Condensed ring-based non-fullerene electron acceptor material and preparation method and application thereof

Abstract

The invention discloses a non-fullerene electron acceptor material based on a condensed ring and a preparation method and application thereof, and aims to solve the problems that a non-fullerene electron acceptor molecular skeleton based on the condensed ring is difficult to construct and the photoelectric conversion efficiency is relatively low. The non-fullerene electron acceptor material is an eight-membered fused ring compound, and the chemical structural general formula of the non-fullerene electron acceptor material is as shown in a formula I: [formula I] # imgabs0 #. The electron acceptor material has an A-D-A type molecular skeleton, is easy to match the donor level and is beneficial to charge separation in a solar cell, and the photoelectric conversion efficiency can exceed 16.5%; and the compound is synthesized by a relatively simple synthesis method.

Description

Technical Field

[0001] The present invention relates to the technical field of organic solar cell, and more specifically to a condensed ring-based non-fullerene electron acceptor material and a preparation method and application thereof. Background Art

[0002] Since the development of non-fullerene acceptor materials, the photoelectric conversion efficiency (PCE) of organic solar cells processed based on them has achieved rapid growth. In just a few years, non-fullerene acceptor materials have been updated from the initial S or C type (such as ITIC, etc.) to the current "banana" type (Y6, etc.) based on condensed rings. The material configuration of S or C type is relatively easy to achieve, so a large number of different types of molecular skeletons have been developed based on their shapes, achieving a rapid increase in PCE; due to the specific shape of "banana" type materials, it is relatively difficult to change the molecular skeleton. At present, the alkyl chain is basically systematically regulated based on the molecular skeleton of Y6.

[0003] However, in order to achieve further breakthroughs in the PCE of organic solar cells, it is urgent to develop new non-fullerene acceptor materials different from Y6. For example, invention patent CN 112521404 A discloses a seven-membered fused ring compound, which, as an electron acceptor material for organic solar cells, enables the PCE of the cell to reach up to 15.7%. However, new non-fullerene electron acceptor materials need to be developed to further improve the PCE of organic solar cells to meet the needs of practical applications. Summary of the invention

[0004] In view of the difficulty in constructing a molecular skeleton of a non-fullerene electron acceptor based on a condensed ring, the present invention aims to develop a non-fullerene electron acceptor material based on a condensed ring and a preparation method thereof by introducing a new structural unit, and to apply the material to organic solar cells.

[0005] To achieve the above objectives, in a first aspect, the present invention provides a non-fullerene electron acceptor material based on a condensed ring, characterized in that: the non-fullerene electron acceptor material is an eight-membered condensed ring compound, and its chemical structure is shown in Formula I:

[0006]

[0007] In the above formula, X1 to X4 are the same or different and are selected from oxygen, sulfur, selenium, antimony, C1-C 30 Alkyl straight chain substituted nitrogen, C1~C 30 One of the nitrogen substituted by alkyl branch; R is selected from C1~C 30 Straight chain, C1~C 30 One of the following: a branched chain, a benzene ring substituted with different alkyl chains, and a thiophene ring substituted with different alkyl chains; R1 is selected from C1 to C30 Straight chain, C1~C 30 One of a branched chain, a benzene ring, a benzene ring substituted with different alkyl chains, a thiophene ring, and a thiophene ring substituted with different alkyl chains;

[0008] Ar is selected from one of the following structural units:

[0009]

[0010] Wherein, R2 to R5 are the same or different and are selected from H, F, Cl, CF3, C1 to C 20 Straight chain, C1~C 20 One of the branch chains.

[0011] Furthermore, the chemical structure of the non-fullerene electron acceptor material is as shown below:

[0012]

[0013] Furthermore, the chemical structure of the non-fullerene electron acceptor material is as shown below:

[0014]

[0015] Furthermore, the chemical structure of the non-fullerene electron acceptor material is as shown below:

[0016]

[0017] Furthermore, the chemical structure of the non-fullerene electron acceptor material is as shown below:

[0018]

[0019] In a second aspect, the present invention provides a method for preparing a condensed ring-based non-fullerene electron acceptor material, characterized in that it comprises the following steps:

[0020] Step S1: Under an inert gas environment, the compound represented by formula II reacts with diiodoethane to obtain a compound represented by formula III:

[0021] Wherein X1 and X2 are the same or different and are selected from oxygen, sulfur, selenium, antimony, C1-C 30 Alkyl straight chain substituted nitrogen, C1~C 30 One of the nitrogen substituted by the alkyl branch;

[0022] Step S2: Under an inert gas environment, the compound represented by formula IV reacts with an alkyltin chloride reagent to obtain a compound represented by formula V:

[0023] Wherein, X3 and X4 are the same or different and are selected from oxygen, sulfur, selenium, antimony, C1-C 30 Alkyl straight chain substituted nitrogen, C1~C 30 One of the nitrogen substituted by alkyl branch; R1 is selected from C1~C 30 Straight chain, C1~C 30 One of a branched chain, a benzene ring, a benzene ring substituted with different alkyl chains, a thiophene ring, and a thiophene ring substituted with different alkyl chains;

[0024] Step S3: Under an inert gas environment, the compound represented by formula III reacts with the compound represented by formula V to obtain the compound represented by formula VI:

[0025] Step S4: Under an inert gas environment, the compound represented by formula VI reacts with an alkylamine to obtain a compound represented by formula VII:

[0026] Wherein, R is selected from C1~C 30 Straight chain, C1~C 30 One of the following: a branched chain, a benzene ring substituted with different alkyl chains, and a thiophene ring substituted with different alkyl chains;

[0027] Step S5: Under an inert gas environment, the compound represented by formula VII reacts with phosphorus oxychloride and N,N-dimethylformamide to obtain a compound represented by formula VIII:

[0028] Step S6: reacting the compound represented by formula VIII with different indone to obtain the compound represented by formula I.

[0029] Further, in steps S1 to S5, the inert gas is nitrogen or argon;

[0030] And / or, in step S1, the reaction solvent is one or both of tetrahydrofuran and diethyl ether; the reaction temperature can be -80°C to 30°C; and the reaction time is 1 to 24 hours;

[0031] And / or, in step S2, the alkyl tin chloride is trimethyltin chloride or tributyltin chloride; the reaction solution is tetrahydrofuran; the reaction temperature can be -80°C to 30°C; the reaction time is 1 to 24 hours;

[0032] And / or, in step S3, the reaction is carried out in an organic solvent, the solvent is toluene; the reaction temperature can be -50°C to 130°C; the reaction time is 1 to 24 hours; the catalyst is a palladium catalyst; the base is tert-butoxide; the molar ratio of formula III to formula V is 1:2 to 1:10;

[0033] And / or, in step S4, the reaction solvent is 1,2-dichloroethane; the reaction temperature is 25°C to 100°C; and the reaction time is 1 to 18 hours;

[0034] And / or, in step S5, the reaction solvent is chloroform; the catalytic base is an organic base; the reaction temperature is 25° C. to 100° C.; and the reaction time is 1 to 24 hours.

[0035] Furthermore, in the steps S1 and S2, the mixture is first mixed and reacted at a temperature of -78°C and then returned to 25°C for further reaction for 2 hours; in the step S3, the reaction temperature is 110°C, the reaction time is 12 hours, the catalyst is one or two of tris(dibenzylideneacetone)dipalladium and tetrakistriphenylphosphine palladium, and the base is one or two of sodium tert-butoxide and potassium tert-butoxide; the molar ratio of formula III to formula V is 1:2.2; in the step S4, the reaction temperature is 78°C and the reaction time is 6 hours; in the step S5, the catalytic base is pyridine, the reaction temperature is 68°C and the reaction time is 12 hours.

[0036] In a third aspect, the present invention provides an application of a condensed ring-based non-fullerene electron acceptor material in an organic solar cell, characterized in that the organic solar cell comprises a negative electrode, an electron transport layer stacked above the negative electrode, an active layer stacked above the electron transport layer, a hole transport layer stacked above the active layer, and a positive electrode stacked above the hole transport layer; the active layer comprises the condensed ring-based non-fullerene electron acceptor material as described above.

[0037] In the last aspect, the present invention provides an application of a condensed ring-based non-fullerene electron acceptor material in an organic solar cell, characterized in that the organic solar cell comprises a negative electrode, a hole transport layer stacked above the negative electrode, an active layer stacked above the hole transport layer, an electron transport layer stacked above the active layer, and a positive electrode stacked above the electron transport layer; the active layer comprises the condensed ring-based non-fullerene electron acceptor material as described above.

[0038] Compared with the prior art, the above invention has the following advantages or beneficial effects:

[0039] (1) The present invention synthesizes an eight-membered fused ring compound by a relatively simple synthesis method, which can reduce the construction cost of fused ring-based non-fullerene electron acceptor materials;

[0040] (2) The electron acceptor material provided by the present invention has an ADA-type molecular skeleton, which is easy to match the donor energy level and is beneficial to charge separation in solar cells;

[0041] (3) The electron acceptor material provided by the present invention has excellent photoelectric conversion efficiency, which can exceed 16.5%. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] The present invention and its features and advantages will become more apparent upon reading the detailed description of non-limiting embodiments made with reference to the following accompanying drawings.

[0043] Figure 1 The UV-visible absorption spectra of the non-fullerene acceptor materials B-IN-1 and B-IN-3 in one embodiment of the present invention;

[0044] Figure 2 The cyclic voltammetry curve of the non-fullerene acceptor material B-IN-1 in one embodiment of the present invention;

[0045] Figure 3 1 is a cyclic voltammetry curve of the non-fullerene acceptor material B-IN-3 in one embodiment of the present invention. DETAILED DESCRIPTION

[0046] The technical solutions in the embodiments will be described clearly and completely below. Obviously, the embodiments described below are only part of the embodiments of the present invention, rather than all the embodiments.

[0047] The terms "comprise", "include" and any variations thereof in the following embodiments and comparative examples are intended to cover non-exclusive inclusions, for example, a process, method, or product comprising a series of steps or units is not limited to the listed steps or units, but may optionally include steps or units that are not listed, or may optionally include other steps or units that are inherent to these processes, methods, or products.

[0048] In addition, the experimental methods shown in the following examples are conventional methods unless otherwise specified; the materials and reagents are purchased from commercial sources unless otherwise specified.

[0049] Example 1: Preparation of B-IN-1

[0050]

[0051] Compound 1 was dissolved in chloroform, cooled to 0°C in an ice bath, and liquid bromine (6 eq.) was added dropwise. The mixture was returned to room temperature and reacted overnight. A saturated aqueous sodium thiosulfate solution was added to quench the reaction. The mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and the solvent was removed by vortexing. The crude product 2 was then dried to obtain the crude product 2, which was used directly in the next step. The yield was 95%. MS (MALDI-TOF): 455.6 [M] + .

[0052] Under nitrogen protection, compound 2 was dissolved in tetrahydrofuran, n-butyl lithium (2.2 eq.) was added dropwise at -78°C, reacted at -78°C for 1 hour, iodine was added, reacted at -78°C for 0.5 hour, returned to room temperature for 2 hours, saturated sodium thiosulfate aqueous solution was added to quench the reaction, extracted with dichloromethane, the solvent was removed by rotation, and compound 3 was separated and purified by column chromatography, with a yield of 84%. MS (MALDI-TOF): 549.8 [M] + .

[0053] Under nitrogen protection, compound 3 and TT-Br-Sn (2.2 eq.) were dissolved in tetrahydrofuran solution, and catalyst Pd(PPh3)4 (5% mol) was added. The reaction was refluxed at 90°C overnight. After the solvent was removed by vortexing, compound 4 was separated and purified by column chromatography. The yield was 47%. MS (MALDI-TOF): 1039.5 [M] + .

[0054] Under nitrogen protection, compound 4, sodium tert-butoxide (3 eq.), Pd2(dba)3 (1% mol), and dppf (4% mol) were dissolved in toluene solution, stirred at room temperature for 20 minutes, and then C24N (2.2 eq.) was added. The mixture was reacted overnight at 110°C under reflux. After the solvent was removed by vortexing, compound 5 was separated and purified by column chromatography with a yield of 32%. MS (MALDI-TOF): 974.2 [M] + .

[0055] Under nitrogen protection, compound 5 was dissolved in 1,2-dichloroethane, 10 eq. phosphorus oxychloride and 20 eq. NN-dimethylformamide were added, heated to 80°C, reacted overnight, cooled to room temperature, and after the solvent was removed by vortex, compound 6 was separated and purified by column chromatography, with a yield of 94%. MS (MALDI-TOF): 1030.6 [M] + .

[0056] Compound 6 and INCN-2F (6 eq.) were dissolved in chloroform, and a few drops of pyridine were added as a catalyst. The mixture was reacted under reflux for 12 hours, cooled to room temperature, and the solvent was removed by vortexing. Compound B-IN-1 was obtained by column chromatography separation and purification with a yield of 92%. MS (MALDI-TOF): 1454.2 [M] + .

[0057] Example 2: Preparation of B-IN-2

[0058]

[0059] Under nitrogen protection, compound 4, sodium tert-butoxide (3 eq.), Pd2(dba)3 (1% mol), and dppf (4% mol) were dissolved in toluene solution, stirred at room temperature for 20 minutes, and then C68N (2.2 eq.) was added. The mixture was reacted overnight at 110°C under reflux. After the solvent was removed by vortexing, compound 7 was separated and purified by column chromatography with a yield of 28%. MS (MALDI-TOF): 1198.5 [M] + .

[0060] Under nitrogen protection, compound 7 was dissolved in 1,2-dichloroethane, 10 eq. phosphorus oxychloride and 20 eq. NN-dimethylformamide were added, heated to 80°C, reacted overnight, cooled to room temperature, the solvent was removed by vortexing, and compound 8 was purified by column chromatography, with a yield of 94%. MS (MALDI-TOF): 1254.7 [M] + .

[0061] Compound 8 and INCN-2F (6 eq.) were dissolved in chloroform, and a few drops of pyridine were added as a catalyst. The mixture was reacted under reflux for 12 hours, cooled to room temperature, and the solvent was removed by vortexing. Compound B-IN-2 was obtained by column chromatography separation and purification with a yield of 89%. MS (MALDI-TOF): 1679.4 [M] + .

[0062] Example 3: Preparation of B-IN-3

[0063]

[0064] Compound 6 and INCN-2Cl (6 eq.) were dissolved in chloroform, and a few drops of pyridine were added as a catalyst. The mixture was reacted under reflux for 12 hours, cooled to room temperature, and the solvent was removed by vortexing. Compound B-IN-3 was obtained by column chromatography separation and purification with a yield of 82%. MS (MALDI-TOF): 1520.3 [M] + .

[0065] Example 4: Preparation of B-IN-4

[0066]

[0067] Under nitrogen protection, compound 3 and TSe-Br-Sn (2.2 eq.) were dissolved in tetrahydrofuran solution, and catalyst Pd(PPh3)4 (5% mol) was added. The reaction was refluxed at 90°C overnight. After the solvent was removed by vortexing, compound 9 was separated and purified by column chromatography. The yield was 44%. MS (MALDI-TOF): 1135.6 [M] + .

[0068] Under nitrogen protection, compound 9, sodium tert-butoxide (3 eq.), Pd2(dba)3 (1% mol), and dppf (4% mol) were dissolved in toluene solution, stirred at room temperature for 20 minutes, and then C24N (2.2 eq.) was added. The mixture was reacted overnight at 110°C under reflux. After the solvent was removed by vortexing, compound 10 was separated and purified by column chromatography with a yield of 44%. MS (MALDI-TOF): 1070.2 [M] + .

[0069] Under nitrogen protection, compound 10 was dissolved in 1,2-dichloroethane, 10 eq. phosphorus oxychloride and 20 eq. NN-dimethylformamide were added, heated to 80°C, reacted overnight, cooled to room temperature, the solvent was removed by vortex, and compound 11 was purified by column chromatography with a yield of 96%. MS (MALDI-TOF): 1126.5 [M] + .

[0070] Compound 11 and INCN-2F (6 eq.) were dissolved in chloroform, and a few drops of pyridine were added as a catalyst. The mixture was reacted under reflux for 12 hours, cooled to room temperature, and the solvent was removed by vortexing. Compound B-IN-4 was obtained by column chromatography separation and purification with a yield of 85%. MS (MALDI-TOF): 1550.6 [M] + .

[0071] The absorbance spectrum of the receptor material B-IN-1 obtained in Example 1 and the receptor material B-IN-3 obtained in Example 3 was measured. B-IN-1 and B-IN-3 were dissolved in chloroform respectively, and the compounds were evenly thrown on a quartz sheet by a film-throwing method. The absorption spectra of the B-IN-1 and B-IN-3 compounds are shown in Figure 1 .

[0072] The energy levels of the receptor composite materials B-IN-1 and B-IN-3 were measured by electrochemical cyclic voltammetry. B-IN-1 and B-IN-3 were dissolved in chloroform and filmed on the working electrode by drop film method. 180 mg of Bu4NP6 was dissolved in 5 mL of acetonitrile as the electrolyte, and the HOMO and LUMO energy levels were measured by electrochemical cyclic voltammetry. The cyclic voltammetry data of B-IN-1 and B-IN-3 compounds are shown in Figure 2 and Figure 3 The HOMO energy level of compound B-IN-1 is -5.65 eV, and the LUMO is -3.87 eV; the HOMO energy level of compound B-IN-3 is -5.68 eV, and the LUMO is -3.88 eV.

[0073] Application Example 1: Preparation of organic solar cells

[0074] The organic solar cell includes a negative electrode, an electron transport layer stacked on the negative electrode, an active layer stacked on the electron transport layer, a hole transport layer stacked on the active layer, and a positive electrode stacked on the hole transport layer; the active layer contains the condensed ring-based non-fullerene electron acceptor material as described above.

[0075] Specifically, a conductive polymer (styrene sulfonate) doped poly (3,4-ethylenedioxythiophene) (PEDOT:PSS) is used as the hole transport layer and is thrown onto the indium tin oxide (ITO) positive electrode interface at a rotation speed of 3000 for 30 seconds, and then baked at 150°C for 10 minutes, and transferred to a glove box filled with nitrogen. B-IN-1 and B-IN-3 prepared in Examples 1 and 3 are respectively mixed with the polymer donor PM6 and dissolved in chloroform, and stirred to dissolve. The prepared solution is thrown onto the ITO sheet at different rotation speeds, thermally annealed at 100°C to obtain the active layer, and then the PDINN layer is modified as the electron transport layer, and finally a silver electrode is evaporated on it as the negative electrode to obtain an organic solar cell. The AM1.5G intensity (100mW / cm 2 ) were used to measure the open circuit voltage, short circuit current and fill factor of the prepared solar cell.

[0076] Based on B-IN-1 of Example 1, an organic solar cell was manufactured and performance tested according to the procedure of the application example. oc =0.845V, short circuit current J sc =24.81mA / cm 2 , filling factor FF = 75.16%, conversion efficiency PCE = 15.76%.

[0077] Based on B-IN-3 of Example 3, an organic solar cell was manufactured and performance tested according to the procedure of the application example. oc =0.861V, short circuit current J sc =25.36mA / cm 2 , filling factor FF = 75.66%, conversion efficiency PCE = 16.52%.

[0078] Application Example 2: Preparation of organic solar cells

[0079] The preparation method of the organic solar cell is similar to that of Application Example 1, but different from Application Example 1 in that the organic solar cell includes a negative electrode, a hole transport layer stacked on the negative electrode, an active layer stacked on the hole transport layer, an electron transport layer stacked on the active layer, and a positive electrode stacked on the electron transport layer; the active layer includes the condensed ring-based non-fullerene electron acceptor material as described above.

[0080] From the test results of the above embodiments and application examples, it can be seen that the present invention synthesizes an eight-membered fused ring compound through a relatively simple synthesis method, which can reduce the construction cost of non-fullerene electron acceptor materials based on fused rings; it has an ADA-type molecular skeleton, which is easy to match the donor energy level, is beneficial to charge separation in solar cells, and has excellent photoelectric conversion efficiency.

[0081] Those skilled in the art should understand that those skilled in the art can implement variations by combining the prior art and the above embodiments, which will not be described in detail here. Such variations do not affect the essential content of the present invention, and will not be described in detail here.

[0082] The above describes the preferred embodiments of the present invention. It should be understood that the present invention is not limited to the above-mentioned specific embodiments, and the devices and structures that are not described in detail should be understood to be implemented in a common manner in the art; any technician familiar with the art can use the above-disclosed methods and technical contents to make many possible changes and modifications to the technical solutions of the present invention without departing from the scope of the technical solutions of the present invention, or modify them into equivalent embodiments of equivalent changes, which does not affect the essential content of the present invention. Therefore, any simple modifications, equivalent changes and modifications made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solutions of the present invention are still within the scope of protection of the technical solutions of the present invention.

Claims

1. A non-fullerene electron acceptor material based on condensed rings, characterized in that: The non-fullerene electron acceptor material is an eight-membered fused ring compound, and its chemical structure is shown in Formula I: In the above formula, X1 to X4 are the same or different and are selected from oxygen, sulfur, selenium, antimony, C1-C 30 Alkyl straight chain substituted nitrogen, C1~C 30 One of the nitrogen substituted by alkyl branch; R is selected from C1~C 30 Straight chain, C1~C 30 One of the following: a branched chain, a benzene ring substituted with different alkyl chains, and a thiophene ring substituted with different alkyl chains; R1 is selected from C1 to C 30 Straight chain, C1~C 30 One of a branched chain, a benzene ring, a benzene ring substituted with different alkyl chains, a thiophene ring, and a thiophene ring substituted with different alkyl chains; Ar is selected from one of the following structural units: Wherein, R2 to R5 are the same or different and are selected from H, F, Cl, CF3, C1 to C 20 Straight chain, C1~C 20 One of the branch chains.

2. A condensed ring-based non-fullerene electron acceptor material according to claim 1, characterized in that: The chemical structural formula of the non-fullerene electron acceptor material is shown below:

3. A condensed ring-based non-fullerene electron acceptor material according to claim 1, characterized in that: The chemical structural formula of the non-fullerene electron acceptor material is shown below:

4. The condensed ring-based non-fullerene electron acceptor material according to claim 1, characterized in that: The chemical structural formula of the non-fullerene electron acceptor material is shown below:

5. The condensed ring-based non-fullerene electron acceptor material according to claim 1, characterized in that: The chemical structural formula of the non-fullerene electron acceptor material is shown below:

6. A method for preparing a condensed ring-based non-fullerene electron acceptor material, characterized in that: The following steps are involved: Step S1: Under an inert gas environment, the compound represented by formula II reacts with diiodoethane to obtain a compound represented by formula III: [Formula II] [Formula III] Wherein X1 and X2 are the same or different and are selected from oxygen, sulfur, selenium, antimony, C1-C 30 Alkyl straight chain substituted nitrogen, C1~C 30 One of the nitrogen substituted by the alkyl branch; Step S2: Under an inert gas environment, the compound represented by Formula IV reacts with an alkyltin chloride reagent to obtain a compound represented by Formula V: [Formula IV] [Formula V] Wherein, X3 and X4 are the same or different and are selected from oxygen, sulfur, selenium, antimony, C1-C 30 Alkyl straight chain substituted nitrogen, C1~C 30 One of the nitrogen substituted by alkyl branch; R1 is selected from C1~C 30 Straight chain, C1~C 30 One of a branched chain, a benzene ring, a benzene ring substituted with different alkyl chains, a thiophene ring, and a thiophene ring substituted with different alkyl chains; Step S3: Under an inert gas environment, the compound represented by formula III reacts with the compound represented by formula V to obtain the compound represented by formula VI: [Formula VI] Step S4: Under an inert gas environment, the compound represented by Formula VI reacts with an alkylamine to obtain a compound represented by Formula VII: [Formula VII] Wherein, R is selected from C1~C 30 Straight chain, C1~C 30 One of the following: a branched chain, a benzene ring substituted with different alkyl chains, and a thiophene ring substituted with different alkyl chains; Step S5: Under an inert gas environment, the compound represented by Formula VII reacts with phosphorus oxychloride and N,N-dimethylformamide to obtain a compound represented by Formula VIII: [Formula VIII] Step S6: reacting the compound represented by formula VIII with different indone to obtain the compound represented by formula I.

7. The method for preparing a condensed ring-based non-fullerene electron acceptor material according to claim 6, characterized in that: In the steps S1 to S5, the inert gas is nitrogen or argon; And / or, in step S1, the reaction solvent is one or both of tetrahydrofuran and diethyl ether; the reaction temperature can be -80°C to 30°C; and the reaction time is 1 to 24 hours; And / or, in step S2, the alkyl tin chloride is trimethyltin chloride or tributyltin chloride; the reaction solution is tetrahydrofuran; the reaction temperature can be -80°C to 30°C; the reaction time is 1 to 24 hours; And / or, in step S3, the reaction is carried out in an organic solvent, the solvent is toluene; the reaction temperature can be -50°C to 130°C; the reaction time is 1 to 24 hours; the catalyst is a palladium catalyst; the base is tert-butoxide; the molar ratio of formula III to formula V is 1:2 to 1:10; And / or, in step S4, the reaction solvent is 1,2-dichloroethane; the reaction temperature is 25°C to 100°C; and the reaction time is 1 to 18 hours; And / or, in step S5, the reaction solvent is chloroform; the catalytic base is an organic base; the reaction temperature is 25° C. to 100° C.; and the reaction time is 1 to 24 hours.

8. The method for preparing a condensed ring-based non-fullerene electron acceptor material according to claim 7, characterized in that: In the steps S1 and S2, the reaction is first carried out at a temperature of -78°C and then returned to 25°C for further reaction for 2 hours; in the step S3, the reaction temperature is 110°C, the reaction time is 12 hours, the catalyst is one or two of tris(dibenzylideneacetone)dipalladium and tetrakistriphenylphosphine palladium, and the base is one or two of sodium tert-butoxide and potassium tert-butoxide; the molar ratio of formula III to formula V is 1:2.2; in the step S4, the reaction temperature is 78°C and the reaction time is 6 hours; in the step S5, the catalytic base is pyridine, the reaction temperature is 68°C and the reaction time is 12 hours.

9. Application of condensed ring-based non-fullerene electron acceptor materials in organic solar cells, characterized in that: The organic solar cell comprises a negative electrode, an electron transport layer stacked above the negative electrode, an active layer stacked above the electron transport layer, a hole transport layer stacked above the active layer, and a positive electrode stacked above the hole transport layer; the active layer comprises the condensed ring-based non-fullerene electron acceptor material as described in any one of claims 1 to 5.

10. Application of condensed ring-based non-fullerene electron acceptor materials in organic solar cells, characterized in that: The organic solar cell comprises a negative electrode, a hole transport layer stacked on the negative electrode, an active layer stacked on the hole transport layer, an electron transport layer stacked on the active layer, and a positive electrode stacked on the electron transport layer; the active layer comprises the condensed ring-based non-fullerene electron acceptor material as described in any one of claims 1 to 5.

Images