High temperature resistant coupling agent and its application in polyphenyl ether substrate circuit board

Abstract

The application relates to the technical field of organic silicon materials, in particular to a high-temperature-resistant coupling agent and application of the high-temperature-resistant coupling agent in a polyphenyl ether base material circuit board, wherein the high-temperature-resistant coupling agent has a structure shown in formula I. The high-temperature-resistant coupling agent is prepared by coupling reaction of an o-aminophenol compound and p-phenyloxy iodobenzene to obtain an intermediate, and then reacting the intermediate with chlorosilane in the presence of alkali. The high-temperature-resistant coupling agent contains an aromatic ring structure, a siloxane group and a polar adaptive site at the same time, has high matching degree with polyphenyl ether resin, benzoxazine resin, inorganic fillers and metal foils, can significantly improve the interface bonding force between copper foils and polyphenyl ether base materials, is synthesized by a two-step method, has mild reaction conditions, simple post-treatment, stable yield and less waste, and is suitable for large-scale industrial production.

Description

Technical Field

[0001] This invention relates to the field of organosilicon materials technology, specifically to a high-temperature resistant coupling agent and its application in polyphenylene ether substrate circuit boards. Background Technology

[0002] Polyphenylene oxide (PPO, also known as PPE) is a high-performance thermoplastic engineering plastic. Its core advantages lie in low dielectric loss, high heat resistance, dimensional stability, and chemical corrosion resistance. The mainstream application is modified alloy (MPPO), widely covering key fields such as electronics, automotive, new energy, home appliances, and photovoltaics. Organosilane coupling agents act as molecular bridges in PPO materials, connecting inorganic fillers and the PPO matrix, solving interfacial compatibility issues, and improving the overall performance of the composite material.

[0003] Organosilane coupling agents have inorganic (alkoxysilane) and organophilic (organic) groups (such as amino) at both ends. During material activation, the inorganic group reacts with water to form a silanol group (-Si-OH). The silanol group undergoes dehydration condensation with the hydroxyl groups (·OH) on the surface of the inorganic filler to form a stable Si-OM covalent bond. Simultaneously, the organophilic group reacts chemically or physically with the polyphenylene ether molecular chain, forming a strong chemical bridge.

[0004] Polyphenylene oxide (PPE) PCBs require soldering temperatures exceeding 260°C. Existing organosilane coupling agents exhibit insufficient high-temperature resistance and weak adhesion to PPE and copper foil, easily leading to PCB warping and copper wire detachment, thus affecting product yield. There is an urgent need for a unique molecular structure design that balances heat resistance and adhesion, overcoming the high-temperature bottleneck, enhancing the interfacial adhesion between PPE and copper foil and fillers, improving PCB dimensional stability and solderability, and reducing processing losses. Summary of the Invention

[0005] The purpose of this invention is to provide a high-temperature resistant coupling agent and its application in polyphenylene ether substrate circuit boards, so as to solve the problems mentioned in the background art.

[0006] To achieve the above objectives, the present invention provides the following technical solution: a high-temperature resistant coupling agent, wherein the structural formula of the high-temperature resistant coupling agent is shown in Formula I.

[0007] .

[0008] Wherein, R represents C1 to C3 alkyl, selected from methyl, ethyl, n-propyl, and isopropyl; It is a benzene ring fused in a benzoxazine ring, which may optionally be substituted with an alkyl, alkoxy, halogen, aryl, ester, or cyano group.

[0009] Preferably, R is a methyl group.

[0010] Preferably, the It is an unsubstituted phenyl group.

[0011] Preferably, the It is a phenyl group with a single substitution at the 4- or 5-position, wherein the substituent is selected from methyl, chlorine, phenyl, trifluoromethyl, cyano, or methyl ester.

[0012] Preferably, the It is a phenyl group that is disubstituted at the 4- and 5-positions, wherein the substituent is a methoxy group.

[0013] Preferably, the high-temperature resistant coupling agent is any one of E1, E2, E3, E4, E5, E6, E7, and E8, and the specific structural formulas of each are as follows: .

[0014] On the other hand, the present invention also provides the following technical solution: the preparation method of the above-mentioned high-temperature resistant coupling agent includes the following steps: Compound A of o-aminophenol was coupled with p-phenoxyiodobenzene B in the presence of potassium phosphate and cuprous iodide to obtain compound C; then compound C was reacted with chlorosilane D in the presence of a base to prepare the high-temperature resistant coupling agent.

[0015] The general reaction formula is as follows: .

[0016] Preferably, the coupling reaction is carried out in DMF solvent at a reaction temperature of 80℃~110℃ for a reaction time of 16h~24h. The reaction product is extracted with ethyl acetate, washed with saturated sodium chloride solution, dried, the solvent is evaporated, and the product is recrystallized with ethanol to obtain compound C.

[0017] The compound C and chlorosilane D were reacted in the presence of triethylamine with tetrahydrofuran as solvent under ice bath conditions, followed by reflux reaction, and then post-processed to obtain the high-temperature resistant coupling agent.

[0018] Furthermore, the present invention also provides the application of the above-mentioned high-temperature resistant coupling agent in polyphenylene ether substrate circuit boards.

[0019] Compared with the prior art, the present invention has the following beneficial effects: 1. The high-temperature coupling agent of the present invention contains a rigid aromatic ring structure, a siloxane group and a polar matching site, and has good compatibility and strong interfacial bonding with polyphenylene ether resin, benzoxazine resin, inorganic filler and copper foil.

[0020] 2. The copper foil peel strength of the polyphenylene ether copper-clad laminate made with high-temperature resistant coupling agent is significantly higher than that of the traditional KH-550. It has excellent interface stability after damp heat aging, can stably withstand the processing of polyphenylene ether PCB boards, and can withstand soldering temperatures above 260℃. Attached Figure Description

[0021] Figure 1 E1 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0022] Figure 2 E2 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0023] Figure 3 E3 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0024] Figure 4 E4 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0025] Figure 5 E5 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0026] Figure 6 E6 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0027] Figure 7 E7 is a high-temperature resistant coupling agent. 1 H NMR spectrum.

[0028] Figure 8 E8 is a high-temperature resistant coupling agent. 1 H NMR spectrum. Detailed Implementation

[0029] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0030] Example 1 This embodiment provides a method for preparing a high-temperature resistant coupling agent, including the following steps: S1. In a 500 mL round-bottom flask, 200 mL of DMF solvent was added, followed by 55 mmol of p-phenoxyiodobenzene B1, 50 mmol of o-aminophenol compound A1 (o-aminophenol), 5 mmol of CuI, and 60 mmol of potassium phosphate. The mixture was reacted at 80 °C for 24 h. After the reaction was complete, the product was extracted with ethyl acetate. The resulting organic layer was washed three times with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Finally, the mixture was recrystallized using ethanol as the solvent to obtain compound C1.

[0031] S2. In a 500 ml three-necked flask equipped with a reflux condenser and a dropping funnel, add 50 mmol of compound C1, 200 ml of tetrahydrofuran solvent, and 120 mmol of triethylamine. Stir slowly under ice bath cooling and add 60 mmol of chlorosilane D1. Then reflux at 77 °C for 8 h. After removing the solvent by vacuum distillation, filter with dichloromethane. The filtrate is then distilled under vacuum to obtain high-temperature resistant coupling agent E1.

[0032] The general reaction formula is as follows: Take an appropriate amount of product E1 obtained in Example 1, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 1 , 1 The 1H NMR spectrum shows that δ 0.25ppm (s, 6H) belongs to the methyl hydrogen of -Si(CH3)2-, δ 2.45ppm (s, 2H) belongs to the hydrogen of the two methylene groups on the benzoxazine ring, and δ 6.75ppm~7.35ppm (m, 13H) belongs to the hydrogen atoms on all aromatic rings. The peak positions, peak shapes and integrated areas are in perfect agreement with the target structure E1, proving that the product structure is correct.

[0033] Example 2 Using o-aminophenol compound A2 (2-amino-4-methylphenol) as a raw material, the coupling reaction in S1 was set as follows: temperature 85℃, reaction time 22h, and other reaction conditions were the same as in Example 1, to obtain E2.

[0034] The general reaction formula is as follows: .

[0035] Take an appropriate amount of the product E2 obtained in Example 2, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 2 , 1The 1H NMR spectrum shows that: δ 0.25ppm (s, 6H) belongs to the methyl hydrogen of -Si(CH3)2-, δ 2.30ppm (s, 3H) belongs to the methyl hydrogen at position 4 of the benzoxazine ring, δ 2.40ppm (s, 2H) belongs to the hydrogens of the two methylene groups on the benzoxazine ring, and the multiplets in the range of δ 6.65ppm to 7.40ppm (m, 12H) belong to all the aromatic ring hydrogens. The peak positions, peak shapes, and integrated areas are in perfect agreement with the target structure E1, proving that the product structure is correct.

[0036] Example 3 Using o-aminophenol compound A3 (2-amino-5-chlorophenol) as a raw material, the coupling reaction in S1 was set as follows: temperature 90℃, reaction time 20h, and other reaction conditions were the same as in Example 1, to obtain E3.

[0037] The general reaction formula is as follows: .

[0038] Take an appropriate amount of product E3 obtained in Example 3, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 3 , 1 The 1H NMR spectrum shows that the δ 0.25 ppm (s, 6H) peak belongs to the methyl hydrogen of -Si(CH3)2-, the δ 2.48 ppm (s, 2H) peak belongs to the hydrogen of the two methylene groups on the benzoxazine ring, and the multiplets in the range of δ 6.75 ppm to 7.35 ppm (m, 12H) peaks belong to all the aromatic ring hydrogens. The electron-withdrawing inductive effect of the chlorine atom causes a slight shift in the chemical shift of the aromatic ring hydrogens to the lower field. The peak shape is in perfect agreement with the target structure E3, proving that the product structure is correct.

[0039] Example 4 Using o-aminophenol compound A4 (2-amino-4-phenylphenol) as the raw material, the coupling reaction in S1 was set as follows: temperature 95℃, reaction time 18h, and other reaction conditions were the same as in Example 1, to obtain E4.

[0040] The general reaction formula is as follows: .

[0041] Take an appropriate amount of the product E4 obtained in Example 4, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 4 , 1The 1H NMR spectrum shows that: δ 0.25ppm (s, 6H) belongs to the methyl hydrogen of -Si(CH3)2-, δ 2.45ppm (s, 2H) belongs to the hydrogen of the two methylene groups on the benzoxazine ring, and the multiplets in the range of δ 6.82ppm to 7.52ppm (m, 17H) belong to all aromatic ring hydrogens (including 4-phenyl substituent aromatic ring hydrogens). Due to the increase in the number of aromatic rings, the peak shape in this region is more complex, and the integrated number of hydrogen atoms is significantly more than that in E1 / E2 / E3. The peak shape is completely consistent with the target structure E4, proving that the product structure is correct.

[0042] Example 5 Using o-aminophenol compound A5 (2-amino-4-trifluoromethylphenol) as a raw material, the coupling reaction in S1 was set as follows: temperature 100℃, reaction time 16h, and other reaction conditions were the same as in Example 1, to obtain E5.

[0043] The general reaction formula is as follows: .

[0044] Take an appropriate amount of product E5 obtained in Example 5, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 5 , 1 The 1H NMR spectrum shows that the δ 0.25 ppm (s, 6H) peak belongs to the methyl hydrogen of -Si(CH3)2-, the δ 2.45 ppm (s, 2H) peak belongs to the hydrogen of the two methylene groups on the benzoxazine ring, and the multiplets in the range of δ 6.80 ppm to 7.50 ppm (m, 12H) peaks belong to all the aromatic ring hydrogens. The strong electron-withdrawing effect of the trifluoromethyl group causes the chemical shift of the aromatic ring hydrogens to shift significantly to the lower field. The peak shape is in perfect agreement with the target structure E5, proving that the product structure is correct.

[0045] Example 6 Using o-aminophenol compound A6 (2-amino-4,5-dimethoxyphenol) as a raw material, the coupling reaction in S1 was set as follows: temperature 105℃, reaction time 18h, and other reaction conditions were the same as in Example 1, to obtain E6.

[0046] The general reaction formula is as follows: .

[0047] Take an appropriate amount of the product E6 obtained in Example 6, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 6 , 1The 1H NMR spectrum shows that: δ 0.25ppm (s, 6H) belongs to the methyl hydrogen of -Si(CH3)2-, δ 2.45ppm (s, 2H) belongs to the hydrogen of the two methylene groups on the benzoxazine ring, the two singlets at δ 3.85ppm / 3.80ppm (s, 3H) belong to the methoxy hydrogens at positions 4 and 5 of the benzoxazine ring, and the multiplets in the range of δ 6.35ppm to 7.30ppm (m, 11H) belong to all the aromatic ring hydrogens. The electron-donating effect of the dimethoxy group causes a slight shift of the chemical shift of the aromatic ring hydrogens to a higher field. The peak shape is in perfect agreement with the target structure E6, proving that the product structure is correct.

[0048] Example 7 Using o-aminophenol compound A7 (2-amino-4-cyanophenol) as the raw material, the coupling reaction in S1 was set as follows: temperature 110℃, reaction time 22h, and other reaction conditions were the same as in Example 1, to obtain E7.

[0049] The general reaction formula is as follows: .

[0050] Take an appropriate amount of product E7 obtained in Example 7, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 7 , 1 The 1H NMR spectrum shows that: δ 0.25ppm (s, 6H) belongs to the methyl hydrogen of -Si(CH3)2-, δ 2.45ppm (s, 2H) belongs to the hydrogen of the two methylene groups on the benzoxazine ring, and the multiplets in the range of δ 6.80ppm to 7.40ppm (m, 12H) belong to all the aromatic ring hydrogens. The strong electron-withdrawing effect of the cyano group causes a slight shift in the chemical shift of the aromatic ring hydrogens to the lower field. The peak shape is in perfect agreement with the target structure E7, proving that the product structure is correct.

[0051] Example 8 Using o-aminophenol compound A8 (methyl 3-amino-4-hydroxybenzoate) as a raw material, the coupling reaction in S1 was set as follows: temperature 80℃, reaction time 20h, and other reaction conditions were the same as in Example 1, to obtain E8.

[0052] The general reaction formula is as follows: .

[0053] Take an appropriate amount of the product E8 obtained in Example 8, and use CDCl3 as a solvent to determine its properties on a 400MHz nuclear magnetic resonance spectrometer. 1 H NMR spectrum. Please refer to [reference needed]. Figure 8 , 1The 1H NMR spectrum shows that: δ 0.25ppm (s, 6H) belongs to the methyl hydrogen of -Si(CH3)2-, δ 2.45ppm (s, 2H) belongs to the hydrogen of the two methylene groups on the benzoxazine ring, the singlet at δ 3.87ppm (s, 3H) belongs to the methoxy hydrogen of the methyl ester group, and the multiplets in the range of δ 6.80ppm to 7.75ppm (m, 12H) belong to all the aromatic ring hydrogens. The electron-withdrawing effect of the methyl ester group causes the chemical shift of the aromatic ring hydrogens to a lower field. The peak shape is in perfect agreement with the target structure E8, proving that the product structure is correct.

[0054] This invention also discloses the application of high-temperature resistant coupling agents in polyphenylene ether-based circuit boards. The process for preparing polyphenylene ether-based copper clad laminates based on high-temperature resistant coupling agents includes the following steps: S1. The electronic grade E-glass fiber cloth (7628 electronic grade glass fiber cloth) was calcined in a muffle furnace at 500℃ for 30 minutes to remove wax. After cooling, a mixture of ethanol and water at a volume ratio of 9:1 was used. The pH was adjusted to 4.5 with dilute hydrochloric acid. 1.0% by mass of a high-temperature resistant coupling agent was added and stirred for 30 minutes to hydrolyze the mixture. The glass fiber cloth was then immersed in the solution for 1.5 minutes. After air drying at room temperature, it was dried at 120℃ for 1 hour for later use.

[0055] S2. Wipe the 30μm Ni / Zn plated electrolytic copper foil (Asahi Kasei XYRON PPE G701H) with anhydrous ethanol to remove oil, coat it with a 0.8% (w / w) dilute solution of high-temperature coupling agent in ethanol, and dry it at 80°C for 10 min for later use.

[0056] S3. Dissolve the polyphenylene ether resin in chloroform, then recrystallize it by adding it dropwise to anhydrous ethanol. After filtration, boil it three times with deionized water and dry it under vacuum at 80°C for 12 hours to obtain purified resin.

[0057] S4. Prepare a resin solution with a solid content of 40wt% by mixing NMP, chlorobenzene and chloroform in a volume ratio of 1:1:1. Stir at room temperature for 5 hours until transparent, degas under vacuum of -0.09MPa for 30 minutes and then let it stand for later use.

[0058] S5. The pretreated fiberglass cloth is impregnated with resin at a uniform speed of 0.8 m / min, and then dried sequentially at 95℃ for 10 min, 120℃ for 10 min, 155℃ for 20 min, and 215℃ for 10 min to obtain prepreg. It is used within 24 hours after cooling and cutting.

[0059] S6. Stack the stainless steel template, buffer pad, release film, copper foil, prepreg, copper foil, release film, buffer pad, and template in the following order. After closing the mold, preheat and degas at a low pressure of 5MPa for 5 minutes, then quickly increase the pressure to 20MPa and hot press at 330℃ for 15 minutes. Hold the pressure and cool to below 100℃ before opening the mold. After trimming the edges, the resulting board is vacuum cured at 200℃ for 2 hours and stabilized at 25℃ and 50% humidity for 24 hours to obtain polyphenylene ether-based copper clad laminate.

[0060] Test Example 1: Peel Strength Test 1. Test sample E1 to E8 were used as experimental groups, and commercially available silane coupling agent KH-550 was used as the control group. The corresponding polyphenylene ether-based copper clad laminates were prepared according to the preparation process of polyphenylene ether-based copper clad laminates and obtained as samples.

[0061] 2. Experimental Content and Methods Peel strength test: After placing the polyphenylene oxide-based copper clad laminate in an environment of 25℃ and 50% relative humidity for 24 hours, the peel strength of the copper foil was tested using a SUNDOO electric vertical peeler according to the national standard GB4722-1992. During the test, the copper foil was peeled at a constant rate of 50 mm / min. Each sample was tested at least 4 times, and the average value was taken as the test result. The results are recorded in Table 1.

[0062] Peel strength retention rate test after damp heat aging: The polyphenylene ether-based copper clad laminate was aged in an environment of 85℃ and 85% relative humidity for 96 hours. After aging, the copper foil peel strength was tested according to GB4722-1992 standard. During the test, the copper foil was peeled at a constant rate of 50 mm / min. Each sample was tested at least 4 times, and the average value was taken as the test result. The peel strength retention rate was calculated (retention rate = average peel strength after aging / average peel strength before aging × 100%).

[0063] Soldering thermal shock test: Referring to IPC-TM-650 2.4.13.1 standard, the polyphenylene ether-based copper clad laminate was immersed in a tin bath at 260℃ and 288℃ for 20s respectively. After removal, the appearance of the polyphenylene ether-based copper clad laminate was observed, and phenomena such as delamination, blistering, and warping were recorded. The dimensional change rate was measured. Dimensional change rate (%) = (length after thermal shock - original length before test) / original length before test × 100%. The results are recorded in Table 2.

[0064] Table 1: Peel Strength Test Results Table 2: Results of Solder Solder Thermal Shock Test As shown in Table 1, the copper foil peel strength of the polyphenylene ether-based copper clad laminates prepared by treating with the high-temperature resistant coupling agents E1 to E8 prepared in this invention is significantly higher than that of the comparative example KH-550. Among them, the peel strength of E4, E6, E7, and E8 is greater than 2.0 N / mm, and the peel strength of E6 can reach the highest of 2.2 N / mm. After aging in an environment of 85°C and 85% relative humidity for 96 hours, the peel strength retention rate of all samples of this invention is above 85%, while the peel strength retention rate of the comparative example KH-550 is only 56%. This indicates that the coupling agent of this invention can significantly improve the interfacial bonding force and humid heat stability between polyphenylene ether and copper foil, and effectively solve the problems of weak interfacial bonding force and easy failure under humid heat environment of existing coupling agents.

[0065] As shown in Table 2, the polyphenylene ether-based copper clad laminates prepared by using the high-temperature resistant coupling agents E1 to E8 prepared in this invention showed no delamination, bubbling, or warping after immersion in a tin bath at 260°C for 20 seconds, with a dimensional change rate between 0.06% and 0.09%. After immersion in a tin bath at 288°C for 20 seconds, they still showed no delamination, bubbling, or significant warping, with a dimensional change rate between 0.08% and 0.11%. In contrast, the copper clad laminate treated with the comparative example KH-550 showed slight delamination and slight warping in a tin bath at 260°C, with a dimensional change rate of 0.22%. In a tin bath at 288°C, it showed significant delamination, bubbling, and severe warping, with a dimensional change rate as high as 0.35%. This fully demonstrates that the high-temperature resistant coupling agents of this invention can effectively improve the high-temperature soldering performance and dimensional stability of polyphenylene ether-based copper clad laminates, and can withstand soldering temperatures above 260°C.

[0066] Although embodiments of the invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made to these embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the appended claims and their equivalents.

Claims

1. A high-temperature resistant coupling agent, characterized in that, The structural formula of the high-temperature resistant coupling agent is shown in Formula I. ； Wherein, R represents C1 to C3 alkyl, selected from methyl, ethyl, n-propyl, and isopropyl; It is a benzene ring fused in a benzoxazine ring, which may optionally be substituted with an alkyl, alkoxy, halogen, aryl, ester, or cyano group.

2. The high-temperature resistant coupling agent according to claim 1, characterized in that, R is a methyl group.

3. The high-temperature resistant coupling agent according to claim 1, characterized in that, The It is an unsubstituted phenyl group.

4. The high-temperature resistant coupling agent according to claim 1, characterized in that, The It is a phenyl group with a single substitution at the 4- or 5-position, wherein the substituent is selected from methyl, chlorine, phenyl, trifluoromethyl, cyano, or methyl ester.

5. The high-temperature resistant coupling agent according to claim 1, characterized in that, The It is a phenyl group that is disubstituted at the 4- and 5-positions, wherein the substituent is a methoxy group.

6. The high-temperature resistant coupling agent according to any one of claims 1 to 5, characterized in that, The high-temperature resistant coupling agent is any one of E1, E2, E3, E4, E5, E6, E7, and E8, and the specific structural formulas of each are as follows: 。 7. A method for preparing a high-temperature resistant coupling agent as described in any one of claims 1 to 6, characterized in that, Includes the following steps: Compound A of o-aminophenol was coupled with p-phenoxyiodobenzene B in the presence of potassium phosphate and cuprous iodide to obtain compound C; then compound C was reacted with chlorosilane D in the presence of a base to prepare the high-temperature resistant coupling agent. The general reaction formula is as follows: 。 8. The method for preparing the high-temperature resistant coupling agent according to claim 7, characterized in that, The coupling reaction was carried out in DMF solvent at a temperature of 80℃ to 110℃ for 16h to 24h. The reaction product was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried, the solvent was evaporated, and the product was recrystallized with ethanol to obtain compound C. The compound C and chlorosilane D were reacted in the presence of triethylamine with tetrahydrofuran as solvent under ice bath conditions, followed by reflux reaction, and then post-processed to obtain the high-temperature resistant coupling agent.

9. The application of the high-temperature resistant coupling agent as described in any one of claims 1 to 6 in a polyphenylene ether substrate circuit board.

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