A five-membered ring-containing organic compound and use thereof in organic electronic devices

Abstract

The present application relates to a kind of organic compounds containing five-membered ring and its application in organic electronic device.The organic compounds containing five-membered ring according to the present application can be applied as donor material in the photoactive layer of organic solar cell, and matched with suitable acceptor material, so as to improve the photoelectric performance of device.

Description

Technical Field

[0001] This invention relates to the field of organic solar cell materials, and in particular to a five-membered fused-ring organic compound and its application in organic electronic devices. Background Technology

[0002] With the continuous depletion of fossil fuels, human society faces an increasingly severe energy crisis and the resulting environmental pressures, such as climate change and environmental pollution. Developing green and renewable energy technologies has always been a key research focus for scientists worldwide. In the field of solar cell technology, organic solar cells possess advantages such as low cost, high efficiency, flexibility, colored semi-transparent properties, and the ability to be fabricated over large areas using low-temperature solution printing. They are currently an ideal photoelectric conversion technology applicable to wearable electronic devices, IoT devices, and building-integrated photovoltaics (BIPV).

[0003] Currently, the photoactive layer of high-efficiency organic solar cells consists of polymer donors and small-molecule non-fullerene acceptors. However, the intrinsic molecular weight polydispersity of polymers leads to batch-to-batch variability, resulting in differences in photoelectric conversion efficiency (PCE), which is detrimental to future large-scale production. Compared to polymers, small-molecule materials offer advantages such as tunable energy levels, simple synthesis, low processing costs, and easy purification. Consequently, small-molecule organic solar cells have attracted increasing attention in recent years.

[0004] Currently, most small molecule donor materials are based on BDT. While existing small-molecule donor materials have a good structure, their photoelectric conversion efficiency is limited when applied to organic solar cells due to the difficulty in controlling the morphology of the donor and acceptor materials in the photoactive layer. For example, Chinese patent CN112047956A discloses a small-molecule donor material CN-1 based on a BDT structure, but when mixed with Y6 to prepare a photoactive layer for use in organic solar cell devices, the photoelectric conversion efficiency is only 4.25%. Therefore, developing novel small-molecule donor materials is an important way to improve the photovoltaic conversion efficiency of small-molecule batteries. Summary of the Invention

[0005] The purpose of this invention is to provide a novel five-membered fused-ring organic compound, which exhibits better photoelectric conversion efficiency when used as an organic small molecule donor material in organic solar cells.

[0006] To achieve the objectives of this invention, the following technical solution is provided:

[0007] A five-membered fused-ring organic compound having the structure shown in general formula (I):

[0008]

[0009] in:

[0010] R1, R2, R4, and R5, each time appearing independently, are selected from -H (hydrogen), -D (deuterium), straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, straight-chain alkylthio groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic alkylthio groups having 3 to 20 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, or groups formed by combinations of the above groups;

[0011] Each time R3 appears, it is independently selected from a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic alkylthio group having 3 to 20 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups;

[0012] Each time R6 appears, it is independently selected from straight-chain alkyl groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms.

[0013] The present invention also provides a mixture comprising the above-mentioned five-membered fused-ring organic compound and at least one organic functional material, wherein the organic functional material is selected from photoactive layer acceptor materials or photoactive layer donor materials.

[0014] The present invention further provides a composition comprising the above-mentioned five-membered fused-ring organic compound or mixture, and at least one organic solvent.

[0015] The present invention further provides an organic electronic device comprising at least one five-membered fused-ring organic compound or mixture as described above.

[0016] Compared with the prior art, the beneficial effects of the present invention include:

[0017] (1) Five-membered fused ring donor unit It has a large conjugated plane and improves the planarity of the molecule, while also exhibiting excellent charge transport properties;

[0018] (2) The electron-withdrawing end group is selected from cyano ester units. Cyano ester end groups have good solubility and can regulate the stacking and arrangement of molecules to form a more suitable interpenetrating network structure with the acceptor, which is conducive to the dissociation of excitons and charge transport, resulting in more efficient photovoltaic performance.

[0019] (3) The connecting unit contains two thiophenes. Compared with the existing three-thiophene system, the molecule has better rigidity, thereby achieving optimization of molecular structure and active layer morphology;

[0020] (4) A cyano group is introduced into the connecting unit. As a strong electron-withdrawing group, the cyano group has functions such as inducing molecular aggregation and promoting crystallization, and plays a significant role in regulating the morphology of the active layer of photovoltaic devices. At the same time, the introduction of the cyano group can achieve a lower HOMO energy level, which can lead to an increase in the open-circuit voltage of the device, thereby improving the photoelectric conversion efficiency of the device. More importantly, compared with the reaction of introducing electron-withdrawing groups such as fluorine, the synthesis of cyano-substituted thiophene is easier and has more commercial application prospects.

[0021] (5) The compound is simple to synthesize, easy to purify, and the raw materials are inexpensive, making it suitable for large-scale preparation and production. Attached Figure Description

[0022] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0023] Figure 1 These are schematic diagrams of the device embodiments 1-5 and the device comparative embodiment 1 of the present invention. Detailed Implementation

[0024] This application provides a five-membered fused-ring organic compound, mixtures, compositions, and their application in organic electronic devices. To make the objectives, technical solutions, and effects of this application clearer and more explicit, the following provides a further detailed description. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the scope of this application.

[0025] In this invention, organic photovoltaic devices, organic solar cells, OPV, and OSC have the same meaning and can be used interchangeably.

[0026] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl groups. The number of carbon atoms in a straight-chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the number of carbon atoms in a branched alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6; and the number of carbon atoms in a cyclic alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Non-limiting examples of straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and -C. 10 H 21 -C 11 H23 -C 12 H 25 -C 13 H 27 -C 14 H 29 -C 15 H 31 -C 16 H 33 Non-limiting examples of branched alkyl groups include: isopropyl, branched alkyl groups containing 4 carbon atoms, branched alkyl groups containing 5 carbon atoms, branched alkyl groups containing 6 carbon atoms, branched alkyl groups containing 7 carbon atoms, branched alkyl groups containing 8 carbon atoms, branched alkyl groups containing 9 carbon atoms, branched alkyl groups containing 10 carbon atoms, branched alkyl groups containing 11 carbon atoms, branched alkyl groups containing 12 carbon atoms, branched alkyl groups containing 13 carbon atoms, branched alkyl groups containing 14 carbon atoms, and branched alkyl groups containing 15 carbon atoms. Branched alkyl groups containing 16 carbon atoms; non-limiting examples of cyclic alkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, branched alkyl groups containing 7 carbon atoms, branched alkyl groups containing 8 carbon atoms, branched alkyl groups containing 9 carbon atoms, branched alkyl groups containing 10 carbon atoms, branched alkyl groups containing 11 carbon atoms, branched alkyl groups containing 12 carbon atoms, branched alkyl groups containing 13 carbon atoms, branched alkyl groups containing 14 carbon atoms, branched alkyl groups containing 15 carbon atoms, and branched alkyl groups containing 16 carbon atoms.

[0027] The term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above connected to other groups via an oxygen atom. The number of carbon atoms in a straight-chain alkoxy group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the number of carbon atoms in a branched-chain alkoxy group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6; and the number of carbon atoms in a cyclic alkoxy group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0028] The term "alkathio" refers to a group with the structure "-S-alkyl", that is, an alkyl group as defined above connected to other groups via a sulfur atom. The number of carbon atoms in a straight-chain alkathio group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the number of carbon atoms in a branched-chain alkathio group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6; and the number of carbon atoms in a cyclic alkathio group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Suitable examples of phrases containing this term include, but are not limited to: methylthio (-S-CH3 or -SMe), ethylthio (-S-CH2CH3 or -SEt), and tert-butylthio (-SC(CH3)3 or -StBu).

[0029] In this invention, the "*" connected to a single key indicates a connection.

[0030] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if general formula I contains multiple R1, R2, R3, R4, R5, and R6, then multiple R1 can be independently selected from the same or different groups, multiple R2 can be independently selected from the same or different groups, multiple R3 can be independently selected from the same or different groups, multiple R4 can be independently selected from the same or different groups, multiple R5 can be independently selected from the same or different groups, and multiple R6 can be independently selected from the same or different groups.

[0031] In this invention, the terms "combinations thereof," "any combination thereof," "any combination thereof," and "combination" refer to all suitable combinations of any two, three, four, or more groups listed.

[0032] In this invention, terms such as "further," "even more," and "particularly" are used for descriptive purposes and to indicate differences in content, but should not be construed as limiting the scope of protection of this invention.

[0033] In this invention, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without." If multiple "options" appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "option" is independent.

[0034] This invention relates to a five-membered fused-ring organic compound having a structure as shown in general formula (I):

[0035]

[0036] in:

[0037] R1, R2, R4, and R5, each time appearing independently, are selected from -H (hydrogen), -D (deuterium), straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, straight-chain alkylthio groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic alkylthio groups having 3 to 20 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, or groups formed by combinations of the above groups;

[0038] Each time R3 appears, it is independently selected from a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a branched or cyclic alkoxy group having 3 to 20 carbon atoms, a branched or cyclic alkylthio group having 3 to 20 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups;

[0039] Each time R6 appears, it is independently selected from straight-chain alkyl groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms.

[0040] In one embodiment, each occurrence of R1 and R2 is independently selected from -H, -D, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, cyano, nitro, -Cl, -Br, -F, -I, or groups formed by combinations of the above groups.

[0041] In one embodiment, each occurrence of R1 is independently selected from -H, -D, cyano, nitro, -Cl, -Br, -F, -I, or CF3.

[0042] In one specific embodiment, R1 is independently selected from -H or -F each time it appears.

[0043] In one embodiment, each occurrence of R2 is independently selected from -H, -D, straight-chain alkyl groups having 1 to 8 C atoms, cyano, nitro, -Cl, -Br, -F, -I, or CF3.

[0044] In one specific embodiment, each occurrence of R2 is independently selected from -H and -C6H. 13 -F, -Cl, or cyano.

[0045] In one embodiment, each occurrence of R3 is independently selected from a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, or a branched-chain alkylthio group having 3 to 20 carbon atoms.

[0046] Furthermore, in one embodiment, each occurrence of R3 is independently selected from a straight-chain alkyl group having 1 to 16 carbon atoms, a straight-chain alkoxy group having 1 to 16 carbon atoms, a straight-chain alkylthio group having 1 to 16 carbon atoms, a branched-chain alkyl group having 3 to 16 carbon atoms, a branched-chain alkoxy group having 3 to 16 carbon atoms, or a branched-chain alkylthio group having 3 to 16 carbon atoms.

[0047] In one specific embodiment, R3 is independently selected each time it appears.

[0048] Wherein: * indicates a connection site. In one embodiment, Each occurrence is selected from any of the following groups, either identically or differently:

[0049]

[0050] Where: * indicates a connection site.

[0051] In one embodiment, R4 and R5 are each selected independently from -H, -D, straight-chain alkyl having 1 to 20 carbon atoms, straight-chain alkoxy having 1 to 20 carbon atoms, straight-chain alkylthio having 1 to 20 carbon atoms, branched or cyclic alkyl having 3 to 20 carbon atoms, branched or cyclic alkoxy having 3 to 20 carbon atoms, and branched or cyclic alkylthio having 3 to 20 carbon atoms.

[0052] In one embodiment, each occurrence of R4 is independently selected from -H, -D, straight-chain alkyl groups having 1 to 10 C atoms, or branched alkyl groups having 3 to 10 C atoms.

[0053] In a more specific embodiment, each occurrence of R4 is independently selected from -H, -D, and -C6H. 13 -C8H 17 ,

[0054] In one embodiment, each occurrence of R5 is independently selected from -H, -D, straight-chain alkyl groups having 1 to 10 C atoms, or branched or cyclic alkyl groups having 3 to 10 C atoms.

[0055] In a more specific embodiment, each occurrence of R5 is independently selected from -H, -D, and -C6H. 13 -C8H 17 ,

[0056] Preferably, R4 and R5 are selected from the same or different functional groups each time they appear. More preferably, Each time it appears, selected from Specifically, selected from any of the following groups:

[0057]

[0058] In one embodiment, each occurrence of R6 is independently selected from straight-chain alkyl groups having 1 to 10 carbon atoms or branched alkyl groups having 3 to 10 carbon atoms.

[0059] In one embodiment, Selected from

[0060] The five-membered fused-ring organic compound provided according to the present invention is selected from any of the following structural formulas, but is not limited thereto:

[0061]

[0062]

[0063]

[0064] The present invention further relates to a mixture comprising at least one of the above-mentioned five-membered fused-ring organic compounds and at least one other organic functional material, wherein the at least one other organic functional material is selected from photoactive layer acceptor materials and / or photoactive layer donor materials.

[0065] Preferably, the other organic functional material is selected from active layer receptor materials, and the receptor material is selected from one, two or more of the following structural formulas, but is not limited thereto.

[0066]

[0067]

[0068] In one embodiment, the other organic functional material is selected from the active layer donor material, and the active layer of the donor material is selected from structures such as PM6, PM7, PBDB-T, PTQ10, PT2, T1, PB2, etc., but is not limited thereto.

[0069] In one embodiment, the mass ratio of donor material to acceptor material is 1:1 to 1:1.2.

[0070] The present invention further relates to a photoactive layer donor material, wherein the photoactive layer donor material is selected from at least one five-membered fused-ring organic compound as provided in the present invention.

[0071] The present invention also relates to a composition comprising at least one of the five-membered fused-ring organic compounds or mixtures as described above, and at least one organic solvent. The organic solvent is selected from aliphatic hydrocarbons, chlorinated hydrocarbons, aromatic hydrocarbons, ketones, ethers, and mixtures thereof.

[0072] Preferably, the organic solvent is selected from dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, 2,4-dimethylanisole, 1-methylnaphthalene, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, N,N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, 1,5-dimethyltetrahydrofuran, acetophenone, acetophenone, tetrahydronaphthalene, 2-methylthiophene, 3-methylthiophene, decahydronaphthalene, indene, methyl benzoate, ethyl benzoate, mesitylene, or a mixture of any two or more of the above organic solvents.

[0073] In a more preferred embodiment, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.

[0074] This invention further relates to the application of a five-membered fused-ring organic compound as described above in organic electronic devices. The organic electronic devices may be, but are not limited to, organic solar cells (OPVs), organic light-emitting diodes (OLEDs), and organic photodetectors (OPDs).

[0075] The present invention also provides an organic electronic device comprising the five-membered fused-ring organic compound or mixture described above.

[0076] Preferably, the organic electronic device comprises at least a first electrode, a second electrode, and a photoactive layer located between the first and second electrodes. The photoactive layer material comprises at least a five-membered fused-ring organic compound or mixture as described above. Preferably, the organic electronic device is selected from organic solar cells.

[0077] In one embodiment, the first electrode is a cathode and the second electrode is an anode; in another embodiment, the first electrode is an anode and the second electrode is a cathode.

[0078] In one embodiment, the organic electronic device of the present invention further includes a substrate located on the bottom side of the first electrode. Preferably, the substrate is selected from a glass substrate, a thin-film glass substrate, or a transparent plastic substrate. The plastic substrate may include, but is not limited to, films in the form of single or multiple layers, such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), and polyimide (PI), and may also use substrates commonly used in organic solar cells.

[0079] Preferably, the organic solar cell according to the present invention comprises a cathode, an anode, a photoactive layer located between the cathode and the anode, an anode buffer layer located between the anode and the photoactive layer, and a cathode buffer layer located between the cathode and the photoactive layer. The photoactive layer material comprises at least one or more of the five-membered fused-ring organic compounds or mixtures described above. Preferably, the photoactive layer material comprises a donor material and an acceptor material, wherein the donor material is selected from at least one of the five-membered fused-ring organic compounds described above, and the acceptor material is selected from one, two, or more of compounds (A-1)-(A-32). In one embodiment, the mass ratio of the donor material to the acceptor material is selected from 1:1 to 1:1.2.

[0080] In one embodiment, the anode buffer layer material is selected from PEDOT:PSS or MoO3, but is not limited thereto.

[0081] In one embodiment, the cathode buffer layer material is selected from PFN-Br, PDINN, PEI-Zn, ZnO, etc., but is not limited thereto.

[0082] There are no particular limitations on the preparation methods of each thin film in the organic electronic device described in this invention. Vacuum evaporation, sputtering, spin coating, dip coating, doctor blade coating, slot coating, inkjet printing, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0083] The organic solar cells provided by this invention can be used in various devices, such as wearable electronic devices, smart IoT, smart homes, smart agriculture, building photovoltaics, new energy vehicles, and new power systems based on new energy sources.

[0084] The present invention will now be described in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the inventive concept, those skilled in the art should realize that any changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0085] Compound preparation:

[0086] Example 1: Synthesis of compound (2)

[0087]

[0088]

[0089] Synthesis of compound 2-2:

[0090] Accurately weigh compound 2-1 (24.7 g, 100 mmol), 2-bromo-3-cyanothiophene (18.8 g, 100 mmol), and tetraphenylphosphine palladium (1.1 g, 1 mmol) into a 1000 mL three-necked flask. Add 400 mL of anhydrous toluene, purge with argon three times, and then heat to 80 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel chromatography with PE as the eluent to give approximately 15.8 g of compound 2-2, yield: 82.6%. MS: 191.72

[0091] Synthesis of compounds 2-3:

[0092] Accurately weigh 15.3 g (80 mmol) of compound 2-2 into a 500 mL three-necked flask, add approximately 200 mL of anhydrous THF, purge the mixture three times with nitrogen, and then cool to -80 °C. Slowly add 40 mL (2 M) of LDA to the reaction system. After the addition is complete, maintain the low temperature and react for one hour. Then, slowly add 15.9 g (80 mmol) of trimethyltin chloride to the reaction system. Allow the mixture to warm naturally to room temperature and react for 4 hours. Quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Recrystallize the crude product from methanol to give approximately 22.3 g of compound 2-3, yield: 78.7%. MS: 354.11

[0093] Synthesis of compounds 2-6:

[0094] Accurately weigh compounds 2-4 (4.85 g, 10 mmol), 2-5 (7.54 g, 20 mmol), and tetraphenylphosphine palladium (0.46 g, 0.4 mmol) into a 250 mL three-necked flask. Add 100 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel chromatography with a stirred column. Eluent is PE:DCM = 3:1 (v / v). Approximately 5.4 g of compound 2-6 was obtained, yield: 72%. MS: 752.03.

[0095] Synthesis of compounds 2-7:

[0096] Accurately weigh compounds 2-6 (3.76 g, 5 mmol), 2-3 (3.54 g, 10 mmol), and tetraphenylphosphine palladium (0.23 g, 0.2 mmol) into a 100 mL three-necked flask. Add 50 mL of anhydrous toluene, purge with argon three times, and then heat to 110 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:EA eluent ratio of 4:1 (v / v). This yields approximately 3.5 g of compound 2-7, 65% yield. MS: 1061.31.

[0097] Synthesis of compounds 2-8:

[0098] Accurately weigh 3.18 g (3 mmol) of compound 2-7 and add it to a 100 mL three-necked flask. Add 20 mL of anhydrous DMF, purge with argon three times, and then cool to 0 °C in an ice-salt bath. Weigh 2.75 g (18 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 1 h. Then, raise the temperature to 80 °C and react for 12 h. Cool to room temperature, quench the reaction solution in water, and extract three times with dichloromethane. Combine the organic phases and dry them with anhydrous sodium sulfate. Remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) as the eluent to obtain approximately 2.31 g of compound 2-8, yield: 69%. MS: 1117.64.

[0099] Synthesis of compound (2):

[0100] Accurately weigh compounds 2-8 (2.23 g, 2 mmol) and 2-9 (0.99 g, 5 mmol), and add them sequentially to a 100 ml three-necked flask. Add 40 ml of chloroform, purge with argon three times, and then add 1.0 ml of piperidine. Heat to 60 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Wash the crude product with 20 ml of methanol, filter, dissolve the filter cake in dichloromethane, and add silica gel to a stirred column for chromatography. The eluent is PE:DCM = 1:1 (volume ratio). Approximately 1.8 g of compound (2) was obtained, yield: 62%. MALDI-TOF MS: 1475.90.

[0101] Example 2: Synthesis of compound (7)

[0102]

[0103] Synthesis of compound 7-2:

[0104] Accurately weigh compounds 2-4 (4.85 g, 10 mmol), 7-1 (7.18 g, 20 mmol), and tetraphenylphosphine palladium (0.46 g, 0.4 mmol) and add them sequentially to a 100 mL three-necked flask. Add 50 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 3:1 (v / v) to obtain approximately 5.1 g of compound 7-2, yield: 71%. MS: 715.75.

[0105] Synthesis of compound 7-4:

[0106] Accurately weigh compound 7-2 (1.4 g, 2 mmol), compound 7-3 (1.4 g, 4.2 mmol), and tetraphenylphosphine palladium (0.092 g, 0.08 mmol) into a 100 mL three-necked flask. Add 15 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 3:1 (v / v). This yields approximately 1.65 g of compound 7-4, yield: 84%. MS: 979.82.

[0107] Synthesis of compound 7-5:

[0108] Accurately weigh 1.47 g (1.5 mmol) of compound 7-4 and add it to a 50 mL three-necked flask. Add 20 mL of anhydrous THF and purge with argon three times. Cool to -78 °C and slowly add 1.2 mL (2.5 M, 3.3 mmol) of n-butyllithium to the solution. After reacting at -78 °C for 1 h, add 1.0 g (5 mmol) of trimethyltin chloride to the three-necked flask. After reacting for one hour, raise the temperature to room temperature and continue stirring overnight. Quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Recrystallize the crude product from isopropanol to give approximately 1.51 g of compound 7-5, yield: 77%. MALDI-TOF MS: 1305.46.

[0109] Synthesis of compound 7-7:

[0110] Accurately weigh compound 7-5 (1.43 g, 1.1 mmol), compound 7-6 (0.41 g, 2.2 mmol), and tetraphenylphosphine palladium (0.092 g, 0.08 mmol) into a 100 mL three-necked flask. Add 15 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 5:1 (v / v). This yields approximately 0.95 g of compound 7-7, yield: 72%. MALDI-TOFMS: 1193.68.

[0111] Synthesis of compounds 7-8:

[0112] Accurately weigh compound 7-7 (0.84 g, 0.7 mmol) and add it to a 50 mL three-necked flask. Add 3.5 mL of anhydrous DMF, purge with argon three times, and then cool to 0 °C in an ice-salt bath. Weigh phosphorus oxychloride (0.15 g, 1 mmol) and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 1 h. Then, raise the temperature to 80 °C and react for 12 h. Cool to room temperature, quench the reaction solution in water, and extract three times with dichloromethane. Combine the organic phases and dry them with anhydrous sodium sulfate. Remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) as the eluent to obtain approximately 0.57 g of compound 7-8, yield: 65%. MALDI-TOFMS: 1249.71.

[0113] Synthesis of compound (7):

[0114] Accurately weigh compounds 7-8 (0.37 g, 0.3 mmol) and compounds 2-9 (0.15 g, 0.75 mmol) and add them sequentially to a 50 ml three-necked flask. Add 15 ml of chloroform, purge with argon three times, and then add 0.15 ml of piperidine. Heat to 60 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Wash the crude product with 100 ml of methanol, filter, dissolve the filter cake in dichloromethane, and add silica gel to a stirred column for chromatography. The eluent is PE:DCM = 1:1 (volume ratio). Approximately 0.29 g of compound (7) was obtained, yield: 60%. MALDI-TOF MS: 1608.39.

[0115] Example 3: Synthesis of compound (10)

[0116]

[0117]

[0118] Synthesis of compound 10-2:

[0119] Accurately weigh 2.32 g (10 mmol) of compound 10⁻¹ and add it to a 100 mL three-necked flask. Add 40 mL of DMF, purge the flask three times with nitrogen, and then weigh 1.78 g (10 mmol) of N-bromosuccinamide (NBS) and dissolve it in 10 mL of DMF. Slowly add this solution dropwise to the above solution containing 10⁻¹ at room temperature. After the addition is complete, react for 3 h. Pour the reaction solution into water, extract with ethyl acetate, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE as the eluent to obtain approximately 2.4 g of compound 10⁻², yield: 76%. MS: 311.53.

[0120] Synthesis of compound 10⁻³:

[0121] Accurately weigh 1.56 g (5 mmol) of compound 10⁻² into a 100 mL three-necked flask, add 20 mL of anhydrous THF, and purge with argon three times. Cool to -78 °C, and slowly add 2.1 mL (2.5 M, 5.25 mmol) of n-butyllithium dropwise to the solution. After reacting at -78 °C for 1 h, add 1.0 g (5 mmol) of trimethyltin chloride to the three-necked flask, react for one hour, then raise to room temperature and continue stirring overnight. Quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Recrystallize the crude product from methanol to give approximately 1.6 g of compound 10⁻³, yield: 81%. MS: 395.11.

[0122] Synthesis of compound 10⁻⁴:

[0123] Accurately weigh compound 2-4 (0.97 g, 2 mmol), compound 10-3 (1.58 g, 4 mmol), and tetraphenylphosphine palladium (0.092 g, 0.08 mmol) into a 100 mL three-necked flask. Add 15 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 3:1 (v / v). This yields approximately 1.35 g of compound 10-4, yield: 85.7%. MS: 787.88.

[0124] Synthesis of compound 10-5:

[0125] Accurately weigh compound 10⁻⁴ (1.35 g, 1.7 mmol), compound 7⁻⁃ (1.2 g, 3.5 mmol), and tetraphenylphosphine palladium (0.092 g, 0.08 mmol) into a 100 mL three-necked flask. Add 15 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 3:1 (v / v). This yields approximately 1.54 g of compound 10⁻⁵ (yield: 86.2%). MS: 10⁵ 1.84.

[0126] Synthesis of compound 10⁻⁶:

[0127] Accurately weigh 1.54 g (1.5 mmol) of compound 10⁻⁵ and add it to a 50 mL three-necked flask. Add 20 mL of anhydrous THF and purge with argon three times. Cool to -78 °C and slowly add 1.2 mL (2.5 M, 3.3 mmol) of n-butyllithium to the solution. After reacting at -78 °C for 1 h, add 1.0 g (5 mmol) of trimethyltin chloride to the three-necked flask. After reacting for one hour, raise the temperature to room temperature and continue stirring overnight. Quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Recrystallize the crude product from isopropanol to give approximately 1.45 g of compound 10⁻⁶, yield: 70.1%. MALDI-TOF MS: 1377.59.

[0128] Synthesis of compound 10-7:

[0129] Accurately weigh compound 10⁻⁶ (1.45 g, 1.1 mmol), compound 7⁻⁶ (0.41 g, 2.2 mmol), and tetraphenylphosphine palladium (0.092 g, 0.08 mmol) into a 100 mL three-necked flask. Add 15 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 5:1 (v / v). This yields approximately 1.15 g of compound 10⁻⁷, yield: 82.5%. MALDI-TOFMS: 1265.87.

[0130] Synthesis of compound 10-8:

[0131] Accurately weigh 1.15 g (0.9 mmol) of compound 10⁻⁷ and add it to a 50 mL three-necked flask. Add 3.5 mL of anhydrous DMF, purge with argon three times, and then cool to 0 °C in an ice-salt bath. Weigh 0.15 g (1 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 1 h. Then, raise the temperature to 80 °C and react for 12 h. Cool to room temperature, quench the reaction solution in water, and extract three times with dichloromethane. Combine the organic phases and dry them with anhydrous sodium sulfate. Remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) as the eluent to obtain approximately 0.82 g of compound 10⁻⁸, yield: 68.9%. MALDI-TOFMS: 1321.87.

[0132] Synthesis of compound (10):

[0133] Accurately weigh compound 10-8 (0.39 g, 0.3 mmol) and compound 2-9 (0.15 g, 0.75 mmol) and add them sequentially to a 50 ml three-necked flask. Add 15 ml of chloroform, purge with argon three times, and then add 0.15 ml of piperidine. Heat to 60 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Wash the crude product with 100 ml of methanol, filter, dissolve the filter cake in dichloromethane, and add silica gel to a stirred column for chromatography. The eluent is PE:DCM = 1:1 (volume ratio). Approximately 0.28 g of compound (10) was obtained, yield: 57%. MALDI-TOF MS: 1680.33.

[0134] Example 4: Synthesis of compound (14)

[0135]

[0136] Synthesis of compound 14-3:

[0137] Accurately weigh 17.7 g (50 mmol) of compound 14-1, 13.6 g (50 mmol) of compound 14-2, and 0.58 g (0.5 mmol) of tetraphenylphosphine palladium, and add them sequentially to a 500 mL three-necked flask. Add 200 mL of anhydrous toluene, purge with argon three times, and then heat to 80 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with PE as the eluent to obtain approximately 15.6 g of compound 14-3, yield: 81.6%. MS: 382.40.

[0138] Synthesis of compound 14-4:

[0139] Accurately weigh 15.3 g (40 mmol) of compound 14-3 into a 500 mL three-necked flask, add 200 mL of anhydrous THF, and purge with argon three times. Cool to -78 °C, and slowly add 16 mL (2.5 M, 40 mmol) of n-butyllithium dropwise to the solution. After reacting at -78 °C for 1 h, add 7.96 g (40 mmol) of trimethyltin chloride to the three-necked flask, react for one hour, then raise to room temperature and continue stirring overnight. Quench with water, extract with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Recrystallize the crude product from methanol to give approximately 12.7 g of compound 14-4, yield: 68.1%. MS: 466.38

[0140] Synthesis of compound 14-5:

[0141] Accurately weigh compound 2-6 (1.88 g, 2.5 mmol), compound 14-4 (2.33 g, 5 mmol), and bis(benzylacetone)palladium (0.06 g, 0.1 mmol) into a 100 mL three-necked flask. Add 30 mL of anhydrous toluene, purge with argon three times, and then heat to 110 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:EA eluent ratio of 3:1 (v / v). This yields approximately 2.1 g of compound 14-5, with a yield of 64%. MALDI-TOF MS: 1285.94.

[0142] Synthesis of compound 14-6:

[0143] Accurately weigh 1.93 g (1.5 mmol) of compound 14-5 and add it to a 100 mL three-necked flask. Add 10 mL of anhydrous DMF, purge with argon three times, and then cool to 0 °C in an ice-salt bath. Weigh 1.38 g (9 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 1 h. Then, raise the temperature to 80 °C and react for 12 h. Cool to room temperature, quench the reaction solution in water, and extract three times with dichloromethane. Combine the organic phases and dry them with anhydrous sodium sulfate. Remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) as the eluent to obtain approximately 1.15 g of compound 14-6, yield: 57%. MALDI-TOF MS: 1341.82.

[0144] Synthesis of compound (14):

[0145] Accurately weigh compound 14-6 (1.0 g, 0.75 mmol) and compound 2-9 (0.37 g, 0.19 mmol) and add them sequentially to a 100 ml three-necked flask. Add 20 ml of chloroform, purge with argon three times, and then add 0.4 ml of piperidine. Heat to 60 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Wash the crude product with 10 ml of methanol, filter, dissolve the filter cake in dichloromethane, and add silica gel to a stirred column for chromatography. The eluent is PE:DCM = 1:1 (volume ratio). Approximately 0.74 g of compound (14) was obtained, yield: 58%. MALDI-TOF MS: 1700.83.

[0146] Example 5: Synthesis of compound (17)

[0147]

[0148] Synthesis of compound 17-2:

[0149] Accurately weigh compounds 2-4 (4.85 g, 10 mmol), 17-1 (11.39 g, 20 mmol), and tetraphenylphosphine palladium (4- 0.46 g, 0.4 mmol) into a 100 mL three-necked flask. Add 50 mL of anhydrous toluene, purge with argon three times, and then heat to 95 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:DCM eluent of 3:1 (v / v). This yields approximately 6.2 g of compound 17-2 (70% yield). MS: 884.33.

[0150] Synthesis of compound 17-3:

[0151] Accurately weigh compound 17-2 (4.42 g, 5 mmol), compound 14-4 (4.66 g, 10 mmol), and bis(benzylacetone)palladium (0.12 g, 0.2 mmol) into a 100 mL three-necked flask. Add 40 mL of anhydrous toluene, purge with argon three times, and then heat to 110 °C for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and perform silica gel column chromatography with a PE:EA eluent ratio of 3:1 (v / v). This yields approximately 4.75 g of compound 17-3, with a yield of 67%. MALDI-TOFMS: 1418.26.

[0152] Synthesis of compound 17-4:

[0153] Accurately weigh 4.25 g (3 mmol) of compound 17-3 and add it to a 10 mL three-necked flask. Add 30 mL of anhydrous DMF, purge with argon three times, and then cool to 0 °C in an ice-salt bath. Weigh 2.75 g (18 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 1 h. Then, raise the temperature to 80 °C and react for 12 h. Cool to room temperature, quench the reaction solution in water, and extract three times with dichloromethane. Combine the organic phases and dry them with anhydrous sodium sulfate. Remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) as the eluent to obtain approximately 2.2 g of compound 17-4, yield: 49%. MALDI-TOFMS: 1474.38.

[0154] Synthesis of compound (17):

[0155] Accurately weigh compound 17-4 (1.47 g, 1 mmol) and compound 2-9 (0.49 g, 2.5 mmol) and add them sequentially to a 100 ml three-necked flask. Add 20 ml of chloroform, purge with argon three times, and then add 0.5 ml of piperidine. Heat to 60 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Wash the crude product with 10 ml of methanol, filter, dissolve the filter cake in dichloromethane, and add silica gel to a stirred column for chromatography. The eluent is PE:DCM = 1:1 (volume ratio). Approximately 1.0 g of compound (17) was obtained, yield: 56%. MALDI-TOF MS: 1832.81.

[0156] Synthesis of the comparative compound (ref):

[0157]

[0158] Synthesis of compound REF-2:

[0159] Accurately weigh compound REF-1 (1.37 g, 5 mmol), pinacol diborate (2.54 g, 10 mmol), Pd(dppf)Cl2 (0.07 g), and potassium acetate (0.98 g, 10 mmol) into a 100 mL three-necked flask. Add 20 mL of anhydrous dioxane and purge with argon three times. Heat to 100 °C and react for 4 hours. After the reactants have completely reacted, dilute 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) to obtain approximately 1.31 g of compound REF-2, yield: 81.8%. MS: 320.35.

[0160] Synthesis of compound REF-3:

[0161] Accurately weigh compound 2-6 (1.50 g, 2 mmol), compound REF-2 (1.28 g, 4 mmol), bis(triphenylphosphine)palladium dichloride (0.14 g), and potassium carbonate (0.69 g, 5 mmol) and add them sequentially to a 100 mL three-necked flask. Add 30 mL of toluene and 5 mL of water, purge with argon three times, and then heat to 110 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Dissolve the crude product in dichloromethane and add it to a silica gel stirred column for chromatography. The eluent is PE:EA = 3:1 (v / v), yielding approximately 1.64 g of compound REF-3, yield: 77%. MS: 1067.51.

[0162] Synthesis of compound (REF):

[0163] Accurately weigh compound REF-3 (1.07 g, 1 mmol) and compound 2-9 (0.49 g, 2.5 mmol) and add them sequentially to a 100 mL three-necked flask. Add 20 mL of chloroform, purge with argon three times, and then add 0.5 mL of piperidine. Heat to 60 °C and react for 12 h. Cool to room temperature and remove excess solvent by vacuum distillation. Wash the crude product with 10 mL of methanol, filter, dissolve the filter cake in dichloromethane, and perform chromatography on a silica gel stirred column with PE:DCM = 1:1 (v / v). Approximately 0.88 g of compound (REF) was obtained, yield: 62%. MALDI-TOF MS: 1426.08.

[0164] OPV device fabrication examples:

[0165] The fabrication process of the OPV device comprising the above-mentioned compounds is described in detail below through specific embodiments. The OPV device structure is as follows: Indium Tin Oxide (ITO) / PEI-Zn / Active Layer / MoO3 / Ag

[0166] The fabrication steps of device example 1 are as follows:

[0167] 1) ITO substrate cleaning:

[0168] Clean the ITO conductive glass with detergent, rinse it thoroughly, and then ultrasonically clean it for 15 minutes with deionized water, acetone, and isopropanol. After that, dry it with nitrogen and treat it in a plasma cleaner for 5 minutes to further clean the surface and improve wettability.

[0169] 2) Preparation of cathode buffer layer

[0170] The PEI-Zn solution was uniformly spin-coated onto ITO in air at a speed of 1500-4000 rpm / min, and then dried at 150℃ for 5 min to obtain a cathode buffer layer with a thickness of 50 nm.

[0171] 3) Preparation of photoactive layer

[0172] In a glove box (inert gas atmosphere), the photoactive layer material is uniformly spin-coated onto the cathode buffer layer at a rotation speed of 1800-4000 rpm to obtain an active material layer with a total thickness of 100 nm; wherein the donor material in the photoactive layer material is selected from compound (2); the acceptor material is selected from (A-2) and (A-15); the mass ratio of compound (2): (A-2): (A-15) is 1:1:0.2; specifically: the active donor material and the acceptor material are dissolved in chloroform, and 0.25% by volume of 1,8-diiodooctane (DIO) is added as an additive.

[0173] 4) Preparation of the anode buffer layer

[0174] In high vacuum (1×10 -6 MoO3 was deposited onto the photoactive layer in millibars to obtain an anode buffer layer with a thickness of 10 nm.

[0175] 5) Anode layer preparation

[0176] In high vacuum (1×10 -6 Ag is vapor-deposited onto the anode buffer layer in millibars to form an anode layer with a thickness of 100 nm.

[0177] 6) Packaging

[0178] The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0179] Device Examples 2-5:

[0180] The donor material compound (2) in the photoactive layer of device Example 1 was replaced with compound (7), compound (10), compound (14) and compound (17), respectively, as shown in Table 1. Other steps were the same, resulting in device Examples 2-5.

[0181] Device Comparison Example 1:

[0182] Replace the donor material compound (2) in the photoactive layer of device Example 1 with compound (REF), and follow the same steps to obtain device Comparative Example 1.

[0183] The performance of the fabricated organic solar cell device was tested. Under AM1.5G standard light irradiation using a solar simulator (SS-F5-3A), the cell current-voltage curve was measured, and the photoelectric conversion efficiency was calculated.

[0184] Table 1

[0185] Photoactive layer donor materials Photoelectric conversion efficiency (%) Device Example 1 Compound (2) 14.44 Device Example 2 Compound (7) 13.76 Device Example 3 Compound (10) 15.29 Device Example 4 Compound (14) 14.85 Device Example 5 Compound (17) 14.07 Device Comparison Example 1 Compound (REF) 11.81

[0186] As can be seen from the device characterization of the above-described device embodiments, the five-membered fused ring organic compound protected in this application utilizes the five-membered fused ring donor unit. It exhibits excellent photoelectric conversion performance when connected to cyano ester electron-withdrawing units through substituted bithiophene.

[0187] Among them, the performance of device Example 1 was improved by 22% compared with that of device Comparative Example 1. The reason is that the compound (2) of this application introduces a cyano group substitution at a specific site of the connecting unit compared with the comparative compound REF. As a strong electron-withdrawing group, the cyano group has functions such as inducing molecular aggregation and promoting crystallization, and plays a significant role in regulating the morphology of the active layer of photovoltaic devices. At the same time, the introduction of the cyano group can achieve a lower HOMO energy level, thereby increasing the open-circuit voltage of the device and thus improving the photoelectric conversion efficiency of the device.

[0188] The performance of device Example 4 was improved by 26% compared with that of device Comparative Example 1. The reason is that the compound (14) of this application not only introduced the substitution of cyano group in the connecting unit thiophene compared with the comparative compound REF, but also introduced the substitution of alkyl group, thereby adjusting the spatial structure, solubility and energy level structure of the compound, so that it can perform better as a photoactive layer donor material.

[0189] The above embodiments further illustrate the content of this application, but should not be construed as limiting this application. Modifications and substitutions made to the methods, steps, or conditions of this application without departing from the spirit and substance of this application are all within the scope of this application. Unless otherwise specified, the technical means used in the embodiments are conventional means well known to those skilled in the art.

Claims

1. A five-membered fused-ring organic compound, characterized in that: The five-membered fused-ring organic compound has a structure as shown in general formula (I): （I） in: R1, R2, R4, and R5 are each independently selected from -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, -Cl, -Br, -F, and -I. Each time R3 appears, it is independently selected from straight-chain alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms; Each time R6 appears, it is independently selected from straight-chain alkyl groups having 1 to 20 carbon atoms, or branched alkyl groups having 3 to 20 carbon atoms.

2. The five-membered fused-ring organic compound according to claim 1, characterized in that: Each time R1 and R2 appear, they are independently selected from -H, -D, straight-chain alkyl groups having 1 to 10 C atoms, branched alkyl groups having 3 to 10 C atoms, -Cl, -Br, -F, and -I.

3. The five-membered fused-ring organic compound according to claim 1, characterized in that: Each time R3 appears, it is selected independently. , or .

4. A five-membered fused-ring organic compound according to claim 1, 2, or 3, characterized in that: Each occurrence is selected from any of the following groups, either identically or differently: ; In this context, * indicates a connection site.

5. The five-membered fused-ring organic compound according to claim 1, characterized in that: R4 and R5 are each independently selected from -H, -D, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched alkyl groups having 3 to 10 carbon atoms. Each time R6 appears, it is independently selected from straight-chain alkyl groups having 1 to 10 carbon atoms, or branched alkyl groups having 3 to 10 carbon atoms.

6. The five-membered fused-ring organic compound according to claim 5, characterized in that: Each occurrence is selected from any of the following groups: ； * indicates a connection point.

7. The five-membered fused-ring organic compound according to claim 5, characterized in that: Selected from or .

8. A five-membered fused-ring organic compound, characterized in that: The five-membered fused-ring organic compound is selected from the following structures: 。 9. A mixture, characterized in that: The mixture includes a five-membered fused-ring organic compound as described in any one of claims 1-8, and at least one other organic functional material; the other organic functional material is selected from photoactive layer acceptor materials or photoactive layer donor materials.

10. A composition, characterized in that: The composition comprises a five-membered fused-ring organic compound as described in any one of claims 1-8 or a mixture as described in claim 9, and at least one organic solvent.

11. An organic electronic device, characterized in that: The organic electronic device comprises at least a first electrode, a second electrode, and a photoactive layer located between the first electrode and the second electrode; the photoactive layer material comprises at least one five-membered fused-ring organic compound as described in any one of claims 1-8 or a mixture as described in claim 9.

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