A fused ring receptor material based on benzimide and its preparation method and application

Abstract

The present invention discloses a condensed ring receptor material based on benzimide and its preparation method and application. The chemical formula of the condensed ring receptor material based on benzimide in the present invention is shown in Formula I, wherein each occurrence of R1 and R2 is independently selected from substituted or unsubstituted C 1～30 Alkyl, substituted or unsubstituted C 1～30 Alkoxy, substituted or unsubstituted C 2～30 Alkynyl, substituted or unsubstituted C 6～30 Ar1 and Ar2 are independently selected from substituted or unsubstituted C 6～30 Aryl, substituted or unsubstituted C 6～30 Heteroaryl, substituted or unsubstituted C 8～30 A fused aromatic cyclic group, a substituted or unsubstituted C 6～30 A fused heteroaryl cyclic group, a substituted or unsubstituted C 4～30 The condensed ring acceptor material based on benzimide in the present invention has good application prospects in solar cells. #imgabs0#

Description

Technical Field

[0001] The present invention belongs to the technical field of photovoltaic materials, and in particular relates to a condensed ring receptor material based on benzimide, and a preparation method and application thereof. Background Art

[0002] Organic solar cells (OSCs) have become a major research hotspot in the field of solar energy due to their unique advantages such as material synthesis diversity, solution processing, light weight, low cost, and easy preparation of flexible and large-area devices. A complete OSC device mainly includes an active layer that absorbs photons and converts them into free carriers, a transport layer distributed at both ends for extracting and transporting carriers, and electrodes for collecting carriers and guiding them to the circuit. The active layer is closely related to the separation of excitons, charge transport and collection processes. Usually, the active layer includes an acceptor material, which can affect the performance of OSCs applied in the active layer, such as the photoelectric conversion efficiency (PCE). However, at present, the types of acceptor materials are relatively single, which to some extent limits the application and development of solar cells. Summary of the Invention

[0003] The present invention aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the present invention proposes a new type of condensed ring acceptor material based on benzimide, which has good application prospects in solar cells.

[0004] The present invention also provides a method for preparing a condensed ring receptor material based on benzimide.

[0005] The present invention also provides an active layer.

[0006] The present invention also provides a photovoltaic device.

[0007] The present invention also provides a method for preparing a photovoltaic device.

[0008] The present invention also proposes the application of the above-mentioned condensed ring receptor material based on benzimide.

[0009] In the first aspect of the present invention, a fused ring receptor material based on benzimide is proposed, the chemical formula of which is shown in Formula I:

[0010]

[0011] wherein R1 and R2 are each independently selected from substituted or unsubstituted C 1～30 Alkyl, substituted or unsubstituted C 1～30 Alkoxy, substituted or unsubstituted C 2～30 Alkynyl, substituted or unsubstituted C 6～30 aryl groups;

[0012] Ar1 and Ar2 are independently selected from substituted or unsubstituted C 6～30 Aryl, substituted or unsubstituted C 6～30 Heteroaryl, substituted or unsubstituted C 8～30 A fused aromatic cyclic group, a substituted or unsubstituted C 6～30 A fused heteroaryl cyclic group, a substituted or unsubstituted C 4～30 of a heterocyclic group.

[0013] The fused ring receptor material based on benzimide according to the embodiment of the present invention has at least the following beneficial effects:

[0014] The benzoimide-based fused ring acceptor material disclosed in this invention is a novel acceptor material with promising application prospects in solar cells. This acceptor material utilizes a benzoimide core modified with fused ring benzothiophene, resulting in a flat molecular structure. The end groups connect to the electron-deficient Ar1 and Ar2 groups to form an ADA-type molecule, effectively promoting intramolecular charge transfer and regulating the frontier orbital energy levels. This acceptor material can be used to prepare an active layer for optical photovoltaic (OPV) applications, resulting in high photoelectric conversion efficiency.

[0015] The application of the present invention's fused ring benzimide-based acceptor material as a third component in ternary organic photovoltaic cell devices (e.g., ternary OPVs) significantly improves the device's charge separation and transfer efficiency, significantly enhances light absorption, optimizes the device's active layer film morphology, and reduces the device's non-radiative recombination losses. This avoids the drawbacks of existing high-efficiency devices, such as large non-radiative recombination energy losses, resulting in organic photovoltaic cells with efficiencies exceeding 17%, which is of great significance for the preparation of low-cost, large-area, high-efficiency cell devices. The present invention's fused ring benzimide-based acceptor material modified with fused ring benzothiophene as a third component in ternary solar cell devices achieves device efficiencies significantly higher than those of binary material systems, with improvements in open-circuit voltage (Voc), fill factor (FF), and short-circuit current (Jsc).

[0016] In addition, the condensed ring acceptor material of benzimide in the present invention is soluble in common solvents such as chloroform and chlorobenzene, is easy to process, and has good industrial application prospects.

[0017] In some embodiments of the present invention, the halogen comprises at least one of fluorine, chlorine, bromine or iodine.

[0018] In some embodiments of the present invention, each occurrence of R1 is independently selected from substituted or unsubstituted C 1～10 Alkyl, substituted or unsubstituted C 1～10 Alkoxy, substituted or unsubstituted C 2～10 Alkynyl, substituted or unsubstituted C 6～15of aromatic groups.

[0019] In some embodiments of the present invention, each occurrence of R1 is independently selected from C 5～10 Alkyl, C 5～10 of alkoxy.

[0020] In some embodiments of the present invention, R2 is selected from substituted or unsubstituted C 1～10 Alkyl, substituted or unsubstituted C 1～10 Alkoxy, substituted or unsubstituted C 2～10 Alkynyl, substituted or unsubstituted C 6～15 of aromatic groups.

[0021] In some embodiments of the present invention, R2 is selected from substituted or unsubstituted C 5～10 Alkyl, substituted or unsubstituted C 5～10 of alkoxy.

[0022] In some embodiments of the present invention, Ar1 and Ar2 are independently selected from one of the following groups:

[0023]

[0024] wherein X1 and X2 are independently selected from H, halogen, cyano, halogen substituted or unsubstituted C 1～30 Alkyl, halogen substituted or unsubstituted C 1～30 R3 is selected from halogen substituted or unsubstituted C 1～30 of alkyl.

[0025] Through the above-described embodiment, the benzoimide-based fused ring acceptor material of the present invention uses a benzoimide core modified with fused ring benzothiophene, resulting in a flat molecular structure. The end groups are connected to electron-deficient Ar1 and Ar2 (such as indanone derivatives) to form ADA-type molecules, effectively promoting intramolecular charge transfer and regulating the molecular frontier orbital energy levels. The active layer containing this acceptor material can be used to prepare an OPV, which greatly improves the device's charge separation and transfer efficiency, and significantly enhances its light absorption capacity.

[0026] In some embodiments of the present invention, X1 and X2 are independently selected from fluorine, chlorine, bromine, iodine, cyano, halogen substituted or unsubstituted C 1～5 Alkyl, halogen substituted or unsubstituted C 1～5 of alkoxy.

[0027] In some embodiments of the present invention, R3 is selected from substituted or unsubstituted C 1～3 of alkyl.

[0028] In some embodiments of the present invention, the benzimide-based fused ring acceptor material is selected from at least one of the following chemical formulas:

[0029]

[0030]

[0031] wherein X1 and X2 are each independently selected from hydrogen, halogen, cyano or C 1～5 of alkyl.

[0032] In some embodiments of the present invention, the benzimide-based fused ring acceptor material is selected from at least one of the following chemical formulas:

[0033]

[0034]

[0035] wherein X1 and X2, at each occurrence, are independently selected from hydrogen, fluorine, chlorine, bromine or iodine.

[0036] In some embodiments of the present invention, the benzimide-based fused ring acceptor material is selected from at least one of the following chemical formulas:

[0037]

[0038]

[0039] In a second aspect of the present invention, a method for preparing a fused ring receptor material based on benzimide is proposed, comprising the following steps: taking a compound of formula II and H-Ar1-H containing an Ar1 group and H-Ar2-H containing an Ar2 group, and subjecting the compound to a Knoevenagel reaction to obtain the fused ring receptor material based on benzimide, wherein the structural formula of compound II is as follows:

[0040]

[0041] In some embodiments of the present invention, the H-Ar1-H and H-Ar2-H are independently selected from at least one of the following structural formulas:

[0042]

[0043] wherein X1 and X2 are independently selected from H, halogen, cyano, halogen substituted or unsubstituted C 1～30 Alkyl, halogen substituted or unsubstituted C 1～30 R3 is selected from halogen substituted or unsubstituted C 1～30 of alkyl.

[0044] In some embodiments of the present invention, the H-Ar1-H comprises an indone derivative, and / or the H-Ar2-H comprises an indone derivative.

[0045] In some embodiments of the present invention, H-Ar1-H and H-Ar2-H are independently selected from 5,6-dihalo-3-(dicyanomethylidene)indone.

[0046] In some embodiments of the present invention, the 5,6-dihalo-3-(dicyanomethylene)indone comprises at least one of 5,6-difluoro-3-(dicyanomethylene)indone or 5,6-dichloro-3-(dicyanomethylene)indone.

[0047] In some embodiments of the present invention, the molar ratio of the compound of formula II to H-Ar1-H and H-Ar2-H is (0.15-0.5):0.5:0.5, and can be optionally (0.3-0.35):0.5:0.5.

[0048] In some embodiments of the present invention, the Knoevenagel reaction is carried out in a solvent I. Preferably, the solvent I is an organic solvent.

[0049] In some embodiments of the present invention, the solvent I comprises at least one of chloroform, toluene, tetrahydrofuran, N,N-dimethylformamide, dichloromethane, 1,4-dioxane or dimethyl sulfoxide.

[0050] In some embodiments of the present invention, the ratio of the compound of formula II to solvent I is (5-8.5) mmol:1L, optionally (6-7) mmol:1L, for example, specifically about 6.4 mmol:1L.

[0051] In some embodiments of the present invention, the compound of formula II is reacted with H-Ar1-H and H-Ar2-H in the presence of catalyst I.

[0052] In some embodiments of the present invention, the catalyst I comprises pyridine. The role of the catalyst I includes providing weakly alkaline reaction conditions.

[0053] In some embodiments of the present invention, the ratio of the compound of formula II to catalyst I is (0.08-0.2) mmol:1 mL, optionally (0.11-0.14) mmol:1 mL, for example, specifically about 0.128 mmol:1 mL.

[0054] In some embodiments of the present invention, the reaction of the compound of formula II with H-Ar1-H and H-Ar2-H is carried out in a protective atmosphere.

[0055] In some embodiments of the present invention, the preparation method comprises the following steps: mixing the compound of formula II with H-Ar1-H, H-Ar2-H, and solvent I, adding catalyst I, and reflux reaction under a protective atmosphere to obtain the benzimide-based fused ring receptor material.

[0056] In some embodiments of the present invention, the reflux time is 7-20 hours; optionally 10-14 hours; for example, specifically about 12 hours.

[0057] In some embodiments of the present invention, after the reflux reaction, a reaction mixture I is obtained, which is purified to obtain the receptor material.

[0058] In some embodiments of the present invention, the purification comprises mixing the reaction mixture I with the purification solvent I, filtering to obtain a crude product of the receptor material, and separating by column chromatography to obtain the receptor material.

[0059] In some embodiments of the present invention, the purification solvent I comprises at least one of methanol, acetone or diethyl ether.

[0060] In some embodiments of the present invention, the preparation method further comprises preparing a compound of formula II, specifically comprising the following operations: subjecting a compound of formula III to a formylation reaction to obtain a compound of formula II, wherein the structural formula of compound III is as follows:

[0061]

[0062] In some embodiments of the present invention, the formylation reaction is a Vilsmeier-Haack reaction. Preferably, the Vilsmeier-Haack reaction is carried out under a protective atmosphere.

[0063] In some embodiments of the present invention, the preparation of the compound of formula II specifically includes the following operations: taking the compound of formula III, N,N-dimethylformamide and phosphorus oxychloride, and performing a formylation reaction to obtain the compound of formula II.

[0064] In some embodiments of the present invention, the ratio of the compound of formula III to N,N-dimethylformamide is (0.005-0.05) mmol:1 mL, optionally (0.01-0.03) mmol:1 mL, for example, specifically about 0.023 mmol:1 mL.

[0065] In some embodiments of the present invention, the ratio of the compound of formula III to phosphorus oxychloride is (0.2-0.5) mmol:1 mL, optionally (0.25-0.4) mmol:1 mL, for example, specifically about 0.38 mmol:1 mL.

[0066] In some embodiments of the present invention, the preparation of the compound of formula II specifically includes the following operations: adding phosphorus oxychloride to a mixture containing the compound of formula III and N,N-dimethylformamide, mixing, and sequentially performing a first stage stirring and a second stage stirring to obtain the compound of formula II.

[0067] In some embodiments of the present invention, the mixture contains solvent II.

[0068] In some embodiments of the present invention, the solvent II includes 1,2-dichloroethane, chloroform, or N,N-dimethylformamide.

[0069] In some embodiments of the present invention, the temperature during the mixing process and the first stage of stirring is (-10)°C to 5°C; optionally (-5)°C to 1°C; for example, specifically about 0°C.

[0070] In some embodiments of the present invention, the duration of the first stage stirring is 0.2-3 h; optionally 0.5-1.5 h; for example, specifically about 1 h.

[0071] In some embodiments of the present invention, the stirring temperature in the second stage is 70-110°C; optionally 80-100°C; for example, specifically about 90°C.

[0072] In some embodiments of the present invention, the duration of the second stage stirring is 5-20 hours; optionally 8-14 hours.

[0073] According to the above embodiment, by regulating the order of adding N,N-dimethylformamide and phosphorus oxychloride, and stirring at different temperatures in the two stages, the reaction of N,N-dimethylformamide and phosphorus oxychloride can be completed in sequence to generate a strongly electrophilic Vilsmeier intermediate, which is then subjected to an electrophilic substitution reaction with the compound of formula III.

[0074] In some embodiments of the present invention, a formylation reaction is performed to obtain a reaction mixture II, which is then purified to obtain a compound of formula II.

[0075] In some embodiments of the present invention, the purification comprises extracting and performing column chromatography on the reaction mixture II.

[0076] In some embodiments of the present invention, the extraction comprises dichloromethane.

[0077] In some embodiments of the present invention, the extraction and column chromatography steps further include removing the extractant in the extraction phase; optionally, the removal method includes rotary evaporation.

[0078] In some embodiments of the present invention, the preparation method further comprises preparing a compound of formula III, specifically comprising the following operations: subjecting the compound of formula IV to an oxidative ring-closure reaction to obtain a compound of formula III;

[0079] Among them, the structural formula of compound IV is shown below:

[0080]

[0081] In some embodiments of the present invention, a compound of formula IV, a solvent III and nitromethane are added with FeCl 3 and refluxed under a protective atmosphere to obtain a compound of formula III.

[0082] In some embodiments of the present invention, the compound of formula IV, solvent III and nitromethane are mixed, and then FeCl3 is added.

[0083] In some embodiments of the present invention, the reflux reaction time is 8-20 hours, optionally 10-14 hours, for example, specifically 12 hours.

[0084] In some embodiments of the present invention, the molar ratio of the compound of formula IV to FeCl3 is 1:(3-12), optionally 1:(6-9), for example, specifically about 1:7.65.

[0085] In some embodiments of the present invention, the solvent III comprises at least one of toluene, tetrahydrofuran, N,N-dimethylformamide, dichloromethane, 1,4-dioxane or dimethyl sulfoxide.

[0086] In some embodiments of the present invention, after reflux reaction, a reaction mixture III is obtained, which is purified to obtain a compound of formula III.

[0087] In some embodiments of the present invention, the purification comprises drying, extracting, and column chromatography of the reaction mixture III.

[0088] In some embodiments of the present invention, the extraction agent used in the extraction includes dichloromethane.

[0089] In some embodiments of the present invention, the extraction and column chromatography steps further include removing the extractant in the extraction phase; optionally, the removal method includes rotary evaporation.

[0090] In some embodiments of the present invention, the preparation method further comprises preparing the compound of formula IV, specifically comprising the following operations:

[0091] S1, the compound of formula VI is subjected to a substitution reaction to obtain a compound of formula V;

[0092] S2, a compound of formula V and a thiophene boronic acid or thiophene boronic ester containing an R1 group are subjected to a Suzuki coupling reaction to obtain a compound of formula IV;

[0093] Wherein, the structural formulas of the compound of formula V, the compound of formula VI, and the thiophene boronic acid containing the R1 group are as follows:

[0094]

[0095] Wherein, X3 is selected from fluorine, chlorine, bromine or iodine, preferably bromine.

[0096] In some embodiments of the present invention, the substitution reaction is a bromination reaction.

[0097] In some embodiments of the present invention, the step of preparing the compound of formula IV comprises the following operations:

[0098] S1, taking the compound of formula VI and solvent IV, adding Br2, and reacting to obtain the compound of formula V;

[0099] S2, taking the compound of formula V, thiophene boronic acid containing an R1 group, solvent V, and catalyst II, and reacting them to obtain the compound of formula IV.

[0100] In some embodiments of the present invention, the solvent IV comprises at least one of acetic acid, toluene, water, tetrahydrofuran, N,N-dimethylformamide, dichloromethane, 1,4-dioxane or dimethyl sulfoxide.

[0101] In some embodiments of the present invention, the reactions in steps S1 and S2 are both performed in a protective atmosphere.

[0102] In some embodiments of the present invention, in step S1, after the reaction, a reaction mixture IV is obtained, which is purified to obtain a compound of formula V. Optionally, the purification includes drying, extracting, and column chromatography of the reaction mixture III.

[0103] In some embodiments of the present invention, in step S1, Br2 is added by dropwise addition of liquid bromine.

[0104] In some embodiments of the present invention, in step S2, the catalyst II includes at least one of tetrakis(triphenylphosphine)palladium, palladium acetate, bis(triphenylphosphine)palladium dichloride, tris(dibenzylideneacetone)dipalladium, tri(o-tolyl)phosphine or cuprous iodide.

[0105] In some embodiments of the present invention, the reaction in step S2 is carried out under the action of potassium carbonate.

[0106] In some embodiments of the present invention, in step S2, the molar ratio of the compound of formula V to the thiophene boronic acid containing an R1 group is (1.5-4):(1-5).

[0107] In some embodiments of the present invention, in step S2, the solvent V comprises at least one of toluene, water, tetrahydrofuran, N,N-dimethylformamide, dichloromethane, 1,4-dioxane or dimethyl sulfoxide.

[0108] In some embodiments of the present invention, the reaction temperature in step S2 is 80-130° C., and the reaction time is 12-36 h.

[0109] In some embodiments of the present invention, in step S2, after the reaction, a reaction mixture V is obtained, which is purified to obtain a compound of formula VI. Optionally, the purification includes drying, extracting, and column chromatography of the reaction mixture V.

[0110] In some embodiments of the present invention, the preparation method further comprises the step of preparing compound VI, which specifically comprises the following operations:

[0111] S0-1, reacting the compound of formula VIII with N-bromosuccinimide to obtain the compound of formula VII;

[0112] S0-2, a compound of formula VII and thiophene boronic acid, undergoing Suzuki coupling reaction to obtain a compound of formula VI;

[0113] Wherein, the structural formulas of the compound of formula VIII and the compound of formula VII are as follows:

[0114]

[0115] In some embodiments of the present invention, the steps for preparing the compound VI specifically include the following operations:

[0116] S0-1, mixing the compound of formula VIII, N-bromosuccinimide and solvent VI, and reacting to obtain the compound of formula VII;

[0117] S0-2, take the compound of formula VII, thiophene boronic acid, and catalyst III, and react to obtain the compound of formula VI.

[0118] In some embodiments of the present invention, in step S0-1, the molar ratio of the compound of formula VIII N-bromosuccinimide is 1:(1-3).

[0119] In some embodiments of the present invention, in step S0-1, the solvent VI includes at least one of toluene, tetrahydrofuran, N,N-dimethylformamide, dichloromethane, 1,4-dioxane or dimethyl sulfoxide.

[0120] In some embodiments of the present invention, in step S0-1, the reaction time is 12-36 hours.

[0121] In some embodiments of the present invention, in step S0-1, after the reaction, a reaction mixture VI is obtained, which is purified to obtain a compound of formula VII. Optionally, the purification includes drying, extracting, and column chromatography of the reaction mixture VI.

[0122] In some embodiments of the present invention, step S0-2 comprises the following steps: taking a compound of formula VII, thiophene boronic acid and solvent VII, adding catalyst III to obtain a compound of formula VI.

[0123] In some embodiments of the present invention, the catalyst III includes but is not limited to tetrakis(triphenylphosphine)palladium, palladium acetate, bis(triphenylphosphine)palladium dichloride, and tris(dibenzylideneacetone)dipalladium.

[0124] In some embodiments of the present invention, in step S0-2, the molar ratio of the compound of formula VII to thiophene boronic acid is 1:(1-4).

[0125] In some embodiments of the present invention, in step S0-2, the reaction time is 12-36 hours, and the reaction temperature is 80-130°C.

[0126] In some embodiments of the present invention, in step S0-2, the solvent VII includes at least one of toluene, water, tetrahydrofuran, N,N-dimethylformamide, dichloromethane, 1,4-dioxane or dimethyl sulfoxide.

[0127] In some embodiments of the present invention, in step S0-2, after the reaction, a reaction mixture VII is obtained, which is purified to obtain a compound of formula VI. Optionally, the purification includes drying, extracting, and column chromatography of the reaction mixture VII.

[0128] In some embodiments of the present invention, the reactions in steps S0-1 and S0-2 are both performed in a protective atmosphere.

[0129] In some embodiments of the present invention, the preparation method comprises the following steps:

[0130] S0-1, reacting the compound of formula VIII with N-bromosuccinimide to obtain the compound of formula VII;

[0131] S0-2, a compound of formula VII and thiophene boronic acid, undergoing Suzuki coupling reaction to obtain a compound of formula VI;

[0132] S1, the compound of formula VI is subjected to a substitution reaction to obtain a compound of formula V;

[0133] S2, a compound of formula V and a thiophene boronic acid or thiophene boronic ester containing an R1 group are subjected to a Suzuki coupling reaction to obtain a compound of formula IV;

[0134] S3, the compound of formula IV is subjected to an oxidative ring-closure reaction to obtain a compound of formula III;

[0135] S4, a compound of formula III, is subjected to a formylation reaction to obtain a compound of formula II;

[0136] S5, taking the compound of formula II and H-Ar1-H containing group Ar1 and H-Ar2-H containing group Ar2, and subjecting them to Knoevenagel reaction to obtain the condensed ring receptor material based on benzimide.

[0137] The reaction process is as follows:

[0138]

[0139] In a third aspect of the present invention, an active layer is provided, comprising an acceptor material I and a donor material, wherein the acceptor material I is the above-mentioned condensed ring acceptor material based on benzimide.

[0140] In some embodiments of the present invention, the acceptor material further includes an acceptor material II, and the acceptor material II includes at least one of small molecule acceptor materials such as Y6, L8-BO, BTP-4Cl or BTP-eC9.

[0141] In some embodiments of the present invention, the acceptor material II includes at least one of Y6, L8-BO, BTP-4Cl or BTP-eC9.

[0142]

[0143] In some embodiments of the present invention, the donor material includes at least one polymer donor material such as PM6, PBDB-T, D18 or PTQ-10.

[0144] In some embodiments of the present invention, the donor material comprises at least one of PM6, PBDB-T, D18, or PTQ-10.

[0145]

[0146] In some embodiments of the present invention, in the active layer, the mass ratio of the donor material to the benzoimide-based fused ring acceptor material is 1:(0.02-0.5), and can be optionally 1:(0.1-0.3).

[0147] In some embodiments of the present invention, in the active layer, the mass ratio of the donor material to the acceptor material II is 1:(0.8-2), and can be optionally 1:(1.2-1.6).

[0148] In some embodiments of the present invention, in the active layer, the mass ratio of the donor material, the acceptor material II and the acceptor material I is 1:(0.8-2):(0.02-0.5), optionally 1:(1.2-1.6):(0.1-0.3), and more preferably 1:1.2:0.1.

[0149] In ternary photovoltaic cells, when the mass ratio of donor material (such as PM6), acceptor material II (L8-BO) and benzoimide-based fused ring acceptor material (such as PhITT-4F, PhITT-4Cl) is 1:1.2:0.1, the resulting cell has higher photoelectric conversion efficiency and better battery performance compared with other mass ratios.

[0150] In a fourth aspect of the present invention, a photovoltaic device is provided, comprising the above-mentioned benzimide-based fused ring acceptor material or the above-mentioned active layer.

[0151] In some embodiments of the present invention, the photovoltaic device is a photovoltaic cell.

[0152] In the above embodiment, the photovoltaic device comprises an active layer comprising a ternary system of the above-described benzimide-based fused ring acceptor material, a donor material, and acceptor material II. When the photovoltaic device is an organic photovoltaic cell, the synergistic interaction between the acceptor and donor in the active layer can significantly increase the open-circuit voltage of the resulting organic photovoltaic cell, ultimately improving its photoelectric conversion efficiency.

[0153] In some embodiments of the present invention, the photovoltaic cell is an organic photovoltaic cell.

[0154] In some embodiments of the present invention, the photovoltaic cell includes a substrate, a hole transport layer, an active layer, an electron transport layer, and a metal electrode that are stacked.

[0155] In some embodiments of the present invention, the substrate is at least one of indium tin oxide (ITO) glass or fluorine tin oxide (FTO).

[0156] In some embodiments of the present invention, the hole transport layer includes at least one of PEDOT:PSS, MoO3, V2O5, WO3 or NiO.

[0157] In some embodiments of the present invention, the electron transport layer includes at least one of PFN-Br, PNDIT-F3N, PDINN, or PDINO.

[0158] In some embodiments of the present invention, the metal electrode comprises at least one of Ag, Al or Cu.

[0159] In some embodiments of the present invention, the thickness of the active layer is 50-200 nm, and optionally 80-120 nm.

[0160] In some embodiments of the present invention, the thickness of the substrate is 0.01-1 mm, such as 0.2 mm.

[0161] In some embodiments of the present invention, the thickness of the hole transport layer is 10-200 nm.

[0162] In some embodiments of the present invention, the thickness of the electron transport layer is 2-50 nm.

[0163] In some embodiments of the present invention, the thickness of the electrode layer is 50-300 nm.

[0164] In a fifth aspect of the present invention, the use of the above-mentioned benzimide-based fused ring acceptor material in the preparation of organic photovoltaic cells, organic light-emitting diodes or perovskite solar cells is proposed.

[0165] Description and Definition

[0166] In the present invention, unless otherwise specified, scientific and technical terms used herein have the meanings commonly understood by those skilled in the art. However, for a better understanding of the present invention, definitions of some terms are provided below. When the definitions of terms provided herein are inconsistent with the meanings commonly understood by those skilled in the art, the definitions and interpretations of the terms provided herein shall prevail.

[0167] The protective gas in the "protective atmosphere" herein includes at least one of an inert gas or nitrogen.

[0168] As used herein, "substituted or unsubstituted" means that a group may or may not be further substituted by one or more groups selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, haloalkenyl, haloalkynyl, haloaryl, hydroxy, alkoxy, alkenyloxy, aryloxy, benzyloxy, haloalkoxy, haloalkenyloxy, haloaryloxy, nitro, nitroalkyl, nitroalkenyl, nitroalkynyl, nitroaryl, nitroheterocyclyl, amino, alkylamino, dialkylamino, alkenylamino, alkynylamino, arylamino, diarylamino, phenylamino, diphenylamino, benzylamino, dibenzylamino, hydrazino, acyl, acylamino, diacylamino, acyloxy, heterocyclyl, heterocyclyloxy, heterocyclylamino, haloheterocyclyl, carboxyl ester, carboxyl, carboxylamide, thiol, alkylthio, benzylthio, acylthio, and phosphorus-containing groups.

[0169] "Alkyl" means a group derived from a branched or straight chain saturated aliphatic alkane having the specified number of carbon atoms by removing one hydrogen. 1～30"Alkyl" means an alkyl group having a total carbon number of 1 to 30, including C 1～30 Straight chain alkyl, C 1～30 Branched alkyl and C 3～30 Cycloalkyl; for "C 1～10 The explanation of "substituted C 1～30 "alkyl" means C 1～30 At least one H in the optional alkyl group is substituted by a group as defined herein, and for "substituted C 1～10 The explanation of "alkyl" is similar to this, except that the number of carbon atoms is different.

[0170] "Alkoxy" refers to an alkyl group as defined herein attached to another group through an oxygen atom, i.e., "alkyl-O-". 1～30 "Alkoxy" means an alkoxy group having a total carbon number of 1 to 30, including C 1～30 Straight chain alkoxy, C 1～30 Branched alkoxy and C 2～30 The cycloalkoxy group of "C" may be, for example, methoxy, ethoxy, n-propoxy, isopropoxy, etc. 1～10 The explanation of "substituted C 1～30 "Alkoxy" means C 1～30 At least one H in the optional alkoxy group is substituted by a group defined herein, and the term "substituted C 1～10 The explanation is similar to this, except that the number of carbon atoms is different.

[0171] The "halogen" includes any one or two or more of fluorine, chlorine, bromine and iodine.

[0172] “C 2～30 "Alkenyl" means a straight or branched hydrocarbon group with one or more double bonds, and the total number of carbon atoms in the alkenyl group is 2 to 30, and the double bonds in the group can be in any position. 2～10 The explanation of "substituted alkenyl" is similar to this, except that the number of carbon atoms is different. 2～30 "Alkenyl" means C 2～30 At least one H in the optional alkenyl group is substituted by a group as defined herein. 2～10 The explanation of "alkenyl" is similar to this, except that the number of carbon atoms is different.

[0173] “C 2～30 "Alkynyl" means a straight or branched hydrocarbon group with one or more triple bonds, and the total number of carbon atoms in the alkynyl group is 2 to 30. The triple bond in the group can be in any position. 2～10The explanation of "substituted C 2～30 "Alkynyl" means C 2～30 The optional alkynyl group wherein at least one H is substituted by a group as defined herein is a "substituted C 2～10 The explanation of "alkynyl" is similar to this, except that the number of carbon atoms is different.

[0174] “C 6～30 "Aryl" means an all-carbon monocyclic or fused polycyclic group with a completely conjugated π electron system. "Aryl" means an all-carbon monocyclic or fused polycyclic group of 6 to 30 carbon atoms; for example, benzene, naphthalene, indene, fluorene, etc. "C 6-15 The explanation of "substituted C 6～30 "Aryl" means C 6～30 At least one H in the optional aryl group is substituted by a corresponding group as defined herein. 6-15 The "aryl group" has a similar explanation, except that the number of carbon atoms is different.

[0175] “C 8～30 The term "cyclic group of fused aromatic group" refers to a group formed by sharing a ring edge between an aromatic group and a cyclic group, and the number of carbon atoms in the fused aromatic group is 8 to 30. "Substituted C 8～30 "Cyclic group of fused aromatic group" means C 8～30 At least one H in the cyclic group of the optionally fused aryl group is substituted with a group as defined herein.

[0176] “C 6～30 The term "substituted C fused heteroaryl cyclic group" refers to a group formed by a heteroaryl group and a cyclic group sharing a ring edge, and the number of carbon atoms in the fused heteroaryl cyclic group is 6 to 30. 6～30 "Cyclic group of fused heteroaryl" means C 6～30 At least one H in the cyclic group of the optionally fused heteroaryl is substituted with a group as defined herein.

[0177] "Heterocyclic group" refers to a saturated cyclic group derived from a cycloalkyl group in which a ring carbon atom is replaced by one or more heteroatoms, including monocyclic or polycyclic heterocyclic groups; the polycyclic heterocyclic group refers to a polycyclic group formed by connecting a monocyclic heterocyclic group with other heterocyclic groups or cycloalkyl groups through spiro, bridge, fusion, etc.; the heteroatom is generally selected from N, O, S; the carbon atoms or heteroatoms in the heterocyclic group can be further oxidized, i.e., to form C(O), N(O), SO, SO2.

[0178] “C 4～30 "Substituted heterocyclic group" means that the number of carbon atoms in the heterocyclic group is 4 to 30.4～30 "Heterocyclic group" means C 4～30 The optional heterocyclic group has at least one H group substituted with a group as defined herein.

[0179] "Heteroaryl" refers to a monocyclic or polycyclic group containing one or more heteroatoms in the ring and having aromatic properties. The heteroatoms are generally selected from N, O, and S. Preferably, the heteroatoms are independently selected from 1-3 N and / or O atoms. In addition, the N and S atoms may be optionally oxidized and the N atoms may be optionally quaternized. The "heteroaryl" group includes "monocyclic heteroaryl" and "fused-ring heteroaryl". The fused-ring heteroaryl group refers to a group containing one or more heteroatoms and having aromatic properties, formed by two or more cyclic structures sharing two adjacent atoms.

[0180] “C 4～30 The number of carbon atoms in the heteroaryl group is 4 to 30. 4～30 "heteroaryl" means C 4～30 The optional heteroaryl group has at least one H group substituted with a group as defined herein.

[0181] Other features and advantages of the present invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0182] The present invention will be further described below with reference to the accompanying drawings and embodiments, in which:

[0183] Figure 1 The chemical formula of the fused ring receptor material based on benzimide of the present invention is shown in FIG.

[0184] Figure 2 Schematic diagram of the process for preparing a fused ring receptor material based on benzimide in an embodiment of the present invention;

[0185] Figure 3 Schematic diagram of the structure of the organic photovoltaic cell device in Example 3 of the present invention;

[0186] Figure 4 JV curves of the organic photovoltaic cell devices in Comparative Example 1 and Examples 3-4 of the present invention;

[0187] Figure 5 for Figure 4 A partial enlarged view of .

[0188] Figure 6 EQE curve of the organic photovoltaic cell device in Example 3-4 of the present invention. DETAILED DESCRIPTION

[0189] The following will clearly and completely describe the concept and technical effects of the present invention in conjunction with the embodiments to fully understand the purpose, features and effects of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, other embodiments obtained by those skilled in the art without creative work are all within the scope of protection of the present invention.

[0190] Unless otherwise specified, the temperature in the specific implementation manner is room temperature, that is, in the range of 20 to 30° C., and will not have a significant impact on the test results.

[0191] The experimental methods in the following examples, for which specific conditions are not specified, are generally performed in accordance with conventional conditions in the art or conditions recommended by the manufacturers; the raw materials and reagents used, unless otherwise specified, are all commercially available from conventional markets.

[0192] Compounds 1 and 2 were purchased from Suzhou Nakai Co., Ltd.

[0193] ITO glass: Youxuan Technology Company, 0.7mm 7-9 ohms, 0.2mm thick;

[0194] Donor materials PM6 and acceptor L8-BO were purchased from Shuolun Organic Optoelectronics Technology (Beijing) Co., Ltd.

[0195] PNDIT-F3N: purchased from Beijing Zhiyan Technology Co., Ltd.;

[0196]

[0197]

[0198] Example 1

[0199] This embodiment discloses a fused ring receptor material PhITT-4F based on benzimide, and the preparation reaction process thereof is as follows:

[0200]

[0201] The preparation process of PhITT-4F includes:

[0202] (I) The synthesis of compound 2 comprises: weighing compound 1 (purchased from Nanjing Zhiyan Co., Ltd.) (4 g, 10.8 mmol) and dissolving it in 40 mL of tetrahydrofuran in a 250 mL round-bottom flask, replacing the gas with argon for 15 minutes, and then adding NBS (3.83 g, 21.6 mmol). The reactants were reacted at room temperature for 24 hours. The tetrahydrofuran was dried and extracted with dichloromethane. The solvent was dried to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain a solid product, namely compound 2 (5.02 g, yield 88%); HRMS (m / z, MALDI): Calc. for C 20 H 19 Br2NO2S2,[M+H] + :529.31,found:528.92.

[0203] (II) Synthesis of Compound 3: In a 250 mL round-bottom flask, compound 3 (3 g, 5.7 mmol) and 2-thiopheneboronic acid (1.58 g, 12.5 mmol) were weighed and dissolved in 60 mL of toluene / water (volume ratio 5:1). The gas was replaced with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (0.85 g, 0.60 mmol) and K2CO3 (2.3 g, 36.3 mmol) were added to the reaction system under argon protection. The reactants were refluxed at 110°C for 24 hours. The reaction mixture was cooled to room temperature, the toluene was evaporated, and the mixture was extracted with dichloromethane. The solvent was evaporated to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain compound 3 (2.45 g, yield 81%). HRMS (m / z, MALDI): Calc. for: C 28 H 25 NO2S4,[M+H] + :535.75,found:535.98.

[0204] (III) The synthesis of compound 4 comprises: weighing compound 3 (2 g, 3.7 mmol) and dissolving it in 40 mL of acetic acid in a 250 mL round-bottom flask, replacing the gas, and then adding Br2 (1.19 g, 7.4 mmol) dropwise to the flask. The reactants are allowed to react at room temperature for 12 hours. The solvent is then dried and extracted with dichloromethane and sodium thiosulfate solution. The solvent is then dried to obtain a crude product, which is then separated and purified by silica gel column chromatography to obtain a solid product, namely compound 4 (2.22 g, yield 86%); HRMS (m / z, MALDI): Calc. for C 28 H 23 Br2NO2S4,[M+H] + :693.55,found:692.90.

[0205] (IV) The synthesis of compound 5 comprises the following steps: In a 100 mL round-bottom flask, compound 4 (2 g, 2.89 mmol) and 5-hexane-2-thiopheneboronic acid (1.41 g, 6.6 mmol) were weighed and dissolved in 30 mL of toluene / water (5:1). The mixture was purged with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (0.17 g, 0.14 mmol) and K2CO3 (0.92 g, 6.6 mmol) were added to the reaction system under argon protection. The reaction mixture was refluxed at 110°C for 24 hours. The mixture was cooled to room temperature, the toluene was evaporated, and the mixture was extracted with dichloromethane. The solvent was evaporated to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain a red solid, namely compound 5 (1.90 g, 76% yield); HRMS (m / z, MALDI): Calc. for: C 51 H 71 N3O4S5,[M+H] + :868.32,found:867.24.

[0206] (V) The synthesis of compound 6 comprises: weighing compound 5 (1 g, 1.15 mmol) and dissolving it in 40 mL of a solution of nitromethane and dichloromethane (volume ratio of 1:1) in a 250 mL round-bottom flask, replacing the gas, and then adding FeCl3 (2.06 g, 8.8 mmol) to the flask. The reactants were refluxed at 50°C for 12 hours. The solvent was dried and extracted with dichloromethane. The solvent was dried to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain a solid product, namely compound 6 (0.72 g, yield 71%); HRMS (m / z, MALDI): Calc. for C 17 H7N3OS,[M+H] + :864.29, found:863.21. (VI) Synthesis of compound 7, comprising: adding compound 6 (0.5 g, 0.57 mmol) and anhydrous N,N-dimethylformamide (25 mL) to a 100 mL three-necked flask, stirring at 0°C for several minutes, and then adding phosphorus oxychloride (1.5 mL). The reaction solution was stirred at 0°C for 1 hour, then the temperature was raised to 90°C and stirred overnight (10-12 hours), cooled to room temperature, extracted with dichloromethane, and the solvent was evaporated. The product was separated and purified by silica gel column chromatography to obtain compound 7 (0.43 g, yield 82%); HRMS (m / z, MALDI): Calc. for: C50H49NO4S6, [M+H] + :920.31,found:919.20.

[0207] (VII) Synthesis of PhITT-4F, comprising: dissolving compound 7 (300 mg, 0.32 mmol) and 5,6-difluoro-3-(dicyanomethylidene)indone (389.2 mg, 1.01 mmol) in 50 mL of chloroform in a 100 mL round-bottom flask, replacing the gas three times, protecting with argon, slowly adding 2.5 mL of pyridine while stirring, and reflux the mixture at 65°C under argon for 12 h. The mixture was cooled to room temperature and poured into 300 mL of anhydrous methanol, filtered to obtain a crude product, and separated and purified by silica gel column chromatography to obtain a dark blue solid, which is the receptor material PhITT-4F (315.5 mg, yield 72%). HRMS (m / z, MALDI): Calc. for: C 74 H 53 F4N5O4S6,[M+H] + :1344.62,found:1343.24.

[0208] Example 2

[0209] This embodiment discloses a fused ring receptor material PhITT-4Cl based on benzimide. The difference between its preparation reaction process and that of Example 1 is only that:

[0210] In step (VII), 5,6-dichloro-3-(dicyanomethylene)indone in an equal amount was used to replace 5,6-difluoro-3-(dicyanomethylene)indone in Example 1. Specifically, compound 4 (300 mg, 0.31 mmol) and 5,6-dichloro-3-(dicyanomethylene)indone (209 mg, 0.71 mmol) were dissolved in 50 mL of chloroform in a 100 mL round-bottom flask. The gas was replaced three times under argon protection. 2.5 mL of pyridine was slowly added while stirring. The mixture was refluxed under argon protection for 12 hours, cooled to room temperature, poured into 300 mL of anhydrous methanol, and filtered to obtain a crude product. The product was separated and purified by silica gel column chromatography to obtain a dark blue solid, which was the receptor material PhITT-4Cl (324.24 mg, yield 71%). HRMS (m / z, MALDI): Calc. for: C 92 H 96 F2N8O2S7,[M+H] + :1410.43,found:1410.12.

[0211]

[0212] Example 3

[0213] This embodiment discloses an organic photovoltaic cell (OPV), the structural diagram of which is shown in FIG. Figure 3As shown, it includes a substrate, a hole transport layer, an active layer, an electron transport layer and a metal electrode stacked in sequence, and its preparation process includes:

[0214] (I) Wipe an ITO glass sheet with an area of 5 cm × 5 cm with a dust-free cloth moistened with anhydrous ethanol and place it in a glass container containing an ITO glass holder. Ultrasonic cleaning is performed using glass cleaning solution, ultrapure water, isopropyl alcohol, and anhydrous ethanol in sequence. Each ultrasonic cleaning lasts approximately 30 minutes. The cleaned ITO glass is blown dry with a nitrogen gun and then placed in a UV ozone cleaning machine for 30 minutes before being placed in a culture dish for later use.

[0215] (II) At room temperature and in air, place the ITO glass in the center of the spin coater's chuck. Turn on the vacuum pump to secure the ITO glass, and use an ear bulb to blow away impurities on the ITO glass surface. Use a 2mL syringe to spread a 5°C PEDOT:PSS aqueous solution (concentration approximately 1.5wt%) of the hole transport layer over the ITO glass surface. Set the spin coater speed to 4500 r / min and the spin time to 30s, then turn on the spin switch to spin coat. The PEDOT:PSS film-coated ITO glass was annealed on a heating plate at 150°C for 10 minutes to obtain a PEDOT:PSS hole transport layer with a thickness of 40nm.

[0216] (III) A chloroform solution (10-30 mg / mL) of a mixture of the polymer donor materials PM6 and L8-BO, the organic acceptor material PhITT-4F prepared in Example 1 (the weight ratio of the three materials was 1:1.2:0.1), and the additive 1,8-diiodooctane (mass fraction 0.25%-3%) was spin-coated onto the PEDOT:PSS anode modification layer to form the device's active layer. The active layer had a thickness of 100 nm. Finally, a layer of approximately 10 nm thick PNDIT-F3N was spin-coated as an electron transport layer, and Ag (100 nm) was spin-coated as the device metal electrode, resulting in a solar cell structure: ITO / PEDOT:PSS / active layer / PNDIT-F3N / Ag.

[0217] Example 4

[0218] This embodiment discloses an organic photovoltaic cell (OPV), which differs from embodiment 3 only in that in step (III), the acceptor material PhITT-4Cl obtained in embodiment 2 is used to replace PhITT-4F.

[0219] Example 5

[0220] This embodiment discloses an organic photovoltaic cell (OPV), which differs from Example 3 only in that: in step (III), the mass ratio of PM6, L8-BO and PhITz-4F used in this embodiment is 1:0:1.3.

[0221] Comparative Example 1

[0222] This comparative example discloses an organic photovoltaic cell (OPV), which differs from Example 3 only in that the active layer of the OPV in this comparative example does not contain PhITT-4F. Specifically, the mass ratio of PM6, L8-BO, and PhITT-4F used in this comparative example is 1:1.3:0.

[0223] Test example

[0224] This test example conducted a performance test on the organic photovoltaic cells obtained in the examples and comparative examples, specifically including:

[0225] The energy conversion efficiency of organic photovoltaic cells is calculated using Guangyan SS-F5-3A as a solar simulator at 100mW / cm 2 The photovoltaic performance of the device was tested under light intensity, and the light intensity was calibrated by a standard single-crystal silicon solar cell (SRC-00019); the JV curve was measured using a Keithley 2400. The open circuit voltage V of each organic photovoltaic cell was obtained from the test. oc , short-circuit current J sc The corresponding photoelectric conversion efficiency is calculated based on the three parameters of fill factor FF. The test results are shown in Table 1. The JV curves of the organic photovoltaic cells in Examples 3-4 and Comparative Example 1 are shown in Table 1. Figure 4-5 As shown (the curves in the figure partially overlap), the EQE curves of the organic photovoltaic cells in Examples 3-4 are as follows Figure 6 shown.

[0226] Table 1

[0227]

[0228]

[0229] From the above, we can see that the open circuit voltage V oc =0.86V, short-circuit current J sc =24.77mA / cm 2 , fill factor FF = 76%, conversion efficiency PCE = 16.61%. The open circuit voltage V of the solar cell device with PhITT-4Cl as the third component of the PM6:L8-BO active layer oc Can reach above 0.87V, short circuit current J sc Up to 24.91mA / cm 2 The fill factor FF can reach more than 78%, and the conversion efficiency PCE can reach more than 17.02%. The open circuit voltage V of the solar cell device with PhITT-4F as the third component of the PM6:L8-BO active layer isoc Can reach above 0.87V, short circuit current J sc Up to 25.40mA / cm 2 Above, the filling factor FF can reach more than 77%, and the conversion efficiency PCE can reach more than 17.10%.

[0230] It can be seen that the application of the condensed ring acceptor material based on benzimide in the present invention in solar cell devices can effectively increase the short-circuit current J of the device. SC , that is, to increase the maximum output current of solar cells, broaden the application scenarios of solar cells. And the condensed ring acceptor material based on benzimide in the present invention as the third component can obtain a higher photoelectric conversion efficiency than the binary system, where the open circuit voltage V oc , fill factor FF, short circuit current J sc There has been a significant improvement.

[0231] Figure 6 The integrated short-circuit currents obtained from the EQE curve are 23.93 mA / cm 2 and 24.12 mA / cm 2 , which is within 5% of the test value, indicating that the device data is highly reliable.

[0232] In summary, the present invention improves the PCE of photovoltaic devices by designing a novel benzimide-based fused-ring acceptor material. This acceptor material, with a defined molecular weight, can be prepared at room temperature using a non-halogen solvent and used as the third component in the preparation of OSCs, resulting in a ternary material system for organic photovoltaic cells with low non-radiative recombination losses. This approach not only reduces production costs but also allows for PCEs exceeding 17% for the resulting organic photovoltaic cells, significantly impacting the development of low-cost, large-area, high-efficiency solar cell devices.

[0233] Unless otherwise specified, the term "about" in the present invention means that the error is within the range of ±2%. For example, about 100 is actually 100±2%×100. "Normal temperature" or "room temperature" in the present invention means about 20-30°C unless otherwise specified.

[0234] Unless otherwise specified, “between” in the present invention includes the number itself, for example, “between 2 and 3” includes the endpoint values 2 and 3.

[0235] While the embodiments of the present invention have been described in detail above with reference to the accompanying drawings, the present invention is not limited to the embodiments described above. Various modifications may be made within the scope of knowledge possessed by a person skilled in the art without departing from the spirit of the present invention. Furthermore, the embodiments of the present invention and the features thereof may be combined with one another unless there is a conflict.

Claims

1. A fused ring receptor material based on benzimide, characterized in that: Its chemical formula is shown in Formula I: wherein R1 and R2 are each independently selected from C 1～30 Alkyl, C 1～30 Alkoxy, C 2～30 The alkynyl group, Ar1 and Ar2 are X1 and X2 are independently selected from H, halogen, cyano, halogen substituted or unsubstituted C 1～30 Alkyl, halogen substituted or unsubstituted C 1～30 of alkoxy.

2. The condensed ring receptor material based on benzimide according to claim 1, characterized in that: The benzimide-based fused ring acceptor material is selected from at least one of the following chemical formulas:

3. A method for preparing a fused ring receptor material based on benzimide according to claim 1, characterized in that: The method comprises the following steps: taking a compound of formula II and H-Ar1-H containing an Ar1 group and H-Ar2-H containing an Ar2 group, and subjecting the compound to a Knoevenagel reaction to obtain the condensed ring receptor material based on benzimide, wherein the structural formula of compound II is as follows:

4. An active layer, characterized in that It comprises an acceptor material I and a donor material, wherein the acceptor material I is the condensed ring acceptor material based on benzimide according to any one of claims 1 to 2.

5. The active layer according to claim 4, characterized in that The acceptor material further includes an acceptor material II, wherein the acceptor material II includes at least one of Y6, L8-BO, BTP-4Cl or BTP-eC9; and / or the donor material includes at least one of PM6, PBDB-T, D18 or PTQ-10.

6. The active layer according to claim 5, characterized in that In the active layer, the mass ratio of the donor material, the acceptor material II and the acceptor material I is 1:(0.8-2):(0.02-0.5).

7. A photovoltaic device, characterized in that: The invention comprises the condensed ring receptor material based on benzimide according to any one of claims 1 to 2 or the active layer according to any one of claims 4 to 6.

8. Use of the benzimide-based fused ring acceptor material according to any one of claims 1 to 2 in the preparation of organic photovoltaic cells, organic light-emitting diodes or perovskite solar cells.

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