Latent catalyst composition for in-situ synthesis of epoxy molding compound and preparation method thereof
The latent catalyst composition prepared by in-situ synthesis solves the problems of uneven mixing and agglomeration of epoxy molding compound catalysts, achieving more uniform catalytic effect and higher production efficiency.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- HENKEL HUAWEI ELECTRONICS
- Filing Date
- 2026-01-06
- Publication Date
- 2026-04-10
AI Technical Summary
The existing epoxy molding compound catalysts are not mixed evenly, resulting in inconsistent catalytic rates, which affects the encapsulation effect. Furthermore, catalyst agglomeration at room temperature affects product performance and increases the encapsulation defect rate.
A latent catalyst composition was prepared by in-situ synthesis. The latent catalyst and additives were uniformly dispersed in an epoxy molding compound through a one-step reaction. The catalyst release rate was controlled by the different softening points or melting points of the additives, forming a homogeneous system.
This method achieves uniform dispersion of the catalyst, avoids agglomeration, improves catalytic effect, reduces encapsulation defect rate, and increases production efficiency.
Smart Images
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of catalyst technology for semiconductor packaging materials, specifically relating to a latent catalyst composition for in-situ synthesis of epoxy molding compounds and its preparation method. Background Technology
[0002] With the advent of the digital age, the semiconductor industry is also developing rapidly, and the application scenarios and environments for chips are becoming increasingly complex, with chips of different sizes and with different special requirements emerging in an endless stream. The diverse chip structures endow them with different performance characteristics, but also place higher demands on semiconductor packaging materials. Therefore, for different packaging forms, packaging materials need to possess diverse flow properties to meet the packaging requirements of various chips.
[0003] Currently, phenolic-epoxy resin encapsulation is the most common and cost-effective encapsulation method on the market. This material primarily achieves chip encapsulation and protection through the rapid curing of phenolic and epoxy resins at high temperatures. However, the curing rate of phenolic and epoxy resins at high temperatures is very slow and cannot meet encapsulation requirements; therefore, catalytic accelerators are needed to speed up the curing process.
[0004] Commonly used catalysts for epoxy molding compounds mainly include imidazoles and organophosphorus compounds, which can effectively improve the curing rate of phenolic resins and epoxy resins at high temperatures.
[0005] First, in actual production, the catalyst accelerator is dispersed throughout the epoxy molding compound through physical blending, often resulting in uneven mixing. During curing, this uneven catalytic rate leads to uneven mold flow, affecting the encapsulation effect and increasing the product's defect rate. Second, since epoxy molding compound is solid at room temperature, the catalyst accelerator inevitably agglomerates during curing, solidifying before it can exert its catalytic effect. This not only affects the catalytic effect but also impacts product performance after curing residue, posing a risk of product failure during long-term operation.
[0006] Based on this, the latent catalyst synthesized in situ in this invention can effectively solve the above-mentioned defects: First, the latent catalyst and the promoter generated in situ form a homogeneous system with molecular-level mixing, which effectively solves the problem of latent catalyst agglomeration, allowing it to fully exert its latent performance during catalytic solidification. Second, the latent catalyst is encapsulated in different promoters; due to the different softening or melting points of the promoters, the rate of latent catalyst release varies, ultimately resulting in different macroscopic catalytic effects, i.e., exhibiting different levels of latent properties. The latent catalyst prepared by this invention has many advantages, such as simple process, high yield, low cost, no need for post-processing, and direct use, and has good application prospects, effectively improving production efficiency and reducing product defect rate. Summary of the Invention
[0007] To address the technical problems mentioned in the background art, the present invention provides a latent catalyst composition for in-situ synthesis of epoxy molding compounds and its preparation method.
[0008] A latent catalyst composition for in-situ synthesis of epoxy molding compounds, characterized in that the catalyst composition comprises a latent catalyst and an additive; wherein the latent catalyst includes imidazoles and their derivatives, organophosphorus compounds and their derivatives; and the additive includes one or more of epoxy resin, phenolic resin, wax, toughening agent, organic flame retardant and reaction inhibitor.
[0009] The latent catalyst of the present invention is obtained by chemical synthesis and does not react with the promoters; it is obtained by one-step reaction in the in-situ synthesis process, and no other byproducts are generated or the obtained byproducts do not affect the catalytic effect.
[0010] The in-situ synthesis of this invention is carried out at a reaction temperature between 80-200°C and a reaction time of 0.5-6 hours.
[0011] The latent catalyst composition of the present invention has a mass percentage of 1-50%, is a homogeneous system, does not have a phase separation problem, and is a catalytically active mixture.
[0012] The softening point or melting point of the additives of the present invention is not higher than 200°C, and the chemical structure is stable and they do not react chemically with each other.
[0013] The present invention has the following advantages:
[0014] 1. The series of latent catalyst compositions obtained by this method are synthesized in situ and have excellent dispersibility, which can effectively solve the problem of catalyst agglomeration.
[0015] 2. The series of latent catalyst compositions obtained by this method exhibit different catalytic activities and can be applied to epoxy molding compound products with different latency requirements.
[0016] 3. This method has a simple process, high yield, no need for solvents or post-processing, and can be used directly in production, which can greatly improve productivity. Detailed Implementation
[0017] The present invention will now be described in further detail. It should be noted that the embodiments of the present invention are intended to facilitate understanding of the present invention and are not intended to limit it in any way.
[0018] Example 1
[0019] The preparation method of the triphenylphosphine-1,4-benzoquinone adduct intermediate includes the following steps:
[0020] Place 26.2g (0.10mol) of triphenylphosphine and 200g of phenolic resin in a 500ml three-necked round-bottom flask, heat and stir at 150℃ until completely melted;
[0021] Subsequently, stirring was continued, and 13.0 g (0.12 mol) of benzoquinone was slowly added. After the addition was complete, stirring was continued for 3 hours. TLC was used to detect the reaction until it was complete, and the final product of 238.2 g was obtained, with a yield of 99.6%, which was named intermediate 1.
[0022] Example 2
[0023] The preparation method of the tri(p-tolyl)phosphine-1,4-benzoquinone adduct intermediate includes the following steps:
[0024] 30.43 g (0.10 mol) of tris(p-tolyl)phosphine and 200 g of phenolic resin were placed in a 500 ml three-necked round-bottom flask and heated and stirred at 150 °C until completely melted. Then, stirring was continued and 13.0 g (0.12 mol) of benzoquinone was slowly added. After the addition was complete, the reaction was stirred for another 3 h. The reaction was monitored by TLC until the reaction was complete, and the final product of 242.2 g was obtained with a yield of 99.5%, which was named intermediate 2.
[0025] Example 3
[0026] The preparation method of the 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-S-triazine intermediate includes the following steps:
[0027] 13.51 g (0.10 mol) of 1-cyanoethyl-2-methylimidazole and 200 g of phenolic resin were placed in a 500 ml three-necked round-bottom flask and heated and stirred at 150 °C until completely melted. Then, stirring was continued and 19.2 g (0.15 mol) of ethylene cyanide was slowly added. After the addition was completed, the reaction was stirred for another 6 h. The reaction was monitored by TLC until the reaction was complete, and the final product of 230.6 g was obtained with a yield of 99.1%, which was named intermediate 3.
[0028] Example 4
[0029] The preparation method of the tri(p-tolyl)phosphine-1,4-benzoquinone adduct intermediate includes the following steps:
[0030] 30.43 g (0.10 mol) of tris(p-tolyl)phosphine and 200 g of carnauba wax were placed in a 500 ml three-necked round-bottom flask and heated and stirred at 150 °C until completely melted. Then, stirring was continued and 13.0 g (0.12 mol) of benzoquinone was slowly added. After the addition was complete, the reaction was stirred for another 3 h. The reaction was monitored by TLC until the reaction was complete, and 241 g of the final product was obtained, with a yield of 99.0%, which was named intermediate 4.
[0031] Performance testing
[0032] Gel time (GT): Gel time is the time required for molding compound to change from liquid phase to gel; the gel time of thermosetting plastics is usually measured using a gel plate (150°C).
[0033] Spiral flow length (SF): Measured according to ASTM D-3123 standard. At 175°C, a certain pressure is applied to inject the molding compound into a specific mold, the pressure is maintained, and the curing time is 2 minutes. The spiral flow length of each resin is then measured.
[0034] Hot hardness (HH): Hot hardness was measured using the standardized ASTM D2240 hardness tester method, and the test time was 90 seconds after curing.
[0035] Glass transition temperature (Tg): The molding compound was molded into cylindrical samples with a diameter of (5±0.2mm)×(5±0.2mm) using a molding machine, and then tested using a thermomechanical analyzer (TMA).
[0036] Flexural strength and modulus: The molding compound was molded into strips of 125±5mm×13±0.5mm×1 / 4 inch using a molding machine, and then tested using ASTM D790-71 and ASTM D-732-85.
[0037] Among these, with other components remaining constant, the shorter the gelation time, the faster the curing rate; the longer the spiral flow length, the smaller the degree of low-temperature curing; the higher the thermal hardness, the higher the degree of curing; and the higher the flexural strength and modulus, the better the curing effect.
[0038] Preparation of epoxy resin composition and molding compound
[0039] Example 5
[0040] At room temperature, 89 parts by weight of silica powder (spherical silica micropowder), 4 parts by weight of phenol-biphenyl-type epoxy resin (NC3000), 2 parts by weight of low-stress epoxy resin (XY650), 3 parts by weight of phenol-biphenyl-type phenolic resin (MEH-7851SS), 0.2 parts by weight of latent catalyst triphenylphosphine-1,4-benzoquinone adduct (TPP-BQ), 0.1 parts by weight of carbon black, 0.4 parts by weight of palm wax, 0.1 parts by weight of toughening agent (CTBN), and 0.2 parts by weight of coupling agent (glycidoxypropyltrimethoxysilane) are mixed evenly; then, the mixture is kneaded and extruded using a twin-screw extruder at 100°C. After cooling, it is ground into a fine powder to obtain the final molding compound.
[0041] Example 6
[0042] The corresponding molding compound was prepared using the same epoxy resin composition as in Example 5, except that the latent catalyst used was an equal part by weight of intermediate 1.
[0043] Example 7
[0044] The corresponding molding compound was prepared using the same epoxy resin composition as in Example 5, except that the latent catalyst used was an equal part by weight of intermediate 2.
[0045] Example 8
[0046] The corresponding molding compound was prepared using the same epoxy resin composition as in Example 5, except that the latent catalyst used was an equal part by weight of intermediate 3.
[0047] Example 9
[0048] The corresponding molding compound was prepared using the same epoxy resin composition as in Example 5, except that the latent catalyst used was an equal part by weight of intermediate 4.
[0049] The obtained molding compound was tested for gelation time, spiral flow length, hot hardness, flexural strength, and modulus, and the corresponding data were obtained. The test results are shown in the table below:
[0050]
[0051] Among these, with other components remaining constant, the shorter the gelation time, the faster the curing rate; the longer the spiral flow length, the smaller the degree of low-temperature curing; the higher the thermal hardness, the higher the degree of curing; and the higher the flexural strength and modulus, the better the curing effect.
[0052] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.
Claims
1. A latent catalyst composition for in-situ synthesis of epoxy molding compounds, characterized in that, The catalyst composition consists of a latent catalyst and an auxiliary agent; Latent catalysts include imidazoles and their derivatives, organophosphorus compounds and their derivatives; The additives are composed of epoxy resin, phenolic resin, wax and toughening agent in any proportion; The catalyst composition is prepared by in-situ synthesis of a latent catalyst in an auxiliary agent.
2. The latent catalyst composition for in-situ synthesis of epoxy molding compounds according to claim 1, characterized in that, The latent catalyst is prepared by chemical synthesis and does not react with the auxiliaries.
3. The latent catalyst composition for in-situ synthesis of epoxy molding compounds according to claim 1, characterized in that, The latent catalyst composition has a mass percentage of 1-50%, is a homogeneous system, does not have phase separation issues, and is a catalytically active mixture.
4. The latent catalyst composition for in-situ synthesis of epoxy molding compounds according to claim 1, characterized in that, The softening point or melting point of the additives is not higher than 200°C and the chemical structure is stable, and they do not react chemically with each other.
5. A method for preparing a latent catalyst composition for in-situ synthesis of epoxy molding compounds according to any one of claims 1-4, characterized in that, The reaction temperature for the in-situ synthesis is between 80-200℃; The reaction is characterized by not producing byproducts, or byproducts not affecting product performance. The reaction time is 0.5-6 hours.