated to dryness under reduced pressure. It was then purified by silica gel column chromatography (dichloromethane:ethyl acetate = 30:1) to obtain a dark red solid, which was intermediate 3: 1 H NMR (500 MHz, CDCl3) δ7.85–7.75 (m, 3H), 7.69–7.63 (m, 2H), 7.61 (d, J = 2.2 Hz, 3H), 7.29–7.18 (m, 8H), 7.12–7.06 (m, 8H), 7.02 (tt, J = 8.0, 1.4 Hz, 4H), 6.97 (dd, J = 7.1, 2.2 Hz, 2H), 4.15 (dq, J = 8.5, 7.0 Hz, 4H), 1.31 (t, J = 6.9 Hz, 6H); the molecular ion peak of the mass spectrum was 714.2835, which was consistent with the theoretical value [M+H + ]C 46 H 41 N3O3P=714.2807 is consistent;

[0156] Synthesis step 3: To a 50 mL dry round-bottom flask, add intermediate 3 (1.0 mmol) and 20 mL of dichloromethane to dissolve, slowly add 2-3 mL of trimethylsilyl bromide, and stir at room temperature for 6-12 hours. After the reaction is complete, remove the solvent under reduced pressure and add 50 mL of methanol. Then add 60 mL of water dropwise until the solution becomes turbid, stir at room temperature for 15 hours, filter and wash with deionized water, and dry to obtain hole transport material P1: 1 H NMR (500 MHz, CDCl3) δ7.87–7.80 (m, 3H), 7.64–7.54 (m, 5H), 7.29–7.19 (m, 8H), 7.12–7.07 (m, 8H), 7.02 (tt, J = 8.0, 1.4 Hz, 4H), 6.97 (dd, J = 7.1, 2.2 Hz, 2H); the molecular ion peak of the mass spectrum was 656.2173, which was consistent with the theoretical value [MH - ]C 42 H 31 N3O3P=656.2181 is consistent.

[0157] By referring to the above method and replacing the raw materials, different hole transport materials P2, P3, P4, P5, P6 and P7 can be prepared:

[0158] Among them, the preparation of P2 requires replacing the raw material diphenylamine in the first step of the P1 synthesis route with dimethylaniline. P3, P4, and P5 are carboxylic acid compounds. The preparation of P3 requires replacing the raw material bromophenyl phosphate in the second step of the P2 synthesis route with bromobenzoate. P4 requires replacing the raw material dimethylaniline in the first step of the P2 synthesis route with dihexylaniline. P5 requires replacing the raw material dimethylaniline in the first step of the P2 synthesis route with carbazole. In addition, when preparing P3 to P5, an ester compound is first obtained, and then the carboxylic acid is prepared by hydrolysis. The hydrolysis step is as follows: to a 50mL dry round-bottom flask, the intermediate (1.0mmol), LiOH (2mmol~5mmol) and 20mL of a mixed solvent of methanol and water (v:v=5:1) are added in sequence. The reaction is stirred at room temperature for 6~12h. After the reaction is completed, the mixture is filtered and washed with deionized water, and then dried to obtain the hole transport materials P3, P4, and P5. To prepare P6, the raw material P1 (step 2) in the synthesis route, bromophenyl phosphate, must be replaced with bromobenzenesulfonate. P7, an alcohol, does not require a hydrolysis step.

[0159] The structural characterization parameters of P2-P7 are as follows:

[0160] P2: 1 H NMR (500 MHz, CDCl3) δ7.86–7.78 (m, 3H), 7.63–7.54 (m, 5H), 7.22 (dd, J = 7.1, 2.2 Hz, 1H), 7.08–7.00 (m, 16H), 6.97 (dd, J = 7.1, 2.2 Hz, 1H), 2.35 (s, 12H); the molecular ion peak of the mass spectrum was 712.2854, which was consistent with the theoretical value [MH - ]C 46 H 39 N3O3P=712.2807 is consistent.

[0161] P3: 1 H NMR (500 MHz, CDCl3) δ8.08–8.00 (m, 2H), 7.71–7.66 (m, 3H), 7.59–7.54 (m, 2H), 7.52 (d, J = 2.1 Hz, 1H), 7.21 (dd, J = 7.1, 2.2 Hz, 1H), 7.11 (dd, J = 7.2, 2.3 Hz, 1H), 7.07–6.97 (m, 16H), 2.35 (s, 12H); the molecular ion peak of the mass spectrum was 676.3067, which was consistent with the theoretical value [MH - ]C 47 H38 N3O2=676.3042 is consistent.

[0162] P4: 1 H NMR (500 MHz, CDCl3) δ8.08–8.02 (m, 2H), 7.71–7.65 (m, 3H), 7.62–7.54 (m, 2H), 7.52 (d, J = 2.1 Hz, 1H), 7.21 (dd, J = 7.1, 2.2 Hz, 1H), 7.18–7.14 (m, 8H), 7.11 (dd, J = 7.1, 2.3 Hz, 1H), 7.06–7.00 (m, 8H), 2.63–2.55 (m, 8H), 1.63–1.51 (m, 8H), 1.37–1.23 (m, 24H), 0.94–0.84 (m, 12H); the molecular ion peak of the mass spectrum was 956.6154, which was consistent with the theoretical value [MH - ]C 67 H 78 N3O2=956.6172 is consistent.

[0163] P5: 1 H NMR (500 MHz, CDCl3) δ8.16–8.12 (m, 4H), 8.08–8.02 (m, 2H), 7.88 (d, J = 2.1 Hz, 1H), 7.83 (d, J = 2.1 Hz, 1H), 7.75 (d, J = 6.5 Hz, 1H), 7.70–7.62 (m, 7H), 7.59 (dd, J = 6.4, 2.2 Hz, 1H), 7.45 (dd, J = 6.5, 2.3 Hz, 1H), 7.38–7.27 (m, 8H); the molecular ion peak of the mass spectrum was 616.2128, which was consistent with the theoretical value [MH - ]C 43 H 26 N3O2=616.2103 is consistent.

[0164] P6: 1 H NMR (500 MHz, CDCl3) δ7.85–7.81 (m, 2H), 7.70 (d, J = 7.1 Hz, 1H), 7.65–7.60 (m, 2H), 7.59–7.53 (m, 2H), 7.52 (d, J = 2.0 Hz, 1H), 7.33–7.25 (m, 8H), 7.21 (dd, J = 7.1, 2.2 Hz, 1H), 7.14–7.08 (m, 9H), 7.08–7.00 (m, 4H); the molecular ion peak of the mass spectrum was 656.2065, which was consistent with the theoretical value [MH - ]C 42 H 30N3O3S=656.2086 is consistent.

[0165] P7: 1 H NMR (500 MHz, CDCl3) δ8.17–8.08 (m, 4H), 7.88 (d, J = 2.1 Hz, 1H), 7.83 (d, J = 2.1 Hz, 1H), 7.75 (d, J = 6.4 Hz, 1H), 7.67–7.62 (m, 5H), 7.59 (dd, J = 6.4, 2.2 Hz, 1H), 7.54–7.49 (m, 2H), 7.45 (dd, J = 6.4, 2.3 Hz, 1H), 7.40–7.23 (m, 8H), 7.01–6.93 (m, 2H), 5.69 (s, 2H); the molecular ion peak of the mass spectrum was 604.2342, which was consistent with the theoretical value [M+H + ]C 43 H 30 N3O=604.2311 is consistent.

[0166] Test Case

[0167] A method for preparing a perovskite solar cell as shown in FIG2 is provided, comprising the following steps:

[0168] (1) The TCO conductive glass was ultrasonically cleaned with deionized water, acetone, and isopropyl alcohol for 15 minutes respectively, and finally dried in a drying oven at 75°C for later use; the dried TCO glass substrate was placed in a UV ozone machine for 5 minutes to remove organic impurities on its surface and optimize its surface wettability;

[0169] (2) Dissolve 1 mg of organic hole transport material P1 in 2 mL of chlorobenzene and stir at room temperature (22 ± 5 °C) until completely dissolved to obtain an organic hole transport material solution; take 30 μL of the organic hole transport material solution and drop it on the treated TCO glass, spin-coating at 5000 rpm for 30 seconds, and place the TCO glass in S1 on a hot plate and heat anneal at 100 °C for 10 minutes to form a hole transport layer;

[0170] (3) Dissolve 722.08 mg of lead iodide and 238.50 mg of iodomethylamine solid in 1 mL of N,N-dimethylformamide (DMF) and stir at room temperature until completely dissolved to obtain a perovskite precursor solution; in a nitrogen glove box, take 30 μL of the perovskite precursor solution and drop it onto the ITO conductive glass that forms the hole transport layer. First, spin coat it at 1000 rpm for 10 seconds, then spin coat it at 5000 rpm for 30 seconds. After 25 seconds of this process, quickly add 125 μL of chlorobenzene, then place the TCO glass on a hot plate and heat and anneal it at 100 °C for 40 minutes to form a perovskite layer.

[0171] (4) Dissolve 20 mg of methanefullerene phenyl-C61-butyric acid methyl ester (PCBM) in 1 mL of chlorobenzene and stir at room temperature to obtain a [6,6]-phenyl-C61-butyric acid methyl ester solution; take 30 μL of the [6,6]-phenyl-C61-butyric acid methyl ester solution and spin-coat it on the ITO conductive glass with a perovskite layer at 3000 rpm for 60 seconds to form an electron transport layer;

[0172] (5) 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; add 40 μL of the hole blocking layer solution dropwise onto the electron transport layer and spin-coat at 5000 rpm for 35 seconds to form a hole blocking layer;

[0173] (6) Transfer the TCO conductive glass with hole blocking layer, PCBM electron transport layer, perovskite layer and hole transport layer to the vacuum coating instrument and wait until the vacuum degree is 3*10 -4 Pa, a silver electrode was evaporated to form a silver electrode with a thickness of 100 nm, thereby obtaining an electrode layer.

[0174] By referring to the above method, the type of hole transport material is changed to prepare perovskite solar cells with different hole transport materials.

[0175] The performance of different perovskite solar cells was tested. The test method was as follows: the current density-voltage curves (J-V curves) of the devices were measured by a source meter (Keithley 2400) under AM 1.5G (100 mW cm) provided by a solar simulator (ABET Sun 3000). –2 ) obtained under illumination, the cell area is 0.08cm 2 Before the test, the light intensity was calibrated by a standard silicon cell and the scanning rate was 10mV / s. The results are shown in Table 1.

[0176] Table 1

[0177] From the data in Table 1, it can be seen that compared with P7, the cells using P1 to P6 as hole transport layers for perovskite solar cells have higher open circuit voltage, fill factor, short circuit current and photoelectric conversion efficiency. In particular, the cells using P1, P2 and P6 as hole transport layers for perovskite solar cells have higher photoelectric conversion efficiency, indicating that the use of monohydroxy or carboxylic acid groups as anchoring groups is less effective than phosphate and sulfonic acid groups, and the monohydroxy anchoring effect is the worst, resulting in the lowest efficiency of the device.

[0178] The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, not all possible combinations of the technical features in the above-mentioned embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0179] The above-described embodiments merely represent several implementation methods of the present application and should not be construed as limiting the scope of the present invention. It should be noted that a person skilled in the art may make various modifications and improvements without departing from the spirit of the present application, and these modifications and improvements fall within the scope of protection of the present application. Therefore, the scope of protection of the present patent application shall be determined by the appended claims.

Claims

1. A carbazole organic compound, characterized in that: Its general structural formula is shown in formula (1): Wherein, R1 is selected from one of the following groups: R2 is selected from an aryl group having 6 to 15 ring atoms or a heteroaryl group having 5 to 15 ring atoms; Each R3 is independently selected from one of the following groups: Each R4 is independently selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, -CN, -NH2 or * indicates the attachment site.

2. The carbazole organic compound according to claim 1, characterized in that: Its general structural formula is shown in formula (2):

3. The carbazole organic compound according to claim 1 or 2, characterized in that: The R1 is selected from one of the following groups:

4. The carbazole organic compound according to any one of claims 1 to 3, characterized in that: The R2 is selected from one of the following groups:

5. The carbazole organic compound according to any one of claims 1 to 4, characterized in that: The R2 is selected from one of the following groups:

6. The carbazole organic compound according to any one of claims 1 to 5, characterized in that: Each R4 is independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, -CN or -NH2.

7. The carbazole organic compound according to any one of claims 1 to 6, characterized in that: Each R4 is independently selected from hydrogen, methyl, methoxy, -CN or -NH2.

8. A method for preparing a carbazole organic compound, characterized in that: The general structural formula of the carbazole organic compound is shown in formula (1): Wherein, R1 is selected from one of the following groups: R2 is selected from an aryl group having 6 to 15 ring atoms or a heteroaryl group having 5 to 15 ring atoms; Each R3 is independently selected from one of the following groups: Each R4 is independently selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, -CN, -NH2 or * indicates the attachment site; The preparation method of the carbazole organic compound comprises the following steps: The aromatic amine represented by formula (I-1) or the arylphenylboronic acid represented by formula (I-2) and the dibromocarbazole represented by formula (II) are reacted under alkaline conditions to prepare a compound represented by formula (III); reacting the compound represented by formula (III) with a brominated aryl ester, brominated aryl phosphate, brominated aryl sulfonate or brominated aryl cyanoacetate represented by formula (IV) under alkaline conditions to prepare a compound represented by formula (V); The compound represented by formula (V) is hydrolyzed by a hydrolysis reaction to prepare a compound represented by formula (1), wherein R1 is selected from one of the following groups: or The compound represented by formula (III) and the brominated aryl glycol or brominated aryl thiol represented by formula (IV) are reacted under alkaline conditions to prepare the compound represented by formula (1), wherein R1 is selected from one of the following groups: in, Each X is independently selected from absence, a single bond, -O- or -S-; X1 is halogen; X2 is halogen, and R5 is selected from one of the following groups:

9. A hole transport material, characterized in that The method comprises the carbazole organic compound according to any one of claims 1 to 7.

10. A photoelectric device, characterized in that: The invention comprises stacked functional layers, wherein the material of one or more of the functional layers is selected from the carbazole organic compound according to any one of claims 1 to 7 or the hole transport material according to claim 9.

11. The optoelectronic device according to claim 10, characterized in that: The optoelectronic device is a perovskite solar cell or module, comprising a stacked conductive glass layer, a hole transport layer, a perovskite light absorbing layer, an electron transport layer and a metal electrode, wherein the material of the hole transport layer is selected from the carbazole organic compound described in any one of claims 1 to 7 or the hole transport material described in claim 9.

12. The optoelectronic device according to claim 11, characterized in that: A hole blocking layer is also provided between the electron transport layer and the metal electrode.

13. The optoelectronic device according to claim 12, characterized in that: The material of the hole blocking layer is selected from one or more of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline and zirconium acetylacetonate.

14. The optoelectronic device according to claim 12 or 13, characterized in that: The material of the electrode layer is selected from one or more combinations of silver, copper, conductive oxide and carbon electrode.

15. The optoelectronic device according to any one of claims 11 to 14, characterized in that: The material of the electron transport layer is selected from one or more combinations of [6,6]-phenyl-C61-butyric acid methyl ester, C60 and tin oxide.

16. The optoelectronic device according to any one of claims 11 to 15, characterized in that: The material of the perovskite light absorption layer includes a first perovskite material and a second perovskite material; The first perovskite material is selected from a combination of one or more of lead halide salts and cesium halide salts, and the second perovskite material is selected from a combination of one or more of formamidine halide salts and methylamine halide salts.

17. The optoelectronic device according to claim 10, characterized in that: The photoelectric device is a light emitting diode, comprising a first electrode, a second electrode, and one or more functional layers between the first electrode and the second electrode, wherein the material of the one or more functional layers is selected from the carbazole organic compound according to any one of claims 1 to 7.

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