U-shaped conjugated fused material containing thiophene derivative as well as preparation method and application of U-shaped conjugated fused material

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a thiophene derivative-containing U-shaped conjugated fused material as well as a preparation method and application thereof. The structure of the material is shown as a formula 1), a formula 2), a formula 3), a formula 4) or a formula 5), R1 group is C1-C30 alkane, phenyl, C1-C30 alkyl or alkoxy substituted phenyl, and thiophene and derivative structures thereof can play a role in adjusting the topological structure, absorption spectrum and fluorescence spectrum of the U-shaped conjugated fused material. The preparation method has the advantages of simple raw material structure, low cost, easiness in obtaining, easiness in purification, low cost, easiness in preparation and the like. In addition, due to the isomerism characteristics of the U-shaped conjugated fused material, the U-shaped conjugated fused material has a unique electronic structure and a cavity structure and is an excellent organic photoelectric material. The carrier mobility of the thin film organic field effect transistor using E3 as the organic semiconductor layer is further tested to be 0.1 cm < 2 > V <-1 > s <-1 >. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a U-shaped conjugated fused material containing thiophene derivatives, and a preparation method and application thereof. Background Art

[0002] As one of the most widely used active devices in microelectronics, the field effect transistor has become a strong competitor to the bipolar transistor and one of the important components in the microelectronics industry due to its advantages such as low input power consumption, low noise, wide safe working area, high impedance and no secondary breakdown. Since its birth, the materials used in its preparation have been mainly silicon, germanium and other inorganic semiconductor materials, while inorganic field effect transistors have disadvantages such as high manufacturing cost, difficulty in preparing single crystals, high temperature process, only hard materials can be used for substrates, and it is difficult to prepare large surface areas. In addition, inorganic field effect transistors have approached the natural limit of miniaturization. Compared with inorganic semiconductor materials, organic semiconductor materials have the advantages of low production cost, wide source of materials, simple process, no need for high temperature and flexible substrates.

[0003] Linear condensed small molecule organic semiconductors are an important class of organic semiconductor materials. Due to their superior electrical properties and controllable physicochemical properties, they are widely used in the field of organic electronics. The introduction of heteroatoms into the π-conjugated skeleton is considered to be an effective way to regulate the stability, molecular stacking and mobility of semiconductor materials, which provides opportunities for the development of new materials. Thiophene and its derivatives have been widely studied and researched in linear condensed small molecule organic semiconductors due to their unique electronic structure, good stability and adjustability (A Highlyπ-Stacked Organic Semiconductor for Field-Effect Transistors Based on Linearly Condensed Pentathienoacene, J.Am.Chem.Soc.2005,127,38,13281–13286), (Synthesis,Characterization,and Field-Effect Transistor Performance of Thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene Derivatives,Synthesis,Characterization,and Field-Effect Transistor Performance of Thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene Derivatives, Adv. Funct. Mater. 2009, 19, 772-778). U-type condensed small molecule organic semiconductors are an important variant of linear condensed small molecule organic semiconductors, with unique molecular structure and excellent electrical properties. Summary of the invention

[0004] The purpose of the present invention is to provide a U-shaped conjugated fused material containing thiophene derivatives, and a preparation method and application thereof. In the U-shaped conjugated fused material containing thiophene derivatives of the present invention, the fusion site of the thiophene derivatives is adjusted to change the molecular configuration and stacking mode, so that the U-shaped conjugated fused material has a unique electronic structure and cavity structure, and can be used as a class of excellent organic photoelectric materials; the material of the present invention has the advantages of cheap and easy to obtain raw materials, low cost, easy preparation, and easy purification. Further testing of the carrier mobility of its thin film organic field effect transistor is 0.1cm 2 V - 1 s -1 .

[0005] The present invention provides a U-shaped conjugated fused material containing a thiophene derivative, the general structural formula of which is shown in Formula 1), Formula 2), Formula 3), Formula 4) or Formula 5):

[0006]

[0007] In the formula, R1 is C1-C 30 Alkyl, phenyl, C1-C 30 Alkyl or C1-C 30 Alkoxy substituted phenyl.

[0008] In the present invention, R1 is C 10 -C 30 Alkyl, or any one of the chemical groups shown in Formula 6) to Formula 8):

[0009]

[0010] In the formula, R2, R3, and R4 are independently C1-C 10 Alkyl or C1-C 10 Alkoxy.

[0011] The present invention also provides a method for preparing the above-mentioned U-shaped conjugated fused material containing thiophene derivatives, comprising the following steps: firstly, compound A and compound B1, B2, B3, B4 or B5 are used as starting materials, and the corresponding products C1, C2, C3, C4 or C5 are prepared by Suzuki coupling reaction; then, compound C1, C2, C3, C4 or C5 and methyl methoxy triphenyl phosphonium chloride are subjected to Wittig reaction under the action of a base to generate products D1, D2, D3, D4 or D5; finally, compound D1, D2, D3, D4 or D5 is subjected to Friedel-Crafts reaction under the action of a catalyst to obtain a U-shaped conjugated fused material containing thiophene derivatives as shown in formula 1), formula 2), formula 3), formula 4) or formula 5), ​​and the synthesis route thereof is as follows:

[0012]

[0013]

[0014] Where R1 is C1-C 30 Alkyl, phenyl, C1-C 30 Alkyl or C1-C 30 Alkoxy substituted phenyl.

[0015] In the present invention, the Suzuki coupling reaction conditions are as follows: in a solvent, in the presence of a base, a catalyst and a ligand, compound A is subjected to a Suzuki coupling reaction with compound B1, B2, B3, B4 or B5 to obtain the corresponding compound C1, C2, C3, C4 or C5.

[0016] Preferably, the solvent is one or more of water, benzene, toluene, xylene, decahydronaphthalene, diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, 1,1-diethoxymethane, chloroform, 1,2-dichloroethane and anisole;

[0017] Preferably, the base is one or more of sodium tert-butoxide (t-BuONa), potassium tert-butoxide (t-BuOK), potassium carbonate (K2CO3), sodium carbonate (Na2CO3) and potassium phosphate (K3PO4);

[0018] Preferably, the catalyst is one or more of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), bis(dibenzylideneacetone palladium (Pd(dba)2), tris(dibenzylideneacetone)dipalladium trichloromethane (Pd2(dba)3·CHCl3), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), palladium acetate (Pd(OAc)2), palladium dichloride (PdCl2) and chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) (XPhosPd G2);

[0019] Preferably, the ligand is one or more of triphenylphosphine (PPh3), tri-tert-butylphosphine (P(t-Bu)3), tri-tert-butylphosphine tetrafluoroborate, 2,2′-bis(diphenylphosphine)-1,1′-binaphthyl (BINAP), 2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl (SPhos), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (Xphos), 1,2,3,4,5-pentylphenyl-1′-(di-tert-butylphosphine)ferrocene (Qphos), 2-dicyclohexylphosphine-2′-methylbiphenyl (MePhos), 2-(di-tert-butylphosphine)biphenyl (JohnPhos) and 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (XantPhos);

[0020] Preferably, the volume molar ratio of the solvent to the compound A is 2:1 to 50:1 mL / mmol; the molar ratio of the compound A to the compound B is 0.1:1 to 0.5:1; the reaction temperature is 25°C to 100°C, and the reaction time is 6-48h.

[0021] In the present invention, the Wittig reaction conditions are as follows: the reaction is carried out under ice bath conditions, the base is potassium tert-butoxide, the reaction solvent is tetrahydrofuran, and the reaction time is 1-3 hours.

[0022] In the present invention, the Friedel-Crafts reaction conditions are as follows: the reaction is carried out at room temperature, the catalyst is bismuth trifluoromethanesulfonate (Bi(OTf)3), the reaction solvent is 1,2-dichloroethane, and the reaction time is 1-3h.

[0023] Furthermore, the present invention also provides the use of the above-mentioned U-shaped conjugated fused material containing thiophene derivatives in organic field effect transistor devices.

[0024] Compared with the prior art, the present invention has the following beneficial effects:

[0025] 1) At present, the construction of linear condensed small molecule organic semiconductors mostly places thiophene and its derivative units in the center of the molecule. The present invention places thiophene and its derivative units on both sides of the molecule through Suzuki coupling and Wittig reaction. This construction method can fully utilize the molecular structure characteristics of thiophene and its derivatives, and can construct a series of molecules with different configurations. At the same time, it can effectively regulate the electronic structure of the molecule, change the electrochemical properties of the material, make the absorption spectrum more red-shifted, reduce the optical band gap of the material, enhance the interaction between molecules, and effectively enhance the crystallinity and intermolecular charge transfer performance of the material.

[0026] 3) The present invention is based on the strategy of introducing heteroatoms into the π-conjugated skeleton to adjust the stability, molecular stacking and mobility of semiconductor materials to design and develop new U-shaped conjugated fused materials, in order to obtain organic semiconductor materials with high mobility and high-performance OFET devices. The carrier mobility of the material E3 obtained in the present invention is 0.1cm 2 V -1 s -1 . BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 : H NMR spectrum of compound E1.

[0028] Figure 2 : Single crystal structure of compound E1.

[0029] Figure 3 : UV and fluorescence spectra of compound E1.

[0030] Figure 4 : H NMR spectrum of compound E2.

[0031] Figure 5 : Single crystal structure of compound E2.

[0032] Figure 6 : H NMR spectrum of compound E3.

[0033] Figure 7 : Single crystal structure of compound E3.

[0034] Figure 8 : H NMR spectrum of compound E4.

[0035] Fig. 9 : Single crystal structure of compound E4.

[0036] Fig.10 : H NMR spectrum of compound E5.

[0037] Fig.11 : E1 compound OFET device structure diagram. DETAILED DESCRIPTION

[0038] The present invention is further described below by way of examples, but the present invention is not limited to the scope of the examples. The experimental methods in the following examples without specifying specific conditions are carried out according to conventional methods and conditions, or selected according to the product specifications.

[0039] Example 1: Preparation of Compound E1

[0040]

[0041] (1) Compound A (150 mg, 0.23 mmol), compound B1 (100 mg, 0.48 mmol), and XPhosPd G2 (50 mg, 0.06 mmol) were weighed and dissolved in 100 mL of THF. Under nitrogen protection, 50 mL of potassium phosphate solution (0.6 M) was added and reacted at 50°C for 24 h. THF in the reaction system was removed by vacuum distillation, and the yellow product C1 (100 mg, yield 66%) was obtained by purification on a silica gel column.

[0042] (2) Weigh methyl methoxy triphenylphosphonium chloride (420 mg, 1.22 mmol) and inject into 30 mL of dry THF, place in an ice bath, inject into 1.5 mL of t-BuOK (1 Min THF) under nitrogen protection, and stir for 30 minutes. Weigh the product C1 (100 mg, 0.153 mmol) and dissolve in 20 mL of THF and inject. Then transfer the reaction system to room temperature and continue the reaction for 2 hours. After removing the solvent by reduced pressure distillation, the white product D1 (100 mg, yield 95%) can be obtained by purification on a silica gel column.

[0043] (3) Add product D1 (100 mg, 0.141 mmol) and Bi(OTf)3 (25 mg, 0.038 mmol) to the reaction flask, and after evacuation, add 30 mL of 1,2-dichloroethane and react at room temperature for 2 h. After removing the solvent by vacuum distillation, purify on a silica gel column to obtain a bright yellow solid E1 (90 mg, yield 90%).

[0044] Figure 1 is the H NMR spectrum of compound E1; Figure 2 This is the single crystal structure of compound E1. Figure 3 The UV spectrum and fluorescence spectrum of compound E1.

[0045] Example 2: Preparation of Compound E2

[0046]

[0047] (1) Compound A (160 mg, 0.25 mmol), compound B2 (110 mg, 0.53 mmol), and XPhosPd G2 (50 mg, 0.06 mmol) were weighed and dissolved in 100 mL of THF. Under nitrogen protection, 50 mL of potassium phosphate solution (0.6 M) was added and reacted at 50°C for 24 h. THF in the reaction system was removed by vacuum distillation, and the yellow product C2 (100 mg, yield 63%) was obtained by purification on a silica gel column.

[0048] (2) Weigh methyl methoxy triphenylphosphonium chloride (450 mg, 1.31 mmol) and inject into 30 mL of dry THF, place in an ice bath, inject into 1.5 mL of t-BuOK (1 M in THF) under nitrogen protection, and stir for 30 minutes. Weigh the product C1 (100 mg, 0.153 mmol) and dissolve in 20 mL of THF and inject. Then transfer the reaction system to room temperature and continue the reaction for 2 hours. After removing the solvent by reduced pressure distillation, the white product D2 (100 mg, yield 95%) can be obtained by purification on a silica gel column.

[0049] (3) Add product D1 (100 mg, 0.141 mmol) and Bi(OTf)3 (25 mg, 0.038 mmol) to the reaction flask, and after evacuation, add 30 mL of 1,2-dichloroethane and react at room temperature for 2 h. After removing the solvent by vacuum distillation, purify on a silica gel column to obtain a bright yellow solid E2 (90 mg, yield 90%).

[0050] The H NMR spectrum of compound E2 is as follows Figure 4 The single crystal structure of compound E2 is shown in Figure 5 shown.

[0051] Example 3: Preparation of Compound E3

[0052]

[0053] (1) Compound A (160 mg, 0.21 mmol), compound B3 (110 mg, 0.41 mmol), and XPhosPd G2 (50 mg, 0.06 mmol) were weighed and dissolved in 100 mL of THF. Under nitrogen protection, 50 mL of potassium phosphate solution (0.6 M) was added and reacted at 50°C for 24 h. THF in the reaction system was removed by vacuum distillation, and the yellow product C3 (100 mg, yield 60%) was obtained by purification on a silica gel column.

[0054] (2) Weigh methyl methoxy triphenylphosphonium chloride (450 mg, 1.31 mmol) and inject into 30 mL of dry THF, place in an ice bath, inject into 1.5 mL of t-BuOK (1 M in THF) under nitrogen protection, and stir for 30 minutes. Weigh the product C3 (100 mg, 0.125 mmol) and dissolve in 20 mL of THF and inject. Then transfer the reaction system to room temperature and continue the reaction for 2 hours. After removing the solvent by vacuum distillation, the white product D3 (100 mg, yield 95%) can be obtained by purification on a silica gel column.

[0055] (3) Add product D3 (100 mg, 0.111 mmol) and Bi(OTf)3 (25 mg, 0.038 mmol) to the reaction flask, and after evacuation, add 30 mL of 1,2-dichloroethane and react at room temperature for 2 h. After removing the solvent by vacuum distillation, purify on a silica gel column to obtain a dark yellow solid E3 (90 mg, yield 90%).

[0056] The H NMR spectrum of compound E3 is as follows Figure 6 As shown; the single crystal structure of compound E3 is shown Figure 7 shown.

[0057] Example 4: Preparation of Compound E4

[0058]

[0059] (1) Compound A (200 mg, 0.26 mmol), compound B4 (140 mg, 0.52 mmol), and XPhosPd G2 (50 mg, 0.06 mmol) were weighed and dissolved in 100 mL of THF. Under nitrogen protection, 50 mL of potassium phosphate solution (0.6 M) was added and reacted at 50°C for 24 h. THF in the reaction system was removed by vacuum distillation, and the yellow product C4 (140 mg, yield 66%) was obtained by purification on a silica gel column.

[0060] (2) Weigh methyl methoxy triphenylphosphonium chloride (450 mg, 1.31 mmol) and inject into 30 mL dry THF, place in an ice bath, inject into 1.5 mL t-BuOK (1 M in THF) under nitrogen protection, and stir for 30 minutes. Weigh the product C4 (140 mg, 0.172 mmol) and dissolve in 20 mL THF and inject. Then transfer the reaction system to room temperature and continue the reaction for 2 hours. After the solvent is distilled off under reduced pressure, the white product D4 (140 mg, yield 95%) can be obtained by purification on a silica gel column.

[0061] (3) Add product D4 (140 mg, 0.170 mmol) and Bi(OTf)3 (25 mg, 0.038 mmol) to the reaction flask, and after evacuation, add 30 mL of 1,2-dichloroethane and react at room temperature for 2 h. After removing the solvent by vacuum distillation, purify on a silica gel column to obtain a dark yellow solid E4 (130 mg, yield 90%).

[0062] The H NMR spectrum of compound E4 is as follows Figure 8 As shown, the single crystal structure of compound E4 is shown Fig. 9 shown.

[0063] Example 5: Preparation of Compound E5

[0064]

[0065] 1) Weigh compound A (200 mg, 0.26 mmol), compound B5 (140 mg, 0.52 mmol), and XPhosPd G2 (50 mg, 0.06 mmol), dissolve in 100 mL THF, add 50 mL potassium phosphate solution (0.6 M) under nitrogen protection, and react at 50°C for 24 h. Remove THF from the reaction system by vacuum distillation, and purify on a silica gel column to obtain a yellow product C5 (140 mg, yield 66%).

[0066] (2) Weigh methyl methoxy triphenylphosphonium chloride (450 mg, 1.31 mmol) and inject into 30 mL dry THF, place in an ice bath, inject into 1.5 mL t-BuOK (1 M in THF) under nitrogen protection, and stir for 30 minutes. Weigh the product C5 (140 mg, 0.172 mmol) and dissolve in 20 mL THF and inject. Then transfer the reaction system to room temperature and continue the reaction for 2 hours. After the solvent is distilled off under reduced pressure, the white product D5 (140 mg, yield 95%) can be obtained by purification on a silica gel column.

[0067] (3) Add product D5 (140 mg, 0.170 mmol) and Bi(OTf)3 (25 mg, 0.038 mmol) to the reaction flask, and after evacuation, add 30 mL of 1,2-dichloroethane and react at room temperature for 2 h. After removing the solvent by vacuum distillation, purify on a silica gel column to obtain a dark yellow solid E5 (130 mg, yield 90%).

[0068] Fig.10 is the H NMR spectrum of compound E5.

[0069] Application performance testing

[0070] Fig.11 In order to test the device structure diagram of the thin film transistor of the conjugated fully fused materials E1 / E2 / E3 / E4 / E5, a device structure with a gate top contact was adopted, and the gate layer, the insulating layer, the E1 / E2 / E3 / E4 / E5 organic semiconductor layer, and the source and drain electrode layers were deposited in sequence on the substrate material.

[0071] The results show that the mobility (cm 2 V -1 s -1 ) is approximately 10 -2 Order of magnitude; E3 molecules can be regarded as molecules obtained by conjugation extension of E1 molecules. Improving mobility by conjugation extension is a common solution to improve mobility. The carrier mobility of material E3 is 0.1cm 2 V -1 s -1 .

[0072] E4 and E5 are isomers of E3 molecule. E3 molecule has the smallest energy level difference among this series of isomers and is used as the representative of this series of molecules for making thin film transistors. E2 is an isomer of E1 molecule. E2, E4 and E5 also have high 10 -2 Carrier mobility of orders of magnitude and above.

Claims

1. A U-shaped conjugated fused material containing thiophene derivatives, characterized in that: Its general structural formula is shown in Formula 1), Formula 2), Formula 3), Formula 4) or Formula 5): In the formula, R1 is C1-C 30 Alkyl, phenyl, C1-C 30 Alkyl or C1-C 30 Alkoxy substituted phenyl.

2. The U-shaped conjugated fused material containing a thiophene derivative according to claim 1, characterized in that: R1 is C 10 -C 30 Alkyl, or any one of the chemical groups shown in Formula 6) to Formula 8): In the formula, R2, R3, and R4 are independently C1-C 10 Alkyl or C1-C 10 Alkoxy.

3. A method for preparing a U-shaped conjugated fused material containing a thiophene derivative as claimed in claim 1, characterized in that: The method comprises the following steps: firstly, compound A and compound B1, B2, B3, B4 or B5 are used as starting materials, and corresponding products C1, C2, C3, C4 or C5 are prepared through Suzuki coupling reaction; then, compound C1, C2, C3, C4 or C5 and methyl methoxy triphenyl phosphonium chloride are subjected to Wittig reaction under the action of a base to produce products D1, D2, D3, D4 or D5; finally, compound D1, D2, D3, D4 or D5 is subjected to Friedel-Crafts reaction under the action of a catalyst to produce a U-shaped conjugated fused material containing a thiophene derivative as shown in formula 1), formula 2), formula 3), formula 4) or formula 5), ​​and the synthesis route thereof is as follows: Where R1 is C1-C 30 Alkyl, phenyl, C1-C 30 Alkyl or C1-C 30 Alkoxy substituted phenyl.

4. The method for preparing a U-shaped conjugated fused material containing a thiophene derivative according to claim 3, characterized in that: The specific conditions of the Suzuki coupling reaction are as follows: in a solvent, in the presence of a base, a catalyst and a ligand, compound A is subjected to a Suzuki coupling reaction with compound B1, B2, B3, B4 or B5 to obtain the corresponding compound C1, C2, C3, C4 or C5.

5. The method for preparing a U-shaped conjugated fused material containing a thiophene derivative according to claim 4, characterized in that: The solvent is selected from one or more of water, benzene, toluene, xylene, decahydronaphthalene, diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, 1,1-diethoxymethane, chloroform, 1,2-dichloroethane or anisole; The base is selected from one or more of sodium tert-butoxide t-BuONa, potassium tert-butoxide t-BuOK, potassium carbonate K2CO3, sodium carbonate Na2CO3 or potassium phosphate K3PO4; The catalyst is selected from one or more of tetrakis(triphenylphosphine)palladium Pd(PPh3)4, bis(dibenzylideneacetone palladium Pd(dba)2, tris(dibenzylideneacetone)dipalladium trichloromethane Pd2(dba)3·CHCl3, tris(dibenzylideneacetone)dipalladium Pd2(dba)3, palladium acetate Pd(OAc)2, palladium dichloride PdCl2 or chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II); The ligand is selected from one or more of triphenylphosphine PPh3, tri-tert-butylphosphine P(t-Bu)3, tri-tert-butylphosphine tetrafluoroborate, 2,2′-bis(diphenylphosphine)-1,1′-binaphthyl BINAP, 2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl SPhos, 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl Xphos, 1,2,3,4,5-pentylphenyl-1′-(di-tert-butylphosphine)ferrocene Qphos, 2-dicyclohexylphosphine-2′-methylbiphenyl MePhos, 2-(di-tert-butylphosphine)biphenyl JohnPhos or 4,5-bisdiphenylphosphine-9,9-dimethylxanthene XantPhos.

6. The method for preparing a U-shaped conjugated fused material containing a thiophene derivative according to claim 4, characterized in that: The volume molar ratio of the solvent to the compound A is 2:1 to 50:1 mL / mmol; the molar ratio of the compound A to the compound B1, B2, B3, B4 or B5 is 0.1:1 to 0.5:1; the reaction temperature is 25°C to 100°C, and the reaction time is 6h-48h.

7. The method for preparing a U-shaped conjugated fused material containing a thiophene derivative according to claim 3, characterized in that: The Wittig reaction conditions are as follows: the reaction is carried out in an ice bath, the base is potassium tert-butoxide, the reaction solvent is tetrahydrofuran, and the reaction time is 1-3 hours.

8. The method for preparing a U-shaped conjugated fused material containing a thiophene derivative according to claim 3, characterized in that: The Friedel-Crafts reaction conditions are as follows: the reaction is carried out at room temperature, the catalyst is bismuth trifluoromethanesulfonate (Bi(OTf)3), the reaction solvent is 1,2-dichloroethane, and the reaction time is 1-3 hours.

9. Use of the U-shaped conjugated fused material containing a thiophene derivative as claimed in any one of claims 1 to 2 in an organic field effect transistor.

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