A benzocyclobutene-functionalized organosilicon compound and its preparation method

By preparing organosilicon compounds functionalized with benzocyclobutene, the problem of high dielectric loss of existing resins under high frequency conditions has been solved, realizing the application of low dielectric materials suitable for interlayer packaging of 5G/6G high frequency PCB boards and chips.

CN113512054BActive Publication Date: 2026-05-05TIANNUO PHOTOELECTRIC MATERIAL
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
TIANNUO PHOTOELECTRIC MATERIAL
Filing Date
2021-05-20
Publication Date
2026-05-05

AI Technical Summary

Technical Problem

Existing benzocyclobutene resin materials have high dielectric loss under high frequency conditions, making it difficult to meet the requirements of 5G/6G electronic components. The dielectric constant and dielectric loss of existing commercial DVSBCB resin cannot meet the application requirements under high frequency and high speed conditions.

Method used

Using organosilicon compounds functionalized with benzocyclobutene, polymers with excellent thermal stability and dielectric properties are prepared by reacting vinylsilane, 4-(1,1-dimethyl-1-hydrosilyl)benzocyclobutene, and chloroplatinic acid. These polymers are then used for interlayer packaging of high-frequency PCBs and chips.

Benefits of technology

It achieves dielectric loss on the order of 10⁻⁴ under high-frequency conditions, possesses excellent thermal stability and dielectric properties, is suitable for interlayer packaging of 5G/6G high-frequency PCB boards and chips, and has low material cost and is easy to mass-produce.

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Abstract

This invention relates to the field of chemical materials technology, specifically to an organosilicon compound functionalized with benzocyclobutene and its preparation method. The structure is shown in formula (I): where n is an integer from 2 to 8; R is one of the following: (a) a substituted or unsubstituted C1-C6 alkyl group; (b) a substituted or unsubstituted aryl group. The compound of this invention, or the polymer obtained by copolymerization with other compounds containing unsaturated bonds, possesses excellent thermal stability, mechanical properties, and dielectric properties, and can be used as a high-temperature resistant material, high-performance composite material, electronic packaging material, and aerospace material; applied to high-frequency PCB boards for 5G / 6G and interlayer packaging of chips, etc. The preparation method of this invention is simple, uses inexpensive and readily available raw materials, has high yield, low cost, and is easy to mass-produce and apply.
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Description

Technical Field

[0001] This invention relates to the field of chemical materials technology, specifically to a benzocyclobutene-functionalized organosilicon compound and its preparation method. Background Technology

[0002] Benzocyclobutene (BCB) materials have found wide application in electronic packaging due to their excellent high and low temperature resistance, low dielectric constant, low loss, good hermeticity, radiation resistance, and especially excellent film-forming and moisture-resistant properties. BCB monomers are transformed into conjugated diene structures upon heating, and highly cross-linked polymers are obtained through free radical polymerization and Diels-Alder reaction. Dow Chemical Company developed tetramethyldivinylsiloxane-bridged benzocyclobutene (DVSBCB) (US5882836), as shown in the following formula.

[0003]

[0004] Its chemical structure is shown in the figure. This type of resin has low dielectric constant and dielectric loss, and has been widely used in integrated circuit packaging. However, due to the rapid development of high-frequency and high-speed semiconductors, DVSBCB resin is finding it increasingly difficult to meet the requirements of next-generation electronic components for dielectric insulating materials.

[0005] There are numerous reports on benzocyclobutene resins both domestically and internationally in the existing technology field, such as: US5882836, US5217568, US5136069; Journal of Polymer Science, Part A: Polymer Chemistry, 2011, 49, 381-391; Chinese Patent CNL200710111698.4, etc. These resins, prepared using BCB intermediates through hydrosilylation, HECK, or Grignard reactions, exhibit good electrical and thermal properties. However, with the increasing demands for high-frequency and high-speed development, current 5G / 6G technologies require dielectric losses of 10... -4 For low-dielectric materials of this magnitude, the dielectric constant of commercially available DVSBCB resin is 2.65 and the dielectric loss is 10. -3 -10 -2 High-frequency and high-speed conditions limit the application of materials in the semiconductor industry. Therefore, there is an urgent need in this field to develop a dielectric material with a dielectric loss of 10⁻⁶ Ω·cm under high-frequency conditions. -4 High-performance, low-dielectric materials of this magnitude. Summary of the Invention

[0006] The main objective of this invention is to provide an organosilicon compound functionalized with benzocyclobutene and its preparation method.

[0007] To achieve the above objectives, the present invention adopts the following technical solution:

[0008] This invention provides an organosilicon compound functionalized with benzocyclobutene, the structure of which is shown in formula (I):

[0009]

[0010] Where n is an integer between 2 and 8; R is one of the following cases:

[0011] (a) Substituted or unsubstituted C1–C6 alkyl groups;

[0012] (b) Substituted or unsubstituted aryl groups.

[0013] Furthermore, the substitution refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of: C1 to C4 alkyl groups, and unsubstituted phenyl groups.

[0014] The present invention also provides a method for preparing the above-described compounds, comprising the following raw materials: vinylsilane, 4-(1,1-dimethyl-1-hydrosilyl)benzocyclobutene, chloroplatinic acid, and toluene;

[0015] The molar ratio of vinylsilane, 4-(1,1-dimethyl-1-hydro)silylbenzocyclobutene (4-DMHSBCB), and chloroplatinic acid is 1:3.5 to 6:3×10⁻⁶. -3 ~1×10 -2 .

[0016] Furthermore, the method specifically includes the following steps:

[0017] The raw materials are sequentially added to the reactor, and nitrogen gas is introduced for protection for 10-30 minutes. The mixture is then continuously stirred and reacted at a temperature of 60-90°C for 18-60 hours. After the reaction is completed, the mixture is cooled to room temperature. The solvent is removed under a pressure of -0.09 to -0.095 MPa and a temperature of 30-40°C. The mixture is then purified by column chromatography or crystallization to obtain the final product.

[0018] The present invention also provides a method for preparing a polymer of the above-described compound, comprising: heating the compound or a prepolymer containing the compound to 165-200°C for a curing reaction for 2-24 hours.

[0019] Further, the preparation method of the prepolymer containing the compound is as follows: the compound or a mixture containing the compound is added to a naphthalene flask, nitrogen is purged for 10 to 30 minutes, and then the prepolymer is heated to a temperature of 155 to 165°C for 15 to 55 hours. The mixture is then cooled to room temperature. The tricene is removed under a pressure of -0.09 to -0.095 MPa and a temperature of 85 to 90°C to obtain the prepolymer.

[0020] Furthermore, the obtained prepolymer is subjected to a curing reaction, specifically as follows: the obtained prepolymer is prepared into a 0.5-1% toluene solution, homogenized and film-forming at 2000-3000 r / min; heated at 50-60℃ for 8-12 h, heated at 170-180℃ for 3-4 h, heated at 200-210℃ for 2-4 h, heated at 220-230℃ for 2-5 h, and held at 240-250℃ for 1-3 h to obtain the final product.

[0021] Furthermore, the preparation method of the prepolymer containing the compound can also be carried out by the following method: mixing and stirring the mixture containing the compound at a temperature of 50 to 80°C until homogeneous, and keeping it at a pressure of -0.09 to -0.095 MPa and a temperature of 120 to 160°C for 3 to 20 hours.

[0022] Furthermore, the obtained prepolymer is subjected to a curing reaction, specifically by heating the obtained prepolymer in multiple stages to carry out the curing reaction:

[0023] Furthermore, the curing reaction is carried out in four stages: Stage 1: Heat to 150-160℃ and hold for 3-4 hours; Stage 2: Heat to 180-200℃ and hold for 3-5 hours; Stage 3: Heat to 210-220℃ and hold for 1-2 hours; Stage 4: Heat to 240-250℃ and hold for 1-2 hours.

[0024] The present invention also provides the above-described compounds and the applications of the prepolymers prepared by the above-described methods in the processing of 5G / 6G high-frequency PCB boards and chips.

[0025] Compared with the prior art, the present invention has the following advantages:

[0026] This invention provides an organosilicon compound functionalized with benzocyclobutene, the structure of which is shown in formula (I). The compound or the polymer obtained by copolymerization with other compounds containing unsaturated bonds has excellent thermal stability, mechanical properties and dielectric properties, and can be used as high-temperature resistant materials, high-performance composite materials, electronic packaging materials and aerospace materials, etc.; applied to high-frequency PCB boards of 5G / 6G and interlayer packaging of chips, etc.

[0027] The preparation method described in this invention is simple, uses inexpensive and readily available raw materials, has a high yield, low cost, and is easy to apply in large-scale production. Detailed Implementation

[0028] It should be noted that the following detailed descriptions are exemplary and intended to provide further illustration of the invention. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains.

[0029] It should be noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the exemplary embodiments of the present invention. As used herein, the singular form is intended to include the plural form as well, unless the context clearly indicates otherwise. Furthermore, it should be understood that when the terms "comprising" and / or "including" are used in this specification, they indicate the presence of features, steps, operations, and / or combinations thereof.

[0030] To enable those skilled in the art to better understand the technical solution of the present invention, the technical solution of the present invention will be described in detail below with reference to specific embodiments.

[0031] 4-(1,1-dimethyl-1-hydro)silylbenzocyclobutene was purchased from Sichuan Beichuan Ruihui Technology Co., Ltd.

[0032] Example 1:

[0033] Methyl, tris(dimethyl, benzocyclobutenylsilylethyl)silane (MTBCBSES), its chemical structural formula is:

[0034]

[0035] Preparation method of MTBCBSES: In a dry anaerobic flask equipped with a magnetic stirrer, add 5g of methyltrivinylsilane, 25g of 4-DMHSBCB, 200μL of a 0.025M tetrahydrofuran solution (catalyst) H2PtCl6, and 60mL of toluene. The mixture is reacted at 70℃ for 40 hours under a nitrogen atmosphere. Thin-layer chromatography is used to monitor whether the reactant methyltrivinylsilane has reacted completely. After the reaction, the reactants are cooled to room temperature, and 10 times the mass of the reactants are added to precipitate the product. The precipitate is then filtered. The resulting solid (precipitate) is dried in a vacuum drying oven at -0.09 to -0.095 MPa and 90℃ for 12 hours to obtain a paste-like product, which is methyl,tris(dimethyl,benzocyclobutenylsilylethyl)silane (MTBCBSES), with a yield of 92%. The structure is characterized as follows:

[0036] 1 H NMR(600MHz, CDCl3)δ(ppm):7.38-7.36(d,3H,ArH),7.32(s,3H,ArH),7.10-7.09(d,3H,ArH),3.21(s,12H,-CH2CH 2- ),0.51-0.74(m,12H,Si-CH2CH2-Si),0.21(s,18H,Si-(CH3)2),0.1(s,3H,Si-CH3).

[0037] Example 2

[0038] Phenyl, tris(dimethyl, benzocyclobutenylsilylethyl)silane (PTBCBSES), its chemical structural formula is:

[0039]

[0040] Preparation method of PTBCBSES: In a dry anaerobic flask equipped with a magnetic stirrer, add 8g of phenyltrivinylsilane, 30g of 4-DMHSBCB, 200μL of a 0.025M tetrahydrofuran solution of H2PtCl6 (catalyst), and 60mL of toluene. The mixture is reacted at 90℃ for 60 hours under a nitrogen atmosphere. Thin-layer chromatography is used to monitor whether the reactant phenyltrivinylsilane has reacted completely. After the reaction, the reactants are cooled to room temperature, and 10 times the mass of the reactants are added to precipitate the product. The precipitate is then filtered. The resulting solid (precipitate) is dried in a vacuum drying oven at -0.09 to -0.095 MPa and 90℃ for 12 hours to obtain a paste-like product, which is phenyl,tris(dimethyl,benzocyclobutenylsilylethyl)silane (PTBCBSES), with a yield of 86%. The structure is characterized as follows:

[0041] 1 H NMR(600MHz,CDCl3)δ(ppm):7.38-7.32(m,5H,ArH),7.29(s,3H,ArH),7.10-7.09(m,6H,ArH),3.19(s,12H,-CH2CH 2- ),0.46-0.64(m,12H,Si-CH2CH2-Si),0.20(s,18H,Si-(CH3)2).

[0042] Example 3

[0043] Methyl, tris(dimethyl, benzocyclobutenylsilylpropyl)silane (MTBCBSPS), its chemical structural formula is:

[0044]

[0045] Preparation method of MTBCBSPS: In a dry anaerobic flask equipped with a magnetic stirrer, add 5-8 g of methyltriallylsilane, 20-30 g of 4-DMHSBCB, 200 μL of a 0.025 M tetrahydrofuran solution (catalyst) H₂PtCl₆, and 60 mL of toluene. The mixture is reacted at 80 °C for 24 hours under a nitrogen atmosphere. Thin-layer chromatography is used to monitor whether the reactant methyltriallylsilane has reacted completely. After the reaction, the reactants are cooled to room temperature, and 10 times the mass of the reactants are added to precipitate the product. The precipitate is then filtered. The resulting solid (precipitate) is dried in a vacuum drying oven at -0.09 to -0.095 MPa and 90 °C for 12 hours to obtain a paste-like product, which is methyl,tris(dimethyl,benzocyclobutenylsilylpropyl)silane (MTBCBSPS), with a yield of 87%. The structure is characterized as follows:

[0046] 1 H NMR(600MHz,CDCl3)δ(ppm):7.38-7.36(d,3H,ArH),7.32(s,3H,ArH),7.10-7.09(d,3H,ArH),3.18(s,12H,-CH2CH 2- ),0.37-0.82(m,18H,Si-CH2-CH2-CH2-Si),0.25(s,18H,Si-(CH3)2),0.12(s,3H,Si-CH3).

[0047] Example 4

[0048] Phenyl, tris(dimethyl, benzocyclobutenylsilylpropyl)silane (PTBCBSPS), its chemical structural formula is as follows:

[0049]

[0050] Preparation method of PTBCBSPS: In a dry anaerobic flask equipped with a magnetic stirrer, add 5-8 g of phenyltriallylsilane, 20-30 g of 4-DMHSBCB, 200 μL of a 0.025 M tetrahydrofuran solution (catalyst) H₂PtCl₆, and 60 mL of toluene. The mixture is reacted at 80 °C for 60 hours under a nitrogen atmosphere. Thin-layer chromatography is used to monitor whether the phenyltriallylsilane reacts completely. After the reaction, the reactants are cooled to room temperature, and 10 times the mass of ethanol is added to precipitate the product. The precipitate is then filtered. The resulting solid (precipitate) is dried in a vacuum drying oven at -0.09 to -0.095 MPa and 90 °C for 12 hours to obtain a paste-like product, which is phenyl,tris(dimethyl, benzocyclobutenylsilylpropyl)silane (PTBCBSPS), with a yield of 87%. The structure is characterized as follows:

[0051] 1 H NMR(600MHz, CDCl3)δ(ppm):7.41-7.34(m,6H,ArH),7.29(s,3H,ArH),7.08-7.01(d,5H,ArH),3.19(s,12H,-CH2CH 2- ),0.37-0.80(m,18H,Si-CH2-CH2-CH2-Si),0.26(s,18H,Si-(CH3)2),0.11(s,3H,Si-CH3).

[0052] Example 5

[0053] The preparation method of the bulk polymer of MTBCBSES is as follows: add the monomer MTBCBSES into an anaerobic bottle, purge with nitrogen for 30 minutes (to remove oxygen from the system), and then heat to 160℃ for 25 hours to cure the reaction, thereby obtaining the bulk polymer of MTBCBSES, PMTBCBSES.

[0054] Dielectric testing revealed that PMTBCBSES exhibited a dielectric constant of 2.61–2.67 and a dielectric loss of 0.0005–0.0009 GHz between 1 GHz and 40 GHz. 5% The temperature is 457℃; the coefficient of thermal expansion is 37ppm / ℃@20℃.

[0055] Example 6

[0056] The preparation method of MTBCBSES polymer is as follows: 3g of MTBCBSES and 20mL of dried trimethylbenzene are added to an anaerobic flask, nitrogen is purged for 30 minutes (to remove moisture and oxygen from the system), and then the mixture is heated to 165℃ for a prepolymerization reaction for 50h. After cooling to room temperature, the reacted material is obtained. The reacted material is then subjected to a pressure of -0.09 to -0.095MPa and a temperature of 85℃ to remove trimethylbenzene (evaporation until no trimethylbenzene distillation is observed) to obtain the MTBCBSES prepolymer. The prepolymer is prepared into a 0.5% toluene solution and coated onto a silicon wafer using a spin coater at 3000r / min. The coating is heated to 50℃ for 12h, then to 180℃ and held for 4h, then to 200℃ and held for 4h, then to 220℃ and held for 2h, and finally to 250℃ and held for 2h to obtain a PMTBCBSES cured film.

[0057] Dielectric tests showed that PMTBCBSES had a dielectric constant of 2.61–2.67 and a dielectric loss of 0.0005–0.0009 in the range of 1 GHz to 40 GHz; and a coefficient of thermal expansion of 37 ppm / ℃ at 20℃.

[0058] Example 7

[0059] The preparation method of MTBCBSES / tetramethyldivinylsiloxane-bridged benzocyclobutene (DVSBCB) polymer is as follows: 2g of MTBCBSES and 10g of 25% DVSBCB are mixed and stirred evenly at 80℃, poured into a preheated polytetrafluoroethylene mold, and vacuumed in a vacuum oven to remove air bubbles. After holding at a pressure of -0.09 to -0.095MPa and a temperature of 120℃ for 12h (until all air bubbles are removed), the product is cured in four stages: the first stage (slowly) is heated to 160℃ and held for 4h; the second stage (slowly) is heated to 200℃ and held for 4h; the third stage (slowly) is heated to 220℃ and held for 2h; and the fourth stage (slowly) is heated to 250℃ and held for 2h, which is the final curing step to obtain the MTBCBSES / DVSBCB composite material.

[0060] Dielectric tests showed that the MTBCBSES / DVSBCB cured material had a dielectric constant of 2.59–2.69 and a dielectric loss of 0.0006–0.0011 at 1 GHz to 40 GHz; the coefficient of thermal expansion was 41 ppm / ℃ at 20℃.

[0061] Example 8

[0062] The solution copolymerization preparation method of MTBCBSES / DVSBCB includes the following steps: 1g of MTBCBSES, 10g of 30% DVSBCB and 30-50mL of dried trimethylbenzene are added to an anaerobic flask. Nitrogen gas is purged for 30 minutes (to remove moisture and oxygen from the system). The mixture is then heated to 165℃ for a prepolymerization reaction for 50 hours. After cooling to room temperature, the reacted material is obtained, yielding the MTBCBSES / DVSBCB prepolymer. A spin coater is used to form a film on a silicon wafer at 2000r / min. The film is then heated to 50℃ for 12 hours, then to 180℃ and held for 4 hours, then to 200℃ and held for 4 hours, then to 220℃ and held for 2 hours, and finally to 250℃ and held for 2 hours to obtain the MTBCBSES / DVSBCB cured film.

[0063] Dielectric tests showed that the MTBCBSES / DVSBCB solution polymer cured product had a dielectric constant of 2.59–2.69 and a dielectric loss of 0.0006–0.0011 at 1 GHz to 40 GHz; the coefficient of thermal expansion was 41 ppm / ℃ at 20℃.

[0064] Example 9

[0065] The preparation method of PTBCBSES solution polymer is as follows: 5g of PTBCBSES and 30mL of dried trimethylbenzene are added to an anaerobic flask, nitrogen is purged for 30 minutes (to remove moisture and oxygen from the system), and then the mixture is heated to 165℃ for a prepolymerization reaction for 50h. After cooling to room temperature, the reacted material is obtained. The reacted material is then subjected to a pressure of -0.09 to -0.095MPa and a temperature of 85℃ to remove trimethylbenzene (evaporation until no more trimethylbenzene distills off) to obtain the PTBCBSES prepolymer. The prepolymer is prepared into a 0.5% toluene solution, and a film is formed on a silicon wafer using a spin coater at 2000r / min. The film is then heated to 50℃ for 12h, then to 180℃ and held for 4h, then to 200℃ and held for 4h, then to 220℃ and held for 2h, and finally to 250℃ and held for 2h to obtain a PTBCBSES cured film.

[0066] Dielectric testing showed that the PTBCBSES cured material had a dielectric constant of 2.53–2.67 and a dielectric loss of 0.0005–0.0008 at frequencies ranging from 1 GHz to 40 GHz. 5% The temperature is 462℃; the coefficient of thermal expansion is 38ppm / ℃@20℃.

[0067] Example 10

[0068] The preparation method of PTBCBSPS solution polymer is as follows: 5g PTBCBSPS and 10mL dried trimethylbenzene are added to an anaerobic flask, nitrogen is purged for 30 minutes (to remove moisture and oxygen from the system), and then the mixture is heated to 165℃ for a prepolymerization reaction for 60h. After cooling to room temperature, the reacted material is obtained. The reacted material is then subjected to a pressure of -0.09 to -0.095MPa and a temperature of 85℃ to remove trimethylbenzene (evaporation until no more trimethylbenzene distills off) to obtain the PTBCBSPS prepolymer. The prepolymer is prepared into a 0.5% toluene solution, and a film is formed on a silicon wafer using a spin coater at 3000r / min. The film is then heated to 50℃ for 12h, then to 180℃ and held for 4h, then to 200℃ and held for 4h, then to 220℃ and held for 2h, and finally to 250℃ and held for 2h to obtain a PTBCBSPS cured film.

[0069] Dielectric testing showed that the PTBCBSES cured material had a dielectric constant of 2.53–2.67 and a dielectric loss of 0.0005–0.0008 at frequencies ranging from 1 GHz to 40 GHz. 5% The temperature is 462℃; the coefficient of thermal expansion is 38ppm / ℃@20℃.

[0070] Example 11

[0071] The solution copolymerization preparation method of PTBCBSPS / DVSBCB is as follows: 3g PTBCBSPS, 10g DVSBCB (10-30%) and 40mL dry trimethylbenzene are added to an anaerobic flask. Nitrogen gas is purged for 30 minutes (to remove moisture and oxygen from the system). The mixture is then heated to 165℃ for a prepolymerization reaction for 60h. After cooling to room temperature, the reacted material is obtained, resulting in the PTBCBSPS / DVSBCB prepolymer. The prepolymer is then coated onto a silicon wafer using a spin coater at 2000r / min. The coating is heated to 50℃ for 12h, then to 180℃ and held for 4h, then to 200℃ and held for 4h, then to 220℃ and held for 2h, and finally to 250℃ and held for 2h to obtain the PTBCBSPS / DVSBCB cured film.

[0072] Dielectric testing showed that the PTBCBSPS / DVSBCB cured polymer exhibited a dielectric constant of 2.55–2.67 and a dielectric loss of 0.0004–0.0008 at frequencies ranging from 1 GHz to 40 GHz. 5% The temperature is 453℃; the coefficient of thermal expansion is 39ppm / ℃@20℃.

[0073] All raw materials used in the above embodiments are commercially available products. Unless otherwise specified, the percentages used in the embodiments are mass (weight) percentages or percentages known to those skilled in the art.

[0074] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. An organosilicon compound functionalized with benzocyclobutene, characterized in that, The structure is shown in equation (I): Formula (I) Where n is an integer between 2 and 8; R is one of the following cases: (a) Substituted or unsubstituted C1-C6 alkyl groups; (b) Substituted or unsubstituted phenyl; The substitution refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of: C1-C4 alkyl groups, and unsubstituted phenyl groups.

2. The method for preparing the compound according to claim 1, characterized in that, The raw materials include: vinylsilane, 4-(1,1-dimethyl-1-hydrosilyl)benzocyclobutene, chloroplatinic acid, and toluene; The molar ratio of vinylsilane, 4-(1,1-dimethyl-1-hydrosilyl)benzocyclobutene, and chloroplatinic acid is 1:3.5 to 6:3×10⁻⁶. -3 ~1×10 -2 .

3. The method for preparing the compound according to claim 2, characterized in that, Specifically, the following steps are included: The raw materials are sequentially added to the reactor, and nitrogen gas is introduced for protection for 10–30 minutes. Stirring is then continued for 60–90 minutes. o The reaction continued for 18–60 h at temperature C. After the reaction was complete, it was cooled to room temperature. Then, it was subjected to a pressure of -0.09 to -0.095 MPa and a temperature of 30–40 °C. o Remove the solvent under C conditions, and purify by column chromatography or crystallization to obtain the final product.

4. A method for preparing the polymer of the compound according to claim 1, characterized in that, The compound or prepolymer containing the compound is heated to 165-200°C. o The curing reaction is carried out at C for 2–24 hours.

5. A method for preparing the polymer of the compound according to claim 4, characterized in that, Preparation method of prepolymer containing the compound: Add the compound and trimethylbenzene to an anaerobic flask, purge with nitrogen for 10-30 minutes, and then heat to 155-165°C. o Prepolymerization was carried out at C for 15–55 h, followed by cooling to room temperature; then prepolymerization was carried out at a pressure of -0.09 to -0.095 MPa and a temperature of 85–90 °C. o Under C conditions, trimethylbenzene was removed to obtain the prepolymer.

6. A method for preparing the polymer of the compound according to claim 5, characterized in that, The obtained prepolymer was subjected to a curing reaction, specifically as follows: the obtained prepolymer was prepared into a 0.5-1% toluene solution, and homogenized into a film at 2000-3000 r / min; at 50-60... o Heating at temperature C for 8–12 h, then at 170–180 °C o Heat at C temperature for 3–4 h; at 200–210 °C o Heat at C temperature for 2–4 h; at 220–230 °C o Heating at C temperature for 2–5 h; at 240–250 °C o Keep at C for 1–3 hours to obtain the product.

7. The method for preparing the polymer of the compound according to claim 6, characterized in that, The obtained prepolymer is then subjected to a curing reaction, specifically through the following steps: the obtained prepolymer is heated in multiple stages to carry out the curing reaction. The curing reaction is carried out in four stages: Stage 1: Heating to 150-160°C o Maintain temperature at 3-4 h; Second stage: Increase temperature to 180-200 °C. o Maintain temperature at 3–5 h; Third stage: Increase temperature to 210–220 °C o Maintain temperature at 1–2 h; Fourth stage: Increase temperature to 240–250 °C o Keep at C for 1–2 hours.

8. The application of the compound of claim 1, and the polymer prepared by the method of any one of claims 4-7, in the processing of 5G / 6G high-frequency PCB boards and chips.

Citation Information

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