Compound, method for producing compound, composition, surface treatment agent, article, and method for producing article

Abstract

Provided are a new compound capable of forming a surface treatment layer having excellent abrasion resistance, a method for producing the same, a composition and a surface treatment agent which contain said new compound, an article that has a surface treatment layer having excellent abrasion resistance, and a method for producing the same.　This compound is represented by formula (1) or formula (2).　(1): [R1-Q1-(SiR2 2-O)p1]q1-SiR2 q2-Q2-Z1-Si(R3)nL1 3-n (2): L1 3-n(R3)nSi-Z1-Q2-SiR2 2-O-(SiR4 2-O)p2-SiR2 2-Q2-Z1-Si(R3)nL1 3-n Wherein, R1 represents (R11)3Si- or the like, R11 represents a hydrocarbon group or the like, Q1 represents an oxygen atom or the like, R2 represents a hydrocarbon group, R3 represents a hydrocarbon group, R4 represents a hydrocarbon group or the like, p1 represents a number of 0-500, p2 represents a number of 0-500, q1 represents 1-3, q2 represents 0-2, q1+q2 equals 3, Q2 represents a single bond or the like, Z1 represents an alkylene group having 7-100 carbon atoms, L1 represents a hydrolyzable group or the like, and n represents 0-2.

Description

Compound, method for producing compound, composition, surface treatment agent, article, and method for producing article

[0001] The present disclosure relates to compounds, methods for producing compounds, compositions, surface treatment agents, articles, and methods for producing articles.

[0002] In recent years, there has been a demand for technologies that make surfaces of articles less susceptible to fingerprints and that make them easier to remove stains, in order to improve performance such as appearance and visibility. As a specific method, a method of performing a surface treatment on the surface of an article using a surface treatment agent is known.

[0003] Patent Document 1 describes, as a surface treatment agent, a specific siloxane group-containing silane compound having a divalent linear organopolysiloxane group and a hydrolyzable silyl group.

[0004] International Publication No. 2023 / 017830

[0005] Further improvements in surface treatment agents are required from the viewpoint of abrasion resistance and the like.

[0006] The present disclosure has been made in consideration of the above circumstances, and aims to provide a novel compound capable of forming a surface treatment layer with excellent abrasion resistance and a method for producing the same, a composition and surface treatment agent containing the novel compound, an article having a surface treatment layer with excellent abrasion resistance and a method for producing the same.

[0007] The present disclosure includes the following aspects: [1] A compound represented by the following formula (1) or the following formula (2): [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q ２ -SiR ２２ —O—(SiR ２ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2) However, R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group; R ４ are each independently a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ -, each p1 is independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ are each independently a single bond or a divalent linking group; Z １ are each independently an alkylene group having 7 to 100 carbon atoms; １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is each independently an integer of 0 to 2. [2] The Z １ is an alkylene group having 21 to 60 carbon atoms. ２ The compound according to [1] or [2], wherein -Q is represented by the following formula (Q1): １０ ｒ１ -R ５ ｒ２ -Q １１ ｒ３- ... (Q1) where Q １０ The side is connected to Si, and the Q １１ Side is Z １ and r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, and when r1, r2, and r3 are all 0, the Q ２ is a single bond, and Q １０ is an oxygen atom or an alkylene group, R ５ is -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ - and R ６ are each independently a hydrocarbon group, p3 is a number from 0 to 100, and Q １１ is a carbon-carbon bond, R ５ End of side or Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ a hydrocarbon group optionally having a bond selected from -, -O-, and -S-; R ａ１ are each independently a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group, provided that Z １ [4] A compound represented by the following formula (11): １ -Q １ -SiR ２ ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ... (11) where R １ is (R １１ ) ３ Si—, and R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ is an oxygen atom or an alkylene group, R ２ are each independently a hydrocarbon group; R ３are each independently a hydrocarbon group; ２ are each independently a single bond or a divalent linking group; Z １ are each independently an alkylene group having 7 to 100 carbon atoms; １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is each independently an integer of 0 to 2. [5] The Z １ is an alkylene group having 21 to 60 carbon atoms. ２ The compound according to [4] or [5], wherein -Q is represented by the following formula (Q1): １０ ｒ１ -R ５ ｒ２ -Q １１ ｒ３ - ... (Q1) where Q １０ The side is connected to Si, and the Q １１ Side is Z １ and r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, and when r1, r2, and r3 are all 0, the Q ２ is a single bond, and Q １０ is an oxygen atom or an alkylene group, R ５ is -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ - and R ６ are each independently a hydrocarbon group, p3 is a number from 0 to 100, and Q １１ is a carbon-carbon bond, R ５ End of side or Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ a hydrocarbon group optionally having a bond selected from -, -O-, and -S-; R ａ１ are each independently a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group, provided that Z １[7] A composition containing two or more compounds represented by the following formula (1), wherein R １ are each independently, (R １１ ) ３ Si- and R １１ are each independently a hydrocarbon group, and R １ are each independently, (R １１ ) ３ Si- and three R １１ A composition comprising a compound (1B) in which two or more of [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1) However, R １ are each independently １１ ) ３ Si—, and R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group, p1 is each independently a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ are each independently a single bond or a divalent linking group; Z １ are each independently an alkylene group having 7 to 100 carbon atoms; １are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is each independently an integer of 0 to 2. [8] The composition according to [7], containing the compound (1A) and the compound (1B) in a mass ratio of 50 to 99:50 to 1. [9] A composition comprising a compound according to any one of [1] to [6], or the composition according to [7] or [8], and a liquid medium.

[10] A surface treatment agent comprising a compound according to any one of [1] to [6], or the composition according to [7] or [8].

[11] A surface treatment agent comprising a compound according to any one of [1] to [6], or the composition according to [7] or [8], and a liquid medium.

[12] A method for producing an article, comprising surface-treating a substrate with a surface treatment agent comprising a compound according to any one of [1] to [6], or the composition according to [7] or [8], to produce an article having a surface-treated layer formed on the substrate.

[13] An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with a surface treatment agent comprising the compound according to any one of [1] to [6] or the composition according to [7] or [8].

[14] The article according to

[13] , which is an optical member.

[15] The article according to

[13] , which is a display or a touch panel.

[16] A method for producing the compound according to any one of [1] to [3], which comprises reacting a compound represented by the following formula (3) or a compound represented by the following formula (4) with a compound represented by the following formula (5) or a compound represented by the following formula (6) in the presence of a transition metal compound. [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z ３ -G １ …(3) G １ -Z ３ -Q ２ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q２ -Z ３ -G １ …(4) R ７ -MgX...(5) R ７ -Li ... (6) where R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ４ are each independently a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ -, each p1 is independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ are each independently a single bond or a divalent linking group; Z ３ are each independently an alkylene group; １ are each independently a halogen atom or a sulfonate group optionally substituted with a halogen atom, R ７ are each independently a hydrocarbon group having a carbon-carbon double bond, X is a halogen atom, and Z ３ and R ７ The total number of carbon atoms in [R] is 7 to 100.

[17] A method for producing the compound according to

[16] , in which the compound represented by formula (3) or the compound represented by formula (4) is reacted with 3 equivalents or more of the compound represented by formula (5) or the compound represented by formula (6).

[18] A compound represented by the following formula (7) or the following formula (8): １ -Q １ -(SiR ２ ２ -O) ｐ１ ]ｑ１ -SiR ２ ｑ２ -Q ２ -Z ４ -R ２０ …(7) R ２０ -Z ４ -Q ２ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z ４ -R ２０ ... (8) However, R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ４ are each independently a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ - and R ２０ are each independently a vinyl group, p1 is each independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ are each independently a single bond or a divalent linking group; Z ４ are each independently an alkylene group having 5 to 98 carbon atoms.

[0008] According to one embodiment of the present disclosure, there can be provided a novel compound capable of forming a surface treatment layer having excellent abrasion resistance and a method for producing the same, a composition and a surface treatment agent containing the novel compound, an article having a surface treatment layer having excellent abrasion resistance and a method for producing the same.

[0009] In this specification, numerical ranges indicated using "to" include the numerical values ​​before and after "to" as the minimum and maximum values, respectively. In numerical ranges described in stages in this specification, the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another staged numerical range. Furthermore, in numerical ranges described in this specification, the upper or lower limit value of that numerical range may be replaced with a value shown in the Examples. In this specification, a "surface treatment layer" refers to a layer formed on the surface of a substrate by surface treatment. In this specification, "Me" represents a methyl group, and "Et" represents an ethyl group. In this specification, when a compound or group is represented by a specific formula (X), the compound or group represented by the formula (X) may be referred to as compound (X) or compound X, and group (X) or group X, respectively. Note that when the same symbol exists in a single chemical formula, the same symbol may represent the same structure or different structures within the specified range.

[0010] The bonding direction of divalent groups represented in this specification is not limited unless otherwise specified. For example, when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-. In addition, the compound may be "X-CO-O-Z" or "X-O-CO-Z".

[0011] [Compound] The compound of the present disclosure is a compound represented by formula (1) described below or a compound represented by formula (2) described below. In this specification, the compound of the present disclosure refers to at least one of the compounds represented by formula (1) and formula (2).

[0012] When the compound of the present disclosure is used as a surface treatment agent, a surface treatment layer with excellent abrasion resistance can be formed. The reason for this is not clear, but is presumed to be as follows. The compound of the present disclosure contains a reactive silyl group: —Si(R ３ ) ｎ L １ ３－ｎBy having the above structure, it is possible to form a surface treatment layer that adheres closely to the surface of the substrate. １ It is believed that since the compound has adjacent long-chain alkylene groups represented by the formula (I) above, it can bond to the substrate at a higher density, and can form a surface treatment layer that is excellent not only in abrasion resistance but also in light resistance.

[0013] The compounds of the present disclosure will be described in detail below.

[0014] <Compound represented by formula (1)> [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(1) In formula (1), R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group, p1 is each independently a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ is a single bond or a divalent linking group, Z １ is an alkylene group having 7 to 100 carbon atoms; １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is an integer of 0 to 2.

[0015] In formula (1), R １ is (R １１ )３ Si-, a monovalent cyclic polysiloxane residue, or a monovalent cage polysiloxane residue.

[0016] R １ (R １１ ) ３ In Si-, R １１ is a hydrocarbon group or a trialkylsilyloxy group. １１ The hydrocarbon group in is preferably an alkyl group or an aryl group, more preferably an alkyl group. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 4. The same applies to the alkyl group in the trialkylsilyloxy group. R １１ The trialkylsilyloxy group of (R １２ ) ３ SiO—, and R １２ are each independently a hydrocarbon group. １２ The hydrocarbon group of R １１ The same as above can be mentioned. １１ Specific examples of include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group, with a methyl group or an ethyl group being preferred, and a methyl group being more preferred.

[0017] Multiple R １１ may be the same or different from each other, and from the viewpoint of ease of production, it is preferable that they are the same.

[0018] (R １１ ) ３Examples of the group represented by Si- include a methyldiethylsilyl group, a methylethylpropylsilyl group, a methylethylbutylsilyl group, a methyldipropylsilyl group, a methylpropylbutylsilyl group, a methyldibutylsilyl group, a dimethylethylsilyl group, a dimethylpropylsilyl group, a dimethylbutylsilyl group, a trimethylsilyl group, a triethylsilyl group, a tri-n-propylsilyl group, a tri-isopropylsilyl group, and a trialkylsilyloxy group having any of these groups. From the viewpoints of durability, water repellency, oil repellency, and fingerprint removability, (R １１ ) ３ Si- preferably has a branched structure, for example, three R １１ It is preferable that all of the groups are trimethylsilyloxy groups. From the viewpoint of forming a surface layer excellent in durability, water repellency, oil repellency, fingerprint removability, and acid resistance, it is preferable that (R １１ ) ３ Three R in Si- １１ Preferably, all of the groups are alkyl groups having 1 to 4 carbon atoms, more preferably methyl groups or ethyl groups, and even more preferably methyl groups.

[0019] R １ The monovalent cyclic organopolysiloxane residue in the formula (A1) is preferably a group represented by the following formula (A1): However, R ８ are each independently a hydrocarbon group, a hydrocarbon group having a substituent, or a trialkylsilyloxy group, and t1 is an integer of 1 to 4.

[0020] R ８The hydrocarbon group in is preferably an alkyl group or an aryl group, more preferably an alkyl group. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 4. The same applies to the alkyl group in the trialkylsilyloxy group. The three alkyl groups contained in the trialkylsilyloxy group may be the same or different from each other. In the hydrocarbon group having a substituent, examples of the substituent include a halogen atom, a hydroxyl group, an alkoxy group, a trialkylsilyloxy group, a trialkylsilyl group, an amino group, a nitro group, a cyano group, a sulfonyl group, and a trifluoromethyl group. R ８ The trialkylsilyloxy group of R １１ The same as above can be mentioned. ８ Specific examples of include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, a tert-butyl group, an isobutyl group, and a heptyl group, with a methyl group or an ethyl group being preferred, and a methyl group being more preferred.

[0021] Multiple R ８ may be the same or different from each other, but from the viewpoint of ease of production, it is preferable that they are the same.

[0022] Specific examples of the monovalent cyclic organopolysiloxane residue include the following groups, where * indicates the bonding position.

[0023]

[0024]

[0025] The monovalent cage-shaped organopolysiloxane residue is preferably a group represented by the following formula (A2). However, R ９ are each independently a hydrocarbon group, a hydrocarbon group having a substituent, or a trialkylsilyloxy group. * indicates the bonding position.

[0026] R ９The hydrocarbon group in is preferably an alkyl group or an aryl group, more preferably an alkyl group. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 4. The same applies to the alkyl group in the trialkylsilyloxy group. In the hydrocarbon group having a substituent, examples of the substituent include a halogen atom, a hydroxyl group, an alkoxy group, a trialkylsilyloxy group, a trialkylsilyl group, an amino group, a nitro group, a cyano group, a sulfonyl group, and a trifluoromethyl group. R ９ The trialkylsilyloxy group of R １１ The same as above can be mentioned. ９ Specific examples of include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group, with a methyl group or an ethyl group being preferred, and a methyl group being more preferred.

[0027] Multiple R ９ may be the same or different from each other, and from the viewpoint of ease of production, it is preferable that they are the same.

[0028] Specific examples of the monovalent cage-shaped organopolysiloxane residue include the following groups, where * indicates the bonding position.

[0029]

[0030] R １ is selected from the viewpoints of light resistance, abrasion resistance, liquid repellency, and ease of synthesis. １１ ) ３ Si- is preferred, and among these, (CH ３ ) ３ Si- or (CH ３ SiO) ３ Si- is preferred.

[0031] Q in formula (1) １ is an oxygen atom or an alkylene group. １The alkylene group in Q may be a linear, branched, or cyclic alkyl group, and from the viewpoints of light resistance and abrasion resistance, a linear alkylene group is preferred. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 12, and even more preferably 1 to 6. Specific examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, and a hexylene group. １ From the viewpoints of abrasion resistance, light resistance and liquid repellency, is preferably an oxygen atom or a linear alkylene group having 1 to 6 carbon atoms, more preferably an oxygen atom, a methylene group or an ethylene group, and even more preferably an oxygen atom.

[0032] (SiR of formula (1) ２ ２ -O) ｐ１ represents a linear organopolysiloxane, and p1 is a number from 0 to 500. ２ ２ -O) ｐ１ and -SiR ２ ２ - in R ２ are each independently a hydrocarbon group.

[0033] R ２ The hydrocarbon group in is preferably an alkyl group or an aryl group. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, but a linear alkyl group or a branched alkyl group is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 4. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group. Specific examples of the aryl group include a phenyl group and a naphthyl group. R ２ Among these, from the viewpoints of abrasion resistance, light resistance and liquid repellency, a methyl group, an ethyl group, a tert-butyl group or a phenyl group is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is even more preferred.

[0034] Multiple R ２ may be the same or different from each other, but from the viewpoint of ease of production, it is preferable that they are the same.

[0035] p1 is a number from 0 to 500, and from the viewpoint of excellent liquid repellency and durability of the compound, a number from 1 to 300 is preferable, a number from 1 to 200 is more preferable, a number from 3 to 50 is further preferable, and a number from 5 to 15 is particularly preferable. １ But, R １１ are all trialkylsilyloxy groups (R １１ ) ３ In the case of Si-, p1 is preferably a number from 0 to 500. １ But, R １１ At least one of R １ ) ３ In the case of Si-, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, p1 is preferably a number from 1 to 500. ２ ２ The number p1 of repeating units represented by (p1) is an average value calculated from data obtained by measuring a compound having the structure p1 by nuclear magnetic resonance (NMR).

[0036] q1 is an integer of 1 to 3, q2 is an integer of 0 to 2, and q1+q2 is 3. More specifically, when q1 is 1, q2 is 2, when q1 is 2, q2 is 1, and when q1 is 3, q2 is 0. When q1 is 2 or 3, multiple [R １ -Q １ -(SiR ２ ２ -O) ｐ１ The structures represented by the formula [1] may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0037] Q in formula (1) ２ is a single bond or a divalent linking group. Examples of the divalent linking group include a divalent hydrocarbon group, a divalent heterocyclic group, —O—, —S—, and —SO ２ -, -NR ａ１ -, -C(=O)-, -C(=O)O-, -C(=O)NR ａ１ -, -C(=O)S-, -(SiR ６ ２ -O) ｐ３ -SiR６ ２ - and groups formed by combining two or more of these. ａ１ are each independently a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group, and R ６ are each independently a hydrocarbon group, and p3 is a number from 0 to 100. ２ When represents a divalent linking group, Z １ The alkylene group is not present at the terminal end of the alkylene group.

[0038] The above Q ２ In the above formula, examples of the divalent hydrocarbon group include a divalent saturated hydrocarbon group, a divalent aromatic hydrocarbon group, an alkenylene group, and an alkynylene group. The divalent saturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include an alkylene group. The divalent saturated hydrocarbon group preferably has 1 to 20 carbon atoms. The divalent aromatic hydrocarbon group preferably has 5 to 20 carbon atoms, and examples thereof include a phenylene group and a divalent biphenyl group (-C ６ H ５ -C ６ H ５ The divalent hydrocarbon group may be an alkenylene group having 2 to 20 carbon atoms or an alkynylene group having 2 to 20 carbon atoms.

[0039] Examples of the heterocyclic ring in the divalent heterocyclic group include a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring.

[0040] Here, R ａ１ is a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group. Examples of the hydrocarbon group having 1 to 6 carbon atoms include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group. The alkyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group, but is preferably a linear alkyl group. R ６ The hydrocarbon group in ２p3 is a number from 0 to 100, and is an average value calculated from data obtained by measuring a compound having the structure of p3 by nuclear magnetic resonance (NMR).

[0041] Q ２ may be a group in which two or more of the above-mentioned divalent hydrocarbon groups, divalent heterocyclic groups, and various bonds such as -O- are combined. The group in which two or more of these are combined may, for example, be a group in which one or more of these various bonds are combined, ２ The Si side end in Z １ The group may be one having a bond at the terminal of the alkyl group or between atoms (for example, between carbon atoms) in a divalent hydrocarbon group and a divalent heterocyclic group. More specifically, examples of groups having a combination of two or more of these include various bonds (-O-, -S-, -SO ２ -, -NR ａ１ -, -C(=O)-, -OC(=O)-, -C(=O)O-, -C(=O)S-, -C(=O)NR ａ１ -, -NR ａ１ C(=O)-, -NR ａ１ C(=O)NR ａ１ -, -NR ａ１ C(=O)O-, -OC(=O)NR ａ１ -, -SO ２ NR ａ１ - and -NR ａ１ SO ２ an alkylene group having —O—SiR ６ ２ -, -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ - are listed.

[0042] Q ２ From the viewpoint of abrasion resistance, -Q is preferably a group represented by the following formula (Q1): １０ ｒ１ -R ５ ｒ２ -Q １１ ｒ３ - ... (Q1) where Q １０ The side is connected to Si, and the Q １１ Side is Z １and r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, and when r1, r2, and r3 are all 0, the Q ２ is a single bond, and Q １０ is an oxygen atom or an alkylene group, R ５ is -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ - and R ６ are each independently a hydrocarbon group, p3 is a number from 0 to 100, and Q １１ is a carbon-carbon bond, R ５ End of side or Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ a hydrocarbon group optionally having a bond selected from -, -O-, and -S-; R ａ１ are each independently a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group, provided that Z １ The alkylene group does not exist at the terminal of the alkylene group.

[0043] Q １０ is an oxygen atom or an alkylene group. １０ The alkylene group in Q may be a linear, branched, or cyclic alkyl group, and from the viewpoints of light resistance and abrasion resistance, a linear alkylene group is preferred. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 12, and even more preferably 1 to 6. Specific examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, and a hexylene group. １０ In terms of abrasion resistance, light resistance and liquid repellency, is preferably an oxygen atom or a linear alkylene group having 1 to 6 carbon atoms, more preferably an oxygen atom, a methylene group or an ethylene group.

[0044] R ５ is -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -, where R６ are each independently a hydrocarbon group, and p3 is a number from 0 to 100. ６ and p3 are as described above.

[0045] Q １１ is a carbon-carbon bond, R ５ End of side or Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ R is a hydrocarbon group which may have a bond selected from -, -O-, and -S-. ａ１ is as described above. Examples of the hydrocarbon group include a divalent saturated hydrocarbon group, a divalent aromatic hydrocarbon group, an alkenylene group, and an alkynylene group. The divalent saturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include an alkylene group. The divalent saturated hydrocarbon group preferably has 1 to 20 carbon atoms. The divalent aromatic hydrocarbon group preferably has 5 to 20 carbon atoms, and examples thereof include a phenylene group and a divalent biphenyl group (-C ６ H ５ -C ６ H ５ The divalent hydrocarbon group may be an alkenylene group having 2 to 20 carbon atoms or an alkynylene group having 2 to 20 carbon atoms. ２ Is Z １ Therefore, Q does not have an alkylene group at the end of the １１ When the hydrocarbon group in represents an alkylene group, Q １１ Is Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ It is a hydrocarbon group having a bond selected from --, --O-- and --S--.

[0046] Q １１ Examples of R include the following groups. Here, n is, for example, 1 to 20, and * is the bonding position. ａ１ is as described above.

[0047] Specific examples of the group represented by the formula (Q1) include a single bond and groups represented by the following formulas (Q1-1) to (Q1-10). * indicates the bonding position with the Si side, and ** indicates the bonding position with the Z １ In the formulas (Q1-1) to (Q1-3), (Q1-6) to (Q1-7), and (Q1-9), Z １ In other words, in these formulas, Q does not have an alkylene group at the end of the １１ When represents an alkylene group, Z １ The terminals of the -OR groups have the various bonds described above. ５ -Q １１ -**...(Q1-1) *-Z ａ１ -R ５ -Q １１ -**...(Q1-2) *-R ５ -Q １１ -**...(Q1-3) *-OR ５ -**...(Q1-4) *-Z ａ１ -R ５ -**...(Q1-5) *-O-Q １１ -**...(Q1-6) *-Z ａ１ -Q １１ -**...(Q1-7) *-R ５ -**...(Q1-8) *-Q １１ -** ... (Q1-9) *-O-** ... (Q1-10) Here, Z in formulas (Q1-1) to (Q1-10) ａ１ is an alkylene group, and R ５ and Q １１ are the same as the respective groups in formula (Q1).

[0048] Z in formula (1) １ is an alkylene group having 7 to 100 carbon atoms, and is preferably a linear alkylene group. １ The number of carbon atoms in the alkylene group represented by Z is preferably 12 to 60 from the viewpoint of abrasion resistance, more preferably 21 to 60 from the viewpoint of durability, and even more preferably 21 to 36 from the viewpoint of ease of production. １ The number of carbon atoms in the alkylene group represented by Z may be 23 to 60, or may be 23 to 36.１ The alkylene group represented by may or may not have a substituent, but preferably has no substituent from the viewpoint of abrasion resistance and light resistance. Examples of the substituent that the alkylene group has include a halogen atom, a hydroxyl group, an alkoxy group, a trialkylsilyloxy group, a trialkylsilyl group, an amino group, a nitro group, a cyano group, a sulfonyl group, and a trifluoromethyl group. １ When the alkylene group represented by Z has a substituent, the number of carbon atoms of the substituent is not included in the number of carbon atoms of the alkylene group. １ The number of carbon atoms of the alkylene group represented by means excluding the number of carbon atoms of the substituent.

[0049] Si(R ３ ) ｎ L １ ３－ｎ represents a reactive silyl group, R ３ are each independently a hydrocarbon group, and L １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is an integer of 0 to 2. ３ Examples of the hydrocarbon group of R include an alkyl group, a cycloalkyl group, an alkenyl group, and an allyl group. From the viewpoint of ease of synthesis, a saturated hydrocarbon group is preferred, and an alkyl group is more preferred. ３ The number of carbon atoms is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2.

[0050] L １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group. A hydrolyzable group is a group that becomes a hydroxyl group through a hydrolysis reaction. That is, Si-L １ The hydrolyzable silyl group represented by the formula (I) becomes a silanol group represented by Si—OH through a hydrolysis reaction. The silanol groups further react with each other to form Si—O—Si bonds. Furthermore, the silanol groups can undergo a dehydration condensation reaction with silanol groups derived from oxides present on the surface of the substrate to form Si—O—Si bonds.

[0051] Examples of hydrolyzable groups include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, and isocyanato groups (-NCO). The alkoxy group preferably has 1 to 6 carbon atoms, and more preferably has 1 to 4 carbon atoms. The aryloxy group is preferably an aryloxy group having 3 to 10 carbon atoms. However, the aryl group of the aryloxy group may be a heteroaryl group. The halogen atom is preferably a chlorine atom. The acyl group is preferably an acyl group having 1 to 6 carbon atoms. The acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms.

[0052] The group having a hydrolyzable group may be, for example, any of the groups having a hydrolyzable group exemplified above. Ａ -L Ｂ is preferred. Ａ is an alkylene group, and L Ｂ is a hydrolyzable group. The alkylene group preferably has 1 to 10 carbon atoms. Ｂ The hydrolyzable group represented by the formula １ The preferred embodiments are also the same as those of the hydrolyzable group represented by the following formula: Specific examples of the group having a hydrolyzable group include —O—CH ２ CH ２ -OCH ３ Thus, the group having a hydrolyzable group may be an alkylene oxide-modified alkoxy group. The alkylene oxide-modified alkoxy group is an alkylene oxide-modified alkoxy group having a structure of -(O-R ４１ ) ｎ１１ -L １０ Here, a group represented by R ４１ is an alkylene group having 1 to 10 carbon atoms, and L １０ is an alkoxy group having 1 to 6 carbon atoms, and n11 is an integer of 1 to 6. ４１ is preferably an alkylene group having 1 to 6 carbon atoms, and n11 is preferably 1.

[0053] Among them, L １ From the viewpoint of ease of production of the compound, L is preferably an alkoxy group having 1 to 4 carbon atoms, an alkylene oxide-modified alkoxy group, or a halogen atom. １is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an ethoxy group or a methoxy group, in terms of less outgassing during application and better storage stability of the compound.

[0054] n is an integer of 0 to 2, preferably 0 or 1, and more preferably 0. １ When n is 1 or less, the number of L groups in one molecule is 1, and the number of L groups in one molecule is 1. １ From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable to use a plurality of L １ When n is 2, multiple R ３ may be the same or different from each other. From the viewpoint of availability of raw materials and ease of production of the compound, it is preferable to use a plurality of R ３ are preferably the same.

[0055] From the above, examples of the compound represented by formula (1) include compounds represented by the following formulas: When q1 is 1, R １ —O—(SiR ２ ２ -O) ｐ１ -SiR ２ ２ —O—(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ... (1-1a) R １ —O—(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ )ｎ L １ ３－ｎ …(1-2a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-3a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-4a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-5a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １３－ｎ …(1-6a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-7a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-8a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-9a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z １ -Si(R ３ ) ｎ L１ ３－ｎ …(1-10a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-11a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-12a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-13a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-14a) R１ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-15a) R １ -O-(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-16a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-17a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-18a) R １ -Z ２ -(SiR ２２ -O) ｐ１ -SiR ２ ２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-19a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-20a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-21a) R １ -Z ２ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２ -O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-22a) ・When q1 is 2 [R １ -O-(SiR ２ ２ -O) ｐ１ ２ -SiR ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ ​-Si(R ３ ) ｎ L １ ３－ｎ …(1-1b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-2b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-3b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-4b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z １ -Si(R ３ ) ｎ L１ ３－ｎ …(1-5b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-6b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-7b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-8b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -(SiR６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-9b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-10b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-11b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-12b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-13b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-14b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-15b) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-16b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ…(1-17b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-18b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-19b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-20b) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ２ -SiR ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-21b) [R １ -Z ２ -(SiR ２ ２-O) ｐ１ ] ２ -YesR ２ -O-Z １ -Yes (R) ３ ) ｎ L １ ３－ｎ …(1-22ｬ) ・q1が3ととは [R １ -O-(YesR) ２ ２ -O) ｐ１ ] ３ -Si-O-(SiR ６ ２ -O) ｐ３ -YesR ６ ２ -Q １１ -Z １ -Yes (R) ３ ) ｎ L １ ３－ｎ …(1-1c) [R] １ -O-(YesR) ２ ２ -O) ｐ１ ] ３ -Yes-(YesR ６ ２ -O) ｐ３ -YesR ６ ２ -Q １１ -Z １ -Yes (R) ３ ) ｎ L １ ３－ｎ …(1-2c) [R] １ -O-(YesR) ２ ２ -O) ｐ１ ] ３ -Si-O-(SiR ６ ２ -O) ｐ３ -YesR ６ ２ -Z １ -Yes (R) ３ ) ｎ L １ ３－ｎ …(1-3c) [R] １ -O-(YesR) ２ ２ -O) ｐ１ ] ３ -Yes-(YesR６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-4c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-5c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-O-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-6c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-7c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-O-(SiR ６ ２ -O)ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-8c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-9c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-10c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-11c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-12c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-13c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-14c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-15c) [R １ -O-(SiR ２ ２ -O) ｐ１ ] ３ -Si-O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-16c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-17c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-18c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-19c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-20c) [R １ -Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(1-21c) [R １-Z ２ -(SiR ２ ２ -O) ｐ１ ] ３ -Si-O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(1-22c) However, each group in these formulae has the same meaning as each group in the above-mentioned formula (1) and formula (Q1), and the preferred embodiments are also the same. ２ is Q in formula (1) １ In these formulae, Z has the same meaning as the alkylene group represented by １ Q in the adjacent position of １１ and the Q １１ represents an alkylene group, the alkylene group is １ and Z １ The alkylene group does not exist at the terminal of the alkylene group. The structures represented by the above formulae may be overlapped.

[0056] For example, compounds 1-4 and 2-3 in the examples described later are specific examples of compounds represented by the above formula (1-5a). Compounds 3-5, 4-4, and 5-2 in the examples described later are specific examples of compounds represented by the above formula (1-3b). Compound 6-5 in the examples described later is a specific example of a compound represented by the above formula (1-3c). Compound 7-4 in the examples described later is a specific example of a compound represented by the above formula (1-1b). Compound 8-3 in the examples described later is a specific example of a compound represented by the above formula (1-15a).

[0057] The compound represented by the formula (1) may have an embodiment in which p1 is 0 and q1 is 1. Examples of such compounds include compounds represented by the following formula (11). A surface treatment layer using the following compound (11) has excellent properties such as abrasion resistance and also has improved acid resistance. R １ -Q １ -SiR ２ ２ -Q ２-Z １ -Si(R ３ ) ｎ L １ ３－ｎ ... (11) where R １ is (R １１ ) ３ Si—, and R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ is an oxygen atom or an alkylene group, R ３ are each independently a hydrocarbon group; ２ are each independently a single bond or a divalent linking group; Z １ are each independently an alkylene group having 7 to 100 carbon atoms; １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; and n is each independently an integer of 0 to 2.

[0058] Each symbol in formula (11) is the same as that in formula (1). Preferred embodiments of formula (11) will be described below. １１ Among these, R is preferably a hydrocarbon group, more preferably an alkyl group having 1 to 4 carbon atoms, further preferably a methyl group or an ethyl group, and particularly preferably a methyl group. ２ Among these, an alkyl group having 1 to 4 carbon atoms is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is even more preferred. １ Among these, Q is preferably an oxygen atom or a linear alkylene group having 1 to 6 carbon atoms, more preferably an oxygen atom, a methylene group, or an ethylene group, and even more preferably an oxygen atom. ２ is preferably a group represented by the formula (Q1), and preferred embodiments of the formula (Q1) are the same as those in the compound (1). １ is an alkylene group having 7 to 100 carbon atoms, and is preferably a linear alkylene group. １ The number of carbon atoms in the alkylene group represented by Z is preferably 12 to 60, more preferably 13 to 60, still more preferably 13 to 36, and particularly preferably 21 to 36. １The number of carbon atoms in the alkylene group represented by R may be 23 to 60, or may be 23 to 36. ３ , L １ and n have the same preferred embodiments as those in formula (1).

[0059] Examples of the compound represented by formula (11) include compounds represented by the following formula: (R １１ ) ３ Si—O—SiR ２ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-1b) (R １１ ) ３ Si—O—SiR ２ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-2b) (R １１ ) ３ Si—O—SiR ２ ２ -O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-3b) (R １１ ) ３ Si—O—SiR ２ ２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-4b) (R １１ ) ３ Si-L １１ -SiR ２ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-5b) (R １１ ) ３ Si-L１１ -SiR ２ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-6b) (R １１ ) ３ Si-L １１ -SiR ２ ２ -O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-7b) (R １１ ) ３ Si-L １１ -SiR ２ ２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(11-8b) where, in the above formula, L １１ is an alkylene group having 1 to 6 carbon atoms, and the other symbols are as defined above.

[0060] <Compound represented by formula (2)> L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q ２ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ...(2) In formula (2), R ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group; R ４ are each independently a hydrocarbon group, or R １ -Q１ -(SiR ２ ２ -O) ｐ１ - and R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ are each independently a hydrocarbon group or a trialkylsilyloxy group, p1 is a number from 0 to 500, p2 is a number from 0 to 500, and Q １ each independently represents an oxygen atom or an alkylene group; ２ are each independently a single bond or a divalent linking group; Z １ are each independently an alkylene group having 7 to 100 carbon atoms; １ are each independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; and n is each independently an integer of 0 to 2.

[0061] In formula (2), R ２ , R ３ , Q ２ , Z １ , L １ , n have the same meanings as the groups in formula (1), and preferred embodiments are also the same.

[0062] In formula (2), p2 is a number from 0 to 500. From the viewpoint of excellent liquid repellency and durability of the compound, p2 is preferably a number from 0 to 300, more preferably a number from 0 to 200, even more preferably a number from 2 to 50, and particularly preferably a number from 4 to 15. In formula (2), "(SiR ４ ２ The number p2 of repeating units represented by (a)-(-O)) is an average value calculated from data obtained by measuring a compound having the structure p2 by nuclear magnetic resonance (NMR).

[0063] In formula (2), R ４ is a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ The hydrocarbon group is R ２The hydrocarbon groups represented by R are the same as those represented by R, and the preferred embodiments are also the same. １ -Q １ -(SiR ２ ２ -O) ｐ１ The meaning of "-" is the same as in formula (1), and the preferred embodiments are also the same.

[0064] Examples of the compound represented by formula (2) include compounds represented by the following formula: In the following formula, the two Q ２ Although the cases where both represent the same structure are shown, they may also have different structures. １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q １１ -SiR ６ ２ -(O-SiR ６ ２ ) ｐ３ —O—SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ —O—(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ... (2-1) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q １１ -SiR ６ ２ -(O-SiR ６ ２ ) ｐ３ -Z ａ１ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR２ ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-2) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q １１ -SiR ６ ２ -(O-SiR ６ ２ ) ｐ３ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-3) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -SiR ６ ２ -(O-SiR ６ ２ ) ｐ３ -O-SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -O-(SiR ６ ２ -O) ｐ３ -SiR ６２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-4) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -SiR ６ ２ -(O-SiR ６ ２ ) ｐ３ -Z ａ１ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Z ａ１ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-5) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q １１ -O-SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -O-Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-6) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q １１ -Z ａ１ -SiR ２ ２ -O-(SiR ４２ -O) ｐ２ -SiR ２ ２ -Z ａ１ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-7) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -SiR ６ ２ -(O-SiR ６ ２ ) ｐ３ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-8) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q １１ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q １１ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-9) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -O-SiR ２ ２ -O-(SiR４ ２ -O) ｐ２ -SiR ２ ２ -O-Z １ -Si(R ３ ) ｎ L １ ３－ｎ ... (2-10) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ …(2-11)

[0065] Examples of the compound represented by formula (2) include the following compounds: ａ is 6 to 99, and n ｂ is, for example, 0 to 450. ４ is as described above.

[0066]

[0067] The number average molecular weight (Mn) of the compound of the present disclosure is preferably 500 to 20,000, more preferably 600 to 18,000, and even more preferably 700 to 15,000. When Mn is 500 or more, the abrasion resistance of the surface treatment layer is superior. When Mn is 20,000 or less, the viscosity can be easily adjusted within an appropriate range and solubility is improved, resulting in excellent handleability during film formation.

[0068] [Method for producing the compound] The method for producing the present compound is not particularly limited, but it is preferable to use a production method in which a compound represented by the following formula (7) or (8) is hydrosilylated in the presence of a metal compound. The compound represented by the following formula (7) corresponds to the compound represented by the above formula (1), and the compound represented by the following formula (8) corresponds to the compound represented by the above formula (2). [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z ４ -R ２０ …(7) R ２０ -Z ４ -Q ２ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z ４ -R ２０ ... (8) However, R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ４ are each independently a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ - and R ２０are each independently a vinyl group, p1 is each independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ are each independently a single bond or a divalent linking group; Z ４ are each independently an alkylene group having 5 to 98 carbon atoms.

[0069] Here, R １ , Q １ , R ２ , R ４ , p1, p2, q1, q2, Q ２ R has the same meaning as each group in formula (1) and formula (2), and preferred embodiments are also the same. ２０ is a vinyl group. ４ is an alkylene group having 5 to 98 carbon atoms, and １ It is an alkylene group having two fewer carbon atoms than Z. ４ The number of carbon atoms in the alkylene group represented by Z is preferably 10 to 58 from the viewpoint of abrasion resistance, more preferably 19 to 58 from the viewpoint of durability, and even more preferably 19 to 34 from the viewpoint of ease of production. ４ The alkylene group represented by may or may not have a substituent, but preferably has no substituent from the viewpoint of abrasion resistance and light resistance. Examples of the substituent that the alkylene group has include a halogen atom, a hydroxyl group, an alkoxy group, a trialkylsilyloxy group, a trialkylsilyl group, an amino group, a nitro group, a cyano group, a sulfonyl group, and a trifluoromethyl group. １ When the alkylene group represented by Z has a substituent, the number of carbon atoms of the substituent is not included in the number of carbon atoms of the alkylene group. ４ The number of carbon atoms of the alkylene group represented by means excluding the number of carbon atoms of the substituent.

[0070] As the metal compound, any known metal catalyst used in hydrosilylation can be used as appropriate, such as a known Pt catalyst, Ru catalyst, Rh catalyst, Fe catalyst, or Co catalyst.

[0071] Here, the compound represented by the above formula (7) or formula (8) can be obtained by reacting a compound represented by the following formula (3) or a compound represented by the following formula (4) with a compound represented by the following formula (5) or a compound represented by the following formula (6) in the presence of a transition metal compound. Note that the compound represented by the following formula (3) corresponds to the compound represented by the above formula (1), and the compound represented by the following formula (4) corresponds to the compound represented by the above formula (2). [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z ３ -G １ …(3) G １ -Z ３ -Q ２ -SiR ２ ２ —O—(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z ３ -G １ …(4) R ７ -MgX...(5) R ７ -Li ... (6) where R １ are each independently １１ ) ３ Si—, a monovalent cyclic polysiloxane residue, or a monovalent cage-like polysiloxane residue, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ are each independently an oxygen atom or an alkylene group; ２ are each independently a hydrocarbon group; R ４ are each independently a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１-, each p1 is independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, and Q ２ are each independently a single bond or a divalent linking group; Z ３ are each independently an alkylene group; １ are each independently a halogen atom or a sulfonate group optionally substituted with a halogen atom, R ７ are each independently a hydrocarbon group having a carbon-carbon double bond, X is a halogen atom, and Z ３ and R ７ The total number of carbon atoms is 7 to 100.

[0072] Here, in the above formula (3) and formula (4), R １ , R １１ , R ２ , R ４ , Q １ , Q ２ , p1, p2, q1, and q2 have the same meanings as the groups in formula (1) and formula (2), and preferred embodiments are also the same.

[0073] Z ３ are each independently an alkylene group, and R ７ are each independently a hydrocarbon group having a carbon-carbon double bond, and Z ３ and R ７ The total number of carbon atoms in -Z in formula (3) and formula (4) is 7 to 100. ３ -G １ The part is R shown in formula (5). ７ -MgX or R shown in formula (6) ７ -Li (for example, Grignard reaction) to form -Z ４ -R ２０ (Z ４ is an alkylene group having 5 to 98 carbon atoms, R ２０ forms a vinyl group) moiety. ４ -R ２０By hydrosilylating the Z moiety in the presence of a metal compound, the present compounds shown in formula (1) and formula (2) can be obtained. ３ and R ７ The structure of the compound (more specifically, Z １ The structure of G can be selected appropriately. １ are each independently a halogen atom or a sulfonate group which may be substituted with a halogen atom. X is a halogen atom. Examples of halogen atoms include Cl, Br, and I. The sulfonate group which may be substituted with a halogen atom is not particularly limited as long as it functions as a leaving group in a nucleophilic substitution reaction with a nucleophile represented by formula (5) or formula (6). Examples of sulfonate groups include a nonafluorobutanesulfonate group, a trifluoromethanesulfonate group, a fluorosulfonate group, a p-toluenesulfonate group, and a methanesulfonate group.

[0074] In the method for producing a compound of the present disclosure, it is preferable to react a compound represented by formula (3) or a compound represented by formula (4) with a compound represented by formula (5) or a compound represented by formula (6) in an amount of 3 or more equivalents. By using 3 or more equivalents of a compound represented by formula (5) or a compound represented by formula (6), the formation of by-products can be easily suppressed. Examples of by-products include dimers that are thought to be formed by reaction between compounds represented by formula (3) or between compounds represented by formula (4). From the viewpoint of suppressing by-products, it is more preferable to use 5 to 20 equivalents, and even more preferable to use 10 to 15 equivalents, of a compound represented by formula (5) or a compound represented by formula (6) relative to a compound represented by formula (3) or a compound represented by formula (4).

[0075] Here, the method for producing the compound represented by formula (3) and the compound represented by formula (4) is not particularly limited. For example, １ -Q １ -(SiR ２ ２ -O) ｐ１ -SiR ２ ２-Q ２ -Z ３ -G １ The compound represented by formula (3) or (4) can be produced by adding a structure corresponding to the following: The reaction conditions may be appropriately adjusted with reference to the examples described below.

[0076] Furthermore, the method for producing the compound of the present disclosure represented by formula (1) or formula (2) by introducing a reactive silyl group from the compound represented by formula (5) or formula (6) is not particularly limited, and a conventionally known method can be used as appropriate. The reaction conditions can be adjusted as appropriate.

[0077] The compound of the present disclosure may be one type of compound represented by formula (1) or formula (2), or may be a composition containing two or more types (hereinafter also referred to as "composition 1"). Composition 1 includes a combination of two or more types of compounds represented by formula (1); a combination of one or more types of compounds represented by formula (1) and one or more types of compounds represented by formula (2); and a combination of two or more types of compounds represented by formula (2). Composition 1 includes a compound represented by formula (1) where R １ are each independently, (R １１ ) ３ Si- and R １１ are each independently a compound (1A) which is a hydrocarbon group, and R １ are each independently, (R １１ ) ３ Si- and three R １１ and a compound (1B) in which two or more of the above are trialkylsilyloxy hydrocarbon groups and the remainder are hydrocarbon groups. Among these, a composition containing only the compound (1A) and the compound (1B) is more preferred. In the compound (1A), p1 is preferably a number of 1 or more, more preferably a number from 1 to 100, even more preferably a number from 1 to 50, particularly preferably a number from 1 to 20, and most preferably a number from 5 to 15. In the compound (1B), p1 is preferably a number from 0 to 5, more preferably a number from 0 to 2.

[0078] There are no particular restrictions on the mass ratio of the two or more compounds in the composition 1. For example, the mass ratio of the compound (1A) to the compound (1B) is preferably 50 to 99:50 to 1, more preferably 70 to 99:30 to 1, and particularly preferably 80 to 99:20 to 1.

[0079] [Composition] The composition of the present disclosure may contain a compound of the present disclosure, and components other than the compound of the present disclosure are not particularly limited. That is, the composition of the present disclosure may contain at least one of a compound represented by formula (1) and a compound represented by formula (2). The composition of the present disclosure may contain both a compound represented by formula (1) and a compound represented by formula (2). That is, the composition of the present disclosure may contain one or more compounds of the present disclosure (i.e., the above-mentioned composition 1). Another embodiment of the composition of the present disclosure includes a compound of the present disclosure and a liquid medium. When a liquid medium is included, the composition of the present disclosure may be in a liquid state, and may be a solution or a dispersion. A composition containing a compound represented by formula (1) or formula (2) and a liquid medium may be referred to as composition 2, and the above-mentioned composition 1 may also be simply referred to as the composition. The composition of the present disclosure may contain a compound of the present disclosure, and may include impurities such as by-products produced in the manufacturing process of the compound of the present disclosure.

[0080] The content of the compound of the present disclosure is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass, relative to the total amount of the composition of the present disclosure. In the case of a composition of the present disclosure used in a wet coating method, the content of the compound of the present disclosure may be 0.01 to 10% by mass, 0.02 to 5% by mass, 0.03 to 3% by mass, or 0.05 to 2% by mass, relative to the total amount of the composition of the present disclosure. The composition of the present disclosure may contain only one type of liquid medium, or two or more types of liquid medium.

[0081] The liquid medium is preferably an organic solvent.

[0082] Examples of organic solvents include compounds consisting of only hydrogen atoms and carbon atoms, and compounds consisting of only hydrogen atoms, carbon atoms, and oxygen atoms, and specific examples include hydrocarbon organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, glycol organic solvents, and alcohol organic solvents. Among these, the organic solvent is preferably a hydrocarbon organic solvent or an ester organic solvent.

[0083] Specific examples of hydrocarbon organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexyl, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene. Specific examples of ketone organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, and isophorone. Specific examples of ether organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.Specific examples of ester-based organic solvents include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and diethylene glycol monoethyl ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol diacetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.Specific examples of glycol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, diethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-tert-butyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, and dipropylene glycol monomethyl ether. glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butylene glycol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, diethylene glycol monoethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol dimethyl ether, dipropylene glycol dimethyl ether pentane, triethylene glycol dimethyl ether, polyethylene glycol dimethyl ether.Specific examples of alcohol-based organic solvents include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3-butanediol, 1,3-butanediol, 1,3-butylene glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4-methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isotridecanol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol, 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol.

[0084] Examples of the organic solvent include halogen-based organic solvents, nitrogen-containing compounds, sulfur-containing compounds, siloxane compounds, and fluorine-containing organic solvents.

[0085] Specific examples of halogen-based organic solvents include dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0086] Examples of the nitrogen-containing compound include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0087] Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0088] Examples of the siloxane compound include hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, and decamethyltetrasiloxane.

[0089] Examples of the fluorine-containing organic solvent include polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C ６ F １３ CH ２ CH ３ (e.g., Asahiklin (registered trademark) AC-6000 manufactured by AGC Corporation), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora (registered trademark) H manufactured by Zeon Corporation); hydrofluoroethers (HFEs) (e.g., perfluoropropyl methyl ether (C ３ F ７ OCH ３ ) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C ４ F ９ OCH ３ ) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C ４ F ９ O.C. ２ H ５ ) (e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C ２ F ５ CF (OCH ３ ) C ３ F ７ ) (e.g., Novec™ 7300 manufactured by Sumitomo 3M Limited) and other alkyl perfluoroalkyl ethers (the perfluoroalkyl group and the alkyl group may be linear or branched), and CF ３ CH ２ OCF ２ CHF ２(for example, Asahiklin (registered trademark) AE-3000 manufactured by AGC Corporation); hydrofluoroolefins (HFOs) (for example, 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (for example, Amorea (registered trademark) AS-300 manufactured by AGC Corporation)).

[0090] The content of the liquid medium is preferably 60 to 99.999 mass%, more preferably 80 to 99.99 mass%, and even more preferably 90 to 99.9 mass%, relative to the total amount of the composition of the present disclosure. In the case of a composition of the present disclosure used in a wet coating method, the content of the liquid medium may be 90 to 99.99 mass%, 95 to 99.98 mass%, 97 to 99.97 mass%, or 98 to 99.95 mass%, relative to the total amount of the composition of the present disclosure.

[0091] The composition of the present disclosure may contain other components in addition to the compound and liquid medium of the present disclosure, as long as the effects of the present disclosure are not impaired. Examples of other components include known additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reaction of reactive silyl groups.

[0092] The catalyst may be any appropriate acid or base, transition metal (e.g., Ti, Ni, Sn, Zr, Al, B), sulfur-containing compounds having an unshared electron pair in their molecular structure, nitrogen-containing compounds (e.g., sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphoric acid amide compounds, amide compounds, urea compounds), etc. Examples of acid catalysts include acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid. Examples of base catalysts include ammonia, sodium hydroxide, potassium hydroxide, and organic amines such as triethylamine and diethylamine.

[0093] Other components also include metal compounds having a hydrolyzable group (hereinafter, metal compounds having a hydrolyzable group are also referred to as "specific metal compounds"). When the composition of the present disclosure contains a specific metal compound, the slip properties and antifouling properties of the surface treatment layer can be further improved. Examples of the specific metal compounds include those represented by the following formulas (M1) to (M3).

[0094] M (X ｂ１ ) ｍ２１ (X ｂ２ ) ｍ２２ (X ｂ３ ) ｍ２３ ... (M1) Si (X ｂ４ ) (X ｂ５ ) ３ ... (M2) (X ｂ６ ) ３ Si-(Y ｂ１ )-Si(X ｂ７ ) ３ …(M3)

[0095] In formula (M1), M represents a trivalent or tetravalent metal atom. ｂ１ Each of X independently represents a hydrolyzable group. ｂ２ Each of X independently represents a siloxane skeleton-containing group. ｂ３ each independently represents a hydrocarbon chain-containing group, m21 is an integer of 2 to 4, m22 and m23 are each independently an integer of 0 to 2, when M is a trivalent metal atom, m21 + m22 + m23 is 3, and when M is a tetravalent metal atom, m21 + m22 + m23 is 4.

[0096] In formula (M2), X ｂ４ represents a hydrolyzable silane oligomer group. ｂ５ each independently represents a hydrolyzable group or an alkyl group having 1 to 4 carbon atoms.

[0097] In formula (M3), X ｂ６ and X ｂ７ each independently represents a hydrolyzable group or a hydroxyl group. ｂ１ represents a divalent organic group.

[0098] In formula (M1), the metal represented by M also includes semimetals such as Si and Ge. M is preferably a trivalent metal or a tetravalent metal, more preferably Al, Fe, In, Hf, Si, Ti, Sn, or Zr, still more preferably Al, Si, Ti, or Zr, and particularly preferably Si.

[0099] In formula (M1), X ｂ１Examples of the hydrolyzable group represented by the formula (1) include the same hydrolyzable groups as those represented by L in the formula (1).

[0100] X ｂ２ The siloxane skeleton-containing group represented by the formula (I) has a siloxane unit (—Si—O—) and may be linear or branched. Examples of the siloxane unit include a dialkylsilyloxy group, such as a dimethylsilyloxy group or a diethylsilyloxy group. The number of repeating siloxane units in the siloxane skeleton-containing group is 1 or more, preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3. The siloxane skeleton-containing group may contain a divalent hydrocarbon group as part of the siloxane skeleton. Specifically, some oxygen atoms in the siloxane skeleton may be replaced with a divalent hydrocarbon group. Examples of the divalent hydrocarbon group include alkylene groups such as methylene, ethylene, propylene, and butylene. A hydrolyzable group, a hydrocarbon group (preferably an alkyl group), or the like may be bonded to the terminal silicon atom of the siloxane skeleton-containing group. The number of elements in the siloxane skeleton-containing group is preferably 100 or less, more preferably 50 or less, and even more preferably 30 or less. The number of elements is preferably 10 or more. Examples of the siloxane skeleton-containing group include *-(O-Si(CH ３ ) ２ ) ｎ CH ３ In this case, n is an integer of 1 to 5, and * represents a bonding site with an adjacent atom.

[0101] X ｂ３ The hydrocarbon chain-containing group represented by the formula (I) may be a group consisting of only a hydrocarbon chain, or may be a group having an etheric oxygen atom between carbon atoms in the hydrocarbon chain. The hydrocarbon chain may be a straight chain or a branched chain, with a straight chain being preferred. The hydrocarbon chain may be a saturated hydrocarbon chain or an unsaturated hydrocarbon chain, with a saturated hydrocarbon chain being preferred. The number of carbon atoms in the hydrocarbon chain-containing group is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. The hydrocarbon chain-containing group is preferably an alkyl group, and more preferably a methyl group, an ethyl group, or a propyl group.

[0102] Preferably, m1 is 3 or 4.

[0103] The compound represented by formula (M1) is preferably a compound represented by the following formulas (M1-1) to (M1-5) in which M is Si, and more preferably a compound represented by formula (M1-1). Preferred compounds represented by formula (M1-1) are tetraethoxysilane, tetramethoxysilane, and triethoxymethylsilane.

[0104] Si(X ｂ１ ) ４ ... (M1-1) CH ３ -Si(X ｂ１ ) ３ 　 …(M1-2) C ２ H ５ -Si(X ｂ１ ) ３ ...(M1-3) n-C ３ H ７ -Si(X ｂ１ ) ３ ...(M1-4) (CH ３ ) ２ CH—Si(X ｂ１ ) ３ …(M1-5)

[0105] In formula (M2), X ｂ４ The number of silicon atoms contained in the hydrolyzable silane oligomer group represented by the formula (I) is preferably 3 or more, more preferably 5 or more, and even more preferably 7 or more. The number of silicon atoms is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less. The hydrolyzable silane oligomer group may have an alkoxy group bonded to a silicon atom. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, with a methoxy group and an ethoxy group being preferred. The hydrolyzable silane oligomer group may have one or more of these alkoxy groups, and preferably has one type. Examples of the hydrolyzable silane oligomer group include (C ２ H ５ O) ３ Si-(OSi(OC) ２ H ５ ) ２ ) ４ O- ＊Here, * represents a bonding site with an adjacent atom.

[0106] In formula (M2), X ｂ５ Examples of the hydrolyzable group represented by X include the same hydrolyzable group represented by L in the above formula (1), a cyano group, a hydrogen atom, and an allyl group, and an alkoxy group or an isocyanato group is preferred. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. ｂ５ As the group, a hydrolyzable group is preferred.

[0107] The compound represented by formula (M2) includes (H ５ C ２ O) ３ -Si-(OSi(OC) ２ H ５ ) ２ ) ４ O.C. ２ H ５ etc.

[0108] The compound represented by formula (M3) is a compound having reactive silyl groups at both ends of a divalent organic group, i.e., a bissilane. ｂ６ and X ｂ７ Examples of the hydrolyzable group represented by formula (M3) include an alkoxy group, an acyloxy group, a ketoxime group, an alkenyloxy group, an amino group, an aminoxy group, an amide group, an isocyanato group, and a halogen atom, and an alkoxy group and an isocyanato group are preferred. As the alkoxy group, an alkoxy group having 1 to 4 carbon atoms is preferred, and a methoxy group and an ethoxy group are more preferred. In formula (M3), X ｂ６ and X ｂ７ may be the same group or different groups. ｂ６ and X ｂ７ are preferably the same group.

[0109] In formula (M3), Y ｂ１ is a divalent organic group that connects the reactive silyl groups at both ends. ｂ１ The number of carbon atoms in Y is preferably 1 to 8, and more preferably 1 to 3. ｂ１Examples of the alkylene group include an alkylene group, a phenylene group, and an alkylene group having an etheric oxygen atom between carbon atoms. ２ CH ２ -, -CH ２ CH ２ CH ２ -, -CH ２ CH ２ CH ２ CH ２ -, -CH ２ CH ２ CH ２ CH ２ CH ２ -, -CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ -, -CH ２ C(CH ３ ) ２ CH ２ -, -C(CH ３ ) ２ CH ２ CH ２ C(CH ３ ) ２ -, -CH ２ CH ２ OCH ２ CH ２ -, -CH ２ CH ２ CH ２ OCH ２ CH ２ CH ２ -, -CH(CH ３ ) CH ２ OCH ２ CH (CH ３ ) -, -C ６ H ４ - are listed.

[0110] The compound represented by formula (M3) includes (CH ３ O) ３ Si(CH ２ ) ２ Si(OCH ３ ) ３ , (C ２ H ５ O) ３ Si(CH ２) ２ Si(OC ２ H ５ ) ３ , (OCN) ３ Si(CH ２ ) ２ Si(NCO) ３ , Cl ３ Si(CH ２ ) ２ SiCl ３ , (CH ３ O) ３ Si(CH ２ ) ６ Si(OCH ３ ) ３ , (C ２ H ５ O) ３ Si(CH ２ ) ６ Si(OC ２ H ５ ) ３ Examples include:

[0111] The content of other components that may be included in the composition of the present disclosure is preferably 10% by mass or less, and more preferably 1% by mass or less, relative to the total amount of the composition of the present disclosure. When the composition of the present disclosure contains a specific metal compound, the content of the specific metal compound is preferably 0.01 to 30% by mass, more preferably 0.01 to 10% by mass, and even more preferably 0.05 to 5% by mass, relative to the total amount of the composition of the present disclosure.

[0112] The total content of the compound of the present disclosure and other components (hereinafter also referred to as "solid content concentration") is preferably 0.001 to 40 mass%, more preferably 0.01 to 20 mass%, and even more preferably 0.1 to 10 mass%, relative to the total amount of the composition of the present disclosure. The solid content concentration of the composition of the present disclosure is a value calculated from the mass of the composition before heating and the mass after heating for 4 hours in a convection dryer at 120°C.

[0113] The composition of the present disclosure contains a liquid medium, and is therefore useful for coating applications and can be used as a coating liquid.

[0114] In addition to compound (1) and / or compound (2) and the liquid medium, other components may be contained in addition to compound (1), compound (2), and the liquid medium, as long as the effects of the present disclosure are not impaired. Examples of other components include known additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reaction of hydrolyzable silyl groups. The content of other components in the surface treatment agent is preferably 10% by mass or less, more preferably 1% by mass or less.

[0115] Other components include compounds represented by the following formulas (10-1) and (10-2): [Y １ ３ Y ２ -Y ３ ] ｓ２ Y ４ (Si(Y ５ ) ｓ３ (Y ６ ) ３－ｓ３ ) ｓ４ ...(10-1) [Y １ ３ Y ２ -(O) ｓ１ -Y ３ ] ｓ２ Y ４ (Si(Y ５ ) ｓ３ (Y ６ ) ３－ｓ３ ) ｓ５ ...(10-2) In formula 1, Y １ are each independently a hydrocarbon group or a trialkylsilyloxy group; Y ２ is Si, Sn, or Ge, s1 is 0 or 1, and Y ３ are each independently an alkylene chain or a polyalkylene oxide chain, or a combination of an alkylene chain and a divalent polysiloxane residue; Y ４ represents a single bond or an s2+s4 valent linking group, ５ are each independently a hydrocarbon group; ６ are each independently a hydrolyzable group or a hydroxyl group; s3 is each independently an integer of 0 to 2; s2 and s4 are each independently an integer of 1 or more; and s5 is each independently an integer of 2 or more.

[0116] The compound (10-1) is Y ３ is an alkylene chain or a polyalkylene oxide chain. Specific examples of the compound (10-1) include the following compounds.

[0117] The compound (10-2) is Y ３ is an alkylene chain or a polyalkylene oxide chain. Specific examples of compound (10-2) include the following compounds. In the formula, α is preferably 9 to 50, more preferably 11 to 30, and particularly preferably 11 to 25.

[0118] When the other components in the present surface treatment agent are compound (10-1) and / or compound (10-2), the total content of compound (10-1) and compound (10-2) is preferably 50 mass% or less, more preferably 40 mass% or less.

[0119] [Surface Treatment Agent] In one embodiment, the surface treatment agent of the present disclosure contains the compound of the present disclosure. The surface treatment agent of the present disclosure may also contain the compound of the present disclosure and a liquid medium. The surface treatment agent of the present disclosure may also be the composition of the present disclosure. Preferred embodiments of the liquid medium contained in the surface treatment agent are the same as the preferred embodiments of the liquid medium contained in the composition of the present disclosure. The surface treatment agent of the present disclosure may contain at least one of the compound represented by formula (1) and the compound represented by formula (2). Note that the surface treatment agent of the present disclosure may also contain both the compound represented by formula (1) and the compound represented by formula (2).

[0120] The compound of the present disclosure contains an alkylene group having 7 to 100 carbon atoms, an organopolysiloxane group, and a reactive silyl group. Therefore, by using a surface treatment agent containing the compound of the present disclosure, it is possible to form a surface treatment layer that has excellent water repellency and abrasion resistance.

[0121] The surface treatment agent of the present disclosure is particularly preferably used for optical members.

[0122] [Article] In one embodiment, the article of the present disclosure includes a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent of the present disclosure.

[0123] The surface treatment layer may be formed on a part of the surface of the substrate, or may be formed on the entire surface of the substrate. The surface treatment layer may be spread in the form of a film on the surface of the substrate, or may be scattered in the form of dots. In the surface treatment layer, the compound of the present disclosure is contained in a state in which hydrolysis of some or all of the reactive silyl groups has progressed and dehydration condensation reaction of the silanol groups has progressed.

[0124] The thickness of the surface treatment layer is preferably 1 to 100 nm, more preferably 1 to 50 nm. If the thickness of the surface treatment layer is 1 nm or more, the effect of the surface treatment is likely to be sufficient. If the thickness of the surface treatment layer is 100 nm or less, the utilization efficiency is high. The thickness of the surface treatment layer can be calculated from the oscillation period of the interference pattern obtained by X-ray reflectivity using a thin film analysis X-ray diffractometer (product name "ATX-G", manufactured by RIGAKU Corporation).

[0125] The type of substrate is not particularly limited, and examples thereof include substrates that are required to be water-repellent. Examples of substrates include substrates that may be used by contacting other articles (e.g., stylus) or human fingers; substrates that may be held by human fingers during operation; and substrates that may be placed on other articles (e.g., a mounting table). Examples of substrate materials include metal, resin, glass, sapphire, ceramic, semiconductor, stone, fiber, nonwoven fabric, paper, wood, fur, natural leather, artificial leather, ceramics, and composite materials thereof. Glass may be chemically strengthened.

[0126] Examples of the substrate include glass or resin used for building materials, decorative building materials, interior goods, transportation equipment (e.g., automobiles), signs, bulletin boards, drinking vessels, tableware, aquariums, ornamental equipment (e.g., frames, boxes), laboratory equipment, furniture, textile products, packaging containers, art, sports, games, etc., and glass or resin used for the exterior parts (excluding display parts) of devices such as mobile phones (e.g., smartphones), personal digital assistants, game consoles, remote controls, etc. The shape of the substrate may be a plate or a film.

[0127] The substrate is preferably a substrate for a touch panel, a substrate for a display, or a lens for glasses, and is particularly preferably a substrate for a touch panel.The material of the substrate for a touch panel is preferably glass or a transparent resin.

[0128] The substrate may be a substrate whose one or both surfaces have been subjected to a surface treatment such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment. A surface-treated substrate has better adhesion to the surface treatment layer and further improved abrasion resistance of the surface treatment layer. Therefore, it is preferable to perform the surface treatment on the surface of the substrate that comes into contact with the surface treatment layer. Furthermore, when a base layer described below is provided on the surface-treated substrate, it has better adhesion to the base layer and further improved abrasion resistance of the surface treatment layer. Therefore, when a base layer is provided, it is preferable to perform the surface treatment on the surface of the substrate that comes into contact with the base layer.

[0129] The surface treatment layer may be provided directly on the surface of the substrate, or a primer layer may be provided between the substrate and the surface treatment layer. From the viewpoint of further improving the water repellency and abrasion resistance of the surface treatment layer, the article of the present disclosure preferably includes a substrate, a primer layer disposed on the substrate, and a surface treatment layer surface-treated with the surface treatment agent of the present disclosure, disposed on the primer layer.

[0130] The underlayer is preferably a layer containing an oxide containing silicon and at least one specific element selected from the group consisting of Group 1 elements, Group 2 elements, Group 4 elements, Group 5 elements, Group 13 elements, and Group 15 elements of the periodic table.

[0131] The Group 1 elements of the periodic table (hereinafter also referred to as "Group 1 elements") refer to lithium, sodium, potassium, rubidium, and cesium. As the Group 1 elements, lithium, sodium, and potassium are preferred, and sodium and potassium are more preferred, from the viewpoint of enabling a surface treatment layer to be formed more uniformly on the underlayer without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples. The underlayer may contain two or more types of Group 1 elements.

[0132] The Group 2 elements of the periodic table (hereinafter also referred to as "Group 2 elements") refer to beryllium, magnesium, calcium, strontium, and barium. As the Group 2 elements, magnesium, calcium, and barium are preferred, and magnesium and calcium are more preferred, from the viewpoint of enabling a surface treatment layer to be formed more uniformly on the underlayer without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples. The underlayer may contain two or more Group 2 elements.

[0133] The Group 4 elements of the periodic table (hereinafter also referred to as "Group 4 elements") refer to titanium, zirconium, and hafnium. As the Group 4 elements, titanium and zirconium are preferred, and titanium is more preferred, from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples. The underlayer may contain two or more types of Group 4 elements.

[0134] The Group 5 elements of the periodic table (hereinafter also referred to as "Group 5 elements") refer to vanadium, niobium, and tantalum. As the Group 5 element, vanadium is particularly preferred from the viewpoint of providing a surface treatment layer with better abrasion resistance. The underlayer may contain two or more Group 5 elements.

[0135] The Group 13 elements of the periodic table (hereinafter also referred to as "Group 13 elements") refer to boron, aluminum, gallium, and indium. As the Group 13 elements, boron, aluminum, and gallium are preferred, and boron and aluminum are more preferred, from the viewpoint of enabling the surface treatment layer to be formed more uniformly on the underlayer without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples. The underlayer may contain two or more Group 13 elements.

[0136] The Group 15 elements of the periodic table (hereinafter also referred to as "Group 15 elements") refer to nitrogen, phosphorus, arsenic, antimony, and bismuth. As the Group 15 elements, phosphorus, antimony, and bismuth are preferred, and phosphorus and bismuth are more preferred, from the viewpoint of enabling a surface treatment layer to be formed more uniformly on the underlayer without defects, or from the viewpoint of further suppressing variation in the composition of the underlayer between samples. The underlayer may contain two or more Group 15 elements.

[0137] As the specific element contained in the underlayer, Group 1 elements, Group 2 elements, and Group 13 elements are preferred because they provide better abrasion resistance to the surface treatment layer, and Group 1 elements and Group 2 elements are more preferred, with Group 1 elements being even more preferred. The specific element may contain only one type of element or two or more types of elements.

[0138] The oxide contained in the underlayer may be a mixture of oxides of the above elements (silicon and the specific element) alone (for example, a mixture of silicon oxide and an oxide of the specific element), a composite oxide containing two or more of the above elements, or a mixture of an oxide of the above elements alone and a composite oxide.

[0139] From the viewpoint of achieving superior abrasion resistance of the surface treatment layer, the ratio of the total molar concentration of the specific elements in the underlayer to the molar concentration of silicon in the underlayer (specific elements / silicon) is preferably 0.02 to 2.90, more preferably 0.10 to 2.00, and even more preferably 0.20 to 1.80. The molar concentrations (mol %) of each element in the underlayer can be measured, for example, by depth profile analysis by X-ray photoelectron spectroscopy (XPS) using ion sputtering.

[0140] The underlayer may be a single layer or multiple layers. The underlayer may have an uneven surface. The thickness of the underlayer is preferably 1 to 100 nm, more preferably 1 to 50 nm, and even more preferably 2 to 20 nm. When the thickness of the underlayer is equal to or greater than the above lower limit, the adhesion of the underlayer to the surface treatment layer is further improved, and the surface treatment layer has better abrasion resistance. When the thickness of the underlayer is equal to or less than the above upper limit, the underlayer itself has excellent abrasion resistance. The thickness of the underlayer is measured by observing the cross section of the underlayer using a transmission electron microscope (TEM).

[0141] The underlayer can be formed by, for example, a vapor deposition method using a vapor deposition material or a wet coating method.

[0142] The deposition material used in the deposition method preferably contains an oxide containing silicon and a specific element. Specific examples of the form of the deposition material include powder, melt, sintered body, granules, and crushed body, with melt, sintered body, and granules being preferred from the viewpoint of ease of handling. Here, the melt refers to a solid obtained by melting the powder of the deposition material at a high temperature and then cooling and solidifying it. The sintered body refers to a solid obtained by firing the powder of the deposition material. If necessary, a molded body may be used by press-molding the powder instead of the powder of the deposition material. The granule refers to a solid obtained by kneading the powder of the deposition material with a liquid medium (e.g., water, organic solvent) to obtain particles, and then drying the particles.

[0143] The vapor deposition material can be produced by, for example, the following methods: A method of mixing silicon oxide powder with a powder of an oxide of a specific element to obtain a vapor deposition material powder. A method of kneading the vapor deposition material powder with water to obtain particles, and then drying the particles to obtain granules of the vapor deposition material. A method of mixing a powder containing silicon (e.g., silicon oxide powder, silica sand, silica gel), a powder containing a specific element (e.g., oxide powder, carbonate, sulfate, nitrate, oxalate, hydroxide of the specific element), and water, drying the mixture, and then firing the dried mixture or a compact obtained by pressing the dried mixture to obtain a sintered body. A method of melting a powder containing silicon (e.g., silicon oxide powder, silica sand, silica gel) and a powder containing a specific element (e.g., oxide powder, carbonate, sulfate, nitrate, oxalate, hydroxide of the specific element) at a high temperature, and then cooling and solidifying the melt to obtain a melt.

[0144] A specific example of a vapor deposition method using a vapor deposition material is a vacuum vapor deposition method. The vacuum vapor deposition method is a method in which a vapor deposition material is evaporated in a vacuum chamber and attached to the surface of a substrate. The temperature during vapor deposition (for example, the temperature of the boat in which the vapor deposition material is placed when a vacuum vapor deposition apparatus is used) is preferably 100 to 3,000°C, and more preferably 500 to 3,000°C. The pressure during vapor deposition (for example, the pressure in the chamber in which the vapor deposition material is placed when a vacuum vapor deposition apparatus is used) is preferably 1 Pa or less, and more preferably 0.1 Pa or less. When forming an underlayer using a vapor deposition material, one vapor deposition material may be used, or two or more vapor deposition materials containing different elements may be used.

[0145] Specific examples of evaporation methods for the deposition material include a resistance heating method, in which the deposition material is melted and evaporated on a resistance heating boat made of a high-melting-point metal, and an electron gun method, in which the deposition material is irradiated with an electron beam to directly heat the deposition material, melting and evaporating the surface. The electron gun method is preferred as an evaporation method for the deposition material because it can evaporate high-melting-point substances due to its ability to locally heat the material, and because areas not irradiated by the electron beam are at low temperatures, eliminating the risk of reaction with the container or the inclusion of impurities. The evaporation method for the deposition material may use multiple boats, or all of the deposition materials may be placed in a single boat. The deposition method may be co-evaporation or alternating deposition. Specific examples include mixing silica and a specific source in the same boat, co-evaporating silica and a specific element source in separate boats, or similarly placing them in separate boats and alternately depositing them. The deposition conditions, order, etc., are appropriately selected depending on the composition of the underlayer.

[0146] In the wet coating method, it is preferable to form an undercoat layer on a substrate by a wet coating method using a coating liquid containing a silicon-containing compound, a compound containing a specific element, and a liquid medium.

[0147] Specific examples of the silicon compound include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partial hydrolysis condensates of alkoxysilanes.

[0148] Specific examples of compounds containing a specific element include oxides of the specific element, alkoxides of the specific element, carbonates of the specific element, sulfates of the specific element, nitrates of the specific element, oxalates of the specific element, and hydroxides of the specific element.

[0149] Examples of the liquid medium include the same liquid medium as that contained in the composition of the present disclosure.

[0150] The content of the liquid medium is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, based on the total amount of the coating liquid used to form the underlayer.

[0151] Specific examples of wet coating methods for forming the underlayer include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, Langmuir-Blodgett coating, and gravure coating.

[0152] After wet-coating the coating liquid, it is preferable to dry the coating film. The drying temperature for the coating film is preferably 20 to 200°C, more preferably 80 to 160°C.

[0153] The article of the present disclosure may be an optical material having a surface treatment layer as the outermost layer. Examples of the optical material include optical materials related to displays and the like, as well as a wide variety of other optical materials. Examples of the optical material include displays such as cathode ray tubes (CRTs; for example, personal computer monitors), liquid crystal displays, plasma displays, organic electroluminescent displays, inorganic thin-film electroluminescent dot matrix displays, rear projection displays, fluorescent display tubes (VFDs), and field emission displays (FEDs), as well as protective plates for such displays, or displays whose surfaces have been treated with an anti-reflection film.

[0154] The article of the present disclosure is preferably an optical component. Examples of optical components include car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio systems, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment such as gastroscopes, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and anti-reflection films. Examples of optical components include front protective plates, anti-reflection plates, polarizing plates, and anti-glare plates for displays such as PDPs and LCDs; disc surfaces of optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MO discs; optical fibers; and the display surfaces of watches. In particular, the article of the present disclosure is preferably a display or a touch panel.

[0155] The article of the present disclosure may be a medical device or a medical material. The article of the present disclosure may also be an automobile interior or exterior component. Examples of exterior components include windows, light covers, and exterior camera covers. Examples of interior components include instrument panel covers, navigation system touch panels, and decorative interior components.

[0156] When the article of the present disclosure is an optical component, the material constituting the surface of the substrate is a material for optical components, such as glass or transparent plastic. When the article of the present disclosure is an optical component, a functional layer such as a hard coat layer or an anti-reflection layer may be formed on the surface (outermost layer) of the substrate. The anti-reflection layer may be either a single-layer anti-reflection layer or a multi-layer anti-reflection layer. Examples of inorganic materials that can be used for the anti-reflection layer include SiO ２ , SiO, ZrO ２ , TiO ２ , TiO, Ti ２ O ３ , Ti ２ O ５ , Al ２ O ３ , Ta ２ O ５ , Ta ３ O ５, Nb ２ O ５ , HfO ２ , Si ３ N ４ , CeO ２ , MgO, Y ２ O ３ , SnO ２ , MgF ２ , and W.O. ３ These inorganic substances may be used alone or in combination of two or more (for example, as a mixture). When a multi-layer antireflection layer is formed, the outermost layer may contain SiO ２ and / or SiO is preferably used. When the article of the present disclosure is an optical glass component for a touch panel, a transparent electrode, for example, a thin film using indium tin oxide (ITO) or indium zinc oxide, may be provided on a portion of the surface of the substrate (glass). Furthermore, the substrate may have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomization film layer, a hard coating film layer, a polarizing film, a phase difference film, a liquid crystal display module, or the like, depending on its specific specifications.

[0157] [Method for manufacturing an article] The method for manufacturing an article according to the present disclosure is, for example, a method for manufacturing an article having a surface-treated layer formed on a substrate by performing a surface treatment on a substrate using the surface treatment agent according to the present disclosure. Examples of the surface treatment include a dry coating method and a wet coating method.

[0158] Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferred as a dry coating method from the viewpoints of suppressing decomposition of the compound and simplicity of the equipment. For vacuum deposition, a pellet-shaped substance obtained by impregnating a metal porous body such as iron or steel with the compound of the present disclosure may be used. A composition containing the compound of the present disclosure and a liquid medium may be impregnated into a metal porous body such as iron or steel, and the liquid medium may be dried to obtain a pellet-shaped substance impregnated with the compound of the present disclosure.

[0159] Examples of wet coating methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, Langmuir-Blodgett coating, and gravure coating.

[0160] In order to improve the abrasion resistance of the surface treatment layer, an operation to promote the reaction between the compound of the present disclosure and the substrate may be performed as necessary. Examples of such operations include heating, humidification, and light irradiation. Heating the substrate on which the surface treatment layer has been formed in a humid atmosphere can promote reactions such as the hydrolysis reaction of hydrolyzable groups, the reaction between hydroxyl groups on the surface of the substrate and silanol groups, and the formation of siloxane bonds through condensation reactions of silanol groups. After surface treatment, compounds in the surface treatment layer that are not chemically bonded to other compounds or the substrate may be removed as needed. Examples of removal methods include pouring a solvent over the surface treatment layer and wiping with a cloth soaked in the solvent.

[0161] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. Examples 1 to 14 are working examples, and Examples 15 and 16 are comparative examples.

[0162] [Synthesis of Compound 1-1] THF (tetrahydrofuran, 101 g) was added to hexamethylcyclotrisiloxane (65 g) and stirred at 25°C until dissolved. Next, a solution of lithium trimethylsilanol salt (5.1 g) suspended in THF (20 g) was added, and the mixture was stirred at 25°C for 2 hours. Next, chlorodimethylsilane (10.5 g) was added, and the mixture was stirred at 25°C for 1 hour. After extraction with hexane and water, the solvent and low-boiling components were distilled off under reduced pressure, and flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 25 g of Compound 1-1. In Compound 1-1, the average value of n was 13. The structure of Compound 1-1 was confirmed by the following NMR data.

[0163]

[0164] 1 ​H-NMR (400 MHz, CDCl3) δ: 4.63(hept, J = 2.8 Hz, 1H), 0.21 - 0.08(m, 6H), 0.07- 0.12(m, 87H).

[0165] [Synthesis of Compound 1-2] Dichloromethane (20 g) and 9-bromo-1-nonene (1.0 g) were added to Compound 1-1 (2.0 g) and stirred at 25°C until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg) was added and stirred at 25°C for 2 hours. Next, low-boiling point components were distilled off under reduced pressure, and then flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.6 g of Compound 1-2. In Compound 1-2, the average value of n was 13. The structure of Compound 1-2 was confirmed by the following NMR data.

[0166]

[0167] 1 H-NMR (400 MHz, CDCl3) δ: 3.41 (td, J = 6.9, 1.9 Hz, 2H), 1.99 - 1.76(m, 2H), 1.49 - 1.09 (m, 12H), 0.61 - 0.42 (m, 2H), 0.33 - 0.24 (m, 93H).

[0168] [Synthesis of Compound 1-3] THF (20 g), an allyl magnesium chloride solution (2.0 M in THF) (20 mL), and copper(II) chloride (0.02 g) were added to compound 1-2 (1.6 g), and the mixture was stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were distilled off under reduced pressure. Flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was then performed to obtain 1.3 g of compound 1-3. In compound 1-3, the average value of n was 13. The structure of compound 1-3 was confirmed by the following NMR data.

[0169]

[0170] 1 ​​H-NMR (400 MHz, CDCl3) δ: 5.95 - 5.59 (m, 1H), 5.12 - 4.75 (m, 2H), 2.13 - 1.89 (m, 2H), 1.64 - 0.84 (m, 16H), 0.67 - 0.36 (m, 2H), 0.30 - 0.41 (m, 93H).

[0171] [Synthesis of Compound 1-4] Dichloromethane (10 g) was added to compound 1-3 (1.3 g) to dissolve it. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 1.4 g of compound 1-4. In compound 1-4, the average value of n was 13. The structure of compound 1-4 was confirmed by the following NMR data.

[0172]

[0173] 1 H-NMR (400 MHz, CDCl3) δ: 3.57(s, 9H), 1.98 - 0.95 (m, 21H), 0.72 - 0.61 (m, 2H), 0.52 (t, J = 7.7 Hz, 2H),0.26 - 0.22 (m, 93H).

[0174] [Synthesis of Compound 2-1] Dichloromethane (20 g) and 18-bromo-1-octadecene (1.0 g) were added to Compound 1-1 (2.0 g) and stirred at 25°C until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added and stirred at 25°C for 2 hours. After distilling off low-boiling components under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.2 g of Compound 2-1. In Compound 2-1, the average value of n was 13. The structure of Compound 2-1 was confirmed by the following NMR data.

[0175]

[0176] ​1 H-NMR (400 MHz, CDCl3) δ: 3.41(t, J = 6.9 Hz, 2H), 1.85(p, J = 7.1 Hz, 2H), 1.75 -0.95 (m, 30H), 0.53 (s, 2H), 0.34 - 0.25 (m, 93H).

[0177] [Synthesis of Compound 2-2] THF (20 g), an allyl magnesium chloride solution (2.0 M in THF) (20 mL), and copper(II) chloride (0.02 g) were added to compound 2-1 (1.2 g), and the mixture was stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were distilled off under reduced pressure. Flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was then performed to obtain 1.1 g of compound 2-2. In compound 2-2, the average value of n was 13. The structure of compound 2-2 was confirmed by the following NMR data.

[0178]

[0179] 1 H-NMR (400 MHz, CDCl3) δ: 5.74 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.01 - 4.74 (m, 2H), 2.08 - 1.84 (m, 2H), 1.75 - 0.95 (m, 34H), 0.45 (dd, J = 9.4, 5.7 Hz, 2H) 0.34 - 0.25 (m, 93H).

[0180] [Synthesis of Compound 2-3] Dichloromethane (10 g) was added to compound 2-2 (1.1 g) to dissolve it. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 1.1 g of compound 2-3. In compound 2-3, the average value of n was 13. The structure of compound 2-3 was confirmed by the following NMR data.

[0181] ​​

[0182] 1 H-NMR (400 MHz, CDCl3) δ: 3.50 (s, 9H), 1.75 - 0.95 (m, 38H), 0.62 - 0.54 (m, 2H), 0.45 (dd, J = 9.4, 5.9 Hz, 2H), 0.34 - 0.25 (m, 93H).

[0183] [Synthesis of Compound 3-1] Dichloromethane (100 g) and trichloroisocyanuric acid (14 g) were added to 1,1,1,3,5,5,5-heptamethyltrisiloxane (10 g), and the mixture was stirred at 25°C for 3 hours. Next, the reaction solution was filtered to remove insoluble matter, and the filtrate was then distilled off to remove low-boiling components. Water (20 g), THF (40 g), and triethylamine (10 g) were added to the resulting crude liquid, and the mixture was stirred at 25°C for 2 hours. Hexane and water were added for extraction, and the low-boiling components were removed by distillation. The resulting crude liquid was purified by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate), yielding 8.3 g of Compound 3-1. The structure of Compound 3-1 was confirmed by the following NMR data.

[0184]

[0185] 1 H-NMR (400 MHz, CDCl3) δ: 2.41 (q, J = 7.2 Hz, 1H), 0.20 - 0.21 (m, 21H).

[0186] ​​[Synthesis of Compound 3-2] THF (20 g) was added to compound 3-1 (2.0 g) and the mixture was cooled to 0°C. A methyllithium solution (3.1 M in diethoxymethane) (2.7 mL) was then added and stirred at 25°C for 10 minutes. A solution of hexamethylcyclotrisiloxane (5.6 g) dissolved in THF (20 g) was then added and stirred at 25°C for 4 hours. Chlorodimethylsilane (2.0 g) was then added and stirred at 25°C for 1 hour. Hexane and water were added for extraction, and low-boiling components were removed by distillation. The resulting crude liquid was purified by flash column chromatography using silica gel (developing solvent: hexane / dichloromethane), yielding 4.3 g of compound 3-2. The average value of n in compound 3-2 was 9. The structure of compound 3-2 was confirmed by the following NMR data.

[0187]

[0188] 1 H-NMR (400 MHz, CDCl3) δ: 4.63 (p, J = 2.8 Hz, 1H), 0.11 (d, J = 2.8Hz, 6H), 0.09 - 0.12 (m, 75H).

[0189] [Synthesis of Compound 3-3] Dichloromethane (20 g) and 18-bromo-1-octadecene (0.75 g) were added to compound 3-2 (2.3 g) and stirred until homogenous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg) was added and stirred at 25°C for 2 hours. After distilling off low-boiling components under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.8 g of compound 3-3. In compound 3-3, the average value of n was 9. The structure of compound 3-3 was confirmed by the following NMR data.

[0190]

[0191] 1 ​​H-NMR (400 MHz, CDCl3) δ: 3.33 (t, J = 6.9 Hz, 2H), 1.78 (dt, J = 14.5, 7.0 Hz, 2H), 1.42 - 1.08 (m, 30H), 0.45 (t, J = 7.7 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0192] [Synthesis of Compound 3-4] To compound 3-3 (1.8 g), THF (20 g), an allyl magnesium chloride solution (2.0 M in THF) (20 mL), and copper(II) chloride (0.02 g) were added, and the mixture was stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. Then, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.5 g of compound 3-4. In compound 3-4, the average value of n was 9. The structure of compound 3-4 was confirmed by the following NMR data.

[0193]

[0194] 1 H-NMR (400 MHz, CDCl3) δ: 5.74 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.01 - 4.76 (m, 2H), 2.07 - 1.87 (m, 2H), 1.41 - 0.97 (m, 34H), 0.45 (dd, J = 9.5, 5.9 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0195] [Synthesis of Compound 3-5] Dichloromethane (10 g) was added to compound 3-4 (1.5 g) to dissolve it. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 1.6 g of compound 3-5. In compound 3-5, the average value of n was 9. The structure of compound 3-5 was confirmed by the following NMR data.

[0196] ​

[0197] 1 H-NMR (400 MHz, CDCl3) δ: 3.49 (s, 9H), 1.81 - 0.97 (m, 38H), 0.65 - 0.51 (m, 2H), 0.45 (dd, J = 9.8, 5.3 Hz, 2H) , 0.09 - 0.12 (m, 81H).

[0198] [Synthesis of Compound 4-1] THF (40 mL), undec-10-enyl magnesium bromide (24 mL) (0.50 M in THF), and copper(II) chloride (0.05 g) were added to 1,12-dibromododecane (13.5 g), and the mixture was heated and stirred at 50°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. Flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was then performed to obtain 3.8 g of compound 4-1. The structure of compound 4-1 was confirmed by the following NMR data.

[0199]

[0200] 1 H-NMR (400 MHz, CDCl3) δ: 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H), 5.18 - 4.87 (m, 2H), 3.42 (t, J = 4.7 Hz, 2H), 2.09 - 1.10 (m, 40H).

[0201] [Synthesis of Compound 4-2] Dichloromethane (20 g) and compound 4-1 (2.0 g) were added to compound 3-2 (2.0 g) and stirred at 25°C until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added, and the mixture was stirred at 25°C for 2 hours. After distilling off low-boiling components under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.6 g of compound 4-2. In compound 4-2, the average value of n was 9. The structure of compound 4-2 was confirmed by the following NMR data.

[0202] ​​

[0203] 1 H-NMR (400MHz, CDCl3) δ: 3.32 (t, J = 6.8 Hz, 2H), 1.76 (dt, J = 14.5, 7.0 Hz, 2H), 1.42 - 1.08 (m, 40H), 0.45 (t, J = 7.7Hz, 2H), 0.09 - 0.12 (m, 81H).

[0204] [Synthesis of Compound 4-3] To compound 4-2 (1.6 g), THF (20 g), an allyl magnesium chloride solution (2.0 M in THF) (20 mL), and copper(II) chloride (0.02 g) were added, and the mixture was stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were distilled off under reduced pressure. Then, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.3 g of compound 4-3. In compound 4-3, the average value of n was 9. The structure of compound 4-3 was confirmed by the following NMR data.

[0205]

[0206] 1 H-NMR (400 MHz, CDCl3) δ: 5.74 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.01 - 4.76 (m, 2H), 2.07 - 1.87 (m, 2H), 1.41 - 0.97 (m, 44H), 0.45 (dd, J = 9.5, 5.9 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0207] [Synthesis of Compound 4-4] Compound 4-3 (1.3 g) was dissolved in dichloromethane (10 g). Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure, yielding 1.3 g of compound 4-4. In compound 4-4, the average value of n was 9. The structure of compound 4-4 was confirmed by the following NMR data.

[0208] ​​

[0209] 1 H-NMR (400MHz, CDCl3) δ: 3.49 (s, 9H), 1.81 - 0.97 (m, 48H), 0.65 - 0.51 (m, 2H), 0.45 (dd, J = 9.8, 5.3 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0210] [Synthesis of Compound 5-1] THF (30 g) and magnesium (0.7 g) were added to 18-bromo-1-octadecene (10 g), and the mixture was heated to reflux at 50°C for 24 hours. The reaction solution was cooled, and the excess magnesium was removed by filtration. Next, compound 3-3 (1.0 g) and copper(II) chloride (0.02 g) were added, and the mixture was stirred at 50°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. Next, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed, yielding 0.8 g of compound 5-1. The average value of n in compound 5-1 was 9. The structure of compound 5-1 was confirmed by the following NMR data.

[0211]

[0212] 1 H-NMR (400 MHz, CDCl3) δ: 5.74 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.01 - 4.76 (m, 2H), 2.07 - 1.87 (m, 2H), 1.41 - 0.97 (m, 64H), 0.45 (dd, J = 9.5, 5.9 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0213] ​​[Synthesis of Compound 5-2] Dichloromethane (10 g) was added to compound 5-1 (0.8 g) to dissolve it. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 0.8 g of compound 5-2. In compound 5-2, the average value of n was 9. The structure of compound 5-2 was confirmed by the following NMR data.

[0214]

[0215] 1 H-NMR (400MHz, CDCl3) δ: 3.49 (s, 9H), 1.81 - 0.97 (m, 68H), 0.65 - 0.51 (m, 2H), 0.45 (dd, J = 9.8, 5.3 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0216] [Synthesis of Compound 6-1] Compound 6-1 was obtained according to the method described in JP 2017-119849 A.

[0217]

[0218] [Synthesis of Compound 6-2] THF (10 g) was added to compound 6-1 (2.2 g) and dissolved uniformly. The mixture was then cooled to 0°C, and a butyllithium solution (1.6 M in THF) (4.0 mL) was added, followed by stirring at 0°C for 15 minutes. Hexamethylcyclotrisiloxane (4.8 g) was then added, followed by stirring at 25°C for 12 hours. Subsequently, chlorodimethylsilane (1.5 g) was added, followed by stirring at 25°C for 1 hour. Hexane and water were added for extraction, and low-boiling components were removed by distillation. The resulting crude liquid was purified by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate), yielding 4.7 g of compound 6-2. The average value of n in compound 6-2 was 9. The structure of compound 6-2 was confirmed by the following NMR data.

[0219]

[0220] ​​1 H-NMR (400 MHz, CDCl3) δ: 4.68 - 4.52 (m, J = 2.9Hz, 1H), 0.15 - 0.06 (m, 6H), 0.05 - 0.06 (m, 81H).

[0221] [Synthesis of Compound 6-3] Dichloromethane (20 g) and 18-bromo-1-octadecene (1.1 g) were added to compound 6-2 (2.0 g) and stirred until homogenous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added and stirred at 25°C for 2 hours. After distilling off low-boiling components under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.8 g of compound 6-3. In compound 6-3, the average value of n was 9. The structure of compound 6-3 was confirmed by the following NMR data.

[0222]

[0223] 1 H-NMR (400 MHz, CDCl3) δ: 3.33 (t, J = 6.9 Hz, 2H), 1.78 (dt, J = 14.5, 7.0 Hz, 2H), 1.42 - 1.08 (m, 30H), 0.45 (t, J = 7.7 Hz, 2H), 0.09 - 0.12 (m, 87H).

[0224] [Synthesis of Compound 6-4] To compound 6-3 (1.8 g), THF (20 g), an allyl magnesium chloride solution (2.0 M in THF) (20 mL), and copper(II) chloride (0.02 g) were added, and the mixture was stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were distilled off under reduced pressure. Flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was then performed to obtain 1.4 g of compound 6-4. In compound 6-4, the average value of n was 9. The structure of compound 6-4 was confirmed by the following NMR data.

[0225]

[0226] ​​1 H-NMR (400 MHz, CDCl3) δ: 5.74 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.01 - 4.76 (m, 2H), 2.07 - 1.87 (m, 2H), 1.41 - 0.97 (m, 34H), 0.45 (dd, J = 9.5, 5.9 Hz, 2H), 0.09 - 0.12 (m, 87H).

[0227] [Synthesis of Compound 6-5] Dichloromethane (10 g) was added to compound 6-4 (1.4 g) to dissolve it. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 1.4 g of compound 6-5. In compound 6-5, the average value of n was 9. The structure of compound 6-5 was confirmed by the following NMR data.

[0228]

[0229] 1 H-NMR (400 MHz, CDCl3) δ: 3.49 (s, 9H), 1.81 - 0.97 (m, 38H), 0.65 - 0.51 (m, 2H), 0.45 (dd, J = 9.8, 5.3 Hz, 2H), 0.09 -0.12 (m, 87H).

[0230] ​[Synthesis of Compound 7-1] DMF (20 g) and sodium azide (2.0 g) were added to 18-bromo-1-octadecene (3.3 g), and the mixture was heated and stirred at 80°C for 24 hours. After extraction with hexane and water, the solvent and low-boiling components were removed by distillation under reduced pressure. THF (20 g) and a lithium aluminum hydride solution (2.0 M in THF) (10 mL) were added to the resulting crude liquid, and the mixture was stirred for 12 hours. The reaction was then quenched by slowly adding aqueous sodium hydroxide solution dropwise. After removing insoluble matter by filtration, the solvent and low-boiling components were removed by distillation under reduced pressure. Flash column chromatography using silica gel (developing solvent: methanol / dichloromethane) was performed to obtain 1.2 g of Compound 7-1. The structure of Compound 7-1 was confirmed by the following NMR data.

[0231]

[0232] 1 H-NMR (400 MHz, CDCl3) δ: 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H), 5.18 - 4.72 (m, 2H), 2.68 (tt, J = 6.5, 5.2 Hz, 2H), 2.18 - 0.92 (m, 28H).

[0233] [Synthesis of Compound 7-2] Under a nitrogen atmosphere, 2,3,4,5,6-pentafluorophenol (6.8 g), THF (42 mL), and triethylamine (5.1 g) were added to a 100 mL flask and stirred at 25°C. Next, 10-undecenoyl chloride (5.0 g) was added dropwise, and the mixture was stirred for 1 hour. The reaction solution was filtered, and the solvent and low-boiling components were distilled off under reduced pressure. 7.9 g of Compound 7-2 was obtained by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate). The structure of Compound 7-2 was confirmed by the following NMR data.

[0234]

[0235] 1 ​​H-NMR (400MHz, CDCl3) δ: 5.74 (ddt, J = 16.9, 10.2, 6.6 Hz, 1H), 5.05 - 4.77 (m, 2H), 2.59 (t, J = 7.4 Hz, 2H), 1.97 (q, J = 7.1 Hz, 2H), 1.70 (p, J = 7.4 Hz, 2H), 1.42 - 1.08 (m, 10H).

[0236] [Synthesis of Compound 7-3] Dichloromethane (20 g) and compound 7-2 (1.0 g) were added to compound 3-2 (2.0 g) and stirred until homogenous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added and stirred at 25°C for 2 hours. Next, compound 7-1 (3.0 g) and triethylamine (3.0 g) were added and stirred at 25°C for 16 hours. After distilling off low-boiling components under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 1.5 g of compound 7-3. In compound 7-3, the average value of n was 9. The structure of compound 7-3 was confirmed by the following NMR data.

[0237]

[0238] 1 H-NMR (400MHz, CDCl3) δ: 5.97 - 5.52 (m, 2H), 5.32 - 4.54 (m, 2H), 3.13 (q, J = 5.5 Hz, 2H), 2.29 - 1.09 (m, 48H), 0.58 (t, J = 8.5 Hz, 2H), 0.12 - 0.15 (m, 81H).

[0239] ​[Synthesis of Compound 7-4] Compound 7-3 (1.5 g) was dissolved in dichloromethane (10 g). Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure, yielding 1.5 g of compound 7-4. In compound 7-4, the average value of n was 9. The structure of compound 7-4 was confirmed by the following NMR data.

[0240]

[0241] 1 H-NMR (400MHz, CDCl3) δ: 5.85 (t, J = 4.9 Hz, 1H), 3.58 (s, 9H), 3.13 (q, J = 5.4 Hz, 2H), 2.32 - 1.04 (m, 50H), 0.83 - 0.42 (m, 4H), 0.12 - 0.15 (m, 81H).

[0242] [Synthesis of Compound 8-1] THF (20 g) was added to 4,4'-dibromobiphenyl (2.0 g), the mixture was dissolved uniformly, and the mixture was cooled to -40°C. A normal butyllithium solution (1.6 M in hexane) (3.6 mL) was added, and the mixture was stirred for 15 minutes. Next, 18-bromo-1-octadecene (1.1 g) was added, and the mixture was stirred at 25°C for 24 hours. After extraction with hydrochloric acid and hexane, the solvent and low-boiling components were distilled off. The resulting crude liquid was subjected to flash column chromatography using silver nitrate silica gel (developing solvent: hexane / dichloromethane), yielding 1.0 g of Compound 8-1. The structure of Compound 8-1 was confirmed by the following NMR data.

[0243]

[0244] 1 ​​H-NMR (400 MHz, CDCl3) δ: 7.84 - 7.11 (m, 8H), 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H), 5.18 - 4.71 (m, 2H), 2.60 (tt, J = 8.0, 1.0 Hz, 2H), 2.14 - 1.09 (m, 30H).

[0245] [Synthesis of Compound 8-2] THF (20 g) was added to compound 8-1 (1.0 g), which was then homogeneously dissolved and cooled to -40°C. Next, a normal butyllithium solution (1.6 M in hexane) (1.6 mL) was added, and the mixture was stirred at 25°C for 15 minutes. Next, hexamethylcyclotrisiloxane (1.5 g) was added, and the mixture was stirred at 25°C for 3 hours. Next, chlorotrimethylsilane (1.0 g) was added, and the mixture was stirred for 2 hours. After extraction with hexane and water, the solvent and low-boiling components were distilled off. The resulting crude liquid was subjected to flash column chromatography using silica gel (developing solvent: hexane / dichloromethane), yielding 1.1 g of compound 8-2. The average value of n in compound 8-2 was 9. The structure of compound 8-2 was confirmed by the following NMR data.

[0246]

[0247] 1 H-NMR (400 MHz, CDCl3) δ: 7.67 - 7.11 (m, 8H), 5.80 (ddt, J = 17.2, 10.3, 7.0 Hz, 1H), 5.21 - 4.66 (m, 2H), 2.60 (tt, J = 8.0, 1.0Hz, 2H), 2.13 - 0.99 (m, 30H), 0.34 (s, 6H), 0.12 - 0.15 (m, 63H).

[0248] ​[Synthesis of Compound 8-3] Dichloromethane (10 g) was added to compound 8-2 (1.1 g) to dissolve it. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 1.1 g of compound 8-3. In compound 8-3, the average value of n was 9. The structure of compound 8-3 was confirmed by the following NMR data.

[0249]

[0250] [Synthesis of Compound 9-1] Dichloromethane (10 g), 1,1,1,3,3-pentamethyldisiloxane (15 g), and a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 50 mg) were added to 18-bromo-1-octadecene (10 g), and the mixture was stirred at 25°C for 24 hours. After removing low-boiling point components by distillation under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 12 g of Compound 9-1. The structure of Compound 9-1 was confirmed by the following NMR data.

[0251]

[0252] 1 H-NMR (400 MHz, CDCl3) δ: 3.41 (t, J = 6.9 Hz, 2H), 1.85 (p, J = 7.0 Hz, 2H), 1.49 - 1.04 (m, 30H), 0.50 (t, J = 7.6 Hz, 2H), 0.25 - -0.19 (m, 15H)

[0253] ​[Synthesis of Compound 9-2] THF (10 g), allyl magnesium chloride (approximately 11% tetrahydrofuran solution, 1.0 M) (10 mL), and copper(II) chloride (0.05 g) were added to compound 9-1 (1 g), and the mixture was stirred at 60°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. After that, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 0.8 g of compound 9-2. The structure of compound 9-2 was confirmed by the following NMR data.

[0254]

[0255] 1 H-NMR (400 MHz, CDCl3) δ: 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H), 5.24 - 4.78 (m, 2H), 2.18 - 1.86 (m, 2H), 1.54 - 1.00 (m, 34H), 0.69 (t, J = 8.3 Hz, 2H), 0.25 - -0.19 (m, 15H)

[0256] [Synthesis of Compound 9-3] To a solution of compound 9-2 (0.6 g) in dichloromethane (10 g) was added a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 5 mg), aniline (3 mg), and trimethoxysilane (0.60 g), and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure, yielding 0.8 g of compound 9-3. The structure of compound 9-3 was confirmed by the following NMR data.

[0257]

[0258] 1 H-NMR (400 MHz, CDCl3) δ: 3.57 (s, 9H), 1.54 - 1.00 (m, 38H), 0.70 - 0.60 (m, 2H), 0.50 (dd, J = 9.2, 6.1 Hz, 2H), 0.25 - -0.19 (m, 15H)

[0259] ​​[Synthesis of Compound 10-1] THF (20 g) and magnesium (1.1 g) were added to 11-bromo-1-undecene (10 g) and the mixture was stirred at 60°C for 2 hours. The reaction solution was filtered to obtain 30 g of compound 10-1. The product was confirmed to have a concentration of 0.8 M by titration with 1,10-phenanthroline.

[0260]

[0261] [Synthesis of Compound 10-2] THF (10 g), compound 10-1 (0.8 M) (10 mL), and copper(II) chloride (0.05 g) were added to compound 9-1 (1 g), and the mixture was stirred at 60°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. 0.5 g of compound 10-2 was obtained by flash column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane). The structure of compound 10-2 was confirmed by the following NMR data.

[0262]

[0263] 1 H-NMR (400 MHz, CDCl3) δ: 5.81 (ddt, J = 16.9, 10.1, 6.7 Hz, 1H), 5.08 - 4.82 (m, 2H), 2.13 - 1.93 (m, 2H), 1.54 - 1.00 (m, 50H), 0.63 - 0.41 (m, 2H), 0.25 - -0.19 (m, 15H).

[0264] [Synthesis of Compound 10-3] To a solution of compound 10-2 (0.5 g) in dichloromethane (10 g), a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 5 mg), aniline (3 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure, yielding 0.6 g of compound 10-3. The structure of compound 10-3 was confirmed by the following NMR data.

[0265]

[0266] 1 ​​H-NMR (400 MHz, CDCl3) δ: 3.57 (s, 9H), 1.54 - 1.00 (m, 54H), 0.77 - 0.61 (m, 2H), 0.50 (t, J = 7.3 Hz, 2H), 0.25 - -0.19 (m, 15H).

[0267] [Synthesis of Compound 11-1] THF (40 g) and magnesium (0.9 g) were added to 18-bromo-1-octadecene (10 g) and the mixture was stirred at 60°C for 2 hours. The reaction solution was filtered to obtain 50 g of compound 11-1. The concentration of the product was confirmed to be 0.4 M by titration with 1,10-phenanthroline.

[0268]

[0269] [Synthesis of Compound 11-2] THF (10 g), compound 11-1 (0.4 M) (20 mL), and copper(II) chloride (0.05 g) were added to compound 10-1 (1 g), and the mixture was stirred at 60°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. Then, flash column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 0.4 g of compound 11-2. The structure of compound 11-2 was confirmed by the following NMR data.

[0270]

[0271] 1 H-NMR (400 MHz, CDCl3) δ: 5.81 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.22 - 4.68 (m, 2H), 2.21 - 1.85 (m, 2H), 1.54 - 1.00 (m, 64H), 0.50 (t, J = 7.1 Hz, 2H), 0.25 - -0.19 (m, 15H).

[0272] ​[Synthesis of Compound 11-3] To a solution of Compound 11-2 (0.4 g) in dichloromethane (10 g), a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 5 mg), aniline (3 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure, yielding 0.5 g of Compound 11-3. The structure of Compound 11-3 was confirmed by the following NMR data.

[0273]

[0274] 1 H-NMR (400 MHz, CDCl3) δ: 3.57 (s, 9H), 1.54 - 1.00 (m, 68H), 0.77 - 0.61 (m, 2H), 0.50 (t, J = 7.6 Hz, 2H), 0.25 - -0.19 (m, 15H).

[0275] [Synthesis of Compound 12-1] Dichloromethane (10 g), 1,1,1,3,3,5,5-heptamethyltrisiloxane (15 g), and a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 50 mg) were added to 18-bromo-1-octadecene (10 g), and the mixture was stirred at 25°C for 24 hours. After removing the low-boiling point components by distillation under reduced pressure, flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 14 g of Compound 12-1. The structure of Compound 12-1 was confirmed by the following NMR data.

[0276]

[0277] 1 H-NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.85 (dt, J = 14.5, 7.0 Hz, 2H), 1.54 - 1.00 (m, 30H), 0.53 (dd, J = 9.4, 5.9 Hz, 2H), 0.25 - -0.33 (m, 21H).

[0278] ​​[Synthesis of Compound 12-2] THF (10 g), compound 10-1 (0.8 M) (10 mL), and copper(II) chloride (0.05 g) were added to compound 12-1 (1 g), and the mixture was stirred at 60°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were distilled off under reduced pressure. Then, flash column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 0.4 g of compound 12-2. The structure of compound 12-2 was confirmed by the following NMR data.

[0279]

[0280] 1 H-NMR (400 MHz, CDCl3) δ 5.82 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.10 - 4.81 (m, 2H), 2.12 - 1.90 (m, 2H), 1.54 - 1.00 (m, 50H), 0.52 (t, J = 7.7 Hz, 2H), 0.25 - -0.33 (m, 21H).

[0281] [Synthesis of Compound 12-3] To a solution of compound 12-2 (0.4 g) in dichloromethane (10 g) was added a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3 mass%, 5 mg), aniline (3 mg), and trimethoxysilane (0.60 g), and the mixture was stirred at 50°C for 2 hours. The solvent was distilled off under reduced pressure to obtain 0.45 g of compound 12-3. The structure of compound 12-3 was confirmed by the following NMR data.

[0282]

[0283] 1 H-NMR (400 MHz, CDCl3) δ 3.48 (s, 9H), 1.54 - 1.00 (m, 54H), 0.63 - 0.49 (m, 2H), 0.44 (t, J = 7.7 Hz, 2H), 0.25 - -0.33 (m, 21H).

[0284] [Preparation of Composition 13] Compound 3-5 and compound 10-3 were mixed in a mass ratio of 90:10. ​

[0285] [Preparation of Composition 14] Compound 3-5 and compound 11-3 were mixed in a mass ratio of 90:10.

[0286] [Synthesis of Compound 15-1] Compound 15-1 was obtained according to the method described in WO 2023 / 017830. In the formula, "18" is an average value.

[0287]

[0288] [Preparation of Compound 16-1] Compound 16-1 (trade name: X-22-1968, manufactured by Shin-Etsu Chemical Co., Ltd.) was prepared.

[0289]

[0290] [Production of Articles] Substrates were surface-treated using Compound 1-4, Compound 2-3, Compound 3-5, Compound 4-4, Compound 5-2, Compound 6-5, Compound 7-4, Compound 8-3, Compound 9-3, Compound 10-3, Compound 11-3, Compound 12-3, Composition 13, Composition 14, Compound 15-1, and Compound 16-1 to obtain articles of Examples 1 to 16. The surface treatment method used for each example was the dry coating method described below. Chemically strengthened glass was used as the substrate. The obtained articles were evaluated by the following method. The results are shown in Table 1. 30 g of silicon oxide was placed as a deposition source in a copper hearth in a vacuum deposition apparatus ("VTR-350M" manufactured by ULVAC KIKO Co., Ltd.). A glass substrate was placed in the vacuum deposition apparatus, and the interior of the vacuum deposition apparatus was heated to 5 × 10 －３ The hearth was then evacuated to a pressure of 10 Pa or less. The hearth was heated to approximately 2,000°C, and silicon oxide was vacuum-deposited on the surface of the substrate, producing a substrate with a silicon oxide layer having a thickness of approximately 20 nm. This was carried out using a vacuum deposition apparatus (manufactured by ULVAC, product name: VTR350M) (vacuum deposition method). 0.5 g of each compound was loaded into a molybdenum boat in the vacuum deposition apparatus, and the interior of the vacuum deposition apparatus was heated to 1 x 10 －３The chamber was evacuated to a pressure of 10 Pa or less. The boat containing the compound was heated at a temperature increase rate of 10°C / min or less, and when the deposition rate measured by a quartz crystal oscillator film thickness meter exceeded 1 nm / sec, the shutter was opened to start film formation on the surface of the substrate. When the film thickness reached approximately 50 nm, the shutter was closed to terminate film formation on the surface of the substrate with a silicon oxide layer. The substrate on which the compound or composition had been deposited was heat-treated at 200°C for 30 minutes and washed with ethanol to obtain an article having a surface-treated layer on the surface of the substrate.

[0291] [Evaluation] <Water repellency> Approximately 2 μL of distilled water was dropped onto the surface treatment layer of the article, and the initial water contact angle was measured using a contact angle measuring device (product name "DM-500", manufactured by Kyowa Interface Science Co., Ltd.). The average value measured at five points on the surface treatment layer was taken as the water contact angle. The water repellency of the surface treatment layer was evaluated based on the following criteria. The 2θ method was used to calculate the water contact angle. The results are shown in Table 1. A: The initial water contact angle was 105° or more. B: The initial water contact angle was less than 105°.

[0292] <Oil repellency> Approximately 2 μL of n-hexadecane was dropped onto the surface treatment layer of the article, and the initial oil contact angle (n-hexadecane contact angle) was measured using a contact angle measuring device (product name "DM-500", manufactured by Kyowa Interface Science Co., Ltd.). The average value measured at five points on the surface treatment layer was taken as the oil contact angle. The oil repellency of the surface treatment layer was evaluated based on the following evaluation criteria. The 2θ method was used to calculate the oil contact angle. A: The initial oil contact angle was 38° or more. B: The initial oil contact angle was less than 38°.

[0293] <Abrasion Resistance> The surface treatment layer of the article was subjected to a friction test using a reciprocating traverse tester (manufactured by KNT Corporation) in accordance with JIS L0849:2013 (ISO 105-X12:2001), in which steel wool Bonstar (#0000) was reciprocated 10,000 times at a pressure of 98.07 kPa and a speed of 320 cm / min, and the water contact angle after the friction test was measured. The method for measuring the water contact angle after the friction test was the same as the method for measuring the initial water contact angle in the evaluation method for water repellency. Note that the smaller the decrease in water repellency (water contact angle) after the friction test, the smaller the decrease in performance due to friction, and the more excellent the abrasion resistance. The evaluation criteria are as follows. The results are shown in Table 1. Change in water contact angle = (initial water contact angle) - (water contact angle after friction test) A: The change in water contact angle was 2° or less. B: The change in water contact angle was more than 2° and less than 3°. C: The change in water contact angle was more than 3° and less than 5°. D: The change in water contact angle is more than 5°.

[0294] <Fingerprint Removability> A 1 kg weight equipped with a 2 cm diameter red rubber stopper to serve as the fingerprint stamp was prepared. Next, 70 μL of artificial fingerprint liquid (manufactured by Isekyu Co., Ltd.) was dropped onto a waste cloth, and the fingerprint stamp was left to adhere to the artificial fingerprint liquid for 1 minute. To remove excess artificial fingerprint liquid from the fingerprint stamp, the fingerprint stamp was left to adhere to a new waste cloth for 20 seconds. The article with the surface treatment layer formed was then placed on a hot plate adjusted to 23°C. The fingerprint stamp was stamped against the surface treatment layer. The article with the artificial fingerprint liquid attached was placed in a sliding device (product name "HHS-2000", manufactured by Shinto Scientific Co., Ltd.). A wiping cloth (Savina Minimax, manufactured by KB Seiren Co., Ltd.) was attached to a flat indenter with an area of ​​1 cm square using double-sided tape, and the article was then placed in the sliding device. The artificial fingerprint liquid attached to the surface treatment layer was wiped off in one direction with the wiping cloth under a load of 100 g. The haze of the wiped area was measured using a haze meter (product name "NDH7000SP", manufactured by Nippon Denshoku Co., Ltd.). The evaluation criteria were as follows. The results are shown in Table 1. A: Haze value less than 0.1%. B: Haze value 0.1% or more but less than 1%. C: Haze value 1% or more.

[0295] <Lightfastness> The surface treatment layer was subjected to a light fastness test using a desktop xenon arc lamp accelerated light fastness tester (SUNTEST XLS+: product name, manufactured by Toyo Seiki Seisakusho) at a black panel temperature of 63°C and a light intensity of 650 W / m ２ , 300 to 700 nm) for 500 hours, and then the water contact angle of the surface treatment layer was measured using the method described above. The smaller the decrease in water contact angle after the accelerated light resistance test, the smaller the decrease in performance due to light, and the more excellent the light resistance of the surface treatment layer. The evaluation criteria are as follows. The results are shown in Table 1. Change in water contact angle = (initial water contact angle) - (water contact angle after accelerated light resistance test) A: The change in water contact angle after the accelerated light resistance test was 3° or less. B: The change in water contact angle after the accelerated light resistance test was more than 3° and 5° or less. C: The change in water contact angle after the accelerated light resistance test was more than 5°.

[0296] <Acid resistance> The article was cut into a 1 cm x 1 cm square and immersed in an aqueous hydrochloric acid solution (0.1 M) at 20°C for 100 hours. The article was then removed, washed with ethanol, dried, and the water contact angle was measured. The smaller the decrease in water repellency (water contact angle) after immersion, the smaller the decrease in performance due to acid, and the more excellent the acid resistance. The evaluation criteria are as follows: A: The decrease in water contact angle after immersion is 3° or less. B: The decrease in water contact angle after immersion is more than 3° and not more than 5°. C: The decrease in water contact angle after immersion is more than 5° and not more than 10°. D: The decrease in water contact angle after immersion is more than 10°.

[0297]

[0298] As shown in Table 1, it was found that the articles of Examples 1 to 14, in which Compound 1-4, Compound 2-3, Compound 3-5, Compound 4-4, Compound 5-2, Compound 6-5, Compound 7-4, Compound 8-3, Compound 9-3, Compound 10-3, Compound 11-3, Compound 12-3, Composition 13, and Composition 14 represented by Formula (1) were used as surface treatment agents, were superior in abrasion resistance compared to the articles of Examples 15 and 16.

[0299] The compounds of the present disclosure are useful as surface treatment agents. The surface treatment agents can be used, for example, for display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automotive parts, and substrates used in nanoimprint technology. The surface treatment agents can also be used for the bodies, window glass (windshields, side glass, rear glass), mirrors, bumpers, and the like of transportation equipment such as trains, automobiles, ships, and aircraft. Furthermore, the surface treatment agents can be used for outdoor items such as building exterior walls, tents, solar power generation modules, soundproofing panels, and concrete; fishing nets, insect nets, and aquariums. The surface treatment agents can also be used for various indoor facilities such as kitchens, bathrooms, sinks, mirrors, and toilet peripherals; ceramics such as chandeliers and tiles; artificial marble, and air conditioners. The surface treatment agents can also be used for antifouling treatment of jigs, interior walls, piping, and the like in factories. The surface treatment agents can also be used for goggles, eyeglasses, helmets, pachinko machines, textiles, umbrellas, playground equipment, and soccer balls. The surface treatment agents can also be used as anti-adhesion agents for various packaging materials such as food packaging, cosmetic packaging, and the inside of pots. The surface treatment agent can also be used for optical components such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio equipment, game machines, eyeglass lenses, camera lenses, lens filters, sunglasses, medical devices such as gastroscopes, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and antireflection films.

[0300] This application claims priority based on Japanese Patent Application No. 2023-103355 filed on June 23, 2023, Japanese Patent Application No. 2023-150604 filed on September 15, 2023, and Japanese Patent Application No. 2024-60422 filed on April 3, 2024, the disclosures of which are incorporated herein in their entireties.

Claims

1. A compound represented by the following formula (1) or the following formula (2): [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ ... (1) L １ ３－ｎ (R ３ ) ｎ Si-Z １ -Q ２ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ … (2) where R １ Each independently represents １１ ) ３ Si-, a monovalent cyclic polysiloxane residue, or a monovalent cage-shaped polysiloxane residue; R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ each independently represents an oxygen atom or an alkylene group; R ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group; R ４ each independently represents a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ -, each p1 is independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, ２ each independently represents a single bond or a divalent linking group; １ each independently represents an alkylene group having 7 to 100 carbon atoms; １ each independently represents a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; and each n independently represents an integer of 0 to 2.

2. The above Z １ is an alkylene group having 21 to 60 carbon atoms.

3. The above Q ２ The compound according to claim 1, wherein Q is represented by the following formula (Q1): １０ ｒ１ -R ５ ｒ２ -Q １１ ｒ３ - ... (Q1) where Q １０ The side is connected to Si, and the Q １１ Side is Z １ and r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, and when r1, r2, and r3 are all 0, ２ is a single bond, and Q １０ is an oxygen atom or an alkylene group; R ５ is -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ - and R ６ are each independently a hydrocarbon group, p3 is a number from 0 to 100, and Q １１ is a carbon-carbon atom bond, R ５ Side end or Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ R is a hydrocarbon group optionally having a bond selected from -, -O-, and -S-; ａ１ are each independently a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group, provided that Z １ The alkylene group is not present at the terminal of the alkylene group.

4. A compound represented by the following formula (11): １ -Q １ -SiR ２ ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ … (11) where R １ (R １１ ) ３ Si-, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ is an oxygen atom or an alkylene group; R ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group; ２ each independently represents a single bond or a divalent linking group; １ each independently represents an alkylene group having 7 to 100 carbon atoms; １ each independently represents a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; and each n independently represents an integer of 0 to 2.

5. Said Z １ is an alkylene group having 21 to 60 carbon atoms.

6. Q ２ The compound according to claim 4, which is represented by the following formula (Q1): １０ ｒ１ -R ５ ｒ２ -Q １１ ｒ３ - ... (Q1) where Q １０ The side is connected to Si, and the Q １１ Side is Z １ and r1 is 0 or 1, r2 is 0 or 1, r3 is 0 or 1, and when r1, r2, and r3 are all 0, ２ is a single bond, and Q １０ is an oxygen atom or an alkylene group; R ５ is -(SiR ６ ２ -O) ｐ３ -SiR ６ ２ - and R ６ are each independently a hydrocarbon group, p3 is a number from 0 to 100, and Q １１ is a carbon-carbon atom bond, R ５ Side end or Z １ At the end of the side, -C(=O)NR ａ１ -, -C(=O)S-, -C(=O)-, -C(=O)O-, -NR ａ１ R is a hydrocarbon group optionally having a bond selected from -, -O-, and -S-; ａ１ are each independently a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a phenyl group, provided that Z １ The alkylene group is not present at the terminal of the alkylene group.

7. A composition containing two or more compounds represented by the following formula (1): R １ Each independently represents １１ ) ３ Si- and R １１ are each independently a compound (1A) which is a hydrocarbon group, and R １ Each independently represents １１ ) ３ Si- and 3 R １１ A composition comprising a compound (1B) in which two or more of [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z １ -Si(R ３ ) ｎ L １ ３－ｎ … (1) where R １ Each independently represents １１ ) ３ Si-, R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ each independently represents an oxygen atom or an alkylene group; R ２ are each independently a hydrocarbon group; R ３ are each independently a hydrocarbon group, each p1 is independently a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, ２ each independently represents a single bond or a divalent linking group; １ each independently represents an alkylene group having 7 to 100 carbon atoms; １ each independently represents a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; and each n independently represents an integer of 0 to 2.

8. The composition according to claim 7, comprising compound (1A) and compound (1B) in a mass ratio of 50 to 99:50 to 1.

9. A composition comprising a compound according to any one of claims 1 to 6 or a composition according to claim 7 or 8, and a liquid medium.

10. A surface treatment agent comprising the compound according to any one of claims 1 to 6 or the composition according to claim 7 or 8.

11. A surface treatment agent comprising the compound according to any one of claims 1 to 6 or the composition according to claim 7 or 8, and a liquid medium.

12. A method for manufacturing an article, comprising: treating a substrate with a surface treatment agent containing a compound according to any one of claims 1 to 6, or a composition according to claim 7 or 8, to manufacture an article having a surface treatment layer formed on the substrate.

13. An article comprising a substrate, and a surface treatment layer disposed on the substrate and surface-treated with a surface treatment agent comprising the compound according to any one of claims 1 to 6, or the composition according to claim 7 or 8.

14. The article of claim 13 which is an optical component.

15. The article according to claim 13, which is a display or a touch panel.

16. A method for producing the compound according to any one of claims 1 to 3, comprising reacting a compound represented by the following formula (3) or a compound represented by the following formula (4) with a compound represented by the following formula (5) or a compound represented by the following formula (6) in the presence of a transition metal compound. １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z ３ -G １ …(3) G １ -Z ３ -Q ２ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z ３ -G １ … (4) R ７ -MgX...(5) R ７ -Li ... (6) where R １ Each independently represents １１ ) ３ Si-, a monovalent cyclic polysiloxane residue, or a monovalent cage-shaped polysiloxane residue; R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ each independently represents an oxygen atom or an alkylene group; R ２ are each independently a hydrocarbon group; R ４ each independently represents a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ -, each p1 is independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, ２ each independently represents a single bond or a divalent linking group; ３ are each independently an alkylene group; １ each independently represents a halogen atom or a sulfonate group which may be substituted with a halogen atom; R ７ are each independently a hydrocarbon group having a carbon-carbon double bond, X is a halogen atom, and Z ３ and R ７ The total number of carbon atoms is 7 to 100.

17. A method for producing the compound according to claim 16, comprising reacting the compound represented by formula (3) or the compound represented by formula (4) with 3 equivalents or more of the compound represented by formula (5) or the compound represented by formula (6).

18. A compound represented by the following formula (7) or the following formula (8): [R １ -Q １ -(SiR ２ ２ -O) ｐ１ ] ｑ１ -SiR ２ ｑ２ -Q ２ -Z ４ -R ２０ … (7) R ２０ -Z ４ -Q ２ -SiR ２ ２ -O-(SiR ４ ２ -O) ｐ２ -SiR ２ ２ -Q ２ -Z ４ -R ２０ … (8) where R １ Each independently represents １１ ) ３ Si-, a monovalent cyclic polysiloxane residue, or a monovalent cage-shaped polysiloxane residue; R １１ each independently represents a hydrocarbon group or a trialkylsilyloxy group; １ each independently represents an oxygen atom or an alkylene group; R ２ are each independently a hydrocarbon group; R ４ each independently represents a hydrocarbon group, or R １ -Q １ -(SiR ２ ２ -O) ｐ１ - and R ２０ are each independently a vinyl group, p1 is each independently a number from 0 to 500, p2 is a number from 0 to 500, q1 is an integer from 1 to 3, q2 is an integer from 0 to 2, q1+q2 is 3, ２ each independently represents a single bond or a divalent linking group; ４ each independently represents an alkylene group having 5 to 98 carbon atoms.

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