A non-fullerene acceptor compound and its use in organic electronic devices

Abstract

The application relates to the field of organic solar device materials, in particular to a non-fullerene acceptor material compound. The application provides a novel oligomeric non-fullerene acceptor compound. By taking a high-performance non-fullerene acceptor unit as a monomer, a strategy of constructing an oligomeric acceptor by using a connecting group in the core is adopted, so that the material has the advantages of small molecules and polymers, has good batch repeatability and good film-forming property, and simultaneously has a relatively high photoelectric conversion efficiency.

Description

Technical Field

[0001] This invention relates to the field of organic solar energy device materials, and in particular to a non-fullerene acceptor compound and its application in organic electronic devices. Background Technology

[0002] Organic solar cells (OSCs) convert clean and renewable solar energy into electrical energy. Since the 1990s, they have emerged and have broad application and development prospects in areas such as IoT sensing devices such as electronic tags, building and equipment integration, automotive glass and wearable devices due to their advantages such as low cost, light weight, simple manufacturing process and large-area flexible manufacturing.

[0003] Organic solar cells generally consist of five parts: anode, anode buffer layer, active layer, cathode buffer layer, and cathode. The active layer typically contains both donor and acceptor materials. The choice of active layer material is crucial to the efficiency of organic solar cell devices. In the early and middle stages of organic solar cell development, PC (polycarbonate) was the primary material used. 61 BM and PC 71 Fullerenes and their derivatives, represented by BM, have dominated electron acceptor materials due to their high electron affinity, isotropic electron transport capabilities, and high electron mobility; this period is often referred to as the fullerene era. However, the limitations of the fullerene acceptor molecular structure result in weak absorption in the visible and near-infrared regions and poor energy level tunability, thus restricting the efficiency improvement of organic solar cells.

[0004] In recent years, the emergence of non-fullerene acceptor materials has, to some extent, overcome the shortcomings of fullerene acceptors, greatly improving the photoelectric conversion efficiency of devices and promoting the development of organic solar cells. Existing non-fullerene acceptor materials are mostly small-molecule acceptor materials, such as Y6, Y18, ITIC, and IDIC. However, small-molecule acceptors are prone to aggregation and excessive phase separation after blending with polymer donor materials. They are also greatly affected by thin-film preparation conditions, limiting the development of large-area printing fabrication of organic solar cells. Therefore, oligomeric non-fullerene acceptors have attracted widespread attention.

[0005] Summary of the Invention

[0006] The purpose of this invention is to provide a novel oligomeric nonfullerene acceptor compound that exhibits good batch repeatability and film-forming properties, while also demonstrating high photoelectric conversion efficiency.

[0007] The technical solution of the present invention is as follows:

[0008] A non-fullerene acceptor compound having a structure as shown in general formula (I-1) or general formula (I-2):

[0009]

[0010] in,

[0011] A1, A2, and A3 are independently selected from general formula II.

[0012]

[0013] in,

[0014] Each time M appears, it is independently selected from O or C(CN)2;

[0015] L1 and L2 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or substituted or unsubstituted nonaromatic ring systems having 5 to 30 ring atoms.

[0016] Each occurrence of Ar1 is independently selected from substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms, or substituted or unsubstituted nonaromatic groups having 5 to 40 ring atoms.

[0017] R0, R1, R2, R3, and R4 are each independently selected from: -H, -D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 3 to 6 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, or groups formed by combinations of the above groups;

[0018] Each time R5 appears, it is independently selected from -H, -D, a straight-chain alkyl group having 1 to 15 carbon atoms, a straight-chain alkoxy group having 1 to 15 carbon atoms, a straight-chain alkathio group having 1 to 15 carbon atoms, a branched or cyclic alkyl group having 3 to 15 carbon atoms, a branched or cyclic alkoxy group having 3 to 15 carbon atoms, a branched or cyclic alkathio group having 3 to 15 carbon atoms, an alkoxy carbonyl group having 2 to 15 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups;

[0019] m is selected from 0, 1, 2, 3, 4 or 5;

[0020] n is selected from 0, 1, 2, 3, 4 or 5;

[0021] * indicates a connection site.

[0022] "Substituted or unsubstituted" means that the defined group is unsubstituted or is substituted by one or more substituents R. * Replace; R* Each occurrence is independently selected from -D, a straight-chain alkyl group having 1 to 30 carbon atoms, a straight-chain alkoxy group having 1 to 30 carbon atoms, a straight-chain alkylthio group having 1 to 30 carbon atoms, a branched or cyclic alkyl group having 3 to 30 carbon atoms, a branched or cyclic alkoxy group having 3 to 30 carbon atoms, a branched or cyclic alkoxy group having 3 to 30 carbon atoms, an alkoxycarbonyl group having 2 to 30 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by a combination of the above groups.

[0023] The present invention also provides a mixture comprising the above-mentioned non-fullerene acceptor compound and at least one organic functional material, wherein the organic functional material is selected from anodic buffer layer material, cathode buffer layer material, active layer donor material, or active layer acceptor material.

[0024] An organic electronic device includes at least one functional layer, wherein the material of the functional layer is selected from the above-mentioned non-fullerene acceptor compounds or mixtures.

[0025] Beneficial effects:

[0026] ① The compound provided by this invention is a novel oligomeric nonfullerene acceptor compound. By using high-performance nonfullerene acceptor units as monomers and constructing oligomeric acceptors with linking groups at the core, the material combines the advantages of small molecules and polymers, giving it good batch repeatability and good film-forming properties.

[0027] ②Thiophene in the core linking group has electron-donating properties, which can effectively regulate the aggregation characteristics and electronic energy levels of the compound, and can be modified with side chain diversity, thereby regulating the molecular morphology and solubility of the compound;

[0028] ③ The compounds provided by this invention, when used as acceptor materials in organic solar cells, exhibit excellent photoelectric performance. Attached Figure Description

[0029] 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.

[0030] Figure 1 This is a schematic diagram of the structure of an organic solar energy device provided in an embodiment of this application.

[0031] In the figure, 101 is the substrate, 102 is the anode layer, 103 is the anode buffer layer, 104 is the photoactive layer, 105 is the cathode buffer layer, and 106 is the cathode layer. Detailed Implementation

[0032] To make the objectives, technical solutions, and effects of this application clearer and more explicit, the following provides a further detailed description of this application. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the scope of this application.

[0033] The terms "and / or," "or / and," and "and / or" as used herein include any one of two or more of the related listed items, as well as any and all combinations of the related listed items. These arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or," "or / and," and "and / or," it should be understood that in this application, the technical solution undoubtedly includes technical solutions connected by "logical AND," and also undoubtedly includes technical solutions connected by "logical OR." For example, "A and / or B" includes three parallel solutions: A, B, and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, a technical solution that is connected by "logical OR"), as well as any and all combinations of A, B, C, and D, that is, combinations of any two or three of A, B, C, and D, and also combinations of all four of A, B, C, and D (that is, a technical solution that is connected by "logical AND").

[0034] In this invention, organic photovoltaic devices, organic solar cells, OPV, and OSC have the same meaning and can be used interchangeably.

[0035] In this invention, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0036] In this invention, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0037] In this invention, "heteroatoms" are non-carbon atoms, and can be N atoms, O atoms, S atoms, etc.

[0038] In this invention, "substitution" means that one or more hydrogen atoms in the substituent are replaced by the substituent.

[0039] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0040] In this invention, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0041] In this invention, "aromatic group" refers to any optional functional group or substituent derived from an aromatic carbon ring. The aromatic group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aromatic group can be a monocyclic aromatic group, a fused-ring aromatic group, two or more monocyclic aromatic groups conjugated by carbon-carbon bonds, a monocyclic aromatic group and a fused-ring aromatic group conjugated by carbon-carbon bonds, or two or more fused-ring aromatic groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as the aromatic group of this application. Preferably, the aromatic group is selected from aromatic groups having 6-30 carbon atoms; further, it is selected from aromatic groups having 6-20 carbon atoms; further, it is selected from aromatic groups having 6-10 carbon atoms; the aromatic group includes, but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives.

[0042] In this invention, a "heteroaromatic group" refers to a monovalent aromatic ring or its derivative containing one, two, three, four, five, six or more heteroatoms. The heteroatoms can be at least one of B, O, N, P, Si, Se, and S. The heteroaromatic group can be a monocyclic heteroaryl or a polycyclic heteroaryl; in other words, it can be a single aromatic ring system or a system of multiple aromatic rings conjugated by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. Preferably, the heteroaromatic group is selected from heteroaromatic groups having 6-30 ring atoms; further, it is selected from heteroaromatic groups having 6-20 ring atoms; further, it is selected from heteroaromatic groups having 6-10 ring atoms. Heteroaromatic groups include, but are not limited to: thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinazolinyl, etc. Oxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthrynyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0043] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in a straight-chain alkyl group can be 1 to 20, 1 to 15, or 1 to 6; the number of carbon atoms in a branched alkyl group can be 3 to 20, 3 to 15, or 3 to 6; and the number of carbon atoms in a cyclic alkyl group can be 3 to 20, 3 to 15, or 3 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl 2-Butyloctyl, 2-Hexyloctyl, 3,7-Dimethyloctyl, Cyclooctyl, Nonyl, Decyl, Adamantyl, 2-Ethyldecyl, 2-Butyldecyl, 2-Hexyldecyl, 2-Octylide, Undecyl, Dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octylide, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octylide, Heptadecanyl, Octadecanyl, Nonadecanyl, Eicosyl, etc.

[0044] The term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. 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).

[0045] The term "alkylthio" refers to a group with the structure "-S-alkyl", that is, an alkyl group as defined above that is attached to other groups via a sulfur atom. 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).

[0046] In this invention, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0047] In this invention, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring can be the same or different from each other.

[0048] In this invention, the phrase "independently selected" means that when one or more groups appear simultaneously and in multiple places in the compound, they are all independently selected and can be the same or different.

[0049] In this invention, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be connected to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0050] The terms “combinations thereof,” “any combination thereof,” “any combination thereof,” and “combination” used in this invention include all suitable combinations of any two, any three, or any three or more items of the listed groups.

[0051] 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.

[0052] 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.

[0053] In this invention, the technical features described in an open-ended manner include both closed-ended technical solutions composed of the listed features and open-ended technical solutions that include the listed features.

[0054] A non-fullerene acceptor compound having a structure as shown in general formula (I-1) or general formula (I-2):

[0055]

[0056] in,

[0057] A1, A2, and A3 are independently selected from general formula II.

[0058]

[0059] in,

[0060] Each time M appears, it is independently selected from O or C(CN)2;

[0061] L1 and L2 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, or substituted or unsubstituted nonaromatic ring systems having 5 to 30 ring atoms.

[0062] Each occurrence of Ar1 is independently selected from substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms, or substituted or unsubstituted nonaromatic groups having 5 to 40 ring atoms.

[0063] R0, R1, R2, R3, and R4 are each independently selected from: -H, -D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 3 to 6 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, or groups formed by combinations of the above groups;

[0064] Each time R5 appears, it is independently selected from -H, -D, a straight-chain alkyl group having 1 to 15 carbon atoms, a straight-chain alkoxy group having 1 to 15 carbon atoms, a straight-chain alkathio group having 1 to 15 carbon atoms, a branched or cyclic alkyl group having 3 to 15 carbon atoms, a branched or cyclic alkoxy group having 3 to 15 carbon atoms, a branched or cyclic alkathio group having 3 to 15 carbon atoms, an alkoxy carbonyl group having 2 to 15 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups;

[0065] m is selected from 0, 1, 2, 3, 4 or 5;

[0066] n is selected from 0, 1, 2, 3, 4 or 5;

[0067] * indicates a connection point.

[0068] In this invention, "substituted or unsubstituted" means that the defined group is unsubstituted or is substituted by one or more substituents R. * Replace, R * Each occurrence is independently selected from -D, a straight-chain alkyl group having 1 to 30 carbon atoms, a straight-chain alkoxy group having 1 to 30 carbon atoms, a straight-chain alkylthio group having 1 to 30 carbon atoms, a branched or cyclic alkyl group having 3 to 30 carbon atoms, a branched or cyclic alkoxy group having 3 to 30 carbon atoms, a branched or cyclic alkoxy group having 3 to 30 carbon atoms, an alkoxycarbonyl group having 2 to 30 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by a combination of the above groups.

[0069] Furthermore, R * Each occurrence is independently selected from -D, 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 alkathio 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 alkathio group having 3 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms, or a group formed by a combination of the above groups.

[0070] In one embodiment, each occurrence of R5 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 carbon atoms, a straight-chain alkoxy group having 1 to 10 carbon atoms, a straight-chain alkathio group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, a branched or cyclic alkoxy group having 3 to 10 carbon atoms, a branched or cyclic alkathio group having 3 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the above groups.

[0071] Furthermore, the aforementioned Each time it appears, selected from In this context, R5 is selected independently from straight-chain alkyl groups having 1 to 10 carbon atoms, straight-chain alkoxy groups having 1 to 10 carbon atoms, straight-chain alkylthio groups having 1 to 10 carbon atoms, branched or cyclic alkyl groups having 3 to 10 carbon atoms, branched or cyclic alkoxy groups having 3 to 10 carbon atoms, branched or cyclic alkoxy groups having 3 to 10 carbon atoms, alkoxycarbonyl groups having 2 to 10 carbon atoms, cyano groups, nitro groups, -Cl groups, -Br groups, -F groups, -I groups, and -CF3 groups. This is because optimizing the side chains of the linking groups allows for further adjustment of the compound's solubility, molecular planarity, and molecular energy levels, thereby resulting in superior photoelectric properties.

[0072] In one specific embodiment, each occurrence of R5 is independently selected from straight-chain or branched alkyl groups having 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, or -CF3. In one embodiment, Each occurrence is selected from the same structure. Furthermore, the... Selected from the following structures:

[0073]

[0074] Furthermore, the aforementioned Selected from the following structures:

[0075]

[0076] Where: * indicates a connection site.

[0077] Specifically, each occurrence of Ar1 is independently selected from the following structure:

[0078]

[0079] Each time Ar2 and Ar3 appear, they are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 20 ring atoms.

[0080] Each occurrence of W, Y1, Y2, Y3, Y4, Y5, and Y6 is independently selected from O, S, Se, and NR. 12 CR 13 R 14 ;

[0081] R6-R 14Each occurrence is independently selected from -H, -D, straight-chain alkyl groups having 1 to 30 carbon atoms, straight-chain alkoxy groups having 1 to 30 carbon atoms, straight-chain alkylthio groups having 1 to 30 carbon atoms, branched or cyclic alkyl groups having 3 to 30 carbon atoms, branched or cyclic alkoxy groups having 3 to 30 carbon atoms, branched or cyclic alkoxy groups having 3 to 30 carbon atoms, alkoxycarbonyl groups having 2 to 30 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, aromatic groups having 6 to 10 ring atoms, heteroaromatic groups having 5 to 10 ring atoms, or groups formed by combinations of the above groups.

[0082] More specifically, Ar2 is selected from the following structure:

[0083]

[0084] Wherein: X is selected independently from CR each time it appears. 15 Or N;

[0085] Each time Y appears, it is independently selected from: O, S, Se, NR. 16 ;

[0086] R 15 -R 16 Each occurrence is independently selected from: -H, -D, straight-chain alkyl with 1 to 30 carbon atoms, straight-chain alkoxy with 1 to 30 carbon atoms, straight-chain alkathiol with 1 to 30 carbon atoms, branched or cyclic alkyl with 3 to 30 carbon atoms, branched or cyclic alkoxy with 3 to 30 carbon atoms, branched or cyclic alkathiol with 3 to 30 carbon atoms, alkoxycarbonyl with 2 to 30 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, aromatic group with 6 to 10 ring atoms, heteroaromatic group with 5 to 10 ring atoms, or a group formed by a combination of the above groups;

[0087] # indicates a fusion site, and the fusion site is selected from C atoms.

[0088] Preferably, Ar2 is selected from any of the following structures:

[0089]

[0090] Preferably, Y is selected from S or Se.

[0091] In one embodiment, (A-1) is selected from the following structures:

[0092]

[0093]

[0094] Preferred, R6-R14 Each occurrence is independently selected from -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy 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, -Cl, -Br, -F, -I, aromatic groups having 6 to 10 cyclic atoms, or groups formed by a combination of aromatic groups having 6 to 10 cyclic atoms and straight-chain alkyl groups having 1 to 20 carbon atoms.

[0095] Preferably, each occurrence of R6 and R7 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy 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, -Cl, -Br, -F, -I, an aromatic group having 6 to 10 cyclic atoms, or a group formed by a combination of an aromatic group having 6 to 10 cyclic atoms and a straight-chain alkyl group having 1 to 20 carbon atoms.

[0096] Preferably, each occurrence of R6 and R7 is independently selected from: -H, -D, 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, phenyl, thiophene, or a group formed by a combination of the above groups.

[0097] Furthermore, each time R6 and R7 appear, they are independently selected from: -H, a straight-chain or branched alkyl group having 11-16 carbon atoms, a straight-chain or branched alkoxy group having 11-16 carbon atoms, a straight-chain or branched alkylthio group having 11-16 carbon atoms, a phenyl group substituted with a straight-chain or branched alkyl group having 6-16 carbon atoms, or a thiophene group substituted with a straight-chain or branched alkyl group having 6-16 carbon atoms.

[0098] Preferred, R 15 Each occurrence is independently selected from -H, -D, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, -Cl, -Br, -F, and -I.

[0099] Preferred, R 16 Each occurrence is independently selected from straight-chain alkyl groups having 1-12 carbon atoms, or from branched-chain alkyl groups having 3-12 carbon atoms.

[0100] In one embodiment, Ar3 is selected from any of the following structures:

[0101]

[0102] in,

[0103] Each time V appears, it is independently selected from CR. 17 Or N;

[0104] Each time Z appears, it is independently selected from: O, S, Se, CR 18 R 19 ;

[0105] R 17 R 18 R 19 Each occurrence is independently selected from -H, -D, straight-chain alkyl groups having 1 to 30 carbon atoms, straight-chain alkoxy groups having 1 to 30 carbon atoms, straight-chain alkathio groups having 1 to 30 carbon atoms, branched or cyclic alkyl groups having 3 to 30 carbon atoms, branched or cyclic alkoxy groups having 3 to 30 carbon atoms, branched or cyclic alkathio groups having 3 to 30 carbon atoms, alkoxycarbonyl groups having 2 to 30 carbon atoms, cyano, nitro, -Cl, -Br, -F, -I, aromatic groups having 6 to 10 ring atoms, or heteroaromatic groups having 5 to 10 ring atoms, or groups formed by combinations of the above groups;

[0106] #The meaning is the same as described above.

[0107] Preferably, Ar3 is selected from any of the following structures:

[0108]

[0109] In one embodiment, (A-2) is selected from the following structures:

[0110]

[0111] Preferably, each occurrence of R8 and R9 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy 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, -Cl, -Br, -F, -I, an aromatic group having 6 to 10 cyclic atoms, or a group formed by a combination of an aromatic group having 6 to 10 cyclic atoms and a straight-chain alkyl group having 1 to 20 carbon atoms.

[0112] Preferably, R 10 R 11Each occurrence is independently selected from -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy 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, -Cl, -Br, -F, -I, aromatic groups having 6 to 10 cyclic atoms, or groups formed by a combination of aromatic groups having 6 to 10 cyclic atoms and straight-chain alkyl groups having 1 to 20 carbon atoms.

[0113] Preferred, R 12 Each occurrence is independently selected from -H, -D, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms.

[0114] Preferred, R 13 R 14 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 10 cyclic atoms, or a group formed by a combination of an aromatic group having 6 to 10 cyclic atoms and a straight-chain alkyl group having 1 to 20 carbon atoms. More preferably, R 13 R 14 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a phenyl group, or a group formed by a combination of a phenyl group and a straight-chain alkyl group having 1 to 20 carbon atoms, or a group formed by a combination of a phenyl group and a branched alkyl group having 3 to 20 carbon atoms.

[0115] Preferred, R 17 R 18 R 19 Each occurrence is independently selected from -H, -D, straight-chain alkyl with 1 to 20 carbon atoms, branched or cyclic alkyl with 3 to 20 carbon atoms, phenyl, and phenyl substituted with a straight-chain alkyl with 1 to 20 carbon atoms or a branched or cyclic alkyl with 3 to 20 carbon atoms.

[0116] Specifically, L1 and L2 are independently selected from substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms, or substituted or unsubstituted nonaromatic ring systems having 5 to 20 ring atoms.

[0117] More specifically, L1 and L2 are independently selected from substituted or unsubstituted aromatic groups having 6 to 15 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 15 ring atoms, or substituted or unsubstituted nonaromatic ring systems having 5 to 15 ring atoms.

[0118] In one specific embodiment, L1 and L2 are independently selected from any of the following groups:

[0119]

[0120] in,

[0121] R 20 R 21 Each occurrence is independently selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 30 carbon atoms, aromatic groups having 6 to 10 cyclic atoms, heteroaromatic groups having 5 to 10 cyclic atoms, or groups formed by combinations of the above groups.

[0122] Furthermore, R 20 R 21 Each occurrence is independently selected from straight-chain alkyl groups having 1 to 10 carbon atoms or branched alkyl groups having 3 to 10 carbon atoms.

[0123] Furthermore, R 20 R 21 Selected from the same group.

[0124] In one embodiment, m is selected from 0 or 1.

[0125] In one embodiment, n is selected from 0 or 1.

[0126] In one specific embodiment, when Ar1 is selected from (A-1) or (A-2), m = n = 0.

[0127] Preferably, each occurrence of R0, R1-R4 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a cyano group, -F, -Cl, or -CF3. More preferably, R1 and R4 are independently selected from -H; R2 and R3 are independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a cyano group, -F, -Cl, or -CF3.

[0128] In one specific embodiment, the structural Choose from any of the following structures:

[0129]

[0130] In one embodiment, the structural Choose from any of the following structures:

[0131]

[0132] In this invention, the "1 to 30 atoms of straight-chain alkyl group" is selected from methyl, ethyl, propyl, butyl, and -C5H. 11 -C6H 13 -C7H15 -C8H 17 -C9H 19 -C 10 H 21 -C 11 H 23 -C 12 H 25 -C 13 H 27 -C 14 H 29 -C 15 H 31 -C 16 H 33 -C 17 H 35 -C 18 H 37 -C 19 H 38 -C 20 H 41 -C 21 H 43 -C 22 H 45 -C 23 H 47 -C 24 H 49 -C 25 H 51 -C 26 H 53 -C 27 H 55 -C 28 H 57 -C 29 H 59 -C 30 H 41 Similarly, "having 1 to 20 C straight-chain alkyl atoms", "having 1 to 15 C straight-chain alkyl atoms", and "having 1 to 10 C straight-chain alkyl atoms" have the same meaning as above.

[0133] In this invention, the structure of "having 1 to 30 C atoms in a straight-chain alkoxy group" is: -OR # , where R # Selected from straight-chain alkyl groups having 1 to 30 carbon atoms, the meaning of "having 1 to 30 carbon atoms in a straight-chain alkyl group" is the same as described in the previous paragraph. Similarly, "having 1 to 20 carbon atoms in a straight-chain alkoxy group" and "having 1 to 10 carbon atoms in a straight-chain alkoxy group" have the same meaning.

[0134] In this invention, the structure described as "having 1 to 30 C-atom straight-chain alkylthio groups" is: -SR # , where R# Selected from straight-chain alkyl groups having 1 to 30 carbon atoms, the meaning of "having 1 to 30 carbon atoms in a straight-chain alkyl group" is the same as described above. Similarly, "having 1 to 20 carbon atoms in a straight-chain alkoxide group" and "having 1 to 10 carbon atoms in a straight-chain alkoxide group" have the same meaning.

[0135] In this invention, the "alkyl group having 3 to 30 C atoms in a branched or cyclic form" includes alkyl groups having 3 C atoms in a branched or cyclic form, alkyl groups having 4 C atoms in a branched or cyclic form, alkyl groups having 5 C atoms in a branched or cyclic form, alkyl groups having 6 C atoms in a branched or cyclic form, alkyl groups having 7 C atoms in a branched or cyclic form, alkyl groups having 8 C atoms in a branched or cyclic form, alkyl groups having 9 C atoms in a branched or cyclic form, alkyl groups having 10 C atoms in a branched or cyclic form, alkyl groups having 11 C atoms in a branched or cyclic form, alkyl groups having 12 C atoms in a branched or cyclic form, alkyl groups having 13 C atoms in a branched or cyclic form, alkyl groups having 14 C atoms in a branched or cyclic form, alkyl groups having 15 C atoms in a branched or cyclic form, and alkyl groups having 16 C atoms in a branched or cyclic form. Alkyl groups with branched or cyclic carbon atoms, alkyl groups with 17 carbon atoms, alkyl groups with 18 carbon atoms, alkyl groups with 19 carbon atoms, alkyl groups with 20 carbon atoms, alkyl groups with 21 carbon atoms, alkyl groups with 22 carbon atoms, alkyl groups with 23 carbon atoms, alkyl groups with 24 carbon atoms, alkyl groups with 25 carbon atoms, alkyl groups with 26 carbon atoms, alkyl groups with 27 carbon atoms, alkyl groups with 28 carbon atoms, alkyl groups with 29 carbon atoms, and alkyl groups with 30 carbon atoms. Similarly, "alkyl group with 3 to 20 C atoms in a branched or cyclic structure", "alkyl group with 3 to 15 C atoms in a branched or cyclic structure", and "alkyl group with 3 to 10 C atoms in a branched or cyclic structure" have the same meaning.

[0136] In this invention, the structure "having 3 to 30 C atoms branched or cyclic alkoxy groups" is -O-R', where R' is selected from alkyl groups having 1 to 30 C atoms branched or cyclic alkoxy groups. The meaning of "having 3 to 30 C atoms branched or cyclic alkoxy groups" is the same as described above. Similarly, "having 3 to 20 C atoms branched or cyclic alkoxy groups," "having 3 to 15 C atoms branched or cyclic alkoxy groups," and "having 3 to 10 C atoms branched or cyclic alkoxy groups" have the same expressive meaning.

[0137] In this invention, "having 3 to 30 C-atom branched or cyclic alkylthio groups" is selected from -SR, and "R" is selected from having 1 to 30 C-atom branched or cyclic alkyl groups. The meaning of "having 3 to 30 C-atom branched or cyclic alkyl groups" is the same as described above. Similarly, "having 3 to 20 C-atom branched or cyclic alkylthio groups," "having 3 to 15 C-atom branched or cyclic alkylthio groups," and "having 3 to 10 C-atom branched or cyclic alkylthio groups" have the same expressive meaning.

[0138] In a more specific embodiment, structural formula (II) is selected from the following structures:

[0139]

[0140]

[0141]

[0142]

[0143] In one specific embodiment, the Selected from (C-1) or (C-2):

[0144]

[0145] In one specific embodiment, the Selected from (C-3):

[0146] In one specific embodiment, the Selected from (C-4):

[0147] Furthermore, A1, A2, and A3 are selected from the same group.

[0148] As an example, the non-fullerene acceptor compound provided by the present invention can be selected from those having the following structure:

[0149] Selected from any structure of (H-1)-(H-6), A1, A2, and A3 are selected from the same group, and A1, A2, and A3 are selected from any structure of (B-1)-(B-18), (B-25)-(B-33), (B-40)-(B-60), (B-64)-(B-71), (B-73)-(B-74), (B-76)-(B-80), and (B-82)-(B-87); Selected from (C-1).

[0150] or Selected from any structure of (H-7)-(H-12), A1, A2, and A3 are selected from the same group, and those with the same A1, A2, and A3 are selected from any structure of (B-1)-(B-18), (B-25)-(B-33), (B-40)-(B-60), (B-64)-(B-71), (B-73)-(B-74), (B-76)-(B-80), and (B-82)-(B-87); wherein: Selected from (C-1).

[0151] or Selected from any structure of (H-1)-(H-6), A1, A2, and A3 are selected from the same group, and those with the same A1, A2, and A3 are selected from any structure of (B-1)-(B-18), (B-25)-(B-33), (B-40)-(B-60), (B-64)-(B-71), (B-73)-(B-74), (B-76)-(B-80), and (B-82)-(B-87); wherein: Selected from (C-2).

[0152] or Selected from any structure of (H-7)-(H-12), A1, A2, and A3 are selected from the same group, and those with the same A1, A2, and A3 are selected from any structure of (B-1)-(B-18), (B-25)-(B-33), (B-40)-(B-60), (B-64)-(B-71), (B-73)-(B-74), (B-76)-(B-80), and (B-82)-(B-87); wherein: Selected from (C-2).

[0153] or Selected from any structure of (H-1)-(H-6), A1, A2, and A3 are selected from the same group, and those with the same A1, A2, and A3 are selected from any structure of (B-19)-(B-21), (B-34)-(B-36), (B-61)-(B-62), (B-72), and (B-75); wherein: Selected from (C-3).

[0154] or Selected from any structure of (H-7)-(H-12), A1, A2, and A3 are selected from the same group, and those with the same A1, A2, and A3 are selected from any structure of (B-19)-(B-21), (B-34)-(B-36), (B-61)-(B-62), (B-72), and (B-75); wherein: Selected from (C-3).

[0155] or Selected from any structure of (H-1)-(H-6), A1, A2, and A3 are selected from the same group, and those with the same A1, A2, and A3 are selected from any structure of (B-22)-(B-24), (B-37)-(B-39), (B-63), and (B-81); wherein: Selected from (C-4).

[0156] The non-fullerene acceptor compound described in this invention can be used as an active layer acceptor material in organic solar cell devices.

[0157] The present invention also relates to a mixture comprising at least one of the aforementioned non-fullerene acceptor materials and at least one other organic functional material, wherein the at least one other organic functional material may be selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material. The weight ratio of the organic functional material to the other acceptor material is from 1:99 to 99:1. In one embodiment, the photoactive layer comprises a donor material and an acceptor material, with a weight ratio of donor material / acceptor material of 1 / 1 to 1 / 1.5.

[0158] In one embodiment, the other organic functional material is selected from active layer donor materials or active layer acceptor materials.

[0159] This application further relates to an electron acceptor material, wherein the electron acceptor material is selected from the non-fullerene acceptor compounds or mixtures described above; when the electron acceptor material is selected from a mixture, the organic mixture is selected from at least one of the non-fullerene acceptor compounds described above and at least another active layer acceptor material.

[0160] This application also relates to a composition comprising at least one non-fullerene acceptor material or mixture 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. The organic solvent may be 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 mixtures thereof. In a preferred embodiment, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto. The aforementioned organic solvent can be evaporated from the solvent system to form a thin film comprising the organic compound.

[0161] In one specific embodiment, the organic solvent is selected from chlorobenzene.

[0162] In specific embodiments, the composition may be a solution or a suspension. The solution or suspension may further include additives for adjusting viscosity, modifying film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives.

[0163] This application also provides a composition for use as a coating or printing ink in the preparation of organic electronic devices. The composition is used to prepare organic electronic devices by a printing or coating method. The printing or coating method can be selected from inkjet printing, gravure printing, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot extrusion coating, etc. Slot coating, spin coating, or inkjet printing are preferred.

[0164] This application further relates to the application of a non-fullerene acceptor compound or mixture or composition as described above in an organic electronic device. The organic electronic device may be, but is not limited to, organic solar cells (OPVs), organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic lasers, organic photodetectors (OPDs), and organic plasmon emitting diodes, with OPVs being particularly preferred.

[0165] The aforementioned organic electronic device includes at least one functional layer, wherein the functional layer contains the aforementioned non-fullerene acceptor material or a mixture thereof, or is prepared from the aforementioned composition. Preferably, the functional layer is selected from photoactive layers.

[0166] In one embodiment, the organic electronic device includes at least a first electrode, a second electrode, and one or more functional layers located between the first and second electrodes. The one or more functional layers include at least an active layer; furthermore, the one or more functional layers may be selected from an anode buffer layer, an active layer, and a cathode buffer layer to achieve better device performance.

[0167] It should be noted that, in order to improve the performance of organic solar cell devices, the functional layer may further include other functional layers, including but not limited to charge injection layer and / or charge blocking layer.

[0168] Furthermore, the organic solar cell also includes a substrate. The substrate may be disposed at the bottom of the first electrode and on a different side from the functional layer.

[0169] In an organic solar cell, the first electrode is the anode and the second electrode is the cathode; or the first electrode is the cathode and the second electrode is the anode.

[0170] The substrate can be one with excellent transparency, smooth surface, ease of handling, and water resistance. Specifically, glass substrates, thin-film glass substrates, or transparent plastic substrates can be used. Plastic substrates may include, but are not limited to, single-layer or multi-layer films such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), and polyimide (PI), and substrates commonly used in organic solar cells may also be used.

[0171] At least one of the first and second electrodes is transparent or translucent to allow light to enter. The materials used to prepare the electrodes can be selected from metals, such as vanadium (V), chromium (Cr), zinc (Zn), silver (Ag), aluminum (Al), platinum (Pt), tungsten (W), copper (Cu), molybdenum (Mo), gold (Au), nickel (Ni), palladium (Pd), or alloys of the above metals; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO∶Al or SnO2∶Sb; and conductive polymers, such as poly[3,4-(ethylene-1,2-dioxothiophene)](PEDOT), polypyrrole, and polyaniline; or materials with multilayer structures, such as LiF / Al, LiO2 / Al, LiF / Ag, MoO3 / Al / MoO3, MoO3 / Ag / MoO3, ITO / Ag / ITO, Al∶Li, Al∶BaF2, and Al∶BaF2∶Ba, but are not limited to these. The active layer includes electron donor materials and electron acceptor materials. In this specification, active layer material may refer to electron donor material and electron acceptor material.

[0172] Specifically, the electron donor material can be a variety of polymer materials or small molecule materials. Polymer materials can be selected from polythiophene material systems, such as P3AT, P3HT, P3OT, P3DDT, etc.; fluorene-containing polymer material systems, such as PF8BT, etc.; novel narrow-bandgap polymer material systems, such as copolymers of benzothiadiazoles (BT, BBT), quinoxalines (QU, PQ), pyrazines (TP, PQ), and electron-rich groups (such as thiophene derivatives), such as PCDTBT, PCPDTBT, PFO-DBT, PTB7, PBDB-T, PM6, PM7, J52, PTQ10, PTQ11, etc. Small molecule materials can be selected from one or more of the following: BT-2F, BIHTR, etc.

[0173] The photoactive layer can be formed by dissolving a photoactive material, such as an electron donor and / or an electron acceptor, in an organic solvent, and then coating the resulting solution by methods such as spin coating, dip coating, screen printing, gravure printing, spraying, doctor blade coating, slot coating, and inkjet printing, but not limited thereto.

[0174] The anode buffer layer material can be selected from poly(styrene sulfonic acid) PEDOT:PSS (poly(3,4-ethylenedioxythiophene)), molybdenum oxide (MoOx), vanadium oxide (V2O5), nickel oxide (NiO), tungsten oxide (WO4), etc. x Preferably, x is selected from 2 or 3, etc., but not limited to this.

[0175] The cathode buffer layer material can be an electron-withdrawing metal oxide or polymer. The metal oxide can be a metal complex containing 8-hydroxyquinoline, a complex containing Alq3, a metal complex containing Liq, LiF, Ca, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs2CO3), PEI-Zn, etc., and the polymer can be PFN-Br or PFN, etc., but is not limited to these.

[0176] This invention also relates to the application of organic solar cells according to the invention in various devices, including, but not limited to, building-integrated photovoltaics (BIPV), electronic shelf labels, indoor photovoltaics, the Internet of Things, smart agriculture, etc.

[0177] The present invention will now be described with reference to preferred embodiments, but the present invention is not limited to the following embodiments.

[0178] Compound preparation

[0179] Example 1: Synthesis of Compound 1

[0180]

[0181]

[0182] Synthesis of compounds 1-3:

[0183] Accurately weigh compound 1-1 (2.1 g, 6.5 mmol), compound 1-2 (7.1 g, 21.5 mmol), and tetrakis(triphenylphosphine)palladium (450 mg, 0.39 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. The mixture was purged with nitrogen three times, and then heated to reflux for 20 h. After cooling, the reaction mixture was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the mixture was separated by silica gel column chromatography using petroleum ether (PE) as eluent to give approximately 3.1 g of compound 1-3, in 84% yield. MS: 576.85.

[0184] Synthesis of compounds 1-4:

[0185] Compounds 1-3 (2.6 g, 4.5 mmol) were accurately weighed and added to a 100 mL three-necked flask. 30 mL of anhydrous tetrahydrofuran was added, and the mixture was purged with nitrogen three times, stirring thoroughly to dissolve. The mixture was then cooled to -70 °C, and n-butyllithium (n-BuLi) (2.5 M, 5.5 mL, 13.5 mmol) was slowly added dropwise. The mixture was then stirred at -50 °C for 2 hours, followed by a second cooling to -70 °C. Under these conditions, trimethyltin chloride (1.0 M, 14.9 mL, 14.9 mmol) was added in a single batch, followed by stirring for another hour. Finally, the solution was brought to room temperature and stirred overnight. The resulting mixture was poured into water and extracted with thionyl chloride (DCM). The solution was then concentrated and dried, and recrystallized from isopropanol to give approximately 2.4 g of compounds 1-4, in 52% yield. MS: 1065.43.

[0186] Synthesis of compounds 1-8:

[0187] Compounds 1-5 (8.2 g, 8 mmol), 1-6 (2.2 g, 9.6 mmol), and 1-7 (2.6 g, 9.6 mmol) were accurately weighed and added to a 500 mL three-necked flask. 350 mL of chloroform was added, and the mixture was purged with nitrogen three times. The mixture was stirred under reflux for 12 h. The reaction was cooled to room temperature and extracted with DCM. The crude product was purified by silica gel column chromatography using DCM:PE = 1:1 (volume ratio) as the eluent to obtain approximately 5.1 g of compounds 1-8, with a yield of 43%. MALDI-TOF-MS: 1494.62.

[0188] Synthesis of Compound 1:

[0189] Accurately weigh compounds 1-4 (1.07 g, 1 mmol), compounds 1-8 (4.9 g, 3.3 mmol), and tetrakis(triphenylphosphine)palladium (104 mg, 0.09 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 10:1 (v / v) as eluent to obtain approximately 2 g of compound 1, with a yield of 41%. MALDI-TOF-MS: 4818.98.

[0190] Example 2: Synthesis of Compound 2

[0191]

[0192] Synthesis of compound 2-2:

[0193] Accurately weigh compound 1-1 (2.1 g, 6.5 mmol), compound 2-1 (8.4 g, 21.5 mmol), and tetrakis(triphenylphosphine)palladium (450 mg, 0.39 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE as the eluent to obtain approximately 2.1 g of compound 2-2, in 85% yield. MS: 378.48.

[0194] Synthesis of compounds 2-3:

[0195] Compound 2-2 (1.7 g, 4.5 mmol) was accurately weighed and added to a 100 mL three-necked flask. 30 mL of anhydrous tetrahydrofuran was added, and the mixture was purged with nitrogen three times, stirring thoroughly to dissolve. The mixture was then cooled to -70 °C, and n-BuLi (2.5 M, 5.5 mL, 13.5 mmol) was slowly added dropwise. The mixture was then stirred at -50 °C for 2 hours, followed by a second cooling to -70 °C. Under these conditions, trimethyltin chloride (1.0 M, 14.9 mL, 14.9 mmol) was added in a single addition, followed by stirring for another hour. Finally, the solution was brought to room temperature and stirred overnight. The resulting mixture was poured into water and extracted with DCM. The solution was then concentrated and dried, and recrystallized from isopropanol to give approximately 2 g of compound 2-3, in 52% yield. MS: 866.98.

[0196] Synthesis of compounds 2-5:

[0197] Compounds 2-4 (8.4 g, 8 mmol), 1-6 (2.2 g, 9.6 mmol), 1-7 (2.6 g, 9.6 mmol), and 20 mL of pyridine were added to a 500 mL three-necked flask. 350 mL of chloroform was added, and the mixture was purged with nitrogen three times. The mixture was stirred under reflux for 12 h. The reaction was cooled to room temperature, extracted with DCM, and the crude product was purified by silica gel column chromatography using DCM:PE = 5:1 (v / v) as the eluent to give approximately 5.3 g of compound 2-5, with a yield of 44%. MALDI-TOF-MS: 1516.90.

[0198] Synthesis of compound 2:

[0199] Accurately weigh compounds 2-3 (0.87 g, 1 mmol), 2-5 (5 g, 3.3 mmol), and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, heat the entire reaction system to reflux and react for 20 h. After cooling, the reaction solution is poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent is removed by rotary evaporation of the organic phase, and the solution is separated by silica gel column chromatography using PE:EA = 5:1 (v / v) as eluent to obtain approximately 2.5 g of compound 2, with a yield of 54%. MALDI-TOF-MS: 4686.57.

[0200] Example 3: Synthesis of Compound 3

[0201]

[0202]

[0203] Synthesis of compound 3-2:

[0204] Accurately weigh compound 1-1 (2.1 g, 6.5 mmol), compound 3-1 (8.8 g, 21.5 mmol), and tetrakis(triphenylphosphine)palladium (150 mg, 0.13 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA. Finally, the solution was concentrated and dried, and recrystallized from isopropanol to give approximately 3.9 g of compound 3-2, with a yield of 74%. MS: 813.01.

[0205] Synthesis of compounds 3-5:

[0206] Compounds 3-3 (8.6 g, 8 mmol), 3-4 (2.5 g, 9.6 mmol), 1-7 (2.6 g, 9.6 mmol), and 20 mL of pyridine were added to a 500 mL three-necked flask. 350 mL of chloroform was added, and the mixture was purged with nitrogen three times. The mixture was stirred under reflux for 12 h. The reaction was cooled to room temperature, extracted with DCM, and the crude product was purified by silica gel column chromatography using DCM:PE = 5:1 (v / v) as the eluent. Approximately 5.2 g of compound 3-5 was obtained, with a yield of 41%. MALDI-TOF-MS: 1575.81.

[0207] Synthesis of compound 3:

[0208] Accurately weigh compound 3-2 (0.8 g, 1 mmol), compound 3-5 (5.2 g, 3.3 mmol), and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 10:1 (v / v) as eluent to give approximately 2.9 g of compound 3, with a yield of 61%. MALDI-TOF-MS: 4809.26.

[0209] Example 4: Synthesis of Compound 4

[0210]

[0211]

[0212] Synthesis of compound 4-3:

[0213] Accurately weigh compound 4-1 (7.8 g, 8 mmol), compound 4-2 (2.5 g, 9.6 mmol), and compound 1-7 (2.6 g, 9.6 mmol), and add 20 mL of pyridine to a 500 mL three-necked flask. Add 350 mL of chloroform, purge with nitrogen three times, and stir under reflux for 12 h. Cool the reaction to room temperature, extract with DCM, and purify the crude product by silica gel column chromatography using DCM:PE = 10:1 (v / v) as the eluent to obtain approximately 4.35 g of compound 4-3, with a yield of 37%. MALDI-TOF-MS: 1470.55.

[0214] Synthesis of compound 4:

[0215] Accurately weigh compounds 1-4 (0.85 g, 0.8 mmol), compounds 4-3 (3.8 g, 2.6 mmol), and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 10:1 (v / v) as eluent to obtain approximately 1.9 g of compound 4, with a yield of 51%. MALDI-TOF-MS: 4746.82.

[0216] Example 5: Synthesis of Compound 5

[0217]

[0218]

[0219] Synthesis of compound 5-3:

[0220] Accurately weigh 5-1 (1.8 g, 10 mmol), 5-2 (2.5 g, 10 mmol), sodium tert-butoxide (1.9 g, 20 mmol), bis(dibenzylacetone)palladium Pd(dba)2 (113 mg, 0.2 mmol), and 1,1'-bis(diphenylphosphine)ferrocene (221 mg, 0.4 mmol) into a 50 mL three-necked flask. Add 30 mL of anhydrous toluene, purge with nitrogen three times, heat to reflux, and react for 12 h. After cooling, the reaction solution is poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase, using PE as eluent, and separate by silica gel column chromatography to obtain approximately 3.2 g of compound 5-3, yield 92%. MS: 349.49.

[0221] Synthesis of compound 5-4:

[0222] Accurately weigh 5-3 (2.8 g, 8 mmol), 5-2 (2.0 g, 8 mmol), sodium tert-butoxide (1.5 g, 16 mmol), Pd(dba)2 (90 mg, 0.16 mmol), and tri-tert-butylphosphine (65 mg, 0.32 mmol) into a 100 mL three-necked flask. Add 30 mL of anhydrous toluene, purge with nitrogen three times, heat to reflux, and react for 12 h. After cooling, the reaction solution is poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase, using PE as eluent, and separate by silica gel column chromatography to obtain approximately 3.1 g of compound 5-4, in 75% yield. MS: 515.87.

[0223] Synthesis of compound 5-5:

[0224] Compound 5-4 (2.3 g, 4.5 mmol) was added to a 100 mL three-necked flask, followed by the addition of 30 mL of anhydrous tetrahydrofuran. The mixture was then purged with nitrogen three times and stirred thoroughly to dissolve. The mixture was then cooled to -70 °C, and n-BuLi (2.5 M, 5.5 mL, 13.5 mmol) was slowly added dropwise. The mixture was stirred at -50 °C for 2 hours, then cooled again to -70 °C, under which trimethyltin chloride (1.0 M, 14.9 mL, 14.9 mmol) was added in a single dose, followed by stirring for another hour. The solution was then brought to room temperature and stirred overnight. The resulting mixture was poured into water and extracted with DCM. The solution was finally concentrated and dried, and recrystallized from isopropanol to give approximately 2.3 g of compound 5-5 in 52% yield. MS: 1004.43.

[0225] Synthesis of compounds 5-9:

[0226] Compounds 5-6 (10.8 g, 10 mmol), 5-7 (2.2 g, 12 mmol), 5-8 (2.7 g, 12 mmol), and pyridine (20 mL) were added to a 500 mL three-necked flask. 350 mL of chloroform was added, and the mixture was purged with nitrogen three times. The mixture was stirred under reflux for 12 h. The reaction was cooled to room temperature, extracted with DCM, and the crude product was purified by silica gel column chromatography using DCM:PE = 1:1 as the eluent. Approximately 4.9 g of compound 5-9 was obtained, with a yield of 34%. MALDI-TOF-MS: 1454.41.

[0227] Synthesis of compound 5:

[0228] Accurately weigh compound 5-5 (1 g, 1 mmol), compound 5-9 (4.8 g, 3.3 mmol), and tetra(triphenylphosphine)palladium (69 mg, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 30:1 (v / v) as eluent to obtain approximately 2.9 g of compound 5, with a yield of 63%. MALDI-TOF-MS: 4638.37.

[0229] Example 6: Synthesis of Compound 6

[0230]

[0231] Synthesis of compound 6-2:

[0232] Compound 6-1 (10.3 g, 10 mmol), compound 1-6 (2.76 g, 12 mmol), compound 1-7 (3.27 g, 12 mmol), and 20 mL of pyridine were added to a 500 mL three-necked flask. 350 mL of chloroform was added, and the mixture was purged with nitrogen three times. The mixture was stirred under reflux for 12 h. The reaction was cooled to room temperature, extracted with DCM, and the crude product was purified by silica gel column chromatography using DCM:PE = 5:1 (v / v) as the eluent to give approximately 5.4 g of compound 6-2, with a yield of 36%. MS: 1496.89.

[0233] Synthesis of compound 6:

[0234] Accurately weigh compound 5-5 (1.0 g, 1 mmol), compound 6-2 (4.9 g, 3.3 mmol), and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 10:1 (v / v) as eluent to obtain approximately 2.7 g of compound 6, with a yield of 56%. MALDI-TOF-MS: 4763.70.

[0235] Example 7: Synthesis of Compound 7

[0236]

[0237] Synthesis of compound 7-2:

[0238] Compound 7-1 (8.9 g, 8 mmol), compound 1-6 (2.2 g, 9.6 mmol), compound 1-7 (2.6 g, 9.6 mmol), and 20 mL of pyridine were added to a 500 mL three-necked flask. 350 mL of chloroform was added, and the mixture was purged with nitrogen three times. The mixture was stirred under reflux for 12 h. The reaction was cooled to room temperature, extracted with DCM, and the crude product was purified by silica gel column chromatography using DCM:PE = 15:1 (v / v) as the eluent. Approximately 5.3 g of compound 7-2 was obtained, with a yield of 42%. MALDI-TOF-MS: 1574.58.

[0239] Synthesis of compound 7:

[0240] Accurately weigh compound 5-5 (1.0 g, 1 mmol), compound 7-2 (5.2 g, 3.3 mmol), and tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 15:1 (v / v) as eluent to give approximately 3.1 g of compound 7, in a yield of 63%. MALDI-TOF-MS: 4998.22.

[0241] Example 8: Synthesis of Compound 8

[0242]

[0243] Synthesis of compound 8:

[0244] Accurately weigh compounds 3-2 (0.8 g, 1 mmol), 1-8 (4.9 g, 3.3 mmol), and tetrakis(triphenylphosphine)palladium (104 mg, 0.09 mmol) and add them sequentially to a 100 mL three-necked flask, followed by 30 mL of anhydrous toluene. After purging with nitrogen three times, the entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was separated by silica gel column chromatography using PE:EA = 10:1 (v / v) as eluent to give approximately 2.2 g of compound 8, with a yield of 48%. MALDI-TOF-MS: 4566.39.

[0245] Fabrication and characterization of OPV devices

[0246] The fabrication process of the OPV device comprising the above-described compound is described in detail below through specific embodiments. Figure 1 As shown, the OPV device structure is as follows: Indium Tin Oxide (ITO) / PEDOT:PSS / Active Layer / PFN-Br / Ag

[0247] The fabrication steps of device example 1 are as follows:

[0248] 1) ITO substrate cleaning

[0249] The ITO conductive glass anode layer was cleaned, followed by ultrasonic cleaning with deionized water, acetone, and isopropanol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode power function.

[0250] 2) Preparation of the anode buffer layer 103

[0251] PEDOT:PSS was uniformly spin-coated onto ITO in air at a speed of 3000-4000 rpm and dried at 150°C for 15 min to obtain an anodized modification layer with a thickness of 20 nm.

[0252] 3) Preparation of photoactive layer 104

[0253] In a glove box (inert gas atmosphere), the photoactive layer material is uniformly spin-coated onto the anode buffer layer at a rotation speed of 1800-4000 rpm to obtain an active material layer with a thickness of 100 nm; wherein the donor material in the photoactive layer material is selected from PM6 and D18, with a PM6:D18 mass ratio of 0.8:0.2; the acceptor material is selected from compound 1, with a PM6:D18:compound 1 mass ratio of 0.8:0.2:1.2.

[0254] 4) Preparation of cathode buffer layer 105

[0255] After hot annealing at 100℃ for 10 min, the cathode buffer layer material PFN-Br was uniformly spin-coated onto the active layer at a spin speed of 1800-4000 rpm to obtain a cathode buffer layer with a thickness of 5 nm.

[0256] 5) Preparation of cathode layer 106

[0257] In high vacuum (1×10 -6 Ag is deposited onto the cathode buffer layer in millibars to form a cathode layer with a thickness of 100 nm.

[0258] 6) Packaging

[0259] The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0260] Device Example 2: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 2.

[0261] Device Example 3: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 3.

[0262] Device Example 4: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 4.

[0263] Device Example 5: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 5.

[0264] Device Example 6: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 6.

[0265] Device Example 7: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 7.

[0266] Device Example 8: The preparation method is the same as that of Device Example 1, except that the acceptor material compound 1 is replaced with compound 8.

[0267] 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 as shown in Table 1.

[0268] Table 1

[0269] Device Examples receptor materials Photoelectric conversion efficiency (%) Device Example 1 Compound 1 16.68 Device Example 2 Compound 2 15.31 Device Example 3 Compound 3 15.05 Device Example 4 Compound 4 13.21 Device Example 5 Compound 5 12.96 Device Example 6 Compound 6 11.14 Device Example 7 Compound 7 14.73 Device Example 8 Compound 8 15.62

[0270] As can be seen from the data in Table 1, when the oligomeric non-fullerene acceptor material described in this invention is used as an acceptor material in organic solar cell devices, it exhibits high photoelectric conversion efficiency.

[0271] A comparison between Device Example 1 and Device Example 8 shows that Device Example 1 has a 6.7% higher photoelectric effect than Device Example 8. This is because the thiophene linking group in Compound 1 is replaced by an alkyl group, which adjusts the solubility and intermolecular aggregation properties of the compound, thus giving the compound better photoelectric performance.

[0272] 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 non-fullerene acceptor compound, characterized by: having the structure of Formula (I-1) or Formula (I-2): wherein, A1, A2, A3are independently selected from Formula (II), M is independently selected at each occurrence from O or C(CN)2; R0, R1, R2, R3, R4are independently selected at each occurrence from -H, -D, a linear alkyl group having 1 to 6 C atoms, a branched alkyl group having 3 to 6 C atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the aforementioned groups; R5is independently selected at each occurrence from -H, -D, a linear alkyl group having 1 to 15 C atoms, a branched alkyl group having 3 to 15 C atoms, a cyano group, a nitro group, -Cl, -Br, -F, -I, or a group formed by a combination of the aforementioned groups; Ar1is independently selected at each occurrence from any of the structures of (A-1), (A-2), (A-3), (A-4), wherein the structures of (A-3), (A-4) are as follows: (A-1) is selected from the following structures: (A-2) is selected from the following structures: W is independently selected at each occurrence from O, S, Se, NR 12 ; R6, R7are independently selected at each occurrence from -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear alkylthio group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms, a branched or cyclic alkylthio group having 3 to 20 C atoms, a phenyl group, a thienyl group, or a group formed by a combination of the aforementioned groups; R8, R9are independently selected at each occurrence from -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms; R 10 , R 11 each occurrence is independently selected from -H, -D, -Ci, -Br, -F or -I; R 12 each occurrence independently selected from linear alkyl having 1 to 30 C atoms, or branched alkyl having 3 to 30 C atoms; R 13 , R 14 each occurrence independently is selected from -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, phenyl, or a group formed by combining phenyl with a straight-chain alkyl group having 1 to 20 C atoms, or a group formed by combining phenyl with a branched alkyl group having 3 to 20 C atoms; R 15 each occurrence independently is selected from the group consisting of -H, -D, a straight-chain alkyl group having from 1 to 20 C atoms, a branched or cyclic alkyl group having from 3 to 20 C atoms, -Cl, -Br, -F, -I; R 18 , R 19 each occurrence independently is selected from the group consisting of -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, phenyl, phenyl substituted by a straight-chain alkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms; L1, L2are independently selected from any of the following groups: R 20 , R 21 each occurrence is independently selected from a linear alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 30 C atoms; m is selected from 0 or 1; n is selected from 0 or 1; m = n = 0 when Ar1is selected from (A-1) or (A-2); * denotes the point of attachment.

2. The non-fullerene acceptor compound according to claim 1, characterized in that: in each occurrence, is selected from wherein R5is, in each occurrence, independently selected from a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, cyano, nitro, -CI, -Br, -F, -I, or -CF3.

3. The non-fullerene acceptor compound according to claim 1, characterized in that: the selected from any one of the following structures: and / or said selected from the following structures:

4. The non-fullerene acceptor compound of claim 1, wherein: R 20 , R 21 each occurrence is independently selected from a linear alkyl group having 1 to 10 C atoms, or a branched or cyclic alkyl group having 3 to 10 C atoms.

5. The non-fullerene acceptor compound according to claim 1, characterized in that: in general formula (II) is selected from any one of the following structures: and / or selected from any one of the following structures:

6. The non-fullerene acceptor compound according to claim 1, characterized in that: Formula (II) is selected from the following structures:

7. A mixture characterized in that: The mixture comprises the non-fullerene acceptor compound according to any one of claims 1 to 6 and at least one organic functional material selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material.

8. An organic electronic device comprising at least one functional layer, characterized in that: The functional layer material is selected from the non-fullerene acceptor compound according to any one of claims 1 to 6 or the mixture according to claim 7.

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