A nitrogen-containing heteroimide derivative and its synthesis method and application

Abstract

The present invention discloses a nitrogen-containing heteroimide derivative, its synthesis method, and application. The nitrogen-containing heteroimide derivative of the present invention has a general structural formula as shown in Formula I, has a regular planar structural skeleton, a suitable molecular frontier orbital, a LUMO energy level between -3.0eV and -3.6eV, and a HOMO energy level between -5.8eV and -5.2eV, and has controllable photoelectric properties. When used in thin-film organic field-effect transistors, it exhibits n-type semiconductor properties with an electron mobility as high as 10 ‑3 cm 2 V ‑1 s ‑1 , has good application prospects and high application value.

Description

Technical Field

[0001] The present invention belongs to the field of organic photoelectric semiconductor materials, and in particular relates to a nitrogen-containing heteroimide derivative and a synthesis method and application thereof. Background Art

[0002] Organic field-effect transistors (OFETs) are field-effect transistors (FETs) constructed using organic semiconductors. Their active layer typically consists of a π-electron conjugated system containing aromatic rings. Over the past two decades, their advantages, such as light weight, low cost, flexibility, and suitability for large-scale fabrication, have led to significant application prospects in a wide range of fields, including organic sensors, organic memory devices, flexible flat-panel displays, electronic paper, and radio frequency identification (RFID). Therefore, the development of high-performance, multifunctional organic conjugated molecular materials is of great significance. To date, researchers have synthesized a large number of conjugated molecular materials. Among them, conjugated molecules containing amides and imides have garnered the most attention. This is because the introduction of imide groups into the conjugated backbone not only lowers the LUMO energy level of the molecule but also modulates intermolecular interactions by varying the substituents on the nitrogen atom, contributing to the development of high-performance organic semiconductor materials. Consequently, the development of novel imide conjugated backbones has become a hot topic in optoelectronic materials research. Summary of the Invention

[0003] The purpose of the present invention is to provide a nitrogen-containing heteroimide derivative and its synthesis method and application. The compound has a six-membered ring imide as the core, is a material with both luminescence and transmission properties, and has good optoelectronic device performance.

[0004] In the first aspect, the present invention protects a nitrogen-containing heteroimide derivative, the general structural formula of which is shown in Formula I:

[0005]

[0006] In formula I, Ar1 and Ar2 each independently represent an aromatic hydrocarbon group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 4 to 20 carbon atoms;

[0007] R1 and R2 are each independently selected from one or more of a hydrogen atom, a fluorine atom substituted or unsubstituted alkyl group having 1 to 37 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms, and a substituted or unsubstituted aromatic heterocyclic group having 5 to 20 carbon atoms;

[0008] Heteroatoms X1 and X2 each independently represent an oxygen or sulfur atom;

[0009] L1 and L2 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, N(R 3 )2、O(R 3)、S(R 3 )、C(=O)(R 3 )、P(=O)(R 3 )、Si(R 3 )3. a substituted or unsubstituted alkyl group having 1 to 37 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 37 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 37 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or an aromatic heterocyclic group having 4 to 20 carbon atoms;

[0010] R3 is one or more selected from hydrogen, fluorine-substituted or unsubstituted alkyl groups having 1 to 37 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 20 carbon atoms, and substituted or unsubstituted aromatic heterocyclic groups having 5 to 20 carbon atoms.

[0011] Preferably, the compound represented by formula I is any one of the compounds represented by formula I-a to formula I-e below:

[0012]

[0013] In formulas Ⅰ-a to Ⅰ-e, R1, R2, L1, and L2 are defined the same as in formula I.

[0014] More preferably, R1 and R2 each independently represent an alkyl group having 1 to 6 carbon atoms; and L1 and L2 each independently represent hydrogen.

[0015] In a specific embodiment of the present invention, the compound represented by formula I is a compound represented by formula I-b1,

[0016]

[0017] In a second aspect, the present invention provides a method for preparing a compound of formula I, comprising the following steps: condensing a compound of formula II with an amine derivative to obtain a compound of formula I;

[0018]

[0019]

[0020] In formula II, Ar1, Ar2, L1, L2, X1 and X2 are as defined in formula I;

[0021] The amine derivative is R1-NH2 or R2-NH2, where R1 and R2 are defined as in formula I.

[0022] In the above preparation method, the molar ratio of the compound represented by formula II to the amine derivative can be 1:3 to 15, preferably 1:10;

[0023] The condensation reaction temperature may be 160-180°C, preferably 160-170°C, such as 160°C;

[0024] The condensation reaction is carried out under the protection of an inert gas, and the inert gas is preferably argon or nitrogen;

[0025] The condensation reaction is carried out in an organic solvent, which may be anhydrous chlorobenzene, dichlorobenzene or xylene, preferably dichlorobenzene;

[0026] The condensation reaction time may be 16 to 24 hours, preferably 18 to 20 hours, such as 18 hours.

[0027] In the third aspect, the present invention protects the intermediate represented by formula II,

[0028]

[0029] In formula II, Ar1, Ar2, L1, L2, X1 and X2 are defined the same as in formula I.

[0030] In a fourth aspect, the method for preparing the intermediate represented by protected formula II of the present invention comprises the following steps:

[0031] 1) In the presence of a palladium catalyst, a ligand, and a base, the compound represented by Formula III, the compound represented by Formula IV, and the compound represented by Formula V undergo a coupling reaction in an organic solvent to obtain a compound represented by Formula VI;

[0032]

[0033] In formula III, formula V and formula VI, Ar1, Ar2, L1 and L2 are as defined in formula I;

[0034] 2) In the presence of a palladium catalyst, the compound represented by Formula VI undergoes an intramolecular ring-closure reaction in an organic solvent to obtain a compound represented by Formula VII;

[0035]

[0036] In formula VII, Ar1, Ar2, L1 and L2 are as defined in formula I;

[0037] 3) Under the action of a base, the compound represented by formula VII undergoes a hydrolysis reaction in a solvent to obtain a compound represented by formula VIII;

[0038]

[0039] In formula VIII, Ar1, Ar2, L1 and L2 are as defined in formula I;

[0040] 4) Acylation reaction of the compound represented by formula VIII with an acylating agent in an organic solvent to obtain the compound represented by formula II;

[0041] The acylating agent is at least one of thionyl chloride and oxalyl chloride.

[0042] Furthermore, in step 1), the molar ratio of the compound represented by formula III, the compound represented by formula IV and the compound represented by formula V is 1:2:1;

[0043] The palladium catalyst may be at least one of palladium acetate, palladium chloride, tris(dibenzylideneacetone)dipalladium, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, and bis(dibenzylideneacetone)palladium;

[0044] The molar ratio of the palladium catalyst to the compound represented by formula IV is 3% to 10%:1, preferably 5%:1 or 10%:1;

[0045] The ligand may be at least one of tris(4-methoxyphenyl)phosphine, 2-(di-tert-butylphosphino)biphenyl, phenyldicyclohexylphosphine, tris(o-methoxyphenyl)phosphine, 1,1'-bis(diphenylphosphino)ferrocene, rac-2-(di-tert-butylphosphino)-1,1'-binaphthyl, 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, triphenylphosphine, and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;

[0046] The molar ratio of the ligand to the compound represented by formula IV is 8% to 20%:1, preferably 12%:1 or 10%:1;

[0047] The base may be at least one of potassium carbonate, sodium carbonate, cesium carbonate, potassium tert-butoxide, sodium tert-butoxide, sodium hydrogen, sodium hydroxide, and potassium hydroxide;

[0048] The molar ratio of the base to the compound represented by formula IV is 2 to 5:1, preferably 3:1 or 2:1;

[0049] The organic solvent may be at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, dichlorobenzene and ethyl acetate;

[0050] The temperature of the coupling reaction may be 80-130°C, preferably 120°C;

[0051] The coupling reaction is carried out under the protection of an inert gas, preferably argon or nitrogen;

[0052] The coupling reaction time is 16 to 48 hours, preferably 36 hours or 24 hours;

[0053] In step 2), the palladium catalyst is at least one of palladium acetate, palladium chloride, tris(dibenzylideneacetone)dipalladium, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, and bis(dibenzylideneacetone)palladium;

[0054] The molar ratio of the palladium catalyst to the compound represented by formula VI is 1 to 3:1, preferably 2:1 or 1:1;

[0055] The organic solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, dichlorobenzene and acetic acid;

[0056] The intramolecular ring-closure reaction is carried out under the protection of an inert gas, and the inert gas is preferably argon or nitrogen;

[0057] The temperature of the intramolecular ring-closure reaction is 80-130°C, preferably 120°C or 100°C;

[0058] The time of the intramolecular ring-closure reaction is 6 to 18 hours, preferably 6 to 10 hours, such as 6 hours;

[0059] In step 3), the base is at least one of potassium carbonate, sodium carbonate, cesium carbonate, potassium tert-butoxide, sodium tert-butoxide, sodium hydrogen hydride, sodium hydroxide and potassium hydroxide;

[0060] The molar ratio of the base to the compound represented by formula VII is 5 to 30:1, preferably 10:1;

[0061] The solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, dichlorobenzene, ethyl acetate, water, methanol and ethanol;

[0062] The temperature of the hydrolysis reaction is 60-110°C, preferably 90°C or 80°C;

[0063] The hydrolysis reaction time is 18 to 28 hours, preferably 24 hours;

[0064] In step 4), the molar ratio of the compound represented by formula VIII to the acylating agent is 1:2 to 4, preferably 1:3;

[0065] The organic solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, and dichloromethane;

[0066] The temperature of the acylation reaction is 60-110°C, preferably 90°C;

[0067] The acylation reaction time is 18 to 28 hours, preferably 24 hours.

[0068] In a fifth aspect, the present invention protects the use of the compound represented by formula I described in any one of the above items in the preparation of organic solar cells, organic field-effect transistors, organic light-emitting transistors, organic light-emitting diodes or organic semiconductor materials.

[0069] In a sixth aspect, the present invention protects a field effect device, which is made of a thin film or single crystal device made of the compound represented by formula I described in any one of the above items, or uses the compound represented by formula I described in any one of the above items as an n-type or p-type semiconductor material.

[0070] In a seventh aspect, the present invention protects an organic light-emitting diode device, which uses the compound represented by formula I described in any one of the above items as a light-emitting layer material, a host material or a transport layer material.

[0071] The present invention has the following beneficial effects:

[0072] The nitrogen-containing heteroimide derivatives provided by the present invention have a regular planar structural skeleton, a suitable molecular frontier orbital, a LUMO energy level between -3.0eV and -3.6eV, a HOMO energy level between -5.8eV and -5.2eV, and controllable photoelectric properties; when applied to thin-film organic field-effect transistors, they exhibit n-type semiconductor properties, with an electron mobility as high as 10 -3 cm 2 V -1 s -1 , has good application prospects and high application value. BRIEF DESCRIPTION OF THE DRAWINGS

[0073] Figure 1 This is a route for synthesizing the compound represented by formula I-b1 in Example 1.

[0074] Figure 2 The crystal structure and stacking diagram of the compound represented by formula I-b1 synthesized in Example 1.

[0075] Figure 3 These are the UV-visible absorption spectrum (Abs@CF) and emission spectrum (PL@CF) of the compound represented by Formula I-b1 synthesized in Example 1 in chloroform solution, the emission spectrum (PL@Film) of the compound represented by Formula I-b1 in thin film (PL@Film) and solid (PL@Solid), and the CIE color coordinates of the maximum emission of the solid and solution.

[0076] Figure 4 This is the cyclic voltammetric characteristic curve of the compound represented by formula I-b1 synthesized in Example 1 in ultra-dry acetonitrile solution.

[0077] Figure 5 This is the output curve of the field effect device made with the compound represented by formula I-b1 synthesized in Example 1. DETAILED DESCRIPTION

[0078] The present invention will be further described in detail below in conjunction with specific embodiments. The examples provided are only for illustrating the present invention and are not intended to limit the scope of the present invention. The examples provided below can serve as a guide for further improvements by those skilled in the art and are not intended to limit the present invention in any way.

[0079] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; the materials, reagents, etc. used are all available from commercial sources unless otherwise specified.

[0080] Example 1: Synthesis of nitrogen-containing heteroimide derivatives (compounds represented by formula I-b1)

[0081] according to Figure 1 The compound represented by formula I-b1 is synthesized by the synthetic route shown in the figure. The specific steps are as follows:

[0082] (1) Preparation of the compound represented by formula VI-b1

[0083] To a 500 mL single-necked flask, aniline (9.9 g, 105 mmol), diethyl 2,5-dibromoterephthalate (10.0 g, 26.5 mmol), palladium acetate (0.59 g, 2.65 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.53 g, 2.65 mmol), cesium carbonate (17 g, 52.3 mmol), and 250 mL of freshly distilled toluene were added sequentially. The mixture was stirred magnetically under nitrogen and refluxed for 24 hours. After cooling to room temperature, 200 mL of solvent was removed by vacuum distillation. 200 mL of methanol, 100 mL of ethyl acetate, and 50 mL of water were added. The mixture was stirred at room temperature for 1 hour, filtered, and the residue collected. The solid was washed sequentially with water, ethyl acetate, and methanol, and dried under vacuum to obtain 8.1 g of a dark red solid powder (yield: 76%). 1 HNMR(400MHz,DMSO-d6)δ8.55(s,1H),7.82(s,1H),7.30(t,J=7.7Hz,2H),7.11(d, J=7.8Hz,2H),6.95(t,J=7.2Hz,1H),4.25(q,J=6.9Hz,2H),1.22(t,J=7.0Hz,3H); 13 C NMR (101 MHz, DMSO-d6) δ 166.89, 142.87, 137.33, 129.86, 121.91, 121.44, 120.21, 119.05, 61.65, 14.36.; HR-MS: calculated for C 24 H 24 N2O4(M + ): 404.1736, calculated value: 404.1730.

[0084] (2) Preparation of the compound represented by formula VII-b1

[0085] In a 100 mL single-necked flask, compound VI-b1 (1 g, 2.5 mmol), palladium acetate (1.2 g, 2.65 mmol), and 50 mL of acetic acid were added sequentially. The mixture was stirred magnetically and reacted at 100°C for 6 h. After cooling to room temperature, 200 mL of chloroform and 50 mL of water were added, and extraction and separation were performed. The organic layer was collected and the solvent was removed by distillation under reduced pressure. The mixture was isolated and purified by column chromatography to obtain 0.68 g of a yellow solid powder (yield: 68%). 1 H NMR (400MHz, DMSO-d6) δ11.27(s,1H),8.45(d,J=8.2Hz,1H),7.72(d,J=8.2Hz,1H),7.4 9(t,J=7.7Hz,1H),7.20(t,J=7.7Hz,1H),4.72(q,J=7.2Hz,2H),1.51(t,J=7.1Hz,3H). 13 C NMR (101 MHz, DMSO-d6) δ 167.27, 142.27, 134.72, 127.35, 124.20, 120.87, 120.65, 119.07, 112.10, 110.27, 62.11, 14.71.; HR-MS: calculated for C 24 H 20 N2O4(M + ): 400.1423, calculated value: 400.1417.

[0086] (3) Preparation of the compound represented by formula VIII-b1

[0087] To a 100 mL single-necked flask, compound VII-b1 (1 g, 2.5 mmol), potassium hydroxide (1.4 g, 25 mmol), 10 mL of water, and 50 mL of tetrahydrofuran were added sequentially. The mixture was stirred magnetically and reacted at 80°C for 24 h. After cooling to room temperature, the solvent was removed by distillation under reduced pressure. 3N hydrochloric acid was added to adjust the pH to 2-3. The solid was collected by filtration to obtain 0.83 g of a brownish-red solid powder (yield: 97%). 1 H NMR(400MHz,DMSO-d6)δ13.98(s,1H),11.24(s,1H),8.72–8.60(m,1H),7.75(dt,J=8 .2,1.0Hz,1H),7.45(ddd,J=8.2,7.0,1.2Hz,1H),7.17(ddd,J=8.1,7.0,1.1Hz,1H). 13C NMR (101 MHz, DMSO-d6) δ 167.86, 141.21, 134.12, 125.96, 123.68, 120.03, 119.76, 117.70, 111.02, 109.84, 65.74.; HR-MS: calculated for C 20 H 12 N2O4(M + ): 344.0797, calculated value: 343.0722.

[0088] (4) Preparation of the compound represented by formula II-b1

[0089] In a 100 mL single-necked flask, compound VIII-b1 (1 g, 2.9 mmol), oxalyl chloride (1.1 g, 8.6 mmol), and 30 mL of anhydrous dichloromethane were added sequentially. The mixture was stirred magnetically and reacted at 90°C for 24 h. The solvent was removed by distillation under reduced pressure and the product was used directly in the next step without further treatment.

[0090] (5) Preparation of the compound represented by formula I-b1

[0091] In a 100 mL single-necked flask, compound II-b1 (1 g, 2.9 mmol), n-hexylamine (2.9 g, 29 mmol), and 50 mL of o-dichlorobenzene were added sequentially. The mixture was stirred magnetically and reacted at 160°C under nitrogen for 18 h. After cooling to room temperature, the solvent was removed by distillation under reduced pressure. The mixture was isolated and purified by column chromatography to obtain 0.13 g of a yellow-green solid powder (yield: 10%). 1 H NMR(700MHz,Tetrachloroethane-d2)δ9.40(d,J=8.0Hz,2H),8.56(d,J=8.2Hz,2H),7.59(t,J=7.7Hz,2H),7.47(t,J= 7.6Hz,2H),4.20(t,J=7.4Hz,4H),1.82–1.71(m,4H),1.40(t,J=7.6Hz,4H),1.30–1.26(m,9H),0.80(t,J=7.2Hz,6H); 13 C NMR (176 MHz, Tetrachloroethane-d2) δ 161.10, 147.46, 139.66, 135.43, 130.18, 127.83, 125.26, 124.24, 122.08, 115.58, 111.67, 42.16, 31.49, 28.03, 26.70, 22.48, 13.86. HR-MS: calculated for C 34 H 34 N4O4(M +):562.2580,calculated value:562.2574;Elemental analysis:calculated value:C 34 H 34 N4O4: C, 72.58; H, 6.09; N, 9.96. Actual measured values: C, 72.58; H, 6.05; N, 9.94. From the above, we can see that the product structure is correct.

[0092] Example 2: Crystal structure and packing

[0093] Preparation of crystals: The compound represented by formula I-b1 is dissolved in chloroform solution and slowly diffused into the chloroform solution by the diffusion method to obtain the crystal structure and stacking. Figure 2 As shown, the nitrogen-containing six-membered ring diimide has good planarity, which is conducive to charge transport. The molecules show strong π-π interactions and are arranged in a columnar shape, where the π-π distance is The distance between CH···O=C is

[0094] Example 3, UV-visible absorption spectrum and fluorescence emission spectrum

[0095] The target compound represented by formula I-b1 in Example 1 was dissolved in chloroform solution at a concentration of 10 -5 mol / L, and the UV-visible absorption spectrum and emission spectrum of the solution were measured. At the same time, the emission spectrum of the target compound represented by formula I-b1 in solid and film form was also measured. Figure 3 The target compound represented by Formula I-b1 exhibits maximum emission wavelengths of 458, 512, and 514 nm in chloroform solution, thin film, and solid form, respectively. The maximum emission wavelength of the solid form is green with a half-peak width of 29 nm, which is 54 nm red-shifted relative to the blue emission of the solution. The CIE color coordinates of the maximum emission of the solid and solution are (0.23, 0.64) and (0.12, 0.18), respectively. Both the solid and solution forms exhibit high quantum yields of 10% and 40%, respectively.

[0096] Example 4: Measurement of frontier orbital energy levels (LUMO) using cyclic voltammetry

[0097] The electrochemical properties of the target compound represented by Formula I-b1 in Example 1 of the present invention were tested using an electrochemical workstation. A three-electrode test system was used, with a glassy carbon electrode as the working electrode, an Ag / AgCl electrode as the reference electrode, and a platinum wire electrode as the counter electrode. The cyclic voltammetry curve of the target compound I-b1 in Example 1 in ultra-dry acetonitrile solution was tested at a scan rate of 100 mv / s using tetrabutylammonium hexafluorophosphate as the supporting electrolyte and ferrocene as the internal standard. Figure 4 As shown. Figure 4 It can be seen that the maximum reduction peak potential of the compound represented by formula I-b1 is at -1.31 V. According to the formula LUMO=-[E red -E(Fc / Fc + )+4.8]eV, and its LUMO energy level is calculated to be -3.01V.

[0098] Example 5: Preparation of Field Effect Device

[0099] According to the method described in the literature (Chem. Rev. 2012, 112, 2208-2267), a 300 nm thick layer of silicon dioxide was deposited on a single crystal silicon wafer, and then gold was plated using photolithography. The wafers were 1440 μm wide and 5, 10, 20, 30, 40, and 50 μm long. The wafers were first modified with a monolayer of octadecyltrichlorosilane and then with p-methylthiophenol. The compound represented by Formula I-b1, prepared in Example 1 of the present invention, was then evaporated onto the modified wafer. The substrate temperature during evaporation was controlled at 80°C to prepare a field-effect device of the compound, and its field-effect properties were tested; the corresponding output curve is shown in FIG. Figure 5 As shown. In nitrogen atmosphere, the compounds all exhibit n-type semiconductor properties, with a maximum electron mobility of 10 -3 cm 2 V -1 s -1 .

[0100] The present invention has been described in detail above. It will be apparent to those skilled in the art that the present invention can be practiced over a wide range of parameters, concentrations, and conditions without departing from the spirit and scope of the present invention and without unnecessary experimentation. Although specific embodiments have been described herein, it should be understood that further modifications may be made to the present invention. In short, according to the principles of the present invention, this application is intended to cover any variations, uses, or improvements to the present invention, including those made using conventional techniques known in the art that depart from the scope disclosed herein. Applications of the essential features may be made within the scope of the appended claims.

Claims

1. The compound represented by formula I, In formula I, Ar1 and Ar2 each independently represent a phenyl group; R1 and R2 are each independently selected from an alkyl group having 1 to 6 carbon atoms; Heteroatoms X1 and X2 each independently represent an oxygen or sulfur atom; L1 and L2 are each independently selected from hydrogen.

2. A method for preparing the compound of claim 1, comprising the steps of: condensing the compound of formula II with an amine derivative to obtain the compound of formula I; In formula II, Ar1, Ar2, L1, L2, X1 and X2 are as defined in formula I; The amine derivative is R1-NH2 or R2-NH2, where R1 and R2 are defined as in formula I.

3. The preparation method according to claim 2, wherein: The molar ratio of the compound represented by formula II to the amine derivative is 1:3-15; The condensation reaction temperature is 160-180°C; The condensation reaction is carried out under the protection of an inert gas; The condensation reaction is carried out in an organic solvent, and the organic solvent is anhydrous chlorobenzene, dichlorobenzene or xylene; The condensation reaction time is 16 to 24 hours.

4. The intermediate represented by formula II, In formula II, Ar1, Ar2, L1, L2, X1 and X2 are defined the same as those for the compound of formula I in claim 1.

5. The method for preparing the intermediate represented by formula II according to claim 4, comprising the following steps: 1) In the presence of a palladium catalyst, a ligand, and a base, the compound represented by Formula III, the compound represented by Formula IV, and the compound represented by Formula V undergo a coupling reaction in an organic solvent to obtain a compound represented by Formula VI; In formula III, formula V and formula VI, Ar1, Ar2, L1 and L2 are as defined in formula I; 2) In the presence of a palladium catalyst, the compound represented by Formula VI undergoes an intramolecular ring-closure reaction in an organic solvent to obtain a compound represented by Formula VII; In formula VII, Ar1, Ar2, L1 and L2 are as defined in formula I; 3) Under the action of a base, the compound represented by formula VII undergoes a hydrolysis reaction in a solvent to obtain a compound represented by formula VIII; In formula VIII, Ar 1 , Ar 2 , L 1 and L 2 are the same as those in formula I; 4) Acylation reaction of the compound represented by formula VIII with an acylating agent in an organic solvent to obtain the compound represented by formula II; The acylating agent is at least one of thionyl chloride and oxalyl chloride.

6. The method according to claim 5, characterized in that: In step 1), the molar ratio of the compound represented by formula III, the compound represented by formula IV and the compound represented by formula V is 1:2:1; The palladium catalyst is at least one of palladium acetate, palladium chloride, tris(dibenzylideneacetone)dipalladium, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, and bis(dibenzylideneacetone)palladium; The molar ratio of the palladium catalyst to the compound represented by formula IV is 3% to 10%:1; The ligand is at least one of tris(4-methoxyphenyl)phosphine, 2-(di-tert-butylphosphino)biphenyl, phenyldicyclohexylphosphine, tris(o-methoxyphenyl)phosphine, 1,1'-bis(diphenylphosphino)ferrocene, rac-2-(di-tert-butylphosphino)-1,1'-binaphthyl, 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl, triphenylphosphine, and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; The molar ratio of the ligand to the compound represented by formula IV is 8% to 20%:1; The base is at least one of potassium carbonate, sodium carbonate, cesium carbonate, potassium tert-butoxide, sodium tert-butoxide, sodium hydrogen, sodium hydroxide, and potassium hydroxide; The molar ratio of the base to the compound represented by formula IV is 2 to 5:1; The organic solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, dichlorobenzene and ethyl acetate; The temperature of the coupling reaction is 80-130°C; The coupling reaction is carried out under the protection of inert gas; The coupling reaction time is 16 to 48 hours; In step 2), the palladium catalyst is at least one of palladium acetate, palladium chloride, tris(dibenzylideneacetone)dipalladium, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, and bis(dibenzylideneacetone)palladium; The molar ratio of the palladium catalyst to the compound represented by formula VI is 1 to 3:1; The organic solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, dichlorobenzene and acetic acid; The intramolecular ring-closure reaction is carried out under the protection of an inert gas; The temperature of the intramolecular ring-closure reaction is 80 to 130° C. The time of the intramolecular ring-closure reaction is 6 to 18 hours; In step 3), the base is at least one of potassium carbonate, sodium carbonate, cesium carbonate, potassium tert-butoxide, sodium tert-butoxide, sodium hydrogen hydride, sodium hydroxide and potassium hydroxide; In step 3), the solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, dichlorobenzene, ethyl acetate, water, methanol, and ethanol; The molar ratio of the base to the compound represented by formula VII is 5 to 30:1; The temperature of the hydrolysis reaction is 60-110°C; The hydrolysis reaction time is 18 to 28 hours; In step 4), the molar ratio of the compound represented by formula VIII to the acylating agent is 1:2-4; The organic solvent is at least one of toluene, chlorobenzene, tetrahydrofuran, dioxane, and dichloromethane; The temperature of the acylation reaction is 60-110°C; The acylation reaction time is 18 to 28 hours.

7. Use of the compound of formula I according to claim 1 in the preparation of organic field-effect transistors.

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