Compounds, active layer materials and organic photovoltaic cells

Abstract

The application discloses a compound, an active layer material and an organic photovoltaic cell. The structural formula of the compound is shown in formula (I), wherein X represents oxygen, sulfur or selenium, and A is an electron-withdrawing functional group. The compound provided by the application can be used as an acceptor material in an active layer of an organic photovoltaic cell, and a higher photoelectric conversion efficiency is achieved.

Description

Technical Field

[0001] This application relates to the field of organic photovoltaic cell technology, and in particular to a compound, an active layer material, and an organic photovoltaic cell. Background Technology

[0002] Organic photovoltaic (PV) cells have attracted widespread attention due to their lightweight, flexibility, low cost, and ease of large-area fabrication. In recent years, the photoelectric conversion efficiency of PV cells has been continuously improving, with single-junction organic solar cells exceeding 19%, indicating that PV cells have the potential for industrial application. While the photovoltaic efficiency of PV cells has been significantly improved with the continuous development and refinement of molecular design strategies, the increasingly complex molecular structure of active layer materials has led to high costs for high-performance photovoltaic materials, hindering the industrial application of PV cells. Therefore, designing and fabricating organic photovoltaic materials that combine low cost and high performance is crucial for the large-scale fabrication of PV cells.

[0003] In existing organic photovoltaic material design methods, employing a non-fused structure as the central structural unit is one approach to reduce material synthesis costs. However, molecular strategies for low-cost non-fused photovoltaic materials are relatively limited, and photovoltaic cells prepared using these materials exhibit low photoelectric conversion efficiency. Summary of the Invention

[0004] In view of the defects or deficiencies of the existing technology, the purpose of this application is to provide a compound, an active layer material and an organic photovoltaic cell. By introducing branched alkoxy groups that are branched relative to the α site of the oxygen atom on the side chain of the compound molecule, a new type of low-cost organic photovoltaic cell material is synthesized.

[0005] The first aspect of this application is to provide a compound having the structure shown in general formula (I),

[0006]

[0007] Wherein, X is any one of oxygen, sulfur, and selenium;

[0008] Substituents R1, R2, and R3 are each independently selected from hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C2-C20 straight-chain or branched alkenyl, substituted or unsubstituted C2-C20 straight-chain or branched alkynyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 heteroaryl, and substituted or unsubstituted C3-C20 heterocyclic group;

[0009] Substituents R4, R5, and R6 are each independently selected from hydrogen, halogen, cyano, nitro, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C1-C20 straight-chain or branched alkoxy, substituted or unsubstituted C2-C20 straight-chain or branched alkenyl, substituted or unsubstituted C2-C20 straight-chain or branched alkynyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 heteroaryl, and substituted or unsubstituted C3-C20 heterocyclic; the halogen is any one of fluorine, chlorine, bromine, and iodine;

[0010] A is an electron-withdrawing functional group.

[0011] The compounds provided in this application contain branched alkoxy groups branched relative to the α site of the oxygen atom, which belong to a novel non-fused structure acceptor material.

[0012] In some embodiments of this application, the substituents R1, R2, and R3 are each independently selected from C1-C20 straight-chain or branched alkyl groups;

[0013] and / or;

[0014] The substituents R4, R5, and R6 are each independently selected from hydrogen, halogen, cyano, or nitro;

[0015] and / or;

[0016] The A is Any one of the following, and the substituent Y1 is hydrogen, halogen, cyano, nitro, C1-C20 straight-chain or branched alkyl, C1-C20 straight-chain or branched alkoxy, or halogen-substituted C1-C20 straight-chain or branched alkyl.

[0017] In some embodiments of this application, the Any of the following, where substituents Y1 and Y2 may be the same or different, and each is independently selected from hydrogen, halogen, cyano, nitro, C1-C20 straight-chain or branched alkyl, C1-C20 straight-chain or branched alkoxy, or halogen-substituted C1-C20 straight-chain or branched alkyl.

[0018] In some embodiments of this application, the substituents Y1 and Y2 are each independently selected from hydrogen, halogen, methyl, trifluoromethyl, or methoxy.

[0019] In some embodiments of this application, the substituents R1, R2, and R3 are each independently selected from C1-C20 branched alkyl groups.

[0020] In some embodiments of this application, the substituent R1 is independently selected from -CHR. 11 R 12 The substituent R2 is independently selected from -CHR. 21 R22 The substituent R3 is independently selected from -CHR. 31 R 32 ;

[0021] The substituent R 11 R 12 R 21 R 22 R 31 R 32 Each is independently selected from C1-C6 branched alkyl groups.

[0022] In some embodiments of this application, the substituents R4, R5, and R6 are each independently selected from hydrogen and halogens.

[0023] In some embodiments of this application, the structure shown in general formula (II) is provided.

[0024]

[0025] Where X is sulfur;

[0026] Substituent R 11 R 12 R 21 R 22 R 31 R 32 Each is independently selected from C1-C6 alkyl groups, preferably selected from one or two of methyl, ethyl, propyl, and n-butyl groups;

[0027] Substituents R4, R5, and R6 are independently selected from hydrogen;

[0028] A is

[0029] In some embodiments of this application, compounds are selected from the following specific structures:

[0030]

[0031]

[0032] Meanwhile, this application also provides a method for preparing the compound, the reaction route of which is as follows:

[0033]

[0034] Compound 1 and Compound 4 were reacted with n-BuLi in THF solution to synthesize Compound 2;

[0035] Compound 2 and compound 5 were Suzuki coupled to obtain compound 3;

[0036] Compound 3 and the A-type end group are reacted via a knockevenagel reaction to obtain the compound shown in formula (I);

[0037] In the synthetic route, the substituents R1, R2, R3, R4, R5, R6, and A of the compound are defined in the same way as above, and the substituent Z is a C1-C6 alkyl group, preferably methyl or isopropyl.

[0038] In some embodiments of this application, the conditions for the Suzuki coupling of compound 2 and compound 5 are as follows: diethylene glycol dimethyl ether and water are used as reaction solvents, lithium hydroxide monohydrate is added, and the reaction is carried out under the catalysis of tetrakis(triphenylphosphine)palladium, wherein the volume ratio of diethylene glycol dimethyl ether to water is preferably 10:1.

[0039] In some embodiments of this application, the conditions for the Knoevenagel reaction of compound 3 and the A-type end group are the addition of pyridine and the reaction in chloroform solvent at room temperature.

[0040] The second aspect of this application discloses the application of the compound described in the first aspect in organic photovoltaic cells.

[0041] A third aspect of this application discloses an active layer material for an organic photovoltaic cell, comprising the compound described in the first aspect as an acceptor material.

[0042] The fourth aspect of this application discloses an organic photovoltaic cell comprising the active layer material described in the third aspect; the organic photovoltaic cell is preferably an organic solar cell.

[0043] The beneficial technical effects of this application are as follows:

[0044] This application provides a low-cost organic photovoltaic material, which belongs to the category of novel low-cost organic photovoltaic materials. This organic photovoltaic material can achieve high energy conversion efficiency in organic photovoltaic cells, such as a photoelectric conversion efficiency (PCE) of 14% to 20%, and has good application prospects in the field of organic photovoltaic cells. Attached Figure Description

[0045] Various other advantages and benefits will become apparent to those skilled in the art upon reading the following detailed description of preferred embodiments. The accompanying drawings are for illustrative purposes only and are not intended to limit the scope of this application. Furthermore, the same reference numerals denote the same parts throughout the drawings. In the drawings:

[0046] Figure 1 This is the 1H NMR spectrum of the non-fused acceptor of compound 11 obtained in Example 1 of this application;

[0047] Figure 2This is the 1H NMR spectrum of the non-fused acceptor of compound 18 obtained in Example 2 of this application;

[0048] Figure 3 This is the 1H NMR spectrum of the non-fused acceptor of compound 22 obtained in Example 3 of this application;

[0049] Figure 4 This is the absorption spectrum of the non-fused acceptor of compound 11 obtained in Example 1 of this application;

[0050] Figure 5 This is the absorption spectrum of the non-fused acceptor of compound 18 obtained in Example 2 of this application;

[0051] Figure 6 This is the absorption spectrum of the non-fused acceptor of compound 22 obtained in Example 3 of this application;

[0052] Figure 7 The current density-voltage (JV) curve of an organic photovoltaic cell with the structure ITO / PEDOT:PSS / PBQx-TF:Formula II / PDINN / Ag prepared by the non-fused acceptor of compound 11 obtained in Example 1 of this application is measured at AM 1.5G.

[0053] Figure 8 The current density-voltage (JV) curves of an organic photovoltaic cell with the structure ITO / PEDOT:PSS / PBQx-TF:Formula II / PDINN / Ag prepared by the non-fused acceptor of compound 18 obtained in Example 2 of this application were measured at AM 1.5G.

[0054] Figure 9 The current density-voltage (JV) curves of an organic photovoltaic cell with the structure ITO / PEDOT:PSS / PBQx-TF:Formula II / PDINN / Ag prepared by the non-fused acceptor of compound 22 obtained in Example 3 of this application are measured at AM 1.5G.

[0055] Figure 10 The external quantum efficiency (EQE) curve of an organic photovoltaic cell with the structure ITO / PEDOT:PSS / PBQx-TF:Formula II / PDINN / Ag prepared by the non-fused acceptor of compound 11 obtained in Example 1 of this application is measured at AM 1.5G.

[0056] Figure 11 The external quantum efficiency (EQE) curve of an organic photovoltaic cell with the structure ITO / PEDOT:PSS / PBQx-TF:Formula II / PDINN / Ag prepared based on the non-fused acceptor of compound 18 obtained in Example 2 is measured at AM 1.5G.

[0057] Figure 12 The external quantum efficiency (EQE) curve of an organic photovoltaic cell with the structure ITO / PEDOT:PSS / PBQx-TF:Formula II / PDINN / Ag, prepared based on the non-fused acceptor of compound 22 obtained in Example 3, is measured at AM 1.5G. Detailed Implementation

[0058] The following is an explanation and description of the terms and concepts used in this application:

[0059] As used herein, the terms “donor” or “supply” and “acceptor” or “receiver” should be understood as electron donors and electron acceptors, respectively. An “electron donor” should be understood as a chemical entity that donates electrons to another compound or another group of atoms in a compound. An “electron acceptor” should be understood as a chemical entity that accepts electrons transferred from another compound or another group of atoms in a compound. See also International Union of Pure and Applied Chemistry, Compendium of Chemical Technology, Gold Book, Version 2.3.2, August 19, 2012, pp. 477 and 480.

[0060] The compounds and derivatives provided in this application may be named according to the IUPAC (International Union of Pure and Applied Chemistry) or CAS (Chemical Abstracts Service, Columbus, OH) nomenclature systems.

[0061] "Substitution" refers to the replacement of hydrogen atoms in a molecule with other different atoms or molecules. The "substitution" is selected from hydrogen, halogen, cyano, nitro, C1-C20 straight-chain or branched alkyl, C1-C20 straight-chain or branched alkoxy, C2-C20 straight-chain or branched alkenyl, C2-C20 straight-chain or branched alkynyl, C6-C20 aryl, C6-C20 heteroaryl, and C3-C20 heterocyclic.

[0062] The minimum and maximum carbon atom content in hydrocarbon groups are indicated by prefixes. For example, the prefix Ca-balkyl indicates any alkyl group containing "a" to "b" carbon atoms. Thus, for example, "C1-4alkyl" refers to alkyl groups containing 1 to 4 carbon atoms.

[0063] “Alkyl” refers to a saturated hydrocarbon chain having a specified number of member atoms. For example, C1-6 alkyl refers to an alkyl group having 1 to 6 member atoms, such as 1 to 4 member atoms. Alkyl groups can be straight-chain or branched. Representative branched alkyl groups have one, two, or three branches. Alkyl groups may optionally be substituted by one or more substituents as defined herein. Alkyl groups include methyl, ethyl, propyl (n-propyl and isopropyl), butyl (n-butyl, isobutyl, and tert-butyl), pentyl (n-pentyl, isopentyl, and neopentyl), and hexyl. “C312 alkyl” should be understood to preferably represent a straight-chain or branched saturated monovalent hydrocarbon group having 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms. The alkyl group is, for example, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, or 1,2-dimethylbutyl, or isomers thereof. In particular, the group has 4, 5, 6, 7, or 8 carbon atoms (“C48 alkyl”), for example, butyl, isopropyl, pentyl, hexyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-ethylhexyl, etc. The alkyl group may also be part of other groups, such as C1-C6 alkoxy groups.

[0064] "Alkenyl" refers to a straight-chain or branched hydrocarbon group having 2 to 10 carbon atoms, and in some embodiments 2 to 6 carbon atoms or 2 to 4 carbon atoms and having at least one vinyl unsaturated site (>C=C<). For example, (Ca-Cb)alkenyl refers to an alkenyl group having a to b carbon atoms and is intended to include, for example, vinyl, propenyl, isopropenyl, 1,3-butadienyl, etc.

[0065] "Alynyl" refers to a straight-chain monovalent hydrocarbon group or a branched monovalent hydrocarbon group containing at least one triple bond. The term "alkynyl" is also intended to include hydrocarbon groups having one triple bond and one double bond. For example, (C2-C6) alkynyl is intended to include ethynyl, propynyl, etc.

[0066] "Halogen" refers to fluorine, chlorine, bromine, or iodine.

[0067] "Heterocyclic", "heterocyclic group", "heterocyclic alkyl", and "heterocyclic alkane" refer to saturated rings or non-aromatic unsaturated rings containing at least one heteroatom; where heteroatoms refer to nitrogen, oxygen, and sulfur atoms.

[0068] "Aromatic heterocycle" refers to an aromatic unsaturated ring containing at least one heteroatom; where the heteroatom refers to a nitrogen atom, an oxygen atom, or a sulfur atom.

[0069] For organic photovoltaic materials, alkyl side chains have a crucial impact on the photoelectric properties of the materials. Branched alkyl groups with different branch positions have different steric hindrances, which affect the stacking structure of the materials and thus have a significant impact on the charge mobility of the resulting materials. α-branched alkyl groups have greater steric hindrance than β-branched or alkyl groups with later branching sites. However, most existing materials employing non-fused conjugated structures use β-branched or alkyl groups with later branching sites, and α-branched alkyl groups are rarely used.

[0070] Therefore, it is necessary to apply this type of branched alkyl group to organic photovoltaic materials with a non-fused central structural unit.

[0071] The purpose of this application is to provide a compound, an active layer material, and an organic photovoltaic cell. A novel, low-cost organic photovoltaic cell material is synthesized by introducing branched alkoxy groups relative to the α-site of the oxygen atom onto the side chain of the compound molecule. To better understand the technical solution of this application, the embodiments are described in detail below with reference to the accompanying drawings.

[0072] It should be understood that the described embodiments are merely some, not all, of the embodiments in this application. All other embodiments obtained by those skilled in the art based on the embodiments in this application without inventive effort are within the scope of protection of this application.

[0073] The terminology used in the embodiments of this application is for the purpose of describing particular embodiments only and is not intended to be limiting of this application. The singular forms “a,” “the,” and “the” used in the embodiments of this application and the appended claims are also intended to include the plural forms unless the context clearly indicates otherwise.

[0074] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods.

[0075] Unless otherwise specified, all materials and reagents used in the following examples are commercially available.

[0076] This application can employ conventional organic chemistry techniques within the art. In the following examples, efforts have been made to ensure the accuracy of the figures used (including quantities, temperatures, reaction times, etc.), but some experimental errors and biases should be considered. Temperatures (in degrees Celsius) used in the following examples are expressed in °C, and pressures are at or near atmospheric pressure. All solvents were purchased as HPLC grade, and all reactions were carried out under argon protection. Unless otherwise specified, all reagents were obtained commercially.

[0077] Example 1

[0078] Compound 11 was provided:

[0079]

[0080] The synthetic route for compound 11 is as follows:

[0081]

[0082] (1) Synthesis of compound 9

[0083] Compound 8 (1.8 g, 3.88 mmol) was dissolved in ultradry THF (30 mL), cooled to -78 °C, and n-BuLi (2.4 M, 9.30 mmol) was added dropwise under argon protection. The mixture was stirred at -78 °C for 2 hours, then compound 12 (1.53 g, 9.7 mmol) was added, and the mixture was stirred at -78 °C for another 2 hours. After quenching with water, the mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The product was used directly in the next step without purification.

[0084] (2) Synthesis of compound 10

[0085] Compound 9 (0.9 g, 1.61 mmol), compound 13 (0.98 g, 3.22 mol), and LiOH·H₂O (0.34 g, 8.05 mmol) were dissolved in 20 mL of diethylene glycol dimethyl ether (DMDE) and 2 mL of H₂O. The reaction mixture was purged with argon for 5 min, and Pd(PPh₃)₄ (93 mg, 0.08 mmol) was added. After purging with argon for another 10 min, the reaction mixture was stirred at 105 °C for 3 h. The mixture was then extracted with dichloromethane. The organic phase was dried over MgSO₄, filtered, and the solvent was removed by rotary evaporation. Purification by silica gel column chromatography (petroleum ether / ethyl acetate, 30 / 1) gave a yellow solid product (0.74 g, 61%).

[0086] (3) Synthesis of compound 11

[0087] A mixture of compound 10 (150 mg, 0.2 mmol), compound 14 (184 mg, 0.80 mmol), chloroform (6 mL), and pyridine (0.2 mL) was stirred at room temperature for 2 h. Then, methanol (40 mL) was added to precipitate the crude product. After filtration, the residue was purified by silica gel column chromatography (chloroform) to give a black solid product (205 mg, 87%). The 1H NMR spectrum of the non-fused acceptor of compound 11 is shown in the attached figure in the product manual. Figure 1 .

[0088] Example 2

[0089] Compound 18 was provided:

[0090]

[0091] The synthetic route for compound 18 is as follows:

[0092]

[0093] (1) Synthesis of compound 16

[0094] Compound 15 (3.7 g, 7.97 mmol) was dissolved in ultradry THF (35 mL), cooled to -78 °C, and n-BuLi (2.4 M, 19.1 mmol) was added dropwise under argon protection. The mixture was stirred at -78 °C for 2 hours, then compound 19 (3.75 g, 19.92 mmol) was added, and the mixture was stirred at -78 °C for another 2 hours. After quenching with water, the mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The product was used directly in the next step without purification.

[0095] (2) Synthesis of compound 17

[0096] Compound 16 (0.68 g, 1.19 mmol), compound 13 (0.91 g, 2.98 mol), and LiOH·H₂O (0.25 g, 5.95 mmol) were dissolved in 20 mL of diethylene glycol dimethyl ether (DMDE) and 1 mL of H₂O. The reaction mixture was purged with argon for 5 min, and Pd(PPh₃)₄ (69 mg, 0.06 mmol) was added. After purging with argon for another 10 min, the reaction mixture was stirred at 105 °C for 3 h. The mixture was then extracted with dichloromethane. The organic phase was dried over MgSO₄, filtered, and the solvent was removed by rotary evaporation. Purification by silica gel column chromatography (petroleum ether / ethyl acetate, 30 / 1) gave a yellow solid product (0.65 g, 72%).

[0097] (3) Synthesis of compound 18

[0098] A mixture of compound 17 (108 mg, 0.14 mmol), compound 14 (132 mg, 0.57 mmol), chloroform (6 mL), and pyridine (0.2 mL) was stirred at room temperature for 2 h. Then, methanol (40 mL) was added to precipitate the crude product. After filtration, the residue was purified by silica gel column chromatography (chloroform) to give a black solid product (150 mg, 89%). The 1H NMR spectrum of the non-fused acceptor of compound 18 is shown in the attached figure in the product manual. Figure 2 .

[0099] Example 3

[0100] Compound 22 was provided:

[0101]

[0102] The synthetic route for compound 22 is as follows:

[0103]

[0104] (1) Synthesis of compound 20

[0105] Compound 19 (1.46 g, 3.58 mmol) was dissolved in ultradry THF (30 mL), cooled to -78 °C, and n-BuLi (2.4 M, 8.58 mmol) was added dropwise under argon protection. The mixture was stirred at -78 °C for 2 hours, then compound 12 (1.41 g, 8.95 mmol) was added, and the mixture was stirred at -78 °C for another 2 hours. After quenching with water, the mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The product was used directly in the next step without purification.

[0106] (2) Synthesis of compound 21

[0107] Compound 20 (0.52 g, 1.04 mmol), compound 13 (0.63 g, 2.07 mol), and LiOH·H₂O (0.22 g, 5.35 mmol) were dissolved in 10 mL of diethylene glycol dimethyl ether (DMDE) and 1 mL of H₂O. The reaction mixture was purged with argon for 5 min, and Pd(PPh₃)₄ (60 mg, 0.05 mmol) was added. After purging with argon for another 10 min, the reaction mixture was stirred at 105 °C for 3 h. The mixture was then extracted with dichloromethane. The organic phase was dried over MgSO₄, filtered, and the solvent was removed by rotary evaporation. Purification by silica gel column chromatography (petroleum ether / ethyl acetate, 30 / 1) gave a yellow solid product (0.56 g, 66%).

[0108] (3) Synthesis of compound 22

[0109] A mixture of compound 21 (100 mg, 0.14 mmol), compound 14 (132 mg, 0.57 mmol), chloroform (6 mL), and pyridine (0.2 mL) was stirred at room temperature for 2 h. Then, methanol (40 mL) was added to precipitate the crude product. After filtration, the residue was purified by silica gel column chromatography (chloroform) to give a black solid product (135 mg, 86%). The 1H NMR spectrum of the non-fused acceptor of compound 22 is shown in the attached figure in the product manual. Figure 3 .

[0110] Test case

[0111] (1) UV-Vis absorption spectroscopy measurement experiments of the acceptor materials of compounds 11, 18 and 22 prepared in Examples 1-3

[0112] The acceptors prepared in Examples 1-3 were dissolved in chloroform. The solutions were placed in cuvettes, and the absorption spectra of the solutions were measured using a UV-Vis absorption spectrometer. Separately, the prepared chloroform solutions were spin-coated onto a quartz plate to prepare thin film samples. The absorption spectra of the thin films were measured using a UV-Vis absorption spectrometer. (See attached figures in the instruction manual.) Figures 4-6 It can be seen that the absorption peaks of the acceptor materials of compounds 11, 18, and 22 are approximately 900 nm.

[0113] (2) Experimental fabrication of organic solar cell devices using the acceptor materials of compounds 11, 18 and 22 obtained in Examples 1-3

[0114] A PEDOT:PSS film of approximately 10 nm thickness was spin-coated onto indium tin oxide (ITO) conductive glass and annealed at 160 °C for 15 minutes. The substrate was then transferred to a glove box, and a polymer molecule (abbreviated as PBQx-TF, synthesized by the applicant and already disclosed) was spin-coated onto the aforementioned interface layer film in a blend solution of compound 11, compound 18, or compound 22 (mass ratio 1:1.2, total concentration 13.2 mg / mL, 0.5% chloronaphthalene as solvent) to obtain an active layer film of approximately 100 nm. The film was then annealed at 100 °C for 10 minutes. After the substrate cooled, a 1.5 mg / mL PDINN methanol solution was spin-coated onto it to obtain a cathode interface layer film of approximately 10 nm thickness. Finally, the device was placed in a high-vacuum evaporation chamber and annealed at approximately 10 °C. -4 Organic photovoltaic cells were fabricated by vacuum evaporation of approximately 100 nm thick Ag as the top electrode under a vacuum of Pa. A xenon lamp (AM 1.5G, 100 mW / cm²) was used to simulate sunlight in a glove box filled with N₂. 2 The current density-voltage curve of the measuring device is shown in the attached figure in the instruction manual. Figures 7-9 The open-circuit voltage (VOC) of the organic photovoltaic cell based on compound 11 acceptor material is 0.807V, and the short-circuit current (JSC) is 23.09mA / cm². -2 The fill factor FF = 0.761, the photoelectric conversion efficiency PCE = 14.5%; the open-circuit voltage VOC of the organic photovoltaic cell based on compound 18 acceptor material is 0.800V, and the short-circuit current JSC = 25.86mAcm. -2 The fill factor FF = 0.779, the photoelectric conversion efficiency PCE = 16.0%; the open-circuit voltage VOC of the organic photovoltaic cell based on compound 22 acceptor material is 0.801V, and the short-circuit current JSC = 26.16mAcm. -2The fill factor FF = 0.781 and the photoelectric conversion efficiency PCE = 16.8%. This demonstrates that compound 11, compound 18, or compound 22 have excellent performance as acceptor materials for organic photovoltaic cells.

[0115] (3) Experimental study on the external quantum efficiency of organic solar cell devices using the acceptor materials of compounds 11, 18 and 22 prepared in Examples 1-3

[0116] Organic solar cell devices were fabricated using the acceptor materials, compounds 11, 18, and 22, obtained in Examples 1-3, following the steps in Test Example 2. The external quantum efficiency was measured using the Enli external quantum efficiency meter from Taiwan Guangyan Corporation. The results are shown in the accompanying drawings. Figures 10-12 As shown in the accompanying figures, the external quantum efficiency of solar cell devices based on compounds 11, 18, or 22 is generally greater than 60% across the entire spectral range, demonstrating the excellent photoelectric conversion capabilities of these materials.

[0117] In summary, the compound provided in this application can be used as an acceptor material in the active layer of an organic photovoltaic cell, achieving high photoelectric conversion efficiency. Furthermore, the synthesis of this compound is not complex, and it can be further manufactured into large-area organic photovoltaic cells using a low-cost solution coating process, demonstrating broad application prospects while reducing production costs.

[0118] The above description of the embodiments is only for the purpose of helping to understand the method and core idea of ​​this application; at the same time, for those skilled in the art, there will be changes in the specific implementation and application scope based on the idea of ​​this application. Therefore, the content of this specification should not be construed as a limitation of this application.

[0119] Certain terms are used in the specification and claims to refer to specific components. Those skilled in the art will understand that hardware manufacturers may use different names to refer to the same component. This specification and claims do not distinguish components based on differences in name, but rather on differences in function. The terms "comprising" and "including" used throughout the specification and claims are open-ended and should be interpreted as "comprising / including but not limited to". "Approximately" means that within an acceptable margin of error, those skilled in the art can solve the technical problem and substantially achieve the technical effect within a certain margin of error. The following descriptions in the specification are preferred embodiments for carrying out this application; however, these descriptions are for the purpose of illustrating the general principles of this application and are not intended to limit the scope of this application. The scope of protection of this application shall be determined by the appended claims.

[0120] It should also be noted that the terms "comprising," "including," or any other variations thereof are intended to cover non-exclusive inclusion, such that a product or system comprising a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such a product or system. Without further limitation, an element defined by the phrase "comprising one..." does not exclude the presence of other identical elements in the product or system that includes said element.

[0121] It should be understood that the term "and / or" used in this article is merely a description of the relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, A and B existing simultaneously, and B existing alone. Additionally, the character " / " in this article generally indicates that the preceding and following related objects have an "or" relationship.

[0122] The foregoing description illustrates and describes several preferred embodiments of this application. However, as previously stated, it should be understood that this application is not limited to the forms disclosed herein and should not be construed as excluding other embodiments. It can be used in various other combinations, modifications, and environments, and can be altered within the scope of the application concept described herein through the foregoing teachings or techniques or knowledge in related fields. Any modifications and variations made by those skilled in the art that do not depart from the spirit and scope of this application should be protected within the scope of the appended claims.

Claims

1. A compound, characterized in that, It has the structure shown in general formula (II), (II) Where X is sulfur; Substituent R 11 R 12 R 21 R 22 R 31 R 32 Each is independently selected from C1-C6 alkyl groups; The substituents R4, R5, and R6 are each independently selected from hydrogen or halogen; The A is ; And the substituent Y1 is any one of hydrogen, halogen, cyano, nitro, C1-C20 straight-chain or branched alkyl, C1-C20 straight-chain or branched alkoxy, or halogen-substituted C1-C20 straight-chain or branched alkyl.

2. The compound of claim 1, wherein The substituent R 11 R 12 R 21 R 22 R 31 R 32 Each is independently selected from methyl, ethyl, propyl, and n-butyl; The A is .

3. The compound of claim 1 or 2, wherein Compounds selected from the following specific structures: 、 、 。 4. The use of any compound according to any one of claims 1 to 3 in an organic photovoltaic cell.

5. An active layer material for an organic photovoltaic cell, characterized by: The compound comprising any one of claims 1 to 3 may be used as a receptor material.

6. An organic photovoltaic cell, characterized by: It includes the active layer material as described in claim 5; the organic photovoltaic cell is an organic solar cell.

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