Amine organic compound and organic photovoltaic cell

Abstract

The present application relates to the technical field of organic photovoltaics, and particularly relates to an amine organic compound and an organic photovoltaic cell. The aromatic amine side chain can effectively regulate the absorption and chemical energy level of the acceptor material, can form good optical absorption complementation with the donor and the host acceptor, can make full use of the sunlight, and can be applied to the organic photovoltaic cell as the third component acceptor material, so that the performance of the cell can be comprehensively improved.

Description

Technical Field

[0001] This invention relates to the field of organic photovoltaic technology, specifically to an amine organic compound and an organic photovoltaic cell. Background Technology

[0002] Fossil fuels such as oil, natural gas, and coal, as essential resources for human survival, have driven the material progress and technological development of human society over the past few centuries. However, as non-renewable fossil fuels, their continuous consumption has exacerbated the energy crisis and environmental pollution. Therefore, the development of a sustainable and renewable clean energy source is urgently needed. Solar energy, with its abundant resources, wide distribution, and clean, pollution-free nature, has become the most ideal alternative energy source.

[0003] The development of photovoltaic (PV) cells can be broadly divided into three generations. The first generation consists of silicon-based solar cells, primarily based on monocrystalline and polycrystalline silicon. This type of PV cell technology is mature and has the highest market share. The second generation consists of thin-film PV cells, mainly based on copper indium selenide (CIGS), copper indium gallium selenide (CIGS), and cadmium telluride (CdTe). The third generation is represented by dye-sensitized photovoltaics (DSPV), perovskite photovoltaics (PSPV), and organic photovoltaics (OPP). Compared to other types of PV cells, organic PV cells have become a current research hotspot due to their easily tunable absorption spectra, light weight, flexibility, low cost, and environmental friendliness. Currently, through optimization using molecular engineering and device engineering strategies, the energy conversion efficiency of organic PV cells has exceeded 20%, demonstrating enormous development potential.

[0004] Ternary organic photovoltaic cells are based on binary cells, with the introduction of a third component with suitable absorption, chemical energy levels, and optimized morphology into the active layer. This aims to enhance photon absorption, improve charge transport, and optimize crystallinity and active layer morphology, thereby increasing device efficiency. The third component typically has complementary optical absorption to the host donor (acceptor) material, increasing photon absorption and utilization. Furthermore, the energy levels of the third component can form gradient energy levels with the host donor (acceptor) material, promoting rapid electron and hole transport. Additionally, the third component can form an "alloy" phase with the host material or create energy (charge) transfer channels, further promoting charge transport. Therefore, the rational selection of the building block design for the third component material structure is crucial for improving the performance of ternary organic photovoltaic cells. Side-chain engineering, a commonly used and effective strategy in molecular design, can regulate compound absorption, energy levels, mobility, and molecular packing. Commonly used side-chain groups are primarily aliphatic chains or aromatic ring side chains. Compared with the aforementioned groups, aromatic amine side chains have the following advantages: 1. The nitrogen atom in diphenylamine has a lone pair of electrons, making it a strong electronic unit. As a side chain, it can increase the LUMO energy level of the compound through inductive or conjugation effects, thereby improving the open-circuit voltage; 2. Diphenylamine side chains have a large-volume and rigid three-dimensional structure, which can suppress excessive aggregation. The large steric hindrance can prevent the excessively dense packing of small molecule acceptors and avoid the formation of excessively large crystal domains; 3. Diphenylamine itself is a commonly used antioxidant group, which can capture free radicals and slow down the degradation of materials under light / oxygen, thus helping to improve the operational stability of devices. Currently, there are few reports on the introduction of diphenylamine and its derivative aromatic amines as side chains into fused-ring acceptors. Given the above advantages, the rational design of acceptor molecules containing aromatic amine side chains can improve the basic photoelectric properties and molecular packing of acceptor molecules. Using them as a third component is expected to prepare more efficient organic photovoltaic cells, which is of great significance for further improving the efficiency of organic photovoltaic cells. Summary of the Invention

[0005] Based on this, the purpose of this invention is to develop a novel amine organic compound and apply it as a third-component acceptor material in organic photovoltaic cells, thereby achieving a comprehensive improvement in cell performance.

[0006] This invention provides an amine organic compound, wherein the amine organic compound is selected from the structure shown in formula (I):

[0007]

[0008] in:

[0009] R1, R2, and R3 are each independently selected from substituted or unsubstituted alkyl groups having 1-30 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or substituted or unsubstituted aromatic groups having 6-20 carbon atoms.

[0010] Each time Y1 and Y2 appear, they are independently selected from O, S, or Se;

[0011] Each time M appears, it is independently selected from O or C(CN)2;

[0012] Ar1, Ar2, and Ar3 each time they appear, are independently selected from substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or substituted or unsubstituted aromatic groups having 6-20 carbon atoms.

[0013] The term "substituted or unsubstituted" indicates 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 one or more of the following groups: -D, -F, -Cl, -Br, -I, -CN, -CF3, alkyl groups having 1-20 carbon atoms, alkoxy groups having 1-20 carbon atoms, alkylthio groups having 1-20 carbon atoms, heteroaromatic groups having 5-20 ring atoms, and aromatic groups having 6-20 carbon atoms.

[0014] In an alternative embodiment, each occurrence of R1 is independently selected from either a substituted or unsubstituted straight-chain alkyl group having 6-30 carbon atoms, or a substituted or unsubstituted branched alkyl group having 6-30 carbon atoms.

[0015] Furthermore, each occurrence of R1 is independently selected from one or more R... a A straight-chain alkyl group having 8-30 carbon atoms, substituted or unsubstituted, or containing one or more R... a Substituted or unsubstituted branched alkyl groups having 8-30 carbon atoms; said R a Each occurrence is a group formed by a combination of one or more groups selected independently from -F, -Cl, -Br, -I, -CN, -CF3, cyclic alkyl groups having 3-10 carbon atoms, heteroaromatic groups having 5-10 ring atoms, and aromatic groups having 6-10 carbon atoms.

[0016] Furthermore, each occurrence of R1 is independently selected from branched alkyl groups having 6-20 carbon atoms.

[0017] In an optional embodiment, each occurrence of R2 and R3 is independently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or substituted or unsubstituted aromatic groups having 6-20 carbon atoms.

[0018] Furthermore, each occurrence of R2 and R3 is independently selected from straight-chain alkyl groups having 1-20 carbon atoms, branched alkyl groups having 3-20 carbon atoms, cyclic alkyl groups having 3-20 carbon atoms, straight-chain alkoxy groups having 1-20 carbon atoms, branched alkoxy groups having 3-20 carbon atoms, straight-chain alkylthio groups having 1-20 carbon atoms, branched alkylthio groups having 3-20 carbon atoms, and groups influenced by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-10 ring atoms, or containing one or more R... b Aromatic groups having 6-10 carbon atoms, substituted or unsubstituted; the R b Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, -CF3, straight-chain alkyl with 1-20 carbon atoms, branched alkyl with 3-20 carbon atoms, cyclic alkyl with 3-20 carbon atoms, straight-chain alkoxy with 1-20 carbon atoms, branched alkoxy with 3-20 carbon atoms, straight-chain alkylthio with 1-20 carbon atoms, or branched alkylthio with 3-20 carbon atoms.

[0019] Furthermore, each occurrence of R2 and R3 is independently selected from straight-chain alkyl groups having 1-10 carbon atoms, or groups containing one or more R atoms. b Substituted or unsubstituted thiophene group, or substituted with one or more R groups b Substituted or unsubstituted phenyl groups.

[0020] In one specific embodiment, each occurrence of R2 and R3 is independently selected from any of the following groups:

[0021] *-CH3、

[0022]

[0023] In one embodiment, R2 and R3 are selected from the same group.

[0024] In another embodiment, R2 and R3 are selected from different groups.

[0025] In one embodiment, Ar1 is selected from one or more R c Substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms, or containing one or more R... c Aromatic groups having 6-20 carbon atoms, substituted or unsubstituted; said R cEach occurrence is a group formed independently from one or more of the following groups: -D, -F, -Cl, -Br, -I, -CN, -CF3, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, cyclic alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched alkoxy with 3-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, branched alkylthio with 3-10 carbon atoms, heteroaromatic group with 5-20 ring atoms, and aromatic group with 6-20 carbon atoms.

[0026] Furthermore, the Ar1 is selected from any of the following groups:

[0027]

[0028] Wherein: Z is selected independently from O, S or Se each time it appears;

[0029] Each time X appears, it is independently selected from N or CR4;

[0030] Each time R4 appears, it is independently selected from one or more of the following groups: -H, -D, -F, -Cl, -Br, -I, -CN, -CF3, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, cyclic alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched alkoxy with 3-10 carbon atoms, straight-chain alkathiol with 1-10 carbon atoms, branched alkathiol with 3-10 carbon atoms, heteroaromatic group with 5-20 cyclic atoms, and aromatic group with 6-20 carbon atoms.

[0031] # indicates a fusion site, which is selected from C atoms.

[0032] In an alternative embodiment, the Selected from

[0033] In an alternative embodiment, the Selected from

[0034] In an alternative embodiment, the Selected from Preferably, the Each time R4 appears, it is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, or -CF3.

[0035] In an alternative embodiment, the Selected from

[0036] In an alternative embodiment, the Selected from Preferably, the Each time R4 appears, it is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, or -CF3.

[0037] In an alternative embodiment, the Selected from Preferably, the Each time R4 appears, it is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, or -CF3.

[0038] In an alternative embodiment, Y1 is selected from S.

[0039] In an alternative embodiment, Y2 is selected from S or Se.

[0040] In an alternative embodiment, the Selected from The asterisk (*) indicates a connection site.

[0041] In an alternative embodiment, the Selected from

[0042] Furthermore, each occurrence of Ar2 and Ar3 is independently selected from one or more R... d The R group may be a substituted or unsubstituted heteroaromatic group having 5-20 ring atoms, or a substituted or unsubstituted aromatic group having 6-20 carbon atoms; d Each occurrence is a group formed independently of one or at least two of the following groups: -D, -F, -Cl, -Br, -I, -CN, -CF3, alkyl groups having 1-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, alkylthio groups having 1-10 carbon atoms, heteroaromatic groups having 5-10 ring atoms, and aromatic groups having 6-10 carbon atoms.

[0043] Furthermore, each occurrence of Ar2 and Ar3 is independently selected from one or more R... d The R group may be a substituted or unsubstituted heteroaromatic group having 5-10 ring atoms, or a substituted or unsubstituted aromatic group having 6-10 carbon atoms; d Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, -CF3, alkyl groups having 1-6 carbon atoms, or alkoxy groups having 1-6 carbon atoms.

[0044] In a specific embodiment, each occurrence of Ar2 and Ar3 is independently selected from any of the following groups:

[0045]

[0046] Where: m1 is selected from 0, 1 or 2; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0047] In one specific embodiment, the Independently selected from any of the following groups:

[0048]

[0049] In one specific embodiment, the amine organic compound according to this application is selected from any of the following structures, but is not limited thereto:

[0050]

[0051]

[0052]

[0053]

[0054] The present invention further relates to a mixture comprising an amine organic compound as described above and at least one other organic functional material, wherein the other organic functional material is selected from a photoactive layer donor material or a photoactive layer acceptor material.

[0055] In one embodiment, the mixture according to the present invention comprises an amine organic compound as described above and at least one photoactive layer donor material.

[0056] Furthermore, the photoactive layer donor material is selected from polymer donor materials. The polymer donor material can be selected from polythiophene material systems, such as P3AT, P3HT, P3OT, P3DDT, etc.; fluorene-containing polymer material systems, such as PF8BT, etc.; novel structural narrow bandgap polymer material systems, such as copolymers of benzodithiophene (BDT), benzothiadiazoles (BT, BBT), quinoxalines (QU, PQ), pyrazines (TP, PQ) and electron-rich groups (such as thiophene derivatives), such as PM6, PM7, PBDB-T, D18, D18-Cl, PTQ10, PTQ11, PBQx-TCl, PBQx-TF, PB2, PCE10, and copolymers containing them, but is not limited thereto.

[0057] The present invention further relates to a composition comprising an amine organic compound or mixture as described above, and at least one organic solvent.

[0058] The organic solvent is selected from, but not limited to: tetrahydronaphthalene, 1,5-dimethyltetrahydrofuran, methyltetrahydrofuran, decahydronaphthalene, chlorobenzene, o-dichlorobenzene, 1,2,4-trichlorobenzene, 1,4-dimethylnaphthalene, toluene, o-xylene, m-xylene, p-xylene, mesitylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, acetophenone, diphenyl ether, 2-methylthiophene, 3-methylthiophene, monochloromethane, dichloromethane, chloroform, dichloroethylene, trichloroethylene, 1,1,1- The following are some of the following: trichlorotrifluoroethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, carbon tetrachloride, tetrahydrofuran, anisole, 2,4-dimethylanisole, 1-methylnaphthalene, morpholine, 1,4-dioxane, N-methylpyrrolidone, acetone, cyclopentanone, cyclohexanone, methyl ethyl ketone, ethyl acetate, n-butyl acetate, carbon disulfide, carbon tetrachloride, N,N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, indane, methyl benzoate, ethyl benzoate, acetonitrile, and hexamethylphosphoramide, or a mixture of two or more of these.

[0059] The present invention further relates to an organic photovoltaic cell comprising a cathode, an anode, and a photoactive layer located between the cathode and the anode, the photoactive layer comprising, as described above, an amine organic compound or mixture thereof, or prepared from the above-described composition.

[0060] In one embodiment, the photoactive layer material comprises a photoactive layer donor material and a photoactive layer acceptor material, wherein the photoactive layer acceptor material comprises an amine organic compound as described above.

[0061] Furthermore, the photoactive layer donor material is a polymer donor material. The polymer donor material can be selected from polythiophene material systems, such as P3AT, P3HT, P3OT, P3DDT, etc.; fluorene-containing polymer material systems, such as PF8BT, etc.; novel structural narrow bandgap polymer material systems, such as benzodithiophene (BDT), benzothiadiazoles (BT, BBT), quinoxalines (QU, PQ), pyrazines (TP, PQ), and copolymers containing electron-rich groups (such as thiophene derivatives), such as PM6, PM7, PBDB-T, D18, D18-Cl, PTQ10, PTQ11, PBQx-TCl, PBQx-TF, PB2, PCE10, and copolymers containing them, but is not limited thereto. Further reference can be made regarding the selection of the active layer donor material: Chem. Rev. 2022, 122, 18, 14180–14274.

[0062] The method for preparing the photoactive layer material solution is as follows: the photoactive layer donor material and acceptor material are dissolved in an organic solvent at a certain mass ratio, and the mixture is stirred until fully dissolved to obtain the photoactive layer solution. The organic solvent is described as above.

[0063] The above solution is used to prepare the photoactive layer by printing or coating methods. These printing or coating methods can include, but are not limited to, 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, and slot-loaded extrusion coating. Slot-loaded coating, spin coating, and inkjet printing are preferred.

[0064] The preferred mass ratio of the photoactive layer donor material to the acceptor material in the organic solvent is 1:0.8 to 1:1.5; further, the preferred mass ratio of the photoactive layer donor material to the acceptor material in the organic solvent is 1:1 to 1:1.5; the preferred mass ratio of the photoactive layer donor material to the acceptor material in the organic solvent is 1:1 to 1:1.2.

[0065] The concentration of the photoactive layer donor material in the organic solvent is preferably 3 to 15 mg / mL; further, the concentration of the photoactive layer donor material in the organic solvent is preferably 4 to 10 mg / mL.

[0066] Furthermore, the photoactive layer material solution may further include additives for adjusting viscosity, film-forming properties, and improving adhesion. The additives may be selected from, but are 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 to these.

[0067] At least one of the anode and cathode is transparent or translucent to facilitate light incidence. 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 pastes, graphene, carbon nanotubes; 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 PEDOT:PSS, polypyrrole, and polyaniline; or materials with multilayer structures such as LiF / Al, LiO2 / Al, LiF / Fe, MoO3 / Al, Al:Li, Al:BaF2, and Al:BaF2:Ba, but not limited to these.

[0068] In one embodiment, the organic photovoltaic cell comprises an anode, an anode buffer layer, a photoactive layer, a cathode buffer layer, and a cathode stacked sequentially, wherein the photoactive layer comprises an amine organic compound or mixture as described above.

[0069] Preferably, the cathode buffer layer material can be selected from low work function metal complexes, metal oxides, metal salts, etc., such as metal complexes of 8-hydroxyquinoline, complexes containing Alq3, metal complexes containing Liq, PEI-Zn, LiF, Ca, and titanium oxide (TiO2). x It can be zinc oxide (ZnO), cesium carbonate (Cs2CO3), etc.; it can also be polymer materials, such as PFN-Br or PFN or PDINN or PDINO or PNDIT-F3N-Br or PNDIT-F3N, etc., but is not limited to these.

[0070] The anode buffer layer material is selected from PEDOT:PSS and molybdenum oxide (MoO). x ), vanadium oxide (V₂O₅), nickel oxide (NiO), tungsten oxide (WO₂) x Preferably, x is selected from 2 or 3), small molecule self-assembled materials such as 2PACz, MeO-2PACz, Cbz-2Ph, etc., but not limited to these.

[0071] It should be noted that, in order to improve the performance of organic photovoltaic cell devices, the organic photovoltaic cell may further include other functional layers, including but not limited to charge blocking layers and charge transport layers.

[0072] Furthermore, the organic photovoltaic cell also includes a substrate. In one embodiment, the substrate is disposed on the anode side and away from the photoactive layer. In another embodiment, the substrate is disposed on the cathode side and away from the photoactive layer.

[0073] In one embodiment, a substrate with excellent transparency, surface smoothness, ease of handling, and water resistance can be used as the substrate. Specifically, a glass substrate, a thin-film glass substrate, or a transparent plastic substrate can be used. The plastic substrate may include, but is not limited to, single-layer or multi-layer films such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), parylene, etc., and substrates commonly used in organic solar cells may also be used.

[0074] In an alternative embodiment, the organic photovoltaic cell according to the present invention is selected from indoor organic photovoltaic cells.

[0075] The indoor organic photovoltaic system described in this invention is mainly applied in fields such as smart IoT and smart homes.

[0076] The amine organic compounds of this invention are introduced onto the large fused ring core unit. unit, The nitrogen atom possesses a lone pair of electrons, which, when attached as a side chain, can raise the LUMO energy level of the compound through inductive or conjugation effects. Furthermore, With its large volume and rigid three-dimensional structure, it can suppress excessive aggregation, and the large spatial steric hindrance can prevent the main chain from being too tightly packed, thus avoiding the formation of excessively large crystal domains.

[0077] The amine organic compounds described in this invention, when used as acceptor materials in combination with suitable donor materials in organic photovoltaic cells, exhibit excellent photoelectric performance. This is because: the aromatic amine side chains can effectively regulate the absorption and chemical energy levels of the acceptor material, forming good optical absorption complementarity with the donor and the host acceptor, thus fully utilizing solar photons; secondly, the aromatic amine side chains can enhance the LUMO energy level of the acceptor molecule, increasing the device voltage; finally, the aromatic amine groups with a certain locating effect can significantly inhibit the excessive aggregation of active layer molecules, forming a good nano-interpenetrating network structure, which is beneficial to improving charge transport and device performance. Attached Figure Description

[0078] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0079] Figure 1 The NMR spectrum of compound (16) in synthesis example (3).

[0080] Figure 2 The thin film absorption spectrum of compound (16) is shown.

[0081] Figure 3 The electrochemical curve of compound (16) is shown.

[0082] Figure 4 This is a schematic diagram of the structure of an embodiment of the organic photovoltaic cell device of the present invention. Detailed Implementation

[0083] 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. All other embodiments obtained by those skilled in the art based on the described embodiments of the present invention without inventive effort are within the scope of protection of this invention.

[0084] 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").

[0085] In this invention, organic photovoltaic devices, organic solar cells, OPV, and OSC have the same meaning and can be used interchangeably.

[0086] In this invention, the terms "photoactive layer" and "active layer" have the same meaning and can be used interchangeably.

[0087] 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.

[0088] In this invention, "substitution" means that one or more hydrogen atoms in the substituent are replaced by the substituent.

[0089] 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. In aromatic groups, the ring atom number is the same as the carbon atom number; in heteroaromatic groups, the ring atom number is the carbon atom number plus the heteroatom number; for example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, the ring atom number of a quinoline ring is 10, the ring atom number of a thiophene group is 5, and the ring atom number of a thiophene is 8.

[0090] In this invention, "aromatic group" refers to any optional functional group or substituent derived from an aromatic carbide 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 aromatic groups in this application. Preferably, the aromatic group 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, anthracene, phenanthryl, fluoranthracene, and their derivatives.

[0091] In this invention, a "heteroaromatic group" refers to a heteroaromatic ring or its derivative containing one, two, three, four, five, six or more heteroatoms, wherein 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. The term "heteroaromatic group" as used herein also includes groups formed by the fusion of one or more heteroaromatic groups with one or more aromatic rings, aliphatic rings or heterocycles. Preferably, the heteroaromatic group is selected from those having 5-20 ring atoms; more preferably, it is selected from those having 5-10 ring atoms. Heteroaromatic groups include, but are not limited to: thiophene, furanyl, pyrrolyl, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiophene, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrryl, thienopyrryl, thienothiophene, furanol, furanol, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazanaphthyl, phenanthridine, primidyl, quinazolinone, dibenzothiophene, dibenzofuranyl, carbazole, phenazinyl and their derivatives.

[0092] In this invention, the number of carbon atoms in a straight-chain alkyl group can be 1 to 30, 1 to 20, 1 to 16, 1 to 10, or 1 to 6. The number of carbon atoms in a branched-chain alkyl group can be 3 to 30, 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Non-limiting examples of straight-chain alkyl groups include methyl (-CH3), ethyl (-C2H5), n-propyl (-C3H7), n-butyl (-C4H9), and n-pentyl (-C5H9). 11 ), n-hexyl (-C6H) 13 ), heptyl (-C7H) 15 ), n-octyl (-C8H) 17 ), non-nonyl (-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 33Non-limiting examples of branched alkyl groups include: isopropyl, branched alkyl groups containing 4 carbon atoms, branched alkyl groups containing 5 carbon atoms, branched alkyl groups containing 6 carbon atoms, branched alkyl groups containing 7 carbon atoms, branched alkyl groups containing 8 carbon atoms, branched alkyl groups containing 9 carbon atoms, branched alkyl groups containing 10 carbon atoms, branched alkyl groups containing 11 carbon atoms, branched alkyl groups containing 12 carbon atoms, branched alkyl groups containing 13 carbon atoms, branched alkyl groups containing 14 carbon atoms, branched alkyl groups containing 15 carbon atoms, and branched alkyl groups containing 16 carbon atoms.

[0093] 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. The straight-chain alkoxy means that the alkyl group in "-O-alkyl" is selected from straight-chain alkyl groups, wherein the number of carbon atoms in the straight-chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the branched-chain alkoxy means that the alkyl group in "-O-alkyl" is selected from branched-chain alkyl groups, wherein the number of carbon atoms in the branched-chain alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6.

[0094] The term "alkoxythio" 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. The straight-chain alkoxythio group indicates that the alkyl group in the "-S-alkyl" is selected from straight-chain alkyl groups, wherein the number of carbon atoms in the straight-chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6; the branched-chain alkoxythio group indicates that the alkyl group in the "-S-alkyl" is selected from branched-chain alkyl groups, wherein the number of carbon atoms in the branched-chain alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] In describing the structural elements of the present invention, the terms "comprising" or "including" or similar terms used in the present invention mean that the device or material preceding the word covers the device or material listed after the word and its equivalents, but does not exclude other devices or materials.

[0099] In the description of this invention, it should be understood that the terms "upper," "lower," "between layers," etc., indicate the orientation or positional relationship based on the orientation or positional relationship shown in the drawings, or the orientation or positional relationship commonly used when organic solar cell devices are in use, or the orientation or positional relationship commonly understood by those skilled in the art. They are only used to facilitate the description of this invention and to simplify the description, and are not intended to indicate or imply that the device or element referred to must have a specific orientation, or be constructed and operated in a specific orientation. Therefore, they should not be construed as limiting this invention.

[0100] 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 groups listed.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] Examples of Amine Compound Synthesis

[0105] The following embodiments are provided to facilitate a better understanding of the disclosure of this invention, but are not intended to limit it in any way. Unless otherwise specified, the experimental methods used in the following embodiments are conventional methods, and the materials and reagents used are prior art and commercially available unless otherwise specified.

[0106] Synthesis Example 1: Synthesis of Compound (1)

[0107]

[0108] Synthesis of compound 1-1:

[0109] Under nitrogen protection, 3-bromothiophene[3,2-b]thiophene (3 g, 13.69 mmol), dihexylamine (2.79 g, 15.06 mmol), and sodium tert-butoxide (3.94 g, 41.07 mmol) were added to 30 mL of o-xylene. After purging with nitrogen for 30 min, tris(dibenzylacetone) palladium (375.4 mg, 0.41 mmol) and 2-biscyclohexylphosphine-2′,6′-dioxane were rapidly added. Methoxybiphenyl (S-Phos) (337.2 mg, 0.821 mmol) was reacted under reflux at 110 °C for 12 h. After cooling, dichloromethane and water were added to the liquid phase for extraction. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was then separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent, yielding approximately 1.33 g of compound 1-1. Yield: 30.1%, MS: 323.66.

[0110] Synthesis of compounds 1-2:

[0111] Under a nitrogen atmosphere, compound 1-1 (1 g, 3.09 mmol) and anhydrous THF (20 mL) were added to a 50 mL single-necked flask. n-BuLi (1.35 mL, 3.39 mmol, 2.5 M) was added dropwise at -75 °C. After stirring for 1 h, tributyltin chloride (1.5 g, 4.63 mmol) was added dropwise at -75 °C. The mixture was then slowly brought to room temperature and stirred overnight. After the reaction was complete, the reaction was quenched with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The product did not require purification and was directly added to the next step to obtain approximately 1.35 g of compound 1-2, yield 71.2%, MS: 613.24.

[0112] Synthesis of compounds 1-3:

[0113] Under nitrogen protection, compounds 1-2 (1.05 g, 1.71 mmol) and 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (300 mg, 0.78 mmol) were added to 15 mL of toluene and stirred. After purging with nitrogen for 30 min, tetrakis(triphenylphosphine)palladium (58.95 mg, 0.051 mmol) was quickly added. The reaction was refluxed at 110 °C for 12 h. After cooling, potassium fluoride solution was added, and stirring was continued for 20 min. The insoluble solids were filtered off, and the product was extracted with dichloromethane and water in the liquid phase. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was then separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. The product yielded approximately 528 mg of compounds 1-3, yield: 77.9%, MS: 869.11.

[0114] Synthesis of compounds 1-4:

[0115] Under nitrogen protection, compounds 1-3 (500 mg, 0.575 mmol) and triphenylphosphine (603.2 mg, 2.3 mmol) were sequentially added to a 100 mL three-necked flask containing o-dichlorobenzene. The temperature was raised to 180 °C and reacted for 12 h. After the reactants were completely reacted, the mixture was cooled to room temperature. Then, dichloromethane and water were added to the liquid phase for extraction. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was then separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. Approximately 325 mg of compounds 1-4 were obtained, yield: 70.1%, MS: 805.69.

[0116] Synthesis of compounds 1-5:

[0117] Under nitrogen protection, compounds 1-4 (300 mg, 0.37 mmol), potassium carbonate (308.9 mg, 2.23 mmol), and potassium iodide (370.1 mg, 2.23 mmol) were sequentially added to a three-necked flask containing 50 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, isooctane bromo (178.6 mg, 0.925 mmol) was added dropwise. The temperature was raised to 85 °C and the reaction was carried out overnight. After the reactants had reacted completely, the temperature was lowered to room temperature. Then, dichloromethane and water were added to the liquid phase for extraction. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was then separated by silica gel column chromatography using a mixed solvent of dichloromethane and petroleum ether as the eluent. Approximately 305 mg of compounds 1-5 were obtained, yield: 80.1%, MS: 1029.15.

[0118] Synthesis of compounds 1-6

[0119] Under a nitrogen atmosphere, compounds 1-5 (250 mg, 0.242 mmol) were added to a 100 mL three-necked flask, followed by approximately 5 mL of anhydrous DMF. After purging with nitrogen three times, 2 mL of phosphorus oxychloride was added in an ice bath and the mixture was stirred for 10 min. The mixture was then heated to 90 °C and reacted overnight. After the starting materials had completely reacted, the mixture was cooled to room temperature, and sodium hydroxide solution was added. The mixture was stirred for another 10 min, followed by extraction with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was then separated by silica gel column chromatography using a mixture of dichloromethane and petroleum ether as the eluent. Approximately 198 mg of compounds 1-6 were obtained, yield: 75.4%, MS: 1085.73.

[0120] Synthesis of compound (1):

[0121] Under a nitrogen atmosphere, compounds 1-6 (150 mg, 0.138 mmol) and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-yl)malononitrile (159 mg, 0.69 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The mixture was heated to 65 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and water. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was then separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. The product was recrystallized twice with methanol to finally obtain approximately 133 mg of compound (1), yield: 63.8%, MALDI-TOF-MS: 1509.80.

[0122] Synthesis Example 2: Synthesis of Compound (5)

[0123]

[0124] Synthesis of compound 2-1:

[0125] Under nitrogen protection, compound 1-1 (1.09 g, 1.78 mmol) and 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]selenodiazole (350 mg, 0.812 mmol) were added to 15 mL of toluene and stirred. After purging with nitrogen for 30 min, tetrakis(triphenylphosphine)palladium (61.73 mg, 0.053 mmol) was quickly added. The subsequent synthetic steps were the same as those for compound (1-3), yielding approximately 620 mg of compound 2-1, yield: 83.3%, MS: 916.51.

[0126] Synthesis of compound 2-2:

[0127] Under nitrogen protection, compound 2-1 (500 mg, 0.545 mmol) and triphenylphosphine (572.5 mg, 2.18 mmol) were added sequentially to a 250 mL three-necked flask containing o-dichlorobenzene. The subsequent synthetic reaction steps were the same as those for compounds (1-4). The product 2-2 was obtained in approximately 316 mg, yield: 68.0%, MS: 852.79.

[0128] Synthesis of compounds 2-3:

[0129] Under nitrogen protection, compound 2-2 (300 mg, 0.352 mmol), potassium carbonate (291.6 mg, 2.11 mmol), and potassium iodide (350.2 mg, 2.11 mmol) were added sequentially to a three-necked flask containing 50 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, bromoisooctane (169.9 mg, 0.88 mmol) was added dropwise. The subsequent synthetic reaction steps were the same as those for compounds (1-5), yielding approximately 287 mg of compound 2-3, yield: 75.7%, MS: 1076.58.

[0130] Synthesis of compounds 2-4:

[0131] Under a nitrogen atmosphere, compound 2-3 (250 mg, 0.232 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6). About 200 mg of compound 2-4 was obtained, yield: 76.1%, MALDI-TOF-MS: 1132.97.

[0132] Synthesis of compound (5):

[0133] Under a nitrogen atmosphere, compounds 2-4 (180 mg, 0.158 mmol) and 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1-yl)malononitrile (209 mg, 0.794 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthetic reaction steps were the same as those for compound (1). Finally, approximately 171 mg of compound (5) was obtained, with a yield of 66.7% and a MALDI-TOF-MS value of 1622.50.

[0134] Synthesis Example 3: Synthesis of Compound (16)

[0135]

[0136] Synthesis of compound 3-1:

[0137] Under nitrogen protection, 3-bromothiophene[3,2-b]thiophene (40 g, 0.18 mol), bis(4-(tert-butyl)phenyl)amine (56.5 g, 0.2 mol), and sodium tert-butoxide (52.6 g, 0.54 mol) were added to 30 mL of o-xylene. After purging with nitrogen for 30 min, tridibenzylacetone dipalladium (5 g, 5.47 mmol) and 2-biscyclohexylphosphine-2′,6′-dimethoxybiphenyl (S-Phos) (4.49 g, 10.9 mmol) were rapidly added. The subsequent synthetic steps were the same as those for compound (1-1). The product of compound 3-1 was obtained in approximately 49.8 g, yield: 65.1%, MS: 419.32.

[0138] Synthesis of compound 3-2:

[0139] Under a nitrogen atmosphere, compound 3-1 (20 g, 47.6 mmol) and anhydrous THF (200 mL) were added to a 500 mL single-necked flask. n-BuLi (20.9 mL, 52.4 mmol, 2.5 M) was added dropwise at -75 °C. After stirring for 1 h, tributyltin chloride (23.2 g, 71.4 mmol) was added dropwise at -75 °C. The subsequent synthesis steps were the same as those for compound (1-2). The product 3-2 was obtained in approximately 23.7 g, yield 70.3%, MS: 708.49.

[0140] Synthesis of compound 3-3:

[0141] Under nitrogen protection, compound 3-2 (12.1 g, 17.1 mmol) and 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (3 g, 7.81 mmol) were added to 150 mL of toluene and stirred. After purging with nitrogen for 30 min, tetra(triphenylphosphine)palladium (593.0 mg, 0.51 mmol) was quickly added. The subsequent synthetic steps were the same as those for compound (1-3). The product 3-3 was obtained in approximately 6.9 g, yield: 83.2%, MS: 1061.38.

[0142] Synthesis of compounds 3-4:

[0143] Under nitrogen protection, compound 3-3 (5 g, 4.71 mmol) and triphenylphosphine (4.94 g, 18.8 mmol) were added sequentially to a 250 mL three-necked flask containing o-dichlorobenzene. The subsequent synthetic reaction steps were the same as those for compounds (1-4). Approximately 3.15 g of compound 3-4 was obtained, yield: 67.0%, MS: 997.84.

[0144] Synthesis of compounds 3-5:

[0145] Under nitrogen protection, compounds 3-4 (300 mg, 0.30 mmol), potassium carbonate (249.4 mg, 1.8 mmol), and potassium iodide (298.8 mg, 1.8 mmol) were sequentially added to a three-necked flask containing 50 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, bromoisooctane (144.8 mg, 0.75 mmol) was added dropwise. The subsequent synthesis steps were the same as those for compounds (1-5). Approximately 267 mg of compound 3-5 was obtained, yield: 72.8%, MALDI-TOF-MS: 1221.72.

[0146] Synthesis of compounds 3-6:

[0147] Under a nitrogen atmosphere, compound 3-5 (250 mg, 0.204 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6). About 221 mg of compound 3-6 was obtained, yield: 84.8%, MALDI-TOF-MS: 1278.03.

[0148] Synthesis of compound (16):

[0149] Under a nitrogen atmosphere, compounds 3-6 (200 mg, 0.156 mmol) and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-yl)malononitrile (90.05 mg, 0.391 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthetic steps were the same as those for compound (1). The final product was approximately 166 mg of compound (16), yield: 62.5%, MALDI-TOF-MS: 1701.94.

[0150] Synthesis Example 4: Synthesis of Compound (21)

[0151]

[0152] Synthesis of compound 4-1:

[0153] Under nitrogen protection, compounds 3-4 (2.4 g, 2.4 mmol), potassium carbonate (1.98 g, 14.4 mmol), and potassium iodide (2.39 g, 14.4 mmol) were sequentially added to a three-necked flask containing 100 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, 5-(bromomethyl)undecane (1.49 g, 6 mmol) was added dropwise. The subsequent synthetic reaction steps were the same as those for compounds (1-5), yielding approximately 2.25 g of compound 4-1, yield: 70.7%, MALDI-TOF-MS: 1334.8.

[0154] Synthesis of compound 4-2:

[0155] Under a nitrogen atmosphere, compound 4-1 (250 mg, 0.187 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6), yielding about 221 mg of compound 4-2, yield: 85.2%, MALDI-TOF-MS: 1390.22.

[0156] Synthesis of compound (21):

[0157] Under a nitrogen atmosphere, compound 4-2 (200 mg, 0.143 mmol) and 2-(6,7-difluoro-3-oxo-2,3-dihydro-1H-cyclopentenon[b]naphthalene-1-yl)malononitrile (100.79 mg, 0.359 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthetic steps were the same as those for compound (1-), and the final product (21) was approximately 170 mg, yield: 62.3%, MALDI-TOF-MS: 1914.35.

[0158] Synthesis Example 5: Synthesis of Compound (25)

[0159]

[0160] Synthesis of compound 5-1:

[0161] Under nitrogen protection, 3-bromothiophene[3,2-b]thiophene (4 g, 18.25 mmol), bis(4-hexylphenyl)amine (6.77 g, 20.08 mmol), and sodium tert-butoxide (5.26 g, 54.75 mmol) were added to 30 mL of o-xylene. After purging with nitrogen for 30 min, tridibenzylacetone dipalladium (501.3 mg, 0.547 mmol) and 2-biscyclohexylphosphine-2′,6′-dimethoxybiphenyl (S-Phos) (449.5 mg, 1.09 mmol) were rapidly added. The subsequent synthetic steps were the same as those for compound (1-1). The product of compound 5-1 was obtained in approximately 5.89 g, yield: 67.8%, MS: 476.15.

[0162] Synthesis of compound 5-2:

[0163] Under a nitrogen atmosphere, compound 5-1 (2 g, 4.2 mmol) and anhydrous THF (20 mL) were added to a 50 mL single-necked flask. n-BuLi (1.84 mL, 4.62 mmol, 2.5 M) was added dropwise at -75 °C. After stirring for 1 h, tributyltin chloride (2.05 g, 6.3 mmol) was added dropwise at -75 °C. The subsequent synthesis steps were the same as those for compound (1-2). Approximately 2.67 g of compound 5-2 was obtained, with a yield of 83.1% and MS: 765.33.

[0164] Synthesis of compound 5-3:

[0165] Under nitrogen protection, compound 5-2 (1.75 g, 2.29 mmol) and 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (400 mg, 1.04 mmol) were added to 15 mL of toluene and stirred. After purging with nitrogen for 30 min, tetra(triphenylphosphine)palladium (79.4 mg, 0.068 mmol) was quickly added. The subsequent synthetic reaction steps were the same as those for compound (1-3). Approximately 1.03 g of compound 5-3 was obtained, yield: 84.4%, MALDI-TOF-MS: 1173.42.

[0166] Synthesis of compound 5-4:

[0167] Under nitrogen protection, compound 5-3 (1 g, 0.85 mmol) and triphenylphosphine (893 mg, 3.4 mmol) were added sequentially to a 250 mL three-necked flask containing o-dichlorobenzene. The subsequent synthesis steps were the same as those for compound (1-4). Approximately 630 mg of compound 5-4 was obtained, yield: 66.8%, MALDI-TOF-MS: 1109.25.

[0168] Synthesis of compound 5-5:

[0169] Under nitrogen protection, compound 5-4 (500 mg, 0.45 mmol), potassium carbonate (373.6 mg, 2.7 mmol), and potassium iodide (448.2 mg, 2.7 mmol) were added sequentially to a three-necked flask containing 50 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, bromoisooctane (217.2 mg, 1.12 mmol) was added dropwise. The subsequent synthesis steps were the same as those for compound (1-5). Approximately 448 mg of compound 5-5 was obtained, yield: 74.7%, MALDI-TOF-MS: 1333.61.

[0170] Synthesis of compounds 5-6:

[0171] Under a nitrogen atmosphere, compound 5-5 (400 mg, 0.299 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6). The product of compound 5-6 was obtained in approximately 342 mg, yield: 82.3%, MALDI-TOF-MS: 1389.57.

[0172] Synthesis of compound (25):

[0173] Under a nitrogen atmosphere, compounds 5-6 (200 mg, 0.143 mmol) and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-yl)malononitrile (165.5 mg, 0.719 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthetic steps followed those of compound (1). The final yield was approximately 163 mg of compound (25), yield: 62.8%, MALDI-TOF-MS: 1814.28. The NMR spectrum is shown below. Figure 1 As shown.

[0174] Synthesis Example 6: Synthesis of Compound (33)

[0175]

[0176] Synthesis of compound 6-1:

[0177] Under a nitrogen atmosphere, compounds 5-hexylthiophene-2-amine (3 g, 16.36 mmol), 2-bromo-5-hexylthiophene (4.04 g, 16.36 mmol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (359.1 mg, 0.49 mmol), 1,1'-bis(diphenylphosphine)ferrocene (544.1 mg, 0.98 mmol), and sodium tert-butoxide (4.71 g, 49.08 mmol) were added sequentially to 50 mL of water. In a three-necked flask containing 1,4-dioxane, the temperature was raised to 100°C and reacted for 24 h. After the reactants were completely reacted, the temperature was lowered to room temperature. Then, dichloromethane and water were added to the liquid phase for extraction. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was then separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. The product yielded approximately 2.41 g of compound 6-1, yield: 42.1%, MS: 349.66.

[0178] Synthesis of compound 6-2:

[0179] Under nitrogen protection, 3-bromothiophene[3,2-b]thiophene (1 g, 4.56 mmol), compound 6-1 (1.75 g, 5.01 mmol), and sodium tert-butoxide (1.31 g, 13.68 mmol) were added to 30 mL of o-xylene. After purging with nitrogen for 30 min, tridibenzylacetone dipalladium (125.2 mg, 0.136 mmol) and 2-biscyclohexylphosphine-2′,6′-dimethoxybiphenyl (S-Phos) (112.3 mg, 0.273 mmol) were rapidly added. The subsequent synthetic steps were the same as those for compound (1-1). The product of compound 6-2 was approximately 949 mg, yield: 42.7%, MS: 487.42.

[0180] Synthesis of compound 6-3:

[0181] Under a nitrogen atmosphere, compound 6-2 (900 mg, 1.84 mmol) and anhydrous THF (20 mL) were added to a 50 mL single-necked flask. n-BuLi (0.8 mL, 2.02 mmol, 2.5 M) was added dropwise at -75 °C. After stirring for 1 h, tributyltin chloride (898.3 mg, 2.76 mmol) was added dropwise at -75 °C. The subsequent synthesis steps were the same as those for compound (1-2). The product 6-3 was obtained in approximately 1.22 g, yield 85.3%, MS: 777.04.

[0182] Synthesis of compound 6-4:

[0183] Under nitrogen protection, compound 6-3 (1.11 g, 1.43 mmol) and 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (250 mg, 0.65 mmol) were added to 15 mL of toluene and stirred. After purging with nitrogen for 30 min, tetrakis(triphenylphosphine)palladium (49.59 mg, 0.042 mmol) was quickly added. The subsequent synthetic steps were the same as those for compound (1-3). The product 6-4 was obtained in approximately 643 mg, yield: 82.6%, MALDI-TOF-MS: 1197.51.

[0184] Synthesis of compound 6-5:

[0185] Under nitrogen protection, compound 6-4 (600 mg, 0.5 mmol) and triphenylphosphine (525.5 mg, 2.0 mmol) were added sequentially to a 250 mL three-necked flask containing o-dichlorobenzene. The subsequent synthesis steps were the same as those for compound (1-4). Approximately 385 mg of compound 6-5 was obtained, yield: 67.9%, MALDI-TOF-MS: 1133.49.

[0186] Synthesis of compound 6-6:

[0187] Under nitrogen protection, compound 6-5 (300 mg, 0.264 mmol), potassium carbonate (219.4 mg, 1.58 mmol), and potassium iodide (262.2 mg, 1.58 mmol) were added sequentially to a three-necked flask containing 50 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, bromoisooctane (127.4 mg, 0.66 mmol) was added dropwise. The subsequent synthesis steps were the same as those for compound (1-5). Approximately 236 mg of compound 6-6 was obtained, yield: 65.9%, MALDI-TOF-MS: 1356.78.

[0188] Synthesis of compounds 6-7:

[0189] Under a nitrogen atmosphere, compound 6-6 (200 mg, 0.147 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compound (1-6), yielding about 167 mg of compound 6-7, yield: 80.4%, MALDI-TOF-MS: 1413.14.

[0190] Synthesis of compound (33):

[0191] Under a nitrogen atmosphere, compounds 6-7 (160 mg, 0.113 mmol) and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-yl)malononitrile (157.6 mg, 0.566 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthetic steps were the same as those for compound (1). The final product was approximately 133 mg of compound (33), yield: 64.0%, MALDI-TOF-MS: 1837.65.

[0192] Synthesis Example 7: Synthesis of Compound (41):

[0193]

[0194] Synthesis of compound 7-1:

[0195] Under a nitrogen atmosphere, compound 4-1 (500 mg, 0.374 mmol) and tetrahydrofuran (20 mL) were added to a 100 mL three-necked flask, followed by lithium aluminum hydride (284.4 mg, 7.49 mmol) and reacted overnight at 80 °C. After the reaction was complete, the reaction mixture was poured into an ice-cold dilute hydrochloric acid solution and extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation before proceeding directly to the next step. The product obtained above was dissolved in chloroform (20 mL), and then 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (76.4 mg, 0.336 mmol) and 4,5-difluorophenyl-1,2-diamine (181.1 mg, 1.12 mmol) were added sequentially. The reaction was stirred at room temperature for 24 h. After removing the solvent by vacuum distillation, the product was separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. Approximately 347 mg of compound 7-1 was obtained, yield: 65.6%, MALDI-TOF-MS: 1413.91.

[0196] Synthesis of compound 7-2:

[0197] Under a nitrogen atmosphere, compound 7-1 (300 mg, 0.212 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. The subsequent synthesis reaction steps were the same as those for compounds (1-6). About 253 mg of compound 7-2 was obtained, yield: 81.2%, MALDI-TOF-MS: 1470.14.

[0198] Synthesis of compound (41):

[0199] Under a nitrogen atmosphere, compound 7-2 (200 mg, 0.136 mmol) and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-1-yl)malononitrile (156.5 mg, 0.68 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthesis steps were the same as those for compound (1). The final product was approximately 165 mg of compound (41), yield: 64.1%, MALDI-TOF-MS: 1894.22.

[0200] Synthesis Example 8: Synthesis of Compound (46)

[0201]

[0202] Synthesis of compound 8-1:

[0203] Under nitrogen protection, compounds 1-4 (500 mg, 0.62 mmol), potassium carbonate (514.8 mg, 3.72 mmol), and potassium iodide (617.5 mg, 3.72 mmol) were sequentially added to a three-necked flask containing 50 mL of dimethyl sulfoxide. After purging with nitrogen for 30 min, 5-(bromomethyl)undecane (386.3 mg, 1.55 mmol) was added dropwise. The subsequent synthetic reaction steps were the same as those for compounds (1-5), yielding approximately 489 mg of compound 8-1, yield: 69.1%, MALDI-TOF-MS: 1141.39.

[0204] Synthesis of compound 8-2:

[0205] Under a nitrogen atmosphere, compound 8-1 (480 mg, 0.42 mmol) and tetrahydrofuran (20 mL) were added to a 100 mL three-necked flask, followed by lithium aluminum hydride (319 mg, 8.4 mmol) and reacted overnight at 80 °C. After the reaction was complete, the reaction mixture was poured into an ice-cold dilute hydrochloric acid solution and extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation before proceeding directly to the next step. The product obtained above was dissolved in chloroform (20 mL), and then 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (85.8 mg, 0.378 mmol) and phenyl-1,2-diamine (136.2 mg, 1.26 mmol) were added sequentially. The reaction was stirred at room temperature for 24 h. After removing the solvent by vacuum distillation, the product was separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. Approximately 319 mg of compound 8-2 was obtained, yield: 63.9%, MALDI-TOF-MS: 1187.74.

[0206] Synthesis of compound 8-3:

[0207] Under a nitrogen atmosphere, compound 8-2 (300 mg, 0.252 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6). About 261 mg of compound 8-3 was obtained, yield: 83.3%, MALDI-TOF-MS: 1243.55.

[0208] Synthesis of compound (46):

[0209] Under a nitrogen atmosphere, compound 8-3 (200 mg, 0.16 mmol) and 2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-1-yl)malononitrile (185.02 mg, 0.80 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthesis steps were the same as those for compound (1). The final product was approximately 174 mg of compound (46), yield: 65.2%, MALDI-TOF-MS: 1668.20.

[0210] Synthesis Example 9: Synthesis of Compound (51)

[0211]

[0212] Synthesis of compound 9-1:

[0213] Under a nitrogen atmosphere, compound 4-1 (500 mg, 0.374 mmol) and tetrahydrofuran (20 mL) were added to a 100 mL three-necked flask, followed by lithium aluminum hydride (284.4 mg, 7.49 mmol) and reacted overnight at 80 °C. After the reaction was complete, the reaction mixture was poured into an ice-cold dilute hydrochloric acid solution and extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation before proceeding directly to the next step. The product obtained above was dissolved in chloroform (20 mL), and then 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (76.4 mg, 0.336 mmol) and 1,2,5-thiadiazole-3,4-diamine (130.3 mg, 1.12 mmol) were added sequentially. The reaction was stirred at room temperature for 24 h. After removing the solvent by vacuum distillation, the product was separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent, yielding approximately 336 mg of compound 9-1, yield: 64.8%, MALDI-TOF-MS: 1386.27.

[0214] Synthesis of compound 9-2:

[0215] Under a nitrogen atmosphere, compound 9-1 (300 mg, 0.216 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6). About 245 mg of compound 9-2 was obtained, yield: 78.7%, MALDI-TOF-MS: 1442.03.

[0216] Synthesis of compound (51):

[0217] Under a nitrogen atmosphere, compound 9-2 (200 mg, 0.138 mmol) and 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1-yl)malononitrile (182.4 mg, 0.693 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthetic reaction steps were the same as those for compound (1). Finally, approximately 163 mg of compound (51) was obtained, with a yield of 61.1% and a MALDI-TOF-MS value of 1931.89.

[0218] Synthesis Example 10: Synthesis of compound (56):

[0219]

[0220] Synthesis of compound 10-1:

[0221] Under a nitrogen atmosphere, compound 4-1 (500 mg, 0.374 mmol) and tetrahydrofuran (20 mL) were added to a 100 mL three-necked flask, followed by lithium aluminum hydride (284.4 mg, 7.49 mmol) and reacted overnight at 80 °C. After the reaction was complete, the reaction mixture was poured into an ice-cold dilute hydrochloric acid solution and extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation before proceeding directly to the next step. The product obtained above was dissolved in methanol (12 mL) and ethanol (12 mL), and then phenanthrene-9,10-dione (116.8 mg, 0.561 mmol) was added. The reaction was stirred at 65 °C for 24 h, and the reaction was quenched with water. Then, dichloromethane was added for extraction. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was then separated by silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether as the eluent. The product yielded approximately 332 mg of compound 10-1, with a yield of 60.1% and a MALDI-TOF-MS value of 1478.33.

[0222] Synthesis of compound 10-2:

[0223] Under a nitrogen atmosphere, compound 10-1 (300 mg, 0.202 mmol) was added to a 100 mL three-necked flask, and about 5 mL of anhydrous DMF was added. After purging with nitrogen three times, the subsequent synthesis reaction steps were the same as those for compounds (1-6). About 257 mg of compound 10-2 was obtained, yield: 82.8%, MALDI-TOF-MS: 1534.17.

[0224] Synthesis of compound (56):

[0225] Under a nitrogen atmosphere, compound 10-2 (200 mg, 0.130 mmol) and 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-1-yl)malononitrile (150 mg, 0.651 mmol) were added to 20 mL of dry chloroform, followed by the addition of 0.8 mL of pyridine. The subsequent synthesis steps were the same as those for compound (1). Finally, approximately 156 mg of compound (56) was obtained, with a yield of 61.4% and a MALDI-TOF-MS value of 1958.44.

[0226] Organic photovoltaic (OPV) device fabrication examples

[0227] Device Example 1

[0228] Device structure such as Figure 1 As shown, the organic photovoltaic device includes a substrate, an anode, an anode buffer layer, a photoactive layer, a cathode buffer layer, and a cathode layer stacked sequentially; wherein, the materials of the anode, anode buffer layer, photoactive layer, cathode buffer layer, and cathode layer are, in sequence: indium tin oxide (ITO) / Cbz-2Ph / photoactive layer material / PDINN / Ag.

[0229] Its preparation method includes the following steps:

[0230] 1) ITO substrate cleaning

[0231] Clean the ITO conductive glass with detergent, rinse it thoroughly, and then ultrasonically clean it for 15 minutes with deionized water, acetone, and isopropanol. After that, dry it with nitrogen and treat it in a plasma cleaner for 5 minutes to further clean the surface and improve wettability.

[0232] 2) Preparation of the anode buffer layer

[0233] The small molecule self-assembled hole transport material Cbz-2Ph (dissolved in isopropanol at a concentration of 0.5 mg / mL) was uniformly spin-coated onto ITO in air at a speed of 3000 rpm for 30 s. After spin coating, the material was dried at 100 °C for 5 min to obtain the anodic buffer layer.

[0234]

[0235] 3) Preparation of photoactive layer

[0236] In a glove box (inert gas atmosphere), the photoactive layer material solution is uniformly spin-coated onto the anode buffer layer at a speed of 1800-3000 rpm to obtain a photoactive layer with a total thickness of approximately 100 nm.

[0237] The photoactive layer material solution is prepared as follows: the donor material and acceptor material are dissolved in chloroform, and liquid additive 1-chloronaphthalene is added to obtain the photoactive layer material solution. The donor material in the photoactive layer material solution is selected from polymer PM6, the host acceptor material is selected from L8-BO, and the guest acceptor material is selected from compound (1). PM6:L8-BO:compound (1) is added to the chloroform solution at a mass ratio of 1:1:0.2, with a total concentration of 16 mg / mL, and the amount of 1-chloronaphthalene additive is 0.5% (v:v, volume ratio).

[0238]

[0239] 4) Preparation of cathode buffer layer

[0240] The device with the photoactive layer was heat-annealed on a hot stage at 95°C for 10 min. Then, the cathode buffer layer material PDINN (prepared by dissolving PDINN in methanol to a concentration of 1.0 mg / mL) was uniformly spin-coated onto the photoactive layer at a spin speed of 3000 rpm for 30 s to obtain the cathode buffer layer.

[0241] 5) Cathode layer preparation

[0242] 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 approximately 100 nm.

[0243] 6) Packaging

[0244] The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0245] Device Examples 2-10

[0246] The preparation methods of device examples 2-10 are the same as those of device example 1. The difference lies in the selection of guest acceptor materials in the photoactive layer. Specifically, the guest acceptor material compound (1) is replaced with compound (5), compound (16), compound (21), compound (25), compound (33), compound (41), compound (46), compound (51) and compound (56), respectively. See Table 1 for details.

[0247] Device Comparison Example 1

[0248] The fabrication method of the device in Comparative Example 1 is the same as that in Device Example 1, except that the preparation method of the photoactive layer material solution in the photoactive layer is different, specifically:

[0249] The donor and acceptor materials were dissolved in chloroform, and liquid additive 1-chloronaphthalene was added to obtain a photoactive layer material solution. The donor material in the photoactive layer material solution was selected from polymer PM6, and the acceptor material was selected from L8-BO. ​​PM6:L8-BO was added to the chloroform solution at a mass ratio of 1:1.2, with a total concentration of 16 mg / mL, and the amount of 1-chloronaphthalene additive was 0.5% (v:v, volume ratio).

[0250] The prepared organic photovoltaic cells were subjected to performance testing. Under the illumination of the AM1.5 standard light simulator, the test device data are shown in Table 1.

[0251] Table 1

[0252]

[0253]

[0254] As shown in Table 1, the small molecules with β-position aromatic amine side chains described in this invention, when used as guest acceptor materials in combination with suitable donor materials in organic photovoltaic devices, exhibit good photoelectric conversion efficiency. In particular, devices in Example 3 and Example 4 show photoelectric conversion efficiencies exceeding 20%, which are far higher than those in Comparative Example 1. This indicates that aromatic amine side chains have significant advantages in regulating the chemical energy levels of acceptor molecules, optical absorption, and inhibiting the aggregation of molecules in the active mixed layer.

[0255] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An amine organic compound, characterized in that: The amine organic compounds are selected from the structures shown in formula (I): (I) in: Each time R1 appears, it is independently selected from alkyl groups having 1-30 carbon atoms; R2 and R3, each time appearing independently, are selected from straight-chain alkyl groups having 1-20 carbon atoms, branched alkyl groups having 3-20 carbon atoms, cyclic alkyl groups having 3-20 carbon atoms, and groups influenced by one or more R groups. b Substituted or unsubstituted heteroaromatic groups having 5-10 ring atoms, or containing one or more R... b Aromatic groups having 6-10 carbon atoms, substituted or unsubstituted; the R b Each occurrence is independently selected from straight-chain alkyl groups having 1-20 carbon atoms, branched alkyl groups having 3-20 carbon atoms, or cyclic alkyl groups having 3-20 carbon atoms; Each time Y1 and Y2 appear, they are independently selected from O, S, or Se; Each time M appears, it is independently selected from O or C(CN)2; Each occurrence of Ar1 is independently selected from substituted or unsubstituted heteroaromatic groups having 5-20 ring atoms; Ar2 and Ar3 are each independently selected from substituted or unsubstituted aromatic groups having 6-20 carbon atoms; The term "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, -CN, -CF3, alkyl having 1-20 carbon atoms, alkoxy having 1-20 carbon atoms, or alkylthio having 1-20 carbon atoms.

2. The amine organic compound according to claim 1, characterized in that: Each occurrence of R2 and R3 is independently selected from any of the following groups: 。 3. The amine organic compound according to claim 1, characterized in that: The Ar1 is selected from any of the following groups: Wherein: Z is selected independently from O, S or Se each time it appears; Each time X appears, it is independently selected from N or CR4; Each time R4 appears, it is independently selected from -H, -D, -F, -Cl, -Br, -I, -CN, -CF3, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, cyclic alkyl with 3-10 carbon atoms, straight-chain alkoxy with 1-10 carbon atoms, branched alkoxy with 3-10 carbon atoms, straight-chain alkylthio with 1-10 carbon atoms, and branched alkylthio with 3-10 carbon atoms; # indicates a fusion site, which is selected from C atoms.

4. The amine organic compound according to claim 3, characterized in that: The Ar1 is selected from any of the following groups: 。 5. The amine organic compound according to claim 1, characterized in that: Y1 is selected from S, and Y2 is selected from either S or Se.

6. The amine organic compound according to claim 1, characterized in that: Each occurrence of Ar2 and Ar3 is independently selected from any of the following groups: The R d Each occurrence is independently selected from -D, -F, -Cl, -Br, -I, -CN, -CF3, alkyl groups having 1-6 carbon atoms, or alkoxy groups having 1-6 carbon atoms; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2, 3, 4, 5 or 6.

7. The amine organic compound according to claim 1, characterized in that: The amine organic compounds mentioned herein are selected from any of the following structures: 。 8. A mixture, characterized in that: The mixture comprises an amine organic compound as described in any one of claims 1-7 and at least one other organic functional material, wherein the other organic functional material is selected from photoactive layer donor materials or photoactive layer acceptor materials.

9. An organic photovoltaic cell, the organic photovoltaic cell comprising a cathode, an anode, and a photoactive layer located between the cathode and the anode, characterized in that: The photoactive layer comprises an amine organic compound as described in any one of claims 1-7 or a mixture as described in claim 8.

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