A cycloalkyl-containing small organic molecule compound and application thereof

Abstract

The present application relates to a kind of cycloalkyl-containing organic small molecule compounds, which can be applied as donor material in organic solar cell device.The cycloalkyl-containing organic small molecule compounds provided by the present application can greatly reduce the energy loss caused by molecular rotation, vibration, conformation change and the like by introducing cycloalkyl group in terminal electron-withdrawing unit compared with straight-chain or branched alkyl and other substituents, so that the organic compound has good stability and heat resistance;At the same time, the cycloalkyl group can promote the molecule to adopt planar arrangement, improve the carrier transport performance, effectively realize the charge separation of exciton, so as to improve the photoelectric conversion performance of organic solar cell.

Description

Technical Field

[0001] This invention relates to the field of organic solar cell materials, and in particular to a small organic molecule compound containing cycloalkyl groups and its applications. Background Technology

[0002] Organic solar cells have long attracted the attention of researchers due to their simple fabrication, low cost, wide range of material options, and ability to be made into flexible devices, and are considered a new generation of green energy technology with significant industrial prospects. Compared with traditional inorganic silicon solar cells, organic solar cells are thinner, more flexible, semi-transparent, and can generate electricity indoors or in low light conditions, expanding application markets that traditional photovoltaics cannot reach. They have broad application prospects in wearable electronic devices, smart IoT, smart homes, smart agriculture, building-integrated photovoltaics, new energy vehicles, and new power systems based on new energy sources.

[0003] High-efficiency organic solar cells primarily use polymers as donor materials. The molecular weight of polymers is roughly determined by their molecular weight distribution, which makes batch-to-batch variations in polymer organic solar cell production common. In contrast, small organic molecules have defined chemical structures and molecular weights, are easier to separate and purify, and offer greater controllability during large-scale production. Furthermore, small molecules avoid certain characteristics of polymers, such as defects in chain segments and ends, which can lead to structural disorder and low-position trap states. Although small organic molecule materials have simpler structures and are easier to prepare, modify, and optimize compared to polymer donor materials, the difficulty in controlling the photoactive layer morphology of the all-small molecule system (small molecule donor and acceptor) still results in the photoelectric conversion efficiency of all-small molecule organic solar cells lagging behind that of polymer solar cells. Therefore, developing novel small molecule donor materials is crucial for achieving high-efficiency all-small molecule organic solar cells. Summary of the Invention

[0004] In view of the above-mentioned problems in the prior art, the purpose of this application is to provide an organic small molecule compound that can be used as a donor material in organic solar cell devices, thereby improving the photoelectric conversion efficiency of small molecule solar cells.

[0005] To achieve the objective of this invention, the technical solution is as follows:

[0006] A small organic molecule compound containing a cycloalkyl group, having the structure shown in chemical formula (I),

[0007]

[0008] in,

[0009] Each time Z appears, it is selected from O or S, either the same or different.

[0010] Each occurrence of Ar1 and Ar2 is independently selected from those that are not substituted or are replaced by R. * Replacing aromatic groups having 6-20 carbon atoms, or unsubstituted or replaced by R * Substitute heteroaromatic groups having 5-20 ring atoms;

[0011] n is selected from 1, 2, 3, or 4;

[0012] m is selected from 1, 2, 3, or 4;

[0013] R1 and R2 are independently selected from those having hydrogen, deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 20 carbon atoms, straight-chain alkoxy with 1 to 20 carbon atoms, straight-chain alkylthio with 1 to 20 carbon atoms, branched alkyl with 3 to 20 carbon atoms, branched alkoxy with 3 to 20 carbon atoms, branched alkylthio with 3 to 20 carbon atoms, unsubstituted or R * Replacing aromatic groups having 6-20 carbon atoms, or unsubstituted or replaced by R * A group that replaces a heteroaromatic group having 5-20 ring atoms, or a group formed by a combination of the above groups;

[0014] Each time R3 appears, it is selected from cycloalkyl groups having 3-20 carbon atoms, either the same or different.

[0015] R * Each occurrence is selected from deuterium, halogen, cyano, nitro, straight-chain alkyl having 1 to 20 carbon atoms, straight-chain alkoxy having 1 to 20 carbon atoms, straight-chain alkylthio having 1 to 20 carbon atoms, branched alkyl having 3 to 20 carbon atoms, branched alkoxy having 3 to 20 carbon atoms, branched alkylthio having 3 to 20 carbon atoms, aromatic groups having 6 to 20 carbon atoms, heteroaromatic groups having 5 to 20 cyclic atoms, or groups formed by combinations of the above groups.

[0016] The present invention also provides a mixture comprising the cycloalkyl-containing small molecule organic compound as described above, and at least one other organic functional material; wherein the at least one other organic functional material is selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material.

[0017] An organic electronic device comprising at least one functional layer, said functional layer comprising a cycloalkyl-containing small molecule organic compound or mixture as described above.

[0018] Compared with the prior art, the present invention has at least the following beneficial technical effects:

[0019] In the design of small molecule donor materials, modifications to the terminal electron-withdrawing units play a crucial role in regulating their solubility, energy levels, molecular packing patterns, and thermal stability. This invention introduces cycloalkyl groups into the terminal electron-withdrawing units. Compared to straight-chain or branched alkyl substituents, cycloalkyl groups can significantly reduce energy losses caused by molecular rotation, vibration, and conformational changes, resulting in organic compounds with good stability and heat resistance. At the same time, cycloalkyl groups can promote a planar arrangement of molecules, improve carrier transport performance, and effectively achieve exciton charge separation, thereby enhancing the photoelectric conversion performance of organic solar cells.

[0020] In particular, when the terminal electron-withdrawing unit is selected from adamantyl groups, the molecular conjugation is extended, electron localization is avoided, and electron separation and transport are facilitated. This changes the hole mobility, spatial structure and energy level of the compound, making it more compatible with small molecule acceptor materials and more effectively improving device performance. Attached Figure Description

[0021] Figure 1 These are schematic diagrams of the organic solar cells in Device Embodiments 1-6 and Device Comparative Embodiments 1-2 of the present invention. Detailed Implementation

[0022] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.

[0023] 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").

[0024] In this invention, the active layer and the photoactive layer have the same meaning and can be used interchangeably.

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

[0026] In this invention, when the same substituent appears multiple times, it can be independently selected from the same or different groups. For example, if the general formula contains multiple R3s, then the R3s can be independently selected from the same or different groups.

[0027] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl groups. Straight-chain alkyl groups can have 1 to 20, 1 to 16, 1 to 10, or 1 to 6 carbon atoms. Branched alkyl groups can have 3 to 20, 3 to 16, 3 to 10, or 3 to 6 carbon atoms. Non-limiting examples of straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and -C. 10 H 21 -C 11 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 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. Non-limiting examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloalkyl groups containing 7 carbon atoms, cycloalkyl groups containing 8 carbon atoms, cycloalkyl groups containing 9 carbon atoms, cycloalkyl groups containing 10 carbon atoms, cycloalkyl groups containing 11 carbon atoms, cycloalkyl groups containing 12 carbon atoms, cycloalkyl groups containing 13 carbon atoms, cycloalkyl groups containing 14 carbon atoms, cycloalkyl groups containing 15 carbon atoms, and cycloalkyl groups containing 16 carbon atoms.

[0028] The term "straight-chain alkoxy" refers to a group with the structure "-O-straight-chain alkyl", which is defined as above.

[0029] The term "branched alkoxy" refers to a group with the structure "-O-branched alkyl", and the branched alkyl is defined as described above.

[0030] The term "straight-chain alkylthio" refers to a group with the structure "-S-straight-chain alkyl", which is defined as above.

[0031] The term "branched alkylthio" refers to a group with the structure "-S-branched alkyl", and the branched alkyl is defined as described above.

[0032] In this invention, "halogen" includes fluorine, chlorine, bromine, iodine, etc.

[0033] In this invention, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the number of ring atoms in a benzene ring is 6, in a naphthalene ring it is 10, in a thiophene group it is 5, and in a thiophene-3-thiophene group it is 8.

[0034] In this invention, "aromatic group" refers to any optional functional group or substituent derived from an aromatic carbon ring. The aromatic group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aromatic group can be a monocyclic aromatic group, a fused-ring aromatic group, two or more monocyclic aromatic groups conjugated by carbon-carbon bonds, a monocyclic aromatic group and a fused-ring aromatic group conjugated by carbon-carbon bonds, or two or more fused-ring aromatic groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aromatic groups in this application. Aromatic groups include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives.

[0035] In this invention, a "heteroaromatic group" refers to a monovalent aromatic ring or its derivative containing one, two, three, four, five, six or more heteroatoms. The heteroatoms can be at least one of B, O, N, P, Si, Se, and S. The heteroaromatic group can be a monocyclic heteroaryl or a polycyclic heteroaryl; in other words, it can be a single aromatic ring system or a system of multiple aromatic rings conjugated by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. Heteroaromatic groups include, but are not limited to: thiophene, furanyl, pyrrolyl, diazolyl, triazolyl, imidazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiophene, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrol, thienopyrrol, thienopyrrol, furanol, furanol, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridine, primidyl, quinazolinone, dibenzothiophene, dibenzofuranyl, carbazole and their derivatives.

[0036] In this invention, the "*" connected to a single bond indicates a connection or fusion site.

[0037] 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.

[0038] 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.

[0039] The terms “combinations thereof,” “any combination thereof,” “any combination thereof,” and “combination” used in this invention include all suitable combinations of any two, any three, or any three or more items of the listed groups.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] The first aspect of this invention provides a small organic molecule compound containing a cycloalkyl group, having the structure shown in chemical formula (I):

[0044]

[0045] in,

[0046] Each time Z appears, it is selected from O or S, either the same or different.

[0047] Each occurrence of Ar1 and Ar2 is independently selected from those that are not substituted or are replaced by R. * Replacing aromatic groups having 6-20 carbon atoms, or unsubstituted or replaced by R * Substitute heteroaromatic groups having 5-20 ring atoms;

[0048] n is selected from 1, 2, 3, or 4;

[0049] m is selected from 1, 2, 3, or 4;

[0050] R1 and R2 are independently selected from those having hydrogen, deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 20 carbon atoms, straight-chain alkoxy with 1 to 20 carbon atoms, straight-chain alkylthio with 1 to 20 carbon atoms, branched alkyl with 3 to 20 carbon atoms, branched alkoxy with 3 to 20 carbon atoms, branched alkylthio with 3 to 20 carbon atoms, unsubstituted or R * Replacing aromatic groups having 6-20 carbon atoms, or unsubstituted or replaced by R * A group that replaces a heteroaromatic group having 5-20 ring atoms, or a group formed by a combination of the above groups;

[0051] Each time R3 appears, it is selected from cycloalkyl groups having 3-20 carbon atoms, either the same or different.

[0052] R * Each occurrence is independently selected from deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 20 carbon atoms, straight-chain alkoxy with 1 to 20 carbon atoms, straight-chain alkylthio with 1 to 20 carbon atoms, branched alkyl with 3 to 20 carbon atoms, branched alkoxy with 3 to 20 carbon atoms, branched alkylthio with 3 to 20 carbon atoms, aromatic groups with 6 to 20 carbon atoms, heteroaromatic groups with 5 to 20 cyclic atoms, or groups formed by combinations of the above groups.

[0053] Furthermore, R *Each occurrence is independently selected from deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 16 carbon atoms, straight-chain alkoxy with 1 to 16 carbon atoms, straight-chain alkylthio with 1 to 16 carbon atoms, branched alkyl with 3 to 16 carbon atoms, branched alkoxy with 3 to 16 carbon atoms, branched alkylthio with 3 to 16 carbon atoms, aromatic groups with 6 to 12 carbon atoms, or heteroaromatic groups with 5 to 12 cyclic atoms, or groups formed by combinations of the above groups.

[0054] In this invention, "each time it appears, it is independently selected" and "each time it appears, it is selected in the same or different ways" can be interchanged and should be interpreted broadly. It can mean that the specific options between different groups do not affect each other, or that the specific options between the same groups do not affect each other.

[0055] In this invention, "unreplaced or R" * "Substitution" means that the functional group specified after the term may not be substituted, or may be substituted by one or more R groups. * replace.

[0056] The term "one or more" means one, two, three, four, or more.

[0057] In one embodiment, R3 is selected from cycloalkyl groups having 3-15 carbon atoms each time it appears; further, R3 is selected from cycloalkyl groups having 3-10 carbon atoms each time it appears.

[0058] Furthermore, each time R3 appears, it is selected from any of the following groups, either identically or differently:

[0059]

[0060] * indicates a connection point.

[0061] In one specific embodiment, Each occurrence is selected from any of the following groups, either identically or differently:

[0062]

[0063] Furthermore, in general formula I, The same functional group is selected each time it appears.

[0064] In one embodiment, Z is selected from O.

[0065] In some other preferred embodiments, Z is selected from S. When Z is selected from S, the chemical formula of the cycloalkyl-containing organic small molecule material contains a benzodithiophene unit, thus it has a large conjugated system and good symmetry planarity, as well as excellent charge transport performance. When used as a donor unit in organic compounds, it can improve the charge transport performance of the material.

[0066] In a preferred embodiment, R1 and R2 are independently selected from straight-chain alkyl groups having 1 to 16 carbon atoms, straight-chain alkoxy groups having 1 to 16 carbon atoms, straight-chain alkylthio groups having 1 to 16 carbon atoms, branched alkyl groups having 3 to 16 carbon atoms, branched alkoxy groups having 3 to 16 carbon atoms, branched alkylthio groups having 3 to 16 carbon atoms, unsubstituted or R * Replacing aromatic groups having 6-10 carbon atoms, or unsubstituted or replaced by R * The group replaces heteroaromatic groups with 5-10 ring atoms, or groups formed by combinations of the above groups. The reason is that the preferred R1 and R2 groups can endow the compound with "two-dimensional" characteristics of the frontier orbitals, resulting in more inter-chain π overlap, thereby improving exciton diffusion or charge transport in the material.

[0067] In a more preferred embodiment, R1 and R2 are independently selected from straight-chain alkyl groups having 1 to 16 carbon atoms, straight-chain alkoxy groups having 1 to 16 carbon atoms, straight-chain alkylthio groups having 1 to 16 carbon atoms, branched alkyl groups having 3 to 16 carbon atoms, branched alkoxy groups having 3 to 16 carbon atoms, branched alkylthio groups having 3 to 16 carbon atoms, or any of the following groups:

[0068]

[0069] In each occurrence of R4, R5, R6, and R7, the same or different groups are selected from hydrogen, deuterium, halogen, cyano, nitro, straight-chain alkyl having 1 to 16 carbon atoms, straight-chain alkoxy having 1 to 16 carbon atoms, straight-chain alkylthio having 1 to 16 carbon atoms, branched alkyl having 3 to 16 carbon atoms, branched alkoxy having 3 to 16 carbon atoms, branched alkylthio having 3 to 16 carbon atoms, or groups formed by combinations of the above groups.

[0070] Furthermore, R4, R5, R6, and R7, each time appearing, are selected from hydrogen, deuterium, fluorine, chloro, bromine, cyano, -CF3, branched alkyl groups having 3 to 16 carbon atoms, branched alkoxy groups having 3 to 16 carbon atoms, or branched alkylthio groups having 3 to 16 carbon atoms.

[0071] The "branched alkyl group with 3 to 16 carbon atoms" includes

[0072] In one embodiment, the cycloalkyl-containing small organic molecule compound has a structure as shown in general formula (II-1) or (II-2):

[0073]

[0074] In one specific embodiment, R1 and R2 are independently selected from any of the following structures:

[0075]

[0076]

[0077] Furthermore, in general formula (I), R1 and R2 are selected from the same groups.

[0078] In one embodiment, Ar1 and Ar2 are each independently selected from unsubstituted or R-substituted Ar1. * Replacing aromatic groups having 6-12 carbon atoms, or unsubstituted or replaced by R * It replaces heteroaromatic groups having 5-12 ring atoms.

[0079] Preferably, each occurrence of Ar1 and Ar2 is independently selected from any of the following groups:

[0080]

[0081] in,

[0082] Each time X appears, it is independently selected from N or CR8;

[0083] Each time Y appears, it is independently selected from O, S, or Se;

[0084] Each time W appears, it is independently selected from O, S, and CR9R. 10 NR 11 ;

[0085] R8, R9, R 10 R 11 Each occurrence is independently selected from hydrogen, deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 20 carbon atoms, straight-chain alkoxy with 1 to 20 carbon atoms, straight-chain alkylthio with 1 to 20 carbon atoms, branched alkyl with 3 to 20 carbon atoms, branched alkoxy with 3 to 20 carbon atoms, branched alkylthio with 3 to 20 carbon atoms, aromatic groups with 6 to 20 carbon atoms, or heteroaromatic groups with 5 to 20 cyclic atoms, or groups formed by combinations of the above groups;

[0086] * indicates a connection point.

[0087] Furthermore, R8, R9, R 10 R 11Each occurrence is independently selected from hydrogen, deuterium, halogen, cyano, nitro, straight-chain alkyl having 1 to 16 carbon atoms, straight-chain alkoxy having 1 to 16 carbon atoms, straight-chain alkylthio having 1 to 16 carbon atoms, branched alkyl having 3 to 16 carbon atoms, branched alkoxy having 3 to 16 carbon atoms, branched alkylthio having 3 to 16 carbon atoms, or a group formed by a combination of the above groups.

[0088] In one embodiment, Independently selected from any of the following groups:

[0089]

[0090] In a preferred embodiment, Independently selected from any of the following groups:

[0091]

[0092]

[0093] in,

[0094] R8, R 11 Each time it appears, it is independently selected from deuterium, halogen, cyano, nitro, straight-chain alkyl having 1 to 10 carbon atoms, straight-chain alkoxy having 1 to 16 carbon atoms, straight-chain alkylthio having 1 to 10 carbon atoms, branched-chain alkyl having 3 to 16 carbon atoms, branched-chain alkoxy having 3 to 10 carbon atoms, and branched-chain alkylthio having 3 to 10 carbon atoms.

[0095] Furthermore, each time R8 appears, it is independently selected from deuterium, fluorine, straight-chain alkyl with 1 to 10 carbon atoms, straight-chain alkoxy with 1 to 10 carbon atoms, branched alkyl with 3 to 10 carbon atoms, and branched alkoxy with 3 to 10 carbon atoms.

[0096] Furthermore, R 11 Each occurrence is independently selected from branched alkyl groups having 3 to 16 carbon atoms.

[0097] In one specific embodiment, the Independently selected from the following groups:

[0098]

[0099]

[0100] Furthermore, in general formula I The selected functional groups are the same.

[0101] In one specific embodiment, the cycloalkyl-containing small organic molecule compound is selected from any of the following structural formulas, but is not limited thereto:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] A second aspect of the present invention provides a photoactive layer material, wherein the photoactive layer material is selected from the cycloalkyl-containing small molecule organic compounds described in the first aspect.

[0108] Preferably, the present invention provides a photoactive layer donor material, wherein the photoactive layer donor material is selected from the cycloalkyl-containing small molecule organic compounds provided by the present invention.

[0109] A third aspect of the present invention provides a mixture comprising a cycloalkyl-containing small organic molecule compound as provided in the present invention, and at least one other organic functional material; the at least one other organic functional material may be selected as an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material. The weight ratio of the cycloalkyl-containing small organic molecule compound to the other organic functional material is from 1:99 to 99:1.

[0110] In one embodiment, the mixture comprises a photoactive layer donor material and a photoactive layer acceptor material in a weight ratio of donor material to acceptor material of 1:1 to 1:1.2.

[0111] In one embodiment, the at least another organic functional material comprises at least one photoactive layer acceptor material; preferably, the photoactive layer acceptor material is selected from one, two, or more of the following structures:

[0112]

[0113]

[0114] A fourth aspect of the present invention provides a composition comprising a cycloalkyl-containing small organic molecule compound as described in the first aspect, or a mixture as described in the third aspect, and at least one organic solvent. The organic solvent is selected from aliphatic hydrocarbons, chlorinated hydrocarbons, aromatic hydrocarbons, ketones, ethers, and mixtures thereof.

[0115] In one embodiment, the organic solvent is selected from dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, 2,4-dimethylanisole, 1-methylnaphthalene, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, N,N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, 1,5-dimethyltetrahydrofuran, acetophenone, acetophenone, tetrahydronaphthalene, 2-methylthiophene, 3-methylthiophene, decahydronaphthalene, indane, methyl benzoate, ethyl benzoate, mesitylene, or a mixture of the above organic solvents.

[0116] In a preferred embodiment, the organic solvent is selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.

[0117] It is understood that the organic solvent can evaporate from the solvent system to form a thin film comprising the organic compound.

[0118] In one embodiment, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives.

[0119] The compositions of this invention can be used as coatings or printing inks in the fabrication of organic solar cells. In one embodiment, the compositions are used to fabricate organic electronic devices by a printing or coating method. The printing or coating method can be, but is 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, brushing, pad printing, slot-fed coating, etc. Slot coating, spin coating, and inkjet printing are preferred.

[0120] The fifth aspect of the present invention provides the use of the cycloalkyl-containing small organic molecule compounds as described in the first aspect, the mixtures as described in the third aspect, or the compositions as described in the fourth aspect in organic electronic devices.

[0121] An organic electronic device includes at least one functional layer comprising an organic compound or mixture as described above. Preferably, the organic electronic device is selected from organic solar cells (OPVs).

[0122] An organic solar cell includes a first electrode, a second electrode, and one or more functional layers disposed between the first electrode and the second electrode, wherein the functional layers include at least a photoactive layer, and the photoactive layer material is selected from the organic compounds or mixtures described above, or prepared from the above-described compositions.

[0123] The one or more functional layers may be a single-layer structure. When it is a single-layer structure, the functional layer is selected from the photoactive layer.

[0124] The one or more functional layers may also be a multilayer tandem structure with two or more functional layers laminated together. When it is a multilayer tandem structure with two or more functional layers, the functional layers may include at least two of an anode buffer layer, a photoactive layer, and a cathode buffer layer. The functional layers may be fabricated using common methods and materials for preparing organic solar cells.

[0125] In a preferred embodiment, the one or more functional layers are selected from an anode buffer layer, a photoactive layer, and a cathode buffer layer.

[0126] In one embodiment, the first electrode is an anode and the second electrode is a cathode; in another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0127] Furthermore, the organic solar cell also includes a substrate. Specifically, the substrate may be disposed below the first electrode.

[0128] 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), and polyimide (PI), and substrates commonly used in organic solar cells may also be used.

[0129] The anode electrode can be made of transparent or translucent materials, but is not limited to these. The anode electrode may include metals, such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; and conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole and polyaniline, but is not limited to these.

[0130] The cathode electrode can be made of a metal with a low work function. The cathode electrode may include metals such as silver (Ag), aluminum (Al), platinum (Pt), tungsten (W), copper (Cu), molybdenum (Mo), gold (Au), nickel (Ni), and palladium (Pd), or alloys thereof; and materials with multilayer structures such as LiF / Al, LiO2 / Al, LiF / Fe, MoO3 / Al, Al∶Li, Al∶BaF2, and Al∶BaF2∶Ba, but are not limited thereto.

[0131] The photoactive layer comprises an electron donor material and an electron acceptor material. Specifically, the electron donor material is selected from the cycloalkyl-containing small organic molecule compounds mentioned above, and the acceptor material is preferably selected from one, two, or more of compounds (RM-1)-(RM-21).

[0132] The anode buffer layer material can be selected from poly(styrene sulfonic acid) PEDOT:PSS (poly(3,4-ethylenedioxythiophene)), molybdenum oxide (MoOx), vanadium oxide (V2O5), nickel oxide (NiO), tungsten oxide (WO4), etc. x Preferably, x is selected from 2 or 3, etc., but not limited to this.

[0133] The cathode buffer layer material can be an electron-withdrawing metal oxide or polymer. The metal oxide can be a metal complex containing 8-hydroxyquinoline, a complex containing Alq3, a metal complex containing Liq, LiF, Ca, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs2CO3), etc., and the polymer can be PFN-Br or PFN, etc., but is not limited to these.

[0134] The present invention also relates to the application of organic solar cells prepared according to the present invention in various devices, including, but not limited to, building-integrated photovoltaics (BIPV), electronic shelf labels, indoor photovoltaics, the Internet of Things, smart agriculture, etc.

[0135] The present invention will now be described in conjunction with preferred compound preparation and device embodiments. However, the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Guided by the concept of the present invention, those skilled in the art should realize that any changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0136] Example 1: Synthesis of compound (1)

[0137]

[0138] Synthesis of compounds 1-2:

[0139] Accurately weigh rhodanine (2.7 g, 20 mmol) and potassium hydroxide (3.4 g, 60 mmol) into a 100 mL three-necked flask, and add 50 mL of ethanol. After purging with nitrogen three times, the entire system was heated to 80 °C and stirred for 12 h. After the starting materials had completely reacted, the mixture was cooled in an ice bath, filtered, and the filter cake was washed three times with ethanol to obtain the crude product. The crude product and compound 1-1 (1.6 g, 10 mmol) were added to a 100 mL three-necked flask, and 30 mL of DMF was added. The entire system was heated to 130 °C and stirred for 12 h. After the reaction solution cooled, it was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was purified by silica gel column chromatography using PE as the eluent to obtain approximately 2.9 g of compound 1-2, yield: 68%. MS: 215.49.

[0140] Synthesis of compounds 1-5:

[0141] Accurately weigh compounds 1-3 (4.0 g, 5 mmol), 1-4 (5.5 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 8:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 5.9 g of compounds 1-5, with a yield of 83%. MALDI-TOF MS: 1420.68.

[0142] Synthesis of compounds 1-6:

[0143] Accurately weigh compounds 1-5 (5.7 g, 4 mmol) and add them to a 100 mL three-necked flask, then add 25 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh phosphorus oxychloride (1.2 g, 8 mmol) and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) as the eluent to obtain approximately 3.8 g of compounds 1-6, yield: 64%. MALDI-TOF MS: 1476.72.

[0144] Synthesis of compound (1):

[0145] Accurately weigh compounds 1-6 (0.37 g, 0.25 mmol), compounds 1-2 (0.12 g, 0.55 mmol), and 1 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 7 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent to obtain approximately 0.36 g of compound (1), with a yield of 78%. MALDI-TOF MS: 1871.47.

[0146] Example 2: Synthesis of compound (10)

[0147]

[0148] Synthesis of compound 10-2:

[0149] Accurately weigh rhodanine (2.7 g, 20 mmol) and potassium hydroxide (3.4 g, 60 mmol) into a 100 mL three-necked flask, and add 50 mL of ethanol. After purging with nitrogen three times, the entire system was heated to 80 °C and stirred for 12 h. After the reactants had completely reacted, the mixture was cooled in an ice bath, filtered, and the filter cake was washed three times with ethanol to obtain the crude product. The crude product and compound 10⁻¹ (2.2 g, 10 mmol) were added to a 100 mL three-necked flask, and 30 mL of DMF was added. The entire system was heated to 130 °C and stirred for 12 h. After the reaction solution cooled, it was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was purified by silica gel column chromatography using PE as the eluent to obtain approximately 3.8 g of compound 10⁻², yield: 72%. MS: 267.33.

[0150] Synthesis of compound 10-5:

[0151] Accurately weigh compound 10⁻³ (4.9 g, 5 mmol), compound 10⁻⁴ (4.1 g, 10 mmol), and Pd(PPh₃)₄ (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge the mixture with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 9:1 (v / v) as eluent, separate the product by silica gel column chromatography to obtain approximately 5.3 g of compound 10⁻⁵, with a yield of 80%. MALDI-TOF MS: 1316.32.

[0152] Synthesis of compound 10⁻⁶:

[0153] Accurately weigh 4.6 g (3.5 mmol) of compound 10⁻⁵ and 1.3 g (7 mmol) of NBS into a 100 mL three-necked flask, add 50 mL of chloroform and 5 mL of acetic acid. After purging with argon three times, lower the temperature to 0 °C in an ice-salt bath, maintain the reaction temperature at 0 °C for 6 h, allow to rise naturally to room temperature, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM eluent of 8:1 (v / v) to obtain approximately 4.6 g of compound 10⁻⁶, yield: 89%. MALDI-TOF MS: 1473.60.

[0154] Synthesis of compound 10-8:

[0155] Accurately weigh compound 10⁻⁶ (4.4 g, 3 mmol), compound 10⁻⁷ (2.2 g, 6 mmol), and Pd(PPh₃)₄ (0.07 g, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge the mixture with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 8:1 (v / v) as eluent, separate the product by silica gel column chromatography to obtain approximately 3.8 g of compound 10⁻⁸, with a yield of 86%. MALDI-TOF MS: 1480.48.

[0156] Synthesis of compound 10-9:

[0157] Accurately weigh 2.9 g (2 mmol) of compound 10⁻⁸ into a 100 mL three-necked flask, and add 15 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 0.6 g (4 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) to obtain approximately 2.1 g of compound 10⁻⁹, yield: 69%. MALDI-TOF MS: 1536.95

[0158] Synthesis of compound (10):

[0159] Accurately weigh compound 10⁻⁹ (0.77 g, 0.5 mmol), compound 10⁻² (0.29 g, 1.1 mmol), and 2 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 10 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.77 g of compound (10) was obtained, with a yield of 75%. MALDI-TOF MS: 2035.72.

[0160] Example 3: Synthesis of compound (17)

[0161]

[0162] Synthesis of compound 17-2:

[0163] Accurately weigh compound 17-1 (4.8 g, 5 mmol), compound 10-4 (4.1 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 10:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 5.3 g of compound 17-2, with a yield of 82%. MALDI-TOF MS: 1295.84.

[0164] Synthesis of compound 17-3:

[0165] Accurately weigh 4.5 g (3.5 mmol) of compound 17-2 and 1.3 g (7 mmol) of NBS into a 100 mL three-necked flask, add 40 mL of chloroform and 5 mL of acetic acid. After purging with argon three times, lower the temperature to 0 °C in an ice-salt bath, maintain the reaction temperature at 0 °C for 6 h, allow to rise naturally to room temperature, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM eluent of 8:1 (v / v) to obtain approximately 4.6 g of compound 17-3, yield: 90%. MALDI-TOF MS: 1453.57.

[0166] Synthesis of compound 17-4:

[0167] Accurately weigh compound 17-3 (4.3 g, 3 mmol), compound 10-7 (2.2 g, 6 mmol), and Pd(PPh3)4 (0.07 g, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge the mixture with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 8:1 (v / v) as eluent, separate the product by silica gel column chromatography to obtain approximately 3.7 g of compound 17-4, with a yield of 85%. MALDI-TOF MS: 1460.45.

[0168] Synthesis of compound 17-5:

[0169] Accurately weigh 1.2 g (0.8 mmol) of compound 17-4 into a 100 mL three-necked flask, and add 15 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 0.25 g (1.6 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) as the eluent to obtain approximately 0.8 g of compound 17-5, yield: 66%. MALDI-TOFMS: 1516.44.

[0170] Synthesis of compound (17):

[0171] Accurately weigh compound 17-5 (0.76 g, 0.5 mmol), compound 10-2 (0.29 g, 1.1 mmol), and 2 mL of pyridine, and add them sequentially to a 100 mL three-necked flask. Add 10 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.73 g of compound (17) was obtained, with a yield of 73%. MALDI-TOF MS: 2015.70.

[0172] Example 4: Synthesis of compound (20)

[0173]

[0174] Synthesis of compound 20-2:

[0175] Accurately weigh compound 20-1 (4.5 g, 5 mmol), compound 1-4 (5.5 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 10:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 6.4 g of compound 20-2, with a yield of 84%. MALDI-TOF MS: 1520.61.

[0176] Synthesis of compound 20-3:

[0177] Accurately weigh 6.1 g (4 mmol) of compound 20-2 into a 100 mL three-necked flask, and add 25 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 1.2 g (8 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 2:1 (v / v) as the eluent to obtain approximately 4.8 g of compound 20-3, yield: 77%. MALDI-TOF MS: 1576.72.

[0178] Synthesis of compound (20):

[0179] Accurately weigh compound 20-3 (0.79 g, 0.5 mmol), compound 10-2 (0.29 g, 1.1 mmol), and 2 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 10 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.77 g of compound (20) was obtained, with a yield of 74%. MALDI-TOF MS: 2075.54.

[0180] Example 5: Synthesis of compound (37)

[0181]

[0182] Synthesis of compound 37-2:

[0183] Compound 37-1 (2.7 g, 12 mmol) was accurately weighed into a 100 mL three-necked flask. 30 mL of anhydrous tetrahydrofuran was added, and the mixture was purged with nitrogen three times. The temperature was lowered to -78 °C, and 7.2 mL of n-butyllithium (2.5 M) was slowly added dropwise, maintaining the temperature at -78 °C throughout the process. After stirring for 1 h, tetrabromomethane (5.2 g, 15.6 mmol) was added, and the mixture was stirred at room temperature for 12 h. The reaction was then terminated with distilled water. After extraction with ethyl acetate, the mixture was purified by column chromatography to give approximately 3.1 g of compound 37-2, in 85% yield. MS: 303.58.

[0184] Synthesis of compound 37-4:

[0185] Accurately weigh compound 37-3 (5.3 g, 5 mmol), compound 37-2 (3.0 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 10:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 5.1 g of compound 37-4, in 86% yield. MS: 1191.83.

[0186] Synthesis of compound 37-5:

[0187] Accurately weigh 4.2 g (3.5 mmol) of compound 37-4 and 1.3 g (7 mmol) of NBS into a 100 mL three-necked flask, add 40 mL of chloroform and 5 mL of acetic acid. After purging with argon three times, lower the temperature to 0 °C in an ice-salt bath, maintain the reaction temperature at 0 °C for 6 h, allow to rise naturally to room temperature, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 7:1 (v / v) as eluent to obtain approximately 4.1 g of compound 37-5, yield: 87%. MALDI-TOF MS: 1349.73.

[0188] Synthesis of compound 37-7:

[0189] Compound 37-5 (4.1 g, 3 mmol), compound 37-6 (2.8 g, 6 mmol), and Pd(PPh3)4 (0.07 g, 0.06 mmol) were accurately weighed and added sequentially to a 100 mL three-necked flask. 40 mL of toluene was added, and the mixture was purged with nitrogen three times. The entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase. Using PE:DCM = 8:1 (v / v) as eluent, the mixture was separated by silica gel column chromatography to obtain approximately 3.6 g of compound 37-7, with a yield of 78%. MALDI-TOF MS: 1524.43.

[0190] Synthesis of compound 37-8:

[0191] Accurately weigh 3.1 g (2 mmol) of compound 37-7 into a 100 mL three-necked flask, and add 15 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 0.6 g (4 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) to obtain approximately 1.9 g of compound 37-8, yield: 62%. MALDI-TOF MS: 1580.76.

[0192] Synthesis of compound (37):

[0193] Accurately weigh compound 37-8 (0.79 g, 0.5 mmol), compound 1-2 (0.24 g, 1.1 mmol), and 2 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 10 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.69 g of compound (37) was obtained, with a yield of 70%. MALDI-TOF MS: 1975.53.

[0194] Example 6: Synthesis of compound (52)

[0195]

[0196] Synthesis of compound 52-2:

[0197] Accurately weigh rhodanine (2.7 g, 20 mmol) and potassium hydroxide (3.4 g, 60 mmol) into a 100 mL three-necked flask, and add 50 mL of ethanol. After purging with nitrogen three times, the entire system is heated to 80 °C and stirred for 12 h. After the starting materials have reacted completely, the mixture is cooled in an ice bath, filtered, and the filter cake is washed three times with ethanol to obtain the crude product. The crude product and compound 52-1 (1.8 g, 10 mmol) are added to a 100 mL three-necked flask, and 30 mL of LDM is added. The entire system is heated to 130 °C and stirred for 12 h. After the reaction solution cools, it is poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent is removed by rotary evaporation of the organic phase, and the solution is purified by silica gel column chromatography using PE as the eluent to obtain approximately 3.4 g of compound 52-2, yield: 75%. MS: 227.53.

[0198] Synthesis of compound 52-4:

[0199] Compound 52-3 (5.9 g, 12 mmol) and NBS (2.1 g, 12 mmol) were accurately weighed into a 100 mL three-necked flask. 50 mL of dichloromethane was added, and the system was purged with nitrogen three times. The entire system was heated to reflux for 12 h. After the reaction was complete, the mixture was cooled to room temperature, and excess solvent was removed by vacuum distillation. The solution was purified by silica gel column chromatography using PE as the eluent to give approximately 5.9 g of compound 52-4 (yield: 85%). MS: 577.42.

[0200] Synthesis of compound 52-6:

[0201] Accurately weigh compound 52-5 (4.5 g, 5 mmol), compound 52-4 (5.8 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 8:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 6.9 g of compound 52-6, with a yield of 87%. MALDI-TOF MS: 1572.86.

[0202] Synthesis of compound 52-7:

[0203] Accurately weigh 6.3 g (4 mmol) of compound 52-6 into a 100 mL three-necked flask, and add 30 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 1.2 g (8 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) to obtain approximately 4.4 g of compound 52-7, yield: 67%. MALDI-TOF MS: 1628.60.

[0204] Synthesis of compound 52:

[0205] Accurately weigh compound 52-7 (0.82 g, 0.5 mmol), compound 52-2 (0.25 g, 1.1 mmol), and 2 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 10 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.79 g of compound (52) was obtained, with a yield of 77%. MALDI-TOF MS: 2047.37.

[0206] Example 7: Synthesis of compound (53)

[0207]

[0208] Synthesis of compound 53-2:

[0209] Compound 53-1 (6.5 g, 12 mmol) and NBS (2.1 g, 12 mmol) were accurately weighed into a 250 mL three-necked flask. 70 mL of dichloromethane was added, and the system was purged with nitrogen three times. The entire system was heated to reflux for 12 h. After the reaction was complete, the mixture was cooled to room temperature, and excess solvent was removed by vacuum distillation. The solution was purified by silica gel column chromatography using PE as the eluent to give approximately 6.5 g of compound 53-2 (yield: 87%). MS: 622.43.

[0210] Synthesis of compound 53-4:

[0211] Accurately weigh compound 53-3 (4.5 g, 5 mmol), compound 53-2 (6.2 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 35:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 7.3 g of compound 53-4, with a yield of 88%. MALDI-TOF MS: 1662.65.

[0212] Synthesis of compound 53-5:

[0213] Accurately weigh 6.7 g (4 mmol) of compound 53-4 into a 100 mL three-necked flask, and add 30 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 1.2 g (8 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) as the eluent to obtain approximately 4.9 g of compound 53-5, yield: 71%. MALDI-TOF MS: 1718.69.

[0214] Synthesis of compound 53:

[0215] Accurately weigh compound 53-5 (0.86 g, 0.5 mmol), compound 52-2 (0.25 g, 1.1 mmol), and 2 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 10 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.84 g of compound (53) was obtained, with a yield of 79%. MALDI-TOF MS: 2137.57.

[0216] Example 8: Synthesis of compound (62)

[0217]

[0218] Synthesis of compound 62-2:

[0219] Accurately weigh rhodanine (2.7 g, 20 mmol) and potassium hydroxide (3.4 g, 60 mmol) into a 100 mL three-necked flask, and add 50 mL of ethanol. After purging with nitrogen three times, the entire system was heated to 80 °C and stirred for 12 h. After the reactants had completely reacted, the mixture was cooled in an ice bath, filtered, and the filter cake was washed three times with ethanol to obtain the crude product. The crude product and compound 62-1 (1.9 g, 10 mmol) were added to a 100 mL three-necked flask, and 30 mL of DMF was added. The entire system was heated to 130 °C and stirred for 12 h. After the reaction solution cooled, it was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase, and the solution was purified by silica gel column chromatography using PE as the eluent to obtain approximately 3.7 g of compound 62-2, yield: 77%. MS: 241.16.

[0220] Synthesis of compound 62-5:

[0221] Accurately weigh compound 62-3 (4.7 g, 5 mmol), compound 62-4 (2.8 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 10:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 4.4 g of compound 62-5, in 87% yield. MS: 100 3.33.

[0222] Synthesis of compound 62-6:

[0223] Accurately weigh compound 62-5 (3.9 g, 4 mmol) and NBS (1.4 g, 8 mmol) into a 100 mL three-necked flask, add 40 mL of chloroform and 5 mL of acetic acid. After purging with argon three times, lower the temperature to 0 °C in an ice-salt bath, maintain the reaction temperature at 0 °C for 6 h, allow to rise naturally to room temperature, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 7:1 (v / v) as eluent to obtain approximately 4.3 g of compound 62-6, yield: 92%. MS: 1161.62.

[0224] Synthesis of compound 62-7:

[0225] Compound 62-6 (3.5 g, 3 mmol), compound 37-6 (2.8 g, 6 mmol), and Pd(PPh3)4 (0.07 g, 0.06 mmol) were accurately weighed and added sequentially to a 100 mL three-necked flask. 40 mL of toluene was added, and the mixture was purged with nitrogen three times. The entire reaction system was heated to reflux and reacted for 20 h. After cooling, the reaction solution was poured into water and extracted with EA, then dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation of the organic phase. Using PE:DCM = 10:1 (v / v) as eluent, the mixture was separated by silica gel column chromatography to obtain approximately 3.5 g of compound 62-7, with a yield of 88%. MALDI-TOF MS: 1336.32.

[0226] Synthesis of compound 62-8:

[0227] Accurately weigh 2.68 g (2 mmol) of compound 62-7 into a 100 mL three-necked flask, and add 15 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 0.6 g (4 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) to obtain approximately 1.8 g of compound 62-8, yield: 64%. MALDI-TOF MS: 1392.34.

[0228] Synthesis of compound (62):

[0229] Accurately weigh compound 62-8 (0.7 g, 0.5 mmol), compound 62-2 (0.27 g, 1.1 mmol), and 2 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 100 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.61 g of compound (62) was obtained, with a yield of 67%. MALDI-TOF MS: 1838.44.

[0230] Example 9: Synthesis of compound (63)

[0231]

[0232] Synthesis of compound 63-2:

[0233] Accurately weigh compound 63-1 (4.8 g, 5 mmol), compound 62-4 (2.8 g, 10 mmol), and Pd(PPh3)4 (0.12 g, 0.1 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 10:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 4.2 g of compound 63-2, with a yield of 82%. MS: 1031.45.

[0234] Synthesis of compound 63-3:

[0235] Accurately weigh compound 63-2 (4.1 g, 4 mmol) and NBS (1.4 g, 8 mmol) into a 100 mL three-necked flask, add 40 mL chloroform and 5 mL acetic acid. After purging with argon three times, lower the temperature to 0 °C in an ice-salt bath, maintain the reaction temperature at 0 °C for 6 h, allow to rise naturally to room temperature, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 7:1 (v / v) as eluent to obtain approximately 4.1 g of compound 63-3, yield: 87%. MS: 1189.56.

[0236] Synthesis of compound 63-4:

[0237] Accurately weigh compound 63-3 (3.6 g, 3 mmol), compound 37-6 (2.8 g, 6 mmol), and Pd(PPh3)4 (0.07 g, 0.06 mmol) and add them sequentially to a 100 mL three-necked flask. Add 40 mL of toluene, and purge with nitrogen three times. Heat the entire reaction system to reflux and react for 20 h. After cooling, pour the mixture into water and extract with EA, then dry with anhydrous magnesium sulfate. Remove the solvent by rotary evaporation of the organic phase. Using PE:DCM = 25:1 (v / v) as eluent, separate by silica gel column chromatography to obtain approximately 3.1 g of compound 63-4, with a yield of 75%. MALDI-TOF MS: 1364.23.

[0238] Synthesis of compound 63-5:

[0239] Accurately weigh 2.7 g (2 mmol) of compound 63-4 into a 100 mL three-necked flask, and add 15 mL of DMF. After purging with argon three times, lower the temperature to 0 °C using an ice-salt bath. Weigh 0.6 g (4 mmol) of phosphorus oxychloride and slowly add it dropwise to the reaction system. After the addition is complete, maintain the temperature at 0 °C and stir for 3 h, then allow it to naturally warm to room temperature for 6 h. Quench the reaction solution in water, extract three times with dichloromethane, combine the organic phases, dry them with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform chromatography on a silica gel stirred column with PE:DCM = 10:1 (v / v) to obtain approximately 2.1 g of compound 63-5, yield: 73%. MALDI-TOF MS: 1420.03.

[0240] Synthesis of compound 63:

[0241] Accurately weigh compound 63-5 (0.71 g, 0.5 mmol), compound 52-2 (0.25 g, 1.1 mmol), and 20 mL of piperidine, and add them sequentially to a 100 mL three-necked flask. Add 15 mL of anhydrous chloroform, and heat to 60 °C and stir for 12 hours under argon protection. After the reaction solution cools down, remove excess solvent by vacuum distillation, and then perform chromatography on a silica gel column with PE:DCM = 2:1 (volume ratio) as the eluent. Approximately 0.6 g of compound (63) was obtained, with a yield of 65%. MALDI-TOF MS: 1838.45.

[0242] Fabrication and characterization of OPV devices

[0243] The fabrication process of the OPV device, comprising the aforementioned cycloalkyl-containing small organic molecule compound, is described in detail below through specific device embodiments. The OPV device structure is as follows: Indium Tin Oxide (ITO) / PEDOT:PSS / Active Layer / PDINN / Ag

[0244] Preparation of Device Example 1

[0245] 1) ITO substrate cleaning:

[0246] The ITO conductive glass anode layer was cleaned, followed by ultrasonic cleaning with deionized water, acetone, and isopropanol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode power function.

[0247] 2) Preparation of the anode buffer layer

[0248] PEDOT:PSS was uniformly spin-coated onto ITO in air at a speed of 4000 rpm / min for 30 seconds, and then dried at 150°C for 15 min.

[0249] 3) Preparation of photoactive layer

[0250] In a glove box (inert gas atmosphere), the photoactive layer material is uniformly spin-coated onto the anode buffer layer at a spin speed of 2500 rpm / min for 30 seconds to obtain the active material layer. The donor material in the photoactive layer material is selected from compound (1) provided in this invention; the acceptor material is selected from compound (RM-11) and (RM-20); the mass ratio of organic compound (1): compound (RM-11): compound (RM-20) is 1:1:0.2.

[0251] 4) Preparation of cathode buffer layer

[0252] After hot annealing at 100°C for 10 minutes, the cathode buffer layer material PDINN was uniformly spin-coated onto the active layer at a spin speed of 3000 rpm / min for 30 seconds.

[0253] 5) Cathode layer preparation

[0254] In high vacuum (1×10) -6 Ag is deposited onto the cathode buffer layer in millibars to form a cathode layer with a thickness of 100 nm.

[0255] 6) Packaging

[0256] The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0257] Device Examples 2-9

[0258] The donor material compound (1) in the photoactive layer of device Example 1 was replaced with compound (10), compound (17), compound (20), compound (37), compound (52), compound (53), compound (62), and compound (63), respectively. The other steps were the same, and the devices prepared were recorded as Examples 2 to 9, as detailed in Table 1.

[0259] Comparative Examples of Devices 1-2

[0260] The donor material compound (1) in the photoactive layer of Device Example 1 was replaced with compound REF1 and compound REF2 respectively, and the other steps were the same. The device prepared was referred to as Device Comparative Example 1 and Comparative Example 2.

[0261]

[0262] The organic solar cell device was tested for performance. Under the standard light of AM1.5G from the solar simulator (SS-F5-3A), the current-voltage curve of the cell was tested and the photoelectric conversion efficiency was calculated. The specific values ​​are shown in Table 1.

[0263] Table 1

[0264] Photoactive layer donor materials Photoelectric conversion efficiency (%) Device Example 1 Compound 1 12.36 Device Example 2 Compound 10 15.02 Device Example 3 Compound 17 13.91 Device Example 4 Compound 20 13.39 Device Example 5 Compound 37 14.27 Device Example 6 Compound 52 14.63 Device Example 7 Compound 53 12.67 Device Example 8 Compound 62 13.1 Device Example 9 Compound 63 12.08 Device Comparison Example 1 Compound REF1 9.79 Device Comparison Example 2 compound REF2 10.65

[0265] As shown in Table 1, the photoelectric conversion efficiency of Device Example 1 is improved by 26.25% compared to Device Comparative Example 1; and the photoelectric conversion efficiency of Device Example 3 is improved by 30.61% compared to Device Comparative Example 2. This is because the present invention introduces cycloalkyl groups into the terminal electron-withdrawing unit. Compared to straight-chain or branched alkyl substituents, cycloalkyl groups can significantly reduce energy losses caused by molecular rotation, vibration, and conformational changes, resulting in good stability and heat resistance of the organic compound. Simultaneously, cycloalkyl groups can promote a planar arrangement of molecules, improve carrier transport performance, and effectively achieve exciton charge separation, thereby improving the photoelectric conversion performance of the organic solar cell.

[0266] The preferred embodiments of this application have been described in detail above. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. A naphthenic ring-containing small organic molecule compound, characterized by: The cycloalkyl-containing organic small molecule compound has a structure represented by Formula (I), wherein, Z is, on each occurrence, identically or differently, selected from O or S; Ar1, Ar2is, independently on each occurrence, selected from any one of the following groups: X is, independently on each occurrence, selected from N or CR8; Y is, independently on each occurrence, selected from O or S or Se; W is independently selected at each occurrence from O, S, CR9R 10 , NR 11 ; R8, R9, R 10 , R 11 each occurrence is independently selected from hydrogen, deuterium, halogen, cyano, nitro, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain alkylthio group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a branched alkylthio group having 3 to 20 C atoms, an aromatic group having 6 to 20 carbon atoms, or a heteroaromatic group having 5 to 20 ring atoms, or a group formed by combination of the above-mentioned groups; * indicates the point of attachment; n is selected from 1, 2, 3, or 4; m is selected from 1, 2, 3, or 4; R1, R2are independently selected from the group consisting of linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, linear alkylthio groups having 1 to 20 C atoms, branched alkyl groups having 3 to 20 C atoms, branched alkoxy groups having 3 to 20 C atoms, branched alkylthio groups having 3 to 20 C atoms, unsubstituted or substituted aryl groups having 6 to 20 C atoms, unsubstituted or substituted heteroaryl groups having 5 to 20 ring atoms, or groups formed by a combination of the above mentioned groups; and * unsubstituted or substituted aryl groups having 6 to 20 C atoms, or unsubstituted or substituted heteroaryl groups having 5 to 20 ring atoms, or groups formed by a combination of the above mentioned groups; and * unsubstituted or substituted aryl groups having 6 to 20 C atoms, or unsubstituted or substituted heteroaryl groups having 5 to 20 ring atoms, or groups formed by a combination of the above mentioned groups; and R3is, on each occurrence, identically or differently, selected from any one of the following groups: R * each occurrence is independently selected from deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 20 C atoms, straight-chain alkoxy with 1 to 20 C atoms, straight-chain alkylthio with 1 to 20 C atoms, branched alkyl with 3 to 20 C atoms, branched alkoxy with 3 to 20 C atoms, branched alkylthio with 3 to 20 C atoms, an aromatic radical with 6-20 carbon atoms, a heteroaromatic radical with 5-20 ring atoms, or a group formed by combination of the above-mentioned radicals.

2. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: R1, R2is independently selected from linear alkyl having 1 to 16 C atoms, linear alkoxy having 1 to 16 C atoms, linear alkylthio having 1 to 16 C atoms, branched alkyl having 3 to 16 C atoms, branched alkoxy having 3 to 16 C atoms, branched alkylthio having 3 to 16 C atoms, or any one of the following groups: wherein, R4, R5, R6, R7is, on each occurrence, identically or differently, selected from hydrogen, deuterium, halogen, cyano, nitro, linear alkyl having 1 to 16 C atoms, linear alkoxy having 1 to 16 C atoms, linear alkylthio having 1 to 16 C atoms, branched alkyl having 3 to 16 C atoms, branched alkoxy having 3 to 16 C atoms, branched alkylthio having 3 to 16 C atoms, or a group formed by combination of the above-mentioned groups.

3. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: R1, R2is independently selected from any one of the following structures:

4. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: in the chemical formula (I) is independently selected from any one of the following groups:

5. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: is independently selected from any one of the following groups: wherein, R8, R 11 each occurrence is independently selected from deuterium, halogen, cyano, nitro, straight-chain alkyl with 1 to 10 C atoms, straight-chain alkoxy with 1 to 16 C atoms, straight-chain alkylthio with 1 to 10 C atoms, branched alkyl with 3 to 16 C atoms, branched alkoxy with 3 to 10 C atoms, branched alkylthio with 3 to 10 C atoms.

6. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: in the chemical formula (I) is independently selected from any one of the following groups:

7. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: The selected groups are identical.

8. The organic small-molecule compound containing a cycloalkyl group according to claim 1, characterized by: Formula (I) is selected from any one of the following structural formulas:

9. A mixture characterized in that: The mixture comprises the cycloalkyl-containing organic small molecule compound according to any one of claims 1-8, and at least another organic functional material; the at least another organic functional material is selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material.

10. An organic electronic device comprising at least one functional layer, characterized in that: The functional layer comprises the cycloalkyl-containing organic small molecule compound according to any one of claims 1-8 or the mixture according to claim 9.

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