Pyrenyl aniline derivative oligomer with bridging structure, preparation method of pyrenyl aniline derivative oligomer and application of pyrenyl aniline derivative oligomer in organic electronic device

Abstract

The invention belongs to the field of organic photoelectric materials, and discloses a pyrenyl aniline derivative oligomer with a bridging structure, a preparation method of the pyrenyl aniline derivative oligomer and application of the pyrenyl aniline derivative oligomer in organic electronic devices. The molecular structural formula of the pyrenyl aniline derivative oligomer is as follows: R1 is a saturated or unsaturated alkyl chain of 1-100 carbons, a benzene ring, a saturated or unsaturated heteroring, sulfur, nitrogen, oxygen and phosphorus atoms, R2 is a hydrogen atom or an aniline derivative group, n is equal to 2-200, and m is equal to 2-50. The pyrenyl aniline derivative oligomer with the bridging structure has excellent hole transport capacity, a perovskite solar cell prepared by using the pyrenyl aniline derivative oligomer as a hole transport material shows more excellent photoelectric conversion efficiency than a structural unit of the perovskite solar cell, and the pyrenyl aniline derivative oligomer can be applied to the field of organic electronic devices such as the perovskite solar cell and an organic photoelectric device.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, specifically relating to a class of pyrene-aniline-derived oligomers with bridging structures, their preparation methods, and their applications in organic electronic devices. Background Technology

[0002] Perovskite solar cells (PSCs), as an emerging photovoltaic technology, have attracted widespread attention from academia and industry due to their advantages such as high photoelectric conversion efficiency, low cost, and solution-processability. In this technology, hole transport materials (HTMs) are the core component of the device, directly determining the hole extraction and transport efficiency, interface stability, and ultimately, the energy conversion performance. Currently, 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spirodifluorene (Spiro-OMeTAD) is the most representative organic hole transport material, but it suffers from low hole mobility, dependence on hygroscopic dopants, complex synthesis steps, and high cost, severely hindering the commercialization of perovskite solar cells.

[0003] To overcome the limitations of Spiro-OMeTAD, researchers are dedicated to developing novel high-performance hole transport materials (HTMs). Their design philosophy focuses on efficient charge extraction capabilities, good energy level matching, excellent interface passivation, and simplified fabrication processes. In terms of molecular design strategies, conjugated polymers with donor-acceptor structures, phthalocyanine molecules with planar large π-systems, and triphenylamine-based derivatives have shown significant potential. Aniline derivatives, represented by triphenylamine, possess outstanding electron-donating properties and have attracted widespread attention in the design of hole transport materials. By rationally selecting chemical building blocks and precisely controlling the molecular structure, their hole transport performance can be effectively optimized, thereby achieving efficient charge extraction and transport in perovskite solar cells. Furthermore, the triphenylamine unit is highly responsive to light and electrical stimulation, and can generate free radical species under corresponding conditions, further enhancing hole mobility and providing a new approach for the dynamic control of material performance.

[0004] Pyrene, a polycyclic aromatic hydrocarbon with high charge mobility and good luminescence properties, is often considered a chemical byproduct, yet it shows significant potential in the construction of functional materials. Its rigid conjugated planar structure facilitates charge delocalization and transport, thus it is widely used in the fabrication of high-performance organic electronic devices, such as organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). Introducing pyrene into hole transport material systems not only helps improve carrier mobility but also provides new molecular design ideas for modulating the photoelectric properties of materials. Summary of the Invention

[0005] The purpose of this invention is to provide a class of pyrene aniline-derived oligomers with bridging structures. These pyrene aniline-derived oligomers with bridging structures have advantages such as high thermal stability, efficient hole transport capability, high performance, and low cost.

[0006] Another object of the present invention is to provide a method for preparing the above-mentioned pyrene aniline-derived oligomers having a bridging structure.

[0007] Another object of the present invention is to provide an application of the above-mentioned pyrene-aniline-derived oligomers with bridging structures. Applying pyrene-aniline-derived oligomers as hole transport materials to perovskite solar cells significantly improves their overall performance, such as photoelectric conversion efficiency, current density, and short-circuit current, which is of great significance for breakthroughs in the field of organic electronic devices.

[0008] To achieve the objectives of this invention, the following solution is provided: A class of pyrene-aniline-derived oligomers with bridging structures have the following general molecular formula:

[0009] Wherein, R1 is a saturated or unsaturated alkyl chain, benzene ring, saturated or unsaturated heterocyclic ring, sulfur, nitrogen, oxygen, or phosphorus atom with 1 to 100 carbon atoms, and R2 is an aniline derivative group, n=2~200, m=2~50.

[0010] Preferably, the structure of the aniline derivative group is as follows: .

[0011] Preferably, R1 is: .

[0012] Preferably, the molecular structural formula of the pyrene-aniline-derived oligomer with the bridging structure is as follows: .

[0013] The preparation method of the pyrene aniline-derived oligomer with the bridging structure is to add the pyrene aniline derivative, the bridging monomer and the base to the solvent, reflux and stir at 70~150℃ under a protective atmosphere until the reaction is complete, and then extract and purify to obtain the product.

[0014] Preferably, the bridging monomer is a saturated or unsaturated alkyl chain, benzene ring, saturated or unsaturated heterocyclic ring, sulfur, nitrogen, oxygen, or phosphorus atom with 1 to 100 carbon atoms; the base is one or more of potassium carbonate, cesium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, potassium tert-butoxide, and sodium tert-butoxide; the solvent is one or more of toluene, ethanol, water, tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, and dimethyl sulfoxide; the protective atmosphere is argon or nitrogen; and the equimolar ratio of the pyrene aniline derivative, the bridging monomer, and the base is (1 to 4): 1: (2 to 8).

[0015] Preferably, the structure of the pyrene aniline derivative is as follows: .

[0016] Application of the pyrene aniline-derived oligomers with bridging structures in organic electronic devices.

[0017] Preferably, the organic electronic device is a perovskite solar cell, an organic light-emitting diode, or an organic field-effect transistor.

[0018] The synthetic route for preparing the pyrene aniline derivative is as follows: .

[0019] The synthetic route for the pyrene-aniline-derived oligomers with the bridging structure is as follows: .

[0020] This invention modifies pyrene at four sites (1-, 3-, 6-, and 8-) with aniline derivative groups (such as diphenylamine, triphenylamine, methoxytriphenylamine, carbazole, phenothiazine, etc.), and simultaneously connects two or more hole transport material structural units in series at the 2- and 7- sites using bridging structural units, thus preparing a class of pyrene-based aniline-derived oligomers with bridging structures. Due to the high-performance hole transport capability of pyrene-based aniline derivatives, by controlling the type of bridging structure, chain length, and steric hindrance, the aggregation morphology of the target molecule can be efficiently adjusted, thereby improving charge transport capability, especially hole transport capability. Hole transport layers are a crucial component of organic electronic device structures, playing a vital role in improving overall device performance. Based on molecular structure and theoretical calculations, it is inferred that these compounds possess excellent hole transport properties. Furthermore, the implementation of preferred examples further demonstrates that the pyrene-aniline-derived oligomers with bridging structures of this invention exhibit superior hole transport capabilities, solubility, and film-forming properties. They are suitable as hole transport materials for the fabrication of perovskite solar cells, organic light-emitting diodes, organic field-effect transistors, and other organic electronic devices, thereby improving the overall performance of the devices.

[0021] Compared with the prior art, the present invention has the following beneficial effects: 1. The pyrene-aniline-derived oligomers with bridging structures of the present invention have advantages such as high efficiency of hole transport, high performance, and low cost. When used as hole transport materials in perovskite solar cells, their overall performance is significantly improved, such as photoelectric conversion efficiency, current density, and short-circuit current. This is of great significance for the development and breakthrough of organic electronic devices containing hole transport layers (such as perovskite cells, organic light-emitting diodes, organic field-effect transistors, etc.).

[0022] 2. The pyrene aniline derivative oligomer with a bridging structure of the present invention combines multiple pyrene aniline derivative unit structures. This material has good hole transport capability and film-forming properties, and is suitable as a hole transport layer for the preparation of organic electronic devices such as perovskite solar cells. It allows for the selection of materials with more matching energy levels according to the perovskite material of the electrode material, and is low in cost, making it suitable for large-scale production and commercial application. Attached Figure Description

[0023] Figure 1 The 1H NMR spectrum of pyrene aniline derivative 1 prepared in Example 1; Figure 2 The carbon NMR spectrum of pyrene aniline derivative 1 obtained in Example 1; Figure 3 High-resolution mass spectra of pyrene aniline derivative 1 prepared in Example 1; Figure 4The 1H NMR spectrum of pyrene aniline-derived oligomer A with a 1,9-nonyl-bridged structure prepared in Example 2; Figure 5 The carbon NMR spectrum of pyrene aniline-derived oligomer A with a 1,9-nonyl-bridged structure obtained in Example 2; Figure 6 The high-resolution mass spectra of pyrene aniline-derived oligomer A with a 1,9-nonyl-bridged structure prepared in Example 2 are shown. Figure 7 The 1H NMR spectrum of pyrene aniline-derived oligomer B with a 1,10-decyl-bridged structure prepared in Example 3; Figure 8 The carbon NMR spectrum of pyrene aniline-derived oligomer B with a 1,10-decyl-bridged structure obtained in Example 3; Figure 9 High-resolution mass spectra of pyrene aniline-derived oligomer B with a 1,10-decyl bridging structure prepared in Example 3; Figure 10 The 1H NMR spectrum of pyrene aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure obtained in Example 4; Figure 11 The carbon NMR spectrum of pyrene aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure obtained in Example 4; Figure 12 High-resolution mass spectra of pyrene aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure obtained in Example 4; Figure 13 This is an example of a perovskite solar cell fabricated using pyrene-aniline-derived oligomer A with a 1,9-nonyl-bridged structure as the hole transport layer, as described in Application Example 1. J - V curve; Figure 14 Here is a SEM image of the perovskite solar cell fabricated using pyrene-aniline-derived oligomer B with a bridging structure as the hole transport layer in Application Example 2. Figure 15 For example 2, a perovskite solar cell was fabricated using pyrene-aniline-derived oligomer B with a 1,10-decyl-bridged structure as the hole transport layer. J - V curve; Figure 16 For example 3, a perovskite solar cell was fabricated using pyrene-aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure as the hole transport layer. J - V curve; Figure 17The steady-state output efficiency of perovskite solar cells fabricated using pyrene-aniline-derived oligomers A, B, and C with bridging structures as hole transport layers in Examples 1-3 is shown. Figure 18 The steady-state output short-circuit current of the perovskite solar cells prepared using pyrene-aniline-derived oligomers A, B, and C with bridging structures as hole transport layers in Application Examples 1-3 is shown. Detailed Implementation

[0024] The present invention will be further described below with reference to specific embodiments, but these should not be construed as limiting the invention. Unless otherwise specified, the technical means used in the embodiments are conventional means well known to those skilled in the art. Unless otherwise specified, the reagents, methods, and equipment used in the present invention are conventional reagents, methods, and equipment in this technical field.

[0025] Example 1 2-Hydroxy-1,3,6,8-Tetrasubstituted (4,4'-Dimethoxyaniline)-pyrene (1) Under nitrogen protection, 2-hydroxy-1,3,6,8-tetrabromopyrene (1 eq.), 4,4'-dimethoxy-4''-boronic acid triphenylamine (6 eq.), potassium carbonate (20 eq.), and tetra(triphenylphosphine)palladium (0.1 eq.) were added to a double-necked flask and dissolved in 10 mL of a mixed solution of toluene, ethanol, and water in a volume ratio of 5:1:1. The mixture was heated to reflux at 90 °C for 24 h. After the reaction was completed, the mixture was cooled to room temperature, washed three times with dichloromethane, and then extracted with saturated brine. After rotary evaporation, the mixture was separated by column chromatography to obtain 2-hydroxy-1,3,6,8-tetrasubstituted (4,4'-dimethoxyaniline)-pyrene (1) with a yield of approximately 70%. The synthetic route is shown in formula (1). Figure 1-3 The 1H NMR spectra of the pyrene aniline derivative 1 prepared in this embodiment are shown below. 1 H NMR, carbon NMR ( 13 C10 NMR and high-resolution mass spectrometry (HRMS). From Figure 1-3 It can be seen that the pyrene aniline derivative, namely 2-hydroxy-1,3,6,8-tetrasubstituted (4,4'-dimethoxyaniline)-pyrene (1), was successfully prepared.

[0026]

[0027] Equation (1).

[0028] Example 2: Pyrene aniline-derived oligomer A with a 1,9-nonyl-bridged structure

[0029] Equation (2) Under nitrogen protection, 2-hydroxy-1,3,6,8-tetrasubstituted (4,4'-dimethoxyaniline)-pyrene (1) (2 eq.), 1,9-dibromononane (1 eq.) and cesium carbonate (2 eq.) from Example 1 were dissolved in 10 mL DMF and heated to reflux at 120 °C for 24 h. After the reaction was completed, the mixture was cooled to room temperature, washed three times with dichloromethane, extracted with saturated brine, and separated by rotary evaporation and column chromatography to obtain pyrene-aniline-derived oligomer A with a 1,9-nonyl-bridged structure in a yield of approximately 70%. The synthetic route is shown in formula (2). Figure 4-6 These are respectively the pyrene-aniline-derived oligomer A prepared in this embodiment. 1 H NMR spectrum, 13 C NMR and HRMS plots. From Figure 4-6 It can be seen that pyrene-aniline-derived oligomer A with a 1,9-nonyl-bridged structure was successfully prepared.

[0030] Example 3: Pyrene aniline-derived oligomer B with a 1,10-decyl-bridged structure

[0031] Equation (3) Under nitrogen protection, 2-hydroxy-1,3,6,8-tetrasubstituted (4,4'-dimethoxyaniline)-pyrene (1) (2. eq.), 1,10-diiododecane (1 eq.) and cesium carbonate (2 eq.) from Example 1 were dissolved in 10 mL of DMF and heated under reflux at 120 °C for 24 h. After the reaction was completed, the mixture was cooled to room temperature, washed three times with dichloromethane, extracted with saturated brine, and separated by rotary evaporation and column chromatography to obtain pyrene-aniline-derived oligomer B with a 1,10-decyl-bridged structure, with a yield of approximately 67%. The synthetic route is shown in formula (3). Figure 7-9 These are the pyrene aniline-derived oligomer B obtained in this embodiment. 1 H NMR image 13 CNMR and HRMS plots. From Figure 7-9 It can be seen that pyrene-aniline-derived oligomer B with a 1,10-decyl-bridged structure was successfully prepared.

[0032] Example 4: Pyrene aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure Under nitrogen protection, 2-hydroxy-1,3,6,8-tetrasubstituted (4,4'-dimethoxyaniline)-pyrene (1) (2 eq.), 1,13-dibromotridecane (1 eq.) and cesium carbonate (2 eq.) from Example 1 were dissolved in 10 mL DMF and heated to reflux at 120 °C for 24 h. After the reaction was completed, the mixture was cooled to room temperature, washed three times with dichloromethane, extracted with saturated brine, and separated by rotary evaporation and column chromatography to obtain pyrene-aniline-derived oligomer C with a 1,13-tridecyl-bridged structure, with a yield of approximately 63%. The synthetic route is shown in formula (4). Figure 10-12 These are the pyrene aniline-derived oligomer C obtained in this embodiment. 1 HNMR image 13 C NMR and HRMS plots. From Figure 10-12 It can be seen that pyrene aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure was successfully prepared.

[0033]

[0034] Equation (4).

[0035] Example 5: Pyrene aniline-derived oligomer D with a 1,3,5-tris(bromononyl)phenyl-bridged structure Under nitrogen protection, 2-hydroxy-1,3,6,8-tetrasubstituted (4,4'-dimethoxyaniline)-pyrene (1) (500 mg, 0.34 mmol), 1,3,5-tris(bromononyl)benzene (690 mg, 1 mmol), and cesium carbonate (650 mg, 2 mmol) from Example 1 were dissolved in 15 mL of DMF and heated to reflux at 120 °C for 24 h. After the reaction was completed, the mixture was cooled to room temperature, washed three times with dichloromethane, extracted with saturated brine, and separated by rotary evaporation and column chromatography to obtain pyrene-aniline-derived oligomer D with a 1,3,5-tris(bromononyl)phenyl-bridged structure, with a yield of approximately 50%. The synthetic route is shown in formula (5).

[0036] Equation (5).

[0037] Application Example 1: Perovskite Solar Cells 1. Indium tin oxide (ITO) conductive glass was selected as the substrate and ultrasonically cleaned sequentially with acetone, ethanol, and deionized water to remove surface organic matter and particulate contaminants. Then, the substrate was treated with ultraviolet-ozone or plasma to improve its surface hydrophilicity and the adhesion of subsequent thin films. A tin oxide (SnO2) colloidal solution was then spin-coated onto the treated ITO substrate at 2000 rpm to form a film, which was then annealed and cured at 180°C to form a dense electron transport layer.

[0038] 2. A precursor solution was prepared by dissolving PbI2 in a mixed solvent of dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) at a volume ratio of 9:1. The precursor solution was spin-coated onto a SnO2-modified ITO substrate at 1500 rpm and then annealed at 65 °C for 1 min to obtain a PbI2 film.

[0039] 3. Dissolve formamidin hydroiodide (FAI), methylamine hydrochloride (MACl), and methylamine bromide (MABr) in 1 mL of isopropanol in a mass ratio of 90:9:9 to prepare an organic salt solution. Spin-coat the solution onto a PbI2 film at 2000 rpm and anneal at 100-150°C for 10-30 min to form a uniform and dense perovskite light-absorbing layer.

[0040] 4. A chlorobenzene solution with pyrene-aniline-derived oligomers A, B, or C having a bridging structure as the hole transport material is spin-coated onto the surface of a perovskite layer and then dried and cured at low temperature to form a hole transport layer.

[0041] 5. A silver electrode with a thickness of approximately 80–150 nm was deposited on the hole transport layer by magnetron sputtering, and an encapsulating film and a glass cover were placed on top of the silver electrode. The perovskite solar cell was then hot-pressed and encapsulated for 5 min at 50–300 °C and 0.1–80 kPa to obtain the perovskite solar cell.

[0042] Figure 13 For example 1, the current density-voltage ratio of a perovskite solar cell fabricated using pyrene-aniline-derived oligomer A with a 1,9-nonyl-bridged structure as the hole transport layer is calculated. J - V ) curve; from Figure 13 It can be seen that the short-circuit current density of the perovskite solar cell fabricated with A as the hole transport layer is 25.23 mA / cm². 2 The open-circuit voltage is 1.18 V, the fill factor is 81.80%, and the photoelectric conversion efficiency is 24.27%.

[0043] Application Example 2 Figure 14 For example 2, a SEM image of a perovskite solar cell structure fabricated using pyrene-aniline-derived oligomer B with a bridging structure as the hole transport layer is shown. Figure 14 It is known that perovskite solar cells are prepared using ITO as the anode conductive glass, tin dioxide (SnO2) as the electron transport layer, FAPbI3 perovskite (PSK) as the solar light absorption layer, Ag as the conductive cathode, and pyrene aniline-derived oligomer B with a bridging structure as the hole transport layer (HTL).

[0044] Figure 15For example 2, the current density-voltage ratio of a perovskite solar cell fabricated using pyrene-aniline-derived oligomer B with a 1,10-decyl bridging structure as the hole transport layer is calculated. J - V ) curve; from Figure 15 It can be seen that the short-circuit current density of the perovskite solar cell fabricated using pyrene-aniline-derived oligomer B as the hole transport layer is 25.62 mA / cm². 2 The open-circuit voltage is 1.18 V, the fill factor is 84.39%, and the photoelectric conversion efficiency is 25.47%.

[0045] Application Example 3 Figure 16 For example 3, a perovskite solar cell was fabricated using pyrene-aniline-derived oligomer C with a 1,13-tetraalkyl-bridged structure as the hole transport layer. J - V Curve. From Figure 16 It can be seen that the short-circuit current density of the perovskite solar cell fabricated with C as the hole transport layer is 25.38 mA / cm². 2 The open-circuit voltage is 1.18 V, the fill factor is 82.69%, and the photoelectric conversion efficiency is 224.68%.

[0046] Figure 17 The steady-state output efficiency of perovskite solar cells fabricated using pyrene-aniline-derived oligomers A, B, or C with bridging structures as the hole transport layer in Examples 1-3 is shown. Figure 17 It is known that the perovskite solar cells prepared using pyrene-aniline-derived oligomers A, B, or C with bridging structures as hole transport layers have stable power output photoelectric conversion efficiencies of 23.02%, 24.81%, and 23.78%, respectively, and can be maintained for more than 300 seconds.

[0047] Figure 18 The short-circuit current for stable power output of perovskite solar cells fabricated using pyrene-aniline-derived oligomers A, B, or C with bridging structures as the hole transport layer in Examples 1-3 is used. Figure 18 It can be seen that the stable power output short-circuit current of perovskite solar cells fabricated with A, B, or C as hole transport layers is 22.78 mA / cm². 2 223.4 mA / cm 2 and 222.95 mA / cm 2 And it can last for more than 300 seconds.

[0048] The perovskite solar cells prepared by this invention using pyrene-aniline-derived oligomers A, B, or C with bridging structures as hole transport layers have photoelectric conversion performance and other parameters that are superior to those of perovskite solar cells prepared by commercial Spiro-OMeTAD, and are also lower in cost, showing good market application prospects.

[0049] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations and simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A class of pyrene-aniline-derived oligomers with a bridging structure, characterized in that, The molecular structure of the pyrene-aniline-derived oligomer is shown below: ； Wherein, R1 is a saturated or unsaturated alkyl chain, benzene ring, saturated or unsaturated heterocyclic ring, sulfur, nitrogen, oxygen, or phosphorus atom with 1 to 100 carbon atoms, R2 is a hydrogen atom or an aniline derivative group, n=2~200, m=2~50.

2. The pyrene-aniline-derived oligomer with a bridging structure according to claim 1, characterized in that, The structure of the aniline derivative group is as follows: ； R1 is: 。 3. The pyrene-aniline-derived oligomer with a bridging structure according to claim 1, characterized in that, The molecular structural formula of the pyrene-aniline-derived oligomer with the bridging structure is: 、 、 、 、 、 、 。 4. The method for preparing the pyrene-aniline-derived oligomer with a bridging structure according to any one of claims 1-3, characterized in that, The pyrene aniline-derived oligomer is prepared by adding a pyrene aniline derivative, a bridging monomer, and a base to a solvent, refluxing and stirring at 70-150°C under a protective atmosphere until the reaction is complete, and then extracting and purifying the mixture.

5. The method for preparing the pyrene-aniline-derived oligomer with a bridging structure according to claim 4, characterized in that, The bridging monomer is a saturated or unsaturated alkyl chain, benzene ring, saturated or unsaturated heterocyclic ring, sulfur, nitrogen, oxygen, or phosphorus atom with 1 to 100 carbon atoms; the base is one or more of potassium carbonate, cesium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, potassium tert-butoxide, and sodium tert-butoxide; the solvent is one or more of toluene, ethanol, water, tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, and dimethyl sulfoxide; the protective atmosphere is argon or nitrogen; the equimolar ratio of the pyrene aniline derivative, the bridging monomer, and the base is (1 to 4): 1: (2 to 8).

6. The method for preparing the pyrene-aniline-derived oligomer with a bridging structure according to claim 4, characterized in that, The structure of the pyrene aniline derivative is as follows: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 7. The use of the pyrene aniline-derived oligomers with bridging structures according to any one of claims 1-3 in organic electronic devices.

8. The application of the pyrene-aniline-derived oligomer with a bridging structure according to claim 7 in organic electronic devices, characterized in that, The organic electronic device is a perovskite solar cell, an organic light-emitting diode, or an organic field-effect transistor.

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