Cyclic imide derivatives with high-efficiency multi-exciton effect and synthesis method and application thereof

Abstract

The application provides a cyclic imide derivative with a high-efficiency multi-exciton effect and a synthesis method and application thereof, and belongs to the technical field of organic optoelectronic materials. The cyclic imide derivative has any one of the following structural formulae: wherein n is 1 or 2 or 3; m is an integer in 1-15; Ar represents an aryl group; and R is selected from a substituted or unsubstituted C1-C15 alkyl chain or a phenyl chain. The application directly synthesizes a novel cyclic compound through a synthesis method, and a series of different cyclic imide compounds can be further synthesized by changing the number of aryl groups on the ring and the type of imide compounds. Experimental tests prove that the cyclic imide compound can be applied in the field of singlet fission materials, and excellent bipolar transport performance is exhibited when the cyclic imide compound is applied in an organic field effect transistor device, so the cyclic imide compound has a good industrial application prospect.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic optoelectronic materials, in particular to a cyclic imide derivative with high-efficiency multi-exciton effect and a synthesis method and application thereof. BACKGROUND

[0002] Singlet fission (SF) is a multi-exciton generation process found in organic semiconductors, in which a photoexcited chromophore has electronic interaction with an adjacent ground-state chromophore, converting a singlet exciton (S1) into two triplet excitons (2 x T1) via an intermediate triplet pair (1(TT)). SF shows great promise in breaking the Shockley-Queisser limit of photovoltaic cells, and the third-generation solar cell based on the carrier multiplication type (singlet fission) can theoretically increase the energy conversion efficiency of a single-junction device from about 33% to about 44%. In addition, the 3(TT) state and 5(TT) state generated by the spin evolution of the 1(TT) state have also attracted extensive attention from researchers due to their potential applications in quantum information science.

[0003] At present, singlet fission materials mainly focus on materials such as acenes, and the types of materials are relatively limited, which greatly limits the application of semiconductor devices with singlet fission properties. Therefore, it is of great significance to develop new organic semiconductor materials with multi-exciton effect. SUMMARY

[0004] In view of the technical problems existing in the background art, the present application provides a cyclic imide derivative with high-efficiency multi-exciton effect and a synthesis method and application thereof, aiming to solve the technical problems of the prior art that the types of singlet fission materials are few and the synthesis is difficult.

[0005] In a first aspect, the present application provides a cyclic imide derivative with high-efficiency multi-exciton effect, which has any one of the following structural formulae:

[0006] ;

[0007] wherein n is 1 or 2 or 3; m is an integer from 1 to 15; Ar represents an aryl ring; and R is selected from a substituted or unsubstituted C1-C15 alkyl chain or a phenyl chain.

[0008] In a second aspect, the present application provides a synthesis method of a cyclic imide derivative with high-efficiency multi-exciton effect, comprising the following steps:

[0009] S1, reacting a first compound and a second compound in the presence of a first base, a palladium catalyst, and a first organic solvent and water to obtain an intermediate;

[0010] S2. The intermediate and tetrabutylammonium fluoride are reacted in the action of a second organic solvent to obtain a crude product. The crude product and hydrostannic acid are reacted in the action of a third organic solvent to obtain the target compound.

[0011] The structural formula of the first compound is:

[0012] ;

[0013] The structural formula of the second compound is:

[0014] ;

[0015] Where m is an integer from 1 to 15; Ar represents aryl; R is selected from substituted or unsubstituted C1 to C15 alkyl chains or phenyl chains.

[0016] Thirdly, the present invention provides cyclic imide derivatives with efficient multiexciton effects for use in the fabrication of organic field-effect transistor devices.

[0017] Compared with the prior art, the present invention has the following beneficial technical effects:

[0018] This invention directly synthesizes cyclic imide derivatives with multiexciton effects. Compared to the initial trinaphthalene-diphenylimide, this invention introduces a nanoring structure, synthesizing novel cyclic compounds. The synthetic route is simple, the raw materials are readily available, and the target cyclic imide derivatives can be synthesized in large quantities. By changing the number of aryl groups on the ring and the type of imide compound, a series of different cyclic imide compounds can be synthesized, promoting the development of singlet splitting materials. This invention studies the structure-property relationship between the target cyclic imide compound and its multiexciton effect properties, confirming its application in the field of singlet splitting materials. Organic field-effect transistor devices based on this material have been successfully fabricated, exhibiting excellent bipolar transport performance and showing promising industrial application prospects. Attached Figure Description

[0019] Figure 1 This is the hydrogen spectrum of compound TDI-[6]CPP obtained in Example 1 of this invention;

[0020] Figure 2 This is the mass spectrum of compound TDI-[6]CPP obtained in Example 1 of this invention;

[0021] Figure 3 This is the hydrogen spectrum of compound TDI-[9]CPP obtained in Example 2 of this invention;

[0022] Figure 4 This is the mass spectrum of compound TDI-[9]CPP obtained in Example 2 of this invention;

[0023] Figure 5 is a mass spectrum of compound TDI-[6]CPP2 prepared in Example 3 of the present application;

[0024] Figure 6 is a mass spectrum of compound TDI-[6]CPP2 prepared in Example 3 of the present application;

[0025] Figure 7 is an ultraviolet-visible (UV-vis) absorption spectrum of the compound prepared in Example 1 and Example 2 of the present application;

[0026] Figure 8 is a transient absorption spectrum of the compound prepared in Example 1 of the present application;

[0027] Figure 9 is a structure of an organic field effect transistor device prepared in Example 1 of the present application;

[0028] Figure 10 is a performance of an organic field effect transistor device prepared in Example 1 of the present application. DETAILED DESCRIPTION

[0029] The embodiments of the technical solutions of the present application will be described in detail below with reference to the accompanying drawings. The following examples are only used to more clearly illustrate the technical solutions of the present application, and therefore only serve as examples, and cannot limit the protection scope of the present application.

[0030] In the description of the embodiments of the present application, the technical terms "first", "second", etc. are only used to distinguish different objects, and cannot be understood as indicating or implying relative importance or implicitly indicating the number, specific order or primary and secondary relationship of the indicated technical features. In the description of the embodiments of the present application, the meaning of "a plurality of" is two or more, unless otherwise explicitly specified.

[0031] In a first aspect, the present application provides a cyclic imide derivative with high-efficiency multi-exciton effect, having any one of the following structural formulae:

[0032]

[0033] wherein n is 1 or 2 or 3; m is an integer from 1 to 15; Ar represents an aryl group; R is selected from a substituted or unsubstituted C1-C15 alkyl group or a phenyl chain.

[0034] Further, the phenyl chain includes a 2,6-diisopropylphenyl group.

[0035] Further, the Ar includes any one of a benzene ring, a naphthalene ring, a thiophene, and a pyridine.

[0036] Further, the cyclic imide derivative with high-efficiency multi-exciton effect has any one of the following structural formulae: Further, the cyclic imide derivative with high-efficiency multi-exciton effect has any one of the following structural formulae:

[0037] or or .

[0038] In a second aspect, the present application provides a method for synthesizing a cyclic imide derivative with high efficient multi-exciton effect, comprising the following steps:

[0039] S1, reacting the first compound and the second compound under the action of a first base, a palladium catalyst, and a first organic solvent and water to obtain an intermediate;

[0040] S2, reacting the intermediate and tetrabutylammonium fluoride under the action of a second organic solvent to obtain a crude product, and reacting the crude product and hydrogen stannate under the action of a third organic solvent to obtain the target compound;

[0041] wherein the first compound has the following structural formula:

[0042] ;

[0043] the second compound has the following structural formula:

[0044] ;

[0045] wherein m is an integer from 1 to 15; Ar represents an aryl group; and R is selected from a substituted or unsubstituted C1-C15 alkyl chain or a phenyl chain.

[0046] Further, the molar ratio of the first compound to the second compound is 1: (1.9-2.3), and more further 1:2; the first base is selected from at least one of anhydrous potassium phosphate, anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium acetate, anhydrous cesium carbonate, anhydrous cesium fluoride, anhydrous potassium fluoride, and anhydrous potassium tert-butoxide, and the molar ratio of the first compound to the first base is 1: (8-15), and more further 1:10; the palladium catalyst is selected from at least one of tetrakis triphenylphosphine palladium, palladium acetate, bis-triphenylphosphine palladium dichloride, tris(dibenzylideneacetone) dipalladium, and [1,1'-bis(diphenylphosphino) ferrocene] dichloropalladium, and the molar ratio of the first compound to the palladium catalyst is 1: (0.08-0.35), and more further 1:0.1; the first organic solvent is selected from at least one of oxygen-free 1,4-dioxane, tetrahydrofuran, 1,2-dichloroethane, and toluene; the volume ratio of the first organic solvent to water is 1: (0.08-0.15), and more further 1:0.1; and the usage ratio of the first compound to the first organic solvent is 1g: (300-800) mL, and more further 1g:500mL.

[0047] Further, the second organic solvent is selected from at least one of tetrahydrofuran, toluene, chlorobenzene, chloroform; the volume ratio of the intermediate and the second organic solvent is 1 g: (80-200) mL, and further 1 g: 100 mL; the volume ratio of the tetrabutylammonium fluoride and the second organic solvent is 1: (8-15), and further 1: 10; the third organic solvent is selected from at least one of tetrahydrofuran, toluene, chlorobenzene, chloroform; the volume ratio of the crude product and the third organic solvent is 1 g: (80-200) mL, and further 1 g: 150 mL; the volume ratio of the stannic hydride and the second organic solvent is 1: (40-80), and further 1: 50.

[0048] Further, the reaction temperature of the first compound and the second compound is 50-120℃, and further 75℃, and the reaction time is 12-16 h, and further 12 h; the reaction temperature of the intermediate and the tetrabutylammonium fluoride is room temperature, and the reaction time is 2-3 h, and further 2 h; the reaction temperature of the crude product and the stannic hydride is room temperature, and the reaction time is 12-16 h, and further 12 h.

[0049] In a third aspect, the present application provides a cyclic imide derivative with high multi-exciton effect for preparing an organic field effect transistor device.

[0050] Further, the cyclic imide derivative with high multi-exciton effect is used as an organic semiconductor layer of the organic field effect transistor device.

[0051] Some specific examples are listed below, and it should be noted that the examples described below are exemplary and are only used to explain the present application, and cannot be understood as a limitation of the present application. If the specific technology or condition is not specified in the examples, the technology or condition described in the literature in the art or according to the product manual is used. If the reagent or instrument is not specified by the manufacturer, it is a conventional product that can be obtained by purchase.

[0052] Example 1 Compound TDI-[6]CPP and a synthesis method thereof

[0053] The structure of the compound TDI-[6]CPP is as follows (type shown in Formula I):

[0054] .

[0055] The synthesis method of the compound TDI-[6]CPP described above is as follows:

[0056] (1) The first compound of triphenylenediimide tetrabromide (100 mg), the second compound of cyclo-p-phenyl cyclohexadiene derivative (((1's,1""s,4's,4""s)-4,4'''''-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1":4",1''':4''',1"":4"",1'''"-sexiphenyl]-1',1"",4',4""-tetrayl)tetrakis(oxy))tetrakis(triethylsilane) (200 mg), potassium phosphate (265 mg) and Pd (PPh3)4(15 mg) were added into a 500 mL two-necked flask, 250 mL oxygen-free 1,4-dioxane and 25 mL water were added into the flask under nitrogen protection, and the temperature was raised to 75 °C for 12 h. After the solution was cooled, 1,4-dioxane was removed by a vacuum rotary evaporator, and the crude product was purified by silica gel chromatography, eluted with petroleum ether / dichloromethane as the eluent, and a green intermediate was quickly obtained, but the intermediate was unstable, and was directly used in the next step;

[0057] (2) The intermediate was placed in a 100 mL reaction flask, 25 mL of tetrahydrofuran was added, and then 2.5 mL of tetrabutylammonium fluoride was added dropwise. After reaction at room temperature for 2 h, the tetrahydrofuran in the reaction solution was removed by a rotary evaporator, 50 mL of ultrapure water was added, and after stirring for half an hour, the product was filtered, dried, and then transferred to a dry 100 mL reaction flask, 50 mL of tetrahydrofuran was added, and then 1 mL of stannic chloride (H2SnCl4) solution was added to the reaction flask, and the reaction was carried out at room temperature for 12 h. The tetrahydrofuran was removed by a rotary evaporator, and the crude product was purified by silica gel chromatography, eluted with petroleum ether / dichloromethane as the eluent, and recrystallized to obtain the target compound TDI-[6]CPP. The hydrogen spectrum and mass spectrum of TDI-[6]CPP are shown in FIGS. 1 and 2, respectively. Figures 1-2 .

[0058] The specific reaction formula is as follows:

[0059] .

[0060] Example 2: Compound TDI-[9]CPP and its synthesis method

[0061] The structure of the compound TDI-[9]CPP is as follows (type shown in formula I):

[0062] .

[0063] The synthesis method of the above compound TDI-[9]CPP is as follows:

[0064] (1) The first compound of triphenylenediimide tetrabromide (100 mg), the second compound of cyclo-p-phenyl cyclohexadiene derivative (((1's,4's)-4'''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1":4",1'''-quaterphenyl]-1',4'-diyl)bis(oxy))bis(triethylsilane) (300 mg), potassium phosphate (265 mg) and Pd (PPh3)4(15 mg) were added into a 500 mL two-necked flask, 250 mL oxygen-free 1,4-dioxane and 25 mL water were added into the flask under nitrogen protection, and the reaction was carried out at 75°C for 12 h. The solution was cooled, 1,4-dioxane was removed by a vacuum rotary evaporator, and the crude product was purified by silica gel chromatography, eluted with petroleum ether / dichloromethane as the eluent, and a green intermediate was quickly obtained, but the intermediate was poor in stability, and was directly used in the next step.

[0065] (2) The intermediate was placed into a 100 mL reaction flask, 25 mL tetrahydrofuran was added, and then 2.5 mL tetrabutylammonium fluoride was added dropwise. After reaction at room temperature for 2 h, the tetrahydrofuran in the reaction solution was removed by a rotary evaporator, 50 mL ultrapure water was added, and after stirring for half an hour, the product was filtered, and a dark green crude product was obtained. After drying, the product was transferred into a dry 100 mL reaction flask, 50 mL tetrahydrofuran was added, and then 1 mL hydrogen stannic chloride (H2SnCl4) solution was added into the reaction flask, and the reaction was carried out at room temperature for 12 h. The next day, the tetrahydrofuran was removed by a rotary evaporator, the crude product was purified by silica gel chromatography, eluted with petroleum ether / dichloromethane as the eluent, and the target compound TDI-[9]CPP was obtained after recrystallization. The hydrogen spectrum and mass spectrum of TDI-[9]CPP are shown in FIGS. 1 and 2, respectively. Figures 3-4 .

[0066] The specific reaction formula is as follows:

[0067] .

[0068] Example 3: Compound TDI-[6]CPP2 and its synthesis method

[0069] The structure of the compound TDI-[6]CPP2 is as follows (type shown in formula II):

[0070] .

[0071] The synthesis method of the compound TDI-[6]CPP2 is as follows:

[0072] (1) The first compound of triphenylenediimide tetrabromide (100 mg), the second compound of cyclo-p-phenyl cyclohexadiene derivative (((1's,1""s,4's,4""s)-4,4'''''-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1":4",1''':4''',1"":4"",1'''"-sexiphenyl]-1',1"",4',4""-tetrayl)tetrakis(oxy))tetrakis(triethylsilane) (200 mg), potassium phosphate (265 mg) and Pd (PPh3)4(15 mg) were added into a 500 mL two-necked flask, 250 mL oxygen-free 1,4-dioxane and 25 mL water were added into the flask under nitrogen protection, the temperature was raised to 75 °C and reacted for 12 h, the solution was cooled, 1,4-dioxane was removed by a vacuum rotary evaporator, the crude product was purified by silica gel chromatography, eluted with petroleum ether / dichloromethane as eluent, and a green intermediate was quickly obtained, but the intermediate was poor in stability, and was directly used in the next step;

[0073] (2) The intermediate was placed into a 100 mL reaction flask, 25 mL of tetrahydrofuran was added, then 2.5 mL of tetrabutylammonium fluoride was added dropwise, the reaction was carried out at room temperature for 2 h, then the tetrahydrofuran in the reaction solution was removed by a rotary evaporator, 50 mL of ultrapure water was added, stirred for half an hour, then filtered, a dark green crude product was obtained, the product was dried, then transferred to a dry 100 mL reaction flask, 50 mL of tetrahydrofuran solvent was added, then 1 mL of hydrogen stannic chloride (H2SnCl4) solution was added into the reaction flask, the reaction was carried out at room temperature for 12 h, the tetrahydrofuran was removed by a rotary evaporator, the crude product was purified by silica gel chromatography, eluted with petroleum ether / dichloromethane as eluent, and the target compound TDI-[6]CPP2 was obtained after recrystallization, the hydrogen spectrum and mass spectrum of TDI-[6]CPP2 are shown in Figures 5-6 .

[0074] The specific reaction formula is as follows:

[0075] .

[0076] Test Example 1: Study on steady-state spectral properties

[0077] The compounds TDI-[6]CPP and TDI-[9]CPP were dissolved in chloroform, and the ultraviolet-visible absorption spectrum was tested by a UV-1800 type ultraviolet-visible spectrophotometer, as shown in Figure 7 . According to the starting absorption wavelength λ onset and the energy gap formula: E g opt = 1240 / λonset (eV), calculated E g opt (TDI-[6]CPP) = 1.44 eV; E g opt (TDI-[9]CPP) = 1.48 eV. The results show that the introduction of the cyclic structure effectively changes the optical gap band, and the increase of the ring size can further adjust the optical properties.

[0078] Test Example 2: Transient absorption spectrum test to study the multi-exciton effect

[0079] The test example provides a test method and process of femtosecond transient absorption spectrum to explore the multi-exciton effect, including the following steps:

[0080] (1) Preparation of sample concentrated solution: 1 mg of sample (compound prepared in Example 1 of the application) was dissolved in 50 μL of chloroform solution, and stirred for 30 min;

[0081] (2) Preparation of sample thin film: the quartz piece was fixed on the spin coater; the spin coater was turned on, the rotation speed was set to 1500 rpm, and the spin coating time was 50 s; 35 μL of concentrated solution was taken by a pipette gun, and dropped on the quartz piece to obtain a well-spread thin film sample;

[0082] (3) Test of femtosecond transient absorption spectrum of the film phase sample

[0083] The femtosecond transient absorption spectrum experiment was completed by using a wide-band pump-probe device of Newport Company, USA. The system used an amplified laser system (Spirit 1040-8-SHG) with a frequency of 200 KHz to generate laser pulses with a duration response of 400 fs at 1040 nm. The probe beam was a supercontinuum white light, which spanned the spectral region of 530 nm-1000 nm, which was generated by focusing a small part of the 1040 nm laser pulse onto a YAG crystal. The remaining 1040 nm laser pulse generated a 520 nm pump pulse by second harmonic generation, and the pump light time delay was controlled by a mechanical delay platform. The excitation flux before each measurement sample was about 7.5 μJ / cm 2 , to confirm that the dynamics is independent of the pump light intensity.

[0084] The transient absorption spectrum of the compound prepared in Example 1 of the application is shown in Figure 8 The spectrum shows that the newly prepared compound has an effective singlet fission process, and after the sample is excited by light, it reaches the singlet state, and gradually dissociates into two triplet states with the increase of the time scale.

[0085] Test Example 3

[0086] Device preparation and performance characterization of organic field effect transistor

[0087] The newly synthesized target compound TDI-[6]CPP (R=C6H 13 ) of Example 1 was used as an organic semiconductor layer to prepare a bottom-gate top-contact organic field effect transistor device structure (as shown in FIG. 1). Figure 9

[0088] The specific preparation process is as follows:

[0089] (1) A heavily doped silicon wafer (1.3 square centimeters in area) containing a 300 nm oxide layer was placed in a water solution containing a cleaning agent and ultrasonically cleaned for 15 minutes, then cleaned in deionized water for 10 minutes, and finally ultrasonically cleaned in acetone and isopropanol for 15 minutes each. The clean silicon wafer was blown dry with nitrogen and reserved for use;

[0090] (2) A piranha solution was prepared using concentrated sulfuric acid and hydrogen peroxide (7:3, v / v), and the clean silicon wafer was immersed in the piranha solution for 30 minutes, then ultrasonically cleaned several times with deionized water, and blown dry with a nitrogen gun and reserved for use;

[0091] (3) The treated silicon wafer was placed in a culture dish, and one drop of octadecyltrichlorosilane (OTS) was added, followed by vacuum drying treatment at 120°C for 2 hours. The OTS-modified silicon wafer was ultrasonically cleaned in toluene and isopropanol for 15 minutes each, and blown dry and reserved for use;

[0092] (4) The compound TDI-[6]CPP (R=C6H 13 ) was dissolved in chloroform to prepare a solution with a concentration of 5 mg / mL, and then a thin film of the compound TDI-[6]CPP (R=C6H 13 ) was prepared on the OTS-modified silicon wafer using a spin coating method at a speed of 3000 rpm for 60 seconds. The silicon wafer coated with the thin film of the compound TDI-[6]CPP (R=C6H 13 ) was placed on a hot plate and heated for 10 minutes at a temperature of 120°C;

[0093] (5) A mask containing an electrode pattern was placed on the silicon wafer coated with the thin film of the compound TDI-[6]CPP (R=C6H 13 ), and placed in a vacuum chamber and vacuumed to 5×10 -4 Pa. A 30 nm thick gold electrode was evaporated on the thin film of the compound TDI-[6]CPP (R=C6H 13 ) at a rate of 0.01 nm / s to obtain the OFET device provided by the application.

[0094] ​The test method is as follows: the instrument is a JIS 4200SCS semiconductor analyzer. The hole mobility is obtained by applying a bias voltage of -70 V at the OFET drain electrode and a scanning voltage of 0 to -70 V at the gate electrode during the test; the electron mobility is obtained by applying a bias voltage of 70 V at the OFET drain electrode and a scanning voltage of 0 to 70 V at the gate electrode.

[0095] After the test, it is found that the device exhibits bipolar transport performance, and the test results are shown in Figure 10 , the hole mobility is 0.0043 cm 2 V -1 s -1 , and the electron mobility is 0.0019 cm 2 V -1 s -1 Compared with other ring structures, the device based on the material exhibits more excellent bipolar transport performance, indicating its great application potential in the field of field effect transistors.

[0096] It should be noted that the present application is not limited to the above-mentioned embodiments. The above-mentioned embodiments are only examples, and embodiments having the same technical idea and playing the same role and effect within the scope of the technical solutions of the present application are all included in the technical scope of the present application. In addition, within the scope of the main idea of the present application, various modifications of the embodiments that can be thought of by those skilled in the art, other ways constructed by combining part of the constituent elements of the embodiments are also included in the scope of the present application.

Claims

1. A cyclic imide derivative exhibiting a highly efficient multiexciton effect, characterized in that, It has any of the following structural formulas: ； Where n is 1; m is an integer from 1 to 9; Ar represents a benzene ring; and R is 2,6-diisopropylphenyl.

2. The cyclic imide derivative with highly efficient multiexciton effect according to claim 1, characterized in that, It has any of the following structural formulas: or .

3. The method for synthesizing the cyclic imide derivative with highly efficient multiexciton effect according to any one of claims 1 to 2, characterized in that, Includes the following steps: S1. The first compound and the second compound are reacted in the presence of a first base, a palladium catalyst, a first organic solvent, and water to obtain an intermediate; S2. The intermediate and tetrabutylammonium fluoride are reacted in the action of a second organic solvent to obtain a crude product. The crude product and hydrostannic acid are reacted in the action of a third organic solvent to obtain the target compound. The structural formula of the first compound is: ； The structural formula of the second compound is: ； Where m is an integer from 1 to 9; Ar represents a benzene ring; and R is 2,6-diisopropylphenyl.

4. The method for synthesizing cyclic imide derivatives with highly efficient multiexciton effects according to claim 3, characterized in that, The molar ratio of the first compound to the second compound is 1:(1.9~2.3); the first base is selected from at least one of anhydrous potassium phosphate, anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium acetate, anhydrous cesium carbonate, anhydrous cesium fluoride, anhydrous potassium fluoride, and anhydrous potassium tert-butoxide, and the molar ratio of the first compound to the first base is 1:(8~15); the palladium catalyst is selected from tetrakis(triphenylphosphine)palladium, palladium acetate, bis(triphenylphosphine)palladium dichloride, tris(dibenzylideneacetone)palladium, [1,1'- The first compound is selected from at least one of bis(diphenylphosphino)ferrocene and palladium dichloride, wherein the molar ratio of the first compound to the palladium catalyst is 1:(0.08~0.35); the first organic solvent is selected from at least one of oxygen-free 1,4-dioxane, tetrahydrofuran, 1,2-dichloroethane, and toluene; the volume ratio of the first organic solvent to water is 1:(0.08~0.15); and the molar ratio of the first compound to the first organic solvent is 1g:(300~800)mL.

5. The method for synthesizing cyclic imide derivatives with highly efficient multiexciton effects according to claim 3, characterized in that, The second organic solvent is selected from at least one of tetrahydrofuran, toluene, chlorobenzene, and chloroform; the ratio of the intermediate to the second organic solvent is 1 g: (80~200) mL; the volume ratio of the tetrabutylammonium fluoride to the second organic solvent is 1: (8~15); the third organic solvent is selected from at least one of tetrahydrofuran, toluene, chlorobenzene, and chloroform; the ratio of the crude product to the third organic solvent is 1 g: (80~200) mL; the volume ratio of the hydrostannic acid to the second organic solvent is 1: (40~80).

6. The method for synthesizing cyclic imide derivatives with highly efficient multiexciton effects according to claim 3, characterized in that, The reaction temperature of the first compound and the second compound is 50~120℃, and the reaction time is 12~16h; the reaction temperature of the intermediate and tetrabutylammonium fluoride is room temperature, and the reaction time is 2~3h; the reaction temperature of the crude product and hydrostannic acid is room temperature, and the reaction time is 12~16h.

7. The application of the cyclic imide derivative with highly efficient multiexciton effect as described in any one of claims 1 to 2, characterized in that, The cyclic imide derivatives with efficient multiexciton effects are used in the fabrication of organic field-effect transistor devices.

8. The application of the cyclic imide derivative with highly efficient multiexciton effect according to claim 7, characterized in that, The cyclic imide derivative with efficient multiexciton effect is used as an organic semiconductor layer in an organic field-effect transistor device.

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