P-hydroxystyrene derivative containing tertiary amine structure and preparation method thereof

Abstract

The invention discloses a p-hydroxystyrene derivative containing a tertiary amine structure, which has the following structure: # imgabs 0 #, wherein R1 is 2-ethyl morpholine, N-methyl-N-ethyl benzylamine, N, N-dimethyl-isopropyl amine, N-ethyl piperidine, 1-ethyl-4-methyl piperazine, 1-methyl-2-methyl piperidine, 3-methylquinine, N-ethyl pyrrolidine, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2-dimethylamino-1-ethyl, 2- the organic solvent is one of triethyl amine, 3-dimethylamino-1-propyl or 3-diethylamino-1-propyl. The organic solvent is one of triethyl amine, 3-dimethylamino-1-propyl and 3-diethylamino-1-propyl. The method is mild in reaction condition, low in cost, low in equipment requirement and suitable for large-scale production.

Description

Technical Field

[0001] The invention relates to the field of photoresists, and in particular to a p-hydroxystyrene derivative containing a tertiary amine structure and a preparation method thereof. Background Art

[0002] Photoresist, also known as photoresist, refers to a corrosion-resistant thin film material whose solubility changes through irradiation or radiation of ultraviolet light, electron beam, particle beam, X-ray, etc. Photoresist is a key material for completing the photolithography process in microelectronics manufacturing, and it determines the level of development of microelectronics technology. The main components of photoresist are polymer resin, photoacid generator, and corresponding additives and solvents. Photoacid generator is a light-sensitive compound that decomposes under light to produce acid (H+). During the post-exposure baking process, these acids will act as catalysts to cause the acid-labile groups hanging on the polymer to fall off, and the photoresist can be dissolved in the developer. In order to increase the contrast of the photoresist and effectively control the diffusion of the acid generated by exposure, it is necessary to add an alkaline neutralizer to the photoresist. The preparation of photoresist is to mix additives such as resin, photoacid generator, alkaline neutralizer, etc. in a solvent. Experimental data show that the distribution of additives in the colloid is uneven, and it is easy to self-condense to form molecular groups, which is an important factor leading to the roughness of the photoresist pattern. To solve this problem, one design idea is to bond the additive to the resin, so that the additive is fixed on the resin and cannot migrate freely, thus avoiding the occurrence of self-agglomeration. Para-hydroxystyrene and its derivatives can be used to synthesize the main film-forming resin material of 248nm photoresist. At present, there is no report on directly bonding the basic group as a neutralizing agent to the main resin with para-hydroxystyrene as the main body. The main reason is that there is no report on the monomer structure of para-hydroxystyrene derivatives containing tertiary amine structure. Summary of the invention

[0003] The object of the present invention is to provide a p-hydroxystyrene derivative containing a tertiary amine structure.

[0004] The invention also provides a method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure.

[0005] The innovation of the present invention is that the present invention provides a method for synthesizing a p-hydroxystyrene derivative containing a tertiary amine structure, using p-hydroxybenzaldehyde as a starting material, first reacting with malonic acid to synthesize p-hydroxystyrene, then directly reacting with succinic anhydride to synthesize 4-oxo-4-(4-vinylphenoxy)butyric acid through a one-pot method, then reacting 4-oxo-4-(4-vinylphenoxy)butyric acid with oxalyl chloride to obtain an acyl chloride compound, and finally reacting with an alcohol containing a tertiary amine structure to obtain a p-hydroxystyrene derivative containing a tertiary amine structure. The method has mild reaction conditions, low cost, low equipment requirements, and is suitable for large-scale production.

[0006] In order to achieve the above-mentioned object of the invention, the technical solution of the present invention is:

[0007] A p-hydroxystyrene derivative containing a tertiary amine structure, characterized in that it has the following structure:

[0008]

[0009] Wherein R1 is one of: 2-ethylmorpholine, N-methyl-N-ethylbenzylamine, N,N-dimethyl-isopropylamine, N-ethylpiperidine, 1-ethyl-4-methylpiperazine, 1-methyl-2-methylpiperidine, 3-methylquinine, N-ethylpyrrolidine, 2-dimethylamino-1-ethyl, triethylamine, 3-dimethylamino-1-propyl, or 3-diethylamino-1-propyl.

[0010] A method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure comprises the following steps:

[0011]

[0012] (1) Compound 1-v is synthesized by the following method: p-hydroxybenzaldehyde is used as a starting material, and a Knoevenagel reaction is carried out with malonic acid in a polar solvent under the action of an organic base catalyst, wherein the molar ratio of p-hydroxybenzaldehyde, malonic acid, and organic base catalyst is 1:1.0-1.5:0.05-0.2, and the mixture is refluxed with an azeotropic solvent at 90±5°C to remove water for 8-10 hours, and then the azeotropic solvent is evaporated, and the p-hydroxybenzaldehyde and azeotropic solvent are re-suspended in water. The molar ratio is 1:2.0-0.5, and the temperature is continued to rise to 120±5°C and stirred for 10-12h to obtain a 1-III reaction solution; then the temperature is lowered to 60±5°C, and succinic anhydride is added to the 1-III reaction solution, wherein the molar ratio of p-hydroxybenzaldehyde to succinic anhydride is 1:1.0-1.5; the reaction is continued at 60±5°C for 2-4h until the reaction is completed to obtain a 1-v reaction solution, and the 1-v reaction solution is crystallized, filtered, washed, and dried to obtain a compound 1-v;

[0013] (2) Compound 1-VI is synthesized by the following method: dissolving the compound 1-v obtained in step (1) in a solvent, wherein the solvent is one or more of an ester, a halogenated hydrocarbon, or an aromatic hydrocarbon solvent, and the weight ratio of the compound 1-v to the solvent is 1:4-6; adding catalyst N,N-dimethylformamide to obtain a mixed solution, wherein the weight ratio of the compound 1-v to N,N-dimethylformamide is 1:0.001-0.01; adding oxalyl chloride dropwise to the mixed solution at 25±5°C, and reacting at 25±5°C for at least 4 hours after the addition is completed to obtain a 1-VI reaction solution; wherein the molar ratio of the compound 1-v to oxalyl chloride is 1:1.0-1.5;

[0014] (3) The para-hydroxystyrene derivative containing a tertiary amine structure is synthesized by the following method: an alcohol containing an R1 structure and a solvent are cooled to 0±5°C and then the 1-VI reaction solution of step (2) is added dropwise. After the addition is completed, stirring is continued at 0±5°C for 2 hours. The mixture is filtered, washed, and the filter cake is collected and then added to water. The mixture is neutralized with an alkali solution to a pH of 8 to 9 to obtain an aqueous solution. The aqueous solution is extracted with a solvent and separated. The organic phase is washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure until there is no fraction to obtain a para-hydroxystyrene derivative containing a tertiary amine structure. The alcohol containing an R1 structure is one of the following: N- Hydroxyethyl morpholine, N-methyl-N-hydroxyethyl benzylamine, N,N-dimethyl isopropanolamine, N-hydroxyethyl piperidine, 1-hydroxyethyl-4-methylpiperazine, 1-methyl-2-piperidinemethanol, 3-quinuclidine, N-hydroxyethyl pyrrolidine, N,N-dimethylethanolamine, N,N-diethylethanolamine, 3-dimethylaminopropanol, 3-diethylaminopropanol; the molar ratio of compound 1-VI and alcohol containing R1 structure in the 1-VI reaction solution is 1:1.0-1.5; the solvent is esters, halogenated hydrocarbons, and aromatic hydrocarbons; the volume ratio of the 1-VI reaction solution and the solvent is 1:2-4.

[0015] Furthermore, in step (1), the polar solvent is N,N-dimethylformamide or N,N-dimethylacetamide.

[0016] Furthermore, the organic base catalyst is morpholine, piperidine, pyrrolidine or 1,3-oxazolidine.

[0017] Furthermore, the azeotropic solvent in step (1) is an alkane or an aromatic hydrocarbon.

[0018] Furthermore, the azeotropic solvent is one or more of n-hexane, cyclohexane, n-heptane, petroleum ether and toluene.

[0019] Furthermore, the solvent is one or more of ethyl acetate, isopropyl acetate, dichloromethane and toluene.

[0020] The beneficial effects of the present invention are:

[0021] 1. The present invention provides a method for synthesizing a p-hydroxystyrene derivative containing a tertiary amine structure; a two-step continuous addition operation is adopted to reduce the separation operation of compound 1-iii and compound 1-vi, thereby reducing the production cost; the method has mild reaction conditions, low equipment requirements, and is conducive to large-scale production. DETAILED DESCRIPTION

[0022] The technical solutions in the embodiments of the present invention will be described clearly and completely below.

[0023] Example 1: A p-hydroxystyrene derivative containing a tertiary amine structure has the following structure:

[0024] Wherein R1 is one of: 2-ethylmorpholine, N-methyl-N-ethylbenzylamine, N,N-dimethyl-isopropylamine, N-ethylpiperidine, 1-ethyl-4-methylpiperazine, 1-methyl-2-methylpiperidine, 3-methylquinine, N-ethylpyrrolidine, 2-dimethylamino-1-ethyl, triethylamine, 3-dimethylamino-1-propyl, or 3-diethylamino-1-propyl.

[0025] Example 2: A method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure, comprising the following steps:

[0026]

[0027] (1) Compound 1-v is synthesized by the following method: p-hydroxybenzaldehyde is used as a starting material, and Knoevenagel reaction is carried out with malonic acid in a polar solvent under the action of an organic base catalyst, the polar solvent is N,N-dimethylformamide, the organic base catalyst is morpholine, the molar ratio of p-hydroxybenzaldehyde, malonic acid and organic base catalyst is 1:1.0:0.05, and refluxes with an azeotropic solvent at 85°C to remove water for 8 hours, and then the azeotropic solvent is evaporated, and the azeotropic solvent is n-hexane; the weight ratio of p-hydroxybenzaldehyde to the azeotropic solvent is 1:2.0, and the temperature is continued to rise to 115°C and stirred for 10 hours to obtain a 1-III reaction solution; then the temperature is lowered to 55°C, and succinic anhydride is added to the 1-III reaction solution, and the molar ratio of p-hydroxybenzaldehyde to succinic anhydride is 1:1.0; the reaction is continued at 55°C for 2 hours until the reaction is completed to obtain a 1-v reaction solution, and the 1-v reaction solution is crystallized, filtered, washed, and dried to obtain compound 1-v;

[0028] (2) Compound 1-VI is synthesized by the following method: dissolving the compound 1-v obtained in step (1) in a solvent, wherein the solvent is ethyl acetate, and the weight ratio of the compound 1-v to the solvent is 1:4; adding catalyst N,N-dimethylformamide to obtain a mixed solution, wherein the weight ratio of the compound 1-v to N,N-dimethylformamide is 1:0.001; adding oxalyl chloride dropwise to the mixed solution at 20°C, and reacting at 20°C for 4 hours after the addition is completed to obtain a 1-VI reaction solution; the molar ratio of the compound 1-v to the oxalyl chloride is 1:1.0;

[0029] (3) A para-hydroxystyrene derivative containing a tertiary amine structure is synthesized by the following method: an alcohol containing an R1 structure and a solvent, wherein the solvent is ethyl acetate, are cooled to 0±5°C and then the 1-VI reaction solution of step (2) is added dropwise. After the addition is completed, stirring is continued at -5°C for 2 hours. The mixture is filtered, washed, and the filter cake is collected and then added to water. The mixture is neutralized with an alkali solution to a pH of 8 to obtain an aqueous solution. The aqueous solution is extracted with a solvent and separated. The organic phase is washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure until there is no fraction to obtain a para-hydroxystyrene derivative containing a tertiary amine structure. The tertiary amine-containing alcohol is one of the following: N-hydroxyethylmorpholine. The molar ratio of compound 1-VI to the alcohol containing an R1 structure in the 1-VI reaction solution is 1:1.0. The volume ratio of the 1-VI reaction solution to the solvent is 1:2.

[0030] Example 3: A method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure, comprising the following steps:

[0031]

[0032] (1) Compound 1-v is synthesized by the following method: p-hydroxybenzaldehyde is used as a starting material, and undergoes a Knoevenagel reaction with malonic acid in a polar solvent under the action of an organic base catalyst, the polar solvent is N,N-dimethylacetamide, the organic base catalyst is piperidine, the molar ratio of p-hydroxybenzaldehyde, malonic acid, and organic base catalyst is 1:1.2:0.1, and refluxes with an azeotropic solvent at 90°C to remove water for 9 hours, and then the azeotropic solvent is evaporated, and the azeotropic solvent is cyclohexane; the weight ratio of p-hydroxybenzaldehyde to the azeotropic solvent is 1:1, and the temperature is continued to rise to 120°C and stirred for 11 hours to obtain a 1-III reaction solution; then the temperature is lowered to 60°C, and succinic anhydride is added to the 1-III reaction solution, and the molar ratio of p-hydroxybenzaldehyde to succinic anhydride is 1:1. The reaction is continued at 60°C for 3 hours until the reaction is completed to obtain a 1-v reaction solution, and the 1-v reaction solution is crystallized, filtered, washed, and dried to obtain compound 1-v;

[0033] (2) Compound 1-VI is synthesized by the following method: dissolving the compound 1-v obtained in step (1) in a solvent, wherein the solvent is isopropyl acetate, and the weight ratio of compound 1-v to the solvent is 1:5; adding catalyst N,N-dimethylformamide to obtain a mixed solution, wherein the weight ratio of compound 1-v to N,N-dimethylformamide is 1:0.005; adding oxalyl chloride dropwise to the mixed solution at 25°C, and reacting at 25°C for 5 hours after the addition is completed to obtain a 1-VI reaction solution; the molar ratio of compound 1-v to oxalyl chloride is 1:1.2;

[0034] (3) A para-hydroxystyrene derivative containing a tertiary amine structure is synthesized by the following method: an alcohol containing an R1 structure and a solvent, wherein the solvent is isopropyl acetate, are cooled to 0°C and then the 1-VI reaction solution of step (2) is added dropwise. After the addition is completed, stirring is continued at 0°C for 2 hours. The mixture is filtered, washed, and the filter cake is collected and then added to water. The mixture is neutralized with an alkali solution to a pH of 8.5 to obtain an aqueous solution. The aqueous solution is extracted with a solvent and separated. The organic phase is washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure until there is no fraction to obtain a para-hydroxystyrene derivative containing a tertiary amine structure. The tertiary amine-containing alcohol is N-methyl-N-hydroxyethylbenzylamine. The molar ratio of compound 1-VI to the alcohol containing an R1 structure in the 1-VI reaction solution is 1:1.2. The volume ratio of the 1-VI reaction solution to the solvent is 1:3.

[0035] Example 4: A method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure, comprising the following steps:

[0036]

[0037] (1) Compound 1-v is synthesized by the following method: p-hydroxybenzaldehyde is used as a starting material, and Knoevenagel reaction is carried out with malonic acid in a polar solvent under the action of an organic base catalyst, wherein the polar solvent is N,N-dimethylformamide, the organic base catalyst is pyrrolidine, the molar ratio of p-hydroxybenzaldehyde, malonic acid and organic base catalyst is 1:1.5:0.2, and the mixture is refluxed with an azeotropic solvent at 95°C to remove water for 10 hours, and then the azeotropic solvent is evaporated, wherein the azeotropic solvent is n-heptane; the weight ratio of p-hydroxybenzaldehyde to the azeotropic solvent is 1:0.5, and the temperature is continuously raised to 125°C and stirred for 12 hours to obtain a 1-III reaction solution; the temperature is then lowered to 65°C, and succinic anhydride is added to the 1-III reaction solution, wherein the molar ratio of p-hydroxybenzaldehyde to succinic anhydride is 1:1.5; the reaction is continued at 65°C for 4 hours until the reaction is completed to obtain a 1-v reaction solution, and the 1-v reaction solution is crystallized, filtered, washed and dried to obtain compound 1-v;

[0038] (2) Compound 1-VI is synthesized by the following method: Compound 1-v obtained in step (1) is dissolved in a solvent, the solvent is dichloromethane, and the weight ratio of compound 1-v to solvent is 1:6; catalyst N,N-dimethylformamide is added to obtain a mixed solution, the weight ratio of compound 1-v to N,N-dimethylformamide is 1:0.01, oxalyl chloride is added dropwise to the mixed solution at 30°C, and after the addition is completed, the mixture is reacted at 30°C for 6 hours to obtain a 1-VI reaction solution; the molar ratio of compound 1-v to oxalyl chloride is 1:1.5;

[0039] (3) The following synthesis method is adopted for the para-hydroxystyrene derivative containing a tertiary amine structure: alcohol containing R1 structure and solvent, the solvent is dichloromethane, the temperature is lowered to 5°C, and then the 1-VI reaction solution of step (2) is added dropwise. After the addition is completed, stirring is continued at 5°C for 2 hours, filtered, washed, and the filter cake is collected and added to water, and then neutralized with alkali solution to pH 9 to obtain an aqueous solution, the aqueous solution is added with solvent extraction, and the organic phase is washed with saturated NaCl solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure until there is no fraction to obtain the para-hydroxystyrene derivative containing a tertiary amine structure; the tertiary amine-containing alcohol is N,N-dimethylisopropanolamine; the molar ratio of compound 1-VI and the alcohol containing R1 structure in the 1-VI reaction solution is 1:1.5; the volume ratio of the 1-VI reaction solution and the solvent is 1:4.

[0040] Example 5: Referring to Example 1:, the azeotropic solvent is an alkane or an aromatic hydrocarbon, and the azeotropic solvent is one or more of n-hexane, cyclohexane, n-heptane, petroleum ether, and toluene; the solvent is an ester, a halogenated hydrocarbon, or an aromatic hydrocarbon, and the solvent is one or more of ethyl acetate, isopropyl acetate, dichloromethane, and toluene.

[0041] Examples 6 to 14: The alcohol containing the R1 structure in Example 1 is replaced by N-hydroxyethylpiperidine, 1-hydroxyethyl-4-methylpiperazine, 1-methyl-2-piperidinemethanol, 3-quinuclidine, N-hydroxyethylpyrrolidine, N,N-dimethylethanolamine, N,N-diethylethanolamine, 3-dimethylaminopropanol, and 3-diethylaminopropanol to obtain p-hydroxystyrene derivatives containing tertiary amine structures.

[0042] The nuclear magnetic resonance characterization of Example 2 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H),5.47(d d,1H),4.20(t,2H),3.65(dt,4H),2.86-2.80(m,2H),2.80-2.75(m,2H),2.72-2.65(m,2H),2.55(t,4H).

[0043] The nuclear magnetic resonance characterization of Example 3 is as follows: 1H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,6H),7.32-7.22(m,15H),7.08-7.02(m,6H),6.77(t,3H),5.57(dd,3 H),5.47(dd,3H),4.22(t,6H),3.69(s,1H),3.68-3.59(m,5H),2.88(t,6H),2.83-2.75(m,6H),2.72-2.65(m,6H).

[0044] The nuclear magnetic resonance characterization of Example 4 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1 H),5.57(dd,1H),5.47(dd,1H),4.89(qt,1H),2.86-2.67(m,6H),1.34(d,3H).

[0045] The NMR characterization of Example 6 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H),5.47(dd, 1H),4.22(t,2H),2.83-2.75(m,4H),2.72-2.65(m,2H),2.58(td,4H),1.53(dddd,4H),1.49-1.40(m,2H).

[0046] The NMR characterization of Example 7 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H), 5.47(dd,1H),4.21(t,2H),2.85(t,2H),2.82-2.75(m,2H),2.72-2.65(m,2H),2.62-2.47(m,8H).

[0047] The NMR characterization of Example 8 is as follows: 1H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H),5.47(dd,1H),4.14-4.02(m,2H),3.16-3. 07(m,1H),2.89-2.81(m,1H),2.81-2.74(m,2H),2.74-2.66(m,2H),2 .55-2.47(m,1H),2.33(d,3H),1.88-1.74(m,2H),1.62-1.41(m,4H).

[0048] The nuclear magnetic resonance characterization of Example 9 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H) ,5.47(dd,1H),4.78(dt,1H),2.96-2.68(m,10H),2.17(dt,1H),1.79(ddt,2H),1.67(ddt,2H).

[0049] The NMR characterization of Example 10 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H),5.47(dd,1H) ,4.22(t,2H),2.97-2.90(m,4H),2.86-2.80(m,2H),2.80-2.75(m,2H),2.72-2.65(m,2H),1.89-1.79(m,4H).

[0050] The NMR characterization of Example 11 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57 (dd,1H),5.47(dd,1H),4.25(t,2H),3.18(t,2H),2.83-2.75(m,2H),2.72-2.65(m,2H).

[0051] The NMR characterization of Example 12 is as follows: 1H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H ),5.47(dd,1H),4.22(t,2H),2.83-2.75(m,4H),2.72-2.64(m,5H),2.63(s,1H),1.05(t,6H).

[0052] The NMR characterization of Example 13 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H),5.47(d d,1H),4.11(t,2H),2.83-2.75(m,2H),2.72-2.65(m,2H),2.62(t,2H),2.28(s,6H),1.90-1.81(m,2H).

[0053] The NMR characterization of Example 14 is as follows: 1 H NMR (400MHz, Chloroform-d): δ7.48-7.42(m,2H),7.08-7.02(m,2H),6.77(t,1H),5.57(dd,1H),5.47(dd, 1H),4.13(t,2H),2.83-2.75(m,2H),2.72-2.65(m,6H),2.65-2.60(m,3H),1.88-1.80(m,2H),1.02(t,6H).

[0054] The compounds reacted in Examples 2 to 4 and 6 to 14 are 1 to 12 in the following formula:

[0055]

[0056] The described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

Claims

1. A p-hydroxystyrene derivative containing a tertiary amine structure, characterized in that: Has the following structure: Wherein R1 is one of: 2-ethylmorpholine, N-methyl-N-ethylbenzylamine, N,N-dimethyl-isopropylamine, N-ethylpiperidine, 1-ethyl-4-methylpiperazine, 1-methyl-2-methylpiperidine, 3-methylquinine, N-ethylpyrrolidine, 2-dimethylamino-1-ethyl, triethylamine, 3-dimethylamino-1-propyl, or 3-diethylamino-1-propyl.

2. A method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure as claimed in claim 1, characterized in that: The following steps are involved: (1) Compound 1-v is synthesized by the following method: p-hydroxybenzaldehyde is used as a starting material, and a Knoevenagel reaction is carried out with malonic acid in a polar solvent under the action of an organic base catalyst, wherein the molar ratio of p-hydroxybenzaldehyde, malonic acid, and organic base catalyst is 1:1.0-1.5:0.05-0.2, and the mixture is refluxed with an azeotropic solvent at 90±5°C to remove water for 8-10 hours, and then the azeotropic solvent is evaporated, and the p-hydroxybenzaldehyde and azeotropic solvent are re-suspended in water. The molar ratio is 1:2.0-0.5, and the temperature is continued to rise to 120±5°C and stirred for 10-12h to obtain a 1-III reaction solution; then the temperature is lowered to 60±5°C, and succinic anhydride is added to the 1-III reaction solution, wherein the molar ratio of p-hydroxybenzaldehyde to succinic anhydride is 1:1.0-1.5; the reaction is continued at 60±5°C for 2-4h until the reaction is completed to obtain a 1-v reaction solution, and the 1-v reaction solution is crystallized, filtered, washed, and dried to obtain a compound 1-v; (2) Compound 1-VI is synthesized by the following method: dissolving the compound 1-v obtained in step (1) in a solvent, wherein the solvent is one or more of an ester, a halogenated hydrocarbon, or an aromatic hydrocarbon solvent, and the weight ratio of the compound 1-v to the solvent is 1:4-6; adding catalyst N,N-dimethylformamide to obtain a mixed solution, wherein the weight ratio of the compound 1-v to N,N-dimethylformamide is 1:0.001-0.01; adding oxalyl chloride dropwise to the mixed solution at 25±5°C, and reacting at 25±5°C for at least 4 hours after the addition is completed to obtain a 1-VI reaction solution; wherein the molar ratio of the compound 1-v to oxalyl chloride is 1:1.0-1.5; (3) The para-hydroxystyrene derivative containing a tertiary amine structure is synthesized by the following method: an alcohol containing an R1 structure and a solvent are cooled to 0±5°C and then the 1-VI reaction solution of step (2) is added dropwise. After the addition is completed, stirring is continued at 0±5°C for 2 hours. The mixture is filtered, washed, and the filter cake is collected and then added to water. The mixture is neutralized with an alkali solution to a pH of 8 to 9 to obtain an aqueous solution. The aqueous solution is extracted with a solvent and separated. The organic phase is washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure until there is no fraction to obtain a para-hydroxystyrene derivative containing a tertiary amine structure. The alcohol containing an R1 structure is one of the following: N- Hydroxyethyl morpholine, N-methyl-N-hydroxyethyl benzylamine, N,N-dimethyl isopropanolamine, N-hydroxyethyl piperidine, 1-hydroxyethyl-4-methylpiperazine, 1-methyl-2-piperidinemethanol, 3-quinuclidine, N-hydroxyethyl pyrrolidine, N,N-dimethylethanolamine, N,N-diethylethanolamine, 3-dimethylaminopropanol, 3-diethylaminopropanol; the molar ratio of compound 1-VI and alcohol containing R1 structure in the 1-VI reaction solution is 1:1.0-1.5; the solvent is esters, halogenated hydrocarbons, and aromatic hydrocarbons; the volume ratio of the 1-VI reaction solution and the solvent is 1:2-4.

3. The method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure according to claim 1, characterized in that: The polar solvent in step (1) is N,N-dimethylformamide or N,N-dimethylacetamide.

4. The method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure according to claim 1, characterized in that: The organic base catalyst is morpholine, piperidine, pyrrolidine or 1,3-oxazolidine.

5. The method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure according to claim 1, characterized in that: The azeotropic solvent in step (1) is an alkane or an aromatic hydrocarbon.

6. The method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure according to claim 4, characterized in that: The azeotropic solvent is one or more of n-hexane, cyclohexane, n-heptane, petroleum ether and toluene.

7. The method for preparing a p-hydroxystyrene derivative containing a tertiary amine structure according to claim 1, characterized in that: The solvent is one or more of ethyl acetate, isopropyl acetate, dichloromethane and toluene.

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