Small molecule acceptor material containing eight-membered ring and application of small molecule acceptor material
By developing small molecule acceptor materials containing eight-membered rings and employing an A-π-D-π-A structure and specific unit combinations, the problems of low efficiency and high synthesis cost of non-fused ring acceptor materials have been solved, achieving high-efficiency photoelectric conversion performance and easy synthesis, making them suitable for the industrialization of organic solar cells.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SUZHOU UNIV OF SCI & TECH
- Filing Date
- 2026-02-02
- Publication Date
- 2026-05-12
AI Technical Summary
The efficiency of organic solar cell photovoltaic devices made from existing non-fused-ring acceptor materials is still lower than that made from fused-ring acceptor materials, and their synthesis cost is higher, which is not conducive to industrial application.
A small molecule acceptor material containing an eight-membered ring was developed, adopting an A-π-D-π-A structure. Novel electron-donating and connecting units were introduced, and thiophene-thiophene and electron-withdrawing units were combined to achieve synergistic optimization of the molecular planarity and electron-donating properties of the material. It can be applied as an acceptor material in organic solar cells.
It achieves efficient charge dissociation and transport, improves photoelectric conversion performance, and the material is simple and easy to synthesize, making it more suitable for industrialization.
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Figure CN122010984A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of organic optoelectronic materials technology, specifically to a small molecule acceptor material containing an eight-membered ring and its applications. Background Technology
[0002] Organic solar cells (OSCs) have attracted widespread attention due to their advantages such as solution-processability, lightweight, flexibility, ability to be fabricated in large-area roll-to-roll with semi-transparent surfaces, and the ability to be produced in a variety of vibrant colors. Researchers have conducted extensive studies on device structure, active layer materials, active layer morphology, interface layer materials, and device fabrication processes. Among these, research on the optimization of the chemical structure of active layer materials has been the most in-depth, and current devices have achieved rapid advancements in photoelectric conversion efficiency (PCE).
[0003] The active layer material of organic solar cells mainly consists of two parts: donor materials and acceptor materials. The donor material mainly uses polymer donors with alternating donor-acceptor (DA) copolymerization, while the acceptor material mainly includes fullerene acceptors and their derivatives and non-fullerene acceptors, which were widely used in the early stages. In particular, fused ring acceptor materials with acceptor-donor-acceptor (ADA) structures have greatly promoted the development of organic solar cells.
[0004] Although significant progress has been made in organic solar cells based on fused-ring acceptor materials, these materials typically involve long synthetic routes. In particular, Friedel-Crafts alkylation ring-closure reactions often exhibit substrate adaptability, leading to lower reaction yields and consequently, relatively high synthesis costs, hindering their industrial application. In contrast, non-fused-ring acceptor materials offer simpler synthetic routes and higher yields, effectively reducing synthesis costs. Against this backdrop, developing low-cost non-fused acceptors has become a crucial research topic in the field of organic solar cells (OSCs).
[0005] However, the efficiency of non-fused-ring acceptor photovoltaic devices still lags behind that of fused-ring acceptor photovoltaic devices and needs further improvement. Developing novel, high-efficiency non-fused-ring small molecule acceptor materials from a molecular design perspective is of great significance to the industrial development of OSC. Summary of the Invention
[0006] To address the above technical problems, this invention provides a small molecule acceptor material containing an eight-membered ring and its applications. The eight-membered ring of this invention is an eight-membered nitrogen heterocycle with good electron-donating ability. When used as a small molecule acceptor material in organic solar cells, it achieves better photoelectric conversion efficiency.
[0007] The first objective of this invention is to provide a small molecule acceptor material containing an eight-membered ring, the structure of which is shown below: ; R1, R3, and R4 are independently selected from: -H, -D, C1~C20 straight-chain alkyl groups or C3~C20 branched-chain alkyl groups; R2 is independently selected from: -H, -D, -F, -Cl, -Br, or -I.
[0008] In some embodiments of the present invention, R1 is selected from straight-chain alkyl groups of C1 to C15, or branched-chain alkyl groups of C3 to C15.
[0009] In some embodiments of the present invention, R1 is selected from... or , where * represents the connection site.
[0010] In some embodiments of the present invention, R3 and R4 are independently selected from: -H, -D, C1~C10 straight-chain alkyl or C3~C10 branched alkyl.
[0011] In some embodiments of the present invention, R3 and R4 are independently selected from: -H, -D, -C4H9 (n-butyl), -C6H13 (n-hexyl), or -C8H17 (n-octyl).
[0012] In some embodiments of the present invention, R3 is selected from -H; R4 is selected from -H, -D, -C4H9, -C6H13 or -C8H17.
[0013] In some embodiments of the present invention, the general formula is as follows: Independently selected from any of the following groups: .
[0014] In one embodiment, Selected from the same group.
[0015] In some embodiments of the present invention, one or more of the following structures are included: , , , , , , .
[0016] A second objective of this invention is to provide an organic solar cell device comprising a small molecule acceptor material containing an eight-membered ring as described above.
[0017] In some embodiments of the present invention, the organic solar cell device includes at least a cathode, an anode, and an active layer located between the cathode and the anode, wherein the acceptor material of the active layer comprises a small molecule acceptor material containing an eight-membered ring as described above.
[0018] A third objective of the present invention is to provide an organic solar cell device for automobiles, buildings, or the Internet of Things, including the organic solar cell device.
[0019] In some embodiments of the present invention, the active layer further includes a donor material selected from one or more of PM6, PM7 and D18.
[0020] In some embodiments of the present invention, the organic solar cell device includes an anode, an anode buffer layer, an active layer, a cathode buffer layer, and a cathode layer stacked thereon.
[0021] In some embodiments of the present invention, the anode material is selected from indium tin oxide (ITO).
[0022] In some embodiments of the present invention, the cathode material is selected from silver (Ag) or aluminum (Al).
[0023] In some embodiments of the present invention, the anode buffer layer material may be selected from poly(styrene sulfonic acid) PEDOT:PSS (poly(3,4-ethylenedioxythiophene)) or molybdenum trioxide (MoO3).
[0024] In some embodiments of the present invention, the cathode buffer layer material is selected from zinc oxide, PFN-Br, PDINN, PDINO, PNDIT-F3N-Br or PNDIT-F3N.
[0025] The beneficial effects of this invention are: The small molecule acceptor material containing an eight-membered ring described in this application has a non-fused-ring acceptor with an A-π-D-π-A structure, which is achieved by introducing a novel electron-donating unit D. This 8-membered ring structure possesses good molecular planarity and suitable electron-donating properties. The connecting unit π is selected from substituted or unsubstituted thiophene-thiophene, and the electron-withdrawing unit A is selected from... This allows for the synergistic optimization of compound structures, thereby regulating the photovoltaic performance of materials, such as energy levels and morphology. When these materials are used as acceptor materials in organic solar cell devices, they exhibit efficient charge dissociation and transport, achieving excellent photoelectric conversion performance.
[0026] Furthermore, the small molecule acceptor material containing an eight-membered ring described in this application is simple to synthesize and more suitable for industrialization. Attached Figure Description
[0027] To make the content of this invention easier to understand, the invention will be further described in detail below with reference to specific embodiments and accompanying drawings, wherein... Figure 1 A schematic diagram of the structure of an organic solar cell device fabricated for a device embodiment.
[0028] Figure 2 Here is the mass spectrum of compound (5). Detailed Implementation
[0029] The present invention will be further described below with reference to the accompanying drawings and specific embodiments, so that those skilled in the art can better understand and implement the present invention. However, the embodiments described are not intended to limit the present invention.
[0030] In the embodiments of the present invention, R3 and R4 are independently selected from -C4H9 (n-butyl), -C6H13 (n-hexyl), or -C8H17 (n-octyl).
[0031] Example 1: This embodiment provides the synthesis of compound (2), as detailed below: (1) Reaction route diagram: .
[0032] (2) Specific synthesis steps: 1) Synthesis of compounds 1-2: Accurately weigh 31.7 g (100 mmol) of compound 1-1 into a 1000 mL three-necked flask, add approximately 400 mL of anhydrous DMF, purge the mixture three times with nitrogen, and cool to approximately 0 °C. Slowly add a DMF solution of N-bromosuccinimide (NBS) (35.6 g dissolved in 350 mL of DMF) dropwise to the reaction system. After the addition is complete, react at room temperature overnight. After the starting material has completely reacted, wash with water, extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Recrystallize the crude product from toluene / methanol to give approximately 35.12 g of compound 1-2, yield: 73.9%. MS: 475.41.
[0033] 2) Synthesis of compounds 1-4: Accurately weigh compounds 1-2 (16.64 g, 35 mmol), compounds 1-3 (10 g, 40 mmol), tetrabutylammonium bromide (1.1 g, 3.5 mmol), and 10 mL of sodium hydroxide aqueous solution (50%, w / w). After purging with nitrogen three times, the mixture was heated to 50 °C and reacted for 4 hours. After the starting materials had completely reacted, the mixture was washed with water, extracted with dichloromethane, and the organic phases were combined. After drying with anhydrous sodium sulfate, excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with petroleum ether as the eluent to obtain approximately 18.24 g of compounds 1-4, yield: 80.9%. MS: 643.85.
[0034] 3) Synthesis of compounds 1-5: Accurately weigh compounds 1-4 (18 g, 28 mmol), pinacol diborate (21.3 g, 84 mmol), Pd(PPh3)2Cl2 (0.35 g, 0.5 mmol), and potassium acetate (8.2 g, 84 mmol) and add them sequentially to a 500 mL three-necked flask. Add approximately 240 mL of anhydrous dioxane, purge with nitrogen three times, and then heat to 100 °C for 4 hours. After the starting materials have completely reacted, cool to room temperature, dilute with water, and extract with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:DCM = 10:1 (v / v) to obtain approximately 17.90 g of compounds 1-5, yield: 86.6%. MS: 737.93.
[0035] 4) Synthesis of compounds 1-7: Accurately weigh compounds 1-5 (7.4 g, 10 mmol), compounds 1-6 (4.8 g, 22 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and potassium carbonate (4.1 g, 30 mmol) and add them sequentially to a 500 mL three-necked flask. Add 100 mL of dioxane and 10 mL of water. After purging with nitrogen three times, raise the temperature to 90 °C and react for 4 hours. After the starting materials have completely reacted, cool to room temperature, dilute with water, and extract with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 10:1 (v / v) as the eluent to obtain approximately 6.36 g of compounds 1-7, yield: 83.4%. MS: 762.42.
[0036] 5) Synthesis of compounds 1-8: Accurately weigh compounds 1-7 (6.3 g, 8.3 mmol) and add them to a 250 mL three-necked flask. Add approximately 100 mL of anhydrous DMF, purge the mixture with nitrogen three times, and then add approximately 3 mL of phosphorus oxychloride. Heat the mixture to 90 °C and react for 4 hours. After the starting material has completely reacted, quench the reaction with water, extract with ethyl acetate, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 20:1 (v / v) as the eluent to obtain approximately 5.18 g of compounds 1-8, yield: 76.3%. MS: 818.04.
[0037] 6) Synthesis of compound (2): Accurately weigh compounds 1-8 (0.82 g, 1 mmol) and compounds 1-9 (0.92 g, 4 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of chloroform, purge with nitrogen three times, then add 5 mL of pyridine, and heat to 60 °C overnight. After the starting materials have completely reacted, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with PE:DCM = 1:1 (volume ratio) as the eluent to obtain approximately 681 mg of compound (2), yield: 54.8%. MS: 1242.17.
[0038] Example 2: This embodiment provides the synthesis of compound (5), as detailed below: (1) Reaction route diagram: .
[0039] (2) Specific synthesis steps: 1) Synthesis of compound 2-2: The synthesis of compound 2-2 was performed following the same procedure as that of compounds 1-7, except that compounds 1-6 were replaced with compounds 2-1 of equal molecular weight, yielding approximately 7.98 g of compound 2-2, with a yield of 85.7%. MS: 930.84.
[0040] 2) Synthesis of compounds 2-3: The synthesis of compounds 2-3 was performed following the same procedure as compounds 1-8, except that compounds 1-7 were replaced with compounds 2-2 of equal molecular weight, yielding approximately 7.12 g of compounds 2-3, yield: 86.9%. MS: 986.72.
[0041] 3) Synthesis of compound (5): The synthesis steps of compound (5) were the same as those for compound (2), except that compounds 1-8 were replaced with compounds 2-3 of equal molecular weight, yielding approximately 693 mg of compound (5), with a yield of 49.1%. MS: 1411.84. The mass spectrum is shown below. Figure 2 As shown.
[0042] Example 3: This embodiment provides the synthesis of compound (7), as detailed below: (1) Reaction route diagram: .
[0043] (2) Specific synthesis steps: The synthesis steps of compound (7) are the same as those of compound (2), except that compounds 1-8 are replaced with compounds 2-3 of equimolar molecular weight, and compounds 1-9 are replaced with compounds 3-1 of equimolar molecular weight, to obtain approximately 675 mg of compound (7), yield: 45.7%. MS: 1476.24.
[0044] Example 4: This embodiment provides the synthesis of compound (11), as detailed below: .
[0045] (2) Specific synthesis steps: 1) Synthesis of compound 11-2: The synthesis of compound 11-2 was similar to that of compound 1-4, except that compound 1-3 was replaced with equimolar amounts of 11-1, yielding approximately 17.22 g of compound 11-2, with a yield of 83.8%. MS: 587.32.
[0046] 2) Synthesis of compound 11-3: The synthesis of compound 11-3 was similar to that of compound 1-5, except that compound 1-4 was replaced with equimolar molecular weight 11-2, yielding approximately 13.73 g of compound 11-3, yield: 71.9%. MS: 681.65.
[0047] 3) Synthesis of compound 11-4: The synthesis of compound 11-4 was similar to that of compounds 1-7, except that compounds 1-5 were replaced with equimolar amounts of 11-3, and compounds 1-6 were replaced with equimolar amounts of 2-1, yielding approximately 7.78 g of compound 11-4. Yield: 89.0%. MS: 874.27.
[0048] 4) Synthesis of compound 11-5: The synthesis of compound 11-5 was similar to that of compounds 1-8, except that compounds 1-7 were replaced with equimolar amounts of 11-4, yielding approximately 5.67 g of compound 11-5, with a yield of 73.4%. MS: 930.38.
[0049] 5) Synthesis of compound (11): The synthesis steps of compound (11) are the same as those of compound (2), except that compounds 1-8 are replaced with compounds 11-5 of equal molecular weight, to obtain approximately 706 mg of compound (5), yield: 52.2%. MS: 1354.01.
[0050] Example 5: This embodiment provides the synthesis of compound (12), as detailed below: (1) Reaction route diagram: .
[0051] (2) Specific synthesis steps: The synthesis steps of compound (12) are the same as those of compound (2), except that compounds 1-8 are replaced with compounds 11-5 of equimolar molecular weight, and compounds 1-9 are replaced with compounds 3-1 of equimolar molecular weight, to obtain approximately 879 mg of compound (12), yield: 61.9%. MS: 1420.67.
[0052] Application example: This application example provides a device fabrication method, as shown below: The fabrication process of the organic solar cell (OSC) device including the above-mentioned compounds is described in detail below through specific embodiments. The device structure is as follows: Indium Tin Oxide (ITO) / PEDOT:PSS / Active Layer / PDINN / Ag The fabrication steps of device example 1 are as follows: Glass slides coated with strip-shaped ITO (anode) were sequentially ultrasonicated for 20 min each with glass cleaner, deionized water, acetone, isopropanol, and ethanol. After cleaning, the ITO conductive glass was dried and then treated with ozone for 20 min. Next, PEDOT:PSS (CLEVIOSTM PVP AI 4083) was spin-coated onto the surface of the ITO conductive glass at a speed of 3000 r / min for 40 seconds and dried at 150°C for 15 minutes to obtain the anode buffer layer. The annealed device was transferred to a glove box under a nitrogen atmosphere. In the glove box, the active layer material solution (the donor material was selected from polymer PM6, the acceptor material was selected from compound (2) obtained in Example 1, the mass ratio of polymer PM6 to compound (2) was 1:1.2, the solvent was chloroform, and the total concentration of the donor / acceptor material in chloroform was 15.4 mg / mL) was uniformly spin-coated. An active layer with a total thickness of 100 nm was obtained on the anode buffer layer. After hot annealing at 100 °C for 10 min, a PDINN solution (PDINN dissolved in methanol to prepare a solution with a concentration of 1.5 mg / mL) was spin-coated onto the active layer at a spin speed of 3000 rpm / min for 30 s to obtain the cathode buffer layer. Finally, a silver electrode with a thickness of 100 nm was deposited on the cathode buffer layer by vacuum evaporation, and the OSC device was finally obtained.
[0053] The fabrication steps of device example 2 are as follows: Glass slides coated with strip-shaped ITO (anode) were sequentially ultrasonicated for 20 min each with glass cleaner, deionized water, acetone, isopropanol, and ethanol. After cleaning, the ITO conductive glass was dried and treated with ozone for 20 min. Then, PEDOT:PSS (CLEVIOSTM PVP AI 4083) was spin-coated onto the surface of the ITO conductive glass at a speed of 3000 r / min for 40 seconds and dried at 150°C for 15 minutes to obtain the anode buffer layer. The annealed device was transferred to a glove box under a nitrogen atmosphere. In the glove box, the active layer material solution (the donor material was selected from polymer PM6, the acceptor material was selected from compound (5) obtained in Example 2, the mass ratio of polymer PM6 to compound (5) was 1:1.2, the solvent was chloroform, and the total concentration of donor / acceptor materials in chloroform was 15.4 mg / mL) was uniformly spin-coated. An active layer with a total thickness of 100 nm was obtained on the anode buffer layer. After hot annealing at 100 °C for 10 min, a PDINN solution (PDINN dissolved in methanol to prepare a solution with a concentration of 1.5 mg / mL) was spin-coated onto the active layer at a spin speed of 3000 rpm / min for 30 s to obtain the cathode buffer layer. Finally, a silver electrode with a thickness of 100 nm was deposited on the cathode buffer layer by vacuum evaporation, and the OSC device was finally obtained.
[0054] The fabrication steps for device Example 3 are as follows: Glass sheets coated with strip-shaped ITO (anode) were sequentially ultrasonicated for 20 minutes each with glass cleaner, deionized water, acetone, isopropanol, and ethanol. After cleaning, the ITO conductive glass was dried and treated with ozone for 20 minutes. Then, PEDOT:PSS (CLEVIOSTM PVP AI) was spin-coated onto the surface of the ITO conductive glass. 4083), with a rotation speed of 3000 r / min and a time of 40 seconds, was dried at 150°C for 15 minutes to obtain an anode buffer layer; the annealed device was transferred to a glove box under a nitrogen atmosphere, and the active layer material solvent (the donor material was selected from polymer PM6, the acceptor material was selected from compound (7) obtained in Example 3, the mass ratio of polymer PM6 to compound (7) was 1:1.2, the solvent was chloroform, and the total concentration of donor / acceptor materials in chloroform was 15.4 mg / mL) was uniformly spin-coated onto the anode buffer layer to obtain an active layer with a total thickness of 100 nm; then, after hot annealing on a hot stage at 100°C for 10 min, the cathode buffer layer material PDINN solution (PDINN was dissolved in methanol to prepare a solution with a concentration of 1.5 mg / mL) was spin-coated onto the active layer at a rotation speed of 3000 rpm / min and a time of 30 s to obtain a cathode buffer layer; finally, a 100 nm thick silver electrode was deposited on the cathode buffer layer by vacuum evaporation; finally, the OSC device was obtained.
[0055] The fabrication steps of device example 4 are as follows: Glass sheets coated with strip-shaped ITO (anode) were sequentially ultrasonicated for 20 minutes each with glass cleaner, deionized water, acetone, isopropanol, and ethanol. After cleaning, the ITO conductive glass was dried and treated with ozone for 20 minutes. Then, PEDOT:PSS (CLEVIOSTM PVP AI) was spin-coated onto the surface of the ITO conductive glass. 4083), with a rotation speed of 3000 r / min and a time of 40 seconds, was dried at 150℃ for 15 minutes to obtain an anode buffer layer; the annealed device was transferred to a glove box under a nitrogen atmosphere, and the active layer material solution (the donor material was selected from polymer PM6, the acceptor material was selected from compound (11), the mass ratio of polymer PM6 to compound (11) was 1:1.2, the solvent was chloroform, and the total concentration of the donor / acceptor material in chloroform was 15.4 mg / mL) was uniformly spin-coated onto the anode buffer layer to obtain an active layer with a total thickness of 100 nm; then, after hot annealing on a hot stage at 100℃ for 10 min, the cathode buffer layer material PDINN (PDINN was dissolved in methanol to prepare a solution with a concentration of 1.5 mg / mL) was spin-coated onto the active layer at a rotation speed of 3000 rpm / min and a time of 30 s to obtain a cathode buffer layer; finally, a silver electrode with a thickness of 100 nm was deposited on the cathode buffer layer by vacuum evaporation; finally, the OSC device was obtained.
[0056] The fabrication steps of device example 5 are as follows: Glass slides coated with strip-shaped ITO (anode) were sequentially ultrasonicated for 20 min each with glass cleaner, deionized water, acetone, isopropanol, and ethanol. After cleaning, the ITO conductive glass was dried and then treated with ozone for 20 min. Next, PEDOT:PSS (CLEVIOSTM PVP AI 4083) was spin-coated onto the surface of the ITO conductive glass at a speed of 3000 r / min for 40 seconds and dried at 150°C for 15 minutes to obtain the anode buffer layer. The annealed device was transferred to a glove box under a nitrogen atmosphere. In the glove box, the active layer material solution (the donor material was selected from polymer PM6, the acceptor material was selected from compound (12) obtained in Example 5, the mass ratio of polymer PM6 to compound (12) was 1:1.2, the solvent was chloroform, and the total concentration of donor / acceptor materials in chloroform was 15.4 mg / mL) was uniformly spun. An active layer with a total thickness of 100 nm was obtained by coating the anode buffer layer. After hot annealing at 100 °C for 10 min, a PDINN solution (PDINN dissolved in methanol to prepare a solution with a concentration of 1.5 mg / mL) was spin-coated onto the active layer at a spin speed of 3000 rpm / min for 30 s to obtain the cathode buffer layer. Finally, a silver electrode with a thickness of 100 nm was deposited on the cathode buffer layer by vacuum evaporation, thus obtaining the OSC device.
[0057] Performance testing The photoelectric conversion efficiency test results of the above-obtained organic solar cell devices under standard sunlight conditions are shown in Table 1: Table 1 As can be seen from Table 1, the combination of the small molecule acceptor material containing an eight-membered ring described in this application with the donor material PM6 achieved a photoelectric conversion efficiency of over 14.4%, and in particular, the device examples 2-3 achieved a photoelectric conversion efficiency of over 16.2%, demonstrating excellent photoelectric conversion performance.
[0058] The embodiments described above are merely preferred embodiments for fully illustrating the present invention, and the scope of protection of the present invention is not limited thereto. Equivalent substitutions or modifications made by those skilled in the art based on the present invention are all within the scope of protection of the present invention.
Claims
1. A small molecule receptor material containing an eight-membered ring, characterized in that, The structural formula is as follows: ； R1, R3, and R4 are independently selected from: -H, -D, C1~C20 straight-chain alkyl groups or C3~C20 branched-chain alkyl groups; R2 is independently selected from: -H, -D, -F, -Cl, -Br, or -I.
2. The small molecule acceptor material containing an eight-membered ring as described in claim 1, characterized in that, R1 is selected from straight-chain alkyl groups of C1 to C15, or branched alkyl groups of C3 to C15.
3. The small molecule acceptor material containing an eight-membered ring as described in claim 1, characterized in that, R1 is selected from or .
4. The small molecule acceptor material containing an eight-membered ring as described in claim 1, characterized in that, R3 and R4 are independently selected from: -H, -D, C1~C10 straight-chain alkyl or C3~C10 branched alkyl.
5. The small molecule acceptor material containing an eight-membered ring as described in claim 1, characterized in that, R3 and R4 can be selected independently from: -H, -D, -C4H9, -C6H13 or -C8H17.
6. The small molecule acceptor material containing an eight-membered ring as described in claim 1, characterized in that, R3 is selected from -H; R4 is selected from: -H, -D, -C4H9, -C6H13 or -C8H17.
7. The small molecule acceptor material containing an eight-membered ring as described in claim 1, characterized in that, Includes one or more of the following structures: ， ， ， ， ， ， 。 8. An organic solar cell device, characterized in that, The small molecule receptor material containing an eight-membered ring, as described in any one of claims 1 to 7.
9. The organic solar cell device as described in claim 8, characterized in that, The organic solar cell device comprises at least a cathode, an anode, and an active layer located between the cathode and the anode, wherein the acceptor material of the active layer comprises a small molecule acceptor material containing an eight-membered ring as described in any one of claims 1 to 7.
10. An organic solar cell device for automobiles, buildings, or the Internet of Things, characterized in that, Includes the organic solar cell device as described in claim 8 or 9.