Acenaphthylene dimer derivatives, processes for their preparation and use

Abstract

The application relates to the field of organic photoelectric materials, and discloses a acenaphthene dimer derivative, a preparation method and application thereof, the acenaphthene dimer derivative has a structure shown in formula (1), wherein R, R3, R4, R5 and R6 are each independently selected from hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group or an alkylthio group. The acenaphthene dimer derivative has both hole transport performance and electron transport performance, has good bipolarity, and has important application value in a field effect transistor.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of organic optoelectronic materials, in particular to a acenaphthene dimer derivative, a preparation method and application thereof. BACKGROUND

[0002] Compared with inorganic semiconductor materials, organic semiconductor materials not only have the advantages of wider material sources, lower cost, and convenient processing, but also have good mechanical flexibility, and have wide application prospects in flexible electronic devices. Moreover, organic semiconductor materials can be applied to the manufacture of solar cells, OLEDs and other devices, and their applications are also expanding with their development. According to the type of carrier transport, semiconductor materials are mainly divided into hole transport type (P-type), electron transport type (N-type) and bipolar type. Compared with pure hole transport type (P-type) and electron transport type (N-type) organic semiconductors, bipolar materials have their unique advantages. When preparing complex circuits, P-type and N-type materials do not need to be deposited separately, which can greatly simplify the preparation process of the device, thereby improving the efficiency and reducing the cost. Therefore, the research on bipolar organic semiconductors is also indispensable.

[0003] The acenaphthene nucleus can construct various functional molecular systems such as cardiacyclic alkenes and decacyclic alkenes, but most of these systems are mainly unipolar hole or electron transport type, and bipolar charge transport type is extremely scarce. SUMMARY

[0004] The purpose of the present application is to overcome the problem of the scarcity of bipolar charge transport type in acenaphthene derivative functional molecular systems in the prior art, and to provide an acenaphthene dimer derivative, a preparation method and application thereof. The acenaphthene dimer derivative has good bipolar performance and has important application value in field effect transistors.

[0005] In order to achieve the above-mentioned purpose, the first aspect of the present application provides an acenaphthene dimer derivative, which has a structure shown in formula (1),

[0006] Formula (1),

[0007] wherein R, R3, R4, R5 and R6 are each independently selected from hydrogen, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group or an alkylthio group.

[0008] The second aspect of the present application provides a preparation method of an acenaphthene dimer derivative, which comprises mixing an acenaphthene derivative, a cyanation reagent, a solvent and an optional copper-containing promoter, and then performing a reaction, wherein the reaction comprises a cyanation reaction and a Ullmann reaction.

[0009] wherein the acenaphthene derivative has a structure shown in formula (2).

[0010] Equation (2),

[0011] R1 and R2 are each independently selected from halogen atoms;

[0012] R, R3, R4, R5, and R6 are each independently selected from hydrogen, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, alkoxy groups, or alkylthio groups.

[0013] The third aspect of the present invention provides an acenaphthene dimer derivative obtained by the above preparation method.

[0014] The fourth aspect of the present invention provides the application of the acenaphthene dimer derivatives described in the first or third aspect above in field-effect transistors.

[0015] The acenaphthene dimer derivative provided by this invention possesses both hole and electron transport properties, exhibiting excellent bipolarity and significant application value in field-effect transistors. This acenaphthene dimer derivative also exhibits a low band gap and good luminescence properties.

[0016] The method for preparing acenaphthene dimer derivatives provided by this invention creatively proposes a novel one-pot domino reaction. With the participation of a cyaniding reagent and an optional copper-containing promoter, cyanidation and Ullman reaction are combined to obtain cyano-substituted coupling dimer structures simply and easily. Attached Figure Description

[0017] Figure 1 The UV-Vis absorption spectrum of a chloroform solution of acenaphthene dimer derivative B1;

[0018] Figure 2 The cyclic voltammetry curves are for the acenaphthene dimer derivative B1.

[0019] Figure 3 This is a schematic diagram of a field-effect transistor device.

[0020] Figure 4 These are the performance transfer curves of organic field-effect transistor devices containing acenaphthene dimer derivative B1. Detailed Implementation

[0021] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0022] The first aspect of the present invention provides an acenaphthene dimer derivative having the structure shown in formula (1).

[0023] Equation (1),

[0024] R, R3, R4, R5, and R6 are each independently selected from hydrogen, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, alkoxy groups, or alkylthio groups.

[0025] According to a specific embodiment of the present invention, the substituted or unsubstituted alkyl group is a straight-chain alkyl group or a branched alkyl group. Preferably, the substituted or unsubstituted alkyl group is a C1-C30 alkyl group, and more preferably a C1-C15 alkyl group, for example, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, n-nonyl, etc. The substituent in the substituted alkyl group is preferably a halogen atom.

[0026] Preferably, the substituted or unsubstituted aryl group is a C6-C30 aryl group, and the substituent in the substituted aryl group is preferably a C1-C20 alkyl or halogen atom. For example, including but not limited to phenyl, fluorophenyl, bromophenyl, chlorophenyl, o-tolyl, p-tolyl, m-tolyl, o-ethylphenyl, p-ethylphenyl, m-ethylphenyl, o-isopropylphenyl, p-isopropylphenyl, m-isopropylphenyl, 1-naphthyl or 2-naphthyl, etc.

[0027] Preferably, the alkylthio group has 1-30 carbon atoms, more preferably 1-20. For example, the alkylthio group includes, but is not limited to, methylthio, ethylthio, propanethio, butanethio, pentanethio, hexanethio, heptanethio, octanethio, nonanethio, decanethio, etc.

[0028] Preferably, the alkoxy group has 1-30 carbon atoms, more preferably 1-20. For example, the alkoxy group includes, but is not limited to, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, etc.

[0029] According to a preferred embodiment of the present invention, R is selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, alkoxy or alkylthio; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, n-nonyl, phenyl, fluorophenyl, bromophenyl, chlorophenyl, o-tolyl, p-tolyl, m-tolyl, o-ethylphenyl, p-ethylphenyl, m-ethylphenyl, o-isopropylphenyl, p-isopropylphenyl, m-isopropylphenyl, 1-naphthyl, 2-naphthyl, methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, nonylthio, decylthio, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octyloxy, nonoxy or decoxy; R3, R4, R5, R6 are hydrogen.

[0030] A second aspect of the present invention provides a method for preparing an acenaphthene dimer derivative, the method comprising: mixing an acenaphthene derivative, a cyaniding reagent, a solvent and an optional copper-containing promoter, and then reacting the mixture, wherein the reaction comprises a cyanidation reaction and a Ullman reaction;

[0031] The acenaphthene derivative has the structure shown in formula (2);

[0032] Equation (2),

[0033] R1 and R2 are each independently selected from halogen atoms;

[0034] R, R3, R4, R5, and R6 are each independently selected from hydrogen, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, alkoxy groups, or alkylthio groups.

[0035] According to a specific embodiment of the present invention, R1 and R2 are each independently selected from fluorine, bromine or chlorine, more preferably bromine.

[0036] In this invention, the definitions of R, R3, R4, R5, and R6 are the same as those described in the first aspect, and will not be repeated here.

[0037] In this invention, the range of cyaniding reagents is relatively wide; any reagent capable of achieving the cyanidation reaction is acceptable. Those skilled in the art can select the appropriate reagent based on actual needs. Preferably, the cyaniding reagent is selected from at least one of cuprous cyanide, zinc cyanide, and potassium ferrocyanide.

[0038] According to the present invention, preferably, the amount of the cyaniding agent is 8-100 equivalents relative to 1 equivalent of the acenaphthene derivative. For example, it can be a specific amount or a range between the two, such as 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100 equivalents.

[0039] In this invention, the selection range of the copper-containing promoter is relatively wide, as long as it can promote the Ullmann reaction. Those skilled in the art can select according to the actual situation. Preferably, the copper-containing promoter is a monovalent copper compound, preferably at least one of cuprous cyanide, cuprous chloride, cuprous bromide, and cuprous iodide. It is understood that when the cyaniding reagent contains monovalent copper, the cyaniding reagent can both participate in the cyanidation reaction and promote the Ullmann reaction. In this case, no additional copper-containing promoter is needed.

[0040] Preferably, the amount of the copper-containing accelerator is 8-100 equivalents relative to 1 equivalent of the acenaphthene derivative. For example, it can be a specific amount or a range between the two, such as 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100 equivalents.

[0041] According to the present invention, preferably, the reaction temperature is 100-300℃, for example, it can be a specific temperature point or a range between two points, such as 100℃, 105℃, 110℃, 115℃, 120℃, 125℃, 130℃, 135℃, 140℃, 145℃, 150℃, 155℃, 160℃, 165℃, 170℃, 175℃, 180℃, 185℃, 190℃, 195℃, 200℃, 205℃, 210℃, 215℃, 220℃, 230℃, 240℃, 250℃, 260℃, 270℃, 280℃, 290℃, 300℃, etc. According to a preferred embodiment of the present invention, the reaction temperature is 150-220℃.

[0042] According to the present invention, preferably, the reaction time is 12-48 hours; for example, the reaction time can be a specific reaction time such as 12 hours, 14 hours, 16 hours, 18 hours, 20 hours, 22 hours, 24 hours, 26 hours, 28 hours, 30 hours, 32 hours, 34 hours, 36 hours, 38 hours, 40 hours, 42 hours, 44 hours, 46 hours, 48 ​​hours, etc.

[0043] Preferably, the reaction is carried out under a protective atmosphere, which is preferably provided by at least one of nitrogen, argon and neon.

[0044] Preferably, the reaction is carried out under stirring conditions. The present invention does not have any particular limitation on the stirring conditions, as long as they can promote the reaction.

[0045] In this invention, preferably, the preparation method further includes purifying the product obtained from the reaction. The purification can be carried out using methods conventional in the art, and those skilled in the art can choose according to the actual situation. For example, silica gel column purification can be used.

[0046] According to a specific embodiment of the present invention, the method for preparing the acenaphthene derivative includes:

[0047] S1. The acenaphthene nucleus is subjected to a Friedel-Crafts acylation reaction;

[0048] S2. The product obtained in step S1 is subjected to halogenation, anhydrideation and amidation reactions.

[0049] The acenaphthene nucleus has the structure shown in formula (3).

[0050] Equation (3),

[0051] The definitions of R3, R4, R5, and R6 are the same as those mentioned above.

[0052] In this invention, the Friedel-Crafts acylation reaction refers to the Friedel-Crafts acylation reaction. This invention does not impose any particular limitations on the conditions of the Friedel-Crafts acylation reaction, and it can be carried out according to conditions known in the art. For example, it can be carried out according to the method reported by Barattin, R et al. (Eur. J. Org. Chem. 2009, 2009, 1022–1026).

[0053] According to the present invention, the structure of the product obtained after the Friedel-Crafts acylation reaction of the acenaphthene core can be represented as follows: .

[0054] In this invention, the order of the halogenation, anhydrideation, and amidation reactions in step S2 can be adjusted according to actual conditions. For example, the halogenation, anhydrideation, and amidation reactions can be performed sequentially; alternatively, the anhydrideation and amidation reactions can be performed first, followed by the halogenation reaction; or the amidation reaction can be performed first, followed by the halogenation and anhydrideation reactions. Preferably, the halogenation, anhydrideation, and amidation reactions are performed sequentially. Using the above-mentioned preferred reaction route is beneficial for obtaining higher yields and simpler, safer reaction conditions.

[0055] According to the present invention, the Friedel-Crafts acylation reaction, halogenation reaction, anhydride reaction, and amidation reaction may also independently include purifying the product obtained from the reaction. The purification may include one or a combination of several of the following methods: solid-liquid separation, washing, recrystallization, elution purification, etc., which may be selected by those skilled in the art according to actual needs; the present invention does not impose any particular limitation on this.

[0056] According to a preferred embodiment of the present invention, step S2 includes:

[0057] S2-1. Contact the product obtained in step S1 with a halogenating reagent to carry out a halogenation reaction;

[0058] S2-2, The product of the halogenation reaction is brought into contact with an acid to carry out anhydride reaction;

[0059] S2-3. The product of the anhydride reaction is contacted with an amine compound to carry out an amidation reaction;

[0060] The amine compounds have the general formula R-NH2, and the definition of R is the same as that involved in the first aspect.

[0061] The reaction route of this preferred embodiment can be represented by reaction formula (A):

[0062]

[0063] Formula (A),

[0064] In this invention, the general formula of the amine compound is R-NH2, meaning that the amine compound can provide an R group. The selection of R has been explained in detail above and will not be repeated here.

[0065] According to a specific embodiment of the present invention, the halogenation reaction is a bromination reaction, a fluorination reaction, or a chlorination reaction. The present invention provides a wide range of choices for the specific conditions of the halogenation reaction, as long as halogen substitution can be achieved. The amount of the halogenating reagent can be selected according to the actual needs of the reaction.

[0066] According to a preferred embodiment of the present invention, the halogenation reaction is a bromination reaction, and the conditions for the bromination reaction include: a reaction temperature of 70-100℃, for example, a specific temperature or a range between temperatures such as 70℃, 72℃, 74℃, 76℃, 78℃, 80℃, 82℃, 84℃, 86℃, 88℃, 90℃, 92℃, 94℃, 96℃, 98℃, and 100℃.

[0067] Preferably, the reaction time is 1-10 hours, for example, typical times such as 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, and 10 hours.

[0068] In this invention, the range of halogenating reagents is relatively wide, as long as the halogenation reaction can be achieved. Conventional halogenating reagents in the art can be used in this invention, and those skilled in the art can select according to reagent requirements.

[0069] For example, when the halogenation reaction is a bromination reaction, the halogenating agent is preferably at least one of N-bromosuccinimide, liquid bromine, 1,3-dibromo-5,5-dimethylhydantoin, dibromoisocyanuric acid, and 1,3,5-tribromo-1,3,5-triazine-2,4,6-trione, preferably N-bromosuccinimide and / or liquid bromine.

[0070] In this invention, preferably, the amount of the halogenating agent used is 1-10 equivalents relative to 1 equivalent of the product obtained in step S1, for example, it can be any one or a range between two points from 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10. Preferably, the amount of the halogenating agent used is 4-10 equivalents relative to 1 equivalent of the product obtained in step S1.

[0071] According to a specific embodiment of the present invention, the preparation method further includes: introducing an oxidizing agent in step S2-1, which is beneficial to obtain unsaturated double bonds simultaneously with bromination. The oxidizing agent is preferably at least one selected from benzoyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, and tert-butanol peroxide, with benzoyl peroxide being more preferred.

[0072] Preferably, the amount of the oxidizing agent is 0.01-1 equivalent relative to 1 equivalent of the product obtained in step S1, for example, typical but not limiting amounts such as 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, etc.

[0073] Preferably, the halogenation reaction is carried out in the presence of the first solvent.

[0074] In this invention, there is no particular limitation on the specific type of the first solvent, and conventional organic solvents in the art can be used. Preferably, the first solvent is a halogenated hydrocarbon, and more preferably, the halogenated hydrocarbon is selected from at least one of chloromethane, dichloromethane, trichloromethane, tetrachloromethane, tetrachloroethane, 1-chloropropane, 2-chloropropane, n-chlorobutane, 2-chlorobutane, chloroisobutane, sec-chlorobutane, tert-chlorobutane, n-bromopropane, bromoisopropane, 1-bromobutane, and 2-bromobutane, and more preferably at least one of dichloromethane, trichloromethane, and tetrachloromethane.

[0075] According to a specific embodiment of the present invention, the temperature of the anhydride reaction is 60-100℃, for example, it can be a specific temperature point or a range between two points such as 60℃, 62℃, 64℃, 66℃, 68℃, 70℃, 72℃, 74℃, 76℃, 78℃, 80℃, 82℃, 84℃, 86℃, 88℃, 90℃, 92℃, 94℃, 96℃, 98℃, 100℃.

[0076] Preferably, the anhydride reaction takes 4-10 hours, for example, typical times such as 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, and 10 hours.

[0077] The present invention has a wide range of choices for the acid. For example, the acid can be selected from inorganic acids and / or organic acids, preferably at least one of hydrochloric acid, hydrobromic acid, sulfuric acid and acetic acid.

[0078] According to a specific embodiment of the present invention, the amount of acid used is 12-100 equivalents relative to 1 equivalent of the product of the halogenation reaction.

[0079] In this invention, in order to ensure the full progress of the anhydride reaction, preferably, the acid can be added in steps. The anhydride reaction includes: contacting the product of the halogenation reaction with the first acid to carry out the anhydride reaction for 3-4 hours, and then adding the second acid to the reaction system and continuing the reaction until the reaction is completed.

[0080] Preferably, the mass ratio of the second acid to the first acid is 0.5-1:1, for example, it can be a specific ratio such as 0.5:1, 0.55:1, 0.6:1, 0.65:1, 0.7:1, 0.75:1, 0.8:1, 0.85:1, 0.9:1, 0.95:1, 1:1, etc.

[0081] In this invention, the acid may be derived from an acid or an aqueous solution of an acid, and when the acid is provided by an aqueous solution of an acid, the concentration of the aqueous solution of the acid may be 36-98 wt%.

[0082] Preferably, the anhydride reaction is carried out under stirring conditions. The present invention does not have particular limitations on the stirring conditions, as long as they promote the reaction.

[0083] According to a specific embodiment of the present invention, the reaction temperature of the amidation reaction is 80-150°C, for example, it can be a specific temperature point or a range between two points such as 80°C, 82°C, 84°C, 86°C, 88°C, 90°C, 92°C, 94°C, 96°C, 98°C, 100°C, 105°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C.

[0084] Preferably, the reaction time of the amidation reaction is 36-60h, for example, it can be a specific time such as 36h, 38h, 40h, 42h, 44h, 46h, 48h, 50h, 52h, 54h, 56h, 58h, 60h.

[0085] According to a preferred embodiment of the present invention, the conditions for the amidation reaction include: first reacting at a low temperature of 80-100°C for 12-24 hours, and then reacting at a high temperature of 110-140°C for 12-48 hours; for example, the reaction temperature of the low-temperature reaction section can be a specific temperature such as 0°C, 82°C, 84°C, 86°C, 88°C, 90°C, 92°C, 94°C, 96°C, 98°C, 100°C, etc.; the reaction temperature of the high-temperature reaction section can be a specific temperature such as 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, etc.

[0086] According to one specific embodiment of the present invention, the amidation reaction is carried out under a protective atmosphere, which is preferably provided by at least one of nitrogen, argon and neon.

[0087] According to the present invention, preferably, the amidation reaction is carried out in the presence of a second solvent. The specific type of the second solvent is not particularly limited, and conventional organic solvents in the art can be used. Preferably, the second solvent is an amide compound or glacial acetic acid, and the amide compound may be, for example, at least one selected from N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylpropionamide, and N,N-dimethylbutyramide.

[0088] The present invention does not have a particular limitation on the order of addition of the materials in the amidation reaction. The product of the acid anhydride reaction, the amine compound, and the second solvent can be added to the reactor together for mixing, or the second solvent can be added first, and then the product of the acid anhydride reaction and the amine compound can be added.

[0089] According to a preferred embodiment of the present invention, the amount of the amine compound used is 1-3 equivalents relative to 1 equivalent of the product of the anhydride reaction, for example, it can be a specific equivalent value such as 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, etc.

[0090] The third aspect of the present invention provides an acenaphthene dimer derivative prepared by the above preparation method.

[0091] The acenaphthene dimer derivative has the structure shown in formula (1).

[0092] Equation (1),

[0093] R, R3, R4, R5, and R6 are each independently selected from hydrogen, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, alkoxy groups, or alkylthio groups.

[0094] The acenaphthene dimer derivatives provided by this invention have good luminescence efficiency and performance, as well as high hole mobility and electron mobility, and good bipolarity.

[0095] The fourth aspect of the present invention provides the application of the above-mentioned acenaphthene dimer derivative in field-effect transistors.

[0096] The present invention will be described in detail below through embodiments.

[0097] Unless otherwise specified, all raw materials used in the following embodiments are commercially available.

[0098] In the following examples, the structure of the products of each step was determined by 1H NMR spectroscopy.

[0099] In the following examples, room temperature refers to 25±5℃.

[0100] In the following examples, the yield (%) of each step = (actual yield / theoretical yield) × 100%.

[0101] The following preparation examples illustrate the preparation of acenaphthene derivatives.

[0102] Preparation Example A1

[0103] S1, with acenaphthene nucleus Using the raw materials, Friedel-Crafts acylation was carried out according to the method described in the literature Barattin, R.; Gourdon, A. Eur. J.Org. Chem. 2009, 2009, 1022–1026.

[0104] S2-1: 8.88 g (30.0 mmol, 1 eq) of the product obtained in step S1 was placed in a 250 mL inclined two-necked flask, and 75 mL of carbon tetrachloride was added. The mixture was heated and stirred at 50 °C until a homogeneous solution was obtained. 32.04 g (180.0 mmol, 6 eq) of N-bromosuccinimide and 0.729 g (3.0 mmol, 0.1 eq) of benzoyl peroxide were added to the above solution to initiate a bromination reaction. The mixture was heated to 80 °C and refluxed with stirring for 4 hours. After the reaction was complete, the solution was extracted with dichloromethane, and the organic phase was washed with saturated sodium thiosulfate aqueous solution and water. The bromination product was purified by silica gel column chromatography using ethyl acetate as the eluent. The product was a yellow solid, weighing 2.6 g, with a yield of 20%.

[0105] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 436.98; 1 H NMR (400 MHz, Chloroform- d ) δ 7.63 (d, J = 7.1 Hz, 2H), 7.43 (d, J = 7.1 Hz, 2H), 3.09 (s, 3H), 2.87 (s, 3H).

[0106] S2-2. 2.25 g (5 mmol, 1 eq) of the above bromination product was added to a 100 mL inclined two-necked flask, along with 21 mL of concentrated hydrochloric acid (36-38 wt%, 50.4 eq). The mixture was heated to 70 °C and stirred for 3 h. Then, 10 mL of concentrated hydrochloric acid was added, and the reaction was continued at 70 °C for another 4 h. After heating was completed, the two-necked flask was placed in an ice-water bath. The precipitate was then collected by suction filtration and washed with copious amounts of water. Recrystallization from chloroform yielded the anhydride product, a deep red solid weighing 0.675 g, with a yield of 35%.

[0107] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 379.86; 1 H NMR (400 MHz, Chloroform- d ) δ 8.50 (d, J = 7.2 Hz, 2H), 7.84 (d, J = 7.2 Hz, 2H).

[0108] S2-3. Add 0.379 g (1 mmol, 1 eq) of the anhydride reaction product to a 25 mL inclined two-necked flask, along with 0.155 g (1.2 mmol, 1.2 eq) of n-octylamine and 5 mL of DMF. React at 90 °C for 12 hours under a nitrogen atmosphere, then immediately raise the temperature to 110 °C and continue the reaction for another 12 hours. Extract the solution with dichloromethane and wash the organic phase with water. Using dichloromethane as the eluent, purify the amidation product by silica gel column chromatography. The product is a dark red solid, weighing 0.328 g, with a yield of 67%.

[0109] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 491.02; 1 H NMR (400 MHz, Chloroform- d ) δ 8.35 (d, J = 7.2 Hz, 2H), 7.70 (d, J = 7.2 Hz, 2H), 4.16 – 4.08(t, 2H), 1.55 (p, 2H), 1.32 –1.25 (m, 8H), 0.87 (m, J = 6.1, 5.6, 3.3 Hz, 3H), proving that the structure of the obtained acenaphthene derivative is as shown in formula (2), where R is n-octyl, R1 and R2 are bromine atoms, and R3, R4, R5 and R6 are hydrogen atoms. This acenaphthene derivative is denoted as A1.

[0110] Preparation Example A2

[0111] The method is the same as that used in preparation example A1, except that steps S2-3 include:

[0112] 0.379 g (1 mmol, 1 eq) of the anhydride reaction product was added to a 38 mL pressurized reaction tube, along with 0.088 g (1.2 mmol, 1.2 eq) of n-butylamine and 15 mL of glacial acetic acid. The reaction was carried out at 112 °C for 12 hours under a nitrogen atmosphere. The solution was extracted with dichloromethane, and the organic phase was washed with water. The amidation product was obtained by silica gel column chromatography using dichloromethane as the eluent; it was a dark red solid weighing 0.185g, with a yield of 42%.

[0113] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 434.94; 1 H NMR (400 MHz, Chloroform- d) δ 8.28 (d, J = 7.5 Hz, 2H), 8.00 (d, J = 7.5 Hz, 2H), 3.46 (t, J = 7.1 Hz, 2H), 1.65 (p, J = 7.1 Hz, 2H), 1.41 – 1.30 (m, 2H), 0.96 (t, J = 8.0 Hz, 3H), proving that the structure of the obtained acenaphthene derivative is as shown in formula (2), where R is n-butyl, R1 and R2 are bromine atoms, and R3, R4, R5 and R6 are hydrogen atoms. This acenaphthene derivative is denoted as A2.

[0114] Preparation Example A3

[0115] S1, with acenaphthene nucleus Using the raw materials, Friedel-Crafts acylation was carried out according to the method described in the literature Barattin, R.; Gourdon, A. Eur. J.Org. Chem. 2009, 2009, 1022–1026.

[0116] S2-1. Add 2 g (6.75 mmol, 1 eq) of the product obtained in step S1 to a 100 mL inclined two-necked flask, add 5 mL of concentrated hydrochloric acid (36-38 wt%, 68.04 eq), heat to 70 °C, and stir for 5 h. Add another 5 mL of concentrated hydrochloric acid and continue the reaction at 70 °C for 4 h. After heating is complete, place the two-necked flask in an ice-water bath, then filter to collect the precipitate, wash with plenty of water, and recrystallize from acetic anhydride solution to obtain the anhydride reaction product, weighing 0.68 g, with a yield of 39%.

[0117] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 224.01; 1 H NMR (400 MHz, Chloroform- d ) δ 8.54 (d, 2H, 3 J = 7.0 Hz, Np), δ 7.65 (d, 2H, 3 J = 7.0 Hz, Np), δ 3.45 ppm (s, 4H, CH2).

[0118] S2-2: 2.24 g (10 mmol, 1 eq) of the reaction product from S2-1 was added to a 250 mL inclined two-necked flask, along with 100 mL of carbon tetrachloride. The mixture was heated and stirred at 50 °C until a homogeneous solution was obtained. Then, 10.6 g (60 mmol, 6 eq) of N-bromosuccinimide and 0.24 g (1 mmol, 0.1 eq) of benzoyl peroxide were added to the above solution for bromination. The mixture was heated to 80 °C and refluxed with stirring for 4 hours. After the reaction was complete, the red precipitate was collected by filtration and washed with a large amount of sodium bicarbonate solution and deionized water. Recrystallization from chloroform yielded a red solid, 405.5 mg, with a yield of 10.6%.

[0119] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 379.86; 1 H NMR (400 MHz, Chloroform- d ) δ 8.50 (d, J = 7.2 Hz, 2H), 7.84 (d, J = 7.2 Hz, 2H).

[0120] S2-3: Add 0.379 g (1 mmol, 1 eq) of the product obtained in S2-2 to a 25 mL inclined two-necked flask, along with 0.155 g (1.2 mmol, 1.2 eq) of n-octylamine and 5 mL of DMF. React at 90 °C for 12 hours under a nitrogen atmosphere, then immediately raise the temperature to 110 °C and continue the reaction for another 12 hours. Extract the solution with dichloromethane and wash the organic phase with water. Using dichloromethane as the eluent, purify the amidation product by silica gel column chromatography; the product is a deep red solid, weighing 0.328 g, with a yield of 67%.

[0121] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 491.02; 1 H NMR (400 MHz, Chloroform- d ) δ 8.35 (d, J = 7.2 Hz, 2H), 7.70 (d, J = 7.2 Hz, 2H), 4.16 – 4.08(t, 2H), 1.55 (p, 2H), 1.32 –1.25 (m, 10H), 0.87 (m, J = 6.1, 5.6, 3.3 Hz, 3H), proving that the structure of the obtained acenaphthene derivative is as shown in formula (2), where R is n-octyl, R1 and R2 are bromine atoms, and R3, R4, R5 and R6 are hydrogen atoms. This acenaphthene derivative is denoted as A3.

[0122] In this preparation example, the anhydride reaction is performed first, followed by the halogenation reaction, and then the product of the halogenation reaction is amidated. By changing the reaction order, the target product can still be obtained, although the product yield is slightly lower than that of Preparation Example 1.

[0123] Preparation Example A4

[0124] S1, with acenaphthene nucleus Using the raw materials, Friedel-Crafts acylation was carried out according to the method described in the literature Barattin, R.; Gourdon, A. Eur. J.Org. Chem. 2009, 2009, 1022–1026.

[0125] S2-1: 17.76 g (60.0 mmol, 1 eq) of the product obtained in step S1 was placed in a 1000 mL inclined two-necked flask, and 150 mL of carbon tetrachloride was added. The mixture was heated and stirred at 50 °C until a homogeneous solution was obtained. 64.08 g (360.0 mmol, 6 eq) of N-bromosuccinimide and 1.458 g (6.0 mmol, 0.1 eq) of benzoyl peroxide were added to the above solution for bromination. The mixture was heated to 80 °C and refluxed with stirring for 4 hours. After the reaction was complete, the solution was extracted with dichloromethane, and the organic phase was washed with saturated sodium thiosulfate aqueous solution and water. The bromination product was purified by silica gel column chromatography using ethyl acetate as the eluent. The product was a yellow solid, weighing 5.2 g, with a yield of 20%.

[0126] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 436.98; 1 H NMR (400 MHz, Chloroform- d ) δ 7.63 (d, J = 7.1 Hz, 2H), 7.43 (d, J = 7.1 Hz, 2H), 3.09 (s, 3H), 2.87 (s, 3H).

[0127] S2-2. 4.5 g (10 mmol, 1 eq) of the above bromination product was added to a 250 mL inclined two-necked flask, along with 42 mL of concentrated hydrochloric acid (36-38 wt%, 50.4 eq). The mixture was heated to 70 °C and stirred for 3 h. Then, 10 mL of concentrated hydrochloric acid was added, and the reaction was continued at 70 °C for another 4 h. After heating was completed, the two-necked flask was placed in an ice-water bath. The precipitate was then collected by suction filtration and washed with copious amounts of water. Recrystallization from chloroform yielded the anhydride product, a dark red solid weighing 1.35 g, with a yield of 35%.

[0128] S2-3. 1.137 g (3 mmol, 1 eq) of the anhydride reaction product was added to a 100 mL inclined two-necked flask, along with 0.335 g (3.6 mmol, 1.2 eq) of aniline and 25 mL of DMF. The reaction was carried out at 90 °C for 12 hours under a nitrogen atmosphere, followed by raising the temperature to 110 °C and continuing the reaction for another 12 hours. The solution was extracted with dichloromethane, and the organic phase was washed with water. Using dichloromethane as the eluent, the amidation product was purified by silica gel column chromatography. The product was a dark red solid, weighing 0.525 g, with a yield of 32%.

[0129] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 436.98; 1 H NMR (400 MHz, Chloroform- d ) δ 8.39 (d, J = 7.5 Hz, 2H), 8.03 (d, J = 7.5 Hz, 2H), 7.50 –7.43 (m, 2H), 7.46 – 7.38 (m, 3H), proving that the structure of the obtained acenaphthene derivative is as shown in formula (2), where R is phenyl, R1 and R2 are bromine atoms, and R3, R4, R5 and R6 are hydrogen atoms. This acenaphthene derivative is denoted as A4.

[0130] Preparation Example A5

[0131] The method is the same as in Example A4, except that steps S2-3 include: adding 1.137 g (3 mmol, 1 eq) of the anhydride reaction product to a 100 mL inclined two-necked flask, adding 0.639 g (3.6 mmol, 1.2 eq) of 2,6-diisopropylaniline, and 25 mL of DMF. The reaction is carried out at 90 °C for 12 hours under a nitrogen atmosphere, followed by raising the temperature to 110 °C and continuing the reaction for another 12 hours. The solution is extracted with dichloromethane, and the organic phase is washed with water. The amidation reaction product, a dark red solid weighing 0.836 g (51% yield), is obtained by silica gel column chromatography using dichloromethane as the eluent.

[0132] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 538.98; 1 H NMR (400 MHz, Chloroform- d) δ 8.41 (d, J = 7.5 Hz, 2H), 8.04 (d, J = 7.5 Hz, 2H), 7.26 (dd, J = 8.1, 6.7 Hz, 1H), 7.18 (dd, J = 7.4, 0.8 Hz, 2H), 3.18 – 3.06 (m, 2H), 1.19 (d, J = 6.8 Hz, 12H), proving that the structure of the obtained acenaphthene derivative is as shown in formula (2), where R is 2,6-diisopropylphenyl, R1 and R2 are bromine atoms, and R3, R4, R5 and R6 are hydrogen atoms. This acenaphthene derivative is denoted as A5.

[0133] Preparation Example A6

[0134] The method is the same as in Example A4, except that steps S2-3 include: adding 1.137 g (3 mmol, 1 eq) of the anhydride reaction product to a 38 mL pressurized reaction tube, along with 6 mL of ethanol and 7.5 mL of ammonia. The reaction is carried out at 70 °C for 12 hours under a nitrogen atmosphere, cooled to room temperature, filtered, and washed with n-hexane to give 0.66 g of a red solid, with a yield of 61%.

[0135] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 378.85; 1 H NMR (400 MHz, Chloroform- d ) δ 8.33 (d, J = 7.5 Hz, 2H), 8.01 (d, J = 7.5 Hz, 2H), proving that the structure of the obtained acenaphthene derivative is as shown in formula (2), where R is a hydrogen atom, R1 and R2 are bromine atoms, and R3, R4, R5 and R6 are hydrogen atoms. This acenaphthene derivative is denoted as A6.

[0136] The following examples illustrate the preparation of acenaphthene dimer derivatives.

[0137] Example B1

[0138] 200 mg (0.40 mmol, 1 eq) of acenaphthene derivative A1, 0.574 g (6.4 mmol, 16 eq) of cuprous cyanide, and 2 mL of N,N-dimethylformamide were added to a reaction tube and mixed. The mixture was stirred and heated to 160 °C for 18 h under a nitrogen atmosphere. The solution was extracted with dichloromethane, and the organic phase was washed with brine. Using dichloromethane as the eluent, the solution was purified by silica gel column chromatography to obtain acenaphthene dimer derivative B1, a blue-purple solid weighing 0.048 g, with a calculated yield of 36%.

[0139] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 714.259;1 ¹H NMR (400 MHz, Chloroform-d) δ 9.26 (d, J = 8.1 Hz, 2H), 8.86 (d, J = 8.1 Hz, 2H), 8.79 (d, J = 7.9 Hz, 2H), 8.47 (d, J = 7.9 Hz, 2H), 4.24 (t, J = 7.6 Hz, 4H). The structure of the obtained acenaphthene dimer derivative B1 is shown in formula (1), where R is n-octyl, and R3, R4, R5, and R6 are hydrogen atoms.

[0140] Figure 1 A chloroform solution of acenaphthene dimer derivative B1 (10 -5 The UV-Vis absorption spectrum of M) is shown in the figure. As can be seen from the figure, the compound exhibits three main absorption peaks at 617 nm, 325 nm and 550 nm, with an optical band gap of 1.55 eV.

[0141] A three-electrode system was used: a glassy carbon monoelectrode as the working electrode, a platinum wire as the counter electrode, Ag / AgCl as the reference electrode, and tetrabutylammonium hexafluorophosphate as the electrolyte. The test conditions were -2.5–1.5 V, with a scan rate of 100 mV / s. The cyclic voltammetry curves of the acenaphthene dimer derivative B1 in dichloromethane solution were obtained, as shown below. Figure 2 As shown, the LUMO can be calculated to be -4.29 eV, and the HOMO can be calculated to be -5.84 eV. This indicates that the introduction of the cyano group significantly reduces the LUMO energy level of the compound, while the narrower band gap makes it possible for this compound to be used as a bipolar material.

[0142] The luminescence efficiency of a dichloromethane solution containing acenaphthene dimer derivative B1 was tested using a photoluminescence efficiency measurement system (PLQY). The measured efficiency was 1.0 × 10⁻⁶. -6 The PLQY of the dichloromethane solution of the acenaphthene dimer derivative B1 of M was 47.8%, indicating that the acenaphthene dimer derivative has good luminescence efficiency and performance.

[0143] Example B2

[0144] 200 mg (0.46 mmol, 1 eq) of acenaphthene derivative A2, 0.414 g (4.6 mmol, 10 eq) of cuprous cyanide, and 2 mL of N,N-dimethylformamide were added to a reaction tube and mixed. The mixture was stirred and heated to 160 °C for 18 h under a nitrogen atmosphere. The solution was extracted with dichloromethane and the organic phase was washed with brine. Using dichloromethane as the eluent, the acenaphthene dimer derivative B2 was purified by silica gel column chromatography. The solid was a blue-purple color and weighed 0.038 g, with a calculated yield of 14%. The structure of the obtained acenaphthene dimer derivative B1 was shown in formula (1), where R is n-butyl and R3, R4, R5, and R6 are hydrogen atoms.

[0145] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 602.21; 1 ¹H NMR (400 MHz, Chloroform-d) δ 8.39 (d, J = 7.5 Hz, 2H), 8.06 (d, J = 7.5 Hz, 2H), 7.94 (d, J = 7.5 Hz, 2H), 7.79 (d, J = 7.5 Hz, 2H), 3.86 (t, J = 7.1 Hz, 4H), 1.64 (p, J = 7.1 Hz, 4H), 1.36 (dtd, J = 15.2, 7.9, 6.9 Hz, 4H), 0.96 (t, J = 8.0 Hz, 6H), proving that the structure of the obtained acenaphthene dimer derivative B2 is as shown in formula (1), where R is n-butyl and R3, R4, R5, and R6 are hydrogen.

[0146] Example B3

[0147] 182 mg (0.40 mmol, 1 eq) of acenaphthene derivative A4, 0.574 g (6.4 mmol, 16 eq) of cuprous cyanide, and 2 mL of N,N-dimethylformamide were added to a reaction tube and mixed. The mixture was stirred and heated to 160 °C for 18 h under a nitrogen atmosphere. The solution was extracted with dichloromethane, and the organic phase was washed with brine. Using dichloromethane as the eluent, the solution was purified by silica gel column chromatography to obtain acenaphthene dimer derivative B5, a blue-purple solid weighing 0.029 g, with a calculated yield of 11%.

[0148] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 642.11; 1¹H NMR (400 MHz, Chloroform-d) δ 8.46 (d, J = 7.5 Hz, 1H), 8.16 – 8.08 (m, 2H), 7.83 (dd, J = 22.7, 7.5 Hz, 1H), 7.51 – 7.39 (m, 5H), confirming that the structure of the obtained acenaphthene dimer derivative B3 is as shown in formula (1), where R is phenyl and R3, R4, R5, and R6 are hydrogen atoms.

[0149] Example B4

[0150] 216 mg (0.40 mmol, 1 eq) of acenaphthene derivative A5, 0.574 g (6.4 mmol, 16 eq) of cuprous cyanide, and 2 mL of N,N-dimethylformamide were added to a reaction tube and mixed. The mixture was stirred and heated to 160 °C for 18 h under a nitrogen atmosphere. The solution was extracted with dichloromethane, and the organic phase was washed with brine. Using dichloromethane as the eluent, the solution was purified by silica gel column chromatography to obtain acenaphthene dimer derivative B4, a blue-purple solid weighing 0.044 g, with a calculated yield of 13%.

[0151] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 810.30; 1 ¹H NMR (400 MHz, Chloroform-d) δ 8.45 (d, J = 7.5 Hz, 1H), 8.12 (d, J = 7.5 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.30 – 7.24 (m, 1H), 7.24 – 7.20 (m, 2H), 3.20 – 3.08 (m, 2H), 1.20 (d, J = 6.8 Hz, 12H), confirming that the structure of the obtained acenaphthene dimer derivative B4 is as shown in formula (1), where R is 2,6-diisopropylphenyl, and R3, R4, R5, and R6 are hydrogen atoms.

[0152] Example B5

[0153] 152 mg (0.40 mmol, 1 eq) of acenaphthene derivative A6, 0.574 g (6.4 mmol, 16 eq) of cuprous cyanide, and 2 mL of N,N-dimethylformamide were added to a reaction tube and mixed. The mixture was stirred and heated to 160 °C for 18 h under a nitrogen atmosphere. The solution was extracted with dichloromethane, and the organic phase was washed with brine. Using dichloromethane as the eluent, the solution was purified by silica gel column chromatography to obtain acenaphthene dimer derivative B5, a blue-purple solid weighing 0.044 g, with a calculated yield of 13%.

[0154] The structure of the product was confirmed by 1H NMR spectroscopy: MS (MALDI-TOF): 490.72; 1 ¹H NMR (400 MHz, Chloroform-d) δ 8.36 (d, J = 7.5 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 8.05 (d, J = 7.5 Hz, 1H), 7.84 (d, J = 7.5 Hz, 1H), proving that the structure of the obtained acenaphthene dimer derivative B5 is as shown in formula (1), where R is a hydrogen atom, and R3, R4, R5, and R6 are hydrogen atoms.

[0155] The acenaphthene dimer derivatives obtained in the above embodiments were used to prepare organic field-effect transistor devices and their performance was tested.

[0156] A schematic diagram of an organic field-effect transistor device is shown below. Figure 3 As shown.

[0157] Silicon wafer cleaning: Silicon wafers with a silicon dioxide oxide layer (oxide layer thickness 300nm, capacitance measured 11nF / cm²) are cleaned with hydrogen peroxide and concentrated sulfuric acid (heated in an electric furnace and boiled) in a volume ratio of approximately 1:2 before use. Then, they are ultrasonically cleaned sequentially with deionized water, anhydrous ethanol, and acetone for approximately 10 minutes each, and finally rapidly dried with nitrogen. An octadecyltrichlorosilane (OTS) monolayer is then prepared on the SiO2 insulating layer using a vapor phase method as an insulating modification layer.

[0158] Device fabrication: A silicon wafer with one side modified with OTS was cleaned and coated with a 10 mg / mL chloroform solution of acenaphthene dimer derivative B1 at room temperature to obtain a uniform thin film. An organic single-crystal field-effect device was then fabricated using a gold-plated film method (as the source and drain). The test results are shown in Table 1.

[0159] Under a nitrogen atmosphere, the performance transfer curves of the test device for the acenaphthene dimer derivative B1 are shown below. Figure 4 As shown, this indicates that the compound exhibits good bipolar properties, with a maximum film hole mobility of 1.70 × 10⁻⁶. -4 cm 2 V -1 s -1 The electron mobility is 4.46 × 10⁻⁶. -7 cm 2 V -1 s -1 The switch ratio is 10. 2 -10 3 The threshold voltage is -10 to 0V.

[0160] The performance data for test cases B1 to B5 are shown in Table 1.

[0161] Table 1

[0162]

[0163] As can be seen from the data in Table 1, the acenaphthene dimer derivative provided by this invention has suitable hole and electron mobility, indicating that the compound has both hole transport and electron transport properties and good bipolar performance. The fluorescence efficiency (PLQY) of the dichloromethane solution of B1 is 47.8%, indicating that the compound has good luminescent properties and has important application value in field-effect transistors.

[0164] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A acenaphthene dimer derivative, characterized in that, The acenaphthene dimer derivative has the structure shown in formula (1). Equation (1), Wherein, R is selected from hydrogen, halogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, alkoxy or alkylthio; The alkyl group in "substituted or unsubstituted alkyl" is a C1-C15 alkyl group; The substituents in the substituted alkyl group are halogen atoms; The aryl group in the "substituted or unsubstituted aryl" is a C6-C30 aryl group, and the substituent in the substituted aryl group is a C1-C20 alkyl or halogen atom; The alkylthio group has 1-20 carbon atoms; The number of carbon atoms in an alkoxy group ranges from 1 to 20. R3, R4, R5, and R6 are hydrogen.

2. The acenaphthene dimer derivative according to claim 1, wherein, The alkyl group in "substituted or unsubstituted alkyl" is a straight-chain alkyl group or a branched alkyl group.

3. The acenaphthene dimer derivative according to claim 1, wherein, R is selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, alkoxy or alkylthio.

4. The acenaphthene dimer derivative according to claim 3, wherein, R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, n-nonyl, phenyl, fluorophenyl, bromophenyl, chlorophenyl, o-tolyl, p-tolyl, m-tolyl, o-ethylphenyl, p-ethylphenyl, m-ethylphenyl, o-isopropylphenyl, p-isopropylphenyl, m-isopropylphenyl, 1-naphthyl, 2-naphthyl, methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, nonylthio, decylthio, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octyloxy, nonoxy, or decoxy.

5. A method for preparing a acenaphthene dimer derivative as described in any one of claims 1-4, the method comprising: Anenazone derivatives, cyaniding reagents, solvents, and optional copper-containing accelerators are mixed and then reacted, the reactions including cyanidation and Ullman reactions; The acenaphthene derivative has the structure shown in formula (2); Equation (2), R1 and R2 are each independently selected from halogen atoms.

6. The preparation method according to claim 5, wherein, The cyaniding agent is selected from at least one of cuprous cyanide, zinc cyanide, and potassium ferrocyanide.

7. The preparation method according to claim 5, wherein, The amount of the cyaniding agent used is 8-100 equivalents relative to 1 equivalent of the acenaphthene derivative.

8. The preparation method according to claim 5, wherein, The copper-containing accelerator is a monovalent copper compound.

9. The preparation method according to claim 8, wherein, The copper-containing accelerator is at least one of cuprous cyanide, cuprous chloride, cuprous bromide, and cuprous iodide.

10. The preparation method according to claim 5, wherein, The amount of the copper-containing accelerator is 8-100 equivalents relative to 1 equivalent of the acenaphthene derivative.

11. The preparation method according to claim 5, wherein, The reaction temperature is 100-300℃.

12. The preparation method according to claim 11, wherein, The reaction temperature is 150-220℃.

13. The preparation method according to claim 5, wherein, The reaction time is 12-48 hours.

14. The preparation method according to claim 5, wherein, The reaction was carried out under a protective atmosphere.

15. The preparation method according to claim 14, wherein, The protective atmosphere is provided by at least one of nitrogen, argon and neon.

16. The preparation method according to claim 5, wherein, The reaction was carried out under stirring conditions.

17. The preparation method according to any one of claims 5-16, wherein, The preparation method of the acenaphthene derivative includes: S1. The acenaphthene nucleus is subjected to a Friedel-Crafts acylation reaction; S2. The product obtained in step S1 is subjected to halogenation, anhydrideation and amidation reactions. The acenaphthene nucleus has the structure shown in formula (3). Equation (3).

18. The preparation method according to claim 17, wherein, Step S2 includes: S2-1. Contact the product obtained in step S1 with a halogenating reagent to carry out a halogenation reaction; S2-2, The product of the halogenation reaction is brought into contact with an acid to carry out anhydride reaction; S2-3. The product of the anhydride reaction is contacted with an amine compound to carry out an amidation reaction; The general formula of the amine compounds is R-NH2.

19. The preparation method according to claim 18, wherein, The halogenation reaction is a bromination reaction, and the conditions for the bromination reaction include: a reaction temperature of 70-100℃ and a reaction time of 1-10h.

20. The preparation method according to claim 18, wherein, The halogenating agent is selected from at least one of N-bromosuccinimide, liquid bromine, 1,3-dibromo-5,5-dimethylhydantoin, dibromoisocyanuric acid, and 1,3,5-tribromo-1,3,5-triazine-2,4,6-trione.

21. The preparation method according to claim 18, wherein, The amount of halogenating agent used is 1-10 equivalents relative to 1 equivalent of the product obtained in step S1.

22. The preparation method according to claim 18, wherein, The preparation method also includes introducing an oxidizing agent in step S2-1.

23. The preparation method according to claim 22, wherein, The oxidizing agent is at least one of benzoyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, tert-butanol peroxide, and tert-butyl ester.

24. The preparation method according to claim 22, wherein, The amount of oxidizing agent used is 0.01-1 equivalent relative to 1 equivalent of the product obtained in step S1.

25. The preparation method according to claim 18, wherein, The halogenation reaction is carried out in the presence of the first solvent.

26. The preparation method according to claim 18, wherein, The conditions for the anhydride reaction include: a reaction temperature of 60-100℃ and a reaction time of 4-10h.

27. The preparation method according to claim 18, wherein, The acid is selected from inorganic acids and / or organic acids.

28. The preparation method according to claim 27, wherein, The acid is selected from at least one of hydrochloric acid, hydrobromic acid, sulfuric acid, and acetic acid.

29. The preparation method according to claim 18, wherein, The amount of acid used is 12-100 equivalents relative to the product of the halogenation reaction described in 1 equivalent.

30. The preparation method according to claim 18, wherein, The acid is provided by an aqueous solution of the acid, the concentration of which is 36-98 wt%.

31. The preparation method according to claim 18, wherein, The anhydride reaction was carried out under stirring conditions.

32. The preparation method according to claim 18, wherein, The conditions for the amidation reaction include: a reaction temperature of 80-150℃ and a reaction time of 36-60h.

33. The preparation method according to claim 32, wherein, The conditions for the amidation reaction include: first, a low-temperature reaction at 80-100℃ for 12-24 hours, and then a high-temperature reaction at 110-140℃ for 12-48 hours.

34. The preparation method according to claim 18, wherein, The amidation reaction was carried out under a protective atmosphere.

35. The preparation method according to claim 34, wherein, The protective atmosphere is provided by at least one of nitrogen, argon and neon.

36. The preparation method according to claim 25, wherein, The amidation reaction is carried out in the presence of a second solvent.

37. The preparation method according to claim 18, wherein, The amount of the amine compound used is 1-3 equivalents relative to 1 equivalent of the product of the anhydride reaction.

38. The acenaphthene dimer derivative prepared by the preparation method according to any one of claims 5-37.

39. The use of the acenaphthene dimer derivative according to any one of claims 1-4 or 38 in a field-effect transistor.

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