A circularly polarized luminescent material, its method and application

Abstract

The present invention relates to the technical field of organic materials, and provides a circularly polarized luminescent material, a method thereof, and an application. The circularly polarized luminescent material is a compound having the structure of Formula I: #imgabs0# The circularly polarized luminescent material of the present invention has good luminescent properties and high luminescent efficiency.

Description

Technical Field

[0001] The present invention relates to the technical field of organic materials, and particularly relates to a circularly polarized luminescent material, a method thereof, and an application thereof. Background Art

[0002] In recent years, optical materials with circularly polarized luminescence properties have received extensive attention due to their potential in various fields. However, traditional molecules with a planar chiral columnar pentaaryl skeleton have poor luminescence properties (such as low luminescence efficiency). Summary of the Invention

[0003] Aiming at the above deficiencies existing in the prior art, the purpose of the present invention is to provide a circularly polarized luminescent material, a method thereof, and an application thereof, and the circularly polarized luminescent material has a high luminescence efficiency.

[0004] To achieve the above invention purpose, the technical solution adopted by the present invention is as follows:

[0005] In the first aspect, an embodiment of the present invention provides a compound having a structure of formula Ⅰ:

[0006]

[0007] The compound having a structure of formula Ⅰ provided by the embodiment of the present invention uses columnar pentaaryl as the basic unit as the chiral source (chiral skeleton molecule), and modifies the chiral skeleton molecule by introducing a boron-nitrogen Lewis acid-base pair, which can well inhibit the racemization of enantiomers caused by the flipping of the benzene ring in the chiral skeleton molecule, thereby obtaining enantiomers with stable configurations; at the same time, the introduced boron-nitrogen Lewis acid-base pair has excellent luminescence and multiple stimulus response properties, which is beneficial to improving the luminescence properties (such as luminescence efficiency) of the material.

[0008] In the second aspect, an embodiment of the present invention provides a preparation method of a compound having a structure of formula Ⅰ, including the following steps:

[0009]

[0010]

[0011]

[0012] S1. Synthesis of compound Ⅲ:

[0013] The compound Ⅱ having a structure of formula Ⅱ reacts with paraformaldehyde and boron trifluoride diethyl ether in a first solvent to obtain a compound Ⅲ having a structure of formula Ⅲ;

[0014] S2. Synthesis of compound Ⅳ:

[0015] The compound Ⅲ with the structure of formula Ⅲ reacts with ammonium cerium nitrate in a second solvent to obtain the compound Ⅳ with the structure of formula Ⅳ;

[0016] S3. Synthesis of compound Ⅴ:

[0017] The compound Ⅳ with the structure of formula Ⅳ reacts with sodium dithionite in a third solvent to obtain the compound Ⅴ with the structure of formula Ⅴ;

[0018] S4. Synthesis of compound Ⅵ:

[0019] The compound Ⅴ with the structure of formula Ⅴ reacts with pyridine and trifluoromethanesulfonic anhydride in a fourth solvent to obtain the compound Ⅵ with the structure of formula Ⅵ;

[0020] S5. Synthesis of compound Ⅷ:

[0021] The compound Ⅵ with the structure of formula Ⅵ reacts with the compound Ⅶ with the structure of formula Ⅶ in a fifth solvent in the presence of a catalyst and a first base to obtain the compound Ⅷ with the structure of formula Ⅷ;

[0022] S6. Synthesis of compound Ⅸ:

[0023] The compound Ⅷ with the structure of formula Ⅷ reacts with 2-bromobenzyl bromide in a sixth solvent in the presence of a second base to obtain the compound Ⅸ with the structure of formula Ⅸ;

[0024] S7. Synthesis of compound Ⅰ:

[0025] The compound Ⅸ with the structure of formula Ⅸ reacts with n-butyllithium and MesB(OMe)2 in a seventh solvent to obtain the compound Ⅰ with the structure of formula Ⅰ.

[0026] The preparation method provided by the embodiments of the present invention is simple, with mild conditions, convenient operation, low requirements for equipment conditions, extremely easy to implement, and simple post-treatment, and is suitable for industrial large-scale production.

[0027] In a third aspect, the embodiments of the present invention provide an application of the compound with the structure of formula Ⅰ in the preparation of optical sensors and optoelectronic devices.

[0028] The compound with the structure of formula Ⅰ provided by the embodiments of the present invention has good luminescence properties and high luminescence efficiency, can be used in the preparation of optical sensors and optoelectronic devices, and can also be applied in fields such as information anti-counterfeiting and encryption. Description of the Drawings

[0029] To more clearly illustrate the technical solutions in the embodiments of the present invention, the following will briefly introduce the accompanying drawings required in the description of the embodiments or the prior art. Obviously, the accompanying drawings in the following description are only some embodiments of the present invention. For those of ordinary skill in the art, without creative efforts, other accompanying drawings can be obtained based on these drawings.

[0030] Figure 1 is the proton nuclear magnetic resonance spectrum of Compound I prepared in Example 1 of the present invention;

[0031] Figure 2 is the high performance liquid chromatography chart of Compound Ⅰ prepared in Example 1 of the present invention;

[0032] Figure 3 is the fluorescence spectrum chart of Compound Ⅰ prepared in Example 1 of the present invention under different solvents;

[0033] Figure 4 is the ultraviolet-visible absorption spectrum chart of Compound Ⅰ prepared in Example 1 of the present invention under different solvents. Detailed implementation manners

[0034] In order to make the technical problems to be solved, technical solutions and beneficial effects of the present invention more clearly understood, the following further details the present invention in combination with embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention, but the implementation manners of the present invention are not limited thereto.

[0035] Unless otherwise defined, the technical terms used in the following embodiments have the same meanings as commonly understood by those skilled in the art to which the present invention belongs. The experimental reagents used in the following embodiments are all conventional biochemical reagents unless otherwise specified; the amounts of the experimental reagents used are all the amounts of reagents in conventional experimental operations unless otherwise specified; the experimental methods used are all conventional methods unless otherwise specified.

[0036] In the first aspect, the embodiments of the present invention provide a compound having the structure of Formula Ⅰ:

[0037]

[0038] Pillar[5]arenes (pillar pentarenes) and pillar[n]arenes have cavity structures related to their sizes. They are a unique class of macrocycles with inherent planar chirality and are typical representatives of the new generation of supramolecular macrocycle hosts. However, at room temperature, the benzene rings in pillar[5]arenes (pillar pentarenes) and pillar[n]arenes are prone to flipping, resulting in the racemization of enantiomers. Boron atoms are located in Group III of the second period in the periodic table of chemical elements. It is the only non-metal element in Group III. It rarely exists in the form of simple substances in nature and mainly exists in the form of covalent bonds with oxygen atoms (such as boric acid, borates, etc.). The nuclear outer electron configuration of boron atoms is 1s 2 2s 2 2p 1 , From its nuclear outer electron configuration, it can be seen that boron atoms have empty p orbitals, which endows boron atoms with unique structural and electronic properties.

[0039] The compound with the structure of Formula I provided by the embodiments of the present invention uses pillar pentarene as the basic unit as the chiral source (chiral skeleton molecule), and modifies the chiral skeleton molecule by introducing a boron-nitrogen Lewis acid-base pair, which can well inhibit the flipping of the benzene ring in the chiral skeleton molecule, resulting in the racemization of enantiomers, thereby obtaining enantiomers with stable configurations; at the same time, the introduced boron-nitrogen Lewis acid-base pair (an excellent fluorescent group) has excellent luminescence and multiple stimulus response properties, which is beneficial to improving the luminescence performance of the material (such as luminescence efficiency).

[0040] Second, the embodiments of the present invention provide a preparation method of a compound with the structure of Formula I, including the following steps:

[0041]

[0042]

[0043]

[0044] S1. Synthesis of Compound III:

[0045] The compound II with the structure of Formula II reacts with paraformaldehyde and boron trifluoride diethyl ether in a first solvent to obtain a compound III with the structure of Formula III;

[0046] S2. Synthesis of Compound IV:

[0047] The compound III with the structure of Formula III reacts with ammonium cerium nitrate in a second solvent to obtain a compound IV with the structure of Formula IV;

[0048] S3. Synthesis of Compound V:

[0049] The compound Ⅳ with the structure of formula Ⅳ reacts with sodium dithionite in a third solvent to obtain the compound Ⅴ with the structure of formula Ⅴ;

[0050] S4. Synthesis of compound Ⅵ:

[0051] The compound Ⅴ with the structure of formula Ⅴ reacts with pyridine and trifluoromethanesulfonic anhydride in a fourth solvent to obtain the compound Ⅵ with the structure of formula Ⅵ;

[0052] S5. Synthesis of compound Ⅷ:

[0053] The compound Ⅵ with the structure of formula Ⅵ reacts with the compound Ⅶ with the structure of formula Ⅶ in a fifth solvent in the presence of a catalyst and a first base to obtain the compound Ⅷ with the structure of formula Ⅷ;

[0054] S6. Synthesis of compound Ⅸ:

[0055] The compound Ⅷ with the structure of formula Ⅷ reacts with 2-bromobenzyl bromide in a sixth solvent in the presence of a second base to obtain the compound Ⅸ with the structure of formula Ⅸ;

[0056] S7. Synthesis of compound Ⅰ:

[0057] The compound Ⅸ with the structure of formula Ⅸ reacts with n-butyllithium and MesB(OMe)2 in a seventh solvent to obtain the compound Ⅰ with the structure of formula Ⅰ.

[0058] The preparation method provided by the embodiments of the present invention is simple, with mild conditions, convenient operation, low requirements for equipment conditions, extremely easy to implement, and simple post-treatment, and is suitable for large-scale industrial production.

[0059] Further, in step S1, the first solvent is at least one of dichloromethane and chloroform. The reaction temperature is 0 °C. During the reaction, it is necessary to strictly control the use of anhydrous solvent, otherwise the yield of compound Ⅲ will be very low; secondly, the reaction time is controlled at about 30 min, such as 30 min. When the reaction time is too long, polymers are likely to be generated and the target product (compound Ⅲ) cannot be obtained.

[0060] Further, in step S2, the second solvent is a mixture of dichloromethane and water. The volume ratio of dichloromethane to water in this mixture is 10:1. In this step, the reaction is controlled at room temperature for 1 to 1.5 hours, and the reaction ends when the solution turns wine red. If the reaction time is too long or too short, the yield of the product will decrease.

[0061] Further, in step S3, the third solvent is a mixture of dichloromethane and water. The volume ratio of dichloromethane to water in this mixture is 10:1. In this step, the reaction is controlled at room temperature, and an anaerobic atmosphere should be maintained as much as possible during the reaction, because when the oxygen content is too high, a large amount of by-products will be generated, resulting in a decrease in yield.

[0062] Further, in step S4, the fourth solvent is dichloromethane. In this step, the reaction temperature is controlled at 0 °C, and an anhydrous and anaerobic atmosphere is maintained during the reaction, otherwise the yield will decrease.

[0063] Further, in step S5, the catalyst is a palladium catalyst; the first base is potassium carbonate; the fifth solvent is a mixture of tetrahydrofuran and water, or a mixture of toluene, ethanol and water. The volume ratio of tetrahydrofuran to water in this mixture is 5:1, or the volume ratio of toluene, ethanol to water is 6:1:1. In this step, the reaction temperature is controlled at 70 °C, and the reaction should be kept in an anaerobic environment to ensure the catalytic effect of the palladium catalyst. When there is oxygen in the reaction system, the reaction fails and no product is formed.

[0064] In step S5, the synthesis step of compound VII is as follows: 4-bromo-2,6-dimethylaniline reacts in 1,4-dioxane in the presence of a palladium catalyst to obtain compound VII having formula VII.

[0065] Further, in step S6, the second base is sodium hydroxide; the sixth solvent is a mixture of tetrahydrofuran and water. The volume ratio of tetrahydrofuran to water in this mixture is 6:1. In this step, the reaction temperature is controlled at 70 °C, and the reaction time should be controlled at 20 h or more. When the reaction time is too short, the yield is extremely low.

[0066] Further, in step S7, the seventh solvent is at least one of tetrahydrofuran and diethyl ether. In this step, the reaction temperature is controlled at -78 °C, and the reaction should be kept in an anhydrous and anaerobic atmosphere. At the same time, all solvents should be anhydrous solvents. When there is water in the reaction system, the reaction fails.

[0067] Compound IX itself has only weak fluorescence. By introducing the MesB group into compound IX, compound I can have good fluorescence properties.

[0068] Thirdly, the embodiments of the present invention provide the application of the compound having the structure of formula I in the preparation of optical sensors and optoelectronic devices.

[0069] The compound having the structure of formula I provided by the embodiments of the present invention has good luminescence performance and high luminescence efficiency. It can be used to prepare optical sensors and optoelectronic devices, and can also be applied to fields such as information anti-counterfeiting and encryption.

[0070] The present invention has been tested many times. Now, some test results are cited as a reference for further detailed description of the invention, and the following is a detailed description in conjunction with specific embodiments.

[0071] Example 1 Preparation of Compound I

[0072] S1. Synthesis of Compound III:

[0073]

[0074] Add p - dimethoxybenzene (3.4 g, 25 mmol), paraformaldehyde (2.2 g, 75 mmol) and 200 mL of dichloromethane into a 500 - mL round - bottom flask. After maintaining the temperature at 0 °C in an ice bath for 30 min, add boron trifluoride diethyl etherate (3.5 mL, 0.5 mmol) into the round - bottom flask. React at 0 °C for 1 hour, then add water to quench the reaction. Extract three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase is dried with anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate is rotary - evaporated to obtain a crude product, and then the crude product is separated and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 100:1, v / v) to obtain 2.1 g of white solid Compound III, with a yield of 56%.

[0075] S2. Synthesis of Compound IV:

[0076]

[0077] Add Compound III (6 g, 8 mmol), ammonium cerium(IV) nitrate (8.98 g, 16 mmol), 100 mL of dichloromethane and 10 mL of water into a 500 - mL round - bottom flask. Then react at room temperature for 1 h, and extract three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase is dried with anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate is rotary - evaporated to obtain a crude product, and then the crude product is separated and purified by silica gel column chromatography (dichloromethane / petroleum ether = 1:1, v / v) to obtain 2.15 g of red solid Compound IV, with a yield of 37.3%.

[0078] S3. Synthesis of Compound V:

[0079]

[0080] Add Compound IV (2.1 g, 2.9 mmol), sodium dithionite (5.4 g, 31 mmol), 100 mL of dichloromethane and 10 mL of water into a 500 - mL round - bottom flask. Then react at room temperature for 12 h, and extract three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase is dried with anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate is rotary - evaporated to obtain 1.9 g of white solid Compound V, with a yield of 90.2%.

[0081] S4. Synthesis of Compound VI:

[0082]

[0083] Add compound Ⅴ (2.1 g, 1 mmol), 1 mL of pyridine and 100 mL of dichloromethane to a 250 mL round-bottom flask. After maintaining the temperature at 0 °C for 30 min, add trifluoromethanesulfonic anhydride (8.6 mL, 2 mmol) to the round-bottom flask, then gradually restore to room temperature. After reacting for 12 h, quench the reaction with water, and then extract three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase is dried over anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate is rotary evaporated to obtain a crude product, and then the crude product is separated and purified by silica gel column chromatography (dichloromethane / petroleum ether = 1:1, v / v) to obtain 1.8 g of white solid compound Ⅵ, with a yield of 62%.

[0084] S5、Synthesis of compound Ⅷ:

[0085]

[0086] Add 4-bromo-2,6-dimethylaniline (2 g, 10 mmol), bis(pinacolato)diboron (6.34 g, 25 mmol), palladium (548 mg, 0.75 mmol), potassium carbonate (2.94 g, 30 mmol) and 1,4-dioxane (10 mL) to a 200 mL Schlenk flask. After degassing by freezing three times, then heat the reaction system at 100 °C overnight. Subsequently, cool the reaction solution to room temperature, and then extract three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase is dried over anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate is rotary evaporated to obtain a crude product, and then the crude product is separated and purified by silica gel column chromatography (petroleum ether / dichloromethane = 1:1, v / v) to obtain 1.3 g of white solid compound Ⅶ, with a yield of 53%.

[0087]

[0088] Add compound Ⅵ (100 mg, 0.1 mmol), compound Ⅶ (62 mg, 0.25 mmol), palladium (29 mg, 0.025 mmol), potassium carbonate (84 mg, 0.6 mmol), tetrahydrofuran (5 mL) and water (1 mL) to a 50 mL Schlenk flask. After degassing by freezing three times, then heat the reaction system at 70 °C overnight. Subsequently, cool the reaction solution to room temperature, and then extract three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase is dried over anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate is rotary evaporated to obtain a crude product, and then the crude product is separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate = 4:1, v / v) to obtain 80 mg of white solid compound Ⅷ, with a yield of 85%.

[0089] S6、Synthesis of compound Ⅸ:

[0090]

[0091] Compound VIII (1 g, 1.1 mmol), 2-bromobenzyl bromide (1.6 g, 6.4 mmol), sodium hydroxide (689 mg, 17.2 mmol), 30 mL of tetrahydrofuran and 5 mL of water were added to a 200 mL round-bottom flask. The mixture was heated to 70 °C and reacted at 70 °C for 20 h. The reaction solution was cooled to room temperature and then extracted three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The collected organic phase was dried over anhydrous sodium sulfate, allowed to stand and filtered. The obtained filtrate was rotary evaporated to obtain a crude product, and then the crude product was separated and purified by silica gel column chromatography (petroleum ether / dichloromethane = 2:1, v / v) to obtain 800 mg of white solid compound IX with a yield of 46.3%.

[0092] S7. Synthesis of Compound I:

[0093]

[0094] Compound IX (100 mg, 0.06 mmol) was placed in a dry Schlenk flask, and nitrogen was evacuated and replaced. 30 mL of tetrahydrofuran was added to the Schlenk flask and cooled to -78 °C. After 30 min, n-butyllithium (0.18 mL, 1.6 M n-hexane solution, 0.3 mmol) was slowly added by syringe. After stirring at low temperature of -78 °C for 2 h, a solution of MesB(OMe)2 (31 mg, 0.16 mmol) in 5 mL of tetrahydrofuran was slowly added to the reaction system. After the addition was completed, the system was slowly restored to room temperature and stirred overnight. Then it was extracted three times, each time using 30 mL of dichloromethane and 20 mL of water for extraction. The combined organic phases were dried over anhydrous sodium sulfate, the desiccant was filtered off, the solvent was removed by distillation under reduced pressure, and the residue was separated by column chromatography with an eluent of dichloromethane:petroleum ether = 1:8 to obtain 28 mg of light yellow solid compound I with a yield of 30%.

[0095] The compound I prepared in Example 1 was identified:

[0096] The 1H NMR spectrum of Compound I is as Figure 1 shown. The detailed data of the 1H NMR spectrum of Compound I are as follows. The test instrument is (400 MHz Bruker Avance nuclear magnetic resonance spectrometer); the test solution is Chloroform-d (chloroform-d).

[0097] 11H NMR (400 MHz, Chloroform-d) δ: 7.59–7.49 (m, 8H), 7.29 (d, J = 7.1 Hz, 10H), 6.89 (d, J = 5.5 Hz, 8H), 6.77 (s, 2H), 6.71 (d, J = 11.0 Hz, 2H), 6.63 (s, 2H), 6.05 (s, 2H), 4.23 (d, J = 12.9 Hz, 4H), 4.08 (d, J = 13.6 Hz, 2H), 3.90 (d, J = 13.7 Hz, 2H), 3.85–3.70 (m, 10H), 3.64–3.52 (m, 18H), 3.41 (d, J = 14.1 Hz, 6H), 2.39 (s, 6H), 2.02 (s, 12H), 1.94 (s, 12H).

[0098] The racemized compound I was optically resolved by high performance liquid chromatography (HPLC) with the model of Agilent 1260 Infinity II. Specifically, compound I was passed through a chiral column (Daicel Chiralpak IG-3) and tested under the conditions that the mobile phase was n-hexane / isopropanol / dichloromethane = 95:2:3 (v / v / v), the flow rate was 0.5 mL / min, and the column temperature was 30 °C. Two peaks with equal areas could be observed. The HPLC chromatogram of compound I is as Figure 2 shown, and its peak table is shown in Table 1.

[0099] Table 1

[0100]

[0101] From Figure 2 and Table 1, it can be seen that compound I has good chemical stability and configurational stability at room temperature. The compound I containing a pillararene skeleton modified by a large steric hindrance substituent can be chiral resolved, which provides a certain feasibility value for further study of its circularly polarized luminescence properties.

[0102] The prepared compound I was subjected to fluorescence emission test and ultraviolet absorption test.

[0103] The prepared compound I was dissolved in five solutions with different polarities: n-hexane, ether, chloroform (CHCl3), tetrahydrofuran (THF), and acetonitrile (MeCN) to prepare solutions with a concentration of 1×10 -5 mol / L. According to the polarity, the fluorescence spectra of each group of solutions were tested using a Lengguang Tech F97 Pro fluorescence spectrometer. The test results are as Figure 3 shown.

[0104] The prepared Compound I was separately dissolved in five solvents with different polarities, namely hexane, ether, chloroform (CHCl₃), tetrahydrofuran (THF), and acetonitrile (MeCN), to prepare solutions with a concentration of 1×10 -5 mol / L. Then, absorption spectra of each group of solutions were measured using a Jasco-V 770 spectrophotometer according to the increasing order of polarity. The test results are as Figure 4 shown.

[0105] Figure 3 Figure shows the fluorescence spectra of Compound I prepared in Example 1 in different solvents.

[0106] As can be seen from Figure 3 , when Compound I was dissolved in solvents with different polarities, from hexane, ether, chloroform, tetrahydrofuran to acetonitrile, with the increase of solvent polarity, a significant red shift of the fluorescence peak of Compound I could be observed. This indicates that the fluorescence emission of Compound I is related to the solvent polarity, and the greater the solvent polarity, the more obvious the intramolecular charge transfer.

[0107] Figure 4 Figure shows the ultraviolet-visible absorption spectra of Compound I prepared in Example 1 in different solvents.

[0108] As can be seen from Figure 4 , the ultraviolet absorption spectra show that Compound I exhibits similar absorption characteristics in solvents with different polarities, and the maximum absorption wavelength is around 400 nm.

[0109] The above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that: they can still modify the technical solutions recorded in the foregoing embodiments, or perform equivalent replacements on some of the technical features; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the various embodiments of the present invention, and should all be included in the protection scope of the present invention.

Claims

1. A compound having the structure of Formula I:

2. The preparation method of the compound with the structure of formula I as described in claim 1, characterized in that, Comprising the following steps: S1. Synthesis of Compound III: Compound II having the structure of Formula II reacts with paraformaldehyde and boron trifluoride diethyl etherate in a first solvent to obtain Compound III having the structure of Formula III; S2. Synthesis of Compound IV: Compound III having the structure of Formula III reacts with ammonium cerium(IV) nitrate in a second solvent to obtain Compound IV having the structure of Formula IV; S3. Synthesis of Compound V: Compound IV having the structure of Formula IV reacts with sodium dithionite in a third solvent to obtain Compound V having the structure of Formula V; S4. Synthesis of Compound VI: Compound V having the structure of Formula V reacts with pyridine and trifluoromethanesulfonic anhydride in a fourth solvent to obtain Compound VI having the structure of Formula VI; S5. Synthesis of Compound VIII: Compound VI having the structure of Formula VI reacts with Compound VII having the structure of Formula VII in a fifth solvent in the presence of a catalyst and a first base to obtain Compound VIII having the structure of Formula VIII; S6. Synthesis of Compound IX: Compound VIII having the structure of Formula VIII reacts with 2-bromobenzyl bromide in a sixth solvent in the presence of a second base to obtain Compound IX having the structure of Formula IX; S7. Synthesis of Compound I: Compound IX having the structure of Formula IX reacts with n-butyllithium and MesB(OMe)2 in a seventh solvent to obtain Compound I having the structure of Formula I.

3. The preparation method according to claim 2, wherein In step S1, the first solvent is at least one of dichloromethane and chloroform.

4. The preparation method according to claim 2, wherein In step S2, the second solvent is a mixture of dichloromethane and water.

5. The preparation method according to claim 2, characterized in that, In step S3, the third solvent is a mixture of dichloromethane and water.

6. The preparation method according to claim 2, wherein In step S4, the fourth solvent is dichloromethane.

7. The preparation method according to claim 2, characterized in that, In step S5, the catalyst is a palladium catalyst; The first base is potassium carbonate; The fifth solvent is a mixture of tetrahydrofuran and water, or a mixture of toluene, ethanol and water.

8. The preparation method according to claim 2, characterized in that, In step S6, the second base is sodium hydroxide; The sixth solvent is a mixture of tetrahydrofuran and water.

9. The preparation method according to claim 2, wherein In step S7, the seventh solvent is at least one of tetrahydrofuran and diethyl ether.

10. Use of the compound having the structure of Formula I according to claim 1 in the preparation of optoelectronic devices.

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