Silane monomer, benzocyclobutene silicone resin, device and preparation method

Abstract

The present application discloses silane monomer, benzocyclobutene silicone resin, device and preparation method, belonging to the field of polymer materials. The chemical structural formula of the silane monomer is as follows: wherein, R1, R2, R3, R4, R5 are independently selected from the following groups: H, alkyl, alkoxy, alkenyl, phenyl; R6, R7, R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group or hydrolyzed group, and at least one of R6, R7, R8 is a hydrolyzed group; the hydrolyzed group is selected from substituted or unsubstituted amino, alkoxy, acyloxy or -Cl. The silane monomer can undergo a hydrolysis condensation reaction to synthesize a benzocyclobutene silicone resin with adjustable viscosity, without the need for a prepolymerization process, which is convenient for large-scale batch production.

Description

Technical Field

[0001] The present invention relates to the field of polymer materials, and in particular to silane monomers, benzocyclobutene silicone resins, devices and preparation methods. Background Art

[0002] Benzocyclobutene (BCB) has excellent electrical insulation, high thermal stability, and high hydrophobicity. Silicone polymers have good heat resistance and easy processability. However, the film-forming properties of silicone polymers are generally poor. By modifying silicone polymers with benzocyclobutene, silicone resins containing benzocyclobutene functional groups with relatively good film-forming properties can be obtained.

[0003] The related technology first synthesizes silane containing silacyclobutane and benzocyclobutene groups, and uses the silane containing silacyclobutane and benzocyclobutene groups as the starting reaction monomer for ring-opening polymerization to obtain a linear silicone resin with a main chain of carbosilane and a side chain of benzocyclobutene.

[0004] In the process of implementing the present disclosure, the inventors found that there are at least the following problems in the prior art:

[0005] In the related art, silane containing silacyclobutane and benzocyclobutene groups is used as the starting reaction monomer. However, the synthesis conditions of the starting reaction monomer are harsh, the synthesis steps are complicated, and the reaction yield is low. It is not only difficult to mass produce, but also the cost is high. Summary of the invention

[0006] In view of this, the embodiments of the present disclosure provide silane monomers, benzocyclobutene silicone resins, electrical devices and preparation methods, which can solve the above-mentioned technical problems.

[0007] Specifically, the following technical solutions are included:

[0008] On the one hand, the present disclosure provides a silane monomer, the chemical structure of the silane monomer is as follows:

[0009]

[0010] Wherein, R1, R2, R3, R4, and R5 are independently selected from the following groups: H, alkyl, alkoxy, alkenyl, and phenyl;

[0011] R6, R7, and R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group, or hydrolyzable group, and at least one of R6, R7, and R8 is the hydrolyzable group;

[0012] The hydrolyzable group is selected from substituted or unsubstituted amino, alkoxy, acyloxy, or -Cl.

[0013] In some possible implementations, the hydrolyzable group is selected from dimethylamino, diethylamino, C1-C4 alkoxy, or C1-C4 acyloxy.

[0014] In some possible implementations, the substituted C1-C6 alkyl group and the substituted C2-C6 alkenyl group both have a first substituent, and the first substituent is a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, an unsubstituted phenyl group, or a phenyl group in which 1 to 3 hydrogen atoms on the benzene ring are substituted with a C1-C4 alkyl group;

[0015] The substituted phenyl group has a second substituent selected from a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, or an unsubstituted phenyl group.

[0016] In some possible implementations, the chemical structural formula of the silane monomer is as follows:

[0017]

[0018] In some possible implementations, the chemical structural formula of the silane monomer is as follows:

[0019] or

[0020] or

[0021]

[0022] On the other hand, an embodiment of the present disclosure provides a benzocyclobutene silicone resin, which is prepared by subjecting any one of the above-mentioned silane monomers to a hydrolysis condensation reaction.

[0023] In some possible implementations, the chemical structural formula of the benzocyclobutene silicone resin is as follows:

[0024]

[0025] Wherein, n is an integer greater than or equal to 0;

[0026] R' is selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group.

[0027] In some possible implementations, the substituted C1-C6 alkyl group and the substituted C2-C6 alkenyl group both have a first substituent, and the first substituent is selected from a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, an unsubstituted phenyl group, or a phenyl group in which 1 to 3 hydrogen atoms on the benzene ring are substituted with a C1-C4 alkyl group;

[0028] The substituted phenyl group has a second substituent selected from a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, or an unsubstituted phenyl group.

[0029] In some possible implementations, the chemical structural formula of the benzocyclobutene silicone resin is as follows:

[0030]

[0031] Wherein, x, y and z are all integers greater than or equal to 0;

[0032] R`` is selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl.

[0033] In some possible implementations, the substituted C1-C6 alkyl group and the substituted C2-C6 alkenyl group both have a first substituent, and the first substituent is selected from a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, an unsubstituted phenyl group, or a phenyl group in which 1 to 3 hydrogen atoms on the benzene ring are substituted with a C1-C4 alkyl group;

[0034] The substituted phenyl group has a second substituent selected from a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, or an unsubstituted phenyl group.

[0035] In another aspect, the present disclosure provides a method for preparing any of the above-mentioned silane monomers, the method for preparing the silane monomer comprising:

[0036] Under an inert atmosphere and alkaline environment, a vinyl-containing siloxane and 4-bromobenzocyclobutene are subjected to a Heck reaction in a dry solvent having a first catalyst and an acid-binding agent to obtain the silane monomer;

[0037] Wherein, the chemical structural formula of the vinyl-containing siloxane is as follows:

[0038]

[0039] R6, R7, and R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group, or hydrolyzable group, and at least one of R6, R7, and R8 is the hydrolyzable group;

[0040] The hydrolyzable group is selected from dimethylamino, diethylamino, C1-C4 alkoxy, or C1-C4 acyloxy.

[0041] In some possible implementations, the first catalyst is selected from palladium acetate, palladium chloride, tetrakis(triphenylphosphine)palladium, palladium-carbon catalyst, and diphenylphosphinoferrocenepalladium dichloride.

[0042] In some possible implementations, the acid binding agent is selected from at least one of triethylamine, diethylamine, potassium carbonate, sodium carbonate, pyridine, and imidazole.

[0043] In some possible implementations, the drying solvent is selected from at least one of benzene, acetonitrile, tetrahydrofuran, dioxane, N,N-dimethylformamide, and N,N-dimethylacetamide.

[0044] In some possible implementations, the reaction temperature of the Heck reaction is 50° C.-120° C., and the reaction time is 4 hours-48 hours.

[0045] In another aspect, the present disclosure provides a method for preparing any one of the above-mentioned benzocyclobutene silicone resins, the method for preparing the benzocyclobutene silicone resin comprising:

[0046] Providing at least one silane monomer, wherein the silane monomer is as described in the first aspect above;

[0047] Under the catalytic action of the second catalyst, the at least one silane monomer is subjected to a hydrolysis-condensation reaction in an aqueous solution to obtain the benzocyclobutene silicone resin.

[0048] In some possible implementations, at least one silane monomer containing a single hydrolyzable group is used to carry out the hydrolysis condensation reaction.

[0049] In some possible implementations, the second catalyst is an acid catalyst or a base catalyst;

[0050] The acid catalyst is selected from at least one of formic acid, acetic acid, hydrochloric acid, phosphoric acid and sulfuric acid;

[0051] The alkaline catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium phosphate, ammonia water, diethylamine, triethylamine, pyridine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, imidazole, N-methylimidazole, N-ethylimidazole, and benzyltrimethylammonium hydroxide.

[0052] In some possible implementations, the reaction temperature of the hydrolysis condensation reaction is 15°C-120°C.

[0053] In some possible implementations, the method for preparing the benzocyclobutene silicone resin further includes:

[0054] After the hydrolysis and condensation reaction is completed, removing the second catalyst from the reaction product system to obtain an organic phase;

[0055] The organic phase is dried and filtered to obtain the benzocyclobutene silicone resin.

[0056] On the other hand, an embodiment of the present disclosure provides a device having a resin layer, wherein the resin layer is prepared by using any one of the above-mentioned benzocyclobutene silicone resins.

[0057] The beneficial effects of the technical solution provided by the embodiments of the present disclosure include at least:

[0058] 1. The silane monomer provided by the embodiment of the present disclosure has a benzocyclobutene group, and based on the use of a hydrolyzable group, it can undergo a hydrolysis-condensation reaction to synthesize a benzocyclobutene silicone resin. When synthesizing the benzocyclobutene silicone resin, the viscosity of the benzocyclobutene silicone resin can be adaptively adjusted by adjusting the ratio of the silane monomer and the ratio of the hydrolyzable functional groups contained therein, thereby avoiding the use of a prepolymerization process to adjust its viscosity, and effectively reducing the difficulty and cost of preparing the benzocyclobutene silicone resin. In addition, by hydrolyzing and condensing silane monomers with different hydrolyzable groups to synthesize the benzocyclobutene silicone resin, it is not only easy to control the molecular weight and viscosity of the benzocyclobutene silicone resin, but also the conditions of the hydrolysis-condensation reaction are mild, simple to operate, low in cost, and convenient for large-scale batch production.

[0059] 2. Vinyl-containing siloxane and 4-bromobenzocyclobutene can undergo Heck reaction under specific conditions to prepare silane monomers. The reaction conditions of the Heck reaction are mild and easy to control, and the raw materials used are stable, simple and easy to obtain, making the preparation process of the silane monomer simple and easy to control, and convenient for large-scale production.

[0060] 3. The benzocyclobutene silicone resin provided in the embodiments of the present disclosure combines benzocyclobutene with organosiloxane, and the number of benzocyclobutene groups and organosiloxane groups can be easily regulated, so that the benzocyclobutene silicone resin has at least the following advantages: excellent electrical insulation, excellent dielectric properties, high thermal stability, high hydrophobicity, easy processability, easy film-forming property, etc.

[0061] 4. The preparation method of the benzocyclobutene silicone resin provided in the embodiment of the present disclosure can mildly realize the synthesis of the benzocyclobutene silicone resin by co-hydrolyzing the silane monomers with different hydrolysis groups, without the need for a prepolymerization process, which is not only simple in process and low in cost, but also convenient for large-scale production. In addition, the degree of polymerization of the benzocyclobutene silicone resin can be controlled, solving the problem of poor film-forming properties caused by the small molecular weight of the benzocyclobutene silicone resin in the related art; the proportion of the benzocyclobutene group in the benzocyclobutene silicone resin can also be easily regulated, so that the benzocyclobutene silicone resin has excellent dielectric properties, heat resistance and adhesion. DETAILED DESCRIPTION

[0062] In order to make the technical solutions and advantages of the present disclosure more clear, the embodiments of the present disclosure will be described in further detail below.

[0063] Benzocyclobutene (BCB) has excellent electrical insulation, high thermal stability, and high hydrophobicity. Silicone polymers have good heat resistance and easy processability. However, the film-forming properties of silicone polymers are generally poor. By modifying silicone polymers with benzocyclobutene, silicone resins containing benzocyclobutene functional groups with relatively good film-forming properties can be obtained.

[0064] The related technology first synthesizes silane containing silacyclobutane and benzocyclobutene groups, and uses the silane containing silacyclobutane and benzocyclobutene groups as the starting reaction monomer for ring-opening polymerization to obtain a linear silicone resin with a main chain of carbosilane and a side chain of benzocyclobutene.

[0065] However, in the related art, silane containing silacyclobutane and benzocyclobutene groups is used as the starting reaction monomer. However, the synthesis conditions of the starting reaction monomer are harsh, the synthesis steps are cumbersome, and the reaction yield is low. It is not only difficult to mass produce, but also the cost is high.

[0066] In addition, Dow Chemical and others have also developed a typical siloxane containing a dibenzocyclobutene group, the chemical structure of which is shown below:

[0067]

[0068] However, the molecular weight of the siloxane with the above chemical structure is small, but the boiling point is very high, and the purification process is cumbersome. Especially when it comes to ultra-low metal ion residue and ultra-low halogen residue requirements for applications in the field of microelectronics, the resin monomer purification process requires higher requirements. If the monomer purity is not high, it will have a great impact on the performance of the later resin. In addition, when in use, it is necessary to carry out prepolymerization at a temperature of >160°C, and it can only be used after obtaining a prepolymer with a certain viscosity. However, oxidation reactions are prone to occur during the prepolymerization process, resulting in the generation of by-products, darkening of the color, and affecting the performance of the siloxane. Therefore, the prepolymerization process needs to strictly control its anhydrous and oxygen-free state, and it is also necessary to control the prepolymer product to have a suitable prepolymer molecular weight so that it meets the use requirements and does not gel, which further increases the difficulty of the prepolymerization process.

[0069] On the one hand, the present disclosure provides a silane monomer, the chemical structure of which is as follows:

[0070]

[0071] Wherein, R1, R2, R3, R4, and R5 are independently selected from the following groups: H, alkyl, alkoxy, alkenyl, and phenyl. For example, alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., alkoxy is C1-C6 alkoxy, etc., alkenyl is vinyl, propenyl, butenyl, pentenyl, etc., and phenyl is toluene, benzene ring, etc.

[0072] R6, R7, and R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl (methyl, ethyl, propyl, butyl, pentyl, hexyl), unsubstituted or substituted C2-C6 alkenyl (vinyl, propenyl, butenyl, pentenyl, hexenyl), unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group, or a hydrolyzed group.

[0073] At least one of R6, R7, and R8 is a hydrolyzable group, and the hydrolyzable group is selected from a substituted or unsubstituted amino group, an alkoxy group, an acyloxy group, or -Cl.

[0074] For example, the hydrolyzable group is selected from dimethylamino, diethylamino, C1-C4 alkoxy (methoxy (CH3O-), ethoxy (C2H5O-), propoxy (C3H7O-), butoxy (C4H9O-), etc.), or C1-C4 acyloxy (formyloxy, acetoxy, propionyloxy, butyryloxy, etc.).

[0075] In the silane monomer provided in the embodiments of the present disclosure, as examples, the unsubstituted C1-C6 alkyl groups are, for example, methyl, ethyl, propyl, butyl, pentyl, etc.; the unsubstituted C2-C6 alkenyl groups are, for example, vinyl, propenyl, butenyl, pentenyl, etc.

[0076] In some possible implementations, the substituted C1-C6 alkyl and the substituted C2-C6 alkenyl both have a first substituent, and the first substituent is, for example, a C1-C4 alkyl (e.g., methyl, ethyl, propyl, butyl, etc.), a C2-C4 alkenyl (e.g., ethenyl, propenyl, butenyl), a C2-C4 alkynyl (e.g., ethynyl, propynyl, butynyl), an unsubstituted phenyl, or a phenyl in which 1-3 hydrogen atoms on the benzene ring are substituted by a C1-C4 alkyl.

[0077] In some possible implementations, the substituted phenyl group has a second substituent, and the second substituent is selected from a C1-C4 alkyl group (e.g., methyl, ethyl, propyl, butyl, etc.), a C2-C4 alkenyl group (e.g., ethenyl, propenyl, butenyl), a C2-C4 alkynyl group (e.g., ethynyl, propynyl, butynyl), or an unsubstituted phenyl group.

[0078] As a typical example, the silane monomer provided in the embodiment of the present disclosure has the chemical structural formula shown below:

[0079]

[0080] Among them, any one, any two of R6, R7, and R8 are hydrolyzable groups, or all three are hydrolyzable groups. When two or three hydrolyzable groups are included, the hydrolyzable groups may be the same or different.

[0081] In the embodiments of the present disclosure, any one of R6, R7, and R8 can be a hydrolyzable group to constitute a silane monomer having a single hydrolyzable group; any two of R6, R7, and R8 can be hydrolyzable groups (the two hydrolyzable groups can be the same or different) to constitute a silane monomer having a double hydrolyzable group; and R6, R7, and R8 can all be hydrolyzable groups (the three hydrolyzable groups can be the same or different) to constitute a silane monomer having a trihydrolyzable group.

[0082] As an example, the silane monomer is a silane monomer having a single hydrolyzed group, and the hydrolyzed group is a methoxy group. In this case, the chemical structure of the silane monomer is as follows:

[0083]

[0084] As another example, the silane monomer is a silane monomer having a double hydrolyzable group, and the hydrolyzable group is a methoxy group. In this case, the chemical structural formula of the silane monomer is as follows:

[0085]

[0086] As another example, the silane monomer is a silane monomer having a trihydrolyzable group, and the hydrolyzable group is a methoxy group. In this case, the chemical structural formula of the silane monomer is as follows:

[0087]

[0088] The silane monomer provided by the embodiment of the present disclosure has a benzocyclobutene group, and based on the use of a hydrolyzable group, it is possible to undergo a hydrolysis-condensation reaction to synthesize a benzocyclobutene silicone resin. When synthesizing the benzocyclobutene silicone resin, the viscosity of the benzocyclobutene silicone resin can be adaptively adjusted by adjusting the ratio of the silane monomer and the ratio of the hydrolyzable functional groups contained therein, thereby avoiding the use of a prepolymerization process to adjust its viscosity, and effectively reducing the difficulty and cost of preparing the benzocyclobutene silicone resin. In addition, by hydrolyzing and condensing silane monomers with different hydrolyzable groups to synthesize the benzocyclobutene silicone resin, it is not only easy to control the molecular weight and viscosity of the benzocyclobutene silicone resin, but also the conditions of the hydrolysis-condensation reaction are mild, simple to operate, low in cost, and convenient for large-scale batch production.

[0089] The silane monomer provided by the embodiments of the present disclosure has at least the following advantages compared with the resin monomer of Dow Chemical: small molecular weight, low boiling point, can be purified by ordinary vacuum distillation, and the purity can easily reach electronic grade or microelectronic grade.

[0090] On the other hand, the present disclosure also provides a method for preparing any of the above-mentioned silane monomers, the method for preparing the silane monomer comprising:

[0091] Under an inert atmosphere, a vinyl-containing siloxane is reacted with 4-bromobenzocyclobutene in a dry solvent with a first catalyst and an acid binder to obtain a silane monomer.

[0092] Among them, the chemical structure formula of vinyl-containing siloxane is as follows:

[0093]

[0094] R6, R7, and R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group, or hydrolyzed group, and at least one of R6, R7, and R8 is a hydrolyzed group, and the hydrolyzed group is selected from dimethylamino, diethylamino, C1-C4 alkoxy, or C1-C4 acyloxy. For R6, R7, and R8 here, refer to the above description of R6, R7, and R8 in the silane monomer, which will not be repeated here.

[0095] Vinyl-containing siloxane and 4-bromobenzocyclobutene can undergo Heck reaction under the above-mentioned specific conditions to prepare silane monomers. The reaction conditions of Heck reaction are gentle and easy to control, and the raw materials used are stable, simple and easy to obtain, so that the preparation process of silane monomers is simple and easy to control, and is convenient to large-scale production. Wherein, 4-iodobenzocyclobutene can also replace 4-bromobenzocyclobutene, and can play the same effect as 4-bromobenzocyclobutene. In the reaction process, vinyl-containing siloxane can be made slightly excessive relative to 4-bromobenzocyclobutene, so that 4-bromobenzocyclobutene fully and thoroughly reacts completely.

[0096] The following is a description of the reaction conditions involved in the Heck reaction:

[0097] The Heck reaction is carried out in an inert atmosphere to ensure that the reaction proceeds stably and to prevent undesirable side reactions. In the embodiments of the present disclosure, the inert atmosphere can be provided by nitrogen or argon.

[0098] The Heck reaction continuously generates hydrobromic acid during the reaction process, which has an inhibitory effect on the first catalyst and is not conducive to the reaction proceeding in the forward direction. In the embodiment of the present disclosure, an acid binding agent is added to the reaction system to react with the hydrobromic acid to generate a salt. In other words, the acid binding agent can consume the hydrogen bromide continuously generated during the Heck reaction, which is conducive to the reaction proceeding in the forward direction and improving the reaction yield.

[0099] For example, the acid binding agent used in the embodiment of the present disclosure is selected from at least one of triethylamine, diethylamine, potassium carbonate, sodium carbonate, pyridine, and imidazole.

[0100] In order to improve the reaction efficiency and make the reaction proceed smoothly, the first catalyst is selected from at least one of palladium acetate, palladium chloride, tetrakis(triphenylphosphine)palladium, palladium-carbon catalyst (Pd / C catalyst for short), and diphenylphosphinoferrocene palladium dichloride. Further, in order to make the first catalyst fully active, when used, the first catalyst is used in conjunction with a corresponding ligand. When the first catalyst is palladium acetate, tri(o-methylphenyl)phosphine can be used as its corresponding ligand to promote the Heck reaction to proceed fully.

[0101] The Heck reaction needs to be carried out in a strictly anhydrous environment, so the embodiments of the present disclosure use a dry solvent, that is, the solvent needs to be dried before use, for example, by fractionation, distillation, or dry gas reflux, etc. For example, the dry solvent is selected from at least one of benzene, acetonitrile, tetrahydrofuran, dioxane, N,N-dimethylformamide, and N,N-dimethylacetamide.

[0102] For example, redistilled acetonitrile or redistilled tetrahydrofuran that has been distilled twice or more can be used as the drying solvent.

[0103] In some possible implementations, in order to improve the reaction efficiency of the Heck reaction, the reaction temperature of the Heck reaction is set to 50°C-120°C, for example, 60°C-100°C, for example, 60°C, 70°C, 80°C, 90°C, 100°C, etc.; the reaction time of the Heck reaction is set to 4 hours-48 hours, for example, 6 hours-12 hours.

[0104] After the Heck reaction is completed, the silane monomer can be separated from the reaction product system in the following manner: the reaction product system is filtered twice with silica gel, the filtrate obtained is washed with a non-polar solvent (such as n-hexane, petroleum ether, etc.) for subsequent use, and the obtained organic phase is concentrated by rotary evaporation and purified by vacuum distillation to obtain a high-purity silane monomer.

[0105] On the other hand, the embodiments of the present disclosure further provide a benzocyclobutene silicone resin, which is prepared by subjecting the above-mentioned silane monomer to a hydrolysis condensation reaction.

[0106] By controlling the structure of the silane monomer used, especially controlling the number of hydrolyzed groups contained in the silane monomer, the structure of the synthesized benzocyclobutene silicone resin includes but is not limited to: linear, branch-type, ring-type, or network-type.

[0107] The benzocyclobutene silicone resin provided in the embodiments of the present disclosure combines benzocyclobutene with organosiloxane, and the number of benzocyclobutene groups and organosiloxane groups can be easily regulated, so that the benzocyclobutene silicone resin has at least the following advantages: excellent electrical insulation, excellent dielectric properties, high thermal stability, high hydrophobicity, easy processability, easy film-forming property, etc.

[0108] In some possible implementations, the benzocyclobutene silicone resin can be prepared by the following preparation method:

[0109] providing at least one silane monomer;

[0110] Under the catalytic action of the second catalyst, at least one silane monomer undergoes a hydrolysis condensation reaction in an aqueous solution to obtain a benzocyclobutene silicone resin.

[0111] One, two or more silane monomers can be used for hydrolysis and condensation reaction to obtain the desired benzocyclobutene silicone resin of the embodiment of the present disclosure. The benzocyclobutene silicone resin obtained by co-hydrolysis and condensation reaction of multiple silane monomers has controllable molecular weight, good film-forming property, and is conducive to further thermal curing and cross-linking.

[0112] Among them, at least one silane monomer containing a single hydrolyzable group is used for hydrolysis and condensation reaction, that is, when performing the above hydrolysis and condensation reaction, at least one silane monomer containing a single hydrolyzable group is used as a reaction raw material, and the silane monomer containing a single hydrolyzable group can be used as a capping agent to obtain a benzocyclobutene-capped benzocyclobutene silicone resin. In addition, the silane monomer containing a single hydrolyzable group is used as a capping agent, and its structure is basically consistent with the structure of the hydrolysis main silane monomer, ensuring that the ratio of benzocyclobutene group to silicon atom and vinyl group is 1:1:1.

[0113] Of course, in some possible implementations, silane monomers that do not contain benzocyclobutene groups may be copolymerized to adjust the proportion of benzocyclobutene groups in the benzocyclobutene silicone resin.

[0114] In some possible implementations, a benzocyclobutene silicone resin having a linear structure and benzocyclobutene end-capping can be synthesized by co-hydrolysis polymerization of a silane monomer having a mono-hydrolyzable group and a silane monomer having a di-hydrolyzable group.

[0115] As a typical example, the chemical structure of the benzocyclobutene silicone resin is shown below:

[0116]

[0117] Wherein, n is an integer greater than or equal to 0;

[0118] R' is selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl, 4-vinyl-benzocyclobutene group.

[0119] For example, the substituted C1-C6 alkyl and the substituted C2-C6 alkenyl both have a first substituent, and the first substituent is, for example, a C1-C4 alkyl (e.g., methyl, ethyl, propyl, butyl, etc.), a C2-C4 alkenyl (e.g., ethenyl, propenyl, butenyl), a C2-C4 alkynyl (e.g., ethynyl, propynyl, butynyl), an unsubstituted phenyl, or a phenyl in which 1-3 hydrogen atoms on the benzene ring are substituted by a C1-C4 alkyl.

[0120] Illustratively, the substituted phenyl has a second substituent selected from a C1-C4 alkyl group (e.g., methyl, ethyl, propyl, butyl, etc.), a C2-C4 alkenyl group (e.g., ethenyl, propenyl, butenyl), a C2-C4 alkynyl group (e.g., ethynyl, propynyl, butynyl), or an unsubstituted phenyl group.

[0121] In the above-mentioned benzocyclobutene silicone resin, R' refers to a non-hydrolyzable group, which is derived from the non-hydrolyzable group in the silane monomer and can correspond to R6, R7 or R8 at will, as long as it is a non-hydrolyzable group.

[0122] As an example, the chemical structure of the benzocyclobutene silicone resin is shown below:

[0123]

[0124] The reaction equation of the benzocyclobutene silicone resin is as follows:

[0125]

[0126] It can be seen that the above-mentioned linear benzocyclobutene silicone resin can be prepared by hydrolyzing and condensing the silane monomer having a monohydrolyzable group and the silane monomer having a dihydrolyzable group.

[0127] The silane monomer with a monohydrolyzable group is used as an end-capping agent to perform end-capping, and the silane monomer with a dihydrolyzable group is used as a resin matrix to affect the polymerization degree of the benzocyclobutene silicone resin, that is, the n value. The desired polymerization degree can be obtained by controlling the ratio of the silane monomer with a dihydrolyzable group to the silane monomer with a monohydrolyzable group.

[0128] In some possible implementations, a benzocyclobutene silicone resin having a branched chain network structure can be synthesized by co-hydrolysis polymerization of a silane monomer having a monohydrolyzable group, a silane monomer having a dihydrolyzable group, and a silane monomer having a trihydrolyzable group.

[0129] As another typical example, the chemical structure of the benzocyclobutene silicone resin is shown below:

[0130]

[0131] Wherein, x, y and z are all integers greater than or equal to 0;

[0132] R`` is selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted phenyl.

[0133] For example, the substituted C1-C6 alkyl and the substituted C2-C6 alkenyl both have a first substituent, and the first substituent is, for example, a C1-C4 alkyl (e.g., methyl, ethyl, propyl, butyl, etc.), a C2-C4 alkenyl (e.g., ethenyl, propenyl, butenyl), a C2-C4 alkynyl (e.g., ethynyl, propynyl, butynyl), an unsubstituted phenyl, or a phenyl in which 1-3 hydrogen atoms on the benzene ring are substituted by a C1-C4 alkyl.

[0134] Illustratively, the substituted phenyl has a second substituent selected from a C1-C4 alkyl group (e.g., methyl, ethyl, propyl, butyl, etc.), a C2-C4 alkenyl group (e.g., ethenyl, propenyl, butenyl), a C2-C4 alkynyl group (e.g., ethynyl, propynyl, butynyl), or an unsubstituted phenyl group.

[0135] In the above-mentioned benzocyclobutene silicone resin, R`` refers to a non-hydrolyzable group, which is derived from the non-hydrolyzable group in the silane monomer and can correspond to R6, R7 or R8 at will, as long as it is a non-hydrolyzable group.

[0136] In the chemical structure of the above-mentioned benzocyclobutene silicone resin, the number of hydrolyzable groups contained in the corresponding silane monomer group is determined according to the number of R`` connected to the Si atom in each silane monomer group. For example, when the number of R`` connected to the Si atom in the silane group is two, it means that the silane monomer corresponding to the silane monomer group has one hydrolyzable group; when the number of R`` connected to the Si atom in the silane group is one, it means that the silane monomer corresponding to the silane monomer group has two hydrolyzable groups; when there is no R`` connected to the Si atom in the silane group, it means that the silane monomer corresponding to the silane monomer group has three hydrolyzable groups.

[0137] The wavy line connected to Si in the above chemical structure refers to a group that can undergo hydrolysis, such as dimethylamino, diethylamino, C1-C4 alkoxy, or C1-C4 acyloxy. This means that the hydrolyzable group did not participate in the previous hydrolysis and condensation reaction, and can undergo a new hydrolysis and condensation reaction, so that the chemical structure of the benzocyclobutene silicone resin continues to extend outward and the molecular weight continues to increase.

[0138] As an example, the chemical structure of the benzocyclobutene silicone resin is shown below:

[0139]

[0140] The reaction equation of the benzocyclobutene silicone resin is as follows:

[0141]

[0142] The polymerization degree, that is, the molecular weight, of the benzocyclobutene silicone resin is controlled by the timing of adding the silane monomer containing a monohydrolyzable group. In the embodiment of the present disclosure, the molecular weight of the benzocyclobutene silicone resin may range from 1500 to 200000. At the same time, by controlling the timing of adding the silane monomer containing a monohydrolyzable group and the silane monomer containing a dihydrolyzable group, the chemical structure of the benzocyclobutene silicone resin can be changed, that is, the presence and quantity of the groups x, y, and z can be changed.

[0143] For example, in the chemical structure of the above-mentioned benzocyclobutene silicone resin, the value range of x is 0-50, for example, 1, 5, 10, 20, 30, 40, 45, etc.; the value range of y is 0-50, for example, 1, 5, 10, 20, 30, 40, 45, etc.; the value range of z is 0-50, for example, 1, 5, 10, 20, 30, 40, 45, etc.; and there is at least one of the groups where x, y, and z are located.

[0144] The benzocyclobutene silicone resin provided in the embodiments of the present disclosure can undergo cross-linking polymerization by heating (for example, further cross-linking and curing through Diels-Alder reaction (DA reaction)), and the resulting cross-linked product has controllable viscosity, good heat resistance and electrical properties, high cross-linking density, small free volume, and low dielectric loss (equivalent to DVS-BCB, or better than DVSBCB).

[0145] The benzocyclobutene silicone resin provided in the embodiments of the present disclosure can be used in the fields of microelectronic multi-chip modules (MCM), integrated circuits, optoelectronic devices, aerospace, etc., and can be used directly or modified by adding other organic modifiers or inorganic modifiers.

[0146] For example, the benzocyclobutene silicone resin provided in the embodiments of the present disclosure can be used as a packaging material or an insulating coating layer, and applied to electronic devices or optoelectronic devices such as solar cells, display devices, LEDs, and MEMS. The benzocyclobutene silicone resin provided in the embodiments of the present disclosure can be used as an optical device or optical film material, and can also be used as a low-dielectric interlayer dielectric material, low-dielectric photoresist, patterning material, chip bonding adhesive, etc. in the semiconductor and integrated circuit fields; it can also be used in the preparation of high-performance resin composite materials.

[0147] On the other hand, the embodiments of the present disclosure further provide a method for preparing any of the above-mentioned benzocyclobutene silicone resins, the method for preparing the benzocyclobutene silicone resin comprising:

[0148] Providing at least one silane monomer, the silane monomer is as described above;

[0149] Under the catalytic action of the second catalyst, at least one silane monomer undergoes a hydrolysis condensation reaction in an aqueous solution to obtain a benzocyclobutene silicone resin.

[0150] Wherein, at least one silane monomer containing a single hydrolyzable group is used for the hydrolysis condensation reaction. When two or more silane monomers are used for the hydrolysis condensation reaction, one of the silane monomers can be slightly excessive to allow the other silane monomers to react fully and completely.

[0151] The hydrolysis-condensation reaction is carried out under the catalytic action of a second catalyst. In some possible implementations, the second catalyst is an acid catalyst or a base catalyst; wherein the acid catalyst is selected from at least one of formic acid, acetic acid, hydrochloric acid, phosphoric acid, and sulfuric acid. The acid catalyst can be a diluted acid aqueous solution or a high-purity acid.

[0152] The alkali catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium phosphate, ammonia water, diethylamine, triethylamine, pyridine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, imidazole, N-methylimidazole, N-ethylimidazole, and benzyltrimethylammonium hydroxide. The alkali catalyst can be a diluted aqueous solution or alcohol solution of the alkali.

[0153] When the above hydrolysis condensation reaction is carried out, the reaction system may contain a solvent or may not contain a solvent. Whether a solvent needs to be added can be determined based on the molecular weight requirements of the benzocyclobutene silicone resin: when the benzocyclobutene silicone resin requires a larger molecular weight, a solvent is added for the purpose of diluting the product and raw materials, facilitating stirring to allow for full hydrolysis, making the molecular weight distribution of the hydrolysis product more uniform, making the polymer structure easier to control, and being beneficial to the mechanical properties of the resin. When the benzocyclobutene silicone resin requires a smaller molecular weight, no solvent may be added.

[0154] For example, the solvent suitable for the above-mentioned hydrolysis condensation reaction is selected from at least one of methanol, ethanol, isopropanol, butanol, benzene, toluene, trimethylolbenzene, tetrahydrofuran, alkane solvents (n-hexane, petroleum ether, cyclohexane, etc.), ether, dioxane, dichloromethane, chloroform, N,N-dimethylformamide, N,N-dimethylacetamide, acetone, butanone, cyclohexanone, ethyl acetate, and butyl acetate.

[0155] In order to allow the hydrolysis condensation reaction to proceed smoothly and fully, the hydrolysis condensation reaction is carried out in an atmosphere of air, nitrogen or argon, and the reaction temperature is 15°C-120°C.

[0156] The hydrolysis condensation reaction can be carried out under normal pressure or reduced pressure, and the reaction time can be between 1 hour and 24 hours depending on the amount and proportion of the reaction raw materials.

[0157] After the hydrolysis and condensation reaction is completed, the second catalyst is removed from the reaction product system to obtain an organic phase; the organic phase is then dried and filtered to obtain a benzocyclobutene silicone resin.

[0158] Based on the specific type of the second catalyst, the removal method is adaptively selected. For example, when the second catalyst is tetramethylammonium hydroxide, the temperature of the reaction product system can be raised to 125°C to 150°C to achieve the purpose of removing the second catalyst. When the second catalyst is a water-washable acid or base, it can be alkaline washed or acid washed with a suitable base or acid, and then washed with water to remove the catalyst.

[0159] When drying the organic phase, a desiccant, such as sodium sulfate, magnesium sulfate or calcium chloride, may be used to achieve complete drying of the organic phase.

[0160] In summary, compared with the related art, the benzocyclobutene silicone resin prepolymerization process is more difficult to control, and oxidation to generate by-products or gelation may occur during the prepolymerization process, leading to failure. Alternatively, the resin in the related art does not require cross-linking with benzocyclobutene for prepolymerization, and its synthesis steps are cumbersome, the cost is high, and it is difficult to mass-produce.

[0161] The benzocyclobutene silicone resin and preparation method thereof provided by the disclosed embodiment can be gently synthesized by co-hydrolyzing silane monomers with different hydrolyzable groups, without the need for a prepolymerization process, and not only is the process simple, the cost is low, and it is convenient for large-scale production, and double bonds can be retained to the maximum extent, which is conducive to making photosensitive patterned resins. And the degree of polymerization of the benzocyclobutene silicone resin can be controlled, solving the problems of poor film-forming properties caused by the small molecular weight of the benzocyclobutene silicone resin in the related art. At the same time, it is also possible to easily regulate the ratio of the benzocyclobutene group in the benzocyclobutene silicone resin, so that the benzocyclobutene silicone resin obtains excellent dielectric properties (low dielectric properties), heat resistance and adhesion.

[0162] Specifically, the benzocyclobutene silicone resin provided in the embodiment of the present disclosure does not need to be prepolymerized before use, which is a difficult-to-control step (in the related art, most benzocyclobutene silicone resins need to be prepolymerized at high temperature without oxygen to increase the viscosity of the system before they can be used). The viscosity of the benzocyclobutene silicone resin provided in the embodiment of the present disclosure can be adjusted by controlling the ratio of each silane monomer and the amount of the second catalyst, without the need for high temperature and dehydration and deoxygenation. Among them, at the same reaction temperature, the more the amount of the second catalyst, the faster the hydrolysis polymerization reaction rate, the higher the degree of polymerization, and the greater the resin viscosity.

[0163] In the hydrolysis condensation reaction, a silane monomer with a single hydrolysis group is used as a capping agent, which is basically consistent with the hydrolysis main body, that is, the structure of the silane monomer, to ensure that the ratio of the benzocyclobutene group, the silicon atom and the vinyl group is 1:1:1. Of course, the proportion of the benzocyclobutene group in the benzocyclobutene silicone resin can also be adjusted by using a silane monomer without a benzocyclobutene group to participate in the hydrolysis condensation reaction, so that the proportion of the benzocyclobutene group in the benzocyclobutene silicone resin can be controlled.

[0164] In the disclosed embodiments, the preparation of silane monomers involves a Heck reaction, whose reaction conditions are relatively mild and easy to control, and is suitable for large-scale production. The preparation of benzocyclobutene silicone resin involves a hydrolysis condensation reaction, which has mild hydrolysis condensation reaction conditions, is easy to operate, and has a wide reaction temperature range (room temperature - 120°C). It can be seen that both preparation processes avoid the use of reaction methods with harsh reaction conditions (such as Grignard reaction) and unstable raw materials (such as butyl lithium, chlorosilane, etc.), which not only enables large-scale batch production of benzocyclobutene silicone resin, but also helps to reduce its cost.

[0165] On the other hand, an embodiment of the present disclosure further provides a device having a resin layer, wherein the resin layer is prepared by using any one of the above-mentioned benzocyclobutene silicone resins.

[0166] By way of example, the device includes but is not limited to the following: electronic devices (e.g., microelectronic multi-chip modules (MCM), micro-electro-mechanical systems (MEMS)), integrated circuit devices, semiconductor devices, optoelectronic devices (e.g., solar cell devices, display devices, LED devices), optical devices, etc.

[0167] The following will further describe the embodiments of the present disclosure through specific examples:

[0168] Example 1

[0169] In this Example 1, a silane monomer is prepared: benzocyclobutene-4-vinyltrimethoxysilane. The preparation principle of the benzocyclobutene-4-vinyltrimethoxysilane is shown in the following reaction formula:

[0170]

[0171] The specific preparation steps are as follows:

[0172] After evacuating nitrogen to a 250 mL eggplant-shaped bottle, 4-bromobenzocyclobutene (10 mmol), vinyltrimethoxysilane (10.5 mmol), palladium acetate (0.05 mmol), tri(o-methylphenyl)phosphine (0.20 mmol), triethylamine (12 mmol), and redispersed acetonitrile (80 mL) were added to the eggplant-shaped bottle to form a reaction system. The reaction system was replaced with nitrogen once again, and then the oil bath was heated to a reflux temperature of 80 ° C, and the reaction was carried out at this temperature. After the reaction was completed after 10 hours, the reaction was returned to room temperature. The reaction was filtered to remove the salt solid precipitated from the reaction system (the salt solid was washed three times with normal hexane for reuse). The filtrate was concentrated by rotary evaporation and then diluted with normal hexane, filtered by silica gel, and the filtrate was concentrated by rotary evaporation to remove the solvent and then the oil pump was distilled under reduced pressure to obtain a light yellow transparent liquid, which was tested to be benzocyclobutene-4-vinyltrimethoxysilane, and the reaction yield was 70%.

[0173] Example 2

[0174] In this Example 2, a silane monomer is prepared: benzocyclobutene-4-vinylmethyldimethoxysilane. The preparation principle of the benzocyclobutene-4-vinylmethyldimethoxysilane is shown in the following reaction formula:

[0175]

[0176] The specific preparation steps are as follows:

[0177] After evacuating nitrogen to a 250 mL eggplant-shaped bottle, 4-bromobenzocyclobutene (10 mmol), vinylmethyldimethoxysilane (10.5 mmol), palladium acetate (0.08 mmol), tri(o-methylphenyl)phosphine (0.30 mmol), triethylamine (12.5 mmol), and redispersed acetonitrile (80 mL) were added to the eggplant-shaped bottle to form a reaction system. The reaction system was replaced with nitrogen once again, and then the oil bath was heated to a reflux temperature of 70°C, and the reaction was carried out at this temperature. After the reaction was completed after 12 hours, the reaction was returned to room temperature. The reaction was filtered to remove the salt solid precipitated from the reaction system (the salt solid was washed three times with n-hexane for reuse). The filtrate was concentrated by rotary evaporation and then diluted with n-hexane, filtered by silica gel, and the filtrate was concentrated by rotary evaporation to remove the solvent, and then the oil pump was decompressed and distilled to obtain a light colorless transparent liquid, which was tested to be benzocyclobutene-4-vinylmethyldimethoxysilane, and the reaction yield was 75%.

[0178] Example 3

[0179] In this Example 3, a silane monomer is prepared: benzocyclobutene-4-vinyldimethylmethoxysilane. The preparation principle of the benzocyclobutene-4-vinyldimethylmethoxysilane is shown in the following reaction formula:

[0180]

[0181] The specific preparation steps are as follows:

[0182] After evacuating a 250 mL eggplant-shaped bottle with nitrogen, add 4-bromobenzocyclobutene (10 mmol), vinyldimethylmethoxysilane (10.8 mmol), palladium acetate (0.04 mmol), tri(o-methylphenyl)phosphine (0.18 mmol), triethylamine (11.5 mmol), and redispersed acetonitrile (80 mL) to form a reaction system. After the reaction system is replaced with nitrogen once again, the oil bath is heated to a reflux temperature of 85°C, and the reaction is carried out at this temperature. After 12 hours of reaction, the reaction is terminated and returned to room temperature. Filter and remove the salt solids precipitated from the reaction system. The filtrate is concentrated by rotary evaporation and then diluted with n-hexane, filtered by silica gel, and the filtrate is concentrated by rotary evaporation to remove the solvent and then distilled under reduced pressure by an oil pump to obtain a light colorless transparent liquid. After testing, it is benzocyclobutene-4-vinyldimethylmethoxysilane, and the reaction yield is 80%.

[0183] Example 4

[0184] In this Example 4, a silane monomer is prepared: benzocyclobutene-4-vinyldimethylethoxysilane. The preparation principle of the benzocyclobutene-4-vinyldimethylethoxysilane is shown in the following reaction formula:

[0185]

[0186] The specific preparation steps are as follows:

[0187] After evacuating a 250 mL eggplant-shaped bottle with nitrogen, add 4-bromobenzocyclobutene (10 mmol), vinyldimethylethoxysilane (11 mmol, obtained by reacting vinyldimethylsilyl chloride with anhydrous ethanol), palladium acetate (0.04 mmol), tri(o-methylphenyl)phosphine (0.18 mmol), triethylamine (12 mmol), and redispersed acetonitrile (80 mL) to form a reaction system. After the reaction system is replaced with nitrogen once again, the oil bath is heated to the reflux temperature of 75°C, and the reaction is carried out at this temperature. After the reaction for 12 hours, the reaction is terminated and returned to room temperature. Filter and remove the salt solids precipitated from the reaction system. The filtrate is concentrated by rotary evaporation and then diluted with n-hexane, filtered by silica gel, the filtrate is concentrated by rotary evaporation to remove the solvent, and then the oil pump is reduced pressure distilled to obtain a light colorless transparent liquid, which is benzocyclobutene-4-vinyldimethylethoxysilane after testing, and the reaction yield is 78%.

[0188] Example 5

[0189] In this Example 5, a benzocyclobutene silicone resin was prepared: linear polybenzocyclobutene-4-vinylmethylsiloxane. The preparation principle is shown in the following reaction formula:

[0190]

[0191] The specific preparation steps are as follows:

[0192] In a 25 mL single-necked eggplant-shaped bottle, add 1 mmol of benzocyclobutene-4-vinyldimethylmethoxysilane, 1.5 mmol of benzocyclobutene-4-vinylmethyldimethoxysilane, and 0.1 g of an aqueous solution of tetramethylammonium hydroxide pentahydrate (1 wt%), stir evenly at room temperature, and place in an oil bath at 50°C for 1 h of stirring reaction. After the reaction is complete, heat the temperature to 125°C to decompose the catalyst to obtain a light yellow, flowable, viscous liquid. Nuclear magnetic resonance characterization confirmed that the structure was polybenzocyclobutene-4-vinylmethylsiloxane resin.

[0193] Example 6

[0194] In this Example 6, a benzocyclobutene silicone resin was prepared: hyperbranched polybenzocyclobutene-4-vinylmethylsiloxane. The preparation principle thereof is shown in the following reaction formula:

[0195]

[0196] The specific preparation steps are as follows:

[0197] In a 25mL single-necked eggplant-shaped bottle, add 1mmol of benzocyclobutene-4-vinyldimethylmethoxysilane, 1.5mmol of benzocyclobutene-4-vinylmethyldimethoxysilane, 1.5mmol of benzocyclobutene-4-vinyltrimethoxysilane, and 0.15g of an aqueous solution (1wt%) of tetramethylammonium hydroxide pentahydrate, stir evenly at room temperature, oil bath to 80°C, stir and react for 1h, then return to room temperature, dilute with n-hexane and wash with water to remove the catalyst, dry the organic phase with anhydrous sodium sulfate, filter, and concentrate by rotary evaporation to obtain a light yellow, difficult-to-flow viscous liquid. The liquid was tested to be a benzocyclobutene silicone resin, and the dielectric constant of the benzocyclobutene silicone resin at 1MHz was as low as 2.26, which obtained excellent electrical insulation.

[0198] The above description is only for the purpose of facilitating those skilled in the art to understand the technical solution of the present disclosure and is not intended to limit the present disclosure. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present disclosure shall be included in the protection scope of the present disclosure.

Claims

1. A benzocyclobutene silicone resin, characterized in that: The benzocyclobutene silicone resin is prepared by subjecting a silane monomer containing a monohydrolyzable group and a silane monomer containing a dihydrolyzable group to a hydrolysis condensation reaction, or the benzocyclobutene silicone resin is prepared by subjecting a silane monomer containing a monohydrolyzable group, a silane monomer containing a dihydrolyzable group, and a silane monomer containing a trihydrolyzable group to a hydrolysis condensation reaction; The chemical structural formula of the silane monomer is as follows: ； Wherein, R1, R2, R3, R4, and R5 are independently selected from the following groups: H, alkyl, alkoxy, or phenyl; R6, R7, and R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted phenyl, or a hydrolyzed group, wherein the substituted C1-C6 alkyl has a first substituent, which is a C1-C4 alkyl, a C2-C4 alkynyl, an unsubstituted phenyl, or a phenyl in which 1 to 3 hydrogen atoms on the phenyl ring are substituted by a C1-C4 alkyl, and the substituted phenyl has a second substituent, which is selected from a C1-C4 alkyl, a C2-C4 alkynyl, or an unsubstituted phenyl; Furthermore, in the silane monomer containing a monohydrolyzable group, one of R6, R7, and R8 is the hydrolyzable group; in the silane monomer containing a dihydrolyzable group, two of R6, R7, and R8 are the hydrolyzable groups; in the silane monomer containing a trihydrolyzable group, R6, R7, and R8 are all the hydrolyzable groups; The hydrolyzable group is selected from substituted or unsubstituted amino, alkoxy, acyloxy, or -Cl.

2. The benzocyclobutene silicone resin according to claim 1, characterized in that: The hydrolyzable group is selected from dimethylamino, diethylamino, C1-C4 alkoxy, or C1-C4 acyloxy.

3. The benzocyclobutene silicone resin according to claim 1, characterized in that: The chemical structural formula of the silane monomer is as follows: 。 4. The benzocyclobutene silicone resin according to claim 3, characterized in that: The chemical structural formulas of the silane monomer containing a monohydrolyzable group, the silane monomer containing a dihydrolyzable group, and the silane monomer containing a trihydrolyzable group are respectively as follows: ;or ； or 。 5. The benzocyclobutene silicone resin according to claim 3, characterized in that: The chemical structural formula of the benzocyclobutene silicone resin is as follows: ； Wherein, n is an integer greater than 0; R' is selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl or unsubstituted or substituted phenyl.

6. The benzocyclobutene silicone resin according to claim 3, characterized in that: The chemical structural formula of the benzocyclobutene silicone resin is as follows: ； Wherein, x, y and z are all integers greater than 0; R`` is selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl or unsubstituted or substituted phenyl.

7. The method for preparing the benzocyclobutene silicone resin according to any one of claims 1 to 6, characterized in that: The preparation method of the benzocyclobutene silicone resin comprises: Provide a variety of silane monomers; Under the catalytic action of a second catalyst, the plurality of silane monomers are subjected to a hydrolysis-condensation reaction in an aqueous solution to obtain the benzocyclobutene organosilicon resin; Wherein, the preparation method of the silane monomer comprises: Under an inert atmosphere, a vinyl-containing siloxane and 4-bromobenzocyclobutene are subjected to a Heck reaction in a dry solvent having a first catalyst and an acid binding agent to obtain the silane monomer; Wherein, the chemical structural formula of the vinyl-containing siloxane is as follows: ； R6, R7, and R8 are independently selected from the following groups: H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted phenyl, or a hydrolyzable group, and at least one of R6, R7, and R8 is the hydrolyzable group; The hydrolyzable group is selected from dimethylamino, diethylamino, C1-C4 alkoxy or C1-C4 acyloxy.

8. The method for preparing the benzocyclobutene silicone resin according to claim 7, characterized in that: The first catalyst is selected from palladium acetate, palladium chloride, tetrakis(triphenylphosphine)palladium, palladium-carbon catalyst or diphenylphosphinoferrocenepalladium dichloride.

9. The method for preparing a benzocyclobutene silicone resin according to claim 7, characterized in that: The acid binding agent is selected from at least one of triethylamine, diethylamine, potassium carbonate, sodium carbonate, pyridine and imidazole.

10. The method for preparing a benzocyclobutene silicone resin according to claim 7, characterized in that: The drying solvent is selected from at least one of benzene, acetonitrile, tetrahydrofuran, dioxane, N,N-dimethylformamide and N,N-dimethylacetamide.

11. The method for preparing a benzocyclobutene silicone resin according to claim 7, characterized in that: The reaction temperature of the Heck reaction is 50° C.-120° C., and the reaction time is 4 hours-48 hours.

12. The method for preparing a benzocyclobutene silicone resin according to claim 7, characterized in that: The second catalyst is an acid catalyst or a base catalyst; The acid catalyst is selected from at least one of formic acid, acetic acid, hydrochloric acid, phosphoric acid and sulfuric acid; The alkaline catalyst is selected from at least one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium phosphate, ammonia water, diethylamine, triethylamine, pyridine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, imidazole, N-methylimidazole, N-ethylimidazole, and benzyltrimethylammonium hydroxide.

13. The method for preparing a benzocyclobutene silicone resin according to claim 7, characterized in that: The reaction temperature of the hydrolysis condensation reaction is 15°C-120°C.

14. The method for preparing a benzocyclobutene silicone resin according to any one of claims 7 to 13, characterized in that: The preparation method of the benzocyclobutene silicone resin also includes: After the hydrolysis and condensation reaction is completed, removing the second catalyst from the reaction product system to obtain an organic phase; The organic phase is dried and filtered to obtain the benzocyclobutene silicone resin.

15. A device, characterized in that The device comprises a resin layer, and the resin layer is prepared by using the benzocyclobutene silicone resin according to any one of claims 1 to 6.

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