Synthesis method of ferrocene-based D-A type multi-system conjugated small molecule and memory device

Abstract

The invention discloses a ferrocene-based D-A type multi-system conjugated small molecule synthesis method, which comprises: carrying out a heating reaction in an organic solvent by using a ferrocenyl compound and a bromophenyl compound as raw materials and using a palladium complex as a catalyst, and after the reaction is completed, carrying out extraction, column chromatography and recrystallization to prepare an intermediate; the obtained intermediate and a 4-pyridine boric acid compound are used as raw materials, a palladium complex is used as a catalyst, a heating reaction is conducted in an organic solvent, and after the reaction is finished, cooling, extraction, column chromatography and recrystallization are conducted to prepare the D-A type multi-system conjugated small molecules. The invention also discloses a memory device with a sandwich structure and application of the memory device to ultra-high density information storage. The small molecular material prepared by the invention not only can realize ternary information storage performance, but also greatly improves the stability of the device through stable redox cycle of the ferrocene group, and realizes long-time stable ultrahigh-density information storage.

Description

Technical Field

[0001] The invention belongs to the field of functional semiconductor materials and electronic information, and relates to a synthesis method of a DA-type multi-ary conjugated small molecule based on ferrocene and a storage device. Background Art

[0002] In the field of information storage technology, resistive random access memory (ReRAM) has attracted considerable attention in recent years. With significant advantages such as high storage density, low power consumption, fast read / write speeds, and good compatibility with existing semiconductor processes, it has become a strong contender for next-generation storage technology. Early research on ReRAM focused on identifying material systems with resistive switching properties, focusing on transition metal oxides such as titanium dioxide (TiO2) and zinc oxide (ZnO). Simultaneously, through the combination of different materials and structural design, such as the construction of simple metal-oxide-metal (MIM) structures, the fundamental framework of ReRAM has been gradually established. Research has also revealed that certain organic small molecule / polymer materials exhibit significant changes in resistance when a voltage is applied.

[0003] Currently, an increasing number of functional semiconductor materials—such as small molecules, transition metal oxides, organometallic complexes, polymers, organic conjugated frameworks, graphene oxides, two-dimensional semiconductor materials, and perovskites—are being applied to the research of multi-level memory. Mechanisms such as charge trapping, charge transfer, redox reactions, conformational transitions, and filamentary conduction have also been applied to explain the phenomenon of multi-level memory. However, given the advantages of functional small molecules, such as well-defined molecular structures, reproducible synthesis, excellent thin film stacking, and consistent optoelectronic properties across batches, research has primarily focused on the careful design of small molecule structures, in the hope of producing multi-level memory materials and devices with long-term stability and excellent reproducibility.

[0004] However, the currently reported multi-level memory devices based on small molecule materials still have major problems in stability and reproducibility. This is mainly because the organic small molecule materials themselves still have certain problems in thermal stability and electrochemical stability, and therefore they cannot meet the ideal requirements in subsequent electrical performance tests and stability tests. Summary of the Invention

[0005] Purpose of the invention: The purpose of the present invention is to overcome the problems of insufficient thermal stability and electrochemical stability of small molecule materials in existing multi-binary memory devices, and to provide a synthesis method and memory device of DA-type multi-binary conjugated small molecules based on ferrocene, thereby realizing multi-binary memory materials and devices with long-term stability and high device reproducibility.

[0006] Ferrocene has high thermal and chemical stability, a unique sandwich structure, excellent redox activity, and outstanding electrochemical stability. Furthermore, integrating redox and charge transfer mechanisms into a single small molecule provides a novel strategy for the subsequent development of stable and reproducible organic multi-level memory devices.

[0007] Technical solution: The first solution of the present invention is to provide a method for synthesizing a DA-type polyvalent conjugated small molecule based on ferrocene, comprising the following steps: (1) Using a ferrocenyl compound and a bromophenyl compound as raw materials and a palladium complex as a catalyst, a heating reaction is carried out in an organic solvent. After the reaction is completed, extraction, column chromatography, and recrystallization are performed to prepare an intermediate; (2) Using the intermediate obtained in step (1) and a 4-pyridine boronic acid compound as raw materials and a palladium complex as a catalyst, a heating reaction is carried out in an organic solvent. After the reaction is completed, cooling, extraction, column chromatography, and recrystallization are performed to prepare a DA-type polyvalent conjugated small molecule.

[0008] Furthermore, in step (1), the ferrocenyl compound is a 1,1′-ferrocenyl halide selected from 1,1′-dibromoferrocene and 1,1′-diiodoferrocene; the bromophenyl compound is a 4-bromophenylboronic acid compound selected from 4-bromophenylboronic acid and 4-bromophenylboronic acid pinacol ester; or, The ferrocenyl compound is a 1,1′-ferrocenylboronic acid compound, selected from one of 1,1′-ferrocenyldiboronate and 1,1′-ferrocenyldiboronate pinacol ester; the bromophenyl compound is a 4-bromohalobenzene compound, selected from one of 1,4-dibromobenzene and 1-bromo-4-iodobenzene.

[0009] The synthesis route of the organic small molecule semiconductor material is shown in the following formula (I) or (II): (I) (II).

[0010] Furthermore, in step (1), the palladium complex catalyst is one of bis(triphenylphosphine)palladium dichloride (II), 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (II), and tetrakis(triphenylphosphine)palladium; and the organic solvent is one of ethylene glycol monomethyl ether and ethylene glycol dimethyl ether.

[0011] Furthermore, in step (1), the molar ratio of 1,1′-ferrocene halide to 4-bromophenylboronic acid compound is 1:(2-5); the amount of the palladium complex catalyst added is 1-5 mol% of the 1,1′-ferrocene halide; the molar ratio of 1,1′-ferroceneboronic acid compound to 4-bromohalobenzene compound is 1:(2-5); the amount of the palladium complex catalyst added is 1-5 mol% of the 1,1′-ferroceneboronic acid compound.

[0012] Furthermore, in step (1), the reaction is carried out in an oxygen-free environment at a reaction temperature of 70 to 90° C. and a reaction time of 120 to 360 hours.

[0013] Furthermore, in step (2), the 4-pyridine boronic acid compound is selected from one of 4-pyridine boronic acid and 4-pyridine boronic acid pinacol ester.

[0014] Furthermore, in step (2), the palladium complex catalyst is selected from one of bis(triphenylphosphine)palladium dichloride (II), 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (II), and tetrakis(triphenylphosphine)palladium; and the organic solvent is selected from one of tetrahydrofuran, 1,4-dioxane, and toluene.

[0015] Furthermore, in step (2), the molar ratio of the intermediate to the 4-pyridine boronic acid compound is 1:(2-5); and the amount of the palladium complex catalyst added is 1-5 mol% of the intermediate.

[0016] Furthermore, in step (2), the reaction is carried out in an oxygen-free environment at a reaction temperature of 70 to 90° C. and a reaction time of 48 to 72 hours.

[0017] A second embodiment of the present invention provides a memory device, wherein the memory device is prepared using a ferrocene-based DA-type poly-conjugated small molecule prepared by the above-mentioned synthesis method of a ferrocene-based DA-type poly-conjugated small molecule, and comprises the following steps: (1) Dissolve the synthesized DA-type polyvalent conjugated small molecule in an organic solvent, heat and sonicate, and obtain a spin coating solution after the solution becomes clear and transparent; (2) Squeeze 4 drops of the spin coating solution prepared in step (1) onto the clean surface of indium tin oxide glass using a syringe equipped with a 0.22 μm pore filter. After dripping, use a spin coater to spin coat to obtain a uniform organic thin film layer; (3) The organic film prepared in step (2) is placed in a high vacuum evaporator, and a layer of aluminum electrode with a thickness of 100 nm is evaporated on its surface to obtain a sandwich structure electrical storage device.

[0018] Beneficial effects: Compared with the prior art, the present invention has the following significant advantages: (1) The DA-type polyvalent conjugated small molecule described in the present invention has a simple structure, and the overall molecular skeleton is a linear and rigid conjugated planar structure, which is conducive to the close and orderly stacking of molecules, and no long alkyl chain is introduced into the molecular skeleton to interfere with the orderly stacking of molecules.

[0019] (2) The ferrocene introduced into the DA-type multi-binary conjugated small molecule of the present invention has high light, heat and chemical stability, which is beneficial to improving the chemical stability of the synthesized small molecule, thereby solving the problem of poor long-term stability in multi-binary memory devices based on small molecules.

[0020] (3) The ferrocene introduced into the DA-type poly-conjugated small molecule of the present invention has extremely excellent electrochemical stability and outstanding redox activity. Its core group is a ferrocene group. Under the action of an electric field, ferrocene (Fe) can be oxidized to ferrocenium ions (Fe + ), thereby changing the resistance of the molecules, ultimately affecting the conductivity of the molecular film and achieving storage performance. Furthermore, the pyridine group introduced at the end of the molecule is a typical electron-withdrawing group. Under the action of an electric field, it can induce charge transfer between molecules, further changing the conductive properties of the molecular film.

[0021] (4) The DA-type multi-ary conjugated small molecules described in the present invention organically integrate the redox and charge transfer mechanisms, which not only improves the reproducibility and stability of the device, but also provides new ideas for the subsequent design of multi-ary small molecules. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 The H NMR spectrum of the intermediate [3] in Example 1 ( 1 H NMR) spectra; Figure 2 This is the H NMR spectrum of the organic DA type multi-ary conjugated small molecule of Example 18 ( 1 H NMR) spectra; Figure 3 This is the theoretical simulation of the organic DA-type multi-ary conjugated small molecule of Example 18; Figure 4 The X-ray diffraction (XRD) pattern of the organic thin film prepared in Example 32; Figure 5 A diagram of a "sandwich" structure memory device prepared in Example 32; Figure 6 The electrical performance diagram obtained for the test case; Figure 7 This is the long-term stability performance diagram obtained for the test case. DETAILED DESCRIPTION

[0023] The present invention will be further described below with reference to the accompanying drawings and specific embodiments so that those skilled in the art can better understand the present invention and implement it. However, the embodiments are not intended to limit the present invention.

[0024] Example 1

[0025] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.68 g of an orange-red intermediate [3], with a calculated yield of approximately 69%.

[0026] Attachment Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the intermediate of the organic DA type polyvalent conjugated small molecule [3]. From the 1HNMR spectrum, it can be seen that the nuclear magnetic peaks at δ of 4.62 and 4.23 ppm can be attributed to CH on the five-membered ring of ferrocene, and the peak at δ of 7.23-7.11 ppm can be attributed to the hydrogen atoms on the aromatic ring.

[0027] Example 2

[0028] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.41 g, 5.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.75 g of an orange-red intermediate [3], with a calculated yield of approximately 76%.

[0029] Example 3

[0030] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (2.82 g, 10.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature of the reaction system was then raised to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.76 g of an orange-red intermediate [3], with a calculated yield of approximately 77%.

[0031] Example 4

[0032] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.41 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (30 mg, 0.04 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature of the reaction system was then raised to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.78 g of an orange-red intermediate [3], with a calculated yield of approximately 79%.

[0033] Example 5

[0034] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.41 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (75 mg, 0.10 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.71 g of an orange-red intermediate [3], with a calculated yield of approximately 72%.

[0035] Example 6

[0036] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature of the reaction system was then raised to 80°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). After the obtained organic phase is dried over anhydrous sodium sulfate, the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.72 g of an orange-red intermediate [3], with a calculated yield of approximately 73%.

[0037] Example 7

[0038] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature was then raised to 90°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.80 g of an orange-red intermediate [3], with a calculated yield of approximately 81%.

[0039] Example 8

[0040] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 240 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.78 g of an orange-red intermediate [3], with a calculated yield of approximately 79%.

[0041] Example 9

[0042] The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 360 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.81 g of an orange-red intermediate [3], with a calculated yield of approximately 82%.

[0043] Example 10: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol monomethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution and stirred for 30 minutes. Under a nitrogen atmosphere, the catalyst, bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.02 mmol), was added to the reaction system and stirred thoroughly. The reaction system was then purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.65 g of an orange-red intermediate [3], with a calculated yield of approximately 66%.

[0044] Example 11: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution and stirred for 30 minutes. Under a nitrogen atmosphere, the catalyst, bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.02 mmol), was added to the reaction system and stirred thoroughly. The reaction system was then purged with nitrogen three times. The temperature was then raised to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried with anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.52 g of an orange-red intermediate [3], with a calculated yield of approximately 53%.

[0045] Example 12: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to this solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakis(triphenylphosphine)palladium (23 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.50 g of an orange-red intermediate [3], with a calculated yield of approximately 51%.

[0046] Example 13: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1-Bromo-4-iodobenzene (1.13 g, 4.00 mmol) and 1,1′-ferrocenyldiboronic acid pinacol ester (0.88 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to this solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakis(triphenylphosphine)palladium (23 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 36 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried with anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.87 g of an orange-red intermediate [3], with a calculated yield of approximately 88%.

[0047] Example 14: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 1,4-Dibromobenzene (0.94 g, 4.00 mmol) and 1,1'-ferrocene diboronate (0.54 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution and stirred for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.68 g of an orange-red intermediate [3], with a calculated yield of approximately 69%.

[0048] Example 15: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 4-Bromophenylboronic acid (0.80 g, 4.00 mmol) and 1,1'-dibromoferrocene (0.69 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature of the reaction system was then raised to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.61 g of an orange-red intermediate [3], with a calculated yield of approximately 62%.

[0049] Example 16: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 4-Bromophenylboronic acid pinacol ester (1.13 g, 4.00 mmol) and 1,1'-dibromoferrocene (0.69 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.63 g of an orange-red compound [3], with a calculated yield of approximately 64%.

[0050] Example 17: The synthesis of the intermediate of organic DA-type polyvalent conjugated small molecule [3] is as follows: 4-Bromophenylboronic acid pinacol ester (1.13 g, 4.00 mmol) and 1,1'-diiodoferrocene (0.86 g, 2.0 mmol) were dissolved in 40 mL of ethylene glycol dimethyl ether and stirred thoroughly to obtain a clear solution. A 3.0 M aqueous sodium hydroxide solution (5 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (15 mg, 0.02 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 120 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with ethyl acetate solvent. The obtained aqueous phase is extracted three times with 50 mL of ethyl acetate. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in n-hexane solvent until a slurry is formed. It is then filtered and recrystallized to obtain 0.69 g of an orange-red intermediate [3], with a calculated yield of approximately 70%.

[0051] Example 18: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid (0.42 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakis(triphenylphosphine)palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.58 g of a red conjugated small molecule [5], and its yield is calculated to be about 70%.

[0052] Attachment Figure 2 This is the H NMR spectrum of the organic DA type multi-ary conjugated small molecule - 1,1'-bis (4-phenylpyridyl) ferrocene, attached Figure 3 This is a theoretical simulation diagram of an organic DA-type multi-ary conjugated small molecule - 1,1'-bis(4-phenylpyridyl)ferrocene. 1 The H NMR spectrum shows that the doublet with a chemical shift of 8.59-8.58 ppm has the strongest polarization capability, corresponding to the hydrogen atoms near the nitrogen atom on the pyridine functional group in the small molecule. The continuous peaks at 7.45-7.31 ppm correspond to aromatic hydrogen atoms on the pyridine and phenyl functional groups in the small molecule. Finally, two NMR peaks with chemical shifts at 4.58 and 4.32 ppm correspond to two groups of hydrogen atoms on the five-membered ring of ferrocene in the small molecule. Theoretical simulations show that the pyridine group at the end of the organic DA-type multi-ary conjugated small molecule backbone is a typical electron-withdrawing group. Under electric field stimulation, metal-to-ligand charge transfer (MLCT) and electron-donating to electron-withdrawing charge transfer processes can occur within the molecular backbone, theoretically enabling multi-ary storage performance.

[0053] Example 19: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.60 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 72%.

[0054] Example 20: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of 1,4-dioxane and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.55 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 66%.

[0055] Example 21: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of tetrahydrofuran and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.51 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 62%.

[0056] Example 22: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, bis(triphenylphosphine)palladium(II) dichloride (12 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature was then raised to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.44 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 52%.

[0057] Example 23: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (12 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The temperature was then raised to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.46 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 56%.

[0058] Example 24: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 80°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.50 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 60%.

[0059] Example 25: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 90°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.54 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 64%.

[0060] Example 26: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 90°C under nitrogen protection and the reaction continued at this temperature for 72 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.52 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 62%.

[0061] Example 27: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 90°C under nitrogen protection and the reaction continued at this temperature for 64 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.51 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 61%.

[0062] Example 28: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (1.75 g, 8.5 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.66 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 76%.

[0063] Example 29: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (1.05 g, 5.1 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (19 mg, 0.017 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed by rotary evaporation under reduced pressure and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.57 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 68%.

[0064] Example 30: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (38 mg, 0.034 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.61 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 73%.

[0065] Example 31: The synthesis of organic DA-type poly-conjugated small molecules [5] is as follows: 4-Pyridineboronic acid pinacol ester (0.70 g, 3.4 mmol) and compound 3 (0.85 g, 1.7 mmol) were dissolved in 20 mL of toluene and 8 mL of ethanol. A 3.0 M aqueous sodium hydroxide solution (12 mL) was then added to the solution, and stirring continued for 30 minutes. Under a nitrogen atmosphere, the catalyst, tetrakistriphenylphosphine palladium (95 mg, 0.085 mmol), was added to the reaction system. After thorough stirring, the reaction system was purged with nitrogen three times. The system was then heated to 70°C under nitrogen protection and the reaction continued at this temperature for 48 hours. After the reaction is completed, the temperature is lowered to room temperature. During this period, the reaction mixture is stirred until it cools to room temperature. Then, an appropriate amount of deionized water is added to the reaction system and extracted with dichloromethane solvent. The obtained aqueous phase is extracted three times with 50 mL of dichloromethane. The obtained organic phases are combined. Finally, the organic phase is washed and extracted once with saturated NH4Cl solution (100 mL), water (100 ml) and saturated brine (100 ml). The obtained organic phase is dried over anhydrous sodium sulfate, and the organic solvent is removed under reduced pressure on a rotary evaporator and concentrated to an orange-red solid. The solid residue is dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. Subsequently, the eluted solvent is removed under reduced pressure to obtain an orange powder, which is then ultrasonically dispersed in petroleum ether solvent until a slurry is formed. It is then filtered to obtain 0.59 g of a red conjugated small molecule [5], and its yield is calculated to be approximately 71%.

[0066] Example 32: The preparation of organic "sandwich" structure memory devices, the specific steps are as follows: First, weigh 12 mg of 1,1'-bis(4-phenylpyridyl)ferrocene small molecules and disperse them in 1 ml of diphenylmethane solvent to control the concentration to 12 mg / mL. Ultrasonicate to completely dissolve it to form a clear and transparent solution system. Secondly, extract the solution system with a syringe, and then install an organic filter head with a diameter of 0.22 μm on the syringe. Slowly add 4 drops of this solution system on the surface of the ITO glass. Then, set the initial coating speed of the spin coater to 400 rpm and the coating time to 15 seconds; set the subsequent spin coating speed of the spin coater to 2500 rpm and the spin coating time to 30 seconds. After spin coating, place the obtained organic film in a vacuum oven for solvent volatilization treatment. The oven temperature is set to 60°C and the vacuum degree is set to 10 -3 Finally, a mask is placed on the surface of the organic film, and the aperture of the mask is 120 microns. Then the organic film with the mask is placed in a high vacuum evaporation device, and the vacuum degree is set to 10 -6Thor, adjust the current of the vacuum evaporation equipment to control the evaporation speed of aluminum particles to 1 angstrom per second, set the thickness of the aluminum electrode to 100 nanometers, and after the evaporation is completed, you can get the following Figure 5 The "sandwich" structure memory device shown in the figure is shown in the figure. Figure 5 (a) is a physical picture of a memory device with a "sandwich" structure prepared by organic DA-type multi-binary conjugated small molecules, attached Figure 5 Middle (b) is a simulation diagram of a "sandwich" structure prepared by organic DA-type multi-binding conjugated small molecules, where 9 is a glass substrate, 10 is an ITO layer, 11 is a molecular layer, which is an organic thin film prepared by organic DA-type multi-binding conjugated small molecules, and 12 is an aluminum electrode.

[0067] Attachment Figure 4 The X-ray diffraction (XRD) pattern of an organic film prepared using an organic DA-type poly-conjugated small molecule reveals five distinct diffraction peaks at double angles of 8.83°, 12.58°, 17.92°, 19.66°, and 21.05° (two peaks at double angles of 29.98° and 34.99° are characteristic of the ITO glass itself). The corresponding microscopic distances for these peaks are 10 Å, 7.03 Å, 4.94 Å, 4.51 Å, and 4.23 Å, respectively. The higher diffraction intensity of the 1,1'-bis(4-phenylpyridyl)ferrocene small molecule indicates a narrower half-maximum width (FWHM) of the corresponding diffraction peaks, indicating good crystallinity in the film. At the same time, the diffraction peak at a two-fold angle of 17.92° is almost exactly twice that at 8.83°, indicating that the 1,1'-bis(4-phenylpyridyl)ferrocene small molecule also forms long-range ordered layers and layered stacking in the film. This is mainly because the larger conjugated plane of the 1,1'-bis(4-phenylpyridyl)ferrocene small molecule is conducive to the surface-to-surface interaction between molecules. Such tightly ordered and long-range regular layer-to-layer stacking is very conducive to the effective transmission of charge carriers between films, which in turn is conducive to obtaining excellent electrical storage performance.

[0068] Test example: The memory device with a "sandwich" structure prepared in Example 32 was placed on a semiconductor test platform. When the device was subjected to multi-base storage performance and device reproducibility tests, the negative scanning voltage applied by the probe was 0 ~ -5 V, and the positive scanning voltage applied by the probe was 0 ~ 5 V. During the long-term stability test of the device, the constant DC voltage applied by the probe was -0.5 V, -2 V, and -4 V, and the application time was 10,000 seconds.

[0069] Attachment Figure 6The test results of the "sandwich" structure memory device show that the 1,1'-bis (4-phenylpyridyl) ferrocene small molecule can exhibit typical ternary storage performance. Figure 7 The display device can also exhibit excellent long-term stability, and its various conductive states can still be maintained when it is continuously powered for 10,000 seconds.

[0070] Obviously, the above embodiments are merely examples for clarity of explanation and are not intended to limit the implementation methods. Those skilled in the art will appreciate that other variations or modifications can be made based on the above description. It is not necessary and impossible to enumerate all implementation methods here. Obvious variations or modifications arising therefrom remain within the scope of protection of the present invention.

Claims

1. A method for synthesizing a DA-type polyvalent conjugated small molecule based on ferrocene, characterized in that: The following steps are involved: (1) Using a ferrocenyl compound and a bromophenyl compound as raw materials and a palladium complex as a catalyst, a heating reaction is carried out in an organic solvent. After the reaction is completed, extraction, column chromatography, and recrystallization are performed to prepare an intermediate; (2) Using the intermediate obtained in step (1) and a 4-pyridine boronic acid compound as raw materials and a palladium complex as a catalyst, a heating reaction is carried out in an organic solvent. After the reaction is completed, cooling, extraction, column chromatography, and recrystallization are performed to prepare a DA-type polyvalent conjugated small molecule.

2. The method for synthesizing a DA-type polyvalent conjugated small molecule based on ferrocene according to claim 1, wherein: In step (1), the ferrocenyl compound is a 1,1′-ferrocenyl halide selected from 1,1′-dibromoferrocene and 1,1′-diiodoferrocene; the bromophenyl compound is a 4-bromophenylboronic acid compound selected from 4-bromophenylboronic acid and 4-bromophenylboronic acid pinacol ester; or, The ferrocenyl compound is a 1,1′-ferrocenylboronic acid compound, selected from one of 1,1′-ferrocenyldiboronate and 1,1′-ferrocenyldiboronate pinacol ester; the bromophenyl compound is a 4-bromohalobenzene compound, selected from one of 1,4-dibromobenzene and 1-bromo-4-iodobenzene.

3. The method for synthesizing a DA-type polyvalent conjugated small molecule based on ferrocene according to claim 1, wherein: In step (1), the palladium complex catalyst is one of bis(triphenylphosphine)palladium(II) dichloride, 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, and tetrakis(triphenylphosphine)palladium; and the organic solvent is one of ethylene glycol monomethyl ether and ethylene glycol dimethyl ether.

4. The method for synthesizing a DA-type polyvalent conjugated small molecule based on ferrocene according to claim 2, wherein: In step (1), the molar ratio of 1,1′-ferrocene halide to 4-bromophenylboronic acid compound is 1:(2-5); the amount of the palladium complex catalyst added is 1-5 mol% of the 1,1′-ferrocene halide; the molar ratio of 1,1′-ferroceneboronic acid compound to 4-bromohalobenzene compound is 1:(2-5); the amount of the palladium complex catalyst added is 1-5 mol% of the 1,1′-ferroceneboronic acid compound.

5. The method for synthesizing a DA-type polyvalent conjugated small molecule based on ferrocene according to claim 1, wherein: In step (1), the reaction is carried out in an oxygen-free environment at a temperature of 70 to 90° C. and a reaction time of 120 to 360 hours.

6. The method for synthesizing DA-type polyvalent conjugated small molecules based on ferrocene according to claim 1, wherein: In step (2), the 4-pyridine boronic acid compound is selected from one of 4-pyridine boronic acid and 4-pyridine boronic acid pinacol ester.

7. The method for synthesizing DA-type polyvalent conjugated small molecules based on ferrocene according to claim 1, characterized in that: In step (2), the palladium complex catalyst is selected from one of bis(triphenylphosphine)palladium dichloride (II), 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride (II), and tetrakis(triphenylphosphine)palladium; and the organic solvent is selected from one of tetrahydrofuran, 1,4-dioxane, and toluene.

8. The method for synthesizing DA-type polyvalent conjugated small molecules based on ferrocene according to claim 1, wherein: In step (2), the molar ratio of the intermediate to the 4-pyridine boronic acid compound is 1:(2-5); and the amount of the palladium complex catalyst added is 1-5 mol% of the intermediate.

9. The method for synthesizing DA-type polyvalent conjugated small molecules based on ferrocene according to claim 1, wherein: In step (2), the reaction is carried out in an oxygen-free environment at a temperature of 70 to 90° C. and a reaction time of 48 to 72 hours.

10. A memory device, characterized in that: The DA-type poly-conjugated small molecule based on ferrocene prepared by the synthesis method of the DA-type poly-conjugated small molecule based on ferrocene according to any one of claims 1 to 9 is prepared, comprising the following steps: (1) Dissolve the synthesized DA-type polyvalent conjugated small molecule in an organic solvent, heat and sonicate, and obtain a spin coating solution after the solution becomes clear and transparent; (2) Squeeze 4 drops of the spin coating solution prepared in step (1) onto the clean surface of indium tin oxide glass using a syringe equipped with a 0.22 μm pore filter. After dripping, use a spin coater to spin coat to obtain a uniform organic thin film layer; (3) The organic film prepared in step (2) is placed in a high vacuum evaporator, and a layer of aluminum electrode with a thickness of 100 nm is evaporated on its surface to obtain a sandwich structure electrical storage device.

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