Organic compound containing cyano-substituted 1, 3-indandione and application

Abstract

The invention relates to the field of organic photovoltaic cell materials, in particular to an organic compound containing cyano-substituted 1, 3-indandione. The organic compound containing cyano-substituted 1, 3-indandione provided by the invention is used as an acceptor material to be matched with a proper donor material to be applied to an organic photovoltaic cell, and the photoelectric property of the organic photovoltaic cell can be improved.

Description

Technical Field

[0001] The invention relates to the field of organic photovoltaic cell materials, in particular to an organic compound containing cyano-substituted 1,3-indandione. Background Art

[0002] Organic photovoltaic cells (OPV) have many advantages such as light weight, flexibility, semi-transparency, and suitability for solution printing processes, and have broad application prospects in portable energy supply in multiple scenarios. In recent years, with the continuous research on new material synthesis, active layer morphology regulation, interface engineering, and device structure, organic photovoltaic cells based on non-fullerene acceptors have achieved significant improvements in photoelectric conversion efficiency (PCE), which has now exceeded 20%, attracting widespread attention.

[0003] Organic photovoltaic cells are generally prepared by coating a blended solution of donor and acceptor materials. The optimal performance of organic photovoltaic cells is closely related to the morphology of the bulk heterojunction (BHJ) photoactive layer and is affected by factors such as molecular stacking, domain purity and domain size. In addition, device performance is also heavily dependent on vertical phase separation within the active layer. Ideally, donors and acceptors should be separated near the anode and cathode, respectively, to achieve efficient hole and electron transport while minimizing charge recombination at the interface between the active layer and the electrode. Based on this, the bulk heterojunction morphology has been fine-tuned through the development of new materials and the optimization of device structure to achieve higher PCE, but the current morphology control of the active layer remains a daunting challenge.

[0004] The development of new and efficient non-fullerene acceptors is an important way to continuously improve the performance of organic photovoltaic cells. On the one hand, the currently commonly used high-performance non-fullerene acceptors have strong intermolecular interactions and high crystallinity, and are prone to excessive aggregation in organic solvents, resulting in uncontrollable morphology of the active layer. On the other hand, they face problems such as long synthesis routes and high synthesis costs, which are not conducive to the industrial preparation of organic photovoltaic cells. Therefore, the development of efficient and low-cost non-fullerene acceptor materials is very necessary for the development of organic photovoltaic cells. Summary of the invention

[0005] The purpose of the present invention is to provide a novel organic compound based on cyano-substituted 1,3-indanedione, by selecting a novel electron-withdrawing end group, optimizing the energy level and intramolecular charge transfer force of the organic compound, so that when the organic compound is used as an acceptor material in an organic photovoltaic cell, it has a higher photoelectric conversion efficiency.

[0006] The present invention provides an organic compound containing cyano-substituted 1,3-indandione, which has a structure as shown in general formula (I) or general formula (II):

[0007] (I)

[0008] (II)

[0009] in:

[0010] Each occurrence of Z is independently selected from O, S or Se;

[0011] Ar1 is selected from a substituted or unsubstituted heteroaromatic group having 5-6 ring atoms;

[0012] R1, R2, R3, R4, R5, R6 are independently selected from -H, -D, substituted or unsubstituted straight-chain alkyl having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkyl having 3-30 carbon atoms, substituted or unsubstituted straight-chain alkoxy having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkoxy having 3-30 carbon atoms, substituted or unsubstituted straight-chain alkylthio having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkylthio having 3-30 carbon atoms, substituted or unsubstituted aromatic group having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic group having 5-20 ring atoms;

[0013] The “substituted or unsubstituted” means that the defined group is not substituted or is substituted by one or more substituents R, wherein each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, cyano, nitro, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched-chain alkylthio group having 3 to 20 carbon atoms, a cyclic alkylthio group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by a combination of the above groups.

[0014] Furthermore, the present invention also relates to a mixture, which comprises the organic compound containing cyano-substituted 1,3-indandione as described above, and at least another organic functional material.

[0015] Furthermore, the present invention also relates to a composition, which comprises the organic compound or mixture containing cyano-substituted 1,3-indandione as described above, and at least one organic solvent.

[0016] Correspondingly, the present invention also relates to an organic electronic device, which comprises the organic compound or mixture of cyano-substituted 1,3-indandione as described above, or is prepared from the above composition.

[0017] Compared with the prior art, the present invention has the following advantages:

[0018] The end group of the organic compound containing cyano-substituted 1,3-indanedione provided by the present invention is selected from cyano-substituted 1,3-indanedione, and the cyano-substituted 1,3-indanedione is On the one hand, it has better planarity, thereby enhancing the π-π stacking and charge transfer between molecules; on the other hand, the synthesis route is shorter and the cost of preparing raw materials is lower. Furthermore, compared with the halogen-substituted 1,3-indanedione, the cyano-substituted 1,3-indanedione has a stronger electron-withdrawing effect than the halogen, thereby enhancing the charge transfer effect within the molecule, and further adjusting the LUMO energy level difference with the donor, thereby improving the charge dissociation efficiency. The organic compound containing cyano-substituted 1,3-indanedione provided by the present invention is used in an organic photovoltaic cell with a suitable donor material, which can improve the photoelectric performance of the organic photovoltaic cell, which is of great significance for promoting the large-scale commercialization of organic photovoltaic cells. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 It is a schematic diagram of the structure of the preparation example and comparative example of the organic photovoltaic cell device of the present invention. DETAILED DESCRIPTION

[0020] In order to make the purpose, technical solution and effect of the present application clearer and more specific, the present application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application. Based on the described embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0021] The terms "and / or", "or / and", and "and / or" used in this article include any one of two or more related listed items, and also include any and all combinations of related listed items, and the 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 that are all connected by "logical and", and undoubtedly includes technical solutions that are all connected by "logical or". For example, "A and / or B" includes three parallel solutions of 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, the technical solution that is all connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, the combination of any two or any three of A, B, C, and D, and also includes the combination of four of A, B, C, and D (that is, the technical solution that is all connected by "logical AND").

[0022] In the present invention, organic photovoltaic device, organic solar cell, OPV and OSC have the same meaning and can be interchangeable.

[0023] In the present invention, photoactive layer and active layer have the same meaning and can be interchanged.

[0024] In the present invention, when the same group contains multiple substituents with the same symbol, the substituents may be the same or different from each other. , the six Rs on the benzene ring may be the same or different from each other.

[0025] In the present invention, "substituted" means that one or more hydrogen atoms in the substituted group are replaced by a substituent.

[0026] In the present invention, the "number of ring atoms" refers to the number of atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. In an aromatic group, the number of ring atoms is the same as the number of carbon atoms; in a heteroaromatic group, the number of ring atoms is the number of carbon atoms plus the number of heteroatoms; for example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, the number of ring atoms of quinoline is 10, the number of ring atoms of a thienyl group is 5, the number of ring atoms of thienothiophene is 8, and the number of ring atoms of pyridine is 6.

[0027] In the present invention, "aromatic group" refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aromatic group can be a monocyclic aromatic group (such as phenyl) or a polycyclic aromatic group. In other words, the aromatic group can be a monocyclic aromatic group, a condensed aromatic group, two or more monocyclic aromatic groups conjugated by carbon-carbon bonds, monocyclic aromatic groups and condensed aromatic groups conjugated by carbon-carbon bonds, and two or more condensed aromatic groups conjugated by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated by carbon-carbon bonds can also be regarded as aromatic groups of the present application. Preferably, the aromatic group is selected from aromatic groups with 6-30 C atoms; further, selected from aromatic groups with 6-20 C atoms; further, selected from aromatic groups with 6-10 C atoms; aromatic groups include but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof.

[0028] In the present invention, "heteroaromatic group" refers to a monovalent heteroaromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring, and the heteroatom may be at least one of B, O, N, P, Si, Se and S. The heteroaromatic group may be a monocyclic heteroaromatic group or a polycyclic heteroaromatic group. In other words, the heteroaromatic group may be a single heteroaromatic ring system or a plurality of heteroaromatic ring systems conjugated by carbon-carbon bonds, and any heteroaromatic ring system is a heteroaromatic monocyclic ring or a heteroaromatic condensed ring. Preferably, the heteroaromatic group is selected from heteroaromatic groups having 5-30 ring atoms; further, selected from heteroaromatic groups having 5-20 ring atoms; further, selected from heteroaromatic groups having 5-10 ring atoms. Heteroaromatic groups include, but are not limited to, thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.

[0029] In the present invention, the number of carbon atoms of the linear alkyl group may be 1 to 30, 1 to 20, 1 to 16, 1 to 10, or 1 to 6. The number of carbon atoms of the branched alkyl group may be 3 to 30, 3 to 20, 3 to 16, 3 to 10, or 3 to 6. The number of carbon atoms of the cyclic alkyl group may be 3 to 30, 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Non-limiting examples of the linear alkyl group include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, -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 Non-limiting examples of branched alkyl groups include isopropyl, branched alkyl groups containing 4 C atoms, branched alkyl groups containing 5 C atoms, branched alkyl groups containing 6 C atoms, branched alkyl groups containing 7 C atoms, branched alkyl groups containing 8 C atoms, branched alkyl groups containing 9 C atoms, branched alkyl groups containing 10 C atoms, branched alkyl groups containing 11 C atoms, branched alkyl groups containing 12 C atoms, branched alkyl groups containing 13 C atoms, branched alkyl groups containing 14 C atoms, branched alkyl groups containing 15 C atoms, and branched alkyl groups containing 16 C atoms. Non-limiting examples of cyclic alkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclic alkyl groups containing 7 C atoms, cyclic alkyl groups containing 8 C atoms, cyclic alkyl groups containing 9 C atoms, cyclic alkyl groups containing 10 C atoms (such as adamantyl), cyclic alkyl groups containing 11 C atoms, cyclic alkyl groups containing 12 C atoms, cyclic alkyl groups containing 13 C atoms, cyclic alkyl groups containing 14 C atoms, cyclic alkyl groups containing 15 C atoms, and cyclic alkyl groups containing 16 C atoms.

[0030] The term "alkoxy" refers to a group with the structure "-O-alkyl", i.e., an alkyl group as defined above connected to another group via an oxygen atom. The straight-chain alkoxy group means that the alkyl group in the "-O-alkyl" is selected from a straight-chain alkyl group, wherein the carbon number of the straight-chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the branched-chain alkoxy group means that the alkyl group in the "-O-alkyl" is selected from a branched-chain alkyl group, wherein the carbon number of the branched-chain alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6.

[0031] The term "alkylthio" refers to a group having the structure "-S-alkyl", i.e., an alkyl group as defined above connected to another group via a sulfur atom. The straight-chain alkylthio group means that the alkyl group in the "-S-alkyl" is selected from a straight-chain alkyl group, wherein the carbon number of the straight-chain alkyl group may be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the branched-chain alkylthio group means that the alkyl group in the "-S-alkyl" is selected from a branched-chain alkyl group, wherein the carbon number of the branched-chain alkyl group may be 3 to 20, 3 to 16, 3 to 10, or 3 to 6.

[0032] In the present invention, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0033] In the present invention, one or more groups "independently selected from" means that when one or more groups appear simultaneously and in multiple places in a compound, they are all independently selected and may be the same or different.

[0034] In the present invention, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0035] In the process of describing the structural elements of the present invention, the words "include" or "comprises" and the like used in the present invention mean that the devices or materials appearing before the word include the devices or materials listed after the word and their equivalents, but do not exclude other devices or materials.

[0036] In the description of the present invention, it should be understood that the terms "upper", "lower", "between layers", etc. indicate orientations or positional relationships based on the orientations or positional relationships shown in the accompanying drawings, or are the orientations or positional relationships in which the organic solar cell device is conventionally placed when in use, or are the orientations or positional relationships conventionally understood by those skilled in the art. These are only for the convenience of describing the present invention and simplifying the description, and do not indicate or imply that the device or element referred to must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be understood as a limitation on the present invention.

[0037] The "combinations thereof", "any combinations thereof", "any combinations thereof", "combinations" and the like used in the present invention include all suitable combinations of any two, any three or more items in the listed groups.

[0038] In the present invention, “further”, “furthermore”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0039] In the present invention, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel solutions of "yes" or "no". If multiple "options" appear in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction, each "optional" is independent.

[0040] In the present invention, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0041] The first aspect of the present invention provides an organic compound containing a cyano-substituted 1,3-indandione, having a structure as shown in the general formula (I) or the general formula (II):

[0042] (I)

[0043] (II)

[0044] in:

[0045] Each occurrence of Z is independently selected from O, S or Se;

[0046] Ar1 is selected from a substituted or unsubstituted heteroaromatic group having 5-6 ring atoms;

[0047] R1, R2, R3, R4, R5, R6 are independently selected from -H, -D, substituted or unsubstituted straight-chain alkyl having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkyl having 3-30 carbon atoms, substituted or unsubstituted straight-chain alkoxy having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkoxy having 3-30 carbon atoms, substituted or unsubstituted straight-chain alkylthio having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkylthio having 3-30 carbon atoms, substituted or unsubstituted aromatic group having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic group having 5-20 ring atoms;

[0048] The “substituted or unsubstituted” means that the defined group is not substituted or is substituted by one or more substituents R, wherein each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, cyano, nitro, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched-chain alkylthio group having 3 to 20 carbon atoms, a cyclic alkylthio group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by a combination of the above groups.

[0049] In one embodiment, Ar1 is selected from any of the following groups:

[0050] ;

[0051] Wherein: Y is selected from O, S, Se, NR8;

[0052] R8 is selected from a linear alkyl group having 1 to 30 carbon atoms, or a branched or cyclic alkyl group having 3 to 30 carbon atoms;

[0053] R7, at each occurrence, is independently selected from -H, -D, -F, -Cl, -Br, -I, cyano, nitro, a straight-chain alkyl group having 1-20 carbon atoms, a branched-chain alkyl group having 3-20 carbon atoms, a cyclic alkyl group having 3-20 carbon atoms, a straight-chain alkoxy group having 1-20 carbon atoms, a branched-chain alkoxy group having 3-20 carbon atoms, a cyclic alkoxy group having 3-20 carbon atoms, a straight-chain alkylthio group having 1-20 carbon atoms, a branched-chain alkylthio group having 3-20 carbon atoms, a cyclic alkylthio group having 3-20 carbon atoms, an aromatic group having 6-20 carbon atoms, a heteroaromatic group having 5-20 ring atoms, or a group formed by a combination of the above groups;

[0054] # indicates a fusion site, and the fusion site selects a C atom.

[0055] In a preferred embodiment, the organic compound containing cyano-substituted 1,3-indandione has a structure as shown in any one of the general formulas (III-1) to (III-4):

[0056] .

[0057] Furthermore, the R8 is selected from a straight chain alkyl group having 1 to 20 carbon atoms, or a branched chain alkyl group having 3 to 20 carbon atoms.

[0058] Furthermore, the R8 is selected from a straight-chain alkyl group having 1 to 12 carbon atoms and a branched-chain alkyl group having 3 to 12 carbon atoms.

[0059] Preferably, the R8 is selected from the following groups:

[0060]

[0061] Wherein: * indicates the connection site.

[0062] Further, each occurrence of R7 is independently selected from -H, -D, -F, -Cl, -Br, -I, cyano, nitro, a straight-chain alkyl group having 1-20 carbon atoms, a branched-chain alkyl group having 3-20 carbon atoms, a cyclic alkyl group having 3-20 carbon atoms, a straight-chain alkoxy group having 1-20 carbon atoms, a branched-chain alkoxy group having 3-20 carbon atoms, a cyclic alkoxy group having 3-20 carbon atoms, a straight-chain alkylthio group having 1-20 carbon atoms, a branched-chain alkylthio group having 3-20 carbon atoms, a cyclic alkylthio group having 3-20 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by a combination of the above groups.

[0063] Further, each occurrence of R7 is independently selected from -H, -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-20 carbon atoms, branched-chain alkyl having 3-20 carbon atoms, cyclic alkyl having 3-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, branched-chain alkoxy having 3-20 carbon atoms, cyclic alkoxy having 3-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, branched-chain alkylthio having 3-20 carbon atoms, cyclic alkylthio having 3-20 carbon atoms, or selected from any of the following groups:

[0064]

[0065] Wherein: W is selected from O, S, or Se;

[0066] R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108Each occurrence is independently selected from -H, -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-20 carbon atoms, branched-chain alkyl having 3-20 carbon atoms, cyclic alkyl having 3-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, branched-chain alkoxy having 3-20 carbon atoms, cyclic alkoxy having 3-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, branched-chain alkylthio having 3-20 carbon atoms, cyclic alkylthio having 3-20 carbon atoms, or a group formed by a combination of the above groups;

[0067] * indicates the attachment site.

[0068] In one specific embodiment, the W is selected from S or Se.

[0069] In a specific embodiment, each occurrence of R7 is independently selected from -H, -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-10 carbon atoms, branched-chain alkyl having 3-10 carbon atoms, cyclic alkyl having 3-10 carbon atoms, straight-chain alkoxy having 1-10 carbon atoms, branched-chain alkoxy having 3-10 carbon atoms, cyclic alkoxy having 3-10 carbon atoms, straight-chain alkylthio having 1-10 carbon atoms, branched-chain alkylthio having 3-10 carbon atoms, cyclic alkylthio having 3-10 carbon atoms, or any of the following groups:

[0070] .

[0071] In one embodiment, R1, R2, R5, and R6 are independently selected from -H, -D, or any of the following groups:

[0072] , ;

[0073] in:

[0074] R 109 Each occurrence is independently selected from a straight chain alkyl having 1-30 carbon atoms, a branched chain alkyl having 3-30 carbon atoms, a straight chain alkoxy having 1-30 carbon atoms, a branched chain alkoxy having 3-30 carbon atoms, a straight chain alkylthio having 1-30 carbon atoms, or a branched chain alkylthio having 3-30 carbon atoms;

[0075] Ar2 is selected from an aromatic group having 6-10 carbon atoms, or a heteroaromatic group having 5-10 ring atoms;

[0076] R a Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, a cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by a combination of the above groups;

[0077] R b Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-20 carbon atoms, branched-chain alkyl having 3-20 carbon atoms, cyclic alkyl having 3-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, branched-chain alkoxy having 3-20 carbon atoms, cyclic alkoxy having 3-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, branched-chain alkylthio having 3-20 carbon atoms, cyclic alkylthio having 3-20 carbon atoms;

[0078] m is selected from an integer ≥0; q is selected from an integer ≥0.

[0079] It should be noted that the maximum value that can be selected for m is the maximum number of substitutable sites in the Ar2 group; the maximum value that can be selected for q is R 109 The maximum number of substitutable sites in a group.

[0080] In one specific embodiment, m is selected from 0, 1, 2, 3, 4 or 5.

[0081] In one embodiment, q is selected from 0, 1, 2, 3 or 4.

[0082] In one embodiment, Ar2 is selected from phenyl or thiophene. 109 Each occurrence is independently selected from straight chain alkyl having 1 to 20 carbon atoms, branched chain alkyl having 3 to 20 carbon atoms, straight chain alkoxy having 1 to 20 carbon atoms.

[0083] In a specific embodiment, the R a Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, cyclohexyl, adamantyl, phenyl, thienyl, or a group formed by a combination of the above groups.

[0084] In one embodiment, R3 and R4 are independently selected from , where R 110 Each occurrence is independently selected from a straight chain alkyl group having 1 to 30 carbon atoms, or a branched chain alkyl group having 3 to 30 carbon atoms; R cEach occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, a cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by a combination of the above groups; r is selected from an integer ≥0.

[0085] It should be noted that the maximum value that r can choose is R 110 The maximum number of substitutable sites in a group.

[0086] In one embodiment, r is selected from 0, 1, 2, 3 or 4.

[0087] In a specific embodiment, the R 110 Each occurrence is independently selected from a straight chain alkyl group having 1 to 20 carbon atoms, or a branched chain alkyl group having 3 to 20 carbon atoms; R c Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, cyclohexyl, adamantyl, phenyl, thienyl, or a group formed by a combination of the above groups.

[0088] Preferably, the organic compound containing cyano-substituted 1,3-indandione provided by the present invention is selected from the following structures, but is not limited thereto:

[0089]

[0090] .

[0091] The present invention further relates to a photoactive layer receptor material, wherein the photoactive layer receptor material is selected from the organic compounds containing cyano-substituted 1,3-indandione as described above.

[0092] The second aspect of the present invention relates to a mixture, the mixture comprising the organic compound containing cyano-substituted 1,3-indandione as described above and at least another organic functional material. Preferably, the another organic functional material is selected from a photoactive layer donor material or another photoactive layer acceptor material.

[0093] In one embodiment, the mixture comprises an organic compound containing a cyano-substituted 1,3-indandione as described in formula (I) and at least one photoactive layer donor material.

[0094] In one embodiment, the mixture comprises an organic compound containing a cyano-substituted 1,3-indandione as described in formula (II) and at least one photoactive layer donor material and at least another photoactive layer acceptor material.

[0095] In one embodiment, the photoactive layer donor material is selected from a polymer donor material; further, the donor material can be selected from one, two or more of PBDB-T, PM6, PM7, D18, D18-Cl, PTO2, PB2, PB2F, PTVT-BT, PTQ10, PTQ11, PBQx-TCl, PQM-Cl, J106, and J52-Cl, but is not limited thereto:

[0096]

[0097]

[0098] ;

[0099] Wherein, n represents the number of repeating units and is an integer greater than 1.

[0100] Preferably, the another photoactive layer acceptor material is selected from a non-fullerene acceptor material or a fullerene derivative acceptor material. In a specific embodiment, the another photoactive layer acceptor material is selected from PC 61 BM([6,6]-phenyl C 61 Methyl butyrate), PC 71 BM([6,6]-phenyl C 71 Methyl butyrate), indene-containing fullerene and any of the following structures, but not limited thereto;

[0101] .

[0102] The third aspect of the present invention relates to a composition, which comprises the organic compound or mixture containing cyano-substituted 1,3-indandione as described above, and at least one organic solvent.

[0103] Preferably, the organic solvent can be selected from the group consisting of dichloromethane, chloroform, chlorobenzene, chloroform, 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, tetralin, 2-methylthiophene, 3-methylthiophene, decahydronaphthalene, indane, methyl benzoate, ethyl benzoate, mesitylene, or a mixture of two or more thereof.

[0104] Preferably, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.

[0105] In one embodiment, the composition may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but not limited to, 1,8-diiodooctane (DIO), diphenyl ether (DPE), anthracene, 1,4-diiodobenzene (DIB), 1,3-dibromo-5-chlorobenzene (DBCl), 3,5-dichlorobromobenzene (DCBB), 1-chloronaphthalene (1-CN), 1, 3, 5-tribromobenzene (TBB), etc., but are not limited thereto.

[0106] It should be noted that the present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In one embodiment, the above composition is used to prepare an organic electronic device by a printing or coating preparation method. The printing or coating preparation method can be, but is not limited to, inkjet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slit extrusion coating, etc. The preferred ones are slit coating, spin coating and inkjet printing.

[0107] The fourth aspect of the present invention provides an organic electronic device, comprising at least one functional layer, wherein the at least one functional layer comprises an organic compound or mixture containing cyano-substituted 1,3-indandione as described above or is prepared from a composition. Preferably, the organic electronic device is selected from an organic photovoltaic cell (OPV), an organic light emitting diode (OLED), an organic field effect transistor (OFET), an organic laser, an organic photodetector (OPD), etc. Preferably, the organic electronic device is selected from an organic photovoltaic cell (OPV).

[0108] Preferably, the organic electronic device comprises a first electrode, a second electrode, and at least one functional layer located between the first electrode and the second electrode, wherein the at least one functional layer comprises the organic compound or mixture of cyano-substituted 1,3-indanedione as described above or is prepared from the composition.

[0109] Furthermore, according to the present invention, the organic electronic device is selected from an organic photovoltaic cell, wherein the organic photovoltaic cell comprises at least an anode, a cathode and a photoactive layer located between the anode and the cathode, and the photoactive layer comprises the organic compound or mixture of cyano-substituted 1,3-indanedione as described above, or is prepared from the above composition.

[0110] At least one of the anode and cathode is transparent or translucent to facilitate the incidence of light. The material used to prepare the electrode 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; conductive nanomaterials, such as metal nanowires, nanoparticle slurries, graphene, carbon nanotubes, etc.; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; combinations of metals and oxides, such as ZnO:Al or SnO2:Sb, etc.; and conductive polymers, such as PEDOT:PSS, polypyrrole and polyaniline, etc.; or materials with a multilayer structure, such as LiF / Al, LiO2 / Al, LiF / Fe, MoO3 / Al, Al:Li, Al:BaF2 and Al:BaF2:Ba, etc., but are not limited thereto.

[0111] The photoactive layer comprises a photoactive layer donor material and a photoactive layer acceptor material. The photoactive layer donor material is preferably one, two or more selected from PBDB-T, PM6, PM7, D18, D18-Cl, PTO2, PB2, PB2F, PTVT-BT, PTQ10, PTQ11, PBQx-TCl, PQM-Cl, J106, and J52-Cl, but is not limited thereto.

[0112] The photoactive layer receptor material at least comprises the organic compound containing cyano-substituted 1,3-indandione as described above; further, the photoactive layer receptor material may further comprise another photoactive layer receptor, preferably, the another photoactive layer receptor material is selected from non-fullerene receptor materials or fullerene derivative receptor materials. Specifically, the another photoactive layer receptor material is selected from PC 61 BM([6,6]-phenyl C 61 Methyl butyrate), PC 71 BM([6,6]-phenyl C 71 butyrate methyl ester), indene-containing fullerene and compounds (A-1) to (A-21), but are not limited thereto.

[0113] Further, the photoactive layer can be prepared by dissolving the photoactive donor material 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, slit coating and inkjet printing, but not limited thereto.

[0114] The mass ratio of the photoactive layer donor material to the acceptor material in the organic solvent is preferably: 1:0.8~1:1.5; further, the mass ratio of the photoactive layer donor material to the acceptor material in the organic solvent is preferably: 1:1~1:1.5; the mass ratio of the photoactive layer donor material to the acceptor material in the organic solvent is preferably: 1:1~1:1.2.

[0115] The concentration of the photoactive layer donor material in the organic solvent is preferably 3-15 mg / mL; further, the concentration of the photoactive layer donor material in the organic solvent is preferably 4-10 mg / mL.

[0116] The organic solvent has the same meaning as described in the composition.

[0117] In one embodiment, the organic solar cell further comprises a cathode buffer layer, wherein the cathode buffer layer is located between the cathode and the photoactive layer.

[0118] Preferably, the cathode buffer layer material can be selected from metal complexes, metal oxides, metal salts, etc. with low work function, such as metal complexes of 8-hydroxyquinoline, complexes containing Alq3, metal complexes containing Liq, LiF, Ca, titanium oxide (TiO x ), zinc oxide (ZnO), cesium carbonate (Cs2CO3), etc.; it can also be a polymer material, such as PFN-Br or PFN or PDINN or PDINO or PNDIT-F3N-Br or PNDIT-F3N, etc., but not limited to this.

[0119] In one embodiment, the organic solar cell further comprises an anode buffer layer, wherein the anode buffer layer is located between the anode and the photoactive layer.

[0120] Preferably, the anode buffer layer material is selected from PEDOT:PSS, molybdenum oxide (MoO x ), vanadium oxide (V2O5), nickel oxide (NiO), tungsten oxide (WO x , preferably, x is selected from 2 or 3), small molecule self-assembly materials such as 2PACz, MeO-2PACz, etc., but not limited thereto.

[0121] It should be noted that, in order to improve the performance of the organic solar cell device, the organic solar cell may further include other functional layers, including but not limited to a charge blocking layer and a charge transport layer.

[0122] Furthermore, the organic solar cell further comprises a substrate. In one embodiment, the substrate is disposed on one side of the anode and on a different side from the photoactive layer. In another embodiment, the substrate is disposed on one side of the cathode and on a different side from the photoactive layer.

[0123] In one embodiment, as a substrate, a substrate having excellent transparency, surface smoothness, ease of handling, and water resistance can be used. Specifically, a glass substrate, a thin film glass substrate, or a transparent plastic substrate can be used. The plastic substrate may include a film in a single-layer or multi-layer form, such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), polyparaxylene (Parylene), etc., but is not limited thereto, and a substrate commonly used for organic photovoltaic cells may also be used.

[0124] In a specific embodiment, the organic photovoltaic cell is stacked with an anode, an anode buffer layer, a photoactive layer, a cathode buffer layer and a cathode in sequence from bottom to top, and the photoactive layer comprises the organic compound or mixture of 1,3-indandione substituted with a cyano group as described above, or is prepared from the above composition.

[0125] The organic photovoltaic cell according to the present invention is mainly used in the fields of wearable devices, smart Internet of Things, smart home, smart agriculture, building photovoltaics, new energy vehicles, indoor photovoltaics, etc.

[0126] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should be aware that certain 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.

[0127] Here, the organic compound containing cyano-substituted 1,3-indandione and the organic electronic device of the present invention are exemplified, but the present invention is not limited to the following examples.

[0128] Synthesis Example of Organic Compounds Containing Cyano-Substituted 1,3-Indandione

[0129] Synthesis Example 1: Synthesis of Compound (3)

[0130]

[0131] Synthesis of compound 1-2:

[0132] Accurately weigh compound 1-1 (1084 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) at -20 °C. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:4 (volume ratio), and obtain about 952 mg of compound 1-2, with a yield of 83.5%. MALDI-TOF-MS:1139.69.

[0133] Synthesis of compound (3):

[0134] Accurately weigh compound 1-2 (570 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, the eluent is PE:DCM=1:2 (volume ratio), and obtain about 496 mg of compound (3), with a yield of 66.3%. MALDI-TOF-MS: 1495.92.

[0135] Synthesis Example 2: Synthesis of Compound (4)

[0136]

[0137] Synthesis of compound 2-2:

[0138] Accurately weigh compound 2-1 (1000 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 872 mg of compound 2-2, with a yield of 82.6%. MALDI-TOF-MS:1055.26.

[0139] Synthesis of compound (4):

[0140] Accurately weigh compound 2-2 (528 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, the eluent is PE:DCM=1:2 (volume ratio), and obtain about 432 mg of compound (4), with a yield of 61.2%. MALDI-TOF-MS: 1411.89.

[0141] Synthesis Example 3: Synthesis of Compound (9)

[0142]

[0143] Synthesis of compound 3-2:

[0144] Accurately weigh compound 3-1 (1152 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) at -20 °C. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 762 mg of compound 3-2, with a yield of 63.1%. MALDI-TOF-MS:1207.41.

[0145] Synthesis of compound (9):

[0146] Accurately weigh compound 3-2 (604 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 362 mg of compound (9), with a yield of 46.3%. MALDI-TOF-MS: 1564.29.

[0147] Synthesis Example 4: Synthesis of Compound (12)

[0148]

[0149] Synthesis of compound 4-2:

[0150] Accurately weigh compound 4-1 (1018 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 653 mg of compound 4-2, with a yield of 60.8%. MALDI-TOF-MS:1074.79.

[0151] Synthesis of compound (12):

[0152] Accurately weigh compound 4-2 (537 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, the eluent is PE:DCM=1:2 (volume ratio), and obtain about 496 mg of compound (12), with a yield of 69.3%. MALDI-TOF-MS: 1430.58.

[0153] Synthesis Example 5: Synthesis of Compound (17) (-Ph is phenyl)

[0154]

[0155] Synthesis of compound 5-2:

[0156] Accurately weigh compound 5-1 (1276 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel, with the eluent being PE:DCM=1:5 (volume ratio), to obtain about 701 mg of compound 5-2, with a yield of 52.6%. MALDI-TOF-MS:1332.81.

[0157] Synthesis of compound (17):

[0158] Accurately weigh compound 5-2 (666 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 401 mg of compound (17), with a yield of 47.5%. MALDI-TOF-MS: 1688.39.

[0159] Synthesis Example 6: Synthesis of Compound (20)

[0160]

[0161] Synthesis of compound 6-2:

[0162] Accurately weigh compound 6-1 (1078 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 692 mg of compound 6-2, with a yield of 61.0%. MALDI-TOF-MS:1133.56.

[0163] Synthesis of compound (20):

[0164] Accurately weigh compound 6-2 (567 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 305 mg of compound (20), with a yield of 40.9%. MALDI-TOF-MS: 1490.62.

[0165] Synthesis Example 7: Synthesis of Compound (25)

[0166]

[0167] Synthesis of compound 7-2:

[0168] Accurately weigh compound 7-1 (1230 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel, with the eluent being PE:DCM=1:5 (volume ratio), to obtain about 712 mg of compound 7-2, with a yield of 55.4%. MALDI-TOF-MS:1286.12.

[0169] Synthesis of compound (25):

[0170] Accurately weigh compound 7-2 (643 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 404 mg of compound (25), with a yield of 49.2%. MALDI-TOF-MS: 1642.73.

[0171] Synthesis Example 8: Synthesis of Compound (28)

[0172]

[0173] Synthesis of compound 8-2:

[0174] Accurately weigh compound 8-1 (1266 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 743 mg of compound 8-2, with a yield of 56.2%. MALDI-TOF-MS:1321.65.

[0175] Synthesis of compound (28):

[0176] Accurately weigh compound 8-2 (661 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, the eluent is PE:DCM=1:2 (volume ratio), and obtain about 493 mg of compound (28), with a yield of 58.8%. MALDI-TOF-MS:1678.58.

[0177] Synthesis Example 9: Synthesis of Compound (34)

[0178]

[0179] Synthesis of compound 9-2:

[0180] Accurately weigh compound 9-1 (1446 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) at -20 °C. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 779 mg of compound 9-2, with a yield of 51.8%. MALDI-TOF-MS:1502.64.

[0181] Synthesis of compound (34):

[0182] Accurately weigh compound 9-2 (751 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 485 mg of compound (34), with a yield of 52.2%. MALDI-TOF-MS: 1858.32.

[0183] Synthesis Example 10: Synthesis of Compound (40)

[0184]

[0185] Synthesis of compound 10-2:

[0186] Accurately weigh compound 10-1 (551 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 366 mg of compound 10-2, with a yield of 60.4%. MS: 606.29.

[0187] Synthesis of compound (40):

[0188] Accurately weigh compound 10-2 (303 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 332 mg of compound (40), with a yield of 68.9%. MS:963.53.

[0189] Synthesis Example 11: Synthesis of Compound (42)

[0190]

[0191] Synthesis of compound 11-2:

[0192] Accurately weigh compound 11-1 (646 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) at -20 °C. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 452 mg of compound 11-2, with a yield of 64.3%. MS:702.81.

[0193] Synthesis of compound (42):

[0194] Accurately weigh compound 11-2 (351 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 362 mg of compound (42), with a yield of 68.4%. MALDI-TOF-MS: 1058.06.

[0195] Synthesis Example 12: Synthesis of Compound (44)

[0196]

[0197] Synthesis of compound 12-2:

[0198] Accurately weigh compound 12-1 (2.0 g, 5.0 mmol), trimethyl-2-thienyl-stannane (16.3 g, 15.0mmol), bistriphenylphosphine palladium dichloride (140 mg, 0.2 mmol), and toluene (40 mL) and add them into a 100 mL three-necked flask in sequence, replace nitrogen three times, and reflux the mixture at 80°C overnight. The reaction was quenched with water, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous MgSO4, and the excess solvent was removed by vacuum distillation. The silica gel sample was mixed and column chromatography was performed, and the eluent was PE:DCM=3:1 (volume ratio), and about 1.5 g of compound 12-2 was obtained, with a yield of 74.1%. MS: 412.87.

[0199] Synthesis of compound 12-3

[0200] Accurately weigh compound 12-2 (1.2 g, 3.0 mmol), triethyl phosphite (2.5 g, 15 mmol), and o-dichlorobenzene (20 mL) and add them to a 100 mL three-necked flask in sequence. Replace nitrogen three times and react at 160°C overnight. The reaction was quenched with water, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous MgSO4, and the excess solvent was removed by vacuum distillation. The silica gel sample was mixed with the column chromatography, and the eluent was PE:DCM=3:1 (volume ratio). Compound 12-3 was obtained, about 712 mg, with a yield of 68.1%. MS: 348.56.

[0201] Synthesis of compound 12-4:

[0202] Accurately weigh compound 12-3 (627 mg, 1.8 mmol), isooctane bromide (1.7 g, 9.0 mmol), potassium carbonate (2.5 g, 18 mmol), potassium iodide (299 mg, 1.8 mmol) and add them to a 50 mL three-necked flask, add ultra-dry DMF (15 mL), replace nitrogen three times, and reflux the mixture at 100°C overnight. The reaction was quenched with H2O, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous MgSO4, and the excess solvent was removed by vacuum distillation. The silica gel sample was mixed and column chromatography was performed, and the eluent was PE:DCM=1:1 (volume ratio), and about 680 mg of compound 12-4 was obtained, with a yield of 65.9%. MS: 573.32.

[0203] Synthesis of compound 12-5:

[0204] Accurately weigh compound 12-4 (573 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly drop POCl3 (0.28 mL 3 mmol) under -20 °C atmosphere. After stirring for 1 hour, heat the mixture to 60 °C for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and about 362 mg of compound 12-5 is obtained, with a yield of 57.6%. MS: 628.76.

[0205] Synthesis of compound (44):

[0206] Accurately weigh compound 12-5 (314 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask in sequence, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, with the eluent being PE:DCM=1:2 (volume ratio), to obtain about 248 mg of compound (44), with a yield of 50.3%. MS: 985.73.

[0207] Synthesis Example 13: Synthesis of Compound (51)

[0208]

[0209] Synthesis of compound 13-1:

[0210] Accurately weigh 3-methoxythiophene (9.7 g, 85.0 mmol), p-toluenesulfonic acid (1.5 g, 8.5 mmol), n-decanol (23.7 g 128 mmol), and toluene (100 mL) and add them to a 250 mL three-necked flask in sequence. Replace nitrogen three times, react at 120°C overnight, adjust the pH of the reaction solution to neutral with 5% potassium hydroxide solution, and extract the aqueous phase with ethyl acetate three times. Dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel with PE as the eluent to obtain about 13.1 g of compound 13-1, with a yield of 63.9%. MS: 241.05.

[0211] Synthesis of compound 13-2:

[0212] Accurately weigh compound 13-1 (12.5 g, 52.0 mmol) and add it to a 250 mL three-necked flask, add ultra-dry THF (125 mL), replace nitrogen three times, cool to -60 ° C, start to drop LDA (36.0 mL, 2.0M), keep warm for two hours, start to drop TMSCl (8.5 g, 78 mmol), react for 5 hours, quench the reaction with water, and extract the aqueous phase with ethyl acetate three times. Dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, mix the sample with neutral alumina column chromatography, and use PE as eluent to obtain about 10.5 g of compound 13-2, with a yield of 64.7%. MS: 312.24.

[0213] Synthesis of compound 13-3:

[0214] Accurately weigh compound 13-2 (10.3 g, 33.0 mmol) and add it to a 250 mL three-necked flask, add ultra-dry THF (100 mL), replace nitrogen three times, cool to -60 ° C, start to drop LDA (21.5 mL, 2.0M), keep warm for two hours, start to drop trimethyltin chloride (8.5 g, 42.9 mmol), react for 2 hours, quench the reaction with potassium fluoride solution, and extract the aqueous phase with ethyl acetate three times. Dry the combined organic phase with anhydrous MgSO4, and remove the excess solvent by vacuum distillation to obtain about 14.5 g of compound 13-3, with a yield of 92.4%. MS: 475.94.

[0215] Synthesis of compound 13-4:

[0216] Accurately weigh compound 13-3 (14.3 g, 30.0 mmol), 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (3.8 g, 10.0 mmol), bistriphenylphosphine palladium dichloride (350 mg, 0.5 mmol), and toluene (140 mL) and add them into a 250 mL three-necked flask in sequence, replace nitrogen three times, and reflux the mixture at 80°C overnight. The reaction was quenched with water, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous MgSO4, and the excess solvent was removed by vacuum distillation. The silica gel sample was mixed and column chromatography was performed, and the eluent was PE:DCM=3:1 (volume ratio), to obtain about 5.3 g of compound 13-4, with a yield of 62.5%. MS:847.46.

[0217] Synthesis of compound 13-5:

[0218] Accurately weigh compound 13-4 (5.1 g, 6.0 mmol), triethyl phosphite (5.1 mL, 30.0 mmol), and o-dichlorobenzene (100 mL) and add them to a 250 mL three-necked flask in sequence. Replace nitrogen three times and react at 160°C overnight. The reaction was quenched with water, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous MgSO4, and the excess solvent was removed by vacuum distillation to obtain about 3.9 g of compound 13-5, with a yield of 82.9%. MS: 782.67.

[0219] Synthesis of compound 13-6:

[0220] Accurately weigh compound 13-5 (3.1 g, 4.0 mmol), 2-butyl-1-bromooctane (5.0 g, 20.0mmol), potassium carbonate (5.5 g, 40.0 mmol), potassium iodide (0.7 g, 4.0 mmol) and add them to a 100 mL three-necked flask in sequence, add ultra-dry DMF (35 mL), replace nitrogen three times, and reflux the mixture at 100°C overnight. The reaction was quenched with H2O, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phase was dried over anhydrous MgSO4, and the excess solvent was removed by vacuum distillation. The silica gel sample was mixed with the column chromatography, and the eluent was PE:DCM=1:1 (volume ratio), and about 2.5 g of compound 13-6 was obtained, with a yield of 55.8%. MS: 1119.32.

[0221] Synthesis of compound 13-7:

[0222] Accurately weigh compound 13-6 (2.2 g, 2.0 mmol) and add it to a 250 mL three-necked flask, add chloroform (120 mL), replace nitrogen 3 times, add TFA (20 mL) dropwise, react for 2 hours, adjust the pH of the reaction solution to neutral with 5% potassium hydroxide solution, and extract the aqueous phase with dichloromethane three times. Dry the combined organic phase with anhydrous MgSO4, remove the excess solvent by vacuum distillation, and perform column chromatography on silica gel, with PE as the eluent, to obtain about 1.6 g of compound 13-7, with a yield of 82.0%. MS: 975.72.

[0223] Synthesis of compound 13-8:

[0224] Accurately weigh compound 13-7 (976 mg, 1.0 mmol) and add it to a 100 mL three-necked flask, add anhydrous DMF (20 mL), replace nitrogen three times, and slowly add POCl3 (0.28 mL 3 mmol) dropwise at -20 °C. After stirring for 1 hour, heat the mixture to 60 °C and react for 1 hour. Then quench the reaction with H2O, and extract the aqueous phase with ethyl acetate three times. Then dry the combined organic phase with anhydrous MgSO4, remove excess solvent by vacuum distillation, and perform column chromatography on silica gel. The eluent is PE:DCM=1:5 (volume ratio), and obtain about 675 mg of compound 13-8, with a yield of 65.5%. MS:1031.83.

[0225] Synthesis of compound (51):

[0226] Accurately weigh compound 13-8 (516 mg, 0.5 mmol), compound 1-3 (549 mg, 2.8 mmol) and pyridine (1 mL) and add them to a 100 mL three-necked flask, add chloroform (20 mL), replace nitrogen three times, and stir the reaction at room temperature overnight. Pour the mixture into methanol and filter, and purify the residue by silica gel column chromatography, eluent PE:DCM=1:2 (volume ratio), to obtain about 324 mg of compound (51), yield 46.7%. MALDI-TOF-MS:1387.58.

[0227] Organic Photovoltaic Cell (OPV) Device Preparation and Characterization Example

[0228] This embodiment exemplifies the preparation, implementation and characterization of the OPV device in the organic electronic device provided by the present invention, but the present invention is not limited to the following embodiment.

[0229] like Figure 1 As shown, the OPV device structure is as follows: indium tin oxide ITO / 2PACz / photoactive layer / PDINN / / Ag. The preparation method is as follows:

[0230] 1) ITO substrate cleaning:

[0231] The ITO conductive glass was cleaned with detergent, rinsed, and then ultrasonically cleaned with deionized water, acetone, and isopropanol for 15 minutes, then blown dry with nitrogen and treated in a plasma cleaner for 5 minutes to further clean the surface and improve wettability.

[0232] 2) Anode buffer layer preparation

[0233] The anode buffer layer solution is evenly spin-coated on the ITO in air at a spin-coating speed of 3000 rpm for 30 seconds, and dried at 100° C. for 10 minutes to obtain the anode buffer layer. The anode buffer layer solution preparation method is as follows: the anode buffer layer material 2PACz is dissolved in an organic solvent methanol at a concentration of 0.2 mg / mL to obtain the anode buffer layer solution.

[0234] 3) Preparation of photoactive layer

[0235] In a glove box (inert gas atmosphere), the photoactive layer solution was evenly spin-coated on the anode buffer layer at a rotation speed of 1800-4000 rpm to obtain a photoactive layer with a total thickness of about 100 nm.

[0236] The donor material in the photoactive layer solution is selected from PTQ10, and the acceptor material is selected from compound (3). The polymer PTQ10 and the acceptor material compound (3) are dissolved in chloroform, the mass ratio of PTQ10:compound (3) is 1:1.2, and the total concentration of PTQ10:compound (3) in chloroform is 16 mg / mL. 0.5% by volume of DIO is added as an additive to obtain a photoactive layer solution.

[0237] 4) Preparation of cathode buffer layer

[0238] After thermal annealing on a hot plate at 100°C for 10 minutes, the cathode buffer layer material PDINN (PDINN was dissolved in methanol to prepare a solution with a concentration of 1.0 mg / mL) was evenly spin-coated on the photoactive layer at a spin coating speed of 3500 rpm and a spin time of 30 seconds to obtain a cathode buffer layer.

[0239] 5) Cathode layer preparation

[0240] In high vacuum (1×10 -6 Ag was evaporated onto the cathode buffer layer at a pressure of 100 mbar to form a cathode layer with a thickness of about 100 nm.

[0241] 6) Packaging

[0242] The devices were encapsulated with UV-curable resin in a nitrogen glove box.

[0243] Device Examples 2-6

[0244] The preparation methods of device examples 2-6 refer to the preparation method of device example 1, except that the choice of photoactive layer receptor material is different. Specifically, the receptor material compound (3) in device example 1 is replaced by compound (4), compound (12), compound (17), compound (25), and compound (34), respectively. See Table 1 for details.

[0245] Device Comparative Example 1

[0246] The preparation method of device comparative example 1 refers to the preparation method of device example 1, except that the choice of photoactive layer receptor material is different. Specifically, the receptor material compound (3) in device example 1 is replaced by the comparative compound (Ref-1). See Table 1 for details.

[0247] Device Comparative Example 2

[0248] The preparation method of device comparative example 2 refers to the preparation method of device example 1, except that the choice of photoactive layer receptor material is different. Specifically, the receptor material compound (3) in device example 1 is replaced by the comparative compound (Ref-2).

[0249]

[0250] The prepared organic photovoltaic cell device was subjected to a performance test under sunlight. Under the irradiation of standard light from a solar simulator (AM1.5G), the cell current-voltage curve was tested and the photoelectric conversion efficiency was calculated; see Table 1 for details.

[0251] Table 1

[0252]

[0253] Device Example 7

[0254] The preparation method of device embodiment 7 refers to the preparation method of device embodiment 1, except that the preparation of the photoactive layer is different, as follows:

[0255] In a glove box (inert gas atmosphere), the photoactive layer solution was evenly spin-coated on the anode buffer layer at a rotation speed of 1800-4000 rpm to obtain a photoactive layer with a total thickness of about 100 nm.

[0256] The donor material in the photoactive layer solution is selected from PTQ10, and the acceptor material is selected from the compound A-2 and compound (3) mentioned above. The polymer PTQ10, the acceptor material A-2 and the compound (3) are dissolved in chloroform, the mass ratio of the PTQ10: the compound A-2: the compound (3) is 1:1.1:0.1, and the total concentration of the PTQ10: the compound A-2: the compound (3) in chloroform is 16 mg / mL. 0.5% by volume of DIO is added as an additive to the solution to obtain a photoactive layer solution.

[0257] Device Examples 8-14

[0258] The preparation methods of device examples 8 to 14 refer to the preparation method of device example 7, except that the selection of the photoactive layer receptor material is different. Specifically, the receptor material compound (3) in device example 7 is replaced by compound (9), compound (20), compound (28), compound (40), compound (42), compound (44) and compound (51), respectively. See Table 2 for details.

[0259] Device Comparative Example 3

[0260] The preparation method of device comparative example 3 refers to the preparation method of device example 7, except that the selection of the photoactive layer receptor material is different. Specifically, the receptor material compound (3) in device example 7 is replaced by the comparative compound (Ref-1). See Table 2 for details.

[0261] Device Comparative Example 4

[0262] The preparation method of device comparative example 4 refers to the preparation method of device example 7, except that the selection of the photoactive layer receptor material is different. Specifically, the receptor material compound (3) in device example 7 is replaced by the comparative compound (Ref-2).

[0263] The prepared organic solar cell device was subjected to a performance test under sunlight. Under the irradiation of standard light from a solar simulator (AM 1.5G), the cell current-voltage curve was tested and the photoelectric conversion efficiency was calculated. See Table 2 for details.

[0264] Table 2

[0265]

[0266] As can be seen from the data in Table 1, the photoelectric conversion efficiency of the organic solar cell provided by the organic compound containing cyano-substituted 1,3-indanedione provided by the present invention is greatly improved compared with the comparative compound. The reason is that: the end group of the organic compound containing cyano-substituted 1,3-indanedione provided by the present invention is selected from , compared to It has more suitable energy levels and planarity, thus enhancing the π-π stacking and charge transfer between molecules; compared with On the one hand, CN has a stronger electron-withdrawing effect than halogen, thus enhancing the charge transfer effect within the molecule, and on the other hand, further adjusts the energy level of the compound to make it more compatible with the energy level of the donor structure. Therefore, the device effects of device embodiments 1-6 of the present invention are far better than those of device comparative embodiments 1 and 2.

[0267] It can be seen from the data in Table 2 that the organic compound containing cyano-substituted 1,3-indandione provided by the present invention has a more suitable energy level and spatial structure than the comparative compound. When it is used as the third component in an organic solar cell device, it can optimize the morphology of the active layer and promote the dissociation and transfer of charges, thereby improving the photoelectric performance of the device.

[0268] The above examples further illustrate the content of the present application, but should not be construed as limiting the present application. Without departing from the spirit and substance of the present application, modifications and replacements made to the methods, steps or conditions of the present application all fall within the scope of the present application. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.

Claims

1. An organic compound containing a cyano-substituted 1,3-indandione, characterized in that: The organic compound has a structure as shown in general formula (I) or general formula (II): （I） (II) in: Each occurrence of Z is independently selected from O, S or Se; Ar1 is selected from a substituted or unsubstituted heteroaromatic group having 5-6 ring atoms; R1, R2, R3, R4, R5, R6 are independently selected from -H, -D, substituted or unsubstituted straight-chain alkyl having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkyl having 3-30 carbon atoms, substituted or unsubstituted straight-chain alkoxy having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkoxy having 3-30 carbon atoms, substituted or unsubstituted straight-chain alkylthio having 1-30 carbon atoms, substituted or unsubstituted branched-chain alkylthio having 3-30 carbon atoms, substituted or unsubstituted aromatic group having 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic group having 5-20 ring atoms; The “substituted or unsubstituted” means that the defined group is not substituted or is substituted by one or more substituents R, wherein each occurrence of R is independently selected from -D, -F, -Cl, -Br, -I, cyano, nitro, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched-chain alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a branched-chain alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a straight-chain alkylthio group having 1 to 20 carbon atoms, a branched-chain alkylthio group having 3 to 20 carbon atoms, a cyclic alkylthio group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms, or a group formed by a combination of the above groups.

2. The organic compound containing cyano-substituted 1,3-indandione according to claim 1, characterized in that: The Ar1 is selected from any of the following groups: ; Wherein: Y is selected from O, S, Se, NR8; R8 is selected from a linear alkyl group having 1 to 30 carbon atoms, or a branched or cyclic alkyl group having 3 to 30 carbon atoms; R7, at each occurrence, is independently selected from -H, -D, -F, -Cl, -Br, -I, cyano, nitro, a straight-chain alkyl group having 1-20 carbon atoms, a branched-chain alkyl group having 3-20 carbon atoms, a cyclic alkyl group having 3-20 carbon atoms, a straight-chain alkoxy group having 1-20 carbon atoms, a branched-chain alkoxy group having 3-20 carbon atoms, a cyclic alkoxy group having 3-20 carbon atoms, a straight-chain alkylthio group having 1-20 carbon atoms, a branched-chain alkylthio group having 3-20 carbon atoms, a cyclic alkylthio group having 3-20 carbon atoms, an aromatic group having 6-20 carbon atoms, a heteroaromatic group having 5-20 ring atoms, or a group formed by a combination of the above groups; # indicates a fusion site, and the fusion site selects a C atom.

3. The organic compound containing cyano-substituted 1,3-indandione according to claim 2, characterized in that: The organic compound has a structure as shown in any one of the general formulas (III-1) to (III-4): 。 4. The organic compound containing cyano-substituted 1,3-indandione according to claim 3, characterized in that: Each occurrence of R7 is independently selected from -H, -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-20 carbon atoms, branched-chain alkyl having 3-20 carbon atoms, cyclic alkyl having 3-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, branched-chain alkoxy having 3-20 carbon atoms, cyclic alkoxy having 3-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, branched-chain alkylthio having 3-20 carbon atoms, cyclic alkylthio having 3-20 carbon atoms, or any of the following groups: Wherein: W is selected from O, S, Se; R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108 Each occurrence is independently selected from -H, -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-20 carbon atoms, branched-chain alkyl having 3-20 carbon atoms, cyclic alkyl having 3-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, branched-chain alkoxy having 3-20 carbon atoms, cyclic alkoxy having 3-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, branched-chain alkylthio having 3-20 carbon atoms, cyclic alkylthio having 3-20 carbon atoms, or a group formed by a combination of the above groups; * indicates the attachment site.

5. The organic compound containing cyano-substituted 1,3-indandione according to any one of claims 1 to 4, characterized in that: The R1, R2, R5, and R6 are independently selected from -H, -D, or any of the following groups: 、 ； in: R 109 Each occurrence is independently selected from a straight chain alkyl having 1-30 carbon atoms, a branched chain alkyl having 3-30 carbon atoms, a straight chain alkoxy having 1-30 carbon atoms, a branched chain alkoxy having 3-30 carbon atoms, a straight chain alkylthio having 1-30 carbon atoms, or a branched chain alkylthio having 3-30 carbon atoms; Ar2 is selected from an aromatic group having 6-10 carbon atoms, or a heteroaromatic group having 5-10 ring atoms; R a Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, a cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by a combination of the above groups; R b Each occurrence is independently selected from -H, -D, -F, -Cl, -Br, -I, cyano, nitro, straight-chain alkyl having 1-20 carbon atoms, branched-chain alkyl having 3-20 carbon atoms, cyclic alkyl having 3-20 carbon atoms, straight-chain alkoxy having 1-20 carbon atoms, branched-chain alkoxy having 3-20 carbon atoms, cyclic alkoxy having 3-20 carbon atoms, straight-chain alkylthio having 1-20 carbon atoms, branched-chain alkylthio having 3-20 carbon atoms, cyclic alkylthio having 3-20 carbon atoms; m is selected from an integer ≥0; q is selected from an integer ≥0.

6. The organic compound containing cyano-substituted 1,3-indandione according to any one of claims 1 to 4, characterized in that: Said R3 and R4 are independently selected from , where R 110 Each occurrence is independently selected from a straight chain alkyl group having 1 to 30 carbon atoms, or a branched chain alkyl group having 3 to 30 carbon atoms; R c Each occurrence is independently selected from -D, -F, -CF3, -Cl, -Br, -I, cyano, nitro, a cyclic alkyl group having 3-10 carbon atoms, an aromatic group having 6-10 carbon atoms, a heteroaromatic group having 5-10 ring atoms, or a group formed by a combination of the above groups; r is selected from an integer ≥0.

7. The organic compound containing cyano-substituted 1,3-indandione according to claim 1, characterized in that: The organic compound is selected from the following structures: 。 8. A mixture, characterized in that: The mixture comprises the organic compound containing cyano-substituted 1,3-indandione as claimed in any one of claims 1 to 7, and at least another organic functional material.

9. A composition, characterized in that: The composition comprises the organic compound containing a cyano-substituted 1,3-indandione according to any one of claims 1 to 7 or the mixture according to claim 8, and at least one organic solvent.

10. An organic electronic device, characterized in that: The organic electronic device comprises the organic compound containing cyano-substituted 1,3-indandione according to any one of claims 1 to 7 or the mixture according to claim 8, or is prepared from the composition according to claim 9.

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