Catalyst for synthesizing photosensitive diamine compound

Abstract

The invention belongs to the technical field of synthesis of organic compounds, and provides a catalyst for synthesizing photosensitive diamine compounds. The catalyst is prepared by taking zirconium oxychloride, palladium chloride, potassium hydroxide and metal sodium as raw materials through continuous reaction, has excellent catalytic activity and small pollution, and can be recycled after the reaction is finished, so that the production cost is greatly saved.

Description

Technical Field

[0001] The invention belongs to the technical field of organic compound synthesis, and particularly relates to a catalyst for synthesizing photosensitive diamine compounds. Background Art

[0002] Polyimides (PI) have the characteristics of high temperature resistance, high strength, and high dielectric properties. What is important is that they can be converted into stable polyimides by reheating with various precursors (such as polyamic acid, polyamide ester, and polyisoimide, etc.), thereby introducing photosensitive groups through salts or esters, and converting them into stable polyimide layers by heating after exposure and development. Polyisoimides have high solubility and can be converted into polyimides through alkaline catalysis, and can also be used in photolithography technology. In early industrial production, the patterning of polyimides was achieved with the help of photoresists, that is, a layer of photoresist was coated on the surface of the polyimide, and after it was photolithographically patterned, the underlying polyimide was treated by chemical etching and other methods, thereby transferring the pattern of the photoresist to the polyimide layer. In order to simplify the patterning process of polyimide, researchers gave polyimide photosensitivity, that is, synthetic photosensitive polyimide (PSPI).

[0003] Photosensitive polyimide is a rapidly developing organic polymer material that has both imide rings and photosensitive groups on the polymer chain, and combines excellent thermal stability, good mechanical, electrical, electrochemical and photosensitive properties. Photosensitive polyimide itself is both a photolithography material and a dielectric material, which greatly reduces the manufacturing process and improves production efficiency.

[0004] In current industrial production, the synthesis process of photosensitive diamine compounds encounters multiple difficulties when using traditional strong base catalysts. First, the reaction process is time-consuming and lengthy, with significant energy consumption and equipment loss, and many side reactions, which poses a huge challenge to the subsequent product purification. Secondly, the preparation of traditional catalysts is highly dependent on sodium hydroxide, and its large-scale use is not only inefficient, but also poses potential safety risks that cannot be ignored. What is more worrying is that after the reaction, the post-treatment of sodium hydroxide needs to be carried out through acid-base neutralization, which is inefficient and difficult to recycle. Third, traditional catalysts have low catalytic efficiency, large usage, high cost, toxicity, difficulty in separation, and cannot be recycled, which further aggravates resource waste and environmental pollution.

[0005] As the chemical industry is gradually developing towards low pollution and high safety, the existing process can no longer meet the industry's stringent requirements for green production. Therefore, it is urgent to explore synthetic routes and seek a greener and more environmentally friendly method to prepare photosensitive diamine compounds. Summary of the invention

[0006] In order to solve the above technical problems, the present invention proposes a catalyst for synthesizing photosensitive diamine compounds. The preparation method of synthesizing photosensitive diamine compounds using the catalyst is simple to operate, the reaction conditions are mild, the catalyst can be recycled, the production cost is reduced, and it is more environmentally friendly.

[0007] The technical solution of the present invention is: the catalyst used for synthesizing the photosensitive diamine compound is a solid superbase catalyst Na-KOH / γ-PdO-ZrO2, which is prepared by the following steps:

[0008] (1) dissolving zirconium oxychloride and palladium chloride in a mass ratio of 1:2.1 to 15.0 in a solvent and mixing them, then adding citric acid in an amount of 1.8 times the total molar amount of cations, synthesizing a gel by a hydrothermal method, and drying at 115 to 125° C.;

[0009] (2) taking the dried gel in (1) and calcining it at 520-580° C. for 3-5 h to prepare a mixed carrier having a zirconium oxide content of 20-40%;

[0010] (3) Under a nitrogen atmosphere, the mixed carrier in (2) is added to a crucible, first heated to 400-550° C., maintained for 2-3 h, then cooled to 350-370° C., potassium hydroxide (20%-40% by weight of the mixed carrier) is added, reacted for 2 h, then cooled to 300-330° C., and metallic sodium (10% by weight of potassium hydroxide) is added in three batches at 20 min, 40 min, and 1 h of reaction time, and the reaction is continued for 1-2 h before stopping to obtain a solid superbase catalyst Na-KOH / γ-PdO-ZrO2.

[0011] Preferably, the solvent in (1) is ethanol, and the cations are zirconium ions and palladium ions.

[0012] The method for preparing a photosensitive diamine compound using the solid superbase catalyst Na-KOH / γ-PdO-ZrO2 specifically comprises the following steps:

[0013] (1) loading a solid superbase catalyst Na-KOH / γ-PdO-ZrO2 into a fixed bed reactor, and maintaining the fixed bed reactor at room temperature or in a heated state;

[0014] (2) dissolving a nitrobenzaldehyde compound and a nitroacetophenone compound in a solvent and introducing the solvent into a fixed bed reactor for reaction;

[0015] (3) After the reaction in (2) is complete, the solution obtained by the reaction is precipitated, filtered, and recrystallized to obtain a photosensitive dinitro compound, the general structural formula of which is as follows:

[0016]

[0017] (4) Adding a photosensitive dinitro compound and Raney Ni to a solvent, passing the mixture into a reaction kettle, heating, absorbing the theoretical amount of hydrogen within 4 to 6 hours, and then performing hydrogenation reduction at a hydrogen pressure of 5 to 10 MPa. After cooling, the pressure is released, and the photosensitive diamine compound is filtered and precipitated to obtain the photosensitive diamine compound, the general structural formula of which is as follows:

[0018]

[0019] Preferably, in (2),

[0020] The solvent is selected from any one or more of methanol, ethanol, and isopropanol; of course, it can also be other alcohol solvents, and is not limited to the above types: all solvents that can achieve the purpose of the present invention are suitable for the present invention;

[0021] The amount of solvent used is 5 to 10 times the theoretical output of the photosensitive diamine compound.

[0022] Preferably, in (2),

[0023] The nitrobenzaldehyde compound is selected from any one of m-nitrobenzaldehyde and p-nitrobenzaldehyde;

[0024] The nitroacetophenone compound is selected from any one of m-nitroacetophenone and p-nitroacetophenone;

[0025] The mass ratio of nitrobenzaldehyde compounds: nitroacetophenone compounds: solid superbase catalyst Na-KOH / γ-PdO-ZrO2 is 5-10:5-10:1.

[0026] Preferably, in (2), the reaction temperature in the fixed bed reactor is controlled at 25-55°C.

[0027] Preferably, in (4), the solvent is selected from any one or more of methanol, ethanol, and isopropanol;

[0028] The amount of solvent used is 5 to 10 times the theoretical output of the photosensitive diamine compound;

[0029] The mass ratio of the photosensitive dinitro compound: Raney Ni: the solvent is 5:1:50.

[0030] Preferably, in (4), the temperature of the reactor is controlled at 50-60°C.

[0031] Compared with the prior art, the present invention has the following advantages and effects:

[0032] (1) The present invention optimizes the preparation and use process of the solid superbase catalyst Na-KOH / γ-PdO-ZrO2, which not only maximizes the utilization of the preparation raw materials, but also ensures that the catalyst can be recycled while being efficient and safe;

[0033] (2) The present invention uses a solid superbase catalyst Na-KOH / γ-PdO-ZrO2 to prepare photosensitive diamine compounds. The reaction conditions are extremely mild. Using a fixed bed reactor as a platform, the reaction can be carried out in a temperature range of 25°C to 55°C, and can even be carried out smoothly at room temperature. This feature greatly reduces energy consumption requirements. More importantly, this method effectively avoids the problem of reaction temperature runaway due to heat transfer efficiency limitations in fixed bed reactors, that is, it prevents the reaction temperature from rising sharply and exceeding the safety limit. The "flying temperature" phenomenon ensures the safety and controllability of the preparation process;

[0034] (3) The present invention combines the synergistic advantages of solid superbase and fixed bed reactor to achieve a significant improvement in reaction efficiency and product yield; at the same time, the method greatly simplifies the operating steps in the traditional process, optimizes the overall production process, and demonstrates its high efficiency and convenience; it is particularly worth mentioning that the solid superbase catalyst used is recyclable, which not only reduces resource consumption but also effectively reduces production costs. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 It is a chemical reaction process diagram in Example 4 of the present invention;

[0036] Figure 2 It is a chemical reaction process diagram in Example 5 of the present invention;

[0037] Figure 3 is the NMR spectrum of 3,3'-diaminochalcone in Example 4 of the present invention;

[0038] Figure 4 This is the NMR spectrum of 4,4'-diaminochalcone in Example 5 of the present invention. DETAILED DESCRIPTION

[0039] In order to enable those skilled in the art to better understand the present invention, the present invention is further described in conjunction with specific implementation methods.

[0040] Example 1 Preparation of solid superbase catalyst Na-KOH / γ-PdO-ZrO2

[0041] The preparation method of the solid superbase catalyst Na-KOH / γ-PdO-ZrO2 is as follows:

[0042] (1) dissolving zirconium oxychloride and palladium chloride in a mass ratio of 1:2.1 in ethanol and mixing them, then adding citric acid in an amount of 1.8 times the total molar amount of cations (zirconium ions and palladium ions), synthesizing a gel by a hydrothermal method, and drying at 115°C;

[0043] (2) taking the dried gel in (1) and calcining it at 520° C. for 3 h to prepare a mixed carrier with a zirconium oxide content of 20%;

[0044] (3) Under a nitrogen atmosphere, the mixed carrier in (2) was added to a crucible, first heated to 400°C, maintained for 2 h, then cooled to 350°C, potassium hydroxide (20% by weight of the mixed carrier) was added, reacted for 2 h, then cooled to 300°C, and metallic sodium (10% by weight of potassium hydroxide) was added in three batches after reacting for 20 min, 40 min, and 1 h, and the reaction was continued for 1 h before stopping to obtain a solid superbase catalyst Na-KOH / γ-PdO-ZrO2.

[0045] Example 2 Preparation of solid superbase catalyst Na-KOH / γ-PdO-ZrO2

[0046] The preparation method of the solid superbase catalyst Na-KOH / γ-PdO-ZrO2 is as follows:

[0047] (1) dissolving zirconium oxychloride and palladium chloride in a mass ratio of 1:15.0 in ethanol and mixing them, then adding citric acid in an amount of 1.8 times the total molar amount of cations (zirconium ions and palladium ions), synthesizing a gel by a hydrothermal method, and drying at 125° C.;

[0048] (2) taking the dried gel in (1) and calcining it at 580° C. for 5 h to prepare a mixed carrier with a zirconium oxide content of 40%;

[0049] (3) Under a nitrogen atmosphere, the mixed carrier in (2) was added to a crucible, first heated to 550°C, maintained for 3 h, then cooled to 370°C, 40% of the mass of the mixed carrier in potassium hydroxide was added, reacted for 2 h, then cooled to 330°C, and metallic sodium 10% of the mass of potassium hydroxide was added in three batches after reacting for 20 min, 40 min, and 1 h, and the reaction was continued for 2 h before stopping to obtain a solid superbase catalyst Na-KOH / γ-PdO-ZrO2.

[0050] Example 3 Preparation of solid superbase catalyst Na-KOH / γ-PdO-ZrO2

[0051] The preparation method of the solid superbase catalyst Na-KOH / γ-PdO-ZrO2 is as follows:

[0052] (1) dissolving zirconium oxychloride and palladium chloride in a mass ratio of 1:10.0 in ethanol and mixing them, then adding citric acid in an amount of 1.8 times the total molar amount of cations (zirconium ions and palladium ions), synthesizing a gel by a hydrothermal method, and drying at 120° C.;

[0053] (2) taking the dried gel in (1) and calcining it at 550° C. for 4 h to prepare a mixed carrier with a zirconium oxide content of 30%;

[0054] (3) Under a nitrogen atmosphere, the mixed carrier in (2) was added to a crucible, first heated to 500°C, maintained for 2.5 h, then cooled to 360°C, 30% of the mass of the mixed carrier in potassium hydroxide was added, reacted for 2 h, then cooled to 320°C, and metallic sodium 10% of the mass of potassium hydroxide was added in three batches after reacting for 20 min, 40 min, and 1 h, and the reaction was continued for 1.5 h before stopping to obtain a solid superbase catalyst Na-KOH / γ-PdO-ZrO2.

[0055] Example 4 Preparation of 3,3'-diaminochalcone

[0056] The preparation method of 3,3'-diaminochalcone, such as Figure 1 As shown in , the steps are as follows:

[0057] (1) 4 g of the solid superbase catalyst Na-KOH / γ-PdO-ZrO2 in Example 1 was placed in a fixed bed reactor and the temperature was raised to 35° C.;

[0058] (2) 30.2 g of m-nitrobenzaldehyde, 33 g of m-nitroacetophenone and 316 g of isopropanol solution were introduced into the solid bed, and the reaction progress was monitored by HPLC until the reaction was complete;

[0059] (3) After the material in (2) is completely reacted, the solution is slowly added to 400 mL of water to precipitate a photosensitive dinitro compound, namely 3,3'-dinitrochalcone. The crude product is filtered out and recrystallized from ethanol to obtain 46.7 g of a white solid. After testing, the yield of the product is 78.4%, the purity is 98.9%, and the melting point is 216°C;

[0060] (4) reducing 3,3'-dinitrochalcone and Raney Ni in 400 ml of ethanol at a hydrogen pressure of 5 to 10 MPa;

[0061] (5) The reactor was maintained at 60° C. and 8 MPa hydrogen pressure, and the theoretical amount of hydrogen was absorbed within 5 h. The pressure was released, and Raney Ni was filtered out while hot. The filtrate was cooled to obtain a photosensitive diamine compound, namely 3,3'-diaminochalcone, and 30.0 g of a white solid was obtained. After testing, the yield of the product was 80.5%, the purity was 98.3%, and the melting point was 132° C.;

[0062] (6) Post-treatment: After the reaction is completed, the unconsumed solid strong base catalyst loaded in the bed of the solid bed reactor is taken out to achieve the recycling of the catalyst and save costs.

[0063] like Figure 3 As shown, 1H-NMR (400MHZ, DMSO) δ7.55 (2H, m, CH=CH), 7.22 (1H, m, H-2), 7.22 (1H, m, H-2'), 7.22 (1H, m, H-5), 7.10 (1H, t, H-5'), 6.96 (1H, m, H-6), 6.96 (1H, m, H-6'), 6.83 (1H, m, H-4), 6.66 (1H, ddd, H-4'), 5.36 (2H, s, NH2), 5.20 (2H, s, NH2). The product 3,3'-diaminochalcone was confirmed to have a correct structure.

[0064] Example 5 Preparation of 4,4'-diaminochalcone

[0065] The preparation method of 4,4'-diaminochalcone, such as Figure 2 As shown in , the steps are as follows:

[0066] (1) 4 g of solid superbase Na-KOH / γ-PdO-ZrO2 was placed in a fixed bed reactor and the temperature was raised to 35°C;

[0067] (2) 30.2 g of m-nitrobenzaldehyde, 33 g of m-nitroacetophenone and 316 g of isopropanol solution were introduced into the solid bed, and the reaction progress was monitored by HPLC until the reaction was complete;

[0068] (3) After the material in (2) is completely reacted, the solution is slowly added to 400 mL of water to precipitate a photosensitive dinitro compound, namely 4,4'-dinitrochalcone, which is recrystallized from ethanol to obtain 45.6 g of a white solid. After testing, the yield of the product is 76.5%, the purity is 99.1%, and the melting point is 269° C.

[0069] (4) reducing 4,4'-dinitrochalcone and Raney Ni in 400 ml of ethanol at a hydrogen pressure of 5 to 10 MPa;

[0070] (5) The reactor was maintained at 60° C. and 8 MPa hydrogen pressure, and the theoretical amount of hydrogen was absorbed within 5 hours. The pressure was released, and Raney Ni was filtered out while hot. The filtrate was cooled and precipitated to obtain a photosensitive diamine compound, namely 4,4'-diaminochalcone, to obtain 29.6 g of a white solid. After testing, the yield of the product was 81.2%, the purity was 98.3%, and the melting point was 178° C.;

[0071] (6) Post-treatment: After the reaction is completed, the unconsumed solid strong base catalyst loaded in the bed of the solid bed reactor is taken out to achieve the recycling of the catalyst and save costs.

[0072] like Figure 4 As shown, 1H-NMR (400MHZ, DMSO) δ7.87 (2H, m, CH=CH), 7.50 (2H, m, H-2), 7.50 (2H, m, H-2'), 6.60 (2H, m, H-3), 6.60 (2H, m, H-3'), 6.01 (2H, s, NH2), 5.74 (2H, s, NH2). The product 4,4'-diaminochalcone was confirmed to have a correct structure.

[0073] In Example 4 and Example 5, the photosensitive dinitro compound in (3) has the following general structural formula:

[0074]

[0075] (5) Medium-photosensitive diamine compounds, the general structural formula of which is as follows:

[0076]

[0077] It can be seen from the above examples that the photosensitive diamine compounds prepared by the method of the present invention have an ideal yield and a purity greater than 98%, and the operation in the solid bed reactor is also simpler and safer. More importantly, the catalyst can be recycled and reused, saving costs, and overcoming the defects of the scheme mentioned in the background technology, such as large catalyst usage, high cost, toxicity, difficulty in separation, and non-recyclability.

[0078] In summary, the catalyst for synthesizing photosensitive diamine compounds provided by the present invention has high catalytic activity, is recyclable and environmentally friendly.

[0079] The above are only preferred embodiments of the present invention, and are not intended to limit the patent scope of the present invention. All equivalent changes and modifications made within the scope of the present invention should still fall within the scope of the present invention.

[0080] Comparative Example 1

[0081] The difference from Example 4 and Example 5 is that the catalyst used in this comparative example is 4g KOH / γ-PdO, and the rest is the same as Example 4 and Example 5. The product yield is 71.6% and the purity is 96.5%.

[0082] The preparation method of the catalyst KOH / γ-PdO in this comparative example comprises the following steps:

[0083] (1) dissolving palladium chloride in ethanol at a mass ratio of 1:5 and mixing the mixture, then adding citric acid in an amount of 1.5 times the total molar amount of cations (palladium ions), synthesizing a gel by a hydrothermal method, and drying the mixture at 115°C;

[0084] (2) taking the dried gel in (1) and calcining it at 550° C. for 5 h to prepare a mixed carrier having a palladium oxide content of more than 80%;

[0085] (3) Under a nitrogen atmosphere, the mixed carrier in (2) was added to a crucible, first heated to 500°C, maintained for 4.5 hours, then cooled to 360°C, and potassium hydroxide (30% of the weight of the mixed carrier) was added, reacted for 2 hours, then cooled to 320°C, and the reaction was continued for 1.5 hours before stopping to obtain the catalyst KOH / γ-PdO.

[0086] Comparative Example 2

[0087] The difference from Example 4 and Example 5 is that the catalyst used in this comparative example is 4g KOH / ZrO2, and the rest is the same as Example 4 and Example 5. The product yield is 72.9% and the purity is 97.1%.

[0088] The preparation method of the catalyst KOH / ZrO2 in this comparative example comprises the following steps:

[0089] (1) dissolving zirconium oxychloride in ethanol at a mass ratio of 1:10.0 and mixing, then adding citric acid in an amount of 1.5 times the total molar amount of cations (zirconium ions), synthesizing a gel by a hydrothermal method, and drying at 130° C.;

[0090] (2) taking the dried gel in (1) and calcining it at 550° C. for 4 h to prepare a mixed carrier with a zirconium oxide content of 80%;

[0091] (3) Under a nitrogen atmosphere, the mixed carrier in (2) was added to a crucible, first heated to 500°C, maintained for 2.5 h, then cooled to 360°C, and potassium hydroxide (30% of the mass of the mixed carrier) was added, reacted for 2 h, then cooled to 320°C, and the reaction was continued for 1.5 h before stopping to obtain the catalyst KOH / ZrO2.

[0092] Comparative Example 3

[0093] The difference from Example 4 and Example 5 is that the catalyst used in this comparative example is 4g NaOH / γ-PdO, and the rest is the same as Example 4 and Example 5. The product yield is 69.0% and the purity is 98.1%.

[0094] The preparation method of the catalyst NaOH / γ-PdO in this comparative example comprises the following steps:

[0095] (1) dissolving palladium chloride in ethanol at a mass ratio of 1:10.0 and mixing, then adding citric acid in an amount of 1.8 times the total molar amount of cations (palladium ions), synthesizing a gel by a hydrothermal method, and drying at 120°C;

[0096] (2) taking the dried gel in (1) and calcining it at 550° C. for 4 h to prepare a palladium oxide carrier;

[0097] (3) Under a nitrogen atmosphere, the carrier in (2) was added to a crucible, first heated to 500°C, maintained for 2.5 h, then cooled to 360°C, 30% of the carrier mass of sodium hydroxide was added, reacted for 2 h, then cooled to 320°C, and the reaction was continued for 1.5 h before stopping to obtain the catalyst NaOH / γ-PdO.

[0098] Comparative Example 4

[0099] The difference from Example 4 and Example 5 is that the catalyst used in this comparative example is 4g Na-NaOH / γ-PdO, and the rest is the same as Example 4 and Example 5. The product yield is 72.4% and the purity is 96.4%.

[0100] The preparation method of the catalyst Na-NaOH / γ-PdO in this comparative example comprises the following steps:

[0101] (1) dissolving palladium chloride in ethanol at a mass ratio of 1:10.0 and mixing, then adding citric acid in an amount of 1.8 times the total molar amount of cations (palladium ions), synthesizing a gel by a hydrothermal method, and drying at 120°C;

[0102] (2) taking the dried gel in (1) and calcining it at 550° C. for 4 h to prepare a palladium oxide carrier;

[0103] (3) Under a nitrogen atmosphere, the carrier in (2) was added to a crucible, first heated to 500°C, maintained for 2.5 h, then cooled to 360°C, 30% of the carrier mass of sodium hydroxide was added, reacted for 2 h, then cooled to 320°C, and metallic sodium was added in three batches after reacting for 20 min, 40 min, and 1 h, and the reaction was continued for 1.5 h before stopping to obtain the catalyst Na-NaOH / γ-PdO.

[0104] Comparative Example 5

[0105] The difference from Example 4 and Example 5 is that the catalyst used in this comparative example is 4g Na-KOH / γ-ZrO2, and the rest is the same as Example 4 and Example 5. The product yield is 73.6% and the purity is 96.8%.

[0106] The preparation method of the catalyst Na-KOH / γ-ZrO2 in this comparative example comprises the following steps:

[0107] (1) dissolving zirconium oxychloride in ethanol at a mass ratio of 1:10.0 and mixing the mixture, then adding citric acid in an amount of 1.8 times the total molar amount of cations (zirconium ions), synthesizing a gel by a hydrothermal method, and drying the mixture at 120° C.;

[0108] (2) taking the dried gel in (1) and calcining it at 550° C. for 4 h to prepare a zirconium oxide carrier;

[0109] (3) Under a nitrogen atmosphere, the carrier in (2) was added to a crucible, first heated to 500°C, maintained for 2.5 h, then cooled to 360°C, 30% of the carrier mass of potassium hydroxide was added, reacted for 2 h, then cooled to 320°C, and metallic sodium 10% of the potassium hydroxide mass was added in three batches after reacting for 20 min, 40 min, and 1 h, and the reaction was continued for 1.5 h before stopping to obtain the catalyst Na-KOH / γ-ZrO2.

Claims

1. A catalyst for synthesizing photosensitive diamine compounds, which is mainly prepared by the following steps: (1) dissolving zirconium oxychloride and palladium chloride in a mass ratio of 1:2.1 to 15.0 in ethanol and mixing them, then adding citric acid in an amount of 1.8 times the total molar amount of cations, synthesizing a gel by a hydrothermal method, and drying at 115 to 125° C.; (2) taking the dried gel in (1) and calcining it at 520-580° C. for 3-5 h to prepare a mixed carrier having a zirconium oxide content of 20-40%; (3) Under a nitrogen atmosphere, the mixed carrier in (2) is added to a crucible, first heated to 400-550° C., maintained for 2-3 h, then cooled to 350-370° C., potassium hydroxide (20%-40% by weight of the mixed carrier) is added, reacted for 2 h, then cooled to 300-330° C., metallic sodium (10% by weight of potassium hydroxide) is added in batches, the reaction is continued for 1-2 h and then stopped to obtain a solid superbase catalyst Na-KOH / γ-PdO-ZrO2.

2. Use of the catalyst as claimed in claim 1 in the synthesis of photosensitive diamine compounds.

3. A method for synthesizing a photosensitive diamine compound using the catalyst according to claim 2, characterized in that: The main steps include: (1) loading a solid superbase catalyst Na-KOH / γ-PdO-ZrO2 into a fixed bed reactor, and maintaining the fixed bed reactor at room temperature or in a heated state; (2) dissolving a nitrobenzaldehyde compound and a nitroacetophenone compound in a solvent and introducing the solvent into a fixed bed reactor for reaction; (3) After the reaction in (2) is complete, the solution obtained by the reaction is precipitated, filtered, and recrystallized to obtain a photosensitive dinitro compound; (4) Adding a photosensitive dinitro compound and Raney nickel to a solvent, passing the mixture into a reaction kettle, heating the mixture, absorbing a theoretical amount of hydrogen within 4 to 6 hours, and then performing hydrogenation reduction at a hydrogen pressure of 5 to 10 MPa. After cooling, the pressure is released, and the photosensitive diamine compound is filtered and precipitated to obtain the photosensitive diamine compound.

4. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: The general structural formula of the photosensitive dinitro compound described in (3) is as follows: The general structural formula of the photosensitive diamine compound described in (4) is as follows:

5. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: (2) The nitrobenzaldehyde compound is selected from any one of m-nitrobenzaldehyde and p-nitrobenzaldehyde; The nitroacetophenone compound is selected from any one of m-nitroacetophenone and p-nitroacetophenone; The mass ratios of nitrobenzaldehyde compounds: nitroacetophenone compounds: solid superbase catalyst Na-KOH / γ-PdO-ZrO2 are 5-10:5-10:1 respectively.

6. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: (2) in (4), The solvents are selected from any one or more of methanol, ethanol and isopropanol; In the two steps, the amount of solvent used is 5 to 10 times the theoretical output of the photosensitive diamine compound.

7. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: (2), the reaction temperature in the fixed bed reactor is controlled at 25-55°C.

8. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: The mass ratio of photosensitivity dinitro compound: Raney nickel: solvent is 5:1:

50.

9. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: (4) The heating temperature is controlled at 50-60°C.

10. The method for preparing a photosensitive diamine compound according to claim 3, characterized in that: The main steps include: (1) 4 g of solid superbase catalyst Na-KOH / γ-PdO-ZrO2 was placed in a fixed bed reactor and the temperature was raised to 35°C; (2) 30.2 g of m-nitrobenzaldehyde and 33 g of m-nitroacetophenone were dissolved in 316 g of isopropanol and introduced into a fixed bed reactor for reaction; (3) After the reaction is complete, the resulting solution is slowly added to 400 mL of water, and then recrystallized from ethanol to obtain 3,3'-dinitrochalcone; (4) 31.5 g of 3,3'-dinitrochalcone obtained in (2) and 6.3 g of Raney nickel were added to 400 mL of ethanol, introduced into a reactor, and hydrogen was absorbed within 5 h at 60° C. and 8 MPa of hydrogen pressure to perform hydrogenation reduction. After the reaction was complete, heating was stopped, the pressure was released, the Raney nickel was filtered out while hot, and the mixture was cooled to room temperature and precipitated to obtain 3,3'-diaminochalcone.

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