[2.2]paracyclophane derivative for preparing parylene film, preparation method therefor and use thereof

Abstract

Disclosed in the present invention are a [2.2]paracyclophane derivative for preparing a parylene film, a preparation method therefor and the use thereof. The present invention specifically relates to 4,16-bis(trifluoromethyl)-[2.2]paracyclophane. The preparation method therefor comprises the following steps: S1, reacting 4-methyl-2-(trifluoromethyl) benzoic acid with a reducing reagent in the presence of a solvent to obtain an intermediate 1; S2, reacting the intermediate 1 with a chlorinating agent in the presence of a solvent to obtain an intermediate 2; S3, reacting the intermediate 2 with an organic amine in the presence of a solvent to obtain an intermediate 3; and S4, reacting the intermediate 3 with a basic reagent in the presence of a polymerization inhibitor and a solvent to obtain 4,16-bis(trifluoromethyl)-[2.2]paracyclophane. A parylene film prepared by using the compound as a monomer exhibits high hydrophobicity, which is superior to that of waterproof Parylene AF4, the best among those commercially available. In addition, the derivative involves low preparation cost and has good application prospects in terms of protective materials.

Description

A parylene ring bichromophoric derivative for preparing parylene film and preparation method and application thereof TECHNICAL FIELD

[0001] The present application relates to the field of organic synthesis, in particular to a parylene ring bichromophoric derivative for preparing parylene film and preparation method and application thereof. BACKGROUND

[0002] The parylene family prepared by p-xylene ring bichromophoric and its derivatives is a kind of protective material with extremely excellent performance. Due to the characteristics of no need for solvent and initiator, high purity, good flexibility, smoothness without pinhole and good shape retention, this kind of material is a very important existence in the three-proofing materials, and different p-xylene derivatives can also bring new characteristics on the basis of the original excellent performance, so that the parylene material has a very wide application range (see: C. P. Tan, H. G. Craighead, Materials, 2010, 3, 1803-1832), and has excellent performance in micro-electro-mechanical system, electronic components, biological medicine, protection and other application scenarios.

[0003] This kind of p-xylene ring diatomic body and its derivatives combined with chemical vapor deposition (CVD) process can be conformally and pinhole-free deposited on any material and any complex geometry to form a parylene film, which provides an excellent barrier to prevent water diffusion and corrosion resistance. Therefore, the parylene series film opens up a broad application field in any technical field that requires a clear dielectric, hydrophobic and chemical barrier (see: C. Desai, N. Laube, J. Coat. Technol. Res., 2019, 16(1), 103-111). For example, in its brilliant biomedical field, surface wettability is one of the key properties of parylene film, which will affect the biological response of micro-device biological interface, such as cell adhesion, protein adsorption and blood coagulation, etc. (see: X. P. Bi, B. P. Crum, W. Li, J. Microelectromech. Systems, 2014, 23(3), 628-635). Currently, hydrophobic parylene includes parylene C, parylene D, parylene AF4, etc., and the untreated water contact angles thereof are 87°, 97° and 100°, respectively (see: B. J. Raos, M. C. Simpson, C. S. Doyle, E. S. Graham, C. P. Unsworth, PLoS One, 2019, 14(6), e0218850). The hydrophobic angle of this kind of parylene film is usually not higher than 100°, and the monomer of parylene AF4 with relatively better hydrophobic performance has a high cost of up to 200,000 USD / 1 kg (see: G. Lee, H. J. Lee, J. Lee, K. J. Lee, Thin Solid Films, 2024, 797, 140333), which seriously limits its practical application in different fields.

[0004] Therefore, there is an urgent need for a monomer for preparing a parylene film with low preparation cost and good hydrophobicity to promote the use of parylene film in different fields. SUMMARY

[0005] The present application provides a p-xylene ring diatomic body derivative for preparing a parylene film and a preparation method and application thereof. The parylene film prepared from 4,16-bis(trifluoromethyl)-[2,2]-p-xylene ring diatomic body as a monomer exhibits high hydrophobicity, which is better than parylene AF4. The compound can be prepared from 4-methyl-2-(trifluoromethyl) benzoic acid as a starting material through reduction, chlorination, salt formation and cyclization reaction processes, which is simple to operate and low in preparation cost, and has good application prospect in protective materials.

[0006] To solve the above technical problems, the present application provides the following technical solutions:

[0007] The p-xylene ring dimer derivative for preparing the paroxetine film according to the first aspect of the present application has the following structure:

[0008] The second aspect of the present application provides a preparation method of the p-xylene ring dimer derivative for preparing the paroxetine film according to the first aspect, comprising the following steps:

[0009] S1, reacting 4-methyl-2-(trifluoromethyl)benzoic acid with a reducing agent in the presence of a first solvent to obtain an intermediate 1;

[0010] S2, reacting the intermediate 1 with a chlorinating agent in the presence of a second solvent to obtain an intermediate 2;

[0011] S3, reacting the intermediate 2 with an organic amine in the presence of a third solvent to obtain an intermediate 3;

[0012] S4, reacting the intermediate 3 with a base reagent in the presence of a polymerization inhibitor and a fourth solvent to obtain the p-xylene ring dimer derivative;

[0013] The structures of the intermediates 1-3 are as follows:

[0014] Wherein, R is methyl, ethyl or propyl.

[0015] Further, in S1, the reducing agent is preferably lithium aluminum hydride and / or sodium borohydride; more preferably, the molar ratio of 4-methyl-2-(trifluoromethyl)benzoic acid to reducing agent is (0.5-3):1, such as 0.5:1, 1:1, 1.5:1, 2:1, 2.5:1, 3:1, etc., including but not limited to the above-mentioned molar ratios.

[0016] Further, in S1, the first solvent is selected from one or more of diethyl ether, tetrahydrofuran, dichloromethane, toluene, and in some preferred embodiments, the first solvent is diethyl ether; more preferably, the mass ratio of 4-methyl-2-(trifluoromethyl)benzoic acid to the first solvent is (0.01-0.2):1.

[0017] Further, in S1, the temperature of the reaction is preferably 30-60℃, and the time is preferably 6-24h.

[0018] Further, in S1, first dissolve 4-methyl-2-(trifluoromethyl)benzoic acid in the first solvent, then add the reducing agent at 0-30℃, and then warm up to 30-60℃ for 6-24h.

[0019] Further, in S1, the preparation method further comprises the following steps: after the reaction, cooling to 0-5℃, adding water and / or sodium hydroxide aqueous solution to quench the reaction, filtering to remove the precipitate, and drying the organic phase to obtain the intermediate 1.

[0020] Further, in S2, the chlorinating agent is preferably one or more of phosphorus chloride, thionyl chloride, concentrated hydrochloric acid, Lucas reagent; more preferably, the molar ratio of the intermediate 1 to the chlorinating agent is (0.5-3):1, for example 0.5:1, 1:1, 1.5:1, 2:1, 2.5:1, 3:1, etc., including but not limited to the above-mentioned molar ratios.

[0021] Further, in S2, the second solvent is selected from one or more of dichloromethane, diethyl ether, tetrahydrofuran, toluene, and in some preferred embodiments, the second solvent is dichloromethane; more preferably, the mass ratio of the intermediate 1 to the second solvent is (0.01-0.4):1.

[0022] Further, in S2, the temperature of the reaction is preferably 30-60℃, and the time is preferably 1-3h.

[0023] Further, in S2, the intermediate 1 is first dissolved in the second solvent, then the chlorinating agent is added at 0-30℃, and then the temperature is raised to 30-60℃ for 1-3h.

[0024] Further, in S2, the preparation method further comprises the following steps: after the reaction, cooling to 0-20℃, adding saturated sodium bicarbonate solution to quench the reaction, and then extracting and evaporating to obtain the intermediate 2.

[0025] Further, in S3, the organic amine is preferably trimethylamine, triethylamine or tripropylamine; more preferably, the molar ratio of the intermediate 2 to the organic amine is (0.5-2.5):1, for example 0.5:1, 1:1, 1.5:1, 2:1, 2.5:1, etc., including but not limited to the above-mentioned molar ratios.

[0026] Further, in S3, the third solvent is toluene; more preferably, the mass ratio of the intermediate 2 to the third solvent is (0.2-0.5):1.

[0027] Further, in S3, the temperature of the reaction is preferably 40-80℃, and the time is preferably 3-8h.

[0028] Further, in S3, the intermediate 2 is first dissolved in the third solvent, then the organic amine is added, and then the temperature is raised to 40-80℃ for 3-8h.

[0029] Further, in S3, the preparation method further comprises the following steps: after the reaction, standing the water layer, washing, drying to obtain the intermediate 3.

[0030] Further, in S4, the base reagent is preferably one or more of sodium hydroxide, potassium hydroxide, sodium ethoxide, and potassium ethoxide, and the polymerization inhibitor is preferably one or more of p-phenol monobutyl ether, tert-butyl catechol, and p-tert-butyl phenol; more preferably, the molar ratio of the intermediate 3, the base reagent, and the polymerization inhibitor is (20-50):(150-200):1.

[0031] Further, in S4, the fourth solvent is preferably one or more of water, toluene, N,N-dimethylformamide, N,N-dimethylacetamide, sulfolane, benzene, and xylene.

[0032] Further, in S4, the reaction temperature is preferably 80-120℃, and the reaction time is preferably 2-24h.

[0033] Further, in S4, the intermediate 3 is first dissolved in water to obtain an aqueous solution of the intermediate 3, and then the aqueous solution of the intermediate 3 is added dropwise to a mixed solution containing the base reagent, the polymerization inhibitor, and the fourth solvent at 80-100℃, after the dropwise addition is completed, the temperature is raised to 100-120℃, and the reaction is carried out for 2-24h; preferably, the mass ratio of the intermediate 3 to water is (0.1-0.8):1.

[0034] Further, in S4, the preparation method further comprises the following steps: after the reaction, separating the organic phase by adding water, washing the organic phase with water and / or an acid solution, then adding activated carbon to the washed organic phase, heating to 40-100℃, stirring for 0.5-3h, and then filtering and cooling to crystallize to obtain the p-xylene ring dimer derivative; preferably, the solid obtained by cooling and crystallization is dissolved in n-hexane, and recrystallization is performed to obtain the p-xylene ring dimer derivative.

[0035] The present application also provides a paralyne film prepared by using the p-xylene ring dimer derivative of the first aspect as a monomer by chemical vapor deposition.

[0036] Compared with the prior art, the present application has the following advantages:

[0037] 1. The present application provides a p-xylene ring dimer derivative for preparing a paralyne film: 4,16-bis(trifluoromethyl)-[2,2]-p-xylene ring dimer, and the hydrophobic angle of the paralyne film prepared by using the compound as a monomer can reach 105°, which is significantly better than the commonly used hydrophobic paralyne on the market, and is better than the best waterproof paralyne AF4 currently on the market.

[0038] 2. The application also provides a synthesis method of 4, 16-bis (trifluoromethyl) -[2, 2] -p-xylylene dimer, which uses 4-methyl-2- (trifluoromethyl) benzoic acid as a starting material, and is prepared through reduction, chlorination, salification and cyclization. The synthesis method has the advantages of simple operation, mild reaction conditions, high product yield, low preparation cost, and is suitable for batch preparation. Compared with the expensive hydrophobic parrylin AF4 monomer, the 4, 16-bis (trifluoromethyl) -[2, 2] -p-xylylene dimer prepared at low cost has good application prospect in protective materials. BRIEF DESCRIPTION OF DRAWINGS

[0039] Fig. 1 is a reaction flow diagram for preparing 4, 16-bis (trifluoromethyl) -[2, 2] -p-xylylene dimer;

[0040] Fig. 2 is a nuclear magnetic hydrogen spectrum of 4-methyl-2- (trifluoromethyl) benzyl alcohol;

[0041] Fig. 3 is a nuclear magnetic carbon spectrum of 4-methyl-2- (trifluoromethyl) benzyl alcohol;

[0042] Fig. 4 is a nuclear magnetic hydrogen spectrum of 4-methyl-2- (trifluoromethyl) chlorobenzyl;

[0043] Fig. 5 is a nuclear magnetic carbon spectrum of 4-methyl-2- (trifluoromethyl) chlorobenzyl;

[0044] Fig. 6 is a nuclear magnetic hydrogen spectrum of 4-methyl-2- (trifluoromethyl) benzyl trimethyl ammonium chloride;

[0045] Fig. 7 is a nuclear magnetic carbon spectrum of 4-methyl-2- (trifluoromethyl) benzyl trimethyl ammonium chloride;

[0046] Fig. 8 is a nuclear magnetic hydrogen spectrum of 4, 16-bis (trifluoromethyl) -[2, 2] -p-xylylene dimer;

[0047] Fig. 9 is a nuclear magnetic carbon spectrum of 4, 16-bis (trifluoromethyl) -[2, 2] -p-xylylene dimer;

[0048] Fig. 10 is a contact angle test result of a parrylin film prepared by using 4, 16-bis (trifluoromethyl) -[2, 2] -p-xylylene dimer as a monomer;

[0049] Fig. 11 is a comparison diagram of water contact angles of parrylin films prepared by different monomers. DETAILED DESCRIPTION

[0050] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used in the description herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. The phrase "includes" or "including" as used herein is meant to be non- limiting, i.e., to include, but not to the exclusion of, other components.

[0051] The application will be further described with reference to the following examples and drawings, in which:

[0052] Example 1

[0053] This example relates to the preparation of 4, 16 bis (trifluoromethyl) - [2, 2] -p- xylene ring diatomic, the reaction flow as shown in Figure 1, as follows:

[0054] Preparation of intermediate 1:

[0055] In a 500 mL three-necked flask, 15.31 g of 4-methyl-2- (trifluoromethyl) benzoic acid was added, and 300 mL of ether solvent was added, and stirred for 30 min under nitrogen atmosphere, cooled to 0 ℃, then added 45 mL of lithium aluminum hydride (2.5 mol / L) tetrahydrofuran solution, slowly warmed to 40 ℃, heated to reflux, continue to stir for 24 h, after the reaction was completed, cooled to 0 ℃, then added 4.3 mL of water, 4.3 mL of 15% sodium hydroxide solution, 12.9 mL of water to quench the reaction, filtered to remove the precipitate, the organic phase was dried, and the solvent was removed to obtain 13.05 g of intermediate 1, the yield was 97.90%;

[0056] The prepared intermediate 1 was characterized by nuclear magnetic resonance, as shown in Figures 2 and 3, as follows:

[0057] 1 H NMR (400 MHz, CDCl3): δ 7.57 (d, J = 7.8 Hz, 1H) 7.45 (s, 1H), 7.38 (d, J = 1.6 Hz, 1H), 4.84 (s, 2H), 2.40 (s, 3H).

[0058] 13 C NMR (75 MHz, CDCl3): δ 137.57, 136.15, 132.74, 129.22, 126.45, 126.37, 122.69, 61.44, 21.01.

[0059] From the characterization results, intermediate 1 is 4-methyl-2-(trifluoromethyl) benzene methanol.

[0060] Preparation of intermediate 2:

[0061] Take 12 g of the above prepared intermediate 1 in a 250 mL three-necked flask, and add 120 mL of ether solvent, stir for 30 min under the atmosphere of nitrogen to cool to 0 ℃, then add 8 mL of thionyl chloride, slowly warm to 40 ℃, heat to reflux, continue to stir for 3 h, after cooling, quench with saturated sodium bicarbonate solution, separate the layers, take the organic phase, evaporate to get 9.68 g of intermediate 2, the yield is 73.54%.

[0062] The prepared intermediate 2 was characterized by nuclear magnetic resonance, as shown in Figures 4 and 5, as follows:

[0063] 1 H NMR (400 MHz, CDCl3): δ 7.47 (d, J = 7.7 Hz, 1H), 7.44 (s, 1H), 7.33 (d, J = 7.7 Hz, 1H), 4.69 (s, 2H), 2.37 (s, 3H).

[0064] 13 C NMR (100 MHz, CDCl3): δ 138.90, 132.97, 132.71, 131.92, 130.92, 126.72, 126.67, 42.07, 21.04.

[0065] From the characterization results, intermediate 2 is 4-methyl-2-(trifluoromethyl) chlorobenzene.

[0066] Preparation of intermediate 3:

[0067] In a 250 mL three-necked flask, add 20 g of intermediate 2, 65 mL of toluene and 20 g of 30% trimethylamine, keep the temperature at 35 ℃, continue to stir for 4 h, stand and separate the layers, take the water layer, wash the obtained water layer with tert-butyl methyl ether. Filter the water layer through diatomite, remove the solvent to get 18.6 g of intermediate 3, the yield is 76.76%.

[0068] The prepared intermediate 3 was characterized by nuclear magnetic resonance, as shown in Figures 6 and 7, as follows:

[0069] 1 H NMR (400 MHz, CDCl3): δ 7.96 (d, J = 7.9 Hz, 1H), 7.56 (d, J = 1.8 Hz, 1H), 7.49 (d, J = 1.7 Hz, 1H), 5.07 (s, 2H), 3.43 (s, 9H), 2.44 (s, 3H).

[0070] 13 C NMR (100 MHz, CDC13): δ 142.02, 136.39, 133.33, 128.32, 128.27, 125.30, 122.31, 64.88, 53.49, 21.26.

[0071] From the characterization results, intermediate 3 is 4-methyl-2-(trifluoromethyl) benzyl trimethyl ammonium chloride.

[0072] Preparation of 4, 16 bis (trifluoromethyl) - [2, 2] -p-xylylene dimer:

[0073] 20 g of intermediate 3 was dissolved in 30 g of water to obtain a quaternary ammonium salt solution for standby. In a three-necked flask, 20 g of solid sodium hydroxide and 50 g of water were configured into a solution, then 100 mL of toluene, 0.8 g of p-t-butylphenol were added, heated to 95°C, and then the quaternary ammonium salt solution was slowly added. It took about 2 hours to complete the dropwise addition. After slowly warming to 110°C, it was kept for 8 h, and about 20 mL of water was separated during the whole process. After the reaction was completed, it was cooled to room temperature, 20 mL of water was added, and the alkaline solution was separated after standing. After washing with 20 mL of water, 20 mL of dilute sulfuric acid solution, and 20 mL of ice water, 10 g of activated carbon was added to the toluene layer heated to 80°C, stirred for 0.5 h, then filtered while hot, and cooled to crystallize. Recrystallization was performed with 220 g of n-hexane, and the product was dried to obtain 12.4 g of the final product, with a yield of 36.1% and a purity of 99.5%.

[0074] The final product prepared was subjected to nuclear magnetic resonance characterization, as shown in Figures 8 and 9, and the specific results are as follows:

[0075] 1 H NMR (400 MHz, CDC13): δ 6.85 (d, J = 1.9 Hz, 1H), 6.79 (d, J = 7.9 Hz, 1H), 6.44 (d, J = 7.9 Hz, 1H), 3.41-3.52 (m, 1H), 3.24 (dd, J = 10.4, 8.7 Hz, 1H) 3.04-3.15 (m, 2H).

[0076] 13 C NMR (100 MHz, CDC13): δ 140.00, 138.14, 135.67, 135.29, 129.12, 129.07, 34.79, 32.88.

[0077] From the characterization results, the final product is 4, 16 bis (trifluoromethyl) - [2, 2] -p-xylylene dimer.

[0078] Comparative Example 1

[0079] The 4, 16-dibromo-[2, 2]-p-xylylene dimer was dissolved in N, N-dimethylacetamide, methyl fluorosulfonyl difluoroacetate was added, cuprous iodide was used as catalyst, and the mixture was reacted at 80°C for 8 hours. After filtration and washing, the obtained crude product was tested by mass spectrometry. It was found that about 30% of the product was produced, and about 40% of the monosubstituted byproduct was produced. Column chromatography was used for separation. However, the polarities of the raw material, the product and the byproduct were very small and very close, and they could not be separated and purified.

[0080] Comparative Example 2

[0081] The 4, 16-dibromo-[2, 2]-p-xylylene dimer was dissolved in methyl pyrrolidone, sodium trifluoroacetate was added, and cuprous iodide was used as catalyst. The mixture was reacted at 140°C for 72 hours. After filtration and washing, the obtained crude product was tested by mass spectrometry. It was found that only 10% of the product was produced, and about 20% of the monosubstituted byproduct was produced, and a large amount of unreacted raw material. Column chromatography was used for separation. However, the polarities of the raw material, the product and the byproduct were very small and very close, and they could not be separated and purified.

[0082] Application and performance characterization

[0083] The 4, 16-bis(trifluoromethyl)-[2, 2]-p-xylylene dimer (abbreviation: parylene DCF3) prepared in Example 1 and commercially available parylene monomers (parylene C monomer, parylene D monomer, and parylene AF4 monomer) were used to prepare corresponding parylene films by the following methods. The specific operations are as follows:

[0084] The parylene monomer was placed in an evaporation chamber, and the parylene monomer was evaporated in the evaporation chamber at a vacuum degree of 4 Pa and a temperature of 180°C, and was cracked in a cracking furnace at a temperature of 680°C. Finally, a transparent film was deposited on a glass sheet in a film coating cabin. After film formation, the parylene film was peeled off from the glass plate.

[0085] Structure of the parylene DCF3 monomer: Structure of the prepared parylene DCF3 film: The water contact angle test results of the film are shown in FIG. 10. The hydrophobic angle can reach 105°.

[0086] Structure of the parylene C monomer: Structure of the prepared parylene C film:

[0087] Structure of the parylene D monomer: Structure of the prepared parylene D film:

[0088] Structure of the parylene AF4 monomer: The structure of the prepared parylene AF4 film is as follows:

[0089] The test results of the water contact angle of the film prepared from different parylene monomers and the hydrophobic angle of the parylene CCF3 film reported in the literature (G. Lee, H. J. Lee, J. Lee, K. J. Lee, Thin Solid Films. 2024, 797, 140333) are shown in Table 1 below, and the structure of the parylene CCF3 monomer is The film structure is

[0090] Table 1

[0091] As can be seen from Table 1 and Figure 11, the hydrophobic angle of the parylene film prepared from the 4,16-bis(trifluoromethyl)-[2,2]-p-xylylene dimer as a monomer provided by the present application is significantly higher than that of the above-mentioned hydrophobic parylene material, and even better than the hydrophobicity of the film prepared from parylene AF4, and the preparation cost is much lower than that of parylene AF4, and has a good application prospect in hydrophobic protective materials.

[0092] The above-described embodiments are only preferred examples for fully illustrating the present application, and the protection scope of the present application is not limited thereto. Any equivalent replacement or transformation of the present application made by those skilled in the art based on the present application is within the protection scope of the present application. The protection scope of the present application is subject to the claims.

Claims

1. A p-xylylenediamine derivative for use in the preparation of a thin film of parathyroid hormone, characterized in that, The structure of the p-xylene diradical derivative is shown below:

2. A process for the preparation of the p-xylene cyclic diol derivative of claim 1, characterized by, The method comprises the following steps: S1, reacting 4-methyl-2-(trifluoromethyl)benzoic acid with a reducing agent in the presence of a first solvent to obtain intermediate 1; S2, reacting the intermediate 1 with a chlorinating agent in the presence of a second solvent to obtain intermediate 2; S3, reacting the intermediate 2 with an organic amine in the presence of a third solvent to obtain intermediate 3; S4, reacting the intermediate 3 with a base reagent in the presence of a polymerization inhibitor and a fourth solvent to obtain the p-xylene ring diatomic derivative; The structures of the intermediates 1-3 are shown below, respectively: Wherein, R is methyl, ethyl or propyl.

3. The preparation method according to claim 2, characterized in that, In S1, at least one of the following characteristics is included: (1) the reducing agent is lithium aluminum hydride and / or sodium borohydride; (2) the molar ratio of 4-methyl-2-(trifluoromethyl)benzoic acid to reducing agent is (0.5-3):1; (3) the first solvent is selected from one or more of diethyl ether, tetrahydrofuran, dichloromethane and toluene; (4) the reaction temperature is 30-60℃, and the reaction time is 6-24h.

4. The production method according to claim 2 or 3, characterized by, In S1: First, 4-methyl-2-(trifluoromethyl)benzoic acid is dissolved in the first solvent, then the reducing agent is added at 0-30℃, and then the reaction is carried out at 30-60℃ for 6-24h; The preparation method further comprises the following steps: after the reaction, the temperature is lowered to 0-5℃, water and / or sodium hydroxide aqueous solution is added to quench the reaction, the precipitate is removed by filtration, and the organic phase is dried to obtain the intermediate 1.

5. The preparation method according to claim 2, characterized in that, In S2, at least one of the following characteristics is included: (1) the chlorinating agent is selected from one or more of phosphorus chloride, thionyl chloride, concentrated hydrochloric acid and Lucas reagent; (2) the molar ratio of intermediate 1 to chlorinating agent is (0.5-3):1; (3) the second solvent is selected from one or more of dichloromethane, diethyl ether, tetrahydrofuran and toluene; (4) the reaction temperature is 30-60℃, and the reaction time is 1-3h.

6. The production method according to claim 2 or 5, characterized by, In S2: First, intermediate 1 is dissolved in the second solvent, then the chlorinating agent is added at 0-30℃, and then the reaction is carried out at 30-60℃ for 1-3h; The preparation method further comprises the following steps: after the reaction, the temperature is lowered to 0-20℃, saturated sodium bicarbonate solution is added to quench the reaction, the organic layer is taken, and evaporation is carried out to obtain the intermediate 2.

7. The preparation method according to claim 2, characterized in that, In S3, at least one of the following characteristics is included: (1) the organic amine is trimethylamine, triethylamine or tripropylamine; (2) the molar ratio of intermediate 2 to organic amine is (0.5-2.5):1; (3) the third solvent is toluene; (4) the reaction temperature is 40-80℃, and the reaction time is 3-8h.

8. The production method according to claim 2 or 7, characterized by, In S3: First, intermediate 2 is dissolved in the third solvent, then the organic amine is added, and then the reaction is carried out at 40-80℃ for 3-8h; The preparation method further comprises the following steps: after the reaction, the organic layer is taken, washed and dried to obtain the intermediate 3.

9. The preparation method according to claim 2, characterized in that, In S4, at least one of the following characteristics is included: (1) the base reagent is selected from one or more of sodium hydroxide, potassium hydroxide, sodium ethoxide and potassium ethoxide; (2) the polymerization inhibitor is selected from one or more of p-phenol monobutyl ether, tert-butyl o-diphenol and p-tert-butyl phenol; (3) the molar ratio of the intermediate 3, the base reagent and the polymerization inhibitor is (20-50):(150-200):1; (4) the fourth solvent is selected from one or more of water, toluene, N,N-dimethylformamide, N,N-dimethylacetamide, sulfolane, benzene, xylene; (5) the reaction temperature is 80-120℃, and the reaction time is 2-24h.

10. The production method according to claim 2 or 9, characterized by, In S4, First, the intermediate 3 is dissolved in water to obtain an aqueous solution of the intermediate 3, and then the aqueous solution of the intermediate 3 is added dropwise to a mixed solution containing a base reagent, a polymerization inhibitor and a fourth solvent at 80-100℃, after the dropwise addition is completed, the temperature is raised to 100-120℃ and reacted for 2-24h; The preparation method further comprises the following steps: after the reaction, water is added to separate the organic phase, the organic phase is washed with water and / or an acid solution, then activated carbon is added to the washed organic phase, heated to 40-100℃ and stirred for 0.5-3h, and then filtered and cooled to crystallize to obtain the p-xylene ring diatom derivative.

11. A parylene film characterized in that, The p-xylene ring diatom derivative of claim 1 is used as a monomer to prepare the parylene film by a chemical vapor deposition method.

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