CN110627601A - Organic photoelectric semiconductor material and preparation method and application thereof - Google Patents
Organic photoelectric semiconductor material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an organic photoelectric semiconductor material and a preparation method and application thereof, wherein the organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, 2, 6-bis (9, 10-triisopropylsilylethynyl anthracene group) naphthalene or 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl group) naphthalene. The preparation method of the organic photoelectric semiconductor material comprises the following steps: in an inert gas environment, uniformly mixing a reactant A, a reactant B, palladium tetrakis (triphenylphosphine) as a catalyst, toluene and a potassium carbonate aqueous solution, heating to 90-100 ℃ after mixing, reacting for 24-96 hours, filtering to obtain filter residues, and washing the filter residues with a detergent to obtain the organic photoelectric semiconductor material, wherein the preparation reaction route provided by the invention has the advantages of simplicity, high efficiency, environmental friendliness, low raw material price and low synthesis cost; the method has high universality and good repeatability; the invention provides a new choice for high-performance organic photoelectric materials.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric semiconductor materials, and particularly relates to an organic photoelectric semiconductor material and a preparation method and application thereof.
Background
Organic semiconductor devices such as organic solar cells (OPVs), Organic Light Emitting Diodes (OLEDs), Organic Electrochromism (OECs), and Organic Thin Film Transistors (OTFTs) have been developed and applied in many fields. In all these organic photoelectric fields, organic photoelectric materials are key. The organic semiconductor material which is designed and synthesized and has simple process, lower cost, stable material performance and long service life so as to achieve the purpose of commercialization has wide application prospect.
The condensed ring acene material is an organic material with good photoelectric property. For example, the single crystal mobility of pentacene has reached 15-40cm2V-1s-1. Anthracene is the smallest member of the acene family with transistor properties and has better luminescence and device performance. In general, increasing conjugation can increase the combination of transfer integration and decreasing recombination energy resulting in higher charge carrier mobility. Therefore, naphthalene ring is added in the middle of the anthracene ring, so that conjugation is increased, and luminescence of anthracene is maintained.
Although a large number of organic semiconductor materials have been designed and synthesized, there are not many materials that have high fluorescence quantum efficiency and high mobility. However, such materials are critical in the preparation of OLETs and OLEDs. The preparation of such materials is of great importance.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic photoelectric semiconductor material, the invention also aims to provide a preparation method of the organic photoelectric semiconductor material, and the invention also aims to provide application of the preparation method in preparing the organic photoelectric semiconductor material.
The purpose of the invention is realized by the following technical scheme.
An organic photoelectric semiconductor material has a structural formula as follows:
wherein R is1Is hydrogen or triisopropylsilylacetylene, R2The organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, 2, 6-bis (9, 10-triisopropylsilylethynyl anthracene) naphthalene or 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene.
The preparation method of the organic photoelectric semiconductor material comprises the following steps:
uniformly mixing a reactant A, a reactant B, tetrakis (triphenylphosphine) palladium as a catalyst, toluene and a potassium carbonate aqueous solution in an inert gas environment, heating to 90-100 ℃ after mixing, reacting for 24-96 hours, filtering to obtain filter residue, and washing the filter residue with a detergent to obtain the organic photoelectric semiconductor material, wherein the mass ratio of the reactant A to the reactant B is (2.1-2.4): 1, the ratio of the volume parts of the toluene, the mass parts of the reactant B and the mass parts of the potassium carbonate in the potassium carbonate aqueous solution is (9-15): 1: (4-15);
when the organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, the reactant A is 2-anthracene borate, and the reactant B is 2, 6-dibromo naphthalene;
when the organic photoelectric semiconductor material is 2, 6-bis (9, 10-triisopropylsilylethynyl anthracene base) naphthalene, the reactant A is 2-bromo-9, 10-triisopropylsilylethynyl anthracene, and the reactant B is 2, 6-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalene;
when the organic photoelectric semiconductor material is 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene, the reactant A is 2-anthracene borate, and the reactant B is 2, 6-dibromo-1, 5-bis (triisopropylsilylethynyl) naphthalene.
In the above technical solution, when the organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, the ratio of the amounts of the reactant a and the reactant B is (2.1-2.2): 1.
when the organic photoelectric semiconductor material is 2, 6-bis (9, 10-triisopropylsilylethynyl anthracenyl) naphthalene, the ratio of the amounts of the reactant A and the reactant B is (2.2-2.4): 1.
when the organic photoelectric semiconductor material is 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene, the ratio of the amounts of the reactant A and the reactant B is (2.1-2.2): 1.
in the above technical solution, the ratio of the reactant B to the catalyst is 1: (0.05-0.1).
In the above technical scheme, the concentration of potassium carbonate in the potassium carbonate aqueous solution is 2M.
In the above technical scheme, the inert gas is argon or nitrogen.
In the technical scheme, the unit of volume parts is mL, and the unit of mass parts is mmol.
The preparation method is applied to the preparation of the organic photoelectric semiconductor material.
In the technical scheme, the yield of the preparation method is 69-89%.
Compared with the prior art, the invention has the following beneficial effects:
the preparation reaction route provided by the invention has the advantages of simplicity, high efficiency, environmental friendliness, low raw material price and low synthesis cost; the method has high universality and good repeatability;
the invention provides a new choice for high-performance organic photoelectric materials.
Drawings
FIG. 1 is a UV-VIS absorption spectrum of 2, 6-dianthracene naphthalene in solid state prepared in example 1;
FIG. 2 is a UPS plot of 2, 6-dianthracene naphthalene prepared in example 1;
FIG. 3 is a TGA curve of 2, 6-dianthracene naphthalene prepared in example 1;
FIG. 4 is a schematic structural diagram of an organic field effect transistor;
FIG. 5(a) is a typical transfer curve for OFETs prepared from 2, 6-dianthracene naphthalene prepared in example 1;
FIG. 5(b) is a graph of the output of OFETs prepared from 2, 6-dianthracene naphthalene prepared in example 1;
FIG. 6 shows the single crystal structure of 2, 6-dianthracene naphthalene prepared in example 1.
Detailed Description
The technical scheme of the invention is further explained by combining specific examples.
The following examples relate to pharmaceutical products as purchasers and purities as follows:
the following examples relate to the apparatus and models for the test characterization as follows:
nuclear magnetism: BRUKER AVANCE III
Mass spectrum: APEX II type Fourier transform ion cyclotron resonance mass spectrometer (FT-ICR-MS)
Elemental analysis: FLASH EA1112 element analyzer
Ultraviolet: UV2600 ultraviolet visible spectrophotometer
UPS test: ESCLAb 250Xi multifunctional X-ray photoelectron spectrometer
And (3) thermogravimetric testing: thermal Analysis Excellence TGA 2
And (3) testing a device: keithley 4200-scs
Crystal resolution: XtalaBmini, Inc. of society
Example 1
The organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, and the structural formula is as follows:
the preparation method of the organic photoelectric 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 (triphenylphosphine) palladium (202mg) as a catalyst were placed in a 250mL three-necked flask, vacuum-pumping and argon-charging were carried out three times, 50mL of toluene and 25mL of a 2M aqueous solution of potassium carbonate were added, and then the temperature of the reaction system was raised to 90 ℃ to carry out a Suzuki coupling reaction for 96 hours. Filtering the reaction system, washing the filter residue with triethylamine and dichloromethane in sequence to obtain a crude product, and carrying out sublimation purification to obtain 1.5g of yellow solid which is the organic photoelectric semiconductor material, wherein the yield is 89%.
The reaction procedure of this example is as follows:
the structural confirmation data for this product are shown below:
EI-MS：480；
elemental analysis: carbon: 94.98%, hydrogen: 4.97 percent.
The yellow solid product has a correct structure, namely 2, 6-dianthracene naphthalene, according to the elementary analysis.
Spectral properties, UPS test, thermodynamic properties, and properties of organic field effect transistors of 2, 6-dianthracene naphthalene obtained in example 1 were determined as follows:
1) spectral properties of organic 2, 6-dianthracene naphthalene
FIG. 1 shows the UV-VIS absorption spectrum of 2, 6-dianthracene naphthalene in the solid state. As can be seen from fig. 1, the peak of the maximum absorption side band of 2, 6-dianthracene naphthalene in the solid state is 466nm, and the corresponding optical band gap is 2.66eV (the optical band gap is calculated according to the formula Eg 1240/λ, where Eg is the optical band gap and λ is the boundary value of the ultraviolet absorption curve).
2) UPS test of organic 2, 6-dianthracene naphthalene
The UV light source used was non-monochromatized He I, the energy of the He I light source used was 21.22eV, and the base vacuum of the analysis chamber during the UPS analysis test of the apparatus was 3.0X10-8Torr, in the test procedureThe bias voltage applied was-9V. A sample (2, 6-dianthracene naphthalene) was evaporated under vacuum onto a silicon wafer of about 10mm by 10mm (1cm by 1cm) to a thickness of about 15 nm.
FIG. 2 is a UPS curve of 2, 6-dianthracene naphthalene, and from FIG. 2, it can be calculated that the ionization potential of 2, 6-dianthracene naphthalene is-5.42 eV, that is, the HOMO value with respect to the vacuum level is-5.42 eV. The 2, 6-dianthracene naphthalene is shown to have high oxidation stability and good hole injection capability.
3) Thermodynamic properties of organic 2, 6-dianthracene naphthalene
FIG. 3 is a TGA curve of 2, 6-dianthracene naphthalene as a material, and it can be seen that 2, 6-dianthracene naphthalene shows excellent thermal stability and the decomposition temperature of thermal weight loss is 430 ℃.
4) Field effect transistor properties of organic 2, 6-dianthracene naphthalene
FIG. 4 is a schematic view of the structure of an organic field effect transistor, as shown in FIG. 4, 1 is Si/SiO2The substrate, Si as a gate electrode, 2 as an OTS (octadecyltrichlorosilane) modified SiO2 as an insulating layer, 3 as a semiconductor micro-nano crystal layer of 2, 6-dianthracene naphthalene, and 4 and 5 as Au source and drain electrodes respectively. The whole device adopts a bottom gate top contact configuration, namely the structure of the device is Si (500 mu m)/SiO2(300nm)/OTS (monomolecular layer)/2, 6-dianthranthracene micro-nano crystal/Au.
The transition curve (fig. 5(a)) and the output curve (fig. 5(b)) of the 2, 6-dianthracene naphthalene micro-nano single crystal field effect transistor are shown in fig. 5. Equation (i) is calculated using the following saturation region, and the mobility μ is calculated:
from FIG. 5 and the above saturation equation (I), it can be seen that: at VG<-5V, the linear field effect transistor device operating in the saturation region, ISDThere is little change; when V isG>at-5V, the linear FET device operates in the linear region, ISDLinearly changing. The mobility of the 2, 6-dianthracene naphthalene is calculated to be 19.6cm2V-1s-1. (the mobility is calculated by the method described inAirport effect transistor chapter 2 organic field effect transistor, section 2 organic field effect transistor, the authors: huwenping, press: scientific press, ISBN 9787030320629. )
FIG. 6 shows the single crystal structure of 2, 6-dianthracene naphthalene as an organic substance, which belongs to the triclinic system and has the following unit cell parameters: 6.0110(2), 7.5981(3), 25.8924(16), 95.165(4), 93.167(4), and 90.031 (3).
Example 2
The organic photoelectric semiconductor material is 2, 6-bis (9, 10-triisopropylsilylethynyl anthracenyl) naphthalene, and the structural formula is as follows:
the preparation method of 2, 6-bis (9, 10-triisopropylsilylethynyl anthracenyl) naphthalene 3 comprises the following steps:
2.63mmol of 2, 6-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalene (1g), 6.05mmol of 2-bromo-9, 10-triisopropylsilylethynylanthracene (3.74g) and 0.1315mmol of tetrakis (triphenylphosphine) palladium (152mg) as a catalyst were placed in a 100mL three-necked flask, vacuumizing and filling argon for three times, adding 24mL of toluene and 6mL of 2M potassium carbonate aqueous solution, raising the temperature of a reaction system to 90 ℃, carrying out Suzuki coupling reaction for 24 hours, the reaction system was filtered, and the residue was washed with dichloromethane to obtain a crude product, which was recrystallized from toluene to obtain 2.6g of 2, 6-bis (9, 10-triisopropylsilylethynylanthracenyl) naphthalene as an orange solid in a yield of 82%.
The structural confirmation data for this product are shown below:
nuclear magnetic hydrogen 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)；
Nuclear magnetic carbon spectrum (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 procedure of this example is as follows:
in example 2, two reactants of 2, 6-bis (9, 10-triisopropylsilylethynyl anthracenyl) naphthalene were synthesized: the preparation methods of 2, 6-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalene and 2-bromo-9, 10-triisopropylsilylethynyl anthracene are as follows:
the preparation method of the 2-bromo-9, 10-triisopropylsilylethynyl anthracene 1 comprises the following steps:
1.5mL of anhydrous tetrahydrofuran and triisopropylsilylacetylene (0.52mL, 2.31mmol) were added to a three-necked flask equipped with a stirrer under nitrogen atmosphere, cooled to-78 deg.C, and 3.14mmol (1.96mL) of n-butyllithium (a 1.6M solution of n-butyllithium in hexane) was added and stirred for 2 hours to obtain a solution A. 8.03mmol of 2-bromoanthraquinone (2.30g) was dissolved in 15ml of anhydrous tetrahydrofuran and added to the solution A, followed by stirring at-78 ℃ for 1.5 hours and then warming to room temperature of 20 to 25 ℃. The reaction was allowed to proceed at room temperature for 21 hours, then quenched with water, the resulting intermediate was extracted with chloroform, and the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The concentrated intermediate was dissolved in 35mL of tetrahydrofuran and a mixed solution of stannous chloride (4.54g, 24mmol) dissolved in water (20mL) and glacial acetic acid (3.60mL, 62.9mmol) (i.e., a mixed solution of water containing stannous chloride and glacial acetic acid was added dropwise) and 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) gave 2-bromo-9, 10-triisopropylsilylethynyl anthracene 1(3.98g, 6.45mmol) as a green solid in 80% yield.
The structure confirmation data of this product (2-bromo-9, 10-triisopropylsilylethynyl anthracene) is as follows:
nuclear magnetic hydrogen spectrum (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；
Nuclear magnetic carbon spectrum (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 spectrometry (ESI-MS) with m/z 617.2606.
A process for preparing 2, 6-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalene 2 comprising the steps of:
2, 6-dibromonaphthalene (0.3g, 1.05mmol), pinacol diboron (0.6g, 2.5mmol) and [1, 1' -bis (diphenylphosphino) ferrocene]Palladium (II) dichloride dichloromethane adduct (0.15g, 0.18mmol) and potassium acetate (0.6g, 6.1mmol) were mixed in a 100mL two-necked flask, and 1, 4-dioxane (10mL) bubbled in advance for 30 minutes was added under a nitrogen atmosphere. The flask was sealed and kept stirring at 80 ℃ for 12 hours. By addition of H2The reaction was quenched with O (25ml) and the organics extracted 2 times with ethyl acetate (20ml each). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by column and eluted with 10-30% ethyl acetate in hexane. The desired product, 2, 6-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalene, was isolated as a white solid in yield (0.3g, 75%).
The structural confirmation data for this product are shown below:
nuclear magnetic hydrogen spectrum (CDCl)3)：8.35(2H,s)，7.86(2H,d)，7.82(2H,d)，1.38(24H,s)ppm；
Nuclear magnetic carbon spectrum (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 photoelectric semiconductor material is 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene, and the structural formula is as follows:
the preparation method of 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene comprises the following steps:
1.55mmol of 2, 6-dibromo-1, 5-bis (triisopropylsilylethynyl) naphthalene (1g), 3.4mmol of 2-boronic acid anthracene (755.39mg), and 0.0775mmol of tetrakis (triphenylphosphine) palladium (89.56mg) as a catalyst were placed in a 100mL three-necked flask, vacuum-charged three times with argon, and 20mL of toluene and 5mL of a 2M aqueous solution of potassium carbonate were added. Then, the temperature of the reaction system is raised to 90 ℃, and the Suzuki coupling reaction is carried out for 36 hours. The reaction system was filtered, and the residue was washed with dichloromethane to obtain a crude product, which was recrystallized from toluene to obtain 0.9g of a pale green solid 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene 3 with a yield of 69.18%.
The structural confirmation data for this product are shown below:
nuclear magnetic hydrogen 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)；
Nuclear magnetic carbon spectrum (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 procedure of this example is as follows:
in example 3, two reactants of 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene 3 were synthesized: the preparation methods of 2-anthracene borate and 2, 6-dibromo-1, 5-bis (triisopropylsilylethynyl) naphthalene 2, 2, 6-dibromo-1, 5-bis (triisopropylsilylethynyl) naphthalene 2 are as follows:
the preparation method of 2, 6-dibromo-1, 5-bis (triisopropylsilylethynyl) naphthalene 2 comprises the following steps:
to a 100ml two-necked flask were added 2, 6-dibromo-1, 5-bis (trifluoromethanesulfonate) naphthalene (1g, 1.72mmol), bis triphenylphosphine palladium dichloride (60.29mg, 85.9. mu. mol), and cuprous iodide (32.72mg, 171.8. mu. mol), and the mixture was evacuated and circulated with argon three times. Then, N-dimethylformamide (20ml) solution, diisopropylamine (20ml) and triisopropylsilylacetylene (689.33mg, 3.78mmol) were sequentially added thereto, and after stirring at room temperature for 11 hours, water (50 ml) was added and extraction was performed with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate and the solvent was evaporated to dryness, and purification was performed with a silica gel column to obtain a white solid with a yield of 70%.
The structural confirmation data for this product are shown below:
nuclear magnetic hydrogen spectrum (CDCl)3)：8.19(d，2H),7.73(d，2H),1.21(d，42H)ppm；
Nuclear magnetic carbon 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 preparation method of 2, 6-dibromo-1, 5-bis (trifluoromethanesulfonate) naphthalene 1 used therein comprises the following steps:
2, 6-dibromo-1, 5-dihydroxynaphthalene (4.3g), pyridine (6.5ml) and methylene chloride (130ml) were uniformly mixed to obtain a suspension. At 0 ℃, trifluoromethanesulfonic anhydride (4.7mL) was slowly added to the suspension, and after the addition was complete, the reaction was returned to room temperature of 20-25 ℃ and the reaction state was monitored with a silica gel plate. After the reaction, 100ml of water was added, and the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and the solvent was evaporated to dryness, and the crude product was purified by a silica gel column to obtain a white solid with a yield of 80%.
The structural confirmation data for this product are shown below:
nuclear magnetic hydrogen spectrum (CDCl)3)：7.89(d,2H),8.03(d,2H)ppm；
Nuclear magnetic carbon spectrum (CDCl)3)：116.8，118.8，123.0，128.8，133.3，142.7ppm；
EI-MS:m/z＝580。
The invention has been described in an illustrative manner, and it is to be understood that any simple variations, modifications or other equivalent changes which can be made by one skilled in the art without departing from the spirit of the invention fall within the scope of the invention.
Claims (10)
1. An organic photoelectric semiconductor material has a structural formula as follows:
wherein R is1Is hydrogen or triisopropylsilylacetylene, R2The organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, 2, 6-bis (9, 10-triisopropylsilylethynyl anthracene) naphthalene or 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene.
2. The method for producing an organic photoelectric semiconductor material according to claim 1, comprising the steps of:
uniformly mixing a reactant A, a reactant B, tetrakis (triphenylphosphine) palladium as a catalyst, toluene and a potassium carbonate aqueous solution in an inert gas environment, heating to 90-100 ℃ after mixing, reacting for 24-96 hours, filtering to obtain filter residue, and washing the filter residue with a detergent to obtain the organic photoelectric semiconductor material, wherein the mass ratio of the reactant A to the reactant B is (2.1-2.4): 1, the ratio of the volume parts of the toluene, the mass parts of the reactant B and the mass parts of the potassium carbonate in the potassium carbonate aqueous solution is (9-15): 1: (4-15);
when the organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, the reactant A is 2-anthracene borate, and the reactant B is 2, 6-dibromo naphthalene;
when the organic photoelectric semiconductor material is 2, 6-bis (9, 10-triisopropylsilylethynyl anthracene base) naphthalene, the reactant A is 2-bromo-9, 10-triisopropylsilylethynyl anthracene, and the reactant B is 2, 6-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) naphthalene;
when the organic photoelectric semiconductor material is 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene, the reactant A is 2-anthracene borate, and the reactant B is 2, 6-dibromo-1, 5-bis (triisopropylsilylethynyl) naphthalene.
3. The method according to claim 2, wherein when the organic photoelectric semiconductor material is 2, 6-dianthracene naphthalene, the ratio of the amounts of the reactant A and the reactant B is (2.1-2.2): 1.
4. the method according to claim 2, wherein when the organic photoelectric semiconductor material is 2, 6-bis (9, 10-triisopropylsilylethynyl anthracenyl) naphthalene, the ratio of the amounts of the substances of the reactant A and the reactant B is (2.2-2.4): 1.
5. the production method according to claim 2, wherein when the organic photoelectric semiconductor material is 2, 6-dianthracene-1, 5-bis (triisopropylsilylethynyl) naphthalene, the ratio of the amounts of the substances of the reactant A and the reactant B is (2.1 to 2.2): 1.
6. the method of claim 3 or 4 or 5, wherein the ratio of the reactant B to the catalyst is 1: (0.05-0.1).
7. The preparation method according to claim 6, wherein the concentration of potassium carbonate in the aqueous potassium carbonate solution is 2M, the unit of volume fraction is mL, and the unit of mass fraction is mmol.
8. The method of claim 7, wherein the inert gas is argon or nitrogen.
9. The use of the preparation method according to claims 2 to 8 for preparing the organic optoelectronic semiconductor material.
10. The use according to claim 9, wherein the preparation process has a yield of 69 to 89%.
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