Organosilicon compound and polymer using the same

Abstract

To provide an organosilicon compound having a double-decker silsesquioxane structure in which a cage vertex bears a non-aromatic ring substituent, a silsesquioxane derivative with a functional group derived from the same, and a polymer composed of such derivatives.SOLUTION: An organosilicon compound expressed by formula (1), wherein R independently represents H, halogen, alkyl, cycloalkyl, or the like; at least one Y is a group selected from -SiR1R2Z, and the other Y are H.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to organosilicon compounds and polymers using the same, more specifically to organosilicon compounds having a silsesquioxane skeleton and polymers using the same. More specifically, the present invention relates to silsesquioxane structures having aliphatic or other substituents, preferably alicyclic substituents, at the vertices of the cage structure, and to silsesquioxane derivatives derived therefrom having functional groups such as amino groups, hydrosilyl groups, glycidyl groups, hydroxyl groups, acetoxy groups, carboxyl groups, methacryloxy groups, chloropropyl groups, vinyl groups, and siloxane groups, as well as polymers comprising these derivatives. In this specification, the term "cage structure vertices" refers to the eight Si atoms to which eight R groups are bonded in formula (1) described below. [Background technology]

[0002] Silsesquioxane compounds have been identified as having ladder structures, fully condensed structures, incompletely condensed structures, and amorphous structures, and much research has been conducted on these. Among these, silsesquioxanes with fully condensed and incompletely condensed structures, which are the easiest to control, have attracted attention, and Hybrid Plastics has commercially marketed silsesquioxane derivatives with various functional groups introduced into them (Non-Patent Document 1).

[0003] However, conventional incompletely condensed and fully condensed silsesquioxanes and their derivatives have poor solubility, and when used in coating materials, there are limitations on film-forming properties and the amount that can be added, making it difficult to effectively use them in a wide range of applications. A double-decker structure silsesquioxane (Patent Document 1) that overcomes these drawbacks has been developed, and its application to various materials has been investigated.

[0004] On the other hand, many of the double-decker silsesquioxanes and their derivatives reported to date have phenyl substituents at the apex of the cage structure. Aromatic structures such as phenyl substituents exhibit high heat resistance, but because they have conjugated ring structures, they are prone to intermolecular interactions and conjugation with adjacent structures, which can lead to significant concerns about the coloration of polyimide materials, as well as the refractive index and dielectric properties, leaving room for improvement. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2004 / 024741 (Patent No. 4470738) [Non-patent literature]

[0006] [Non-Patent Document 1] Ronald H. Bunny, Maki Ito, Akihito Sakakibara, and Toshio Suzuki, "Silsesquioxanes," Chemical Review, American Chemical Society, 1995, Vol. 95, No. 5, pp. 1409-1430 (Chem. Rev. 95, 1409-1430 (1995)) Summary of the Invention [Problem to be solved by the invention]

[0007] In view of the problems of the prior art described above, the present invention aims to provide an organosilicon compound having a double-decker silsesquioxane structure with non-aromatic ring substituents at the vertices of the cage structure, as well as silsesquioxane derivatives derived therefrom having functional groups such as amino groups, hydrosilyl groups, glycidyl groups, hydroxyl groups, acetoxy groups, carboxyl groups, methacryloxy groups, chloropropyl groups, vinyl groups, and siloxane groups, and polymers comprising these derivatives. [Means for solving the problem]

[0008] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have succeeded in synthesizing an organosilicon compound having a double-decker silsesquioxane structure with a non-aromatic ring substituent at the apex of the cage structure, which can fully impart the properties expected of silsesquioxanes, by converting the aromatic ring substituent at the apex of the cage structure to a non-aromatic ring substituent such as an aliphatic substituent. Furthermore, they have succeeded in converting the terminal functional groups of the structure to functional groups such as amino groups, hydrosilyl groups, glycidyl groups, hydroxyl groups, acetoxy groups, carboxyl groups, methacryloxy groups, chloropropyl groups, vinyl groups, and siloxane groups, and have found that this can produce precursors of polymers useful in the development of useful optical components, dielectric materials, electronic components, and the like, thereby completing the present invention.

[0009] The present invention includes the following configurations. [1] An organosilicon compound represented by formula (1): TIFF2025115620000002.tif5193In formula (1), R is independently hydrogen, halogen, alkyl having 1 to 45 carbon atoms, or cycloalkyl having 4 to 18 carbon atoms; in the alkyl having 1 to 45 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH2- may be replaced by -O- or cycloalkylene having 4 to 18 carbon atoms, and in the cycloalkyl having 4 to 18 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms; at least one Y is a group selected from the groups represented by formula (2), and the remaining Ys are hydrogen; and when at least two Ys are groups represented by formula (2), they may be the same group or may be composed of at least two different groups; TIFF2025115620000003.tif2056 in formula (2), R 1 and R 2are independently hydrogen, alkyl having 1 to 45 carbon atoms, aryl having 6 to 45 carbon atoms, or arylalkyl having 7 to 45 carbon atoms; in the alkyl having 1 to 45 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH2- may be replaced by -O-, -CH=CH-, cycloalkylene having 4 to 18 carbon atoms, or cycloalkenylene having 4 to 18 carbon atoms; in the aromatic ring of the aryl having 6 to 45 carbon atoms and arylalkylene having 7 to 45 carbon atoms, at least one hydrogen may be replaced by fluorine; in the alkylene of the arylalkyl having 7 to 45 carbon atoms, the number of carbon atoms is 1 to 39, and at least one -CH2- may be replaced by -O-, -CH=CH-, or cycloalkylene; and Z is R 1 It is a group, functional group or group having a functional group having the same definition as above.

[0010] [2] The organosilicon compound is represented by the formula (1) and the formula (2), wherein R 1 and R 2 are independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, or phenyl.

[0011] [3] The organosilicon compound according to [1] or [2], wherein in the formula (1), R is independently alkyl having 1 to 12 carbon atoms or cycloalkyl having 4 to 10 carbon atoms; in the alkyl having 1 to 12 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH2- may be replaced by -O- or cycloalkylene having 4 to 10 carbon atoms; and in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms.

[0012] [4] The organosilicon compound according to any one of [1] to [3], wherein in the formula (1), R is independently a cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or an alkyl having 1 to 3 carbon atoms; and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or an alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

[0013] [5] The organosilicon compound according to any one of [1] to [4], wherein in the formula (1), all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms; and when the cycloalkyl having at least one hydrogen replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

[0014] [6] The organosilicon compound according to any one of [1] to [5], wherein in the formula (1), all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms in which at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms, and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

[0015] [7] The organosilicon compound according to any one of [1] to [6], wherein in the organosilicon compound, all R are cyclohexyl in the formula (1).

[0016] [8] The organosilicon compound is represented by the formula (1) and the formula (2), wherein R 1 and R 2are independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, or phenyl; and Z is a functional group or a group having a functional group, the functional group being a group directly bonded to the Si atom selected from hydrogen, halogen, —OH, alkoxy, alkenyl, and fluorinated alkyl, the group having a functional group being a group composed of a divalent group and a functional group bonded to the Si atom via the divalent group, the divalent group being a divalent group selected from alkylene, alkylcycloalkylene, alkylenephenylene, alkylphenylene, and alkylphenylalkylene, and the alkylene and alkyl in these divalent groups are at least The organosilicon compound according to any one of [1] to [7], wherein at least one -CH2- may be replaced by -O-, and the functional group bonded to the Si atom via a divalent group is a group selected from hydrogen, halogen, -OH, fluorinated alkyl, alkoxy, carboxyl, 2-oxapropanedioyl, carboxylic anhydride residue, maleimide residue, acetoxy, vinyloxycarbonyl, allyloxycarbonyl, acryloyloxy, methacryloyloxy, polyalkyleneoxy, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, alkenyl, cycloalkenyl, -NH2, -CN, -NCO, -SH, and -PH2.

[0017] [9] The organosilicon compound according to [8], wherein in the formula (1) according to [1], R is independently alkyl having 1 to 12 carbon atoms or cycloalkyl having 4 to 10 carbon atoms; in the alkyl having 1 to 12 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH2- may be replaced by -O- or cycloalkylene having 4 to 10 carbon atoms, and in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms.

[0018]

[10] The organosilicon compound according to [8] or [9], wherein in the formula (1) according to [1], R is independently a cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or an alkyl having 1 to 3 carbon atoms; and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or an alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

[0019]

[11] The organosilicon compound according to any one of [8] to

[10] , wherein in the formula (1) according to [1], all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms, and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

[0020]

[12] The organosilicon compound according to any one of [8] to

[11] , wherein in the formula (1) according to [1], all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms in which at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms, and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

[0021]

[13] The organosilicon compound according to any one of [8] to

[12] , wherein in the formula (1) according to [1], all R are cyclohexyl.

[0022]

[14] The organosilicon compound according to any one of [1] to

[13] , wherein Z in the formula (1) and the formula (2) is an alkyl halide or a group having an alkyl halide.

[0023]

[15] The organosilicon compound according to any one of [1] to

[13] , wherein in the formula (1) and the formula (2), Z is alkenyl, or a group having any of alkenyl, -OH, carboxyl, 2-oxapropanedioyl, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, and -NH2.

[0024]

[16] The organosilicon compound precursor according to any one of [1] and [3] to [7], wherein in formula (1), all Y's are hydrogen.

[0025]

[17] A polymer obtained by using the organosilicon compound according to

[15] . [Effects of the Invention]

[0026] The organosilicon compound of the present invention is a silsesquioxane structure having a non-aromatic ring substituent at the apex of the cage structure, and its derivatives. In the organosilicon compound of the present invention, the terminal functional group of the silsesquioxane structure having a non-aromatic ring substituent at the apex of the cage structure is converted to a functional group such as an amino group, a hydrosilyl group, a glycidyl group, a hydroxyl group, an acetoxy group, a carboxyl group, a methacryloxy group, a chloropropyl group, a vinyl group, or a siloxane group, thereby obtaining a precursor of the polymer of the present invention, which can be used in the development of useful optical components, dielectric materials, electronic components, etc. [Brief explanation of the drawings]

[0027] [Figure 1] FIG. 1 is an IR spectrum of the compound (1) synthesized in Example 1. [Figure 2] FIG. 2 is an IR spectrum of the compound (1′) used in the synthesis of the compound (1) in Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0028] Hereinafter, the embodiments of the present invention will be described in detail, but the following description is an example (typical example) of the embodiment of the present invention, and the present invention is not limited to these examples. Furthermore, the embodiments of the present invention can be combined as appropriate.

[0029] 1. Organosilicon Compound of the Present Invention In the organosilicon compounds of the present invention, the alkyl having 1 to 45 carbon atoms represented by formulas (1) and (2) may be a straight-chain or branched group. In the alkyl having 1 to 45 carbon atoms, when at least one hydrogen is replaced by fluorine or when at least one -CH2- is replaced by -O-, -CH=CH-, cycloalkylene, cycloalkenylene, or the like, the alkyl may be a straight-chain or branched group. In the present invention, when it is stated that at least one -CH2- is replaced by -O-, multiple consecutive -CH2- are not replaced by -O-, taking into consideration the stability of the compound.

[0030] Preferred examples of R in formula (1) include 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, decahydronaphthyl, tetradecahydroanthracenyl, octadecahydrotetracenyl, hexadecahydropyrenyl, and trifluoromethylcyclohexyl.

[0031] Among these, the more preferred R in formula (1) is a group in which all R are the same, ie, cyclohexyl.

[0032] At least one Y in formula (1) is a group selected from the groups represented by formula (2), and the remaining Ys are hydrogen. When at least two Ys are groups represented by formula (2), the multiple Ys may be the same group or may be composed of at least two different groups. TIFF2025115620000004.tif2053

[0033] R in Equation (2) 1 and R 2 Preferred specific examples of include hydrogen, alkoxy having 1 to 44 carbon atoms, alkoxyalkyl having 2 to 44 carbon atoms, alkenyl having 2 to 45 carbon atoms, alkenyloxyalkyl having 3 to 45 carbon atoms, alkyloxyalkenyl having 3 to 45 carbon atoms, alkyl having 1 to 45 carbon atoms in which one -CH2- is replaced by cycloalkylene, alkyl having 1 to 45 carbon atoms in which one -CH2- is replaced by cycloalkenylene, alkyl having 1 to 45 carbon atoms, aryl having 6 to 45 carbon atoms, arylalkyl having 7 to 45 carbon atoms, and groups in which at least one hydrogen in these groups is replaced by fluorine.

[0034] Among these, R in formula (2) 1 and R 2 is independently more preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl or phenyl.

[0035] In formula (2), Z is R 1 R is a group, functional group, or group having a functional group having the same definition as 1 Among groups having the same definition as above, preferred are groups selected from alkyl having 1 to 45 carbon atoms, alkoxy having 1 to 44 carbon atoms, alkenyl having 2 to 45 carbon atoms, alkyloxyalkenyl having 3 to 45 carbon atoms, phenyl and naphthyl in which at least one hydrogen atom in the aromatic ring may be replaced by fluorine. Preferred specific examples of these groups are R 1 This is the same as that shown for

[0036] Z is a functional group or a group having a functional group, and a preferred specific example is a group in which the functional group is directly bonded to the Si atom and is selected from hydrogen, halogen, -OH, alkoxy, alkenyl, and fluorinated alkyl, and the group having a functional group is a group composed of a divalent group and a functional group bonded to the Si atom via the divalent group, and the divalent group is a divalent group selected from alkylene, alkylcycloalkylene, alkylenephenylene, alkylphenylene, and alkylphenylalkylene, and in the alkylene and alkyl in these divalent groups, at least one -CH2- is replaced with - O-, and the functional group bonded to the Si atom via a divalent group is selected from hydrogen, halogen, -OH, fluorinated alkyl, alkoxy, carboxyl, 2-oxapropanedioyl, carboxylic anhydride residue, maleimide residue, acetoxy, vinyloxycarbonyl, allyloxycarbonyl, acryloyloxy, methacryloyloxy, polyalkyleneoxy, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, alkenyl, cycloalkenyl, -NH2, -CN, -NCO, -SH, and -PH2.

[0037] Specific examples of halogen include fluorine, chlorine, and bromine. Specific examples of alkenyl include vinyl and allyl. Specific examples of cycloalkenyl include cyclopentadienyl, cyclohexenyl, and norbornenyl.

[0038] In formula (2), more preferred specific examples of Z are shown in formulas (3) to (27). TIFF2025115620000005.tif212164

[0039] In formulas (8) to (27) and (29), k is 0 or 1, m is an integer of 1 to 4, and n is an integer of 0 to 15. X is a halogen, p is an integer of 1 to 5, q is 2 or 3, and r is an integer of 2 to 200. t is an integer of 1 to 3. E is hydrogen or an alkyl having 1 to 4 carbon atoms, and R is an alkyl having 1 to 6 carbon atoms. In the above examples, -X, -CH2-X, -OH, and -COOH may be bonded to the benzene ring at any position. Specific examples of more preferred halogens include fluorine and chlorine. A more preferred range for r is 2 to 100, and an even more preferred range is 2 to 20.

[0040] The organosilicon compound of the present invention is characterized in that the vertices of the cage structure have non-aromatic ring substituents such as cycloalkyl. To synthesize the organosilicon compound of the present invention, it is preferable to use a precursor of the organosilicon compound of the present invention, which is prepared by starting from a cage silsesquioxane silanol having an aromatic ring substituent at the vertex of the cage structure and converting the aromatic ring substituent at the vertex of the cage structure to a non-aromatic ring substituent such as a cycloalkyl substituent. This precursor is the organosilicon compound precursor of the present invention, and is preferably compound (1) represented by formula (1-1), in which all R in formula (1) are cyclohexyl (Cy) and all Y are hydrogen. Compound (1) is preferably synthesized using a nuclear hydrogenation method in the presence of a noble metal catalyst. TIFF2025115620000006.tif5194

[0041] The organosilicon compounds of the present invention can be synthesized using compound (1) in a one-step synthesis via reaction with a compound having a chlorosilyl group, or in a two-step synthesis via reaction with dimethylchlorosilane followed by hydrosilylation with a compound having an unsaturated hydrocarbon group. By providing a functional group or a group having a functional group to these chlorosilyl group-containing compounds or unsaturated hydrocarbon group-containing compounds, organosilicon compounds having a functional group or a group having a functional group can be synthesized. The chlorosilyl group-containing compounds may be commercially available, or may be synthesized by known techniques such as the reaction of a halogenated silane with a Grignard reagent.

[0042] When the functional group of the organosilicon compound of the present invention is an addition-polymerizable or condensation-polymerizable group, the polymer of the present invention can be obtained by a general polymerization method such as radical polymerization, anionic polymerization, cationic polymerization, metal-initiated polymerization, or condensation polymerization. In this case, a single monomer may be used, or copolymerized with other monomers. Copolymers obtained by arranging multiple monomers may be random copolymers, block copolymers, or alternating copolymers. Graft copolymers can also be obtained by graft copolymerization with other polymers.

[0043] In the polymerization reaction for synthesizing the polymer of the present invention, it is preferable to use a solvent. There are no particular limitations on the solvent as long as it can dissolve the raw material monomers used in the polymerization reaction or the product polymer. Examples of the solvent used in the polymerization reaction include organic solvents made of the compounds exemplified below. Examples of solvents used in polymerization reactions such as condensation polymerization reactions, radical polymerization reactions, and anionic polymerization reactions include toluene, xylene, mesitylene, cyclopentanone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, isopropanol, propylene glycol monomethyl ether, ethyl acetate, butyl acetate, propylene glycol monomethyl acetate, N-methyl-2-pyrrolidone, formamide, N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylimidazolidinone, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, γ-butyrolactone, tetrahydrofuran, dioxane, ethylene glycol monoalkyl ethers, diethylene glycol monoalkyl ethers, diethylene glycol dialkyl ethers, diethylene glycol monoalkyl ether acetates such as diethylene glycol mono-n-butyl ether acetate, dichloromethane, chloroform, and 1,2-dichloroethane. The optimum solvent varies depending on the polymerization reaction, but preferred examples include toluene, cyclohexanone, N-methyl-2-pyrrolidone, N,N-dimethylacetamide, tetrahydrofuran, and diethylene glycol mono-n-butyl ether acetate, which are highly versatile. These solvents may be used alone or in combination.

[0044] The polymer of the present invention may be used as a liquid polymer or a solid polymer after removing the reaction solvent, but from the viewpoint of shortening the time required for processing the polymer, such as film formation, it is preferable to leave the reaction solvent intact and use the polymer as a polymer solution or gel. [Example]

[0045] The present invention will be explained in more detail below by way of examples in which the organosilicon compound precursor of the present invention, the organosilicon compound of the present invention, and the polymer of the present invention are respectively synthesized, but the present invention is not limited to these examples in any way. For the abbreviations used in the examples, the corresponding compound names, trade names, etc. are listed below. <Functional group> Cy: Cyclohexyl Ph: Phenyl Me: Methyl Ac: Acetyl <Solvent> THF: tetrahydrofuran XQ1175: Compound (1') represented by formula (1-1') (XQ1175; trade name; manufactured by JNC Corporation) TIFF2025115620000007.tif5196

[0046] The abbreviations for the measurement items in the examples are shown below. Mn: Number average molecular weight Mw: Weight average molecular weight

[0047] Next, the measuring equipment and analytical conditions used in the examples are shown. <ft-ir> Equipment: JASCO FT / IR-6700V Measurement conditions: KBr method, room temperature < 1 H-NMR Equipment: JEOL Ltd. JNM-ECZ500R (500MHz) Solvent: deuterated chloroform Measurement temperature: room temperature Internal standard: tetramethylsilane < 13 C-NMR Equipment: JEOL Ltd. JNM-ECZ500R (500MHz) Solvent: deuterated chloroform Measurement temperature: room temperature < 29 Si-NMR Equipment: JEOL Ltd. JNM-ECZ500R (500MHz) Solvent: deuterated chloroform Measurement temperature: room temperature Internal standard: tetramethylsilane <gpc> Equipment: High-performance liquid chromatograph system CO-2065Plus manufactured by JASCO Corporation Detector: RI-4030 Eluent:THF Flow rate: 1.0mL / min Column: Shodex KF804L manufactured by Resonac Inc. (formerly Showa Denko K.K.) (two connected in series) Column temperature: 40℃ Sample concentration: 1 wt% Injection volume: 20μl Standard sample for calibration curve: TSK standard polystyrene manufactured by Tosoh Corporation

[0048] Example 1 <Synthesis of the organosilicon compound precursor of the present invention: compound (1)> In a 2 L high-pressure reactor equipped with a stirrer, compound (1') (XQ1175) (267.4 g; 250.0 mmol), Ru / C (5 wt% Ru, hydrous) (2.0 g; 1.0 mmol Ru) (manufactured by N.E. Chemcat Corporation), and cyclopentyl methyl ether (1300.0 g) were reacted at 80 °C for 3 hours under a 0.2 MPa hydrogen atmosphere. The catalyst was then filtered to separate the solid and liquid, and anhydrous magnesium sulfate was added to the filtrate for dehydration and drying. After solid-liquid separation by filtration, the filtrate was concentrated using a rotary evaporator. The resulting solid concentrate was dried under reduced pressure at 70 °C for 6 hours to obtain compound (1) as a white solid (yield: 273.8 g, 98%). GPC analysis of the resulting compound (1) confirmed a single peak, and no impurities were detected. The IR spectrum of this compound (1) is shown in Figure 1. Figure 1 shows the IR spectrum of compound (1) represented by the above formula (1-1), which is an organosilicon compound precursor of the present invention synthesized in Example 1. Compound (1) corresponds to the compound in which R is cyclohexyl and Y is hydrogen in the above formula (1). From the IR spectrum of Figure 1, the aromatic ring-derived peak at 1597 cm observed in the IR spectrum of the raw material compound (1') (Figure 2) is observed after the nuclear hydrogenation reaction. -1 and 3016-3084 cm -1 The disappearance of was confirmed. Figure 2 is an IR spectrum diagram of compound (1') represented by the above formula (1-1'), which is a compound used in the synthesis of compound (1) in Example 1. Compound (1') is manufactured by JNC Corporation under the trade name: XQ1175, and corresponds to the compound in which cyclohexyl for R in the above formula (1) is replaced with phenyl and Y is hydrogen. As a result of NMR measurement, it was confirmed that compound (1) has the structure of formula (1-1), and its chemical shifts are shown below. 1 H-NMR (500MHz, CDCl3) δ0.65-0.82 (m, 8H), 1.15-1.37 (m, 40H), 1.59-1.92 (m, 40H). 29 Si-NMR (79MHz, CDCl3) δ-60.41,-71.76.

[0049] Example 2 <Synthesis of Compound (2), an organosilicon compound of the present invention having a hydrosilyl group> Compound (1) (72.10 g; 64.5 mmol) obtained in Example 1 and THF (600 g) were added to a 1 L four-neck flask equipped with a dropping funnel, thermometer, and reflux condenser. The mixture was stirred under a nitrogen atmosphere. While maintaining the solution temperature at 23-38°C, chlorodimethylsilane (80 g; 845.6 mmol) was added dropwise using the dropping funnel over approximately 11 minutes. After the dropwise addition, the mixture was heated in an oil bath with stirring and refluxed for 3 hours, after which the reaction mixture was cooled to room temperature. Unreacted chlorodimethylsilane was removed by distillation, and 300 g of the reaction solvent was distilled off. The reaction mixture was cooled to room temperature, and pure water (150 g) was added dropwise using the dropping funnel. After stirring for 10 minutes, the organic and aqueous layers were separated using a separatory funnel. The organic layer was washed twice with pure water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, resulting in the precipitation of solids. The precipitated solid was washed with normal heptane (750 ml), filtered, and dried under reduced pressure to obtain compound (2) as a white powdery solid (amount: 58.36 g, yield: 67%).

[0050] The structure of compound (2) shown in formula (1-2) was confirmed by FT-IR analysis. -1 Absorption due to Si-H stretching was confirmed. 29 As a result of Si-NMR analysis, a signal of a dimethylsilyl group was confirmed at -3.81 ppm. 1 H-NMR analysis confirmed that the integral ratios of Cy, SiH, and Me groups were 88:4:24, respectively. GPC analysis revealed that Mn was 980 and Mw was 1,050.

[0051] TIFF2025115620000008.tif51105

[0052] Example 3 <Synthesis of the glycidyl group-containing organosilicon compound of the present invention: compound (3)> Compound (2) (2.07 g; 1.53 mmol) obtained in Example 2, allyl glycidyl ether (1.4 g; 12.3 mmol), and THF (10.0 g) were added to a 50 mL four-neck flask equipped with a dropping funnel, a thermometer, and a reflux condenser. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath to maintain the solution temperature at 70°C. Karstedt catalyst (2.0 μl) was added using a microsyringe, and stirring was continued for 1 hour. A sample of the reaction solution was taken and subjected to FT-IR analysis, revealing a peak at 2140 cm suggesting the presence of Si-H groups. -1 After the disappearance of the peak was confirmed, the reaction system was cooled to room temperature to terminate the reaction. The reaction solution was concentrated using an evaporator to obtain compound (3) as a viscous liquid (yield: 2.57 g, 93%).

[0053] When the structure of compound (3) shown in formula (1-2) was confirmed, 29 Si-NMR analysis confirmed a signal at 11.40 ppm corresponding to the glycidoxypropyldimethylsilyl group. GPC analysis revealed that Mn was 1,150 and Mw was 1,240.

[0054] TIFF2025115620000009.tif51162

[0055] Example 4 <Synthesis of the hydroxyl group-containing organosilicon compound of the present invention: compound (4)> Compound (2) (5.4 g; 3.99 mmol) obtained in Example 2, 2-allyloxyethanol (6.6 g; 64.6 mmol), and THF (30.0 g) were added to a 100 mL four-neck flask equipped with a dropping funnel, a thermometer, and a reflux condenser. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath to maintain the solution temperature at 60°C. Karstedt catalyst (3.3 μl) was added using a microsyringe, and stirring was continued for 2 hours. A sample of the reaction solution was taken and subjected to FT-IR analysis, revealing a peak at 2140 cm indicating the presence of Si-H groups. -1 The disappearance of the peak at 3450 cm -1 Absorption due to the OH stretching vibration of the hydroxyl group was confirmed, and the reaction system was cooled to room temperature to terminate the reaction. The reaction solution was concentrated using an evaporator, and the residue was diluted with ethyl acetate (28.0 g) to a concentration of 20% by weight. Powdered activated carbon (0.4 g) was added, and the mixture was stirred at room temperature for 1.5 hours. The activated carbon was then removed by filtration. The filtrate was concentrated using an evaporator to obtain compound (4) as a viscous liquid (yield: 6.8 g, 97%).

[0056] When the structure of compound (4) shown in formula (1-4) was confirmed, 29 Si-NMR analysis confirmed a signal at 11.40 ppm corresponding to the (3-(2-hydroxyethyloxy)propyl)dimethylsilyl group. GPC analysis revealed that Mn was 1,300 and Mw was 1,370.

[0057] TIFF2025115620000010.tif46147

[0058] Example 5 <Synthesis of Acetoxy Group-Containing Organosilicon Compound of the Present Invention: Compound (5)> Compound (2) (10.7 g; 7.92 mmol) obtained in Example 2, 2-allyloxyethyl ester of acetic acid (6.9 g; 47.9 mmol) prepared from 2-allyloxyethanol and acetyl chloride, and THF (60.0 g) were added to a 200 mL four-neck flask equipped with a dropping funnel, a thermometer, and a reflux condenser. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath to maintain the solution temperature at 60°C. Karstedt catalyst (10 μl) was added using a microsyringe. The reaction solution was then heated to 80°C and stirred for an additional 4 hours. A sample of the reaction solution was taken and subjected to FT-IR analysis, revealing a peak at 2140 cm indicating the presence of Si-H groups. -1 The disappearance of the peak at 1739 cm -1 The reaction mixture was concentrated using an evaporator to give compound (5) as a viscous liquid (yield: 15.1 g, 99%).

[0059] When the structure of compound (5) shown in formula (1-5) was confirmed, 29 As a result of Si-NMR analysis, a signal at 11.40 ppm corresponding to a (3-(2-acetoxyethoxy)propyl)dimethylsilyl group was confirmed. 13 C-NMR analysis confirmed a signal at 170.83 ppm derived from a C=O group. GPC analysis revealed that Mn was 1,510 and Mw was 1,580.

[0060] TIFF2025115620000011.tif45147

[0061] Example 6 <Synthesis of the carboxyl group-containing organosilicon compound of the present invention: compound (6)> Compound (2) (5.4 g; 3.99 mmol) obtained in Example 2, 4-pentenoic acid trimethylsilyl ester (1.7 g; 17.4 mmol), and THF (30.0 g) were added to a 100 mL four-neck flask equipped with a dropping funnel, a thermometer, and a reflux condenser. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath to maintain the solution temperature at 80°C. Karstedt catalyst (4.0 μl) was added using a microsyringe. The reaction solution was then heated to 80°C and stirred for an additional 4 hours. A sample of the reaction solution was taken and subjected to FT-IR analysis, revealing a peak at 2140 cm indicating the presence of Si-H groups. -1 The disappearance of the peak at 1739 cm -1 Absorption due to C=O stretching was confirmed, and the reaction system was cooled to room temperature to terminate the reaction. The reaction solution was concentrated using an evaporator, and methyl alcohol (6.1 g) was added to the residue and stirred at room temperature for 4 hours. Powdered activated carbon (0.4 g) was then added and stirred at room temperature for an additional 1 hour, after which the activated carbon was removed by filtration. The filtrate was concentrated using an evaporator to obtain compound (6) as a white solid (yield: 6.4 g, 91%).

[0062] When the structure of compound (6) shown in formula (1-6) was confirmed, 13 C-NMR analysis confirmed a signal at 180.44 ppm derived from a carboxyl group. GPC analysis revealed that Mn was 1,540 and Mw was 1,650.

[0063] TIFF2025115620000012.tif51159

[0064] Example 7 <Synthesis of Compound (7), an organosilicon compound of the present invention having a methacryloxy group> Compound (1) (1.16 g; 1.04 mmol) obtained in Example 1, THF (30 g), and triethylamine (8.1 g; 80.0 mmol) were added to a 100 mL four-neck flask equipped with a dropping funnel, thermometer, and reflux condenser. The mixture was stirred under a nitrogen atmosphere. While maintaining the solution temperature at 5-10°C, methacryloxypropyldimethylchlorosilane (18 g; 81.5 mmol) was added dropwise using the dropping funnel over approximately 11 minutes, and the mixture was allowed to react at room temperature for 5 hours. Purified water (10 g) was added dropwise using the dropping funnel, and the mixture was stirred for 10 minutes. The organic and aqueous layers were separated using a separatory funnel. The organic layer was washed twice with purified water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a viscous liquid. The resulting viscous liquid was purified by silica gel chromatography using a mixed solvent of normal hexane and ethyl acetate in a volume ratio of 5:1 to obtain compound (7) as a white solid (amount: 1.54 g, yield: 80%).

[0065] The structure of compound (7) shown in formula (1-7) was confirmed by FT-IR analysis. -1 Absorption due to C=O stretching was confirmed. 29 Si-NMR analysis confirmed a peak at 11.02 ppm suggesting the 3-methacryloxypropyldimethylsilyl group. GPC analysis revealed that Mn was 1,230 and Mw was 1,290.

[0066] TIFF2025115620000013.tif51160

[0067] Example 8 <Synthesis of Compound (8), an organosilicon compound of the present invention having a 3-chloropropyl group> Compound (1) (5.6 g; 5.01 mmol) obtained in Example 1, THF (150 g), and triethylamine (5.0 g; 49.4 mmol) were added to a 300 mL four-neck flask equipped with a dropping funnel, thermometer, and reflux condenser. The mixture was stirred under a nitrogen atmosphere. While maintaining the solution temperature at 28-41°C, 3-chloropropyldimethylchlorosilane (10.3 g, 60.2 mmol) was added dropwise using the dropping funnel over approximately 5 minutes, and the mixture was allowed to react at room temperature for 4 hours. Purified water (30 g) was added dropwise using the dropping funnel. After stirring for 10 minutes, the organic and aqueous layers were separated using a separatory funnel. The organic layer was washed twice with 0.1 N aqueous hydrochloric acid and then with purified water. It was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a viscous liquid. The resulting viscous liquid was recrystallized from methyl alcohol (120 g) to obtain compound (8) as a white solid (yield: 6.6 g, 80%).

[0068] The structure of compound (8) shown in formula (1-8) was confirmed by FT-IR analysis, and the peak at 787 cm -1 Absorption due to the stretching of the C-Cl group was confirmed. 1 H-NMR analysis confirmed a triplet split signal at 3.0 ppm originating from the -CH2Cl group. 13 C-NMR analysis confirmed a signal at 47.36 ppm derived from the -CH2Cl group. 29 Si-NMR analysis confirmed the signal of 3-chloropropyldimethylsilyl group at 10.84 ppm. GPC analysis revealed Mn of 1,180 and Mw of 1,210.

[0069] TIFF2025115620000014.tif51150

[0070] Example 9 <Synthesis of Compound (9), an organosilicon compound of the present invention having an anilinyl group> Compound (1) (5.6 g; 5.01 mmol) obtained in Example 1, THF (150 g), and triethylamine (5.0 g; 49.4 mmol) were added to a 300 mL four-neck flask equipped with a dropping funnel, thermometer, and reflux condenser. The mixture was stirred under a nitrogen atmosphere. Anilinodimethylchlorosilane (11.2 g, 60.3 mmol) was added dropwise using the dropping funnel over approximately 5 minutes while maintaining the solution temperature at 28-41°C. The mixture was allowed to react at room temperature for 4 hours. Purified water (30 g) was added dropwise using the dropping funnel. After stirring for 10 minutes, the organic and aqueous layers were separated using a separatory funnel. The organic layer was washed twice with 0.1 N aqueous hydrochloric acid and then with purified water. It was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a viscous liquid. The resulting viscous liquid was recrystallized from methyl alcohol (120 g) to obtain compound (9) as a white solid (yield: 7.4 g, 86%).

[0071] The structure of compound (9) shown in formula (1-9) was confirmed by FT-IR analysis. -1 absorption due to the CH stretching of the benzene ring and at 3380cm -1 and 3473 cm -1 Absorption due to the stretching of amine NH was confirmed. 1 H-NMR analysis confirmed signals at 6.58-7.03 ppm derived from the benzene ring of the anilinyl group and a signal at 3.63 ppm derived from the NH2 of the anilinyl group. 29 Si-NMR analysis confirmed the signal of the anilinodimethylsilyl group at 8.44 ppm. GPC analysis revealed that Mn was 1,380 and Mw was 1,430.

[0072] TIFF2025115620000015.tif51154

[0073] Example 10 <Synthesis of the vinyl group-containing organosilicon compound of the present invention: compound (10)> Compound (1) (5.6 g; 5.01 mmol) obtained in Example 1, THF (150 g), and triethylamine (5.0 g; 50.0 mmol) were added to a 300 mL four-neck flask equipped with a dropping funnel, thermometer, and reflux condenser. The mixture was stirred under a nitrogen atmosphere. While maintaining the solution temperature at 28-41°C, vinyldimethylchlorosilane (7.26 g, 60.2 mmol) was added dropwise using the dropping funnel over approximately 5 minutes, and the mixture was allowed to react at room temperature for 4 hours. Purified water (30 g) was added dropwise using the dropping funnel. After stirring for 10 minutes, the organic and aqueous layers were separated using a separatory funnel. The organic layer was washed twice with 0.1 N hydrochloric acid and then with purified water. It was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a viscous liquid. The resulting viscous liquid was recrystallized from methyl alcohol (120 g) to obtain compound (10) as a white solid (yield: 6.8 g, 97%).

[0074] When the structure of compound (10) shown in formula (1-10) was confirmed, FT-IR analysis revealed a peak at 787 cm -1 Absorption due to the stretching of the C-Cl group was confirmed. 1 H-NMR analysis confirmed signals derived from vinyl groups at 5.79-6.06 ppm. 13 C-NMR analysis confirmed signals at 138.0 ppm and 123.8 ppm originating from two carbon atoms of the vinyl group. 29 Si-NMR analysis confirmed the signal of the vinyldimethylsilyl group at 10.09 ppm. GPC analysis revealed that Mn was 1,020 and Mw was 1,110.

[0075] TIFF2025115620000016.tif51137

[0076] Example 11 <Synthesis of the Polymer of the Present Invention: Polysiloxane (Polymer (11))> Organosilicon compound (2) (5 g) obtained by the synthesis method of Example 2, toluene (120 g), and a mixed solution (0.05 g) of n-hexylamine / 2-ethylhexanoic acid (molar ratio 1:2) were added to a 200 mL flask equipped with a reflux condenser and a stirrer. The mixture was heated in an oil bath under reflux with stirring under a nitrogen atmosphere for 16 hours. The mixture was then cooled to room temperature, filtered, and concentrated under reduced pressure using an evaporator to obtain a white solid polysiloxane (polymer (11)). GPC analysis of the resulting white solid revealed an Mn of 1,500 and an Mw of 3,300.

[0077] Example 12 <Synthesis of the Polymer of the Present Invention: Polysiloxane (Polymer (12))> A 200 mL flask equipped with a reflux condenser, a stirrer, and a Dean-Stark tube filled with molecular sieves 3A was charged with 5 g of the organosilicon compound (2) obtained by the synthesis method in Example 2 and 120 g of toluene. Furthermore, 0.05 g of p-toluenesulfonic acid monohydrate was added. The mixture was heated in an oil bath under reflux with stirring under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the mixture was separated and washed repeatedly with saturated aqueous sodium bicarbonate and ion-exchanged water until neutral. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure using an evaporator to obtain a white solid polysiloxane (polymer (12)). GPC analysis of the resulting white solid revealed an Mn of 33,000 and an Mw of 98,000.

[0078] Example 13 <Synthesis of the Polymer of the Present Invention: Polysiloxane (Polymer (13))> A 200 mL flask equipped with a reflux condenser and a stirrer was charged with organosilicon compound (2) (13.5 g) obtained by the synthesis method of Example 2, tetradecamethyldivinylheptasiloxane (11.2 g), and toluene (100 g). The mixture was stirred under a nitrogen atmosphere and heated in an oil bath to maintain the solution temperature at 70°C. Karstedt catalyst (2.0 μl) was then added using a microsyringe. 1 The reaction was terminated by confirming the disappearance of the vinyl group peak (5.79-6.06 ppm) by H-NMR. After concentrating under reduced pressure using an evaporator, the mixture was diluted with acetone, activated carbon (0.5 g) was added, and the mixture was stirred overnight at room temperature. After pressure filtration using a 0.2 μm filter, the mixture was concentrated under reduced pressure using an evaporator to obtain a colorless, syrup-like polysiloxane (polymer (13)). GPC analysis of the resulting syrup-like substance revealed that Mn was 4,400 and Mw was 40,500.

[0079] Example 14 <Synthesis of the Polymer of the Present Invention: Polysiloxane (Polymer (14))> Organosilicon compound (7) (5 g) obtained by the synthesis method of Example 7, glycidyl methacrylate (56 g), 3-methacryloxypropyltrimethoxysilane (39 g), 2,2'-azobis(methyl isobutyrate) (20.0 g), and diethylene glycol mono-n-butyl ether acetate (150 g) were added to a four-neck 500 mL flask equipped with a stirrer, and the mixture was heated at a polymerization temperature of 105°C for 4 hours to carry out polymerization. The reaction solution was cooled to room temperature, yielding a solution of polysiloxane (polymer (14)). A portion of the solution was sampled and analyzed by GPC, which revealed that the Mn was 3,000 and the Mw was 6,300.

[0080] Example 15 <Synthesis of the Polymer of the Present Invention: Polysiloxane (Polymer (15))> A 100 mL flask equipped with a reflux condenser and a stirrer was charged with 5 g of the organosilicon compound (10) obtained by the synthesis method of Example 10, 5 g of tetramethylhexaphenylpentasiloxane, and 50.0 g of toluene. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath to maintain the solution temperature at 70°C. Karstedt catalyst (2.0 μl) was added via a microsyringe, and stirring was continued for 1 hour. The mixture was then cooled to room temperature, yielding a solution of polysiloxane (polymer (15)). A portion of the solution was sampled and analyzed by GPC, revealing that the Mn was 5,400 and the Mw was 64,600.

[0081] Example 16 <Synthesis of the Polymer of the Present Invention: Polyamic Acid (Polymer (16))> A 200 mL four-neck separable flask equipped with a thermometer and stirrer was charged with 15.8 g of the organosilicon compound (9) obtained by the synthesis method of Example 9 and 95 g of dehydrated N-methyl-2-pyrrolidone as a reaction solvent. After the solids had completely dissolved, the mixture was placed under a nitrogen atmosphere at room temperature. 1.1 g of pyromellitic anhydride (tetracarboxylic dianhydride) was added. After stirring for 16 hours, 112 g of a homogeneous, transparent solution of polyamic acid (polymer (16)) with a solids concentration of 15.0 wt % was obtained. A portion of the solution was sampled and subjected to GPC analysis, which revealed that the Mn was 43,800 and the Mw was 107,500.

[0082] Example 17 <Synthesis of the Polymer of the Present Invention: Polyimide (Polymer (17))> 15 mL of the polyamic acid (polymer (16)) solution was taken with a micropipette and applied to a cleaned silicon substrate in a square area of at least 10 cm x 10 cm using an applicator. The substrate was then placed on a hot plate at 80°C for 30 minutes to evaporate the solvent, and heated in an oven at 150°C for 15 minutes. The oven temperature was then raised to 350°C over an hour, and the substrate was further heated at 350°C for 30 minutes for full curing (baking), yielding a transparent polyimide (polymer (17)) in the form of a cured film with a thickness of 200 μm.

[0083] Example 18 <Synthesis of the Polymer of the Present Invention: Polyester (Polymer (18))> A 300 mL four-neck separable flask equipped with a thermometer, stirrer, and nitrogen inlet tube was charged with 15.6 g of the organosilicon compound (6) obtained by the synthesis method of Example 6, 75.2 g of toluene, 3.2 g of 1,4-butadiol, and 0.05 g of titanium triisopropoxide, and the mixture was heated and stirred at 220°C for 1 hour. After cooling to room temperature, 94 g of a homogeneous, transparent solution of polyester (polymer (18)) with a solids concentration of 20.0 wt% was obtained. A portion of the solution was sampled and analyzed by GPC, revealing that the Mn was 4,300 and the Mw was 11,500. [Industrial Applicability]

[0084] The organosilicon compound of the present invention provides a silsesquioxane structure having a non-aromatic ring substituent at the apex of the cage structure. In the organosilicon compound of the present invention, by converting the terminal functional groups of the silsesquioxane structure having a non-aromatic ring substituent at the apex of the cage structure to functional groups such as amino groups, hydrosilyl groups, glycidyl groups, hydroxyl groups, acetoxy groups, carboxyl groups, methacryloxy groups, chloropropyl groups, vinyl groups, and siloxane groups, it is possible to obtain precursors of the polymers of the present invention that are useful in the development of useful optical components, dielectric materials, electronic component materials, and the like, and the structure having a non-aromatic ring substituent at the apex of the cage structure is extremely useful.< / gpc>

Claims

1. An organosilicon compound represented by formula (1): In formula (1), R is independently hydrogen, halogen, alkyl having 1 to 45 carbon atoms, or cycloalkyl having 4 to 18 carbon atoms; in the alkyl having 1 to 45 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH ２ - may be replaced by -O- or cycloalkylene having 4 to 18 carbon atoms, and in the cycloalkyl having 4 to 18 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms; at least one Y is a group selected from the groups represented by formula (2), and the remaining Y is hydrogen; and when at least two Y are groups represented by formula (2), they may be the same group or may be composed of at least two different groups; In formula (2), R １ and R ２ are independently hydrogen, alkyl having 1 to 45 carbon atoms, aryl having 6 to 45 carbon atoms, or arylalkyl having 7 to 45 carbon atoms; in the alkyl having 1 to 45 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one —CH ２ - may be replaced by -O-, -CH=CH-, cycloalkylene having 4 to 18 carbon atoms or cycloalkenylene having 4 to 18 carbon atoms; in the aromatic ring of the aryl having 6 to 45 carbon atoms and the arylalkylene having 7 to 45 carbon atoms, at least one hydrogen may be replaced by fluorine; in the alkylene of the arylalkyl having 7 to 45 carbon atoms, the number of carbon atoms is 1 to 39 and at least one -CH ２ - may be replaced by -O-, -CH=CH- or cycloalkylene; and Z is R １ It is a group, functional group or group having a functional group having the same definition as above.

2. The organosilicon compound is represented by the formula (1) and the formula (2), wherein R １ and R ２ 2. The organosilicon compound of claim 1, wherein is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, or phenyl.

3. The organosilicon compound is represented by formula (1) according to claim 1, wherein R is independently alkyl having 1 to 12 carbon atoms or cycloalkyl having 4 to 10 carbon atoms; in the alkyl having 1 to 12 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH ２ The organosilicon compound according to claim 2, wherein - may be replaced by -O- or a cycloalkylene having 4 to 10 carbon atoms, and in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by a fluorine atom or an alkyl having 1 to 3 carbon atoms.

4. The organosilicon compound according to claim 2, wherein, in the formula (1) of claim 1, R is independently a cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or an alkyl having 1 to 3 carbon atoms; and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or an alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

5. The organosilicon compound according to claim 2, wherein in the organosilicon compound represented by formula (1) of claim 1, all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms; and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

6. The organosilicon compound according to claim 2, wherein in the organosilicon compound represented by formula (1) of claim 1, all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms in which at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms, and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

7. 3. The organosilicon compound according to claim 2, wherein the organosilicon compound is represented by formula (1) in claim 1, and all R are cyclohexyl.

8. The organosilicon compound is represented by the formula (1) and the formula (2), wherein R １ and R ２ are independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, or phenyl; and Z is a functional group or a group having a functional group, the functional group being a group directly bonded to the Si atom selected from hydrogen, halogen, —OH, alkoxy, alkenyl, and fluorinated alkyl, the group having a functional group being a group composed of a divalent group and a functional group bonded to the Si atom via the divalent group, the divalent group being a divalent group selected from alkylene, alkylcycloalkylene, alkylenephenylene, alkylphenylene, and alkylphenylalkylene, and the alkylene and alkyl in these divalent groups have at least one —CH ２ - may be replaced by -O-, and the functional group bonded to the Si atom via a divalent group is hydrogen, halogen, -OH, fluorinated alkyl, alkoxy, carboxyl, 2-oxapropanedioyl, carboxylic anhydride residue, maleimide residue, acetoxy, vinyloxycarbonyl, allyloxycarbonyl, acryloyloxy, methacryloyloxy, polyalkyleneoxy, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, alkenyl, cycloalkenyl, -NH ２ , -CN, -NCO, -SH and -PH ２ 2. The organosilicon compound of claim 1, wherein the group is selected from the group consisting of:

9. The organosilicon compound is represented by formula (1) according to claim 1, wherein R is independently alkyl having 1 to 12 carbon atoms or cycloalkyl having 4 to 10 carbon atoms; in the alkyl having 1 to 12 carbon atoms, at least one hydrogen may be replaced by fluorine, and at least one -CH ２ The organosilicon compound according to claim 8, wherein - may be replaced by -O- or a cycloalkylene having 4 to 10 carbon atoms, and in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by a fluorine atom or an alkyl having 1 to 3 carbon atoms.

10. The organosilicon compound according to claim 8, wherein, in the organosilicon compound represented by formula (1) of claim 1, R is independently a cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or an alkyl having 1 to 3 carbon atoms; and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or an alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

11. The organosilicon compound according to claim 8, wherein the organosilicon compound is represented by formula (1) of claim 1, wherein all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms; in the cycloalkyl having 4 to 10 carbon atoms, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms; and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

12. The organosilicon compound according to claim 8, wherein in the organosilicon compound represented by formula (1) of claim 1, all R are the same group selected from cycloalkyl having 4 to 10 carbon atoms in which at least one hydrogen may be replaced by fluorine or alkyl having 1 to 3 carbon atoms, and when the cycloalkyl in which at least one hydrogen is replaced by fluorine or alkyl having 1 to 3 carbon atoms has hetero-substituted groups, the substituents may be the same or different groups.

13. 9. The organosilicon compound according to claim 8, wherein the organosilicon compound is represented by formula (1) in claim 1, and all R are cyclohexyl.

14. The organosilicon compound according to any one of claims 1 to 13, wherein Z in the organosilicon compound represented by formula (1) or (2) is an alkyl halide or a group having an alkyl halide.

15. The organosilicon compound is represented by the formula (1) or (2), wherein Z is alkenyl, or alkenyl, —OH, carboxyl, 2-oxapropanedioyl, oxiranyl, 3,4-epoxycyclohexyl, oxetanyl, and —NH ２ The organosilicon compound according to any one of claims 1 to 13, wherein the compound is a group having any one of the following formulas:

16. The organosilicon compound precursor according to claim 1, wherein all Y's in formula (1) are hydrogen.

17. A polymer obtainable by using the organosilicon compound according to claim 15.

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