CN110627601A - Organic optoelectronic semiconductor material, preparation method and application thereof - Google Patents

Abstract

The invention discloses an organic optoelectronic semiconductor material and a preparation method and application thereof. The organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, 2,6-bis(9,10-ditriisopropylsilylethynyl) anthracenyl)naphthalene or 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene. The preparation method of an organic optoelectronic semiconductor material includes the following steps: in an inert gas environment, uniformly mixing reactant A, reactant B, tetrakis(triphenylphosphorus) palladium as a catalyst, toluene and potassium carbonate aqueous solution, and heating up after mixing The reaction is carried out at 90-100 DEG C for 24-96 hours, filtered to obtain a filter residue, and the filter residue is washed with a detergent to obtain an organic optoelectronic semiconductor material. The preparation reaction route provided by the invention has the advantages of simple and efficient, environment-friendly, cheap raw materials and low synthesis cost. The method has high universality and good repeatability; the invention provides a new choice for high-performance organic optoelectronic materials.

Description

Organic optoelectronic semiconductor material, preparation method and application thereof

technical field

The invention belongs to the technical field of organic optoelectronic semiconductor materials, and in particular relates to an organic optoelectronic semiconductor material and a preparation method and application thereof.

Background technique

Organic semiconductor devices such as organic solar cells (OPV), organic light emitting diodes (OLED), organic electrochromic (OEC) and organic thin film transistors (OTFT) have been developed and applied in many fields. In all these organic optoelectronic fields, organic optoelectronic materials are the key. Designing and synthesizing organic semiconductor materials with simple process, low cost, stable material properties and long life for commercialization will have broad application prospects.

Condensed acene materials are a class of organic materials with good optoelectronic properties. For example, the single crystal mobility of pentacene has reached 15-40 cm ² V ^-1 s ^-1 . Anthracene is the smallest member of the acene family with transistor properties and has good luminescence and device performance. In general, increasing conjugation can lead to higher charge carrier mobility in combination with increased transfer integral and decreased recombination energy. So keep the anthracene ring unchanged and add a naphthalene ring in the middle, which not only increases the conjugation, but also maintains the luminescence of anthracene.

Although a large number of organic semiconductor materials have been designed and synthesized, there are not many materials with high fluorescence quantum efficiency and high mobility. However, such materials are the key to the preparation of OLETs and OLEDs. Therefore, the preparation of such materials is crucial.

SUMMARY OF THE INVENTION

In view of the deficiencies of the prior art, the object of the present invention is to provide an organic optoelectronic semiconductor material, another object of the present invention is to provide a preparation method of the above-mentioned organic optoelectronic semiconductor material, and another object of the present invention is to provide the above-mentioned preparation method in the preparation of organic optoelectronic semiconductor materials. Applications in optoelectronic semiconductor materials.

The purpose of the present invention is achieved through the following technical solutions.

An organic optoelectronic semiconductor material whose structural formula is as follows:

Wherein, R ₁ is hydrogen or triisopropylsilyl acetylene, R ₂ is hydrogen or triisopropylsilyl acetylene, and the organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, 2,6-bis( 9,10-Ditriisopropylsilylethynylanthryl)naphthalene or 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene.

The preparation method of the above-mentioned organic optoelectronic semiconductor material comprises the following steps:

Under inert gas environment, reactant A, reactant B, tetrakis (triphenylphosphonium) palladium as catalyst, toluene and potassium carbonate aqueous solution are uniformly mixed, and after mixing, the temperature is raised to 90～100 ℃ and reacted for 24～96 hours, and filtered. The filter residue is obtained, and the filter residue is washed with a detergent to obtain the organic optoelectronic semiconductor material, wherein the ratio of the substance amount of the reactant A and the reactant B is (2.1-2.4): 1, the volume of the toluene The ratio of the parts, the amount of the reactant B and the amount of the potassium carbonate in the potassium carbonate aqueous solution is (9-15): 1: (4-15);

When the organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, the reactant A is 2-boronic acid anthracene, and the reactant B is 2,6-dibromonaphthalene;

When the organic optoelectronic semiconductor material is 2,6-bis(9,10-ditriisopropylsilylethynylanthracenyl)naphthalene, the reactant A is 2-bromo-9,10-ditriiso propylsilylethynyl anthracene, the reactant B is 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) Naphthalene;

When the organic optoelectronic semiconductor material is 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene, the reactant A is 2-boronic acid anthracene, and the reactant B is 2,6-Dibromo-1,5-bis(triisopropylsilylethynyl)naphthalene.

In the above technical solution, when the organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, the ratio of the substance amount of the reactant A and the reactant B is (2.1-2.2):1.

When the organic optoelectronic semiconductor material is 2,6-bis(9,10-ditriisopropylsilylethynylanthracenyl)naphthalene, the ratio of the amount of the reactant A and the reactant B is ( 2.2 to 2.4): 1.

When the organic optoelectronic semiconductor material is 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene, the ratio of the amount of the reactant A and the reactant B is ( 2.1 to 2.2): 1.

In the above technical solution, the ratio of the reactant B to the catalyst is 1:(0.05-0.1) in terms of the amount of substance.

In the above-mentioned technical scheme, the concentration of potassium carbonate in the potassium carbonate aqueous solution is 2M.

In the above technical solution, the inert gas is argon or nitrogen.

In the above technical solution, the unit of volume fraction is mL, and the unit of material fraction is mmol.

Application of the above preparation method in preparing the organic optoelectronic semiconductor material.

In the above technical solution, the yield of the preparation method is 69-89%.

Compared with the prior art, the beneficial effects of the present invention are as follows:

The preparation reaction route provided by the invention has the advantages of simple and efficient, environment-friendly, cheap raw materials and low synthesis cost; the method has high universality and good repeatability;

The present invention provides a new option for high-performance organic optoelectronic materials.

Description of drawings

Fig. 1 is the ultraviolet-visible absorption spectrum of 2,6-dianthracene-based naphthalene prepared in Example 1 in solid state;

Fig. 2 is the UPS curve that embodiment 1 obtains 2,6-dianthracene naphthalene;

Fig. 3 is the TGA curve of 2,6-dianthracene naphthalene prepared in Example 1;

Fig. 4 is the structural representation of organic field effect transistor;

Figure 5(a) is a typical transfer curve of OFETs prepared from 2,6-dianthracene naphthalene prepared in Example 1;

Figure 5(b) is the output curve of the OFETs prepared from 2,6-dianthracene naphthalene prepared in Example 1;

FIG. 6 is the single crystal structure of 2,6-dianthracene naphthalene prepared in Example 1. FIG.

Detailed ways

The technical solutions of the present invention are further described below in conjunction with specific embodiments.

The purchasing manufacturers and the purity of the medicines involved in the following examples are as follows:

The instruments and models involved in the test characterization in the following examples are as follows:

NMR: BRUKER AVANCE III

Mass Spectrometry: APEX II Fourier Transform Ion Cyclotron Resonance Mass Spectrometer (FT-ICR-MS)

Elemental analysis: FLASH EA1112 elemental analyzer

UV: UV2600 UV-Vis Spectrophotometer

UPS test: ESCALab250Xi multifunctional X-ray photoelectron spectrometer

Thermogravimetric testing: Thermal Analysis Excellence TGA 2

Device test: keithley 4200-scs

Crystal Analysis: Rigaku XtaLABmini Co., Ltd.

Example 1

The organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, and its structural formula is as follows:

The preparation method of the organic optoelectronic semiconductor material (2,6-dianthracene naphthalene) comprises the following steps:

7.69mmol of 2-boronic acid anthracene (2.34g), 3.5mmol of 2,6-dibromonaphthalene (1g) and 0.175mmol of tetrakis (triphenylphosphorus) palladium (202mg) as catalyst were placed in a 250mL there-necked flask, and evacuated After filling with argon three times, 50 mL of toluene and 25 mL of 2M potassium carbonate aqueous solution were added, and then the temperature of the reaction system was raised to 90° C. to carry out Suzuki coupling reaction, and the reaction continued for 96 hours. The reaction system was filtered, and the filter residue was washed successively with triethylamine and dichloromethane to obtain a crude product, which was sublimated and purified to obtain 1.5 g of a yellow solid, which was the organic optoelectronic semiconductor material of the present invention, and the yield was 89%.

The reaction process of the present embodiment is as follows:

Structural confirmation data for this product are shown below:

EI-MS: 480;

Elemental Analysis: Carbon: 94.98%, Hydrogen: 4.97%.

Elemental analysis showed that the yellow solid product had the correct structure and was 2,6-dianthracenthylnaphthalene.

The spectral properties, UPS test, thermodynamic properties of the 2,6-dianthracene-based naphthalene obtained in Example 1, and the determination of the properties of the organic field effect transistor are as follows:

1) Spectral properties of organic 2,6-dianthrylnaphthalene

Figure 1 shows the UV-Vis absorption spectrum of 2,6-dianthracenthylnaphthalene in the solid state. It can be seen from Figure 1 that the maximum absorption sideband peak of 2,6-dianthracene naphthalene in the solid state is 466 nm, and the corresponding optical band gap is 2.66 eV (the optical band gap is calculated according to the formula Eg=1240/λ, where Eg is the optical band gap. band gap, λ is the boundary value of the UV absorption curve).

2) UPS test of organic 2,6-dianthracene naphthalene

The ultraviolet light source used is He I without monochromatization, the energy of the He I light source used is 21.22eV, the basic vacuum of the analysis chamber during the UPS analysis and testing process of the equipment is 3.0X10 ^-8 Torr, and the bias added during the testing process is 3.0X10 -8 Torr. Voltage is -9V. The sample (2,6-dianthracenylnaphthalene) was evaporated under vacuum onto a silicon wafer of about 10 mm x 10 mm (1 cm x 1 cm) with a thickness of about 15 nm.

Figure 2 shows the UPS curve of 2,6-dianthracene naphthalene. It can be calculated from Figure 2 that the ionization potential of 2,6-dianthracene naphthalene is -5.42eV, that is, the HOMO value relative to the vacuum level is -5.42eV . It is shown that 2,6-dianthracene naphthalene has high oxidation stability and good hole injection ability.

3) Thermodynamic properties of organic 2,6-dianthracene naphthalene

Figure 3 shows the TGA curve of the material 2,6-dianthrylnaphthalene. It can be seen from the figure that the compound 2,6-dianthrylnaphthalene exhibits excellent thermal stability, and the decomposition temperature of thermal weight loss is 430°C.

4) Field effect transistor properties of organic 2,6-dianthracene naphthalene

Figure 4 is a schematic structural diagram of an organic field effect transistor. As shown in Figure 4, 1 is a Si/SiO ₂ substrate, while Si is used as a gate electrode, and 2 is an OTS (octadecyltrichlorosilane) modified SiO2 as an insulating layer. , 3 is the semiconductor micro-nanocrystalline layer of 2,6-dianthracene-based naphthalene, and 4 and 5 are the Au source and drain electrodes, respectively. The whole device adopts a bottom-gate top-contact configuration, that is, the device structure is Si(500μm)/SiO ₂ (300nm)/OTS (monolayer)/2,6-dianthracene naphthalene micro-nanocrystal/Au.

Figure 5 shows the transfer curve (Figure 5(a)) and the output curve (Figure 5(b)) of the micro-nano single crystal field effect transistor of 2,6-dianthracene naphthalene. The mobility μ is calculated using the following saturation region calculation formula (I):

Combining Fig. 5 and the above saturation formula (I), it can be known that in the range of V _G <-5V, the linear field effect transistor device works in the saturation region, and I _SD basically does not change; when V _G >-5V, The linear field effect transistor device works in the linear region, and the I _SD changes linearly. The calculated mobility of 2,6-dianthracenylnaphthalene is 19.6 cm ² V ^-1 s ^-1 . (For the calculation method of mobility, please refer to Chapter 2 of "Organic Field Effect Transistor", Chapter 2 Basic Introduction to Organic Field Effect Transistors, Author: Hu Wenping, Publisher: Science Press, ISBN 9787030320629.)

Figure 6 shows the single crystal structure of the organic 2,6-dianthracene naphthalene. The single crystal structure of the product belongs to the triclinic crystal system, and the unit cell parameters are as follows: a=6.0110(2), b=7.5981(3), c= 25.8924(16), α=95.165(4), β=93.167(4), γ=90.031(3).

Example 2

The organic optoelectronic semiconductor material is 2,6-bis(9,10-ditriisopropylsilylethynylanthracenyl)naphthalene, and its structural formula is as follows:

The preparation method of 2,6-bis(9,10-ditriisopropylsilylethynyl anthracenyl)naphthalene 3, comprises the following steps:

2.63 mmol of 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)naphthalene (1 g), 6.05 mmol of 2-bromo-9 , 10-ditriisopropylsilylethynyl anthracene (3.74g) and 0.1315mmol tetrakis(triphenylphosphorus) palladium (152mg) as catalyst were placed in a 100mL three-necked flask, vacuumed and filled with argon three times, and 24mL was added. Toluene and 6mL of potassium carbonate aqueous solution with a concentration of 2M, then the temperature of the reaction system was raised to 90 ° C, Suzuki coupling reaction was carried out, the reaction continued for 24 hours, the reaction system was filtered, and the filter residue was washed with dichloromethane to obtain a crude product, which was used Recrystallization and purification from toluene gave 2.6 g of orange solid as 2,6-bis(9,10-ditriisopropylsilylethynylanthracenyl)naphthalene with a yield of 82%.

Structural confirmation data for this product are shown below:

Hydrogen nuclear magnetic spectrum (CDCl ₃ ): 9.10(2H,d), 8.77(2H,d), 8.66(4H,m), 8.36(2H,d), 8.11(2H,m), 8.06(4H,d), 7.63(4H,m), 131(84H,m);

核磁碳谱(CDCl ₃ )：138.76，138.24，133.27，132.84，132.50，132.20，131.80，128.94，128.12，127.38，127.27，127.01，126.86，126.67，126.15，126.08，125.38，118.97，118.63，105.26，104.89， 103.52, 103.37, 19.10, 11.59;

ESI-MS: m/z=1200.

The reaction process of the present embodiment is as follows:

In Example 2, two reactants for the synthesis of 2,6-bis(9,10-ditriisopropylsilylethynylanthryl)naphthalene: 2,6-bis(4,4,5,5- The preparation method of tetramethyl-1,3,2-dioxaborolane-2-yl)naphthalene and 2-bromo-9,10-ditriisopropylsilylethynyl anthracene is as follows:

The preparation method of 2-bromo-9,10-ditriisopropylsilylethynyl anthracene 1, comprises the following steps:

Under nitrogen protection, 1.5 mL of anhydrous tetrahydrofuran and triisopropylsilyl acetylene (0.52 mL, 2.31 mmol) were added to a three-necked flask equipped with a stirring bar and cooled to -78 °C, and then 3.14 mmol (1.96 mL of ) n-butyllithium (1.6 M hexane solution of n-butyllithium concentration), and stirred for 2 hours to obtain solution A. 8.03 mmol of 2-bromoanthraquinone (2.30 g) was dissolved in 15 ml of anhydrous tetrahydrofuran and added to solution A, followed by stirring at -78°C for 1.5 hours, and then warming up to room temperature of 20-25°C. The reaction was carried out at room temperature for 21 hours, then quenched with water, the resulting intermediate was extracted with chloroform, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The concentrated intermediate product was dissolved in 35 mL of tetrahydrofuran and a mixed solution of stannous chloride (4.54 g, 24 mmol) dissolved in water (20 mL) and glacial acetic acid (3.60 mL, 62.9 mmol) was added dropwise (that is, a mixed solution containing A mixed solution of stannous chloride in water and glacial acetic acid) was stirred at room temperature for 12 hours. After pouring into water, the solid obtained by filtration was washed with ethyl acetate. The filtrate was transferred to a separatory funnel and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel column chromatography (petroleum ether as eluent) afforded 2-bromo-9,10-ditriisopropylsilylethynylanthracene 1 (3.98 g, 6.45 mmol) as a green solid in yield 80%.

The structural confirmation data for this product (2-bromo-9,10-ditriisopropylsilylethynylanthracene) are shown below:

H NMR (CDCl ₃ ): δ8.86(d,1H), 8.60–8.63(m,2H), 8.51(d,1H), 7.62–7.68(m,3H), 1.25–1.33(m,42H, TIPS)ppm;

Carbon NMR (CDCl ₃ ): δ133.5, 132.9, 132.7, 130.9, 129.7, 129.3, 127.7, 127.6, 127.5, 127.4, 121.9, 119.3, 118.1, 105.9, 105.8, 103.0, 19.1, 11.7, 11.7ppm;

High resolution mass spectrum (ESI-MS): m/z=617.2606.

A preparation method for preparing 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)naphthalene 2, comprising the following steps:

2,6-Dibromonaphthalene (0.3 g, 1.05 mmol), pinacol diboronate (0.6 g, 2.5 mmol), [1,1'-bis(diphenylphosphoryl)ferrocene]dichloride Palladium(II) dichloromethane adduct (0.15 g, 0.18 mmol) and potassium acetate (0.6 g, 6.1 mmol) were mixed in a 100 ml two-necked flask, and 1,4- Dioxane (10 mL). The flask was sealed and kept stirring at 80°C for 12 hours. The reaction was quenched by the addition of _H2O (25ml) and the organics were extracted twice with ethyl acetate (20ml each). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by column eluting with 10-30% ethyl acetate in hexanes. The desired product, 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)naphthalene, was isolated as a white solid in yield (0.3 g , 75%).

Structural confirmation data for this product are shown below:

Hydrogen nuclear magnetic spectrum (CDCl ₃ ): 8.35(2H,s), 7.86(2H,d), 7.82(2H,d), 1.38(24H,s)ppm;

Carbon NMR (CDCl ₃ ): 136.13, 134.47, 130.49, 127.83, 127.83, 84.10, 25.07ppm;

ESI-MS: m/z=381.2387.

Example 3

The organic optoelectronic semiconductor material is 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene, and its structural formula is as follows:

A preparation method of 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene, comprising the following steps:

1.55 mmol of 2,6-dibromo-1,5-bis(triisopropylsilylethynyl)naphthalene (1 g), 3.4 mmol of 2-boronic anthracene (755.39 mg) and 0.0775 mmol of tetrakis(triphenylene) as catalyst Palladium (89.56 mg) was placed in a 100 mL three-necked flask, evacuated and filled with argon three times, and 20 mL of toluene and 5 mL of a 2M aqueous potassium carbonate solution were added. After that, the temperature of the reaction system was raised to 90° C., and the Suzuki coupling reaction was carried out, and the reaction was continued for 36 hours. The reaction system was filtered, and the filter residue was washed with dichloromethane to obtain a crude product, which was recrystallized and purified with toluene to obtain 0.9 g of a light green solid as 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl) ) naphthalene 3 in 69.18% yield.

Structural confirmation data for this product are shown below:

Hydrogen nuclear magnetic spectrum (CDCl ₃ ): 8.67(2H,d), 8.48(4H,s), 8.33(2H,s), 8.05(6H,m), 7.88(2H,d), 7.82(2H,d), 7.49(4H,m), 0.99(42H,m);

核磁碳谱(CDCl ₃ )：143.69，138.17，133.41，132.19，132.11，131.72，131.24，131.06，129.24，129.07，128.46，128.11，127.98，127.63，126.98，126.17，125.65，125.52，119.66，101.05，18.57， 11.64;

ESI-MS: m/z=840.

The reaction process of the present embodiment is as follows:

In Example 3, two reactants for the synthesis of 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene 3: 2-boronic anthracene and 2,6-dibromo-1 , The preparation method of 5-bis(triisopropylsilylethynyl)naphthalene 2,2,6-dibromo-1,5-bis(triisopropylsilylethynyl)naphthalene 2 is as follows:

The preparation method of 2,6-dibromo-1,5-bis(triisopropylsilylethynyl)naphthalene 2, comprises the following steps:

2,6-dibromo-1,5-bis(trifluoromethanesulfonate)naphthalene (1 g, 1.72 mmol), bistriphenylphosphine palladium dichloride (60.29 mg, 85.9 mmol) were added to a 100 ml two-necked flask μmol) and cuprous iodide (32.72 mg, 171.8 μmol), and evacuated through argon three times. Then N,N-dimethylformamide (20ml) solution, diisopropylamine (20ml) and triisopropylsilylacetylene (689.33mg, 3.78mmol) were added in sequence, and after stirring at room temperature for 11 hours, water was added 50ml and extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, evaporated to dryness, and purified with silica gel column to obtain a white solid with a yield of 70%.

Structural confirmation data for this product are shown below:

Hydrogen nuclear magnetic spectrum (CDCl ₃ ): 8.19 (d, 2H), 7.73 (d, 2H), 1.21 (d, 42H) ppm;

Carbon NMR spectrum (CDCl ₃ ): 133.35, 131.66, 127.86, 126.08, 123.37, 103.43, 102.51, 18.98, 11.56ppm;

EI-MS: m/z=644.

In the process of preparing 2,6-dibromo-1,5-bis(triisopropylsilylethynyl)naphthalene, the 2,6-dibromo-1,5-bis(trifluoromethanesulfonic acid) used therein The preparation method of ester group) naphthalene 1, comprises the following steps:

2,6-Dibromo-1,5-dihydroxynaphthalene (4.3 g), pyridine (6.5 ml) and dichloromethane (130 ml) were uniformly mixed to obtain a suspension. Trifluoromethanesulfonic anhydride (4.7 mL) was slowly added to the suspension at 0°C. After the addition, the reaction was returned to room temperature of 20-25°C, and the reaction state was monitored with a silica gel plate. After the reaction, 100 ml of water was added, extracted with dichloromethane, dried over anhydrous magnesium sulfate, evaporated to dryness, and the crude product was purified by silica gel column to obtain a white solid with a yield of 80%.

Structural confirmation data for this product are shown below:

Hydrogen nuclear magnetic spectrum (CDCl ₃ ): 7.89 (d, 2H), 8.03 (d, 2H) ppm;

Carbon NMR spectrum (CDCl ₃ ): 116.8, 118.8, 123.0, 128.8, 133.3, 142.7ppm;

EI-MS: m/z=580.

The present invention has been exemplarily described above. It should be noted that, without departing from the core of the present invention, any simple deformation, modification, or other equivalent replacements that can be performed by those skilled in the art without any creative effort fall into the scope of the present invention. The scope of protection of the invention.

Claims (10)

1. an organic photoelectric semiconductor material, its structural formula is as follows: Wherein, R ₁ is hydrogen or triisopropylsilyl acetylene, R ₂ is hydrogen or triisopropylsilyl acetylene, and the organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, 2,6-bis( 9,10-Ditriisopropylsilylethynylanthryl)naphthalene or 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene. 2. the preparation method of organic photoelectric semiconductor material as claimed in claim 1 is characterized in that, comprises the following steps: Under inert gas environment, reactant A, reactant B, tetrakis (triphenylphosphonium) palladium as catalyst, toluene and potassium carbonate aqueous solution are uniformly mixed, and after mixing, the temperature is raised to 90～100 ℃ and reacted for 24～96 hours, and filtered. The filter residue is obtained, and the filter residue is washed with a detergent to obtain the organic optoelectronic semiconductor material, wherein the ratio of the substance amount of the reactant A and the reactant B is (2.1-2.4): 1, the volume of the toluene The ratio of the parts, the amount of the reactant B and the amount of the potassium carbonate in the potassium carbonate aqueous solution is (9-15): 1: (4-15); When the organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, the reactant A is 2-boronic acid anthracene, and the reactant B is 2,6-dibromonaphthalene; When the organic optoelectronic semiconductor material is 2,6-bis(9,10-ditriisopropylsilylethynylanthracenyl)naphthalene, the reactant A is 2-bromo-9,10-ditriiso propylsilylethynyl anthracene, the reactant B is 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) Naphthalene; When the organic optoelectronic semiconductor material is 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene, the reactant A is 2-boronic acid anthracene, and the reactant B is 2,6-Dibromo-1,5-bis(triisopropylsilylethynyl)naphthalene. 3 . The preparation method according to claim 2 , wherein when the organic optoelectronic semiconductor material is 2,6-dianthracene naphthalene, the ratio of the amount of the reactant A and the amount of the reactant B is: 3 . (2.1 to 2.2): 1. 4. The preparation method according to claim 2, wherein when the organic optoelectronic semiconductor material is 2,6-bis(9,10-ditriisopropylsilylethynylanthracenyl)naphthalene, the The ratio of the amount of the reactant A and the reactant B is (2.2-2.4):1. The preparation method according to claim 2, wherein when the organic optoelectronic semiconductor material is 2,6-dianthracene-1,5-bis(triisopropylsilylethynyl)naphthalene, the The ratio of the amount of the reactant A and the reactant B is (2.1-2.2):1. 6 . The preparation method according to claim 3 , wherein the ratio of the reactant B to the catalyst is 1: (0.05˜0.1) in terms of the amount of substance. 7 . 7. preparation method according to claim 6 is characterized in that, in the described potassium carbonate aqueous solution, the concentration of potassium carbonate is 2M, the unit of volume fraction is mL, and the unit of material fraction is mmol. 8. The preparation method according to claim 7, wherein the inert gas is argon or nitrogen. 9. The application of the preparation method according to claims 2 to 8 in the preparation of the organic optoelectronic semiconductor material. 10 . The use according to claim 9 , wherein the yield of the preparation method is 69-89%. 11 .