Synthesis method for 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl
The synthesis of 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl by reacting p-hydroxycinnamic acid with biphenyl dichlorobenzyl solves the problem of domestic production of photoelectric resist dry film raw materials, realizes an efficient and controllable synthesis process, reduces costs and improves product purity and yield.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- HEBEI CHIRAL STAR TECH CO LTD
- Filing Date
- 2025-03-28
- Publication Date
- 2026-07-30
AI Technical Summary
In the existing technology, the synthesis method of 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, the key raw material for photoelectric anti-corrosion dry film, has failed to meet the needs of domestic production, resulting in reliance on imports for high-end electronic materials. Furthermore, the use of hydroxystyrene poses the risks of self-polymerization and high costs.
p-hydroxycinnamic acid and biphenyl dichlorobenzyl were used as raw materials to generate p-hydroxystyrene through a dehydration reaction. Then, 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl was synthesized with inorganic base and polymerization inhibitor under suitable conditions. The reaction conditions were controlled to reduce side reactions and improve product yield.
It achieves an efficient and controllable synthesis process, reduces costs, improves product purity and yield, meets the industrial production requirements of green chemistry, and breaks through the manufacturing bottleneck of electronic materials.
Smart Images
Figure CN2025085703_30072026_PF_FP_ABST
Abstract
Description
A method for synthesizing 4,4′-bis((4-vinylphenoxy)methyl)-1,1′-biphenyl Technical Field
[0001] This invention relates to the field of organic synthesis technology, specifically to a method for synthesizing the polymer resin monomer 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. Background Technology
[0002] Electronic materials refer to materials used in electronic and microelectronic technologies, including dielectric materials, semiconductor materials, piezoelectric and ferroelectric materials, printed circuit materials, and display materials. The main components of photoresists include photoinitiators, photosensitive resins, solvents, monomers, and additives. The photosensitive resin is the basic framework of the photoresist and determines its basic properties after exposure. Currently, film-forming resins are broadly classified into three categories: (meth)acrylate systems, cyclic olefin systems, and maleic anhydride systems. Cyclic olefin polymers have a multi-aliphatic ring structure, exhibiting strong corrosion resistance and high light transmittance, making them one of the ideal materials for photoresists. Among photoresist dry films, there is a type of p-hydroxystyrene polymer, which possesses strong resistance to dry etching due to the large number of benzene rings in its compounds. Photoresist dry films are typically electronic-grade resins, mainly used in the fine patterning of display panels and discrete semiconductor devices. Currently, most of the photoresist dry films used in my country's photolithography technology, especially high-end products, rely on imports, necessitating independent research and development to improve domestic production efficiency.
[0003] 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, as a structural extension of p-hydroxystyrene, adds a diphenyl ring structure. As a derivative of p-hydroxystyrene, it can play multiple roles in photoresist dry films (PDFs), particularly in photosensitivity and crosslinking properties. The vinyl group in this compound can participate in free radical polymerization under ultraviolet light irradiation, crosslinking with other monomers or resins containing unsaturated bonds to form a three-dimensional network structure. This helps increase the mechanical strength, chemical stability, and dimensional stability of the film. The presence of a phenoxy group in this compound enables strong interaction with the substrate surface, thereby enhancing the adhesion of the resist dry film to substrates of different materials and ensuring that it will not easily peel off during subsequent etching processes. Therefore, broadening the synthesis method of the resin monomer 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl is beneficial for overcoming the manufacturing bottleneck of electronic materials and has significant research benefits. Summary of the Invention
[0004] (a) Technical problems to be solved
[0005] In view of the above-mentioned shortcomings and deficiencies of the prior art, the present invention provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, which uses p-hydroxycinnamic acid and biphenyl dichlorobenzyl as raw materials to react and obtain 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. This compound can be used as a new polymer monomer for photoelectric resist dry film, and can be used to modify photoelectric resist dry film, which is beneficial to breaking through the manufacturing bottleneck of electronic materials.
[0006] (II) Technical Solution
[0007] In a first aspect, the present invention provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, comprising the following steps:
[0008] S1. Add p-hydroxycinnamic acid, polymerization inhibitor and alkaline reagent to organic solvent, heat to carry out dehydration reaction, so that p-hydroxycinnamic acid is converted into p-hydroxystyrene.
[0009] S2. Cool the reaction system containing p-hydroxystyrene from S1 to room temperature, add an inorganic base and biphenyl dichlorobenzyl, and react in an ice bath. After the reaction is complete, add water to the reaction system multiple times and filter (preferably by suction filtration) to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0010] S3. Dissolve the crude product prepared in S2 completely in an organic solvent, filter (preferably by suction filtration), and the filtrate is a solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. Crystallize the solution to obtain 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0011] According to a preferred embodiment of the present invention, in S1, the organic solvent is at least one of toluene and N,N-dimethylformamide (DMF).
[0012] According to a preferred embodiment of the present invention, in S1, the alkaline reagent is an inorganic base or an alkaline salt, and the alkaline salt is at least one of anhydrous potassium carbonate, anhydrous potassium acetate, or anhydrous sodium carbonate.
[0013] Because p-hydroxystyrene is highly unstable, it readily undergoes side reactions, such as self-polymerization or other unintended chemical changes, under strongly alkaline conditions (e.g., the high pH environment provided by potassium hydroxide). This is because strong bases can promote certain types of reactions, especially for compounds containing active hydrogen or readily forming anions. Using weaker basic salts such as anhydrous potassium carbonate, anhydrous potassium acetate, or anhydrous sodium carbonate can provide sufficient alkalinity to drive the dehydration reaction while reducing side reactions caused by excessive alkalinity. This helps improve the selectivity and yield of the target product. Potassium acetate and sodium carbonate provide relatively mild alkalinity sufficient for the dehydration reaction of hydroxycinnamic acid. This mild condition not only helps control the reaction rate, but potassium acetate, as a weak base salt, also acts as a buffer, helping to maintain the reaction system within a relatively stable pH range.
[0014] According to a preferred embodiment of the present invention, in S1, the polymerization inhibitor is at least one selected from hydroquinone, p-methoxyphenol, p-tert-butylcatechol, phenothiazine, aluminum N-nitroso-N-phenylhydroxylamine, dialkyl dithiocarbamate, and p-benzoquinone.
[0015] Polymerization inhibitors can suppress or slow down polymerization reactions by capturing free radicals or other active intermediates, thereby preventing the chain growth of polymerization reactions such as styrene and preventing the self-polymerization of styrene and its derivatives.
[0016] p-Methoxyphenol (MEHQ) is a derivative of hydroquinone, which is more stable than pure hydroquinone and has lower volatility and toxicity. p-tert-butylcatechol (TBHQ) and phenothiazine are highly effective antioxidants and polymerization inhibitors. Aluminum N-nitroso-N-phenylhydroxylamine (NA-17) is particularly suitable for use at high temperatures and can effectively inhibit the thermally initiated polymerization of styrene and its derivatives. Dialkyl dithiocarbamates have good inhibitory effects on free radical-initiated polymerization reactions. p-Benzoquinone can react with free radicals to form stable complexes, thereby terminating the polymerization reaction. Under the condition that the dehydration reaction in S1 is around 150°C, the polymerization inhibitor is preferably at least one of NA-17 and phenothiazine. Both of these polymerization inhibitors remain highly effective at high temperatures and do not significantly interfere with the dehydration reaction itself; their dosage is preferably 1-5% of the theoretical mass of p-hydroxycinnamic acid.
[0017] According to a preferred embodiment of the present invention, in S1, the molar ratio of p-hydroxycinnamic acid to the basic reagent is 1:0.1-0.5, and the mass ratio of p-hydroxycinnamic acid to the polymerization inhibitor is 1:0.01-0.05.
[0018] According to a preferred embodiment of the present invention, in S1, when the organic solvent is DMF, the temperature of the dehydration reaction is 148-152°C, preferably 150°C; when the organic solvent is toluene, the temperature of the dehydration reaction is 105-110°C, preferably 110°C.
[0019] According to a preferred embodiment of the present invention, in step S2, the molar ratio of p-hydroxystyrene to inorganic base is 1:0.8-1, and the inorganic base used in step S2 is potassium hydroxide or sodium hydroxide.
[0020] According to a preferred embodiment of the present invention, in S3, the organic solvent is at least one of dichloromethane, petroleum ether and ethyl acetate, and the amount used is 4-10 times the volume of the crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0021] According to a preferred embodiment of the present invention, in S3, the crystallization process of the solution includes: rotary evaporation or negative pressure evaporation of organic solvent, recovery of organic solvent, cooling, solid-liquid separation, washing with anhydrous ethanol, drying, and other processes.
[0022] (III) Beneficial Effects
[0023] This invention proposes a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. Starting with p-hydroxycinnamic acid, p-hydroxystyrene is first prepared, then reacted with biphenyl dichlorobenzyl to obtain a crude product. After solvent dissolution and recrystallization, the target product can be obtained. The synthesis method of this invention features mild conditions, reliable and controllable reactions, few side reactions, and high product yield. Attached Figure Description
[0024] Figure 1 shows the 1H NMR spectrum of 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl from Example 1.
[0025] Figure 2 shows the infrared absorption spectrum of 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl from Example 1. Detailed Implementation
[0026] To better explain and facilitate understanding of the present invention, the present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.
[0027] As shown in the chemical equation below, a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl according to the present invention includes the following steps:
[0028] S1. Add p-hydroxycinnamic acid, polymerization inhibitor and alkaline reagent to organic solvent, heat to carry out dehydration reaction, so that p-hydroxycinnamic acid is converted into p-hydroxystyrene.
[0029] S2. Cool the reaction system containing p-hydroxystyrene from S1 to room temperature, add an inorganic base and biphenyl dichlorobenzyl, and react in an ice bath. After the reaction is complete, add water to the reaction system multiple times and filter (preferably by suction filtration) to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0030] S3. Dissolve the crude product prepared in S2 completely in an organic solvent, filter (preferably by suction filtration), and the filtrate is a solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. Crystallize the solution to obtain 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0031] The above synthetic method uses p-hydroxycinnamic acid as a starting point, rather than directly using p-hydroxystyrene as a raw material to prepare 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, which has the following technical advantages: ① Availability and cost of raw materials: p-Hydroxycinnamic acid: As a naturally occurring compound or an intermediate synthesized by simple chemical methods, p-hydroxycinnamic acid is likely to be more readily available and relatively inexpensive. Furthermore, it exists in nature (e.g., in some plants) and can be considered part of a renewable resource. p-Hydroxystyrene: In contrast, p-hydroxystyrene is a more specific chemical, and its synthesis and purification processes may be more complex, leading to higher costs. Moreover, due to its high reactivity, p-hydroxystyrene is very sensitive to oxygen, light, and temperature, and is prone to self-polymerization, making its storage and transportation more difficult. Special handling is required during storage and transportation, which not only increases the corresponding costs but also leads to more side reactions in S2 and a decrease in the yield of the target product. ② Reaction conditions and controllability: In step S1, a polymerization inhibitor is added to prevent the generated p-hydroxystyrene from self-polymerizing. This method allows for the generation of a small amount of p-hydroxystyrene in a controlled environment, which can then be immediately used in the next reaction, thus reducing the risk of self-polymerization. If commercially available p-hydroxystyrene is used directly, even with the addition of polymerization inhibitors, there may still be issues with partial self-polymerization or the inhibitors being oxidized. Furthermore, the concentration and type of polymerization inhibitors in commercial products may not be suitable for subsequent reaction conditions, and long-term storage can also lead to partial self-polymerization. ③ Purity and Quality Control: Generating p-hydroxystyrene on-site via the dehydration reaction of p-hydroxycinnamic acid allows for the direct use of freshly prepared products in the reaction system, avoiding the introduction of impurities due to long-term storage. This helps improve the purity and quality of the final product. ④ Process Flexibility: The above scheme provides greater process flexibility, allowing adjustment of reaction conditions at each step, such as temperature, time, and reagent ratios, to optimize the entire synthetic route. This flexibility is invaluable for developing new processes or improving existing ones. ⑤ Starting with a dehydration reaction from p-hydroxycinnamic acid ensures the generation of a portion of p-hydroxystyrene under controlled conditions, followed by a nucleophilic substitution reaction with biphenyl dichlorobenzyl in the presence of a suitable solvent and inorganic base to form the target compound. This process also involves an equilibrium process in which p-hydroxycinnamic acid is continuously converted to p-hydroxystyrene, and p-hydroxystyrene is continuously converted into the target compound.
[0032] The cost of using p-hydroxystyrene as a starting material is generally higher than that of p-hydroxycinnamic acid, especially in large-scale production. Furthermore, considering the need for polymerization inhibitors and other stabilizing measures, the overall process cost may be even higher. In summary, the synthesis of 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl from p-hydroxycinnamic acid not only considers economic feasibility but also ensures high efficiency and controllability of the reaction, as well as the quality and purity of the final product. This method not only provides better reaction control but also reduces the occurrence of side reactions, improving product purity and yield. Simultaneously, it meets the efficiency requirements of industrial production, reduces the trouble caused by handling unstable intermediates, and embodies the concept of "green chemistry" in chemical production—that is, using safer and more environmentally friendly raw materials as much as possible and minimizing waste generation and energy consumption through optimized reaction conditions.
[0033] The following are preferred embodiments of the present invention.
[0034] Example 1
[0035] This embodiment provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, the steps of which are as follows:
[0036] (1) Add 2g of p-hydroxycinnamic acid (12.20mmol; molecular weight 164.16), 0.12g of anhydrous potassium acetate (1.22mmol), 0.02g of phenothiazine and 20mL of DMF to a four-necked flask equipped with a thermometer, reflux condenser and mechanical stirrer. Heat to 150℃ and react for 1.5h to obtain a DMF reaction solution containing p-hydroxystyrene.
[0037] (2) Cool the reaction solution to room temperature, add 0.683 g KOH (12.20 mmol) solid and 1.53 g biphenyl dichlorobenzyl (6.1 mmol) to it, and stir in an ice bath for 2.5 h. Add water to the reaction system several times and filter to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0038] (3) The crude product was dissolved in 4 times its volume of dichloromethane, filtered, and a dichloromethane solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl was obtained. The solution was concentrated under negative pressure and allowed to stand to crystallize, yielding crystalline material. The crystallization process included: rotary evaporation or negative pressure evaporation of the organic solvent, recovery of the organic solvent, cooling, solid-liquid separation, washing with anhydrous ethanol, and drying.
[0039] The crystal was subjected to nuclear magnetic resonance and infrared absorption scanning. The 1H nuclear magnetic resonance spectrum is shown in Figure 1, and the infrared absorption spectrum is shown in Figure 2. Thus, it was confirmed that the obtained crystal was indeed 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, and the product yield was 70.27%.
[0040] Example 2
[0041] This embodiment provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, the steps of which are as follows:
[0042] (1) Add 2g of p-hydroxycinnamic acid (12.20mmol), 0.168g of anhydrous potassium carbonate (1.22mmol), 0.03g of NA-17 and 20mL of DMF to a four-necked flask equipped with a thermometer, reflux condenser and mechanical stirrer. Heat to 150℃ and react for 1.5h to obtain a DMF reaction solution containing p-hydroxystyrene.
[0043] (2) Cool the reaction solution to room temperature, add 0.683 g KOH (12.20 mmol) solid and 1.53 g biphenyl dichlorobenzyl (6.1 mmol) to it, and stir in an ice bath for 2.5 h. Add water to the reaction system several times and filter to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0044] (3) The crude product was dissolved in 5 times its volume of dichloromethane, filtered, and a dichloromethane solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl was obtained. The solution was concentrated under negative pressure and allowed to stand to crystallize, yielding 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl with a product yield of 65.36%.
[0045] Example 3
[0046] This embodiment provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, the steps of which are as follows:
[0047] (1) Add 2g of p-hydroxycinnamic acid (12.20mmol), 0.12g of anhydrous potassium acetate (1.22mmol), 0.02g of NA-17 and 20mL of toluene to a four-necked flask equipped with a thermometer, reflux condenser and mechanical stirrer. Heat to 110℃ and react for 2h to obtain a toluene reaction solution containing p-hydroxystyrene.
[0048] (2) Cool the reaction solution to room temperature, add 0.488 g NaOH (12.20 mmol) solid and 1.53 g biphenyl dichlorobenzyl (6.1 mmol) to it, and stir in an ice bath for 2.5 h. Add water to the reaction system several times and filter to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0049] (3) The crude product was dissolved in 4 times its volume of ethyl acetate, filtered, and a dichloromethane solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl was obtained. The solution was concentrated under negative pressure and allowed to stand to crystallize, yielding 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl with a product yield of 68.42%.
[0050] Example 4
[0051] This embodiment provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, the steps of which are as follows:
[0052] (1) Add 2g of p-hydroxycinnamic acid (12.20mmol), 0.12g of anhydrous potassium acetate (1.22mmol), 0.02g of NA-17 and 0.02g of phenothiazine and 35mL of DMF to a four-necked flask equipped with a thermometer, reflux condenser and mechanical stirrer. Heat to 148℃ and react for 2h to obtain a DMF reaction solution containing p-hydroxystyrene.
[0053] (2) Cool the reaction solution to room temperature, add 0.683 g KOH (12.20 mmol) solid and 1.53 g biphenyl dichlorobenzyl (6.1 mmol) to it, and stir in an ice bath for 2.5 h. Add water to the reaction system several times and filter to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0054] (3) The crude product was dissolved in 4 times its volume of petroleum ether, filtered, and a dichloromethane solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl was obtained. The solution was concentrated under negative pressure and allowed to stand to crystallize, yielding 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl with a product yield of 67.28%.
[0055] Example 5
[0056] This embodiment provides a method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, the steps of which are as follows:
[0057] (1) Add 2g of p-hydroxycinnamic acid (12.20mmol), 0.13g of anhydrous sodium carbonate (1.22mmol), 0.05g of NA-17 and 40mL of DMF to a four-necked flask equipped with a thermometer, reflux condenser and mechanical stirrer. Heat to 150℃ and react for 1.5h to obtain a DMF reaction solution containing p-hydroxystyrene.
[0058] (2) Cool the reaction solution to room temperature, add 0.488 g NaOH (12.20 mmol) solid and 1.53 g biphenyl dichlorobenzyl (6.1 mmol) to it, and stir in an ice bath for 2.5 h. Add water to the reaction system several times and filter to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
[0059] (3) The crude product was dissolved in 4 times its volume of petroleum ether, filtered, and a dichloromethane solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl was obtained. The solution was concentrated under negative pressure and allowed to stand to crystallize, yielding 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl with a product yield of 66.84%.
[0060] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features. These modifications or substitutions, or combinations of technical features in the above embodiments that do not conflict with each other, can be made in accordance with the manner described in the embodiments. These modifications, substitutions or combinations do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.
Claims
1. A method for synthesizing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl, characterized in that, Includes the following steps: S1. Add p-hydroxycinnamic acid, polymerization inhibitor and alkaline reagent to organic solvent, heat to carry out dehydration reaction, so that p-hydroxycinnamic acid is converted into p-hydroxystyrene. S2. Cool the reaction system containing p-hydroxystyrene from S1 to room temperature, add an inorganic base and biphenyl dichlorobenzyl, and react in an ice bath. After the reaction is complete, add water to the reaction system multiple times and filter to obtain crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. S3. Dissolve the crude product prepared in S2 completely in an organic solvent, filter, and the filtrate is a solution containing 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl. Crystallize the solution to obtain 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
2. The synthesis method according to claim 1, characterized in that, In S1, the organic solvent is at least one of toluene and N,N-dimethylformamide.
3. The synthesis method according to claim 1, characterized in that, In S1, the alkaline reagent is an inorganic base or an alkaline salt, and the alkaline salt is at least one of anhydrous potassium carbonate, anhydrous potassium acetate, or anhydrous sodium carbonate.
4. The synthesis method according to claim 1, characterized in that, In S1, the polymerization inhibitor is at least one of hydroquinone, p-methoxyphenol, p-tert-butylcatechol, phenothiazine, aluminum N-nitroso-N-phenylhydroxylamine, dialkyl dithiocarbamate, and p-benzoquinone.
5. The synthesis method according to claim 4, characterized in that, The polymerization inhibitor is at least one of N-nitroso-N-phenylhydroxylamine aluminum salt and phenothiazine, and the amount of polymerization inhibitor used is 1-5% of the theoretical mass of p-hydroxycinnamic acid.
6. The synthesis method according to claim 3, characterized in that, In S1, the molar ratio of p-hydroxycinnamic acid to alkaline reagent is 1:0.1-0.5, and the mass ratio of p-hydroxycinnamic acid to polymerization inhibitor is 1:0.01-0.
05.
7. The synthesis method according to claim 1, characterized in that, In S1, when the organic solvent is N,N-dimethylformamide, the dehydration reaction temperature is 148-152℃; when the organic solvent is toluene, the dehydration reaction temperature is 105-110℃.
8. The synthesis method according to claim 7, characterized in that, In S1, when the organic solvent is N,N-dimethylformamide, the dehydration reaction temperature is 150°C; when the organic solvent is toluene, the dehydration reaction temperature is 110°C.
9. The synthesis method according to claim 1, characterized in that, In step S2, the molar ratio of p-hydroxystyrene to inorganic base is 1:0.8-1, and the inorganic base used in step S2 is potassium hydroxide or sodium hydroxide.
10. The synthesis method according to claim 1, characterized in that, In S3, the organic solvent is at least one of dichloromethane, petroleum ether, and ethyl acetate, and the amount used is 4-10 times the volume of the crude 4,4'-bis((4-vinylphenoxy)methyl)-1,1'-biphenyl.
11. The synthesis method according to claim 1, characterized in that, In S3, the crystallization process of the solution includes: rotary evaporation or negative pressure evaporation of organic solvent, recovery of organic solvent, cooling, solid-liquid separation, and washing with anhydrous ethanol.