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

Abstract

The purpose of the present invention is to provide: a compound capable of forming a surface layer having excellent oil repellency; a surface treatment agent; an article having a surface layer formed from the compound; and a method for producing the article.　This compound is represented by the formula: (Rf)n-L3-L4-L1-(T1)x1. Rf is -OCF3 or the like; n is an integer of 2 or more; L3 is an (n+1)-valent group having no fluorine atom and no organosiloxane residue, or an (n+1)-valent group having no organosiloxane residue, and including a cyclic hydrocarbon group that may contain an oxygen atom or a nitrogen atom as a ring member atom, in which at least one hydrogen atom is substituted with a fluorine atom; L4 is a divalent hydrocarbon group which may have a group such as -O-; L1 is a single bond or a trivalent or higher (1+x1)-valent group; T1 is a reactive group excluding a specific group; and x1 is an integer of 1-10.

Description

Compound, surface treatment agent, article, and method for manufacturing article

[0001] The present invention relates to a compound, a surface treatment agent, an article, and a method for producing an article.

[0002] Methods for forming a surface layer on the surface of a component (substrate) are known in a wide variety of fields, including electrical and electronic materials, semiconductor materials, optical materials, building materials, and automobile parts, with the aim of preventing the component from becoming soiled. For example, Patent Document 1 discloses a method for forming an organic thin film on the surface of a substrate using a composition containing n-octadecyltrimethoxysilane, an organosilicon compound.

[0003] International Publication No. 2008 / 016029

[0004] In recent years, the performance requirements for surface layers have been increasing, and depending on the application, a surface layer with excellent oil repellency is required. The present inventors evaluated a surface layer formed using an organosilicon compound as described in Patent Document 1 and found that there is room for improvement in the oil repellency of the surface layer.

[0005] The present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide a compound capable of forming a surface layer having excellent oil repellency, a surface treatment agent, an article having a surface layer formed from the compound, and a method for manufacturing the article.

[0006] As a result of extensive research into the above-mentioned problems, the present inventors have found that the above-mentioned problems can be solved by the following configuration: [1] A compound represented by the following formula (1): (R ｆ ) ｎ -L ３ -L ４ -L １ - (T １ ) ｘ１ (1) However, R ｆ is -OCF ３ , -SCF ３ , -SF ４ X １１ , -N(CF ３ ) X １２ , -CHF ２ , -CH ２ F, -C ６ F ５, or -C ８ F ７ and X １１ is an alkyl group or a halogen atom, and X １２ is an alkyl group or —CF ３ n is an integer of 2 or more; L ３ is an (n+1)-valent group that is free of fluorine atoms and organosiloxane residues, or an (n+1)-valent group that contains a cyclic hydrocarbon group in which at least one hydrogen atom is substituted with a fluorine atom and that is free of organosiloxane residues, and which may contain an oxygen atom or a nitrogen atom as a ring member atom; L ４ is -O-, -C(=O)-, -C(=O)NX １３ -, -C(=O)O-, -NX １３ C(=O)NX １４ -, -NX １３ C(=S)NX １４ -, -NX １３ C(=O)O-, -Si(X １３ ) ２ -, and a divalent aromatic heterocycle, and when the divalent hydrocarbon group contains a cyclic hydrocarbon group, the cyclic hydrocarbon group may have a substituent; X １３ and X １４ are each independently a hydrogen atom or an alkyl group, and L １ represents a single bond or a trivalent or higher (1+x1)-valent group, １ is a reactive group (excluding vinyl, 1-methylvinyl, (meth)acryloyl, and (meth)acryloyloxy groups), x1 is an integer of 1 to 10, and when x1 is 1, L １ is a single bond, and there are multiple R ｆ may be the same or different, T １ In the case where there are multiple T １ [2] The compound according to [1], wherein the compound represented by the formula (1) is a compound represented by the formula (1-1) described below, wherein in the formula (1-1), L３１ represents a single bond or an (n1+1)-valent hydrocarbon group which may have —O—; L ３２ represents N, C, Si, or a cyclic hydrocarbon group which may contain an oxygen atom or a nitrogen atom as a ring member atom and which may be substituted with a fluorine atom; R １１ represents a hydrogen atom or an alkyl group which may have —O—; １１ represents a single bond or a trivalent or higher (1+x1)-valent group, １２ represents a single bond or a hydrocarbon group which may have —O—, n1 represents an integer of 1 or more, n2 represents an integer of 2 or more, n3 represents an integer of 0 or more, and L ３２ is N, n2 is 2, n3 is 0, and L ３２ is C or Si, n2+n3 is 3, and R ｆ , L ４ , T １ , and x1 are R in formula (1), respectively. ｆ , L ４ , T １ , and x1, and there are multiple (R ｆ ) ｎ１ -L ３１ - may be the same or different. [3] A surface treatment agent comprising the compound according to [1] or [2]. [4] The surface treatment agent according to [3], further comprising a liquid medium. [5] The surface treatment agent according to [3] or [4], which is an antifouling coating agent or a waterproof coating agent. [6] An article having a surface layer formed on the surface of a substrate using the compound according to [1] or [2]. [7] The article according to [6], which is an optical member. [8] The article according to [6] or [7], which has the surface layer on the surface of a member constituting a surface that is touched by a finger of a touch panel. [9] A method for manufacturing an article, in which a surface layer is formed by a dry coating method using the surface treatment agent according to any one of [3] to [5].

[10] A method for manufacturing an article, in which a surface layer is formed by a wet coating method using the surface treatment agent according to any one of [3] to [5].

[0007] According to the present invention, it is possible to provide a compound capable of forming a surface layer having excellent oil repellency, a surface treatment agent, an article having a surface layer formed from the compound, and a method for producing the article.

[0008] 1 is a schematic cross-sectional view showing an example of an article of the present invention.

[0009] The meanings of the terms used in the present invention are as follows. In this specification, a compound represented by formula (1) will be referred to as Compound 1. Compounds represented by other formulas will also be referred to as such. A "fluoroalkyl group" is a collective term that includes perfluoroalkyl groups and partial fluoroalkyl groups. A "perfluoroalkyl group" refers to a group in which all of the hydrogen atoms of an alkyl group are substituted with fluorine atoms. A "partial fluoroalkyl group" refers to an alkyl group in which one or more hydrogen atoms are substituted with fluorine atoms and which also has one or more hydrogen atoms. In other words, a fluoroalkyl group is an alkyl group having one or more fluorine atoms. A fluoroalkylene group also has this meaning. A "reactive silyl group" is a collective term for hydrolyzable silyl groups and silanol groups (Si—OH), and a "hydrolyzable silyl group" refers to a group that can form a silanol group by hydrolysis. An "organic group" refers to a hydrocarbon group that may have a substituent and may have a heteroatom or other bond in the carbon chain. The term "hydrocarbon group" refers to an aliphatic hydrocarbon group (such as a linear alkylene group, a branched alkylene group, or a cycloalkylene group), an aromatic hydrocarbon group (such as a phenylene group), or a group consisting of a combination thereof. The term "surface layer" refers to a layer formed on the surface of a substrate. The term "to" indicating a range of values ​​means that the values ​​before and after it are included as the lower and upper limits. The order of bonding in each divalent group is not limited unless otherwise specified. For example, the following L １ -C(=O)N(R ２６ )-, the left bond is R １ The bond on the right side may be R １It may be bonded to the side. 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. When the same symbol is present in one chemical formula, the same symbols may represent the same structure or may represent different structures within the specified range. In this specification, "Me" may represent a methyl group.

[0010] [Compound 1] The compound of the present invention is represented by the following formula (1).

[0011] (R ｆ ) ｎ -L ３ -L ４ -L １ - (T １ ) ｘ１ (1)

[0012] In formula (1), R ｆ is -OCF ３ , -SCF ３ , -SF ４ X １１ , -N(CF ３ ) X １２ , -CHF ２ , -CH ２ F, -C ６ F ５ , or -C ８ F ７ and X １１ is an alkyl group or a halogen atom, and X １２ is an alkyl group or —CF ３ n is an integer of 2 or more; L ３ is an (n+1)-valent group that is free of fluorine atoms and organosiloxane residues, or an (n+1)-valent group that contains a cyclic hydrocarbon group in which at least one hydrogen atom is substituted with a fluorine atom and that is free of organosiloxane residues, and which may contain an oxygen atom or a nitrogen atom as a ring member atom; L ４ is -O-, -C(=O)-, -C(=O)NX １３ -, -C(=O)O-, -NX １３ C(=O)NX １４-, -NX １３ C(=S)NX １４ -, -NX １３ C(=O)O-, -Si(X １３ ) ２ -, and a divalent aromatic heterocycle, and when the divalent hydrocarbon group contains a cyclic hydrocarbon group, the cyclic hydrocarbon group may have a substituent; X １３ and X １４ are each independently a hydrogen atom or an alkyl group, and L １ represents a single bond or a trivalent or higher (1+x1)-valent group, １ is a reactive group (excluding vinyl, 1-methylvinyl, (meth)acryloyl, and (meth)acryloyloxy groups), x1 is an integer of 1 to 10, and when x1 is 1, L １ is a single bond, and there are multiple R ｆ may be the same or different, T １ In the case where there are multiple T １ may be the same or different from each other.

[0013] Compound 1 is a fluorine-containing group R ｆ and a reactive group T １ When a surface layer is formed using Compound 1, the reactive group of Compound 1 is likely to be located on the substrate side and is strongly chemically bonded to the substrate, so that the resulting surface layer has excellent abrasion resistance. ｆ Although the details of the reason are unknown, by having a plurality of groups, a surface layer having excellent oil repellency can be obtained.

[0014] R ｆ is -OCF ３ , -SCF ３ , -SF ４ X １１ , or -N(CF ３ ) X １２ , -CHF ２ , -CH ２ F, -C６ F ５ , -C ８ F ７ and from the viewpoint of superior oil repellency of the surface layer, -OCF ３ , -SF ４ X １１ is preferred, and -OCF ３ is more preferred. ４ X １１ X in １１ is an alkyl group or a halogen atom. １１ The number of carbon atoms in the alkyl group in X is preferably 1 to 8, and more preferably 1 to 4. When the alkyl group has 3 or more carbon atoms, the alkyl group having 3 or more carbon atoms may be linear or may have a branched or cyclic structure. １１ Specific examples of the halogen atom in —N(CF ３ ) X １２ X in １２ is an alkyl group or —CF ３ X １２ The number of carbon atoms in the alkyl group in the formula (I) is preferably 1 to 8, more preferably 1 to 4. When the alkyl group has 3 or more carbon atoms, the alkyl group having 3 or more carbon atoms may be linear or may have a branched or cyclic structure. ｆ may be the same or different from each other.

[0015] L ３ is an (n+1)-valent group that does not contain a fluorine atom or an organosiloxane residue, or an (n+1)-valent group that contains a cyclic hydrocarbon group in which at least one hydrogen atom is substituted with a fluorine atom and that does not contain an organosiloxane residue, and may contain an oxygen atom or a nitrogen atom as a ring member atom. The (n+1)-valent group may contain a heteroatom such as O, N, or Si, and may have a branch point. ３ L in the middle ４ The atom bonded to L is preferably N, a carbon atom constituting a branch point, or Si. ３ is at least one branch point (hereinafter referred to as "branch point P") selected from the group consisting of N, C, Si, and a ring structure. １It is preferable that N is a branch point P １ In this case, the branch point P １ For example, *-N(-**) ２ where * is L ４ is a bond on the side, and ** is R ｆ C is the branch point P １ In this case, the branch point P １ For example, *-C(-**) ３ or *-CR １１ (-**) ２ where * and ** indicate that N is the branch point P １ This is the same as when R １１ is a hydrogen atom or an alkyl group which may have —O—. １ In this case, the branch point P １ For example, *-Si(-**) ３ or *-SiR １１ (-**) ２ where * and ** indicate that N is the branch point P １ This is the same as when R １１ C is the branch point P １ This is the same as when

[0016] Branch point P １ Examples of the ring structure constituting the ring structure include cyclic hydrocarbon groups which may contain oxygen atoms or nitrogen atoms as ring member atoms. The hydrogen atoms of the cyclic hydrocarbon group may be substituted with fluorine. Specific examples of the cyclic hydrocarbon group which may contain oxygen atoms or nitrogen atoms as ring member atoms include 3- to 8-membered aliphatic rings, 6-membered aromatic hydrocarbon rings, 3- to 8-membered aliphatic heterocycles which contain oxygen atoms or nitrogen atoms as ring member atoms, 5- to 6-membered aromatic heterocycles which contain oxygen atoms or nitrogen atoms as ring member atoms, and fused rings consisting of two or more of these rings. Branch point P １ Examples of the ring structure constituting the ring structure include the following: In the ring structures exemplified below, one of the hydrogen atoms is L ４ Bond with, two or more are R ｆThe remaining hydrogen atoms are bonds to the side, and one or more of the remaining hydrogen atoms may be substituted with a fluorine atom.

[0017]

[0018] L ３ may have a hydrocarbon group which may have -O-. Examples of the hydrocarbon group include an aliphatic hydrocarbon group (which may be saturated or unsaturated, and may be linear, branched, or cyclic), an aromatic hydrocarbon group, and a group formed by combining these. In view of the superior oil repellency of the surface layer, an aliphatic hydrocarbon group is preferred, and a saturated aliphatic hydrocarbon group is more preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 20. The number of carbon atoms in the hydrocarbon group may be 1 to 10, 1 to 6, or 1 to 4.

[0019] L ３ In a preferred embodiment, the hydrocarbon group may have one or more —O— groups and one or more branching points P １ or a branch point P １ An embodiment consisting of only (L ３１ ) ｎ２ -L ３２ (R １１ ) ｎ３ The structure of L ３ Specific examples of -C(-CH ２ -**) ３ , *-CH(-CH ２ -**) ２ , *-CH(-CH ２ -**) (-**). * is L ４ is a bond on the side, and ** is R ｆ It is the connecting hand on the side.

[0020] L ４ is -O-, -C(=O)-, -C(=O)NX １３ -, -C(=O)O-, -NX １３ C(=O)NX １４ -, -NX １３ C(=S)NX １４ -, -NX １３ C(=O)O-, -Si(X １３ )２ - and a divalent aromatic heterocycle (wherein X １３ and X １４ are each independently a hydrogen atom or an alkyl group. １ "). Examples of the divalent hydrocarbon group include a divalent saturated hydrocarbon group, a divalent unsaturated hydrocarbon group, a divalent aromatic hydrocarbon group, and groups formed from a combination thereof. The divalent saturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include an alkylene group and a cycloalkylene group. The divalent saturated hydrocarbon group preferably has 1 to 40 carbon atoms, more preferably 1 to 30, and even more preferably 1 to 20 carbon atoms. The cycloalkylene group may have a monocyclic structure or a polycyclic structure. The cycloalkylene group may have a substituent described below. The divalent unsaturated hydrocarbon group may be linear, branched, or cyclic, and examples thereof include an alkenylene group, a cycloalkenylene group, and an alkynylene group. The divalent saturated hydrocarbon group preferably has 2 to 40 carbon atoms. The cycloalkenylene group may have a monocyclic structure or a polycyclic structure. The cycloalkenylene group may have a substituent as described below. The divalent aromatic hydrocarbon group is preferably a group having 5 to 20 carbon atoms, such as a phenylene group. The divalent aromatic hydrocarbon group may have a monocyclic structure or a polycyclic structure, and may have a substituent as described below. L ４ When the divalent hydrocarbon group in the formula (I) contains a cyclic hydrocarbon group (for example, the above-mentioned cycloalkylene group, the above-mentioned cycloalkenylene group, or the above-mentioned divalent aromatic hydrocarbon group), the cyclic hydrocarbon group may have a substituent. Specific examples of the substituent include an alkyl group which may have —O— and a halogen atom.

[0021] L ４ The divalent hydrocarbon group may have a group W １ is -O-, -C(=O)-, -C(=O)NX １３ -, -C(=O)O-, -NX １３ C(=O)NX １４ -, -NX １３C(=S)NX １４ -, -NX １３ C(=O)O-, -Si(X １３ ) ２ - and a divalent aromatic heterocycle (wherein X １３ and X １４ are each independently a hydrogen atom or an alkyl group.) and from the viewpoint of more excellent oil repellency of the surface layer, -O-, -C(=O)O-, -Si(X １３ ) ２ - and -C(=O)NX １３ - is preferably at least one group selected from the group consisting of -O- and -C(=O)NX １３ It is more preferable that the group W is at least one group selected from the group consisting of １ X in each group １３ and X １４ are each independently a hydrogen atom or an alkyl group. １３ and X １４ The number of carbon atoms in the alkyl groups in each group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. When the alkyl group has 3 or more carbon atoms, the alkyl group having 3 or more carbon atoms may be linear or may have a branched or cyclic structure. １ Specific examples of the heteroatom contained in the divalent aromatic heterocycle in the formula (I) include O, S, and N. The divalent aromatic heterocycle is preferably a 5- to 10-membered ring, and more preferably a 5- or 6-membered ring.

[0022] L ４ Is, L ３ It may have —O— or —C(═O)— at the position bonding to the above.

[0023] L ４ L in １ Specific examples of the group at the position where it bonds to include *-CH ２ -**, *-C(=O)NX １３ -CH ２ -**, *-O-CH ２ -**, *-C(=O)O-CH ２ -**. In the formula, X １３ is as described above, and * is L４ represents the bonding position with the residue of １ represents the bonding position with

[0024] L ４ is preferably a group represented by the following formula (L4): １１ - (R ３１ -W １２ ) ｋ１ -R ３２ -** ... (L4) where W １１ and W １２ are each independently a single bond or the above-mentioned W １ is a divalent group represented by R ３１ and R ３２ are each independently a divalent hydrocarbon group, k1 is an integer of 0 to 6, * is L ３ indicates the bonding position on the L １ The bond position on the side is shown.

[0025] W １１ "W" in １ The divalent group represented by the formula "W" is １ and preferably —O— or —C(═O)—. １１ is preferably a single bond, —O— or —C(═O)—. １２ "W" in １ The divalent group represented by the formula "W" is １ and preferably —O—, —C(═O)—, —C(═O)NX １３ -, -C(=O)O-, -NX １３ C(=O)O-. W １２ Among them, a single bond, —O—, —C(═O)—, —C(═O)NX １３ -, -C(=O)O- or -NX １３ C(=O)O- is preferred. ３１ is a divalent hydrocarbon group, preferably -R ５１ -, -R ５２ -, -R ５１ -R ５２ -or-R ５１ -R ５２ -R ５１ - and R ５１is a linear alkylene group having 1 to 12 carbon atoms, and R ５２ is a cycloalkylene group having 4 to 8 carbon atoms or a phenylene group which may be substituted with a fluorine atom. ３２ is a divalent hydrocarbon group, preferably a linear alkylene group having 1 to 60 carbon atoms, more preferably a linear alkylene group having 1 to 48 carbon atoms, and even more preferably a linear alkylene group having 1 to 36 carbon atoms. k1 is an integer of 0 to 6, preferably 0 to 2, and more preferably 0 to 1.

[0026] (R ｆ ) ｎ -L ３ -L ４ In the group represented by -, L ３ and L ４ The separator is L ４ The number of carbon atoms in the divalent hydrocarbon group in -L is the largest. ４ -L １ - (T １ ) ｘ１ In the group represented by １ and L ４ The separator is L ４ The number of carbon atoms in the divalent hydrocarbon group is set to be the largest.

[0027] n is an integer of 2 or more. From the viewpoint of ease of synthesis, n is preferably an integer of 10 or less, and more preferably an integer of 4 or less.

[0028] L １ is a single bond or a trivalent or higher (1+x1) valent group.

[0029] Here, if x1 is 1, L １ On the other hand, when x1 is 2 or more, the (1+x1)-valent group has at least one branch point (hereinafter referred to as "branch point P") selected from the group consisting of C, N, Si, and a ring structure. ２ ").

[0030] Branch point P ２As the ring structure constituting the above, from the viewpoint of ease of synthesis and superior abrasion resistance, light resistance, and chemical resistance of the surface layer, one selected from the group consisting of a 3- to 8-membered aliphatic ring, a 6-membered aromatic ring, a 5- to 6-membered heterocyclic ring, and a fused ring consisting of two or more of these rings is preferred, and the ring structure shown in the following formula is more preferred. The ring structure may have a substituent such as a halogen atom, an alkyl group (which may contain an etheric oxygen atom between carbon atoms), a cycloalkyl group, an alkenyl group, an allyl group, an alkoxy group, or an oxo group (=O). However, in the ring structures exemplified below, one of the hydrogen atoms is L ４ The two bonds are T １ It is a combination of.

[0031]

[0032] L １ is an alkylene group, a hydroxyalkylene group, an alkoxyalkylene group, a carbonyl group, an amide bond, an ether bond, a thioether bond, a urea bond, a urethane bond, a carbonate bond, an ester bond, -SO ２ NR ２６ -, -Si(R ２６ ) ２ -, -OSi(R ２６ ) ２ -, -Si(CH ３ ) ２ -Ph １ -Si(CH ３ ) ２ - and a group containing one or more selected from divalent organopolysiloxane residues (hereinafter referred to as "group B １０ "). However, R ２６ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph １ is a phenylene group. ２６ The number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, from the viewpoint of ease of production of compound 1.

[0033] Examples of the divalent organopolysiloxane residue include groups of the following formula: ２７is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. ２７ The alkyl group and alkoxy group preferably have 1 to 10 carbon atoms, and more preferably 1 carbon atom.

[0034]

[0035] L １ is preferably -C(=O)NR from the viewpoint of ease of synthesis. ２６ -, -C(=O)-, -C(=O)OR ２６ -, -NR ２６ It is preferable that the surface layer has at least one bond selected from the group consisting of — and —O—, and in terms of excellent light resistance and chemical resistance, it is preferable that the surface layer has at least one bond selected from the group consisting of —C(═O)NR ２６ It is more preferred that it has - or -C(=O)-.

[0036] L １ In a preferred embodiment, the alkylene group has one or more divalent hydrocarbon groups and one or more branching points P ２ or a combination of one or more hydrocarbon groups and one or more branching points P ２ and one or more groups B １０ and combinations thereof. Specific examples of the divalent hydrocarbon group include divalent aliphatic hydrocarbon groups (such as alkylene groups and cycloalkylene groups) and divalent aromatic hydrocarbon groups (such as phenylene groups). The divalent hydrocarbon group preferably has 1 to 20 carbon atoms. The divalent hydrocarbon group may have 1 to 6 carbon atoms or 1 to 4 carbon atoms.

[0037] L １ For example, *-C(-CH ２ CH ２ CH ２ -**) ３ , *-CH(-CH ２ CH ２ CH ２ -**) ２ , *-C(Me)(-CH ２ CH ２ CH ２ -**) ２ , *-Si(-CH ２ CH ２ CH ２ -**) ３ , *-SiH(-CH２ CH ２ CH ２ -**) ２ , *-Si(Me)(-CH ２ CH ２ CH ２ -**) ２ , *-N(-CH ２ CH ２ CH ２ -**) ２ , *-CH(-CH ２ -O-CH ２ CH ２ CH ２ -**) ２ , *-Si(-CH ２ -**) (-**) ２ , *-CH(-C １１ H ２２ -**) ２ , *-Si(-O-CH ２ CH ２ -**) (-CH ２ CH ２ CH ２ -**) ２ , *-C(-CH ２ -O-CH ２ CH ２ CH ２ -**) ３ , and groups represented by the following formula: * represents L ４ represents the bonding position with T １ represents the bonding position with

[0038]

[0039] L ４ and L １ The separator is L ４ The number of carbon atoms in the divalent hydrocarbon group is set to be the largest.

[0040] T １ is a reactive group (excluding vinyl, 1-methylvinyl, (meth)acryloyl, and (meth)acryloyloxy groups), and T １Due to the reactivity of Compound 1, Compound 1 exhibits various functions. Examples of such functions include a function of improving adhesion to a substrate surface, a function of imparting photocurability or thermosetting property to Compound 1, a function of imparting acidity or alkalinity to Compound 1, a function of adjusting the solubility of Compound 1 in a specific solvent, and a function as a precursor for synthesizing other compounds.

[0041] T １ Specific examples of -Ar include １ , -OR １０ , -SR １０ , -NOR １０ , -C(=O)R １０ , -N(R １０ ) ２ , -N ＋ (R １０ ) ３ X ３ , -C≡N, -C(=NR １０ )-R １０ , -N ＋ ≡N, -N=NR １０ , -C(=O)OR １０ , -C(=O)OX ２ , -C(=O)X ４ , -C(=O)OC(=O)R １０ , -OC(=O)-CH ２ =CH ２ -C(=O)OR １０ , -CH(OH)-CH ２ (OH), -SO ２ R １０ , -SO ２ X ４ , -SO ３ H, -SO ３ X ２ , -P(=O)(-OR １０ ) ２ , -OP(=O)(-OR １０ ) ２ , -OP(=O)(-OR １０ ) (-OX ２ ), -N=C=O, -N=C=S, -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ , -SiH(R １０ ) ２ , -Si(-OC２ H ４ -OCH ３ ) ３ , -Si[-N(CH ３ ) ２ ] ３ , -C≡C(R １０ ), -C(=O)N(R １０ ) ２ , -N(R １０ ) C(=O)R １０ , -Si(R １０ ) ２ —O—Si(R １０ ) ３ , -NH-C(=O)R １０ , -C(=O)NHR １０ , -I, -Br, -B(OH) ２ , -N ３ , and groups represented by the following formula:

[0042]

[0043] However, R １０ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or an aryl group which may have a substituent, and Ar １ represents an aryl group which may have a substituent, and X ２ is an alkali metal ion or an ammonium ion, and X ３ is a halide ion, and X ４ is a halogen atom, R ａ１ is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and R ａ１１ is a hydrocarbon group, z1 is an integer of 1 to 3, R １０ , R ａ１ or R ａ１１ In the case where there are multiple R １０ , R ａ１ or R ａ１１ may be the same or different from each other.

[0044] Ar １ and R １０The aryl group in R may be a phenyl group, a naphthyl group, or the like, and may further have a substituent. Examples of the substituent that the aryl group may have include a halogen atom such as a fluorine atom or a chlorine atom, an alkyl group having 1 to 6 carbon atoms, and the same groups as those exemplified as the functionality-imparting group T. １０ The alkyl group in the formula (I) has 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. The alkyl group may have another substituent. Examples of the substituent that the alkyl group may have include a halogen atom such as a chlorine atom, and the same groups as those exemplified as the functionality-imparting group T described below.

[0045] T １ Compound 1 having a hydroxy group, N-hydroxy group, aldehyde group, ketone group, amino group, quaternary ammonium group, nitrile group, imino group, diazo group, carboxy group, carboxylate, acid anhydride group, sulfo group, sulfonate, phosphoric acid group, or phosphate (hereinafter, these groups will be referred to as "functionality-imparting group T") as a functional group T is endowed with various properties such as acidity, alkalinity, and hydrophilicity, and imparts functions such as improved solubility in specific solvents and improved adhesion to specific substrates. Examples of counter ions for the quaternary ammonium group include halide ions. Examples of counter ions for the carboxylate, sulfonate, and phosphate include alkali metal ions and ammonium ions. In addition, T １ Compound 1 having an isocyanate group, an isothiocyanate group, an epoxy group, a glycidyl group, an oxetanyl group, or a mercapto group as the substituent can be combined with an epoxy curing agent to prepare a thermosetting or photocurable composition, and the cured coating film obtained from the composition has both water and oil repellency and hard coating properties. １ The amide bond, ester bond, ether bond, thioether bond, siloxane bond, and urea bond in １ It is a bond that connects an alkyl group, a fluoroalkyl group, an aryl group, a heteroaryl group, etc. contained in the above. Other functionality-imparting groups may be further provided via these bonds.

[0046] T contained in Compound 1 １As the group, a hydroxy group, an amino group, a carboxy group, or a mercapto group is preferred from the viewpoint of ease of synthesis, chemical stability, adhesion to the substrate, and the like.

[0047] In addition, when Compound 1 is used as a surface treatment agent for forming a surface layer having excellent durability such as abrasion resistance, T １ is preferably a group having a reactive silyl group. The group having a reactive silyl group is preferably a group represented by the following formula (2):

[0048] -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ (2)

[0049] In formula (2), R ａ１ is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and R ａ１１ is a hydrocarbon group, z1 is an integer of 1 to 3, R ａ１ , or R ａ１１ If there are multiple R ａ１ , or R ａ１１ may be the same or different.

[0050] R ａ１ is a hydroxyl group, it forms a silanol (Si-OH) group together with the Si atom. A hydrolyzable group is a group that becomes a hydroxyl group through a hydrolysis reaction. The silanol group further reacts with other molecules to form a Si-O-Si bond. The silanol group also undergoes a dehydration condensation reaction with a hydroxyl group (substrate-OH) on the surface of the substrate to form a chemical bond (substrate-O-Si). Compound 1 is a compound of T １ By containing one or more of the above, the surface layer has excellent abrasion resistance after formation.

[0051] R ａ１ Examples of the hydrolyzable group include an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, an amino group, an isocyanate group (—NCO), and —O—N═CR ｒ ２ (R ｒare each independently an alkyl group having 1 to 10 carbon atoms), an alkylene oxide-modified alkoxy group, etc. As the alkoxy group, an alkoxy group having 1 to 4 carbon atoms is preferred. As the acyl group, an acyl group having 1 to 6 carbon atoms is preferred. As the acyloxy group, an acyloxy group having 1 to 6 carbon atoms is preferred.

[0052] R ａ１ Examples of the hydrolyzable group in the group having a hydrolyzable group include the hydrolyzable groups 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 ａ１ Specific examples of groups having a hydrolyzable group include —O—CH , which is also one of the alkylene oxide-modified alkoxy groups. 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 １ In this case, a group represented by the formula: ４１ is an alkylene group having 1 to 10 carbon atoms, and L １ 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] R ａ１ is an alkoxy group having 1 to 4 carbon atoms, the above-mentioned -OL, from the viewpoint of ease of synthesis. Ａ -L Ｂ or a halogen atom is preferred. ａ１The alkoxy group in is preferably an alkoxy group having 1 to 4 carbon atoms in terms of providing excellent storage stability to Compound 1 and suppressing outgassing during the reaction, more preferably an ethoxy group in terms of long-term storage stability, and more preferably a methoxy group in terms of shortening the hydrolysis reaction time. Furthermore, the halogen atom is preferably a chlorine atom.

[0054] R ａ１１ is a hydrocarbon group. Examples of the hydrocarbon group include an alkyl group, a cycloalkyl group, an alkenyl group, and an allyl group. From the viewpoint of ease of synthesis, an alkyl group is preferred. From the viewpoint of ease of synthesis, the number of carbon atoms in the hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2.

[0055] R in Group 2 ａ１ The number z1 may be 1 to 3, and from the viewpoint of excellent adhesion to the substrate, it is preferably 2 or 3, and more preferably 3. Specific examples of the group 2 include -Si(OCH ３ ) ３ , -Si(CH ３ ) (OCH ３ ) ２ , -Si(CH ３ ) ２ (OCH ３ ), —Si(OCH ２ CH ３ ) ３ , -Si(OCH ２ CH ２ OCH ３ ) ３ , -SiCl ３ , -Si(OCOCH ３ ) ３ , —Si(NCO) ３ , -Si(NMe ２ ) ３ , —Si(OH) ３ From the viewpoint of ease of handling during production, -Si(OCH ３ ) ３ is preferred.

[0056] T １ Preferred embodiments of the formula include the following structures: １０ and * indicates a bond.

[0057]

[0058] T １ x1, which represents the number of T, may be 1 to 10, and from the viewpoint of ease of synthesis and ease of handling of Compound 1, x1 is preferably 1 to 6, and more preferably 1 to 3. １ In the case where there is a T １ may have the same structure as each other or may have different structures.

[0059] T １ has a reactive silyl group, and L １ is the branch point P ２ In the case where -L １ - (T １ ) ｘ１ Examples of the group represented by the formula include the following structure: wherein * represents a bond.

[0060]

[0061] <Preferred Embodiment of Compound 1> Compound 1 is preferably a compound represented by formula (1-1) (hereinafter referred to as "compound 1-1"), in terms of achieving better effects of the present invention.

[0062] (Compound 1-1) Compound 1-1 is a compound represented by the following formula (1-1).

[0063]

[0064] In formula (1-1), L ３１ represents a single bond or an (n1+1)-valent hydrocarbon group which may have —O—; L ３２ represents N, C, Si, or a cyclic hydrocarbon group which may contain an oxygen atom or a nitrogen atom as a ring member atom and which may be substituted with a fluorine atom; R １１ represents a hydrogen atom or an alkyl group which may have —O—; １１ represents a single bond or a trivalent or higher (1+x1)-valent group, １２represents a single bond or a hydrocarbon group which may have —O—, n1 represents an integer of 1 or more, n2 represents an integer of 2 or more, n3 represents an integer of 0 or more, and L ３２ is N, n2 is 2, n3 is 0, and L ３２ is C or Si, n2+n3 is 3, and R ｆ , L ４ , T １ , and x1 are R in formula (1), respectively. ｆ , L ４ , T １ , and x1, and there are multiple (R ｆ ) ｎ１ -L ３１ - may be the same or different.

[0065] L １１ is a single bond or a trivalent or higher (1+x1)-valent group. １１ The (1+x1)-valent group in the formula (L) may have a heteroatom such as N, O, S, or Si, and may have a branch point. １１ L in the middle ４ and L １２ The atoms bonded to L are preferably each independently N, O, S, Si, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (═O). １１ When is a single bond, L in formula (1) ４ and L １２ is directly bonded. １１ is a single bond, and L １２ is a single bond, compound 1 is ４ and T １ is directly bonded.

[0066] L １１ is a trivalent or higher valent group, L １１ is at least one branch point (hereinafter referred to as "branch point P") selected from the group consisting of C, N, Si, and a ring structure. ２１ ").

[0067] N is the branch point P ２１ In this case, the branch point P ２１ For example, *-N(-**) ２where * is L ４ is a bond on the side, and ** is L １２ C is the branch point P ２１ In this case, the branch point P ２１ For example, *-C(-**) ３ or *-CR ２９ (-**) ２ where * and ** indicate that N is the branch point P ２１ This is the same as when R ２９ is a monovalent group, and examples thereof include a hydrogen atom, a hydroxyl group, an alkyl group, and an alkoxy group. ２１ In this case, the branch point P ２１ For example, *-Si(-**) ３ or *-SiR ２９ (-**) ２ where * and ** indicate that N is the branch point P ２１ This is the same as when R ２９ C is the branch point P ２１ This is the same as when

[0068] Branch point P ２１ Specific examples of the ring structure constituting the above-mentioned branch point P ２ The ring structure is similar to that in

[0069] Trivalent or higher L １１ is -C(=O)N(R ２６ )-, -C(=O)O-, -C(=O)-, -C(OH)-, -O-, -N(R ２６ )-, -S-, -OC(=O)O-, -NHC(=O)O-, -NHC(=O)N(R ２６ ) -, -SO ２ N (R ２６ ) -, -N(R ２６ ) SO ２ -, -Si(R ２６ ) ２ -, -OSi(R ２６ ) ２ - and -Si(CH ３ ) ２ -Ph １ -Si(CH ３ ) ２- (hereinafter, "bond B") １ "). However, R ２６ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph １ is a phenylene group. ２６ The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of compound 1.

[0070] Join B １ Specific examples of the divalent organopolysiloxane residue in the above are the above-mentioned group B １０ It is the same as the organopolysiloxane residue in

[0071] Join B １ From the viewpoint of ease of synthesis, -C(=O)NR ２６ -, -C(=O)-, and -NR ２６ In order to provide a surface layer with even better light resistance and chemical resistance, at least one bond selected from the group consisting of —C(═O)NR ２６ - or -C(=O)- is more preferred.

[0072] Trivalent or higher L １１ Is, L ４ and L １２ It is preferable that the atoms bonded to each independently be N, O, S, Si, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (═O). ４ and L １２ The atoms adjacent to each bond B １ Or branch point P ２１ It is preferable that the L is a trivalent or higher constituent element. １１ As a specific example of ２１ (For example, {*-P ２１ (-**) ｘ１}), one or more branch points P ２１ and one or more bonds B １ and combinations (for example, *-B １ -R ２８ -P ２１ (-**) ｘ１}, {*-B １-R ２８ -P ２１ (-R ２８ -B １ -**) ｘ１}), where R ２８ represents a single bond or a divalent organic group, and * represents L ４ is a bond on the side, and ** is L １２ It is the connecting hand on the side.

[0073] The above R ２８ Examples of the divalent organic group in the formula include a divalent aliphatic hydrocarbon group (such as an alkylene group or a cycloalkylene group) and a divalent aromatic hydrocarbon group (such as a phenylene group), and the hydrocarbon group having two or more carbon atoms has a bond B between carbon atoms. １ The divalent organic group preferably has 1 to 20 carbon atoms. The divalent organic group may have 1 to 6 carbon atoms, or may have 1 to 4 carbon atoms.

[0074] The above L １１ As the group, a group represented by any one of the following formulae (E1) to (E5) and (E7) is preferred in terms of ease of production of compound 1.

[0075] -E １ -C(R Ｅ２ ) ３－ｅ３ (-E ２２ -) ｅ３ (E2) -E ２ -N (-E ２３ -) ２ (E3) -E ３ -Z １ (-E ２４ -) ｅ４ (E4) -E ２ -Si(R Ｅ３ ) ３－ｅ３ (-E ２５ -) ｅ３ (E5) -E １ -CH(-E ２２ -)-Si(R Ｅ３ ) ３－ｅ５ (-E ２５ -) ｅ５ (E7) However, in the formulas (E1) to (E5) and (E7), E １ , E ２or E ３ The L side of formula (1-1) ４ Connect with E ２２ , E ２３ , E ２４ or E ２５ Side is L １２ where E １ is a single bond or -B ５ - and B ５ is -C(=O)NR Ｅ６ -, -C(=O)-, -NR Ｅ６ - or -O-, E ２ is a single bond or —C(═O)—, ３ Is E ３ Z to which １ When the atom in is a carbon atom, E １ and E ３ Z to which １ When the atom in is a nitrogen atom, E ２ and E １１ represents a single bond, —O—, an alkylene group, or an alkylene group having two or more carbon atoms with —C(═O)NR between carbon atoms. Ｅ６ -, -C(=O)-, -NR Ｅ６ - or -O-, ２２ is a single bond, -B ５ -, -R ４０ -B ６ -or-B ５ -R ４０ -B ６ - and E ２２ When there are two or more, there are two or more E ２２ may be the same or different, R ４０ represents an alkylene group or an alkylene group having two or more carbon atoms with —C(═O)NR between carbon atoms. Ｅ６ -, -C(=O)-, -NR Ｅ６ - or -O-, and B ６ is -C(=O)NR Ｅ６ -, -C(=O)-, or -NR Ｅ６ - and E ２３ is a single bond or -R ４０ -B ６ - and two E ２３may be the same or different, E ２４ Is E ２４ Z to which １ When the atom in is a carbon atom, E ２２ and E ２４ Z to which １ When the atom in is a nitrogen atom, E ２３ and E ２４ When there are two or more, there are two or more E ２４ may be the same or different, E ２５ is a single bond or -R ４０ -B ６ - and E ２５ When there are two or more, there are two or more E ２５ may be the same or different, Z １ Is E ３ has a carbon atom or nitrogen atom to which E is directly bonded, ２４ is a group having an (e4+1)-valent ring structure having a carbon atom or a nitrogen atom to which R is directly bonded, Ｅ１ is a hydrogen atom or an alkyl group, and R Ｅ１ When there are two or more R Ｅ１ may be the same or different, R Ｅ２ is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group, and R Ｅ３ is an alkyl group, and R Ｅ６ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, e1 is an integer from 0 to 2, e2 is an integer from 0 to 3, and e1+e2 is an integer from 1 to 5, e3 is an integer from 1 to 3, e4 is an integer of 1 or more, and e5 is an integer from 1 to 3. Note that e1+e2=x1, e3=x1, e4=x1, and e5+1=x1.

[0076] R ４０ The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, from the viewpoints of ease of production of Compound 1 and further superior abrasion resistance, light resistance, and chemical resistance of the surface layer. However, when a specific bond is present between carbon atoms, the lower limit of the number of carbon atoms in the alkylene group is 2.

[0077] Z１ Examples of the ring structure in Z include the ring structures described above, and the preferred embodiments are also the same. １ The ring structure in ２４ is directly bonded to the ring structure, for example, an alkylene group is linked to the alkylene group, and E ２４ are never connected.

[0078] R Ｅ１ , R Ｅ２ or R Ｅ３ The number of carbon atoms in the alkyl group of R is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of compound 1. Ｅ２ The number of carbon atoms in the alkyl group portion of the acyloxy group in e4 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of compound 1. e4 is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3, from the viewpoint of ease of production of compound 1 and further improved abrasion resistance and fingerprint removability of the surface layer.

[0079] L １１ Other examples of the group include groups represented by any of the following formulae (E11) to (E15) and (E17).

[0080] -E １ -C(R Ｅ２ ) ３－ｅ３ (-E ２２ -E Ｇ -) ｅ３ (E12) -E ２ -N (-E ２３ -E Ｇ -) ２ (E13) -E ３ -Z １ (-E ２４ -E Ｇ -) ｅ４ (E14) -E ２ -Si(R Ｅ３ ) ３－ｅ３ (-E ２５ -E Ｇ -) ｅ３ (E15) -E １ -CH(-E ２２ -)-Si(R Ｅ３ )３－ｅ５ (-E ２５ -E Ｇ -) ｅ５ (E17)

[0081] However, in the formulas (E11) to (E15) and (E17), E １ , E ２ or E ３ The L side of formula (1-1) ４ Connect with E ２２ , E ２３ , E ２４ or E ２５ Side is L １２ Connect to E Ｇ is expressed by the following formula (E Ｇ ) and L １１ has 2 or more E Ｇ may be the same or different. Ｇ The symbols other than are the same as those in formulas (E1) to (E5) and (E7). ２３ ) ３－ｋ (-E ３０ -) ｋ (E Ｇ ) where the formula (E Ｇ ) in which the Si side is E ２２ , E ２３ , E ２４ or E ２５ Connect to E ３０ Side is L １２ Connect to R ２３ is an alkyl group. ３０ is a single bond or -R ４５ -B ６ - and R ４５ represents an alkylene group or an alkylene group having two or more carbon atoms with —C(═O)NR between carbon atoms. ４６ -, -C(=O)-, -NR ４６ - or -O- containing group, or -(OSi(R ２４ ) ２ ) ｐ -O-, and two or more E ３０ may be the same or different. k is 2 or 3. R ４６ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. ２４is an alkyl group, a phenyl group, or an alkoxy group, and two R ２４ may be the same or different. p is an integer of 0 to 5, and when p is 2 or more, there are two or more (OSi(R ２４ ) ２ ) may be the same or different.

[0082] E ３０ The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, from the viewpoints of ease of production of compound 1 and further superior abrasion resistance, light resistance, and chemical resistance of the surface layer. However, when there is a specific bond between carbon atoms, the lower limit of the number of carbon atoms in the alkylene group is 2. ２３ The number of carbon atoms in the alkyl group of R is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of compound 1. ２４ The number of carbon atoms in the alkyl group of R is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of ease of production of compound 1. ２４ The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of excellent storage stability of Compound 1. p is preferably 0 or 1.

[0083] L １２ is a hydrocarbon group which may have a single bond or -O-. Examples of the hydrocarbon group include an aliphatic hydrocarbon group (which may be saturated or unsaturated, and may be linear, branched, or cyclic), an aromatic hydrocarbon group, and a group formed by combining these. From the viewpoint of excellent durability as a surface layer, an aliphatic hydrocarbon group is preferred, a saturated aliphatic hydrocarbon group is more preferred, and an alkylene group is even more preferred. １２ In the case where there are multiple L １２ may be the same or different. １２ The number of carbon atoms in the hydrocarbon group in is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 11. When the hydrocarbon group has 3 or more carbon atoms, the hydrocarbon group having 3 or more carbon atoms may be linear or may have a branched or cyclic structure. In the hydrocarbon group having -O-, L１１ The atom bonded to may be —O—, or there may be —O— between carbon atoms.

[0084] L １２ is preferably a group represented by the following formula (H1): *-(O) ａ４ - (L ｇ１１ O) ａ５ -L ｇ１２ -** (H1) where L ｇ１１ is an alkylene group having 1 to 12 carbon atoms, and L ｇ１１ If there are multiple L ｇ１１ may be the same or different, L ｇ１２ represents an alkylene group having 1 to 12 carbon atoms, a4 represents 0 or 1, a5 represents an integer of 0 or more, * represents L １１ is a bond bonded to T １ is the bond that bonds to

[0085] When a4 is 0, the atom having the bond * is a carbon atom, and when a4 is 1, the atom having the bond * is an oxygen atom. In Compound 1, a4 may be either 0 or 1 and may be appropriately selected from the viewpoint of ease of synthesis, etc. ｇ１１ It is the number of repetitions of O, and is preferably 0 to 6, more preferably 0 to 3, and even more preferably 0 to 1, from the viewpoint of excellent durability as a surface layer. ｇ１１ The alkylene group in may be a linear or branched alkylene group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably an alkylene group having 1 to 3 carbon atoms. The alkylene group is preferably a linear alkylene group. ｇ１２ The alkylene group may be a linear or branched alkylene group having 1 to 12 carbon atoms, and the alkylene group is preferably a linear alkylene group.

[0086] L ３１is a single bond or an (n1+1)-valent hydrocarbon group which may have -O-. Examples of the (n1+1)-valent hydrocarbon group include an aliphatic hydrocarbon group (which may be saturated or unsaturated, and may be linear, branched, or cyclic), an aromatic hydrocarbon group, and a group formed by combining these. From the viewpoint of ease of synthesis, an aliphatic hydrocarbon group is preferred, and a saturated aliphatic hydrocarbon group is more preferred. The number of carbon atoms in the (n1+1)-valent hydrocarbon group is preferably 1 to 20. The number of carbon atoms in the (n1+1)-valent hydrocarbon group may be 1 to 10, 1 to 6, or 1 to 4.

[0087] L ３１ is a divalent group, １２ and preferably has the same structure as the group represented by formula (H1). ３１ In formula (H1), ** is R ｆ * is a bond bonded to L ３２ Except for this, the symbols in formula (H1) are as described above, and the preferred embodiments are also the same.

[0088] L ３１ When L is a trivalent or higher valent group, １１ The examples are the same as those of formula (E1), formula (E2), and formula (E4) in the above formula. However, the symbols are to be read as follows: E １ or E ３ The L side of formula (1-1) ３２ Connect with E ２２ , E ２３ , E ２４ or E ２５ Side is R ｆ Connect to E １ is a single bond or —O—, ３ Is E １ and E １１ represents a single bond, —O—, an alkylene group, or an alkylene group having two or more carbon atoms and having —O— between carbon atoms, ２２ represents a single bond, an alkylene group, or an alkylene group having two or more carbon atoms and having —O— between carbon atoms, ２４Is E ２２ and Z １ Is E ３ has a carbon atom directly bonded to it and E ２４ is a group having an (e4+1)-valent carbocyclic ring structure having a carbon atom to which R is directly bonded, Ｅ１ is a hydrogen atom or an alkyl group, and R Ｅ１ When there are two or more R Ｅ１ may be the same or different, R Ｅ２ is a hydrogen atom or an alkyl group, e1 is an integer of 0 to 2, e2 is an integer of 0 to 3, and e1+e2 is an integer of 1 to 5, e3 is an integer of 1 to 3, e4 is an integer of 1 or more, and e5 is an integer of 1 to 3. Note that e1+e2=n1, e3=n1, e4=n1, and e5+1=n1.

[0089] L ３２ represents N, C, Si, or a cyclic hydrocarbon group which may contain an oxygen atom or a nitrogen atom as a ring member atom, and constitutes a branch point. ３２ The definition of is the same as that of the above L, except that it is limited to a cyclic hydrocarbon group whose ring structure may contain oxygen atoms or nitrogen atoms as ring members. ３ The branch point P explained in １ It is synonymous with L. ３２ The ring structure in ３ Examples of the structure include the same as those listed in the above, such as a 3- to 8-membered aliphatic ring, a 6-membered aromatic hydrocarbon ring, a 3- to 8-membered aliphatic heterocycle containing an oxygen atom or a nitrogen atom as a ring member, a 5- to 6-membered aromatic heterocycle containing an oxygen atom or a nitrogen atom as a ring member, and a fused ring consisting of two or more of these rings. ３ Examples of the ring structure constituting the ring structure include the following: In the ring structures exemplified below, one of the hydrogen atoms is L ４ The n2 bonds are L ３１ The hydrogen atoms are bonds to the side, and one or more of the remaining hydrogen atoms may be substituted with a fluorine atom.

[0090]

[0091] R１１ is a hydrogen atom or an alkyl group which may have —O—. １１ The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. When the alkyl group has 3 or more carbon atoms, the alkyl group having 3 or more carbon atoms may be linear or may have a branched or cyclic structure.

[0092] n1 is an integer of 1 or more, preferably 1 to 3, and more preferably 1 to 2. n2 is an integer of 2 or more, preferably 2 to 10, and more preferably 2 to 4. n3 is an integer of 0 or more, preferably 0 to 4, and more preferably 0 to 1. However, L ３２ is N, n2 is 2 and n3 is 0. ３２ is C or Si, then n2+n3 is 3.

[0093] Specific examples of compound 1-1 include compounds represented by the following formula: In the formula, L represents -L in formula (1-1). １１ - (L １２ -T １ ) ｘ１ Represents.

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] <Physical Properties of Compound 1> The molecular weight of Compound 1 is preferably 300 to 10,000, more preferably 300 to 5,000, and even more preferably 300 to 2,000. When the molecular weight of Compound 1 is equal to or greater than the lower limit of the above range, the abrasion resistance of the surface layer is superior. When the molecular weight of Compound 1 is equal to or less than the upper limit of the above range, the viscosity can be easily adjusted within an appropriate range, and the solubility is improved, resulting in excellent handleability during film formation.

[0106] [Surface Treatment Agent] The surface treatment agent of the present invention (hereinafter referred to as "the present surface treatment agent") contains Compound 1. The present surface treatment agent is suitable for applications requiring long-term maintenance of the performance of preventing a decrease in water and oil repellency even when the surface layer is repeatedly rubbed with fingers (abrasion resistance) and the performance of easily removing fingerprints attached to the surface layer by wiping (fingerprint stain removability), such as for components constituting the surface of a touch panel that is touched by fingers, eyeglass lenses, and displays of wearable devices. Furthermore, because the present surface treatment agent has excellent slip resistance, it is also suitable for use in glass-coated housings of mobile devices such as smartphones and tablet terminals. The present surface treatment agent is also suitable for use as an antifouling coating agent or a waterproof coating agent.

[0107] The present surface treatment agent may further contain a liquid medium. In the following description, the present surface treatment agent containing a liquid medium may be referred to as a coating liquid. The coating liquid may be in a liquid state, and may be a solution or a dispersion. The coating liquid may contain compound 1, and may also contain impurities such as by-products generated in the manufacturing process of compound 1. The concentration of compound 1 in the coating liquid 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.

[0108] As the liquid medium, an organic solvent is preferred. The organic solvent may be a fluorine-containing organic solvent, a non-fluorine-containing organic solvent, or a mixture of both. Specific examples of fluorine-containing organic solvents include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, fluoroalcohols, and hydrofluoroolefins (HFOs). As the fluorinated alkane, a compound having 4 to 8 carbon atoms is preferred. Specific examples of commercially available products include C ６ F １３ H (manufactured by AGC, Asahiklin (registered trademark) AC-2000), C ６ F １３ C ２ H ５ (AGC, Asahiklin (registered trademark) AC-6000), C ２ F ５ CHFCHFCF ３ (Vertrel (registered trademark) XF, manufactured by Chemours). Specific examples of fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene. As the fluoroalkyl ether, a compound having 4 to 12 carbon atoms is preferred. Specific examples of commercially available products include CF ３ CH ２ OCF ２ CF ２ H (manufactured by AGC, Asahiklin (registered trademark) AE-3000), C ４ F ９ OCH ３ (3M Novec (registered trademark) 7100), C ４ F ９ O.C. ２ H ５ (3M Novec (registered trademark) 7200), C ２ F ５ CF (OCH ３ ) C ３ F ７(Novec (registered trademark) 7300, manufactured by 3M Corporation). Specific examples of fluorinated alkylamines include perfluorotripropylamine and perfluorotributylamine. Specific examples of fluoroalcohols include 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol. Specific examples of HFOs include 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (Amorea (registered trademark) AS-300, manufactured by AGC Corporation). Preferred non-fluorinated organic solvents are compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms, and examples of such organic solvents include hydrocarbon organic solvents, alcohol organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, and glycol organic solvents.

[0109] 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.

[0110] 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.

[0111] Specific examples of the ketone organic solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, and 3,3,5-trimethylcyclohexanone, and isophorone.

[0112] Specific examples of the ether-based organic solvent include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.

[0113] Specific examples of the ester-based organic solvent 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, and ethylene glycol monoethyl ether acetate. ester, ethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monopropyl ether acetate, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.

[0114] 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, and dipropylene glycol monobutyl. ether, dipropylene 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, triethylene glycol dimethyl ether, and polyethylene glycol dimethyl ether.

[0115] Other organic solvents include chlorine-based organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds.

[0116] Specific examples of chlorine-based organic solvents include dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0117] Specific examples of the nitrogen-containing compound include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0118] Specific examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0119] Specific examples of the siloxane compound include hexamethyldisiloxane, octamethyltrisiloxane, and decamethyltetrasiloxane.

[0120] The coating liquid preferably contains 75 to 99.999 mass %, more preferably 85 to 99.99 mass %, and even more preferably 90 to 99.9 mass % of the liquid medium.

[0121] The present surface treatment agent may contain other components in addition to Compound 1 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 present surface treatment agent is preferably 10% by mass or less, more preferably 1% by mass or less.

[0122] The total concentration of Compound 1 and other components in the coating liquid (hereinafter referred to as "solids concentration") is preferably 0.001 to 40 mass%, more preferably 0.01 to 20 mass%, even more preferably 0.01 to 10 mass%, and particularly preferably 0.01 to 1 mass%. The solids concentration of the coating liquid is a value calculated from the mass of the coating liquid before heating and the mass after heating for 4 hours in a convection dryer at 120°C.

[0123] [Article] The article of the present invention (hereinafter referred to as "the article") has a surface layer formed from Compound 1 or the surface treatment agent on the surface of a substrate. An example of the article will be described with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing a first article, which is an example of the article. The first article is an article 20 having a substrate 12, an underlayer 14, and a surface layer 22 in this order, in which the underlayer 14 contains an oxide containing silicon, and the surface layer 22 contains a condensate of Compound 1.

[0124] The material and shape of the substrate 12 may be appropriately selected depending on the application of the article 20. Examples of materials for the substrate 12 include glass, resin, sapphire, metal, ceramic, stone, and composite materials thereof. Glass may be chemically strengthened. In particular, examples of substrates 12 that require water and oil repellency include substrates for touch panels, substrates for displays, and substrates that form the housings of electronic devices. Touch panel substrates and display substrates are translucent. "Translucent" means that the normal incidence visible light transmittance in accordance with JIS R3106:1998 (ISO 9050:1990) is 25% or more. Glass or transparent resin is preferred as the material for the touch panel substrate.

[0125] The substrate 12 may be subjected to a surface treatment such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment on the surface on which the underlayer 14 is to be formed. The surface that has been subjected to the surface treatment further improves the adhesion between the substrate 12 and the underlayer 14, and as a result, further improves the abrasion resistance of the surface layer 22. As the surface treatment, corona discharge treatment or plasma treatment is preferred because it further improves the abrasion resistance of the surface layer 22.

[0126] The underlayer 14 is a layer containing at least an oxide containing silicon, and may further contain other elements. When the underlayer 14 contains silicon oxide, the T of Compound 1 １ is dehydrated and condensed to form Si—O—Si bonds with the underlayer 14, forming a surface layer 22 with superior abrasion resistance.

[0127] The content of silicon oxide in the underlayer 14 is preferably 65% ​​by mass or more, more preferably 80% by mass or more, even more preferably 85% by mass or more, and particularly preferably 90% by mass or more. When the content of silicon oxide is equal to or greater than the lower limit of the above range, Si—O—Si bonds are sufficiently formed in the underlayer 14, and the mechanical properties of the underlayer 14 are sufficiently ensured. The content of silicon oxide is the remainder obtained by subtracting the total content of other elements (in the case of oxides, the amount converted into oxide) from the mass of the underlayer 14.

[0128] In order to improve the durability of the surface layer 22, it is preferable that the oxide in the underlayer 14 further contains one or more elements selected from alkali metal elements, alkaline earth metal elements, platinum group elements, boron, aluminum, phosphorus, titanium, zirconium, iron, nickel, chromium, molybdenum, and tungsten. The inclusion of these elements strengthens the bond between the underlayer 14 and the compound 1, improving the abrasion resistance.

[0129] When the underlayer 14 contains one or more elements selected from iron, nickel, and chromium, the total content of these elements relative to silicon oxide is preferably 10 to 1,100 ppm by mass, more preferably 50 to 1,100 ppm by mass, even more preferably 50 to 500 ppm by mass, and particularly preferably 50 to 250 ppm by mass. When the underlayer 14 contains one or more elements selected from aluminum and zirconium, the total content of these elements is preferably 10 to 2,500 ppm by mass, more preferably 15 to 2,000 ppm by mass, and even more preferably 20 to 1,000 ppm by mass. When the underlayer 14 contains an alkali metal element, the total content of these elements is preferably 0.05 to 15% by mass, more preferably 0.1 to 13% by mass, and even more preferably 1.0 to 10% by mass. Examples of alkali metal elements include lithium, sodium, potassium, rubidium, and cesium. When the underlayer 14 contains platinum group elements, the total content thereof is preferably 0.02 to 800 ppm by mass, more preferably 0.04 to 600 ppm by mass, and even more preferably 0.7 to 200 ppm by mass. Examples of platinum group elements include platinum, rhodium, ruthenium, palladium, osmium, and iridium. When the underlayer 14 contains one or more elements selected from boron and phosphorus, the total content thereof is preferably 0.003 to 9, more preferably 0.003 to 2, and even more preferably 0.003 to 0.5, in terms of the ratio of the molar concentration of the sum of boron and phosphorus to the molar concentration of silicon, in order to provide excellent abrasion resistance to the surface layer 22. When the underlayer 14 contains alkaline earth metal elements, the total content thereof is preferably 0.005 to 5, more preferably 0.005 to 2, and even more preferably 0.007 to 2, in terms of the ratio of the molar concentration of the total alkaline earth metal elements to the molar concentration of silicon, in order to provide excellent abrasion resistance to the surface layer 22. Examples of alkaline earth metal elements include calcium, strontium, barium, and magnesium.

[0130] From the viewpoint of improving the adhesiveness of the present surface treatment agent and improving the water / oil repellency and abrasion resistance of the article 20, the underlayer 14 is preferably a silicon oxide layer containing alkali metal atoms. In the silicon oxide layer, the average concentration of alkali metal atoms in a region 0.1 to 0.3 nm deep from the surface in contact with the surface layer 22 is 2.0×10 １９ atoms / cm ３ On the other hand, in order to ensure sufficient mechanical properties of the silicon oxide layer, the average concentration of alkali metal atoms is preferably 4.0×10 or more. ２２ atoms / cm ３ It is preferable that:

[0131] The thickness of the underlayer 14 is preferably 1 to 200 nm, and more preferably 2 to 20 nm. If the thickness of the underlayer 14 is equal to or greater than the lower limit of the above range, the underlayer 14 is likely to have a sufficient effect of improving adhesion. If the thickness of the underlayer 14 is equal to or less than the upper limit of the above range, the abrasion resistance of the underlayer 14 itself is increased. Methods for measuring the thickness of the underlayer 14 include a method of observing the cross section of the underlayer 14 using an electron microscope (SEM, TEM, etc.), and a method using an optical interference film thickness meter, a spectroscopic ellipsometer, a step gauge, etc.

[0132] A specific example of a method for forming the underlayer 14 is a method in which a vapor deposition material having the desired composition of the underlayer 14 is vapor-deposited on the surface of the substrate 12. Vacuum vapor deposition is one example of a vapor deposition method. Vacuum vapor deposition is a method in which the vapor deposition material is evaporated in a vacuum chamber and attached to the surface of the substrate 12. The temperature during vapor deposition (e.g., the temperature of the boat in which the vapor deposition material is placed when using a vacuum vapor deposition apparatus) is preferably 100 to 3,000°C, more preferably 500 to 3,000°C. The pressure during vapor deposition (e.g., the absolute pressure in the chamber in which the vapor deposition material is placed when using a vacuum vapor deposition apparatus) is preferably 1 Pa or less, more preferably 0.1 Pa or less. When forming the underlayer 14 using a vapor deposition material, a single vapor deposition material may be used, or two or more vapor deposition materials containing different elements may be used. Examples of vapor deposition material evaporation methods include a resistance heating method in which the vapor 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 an electron beam is irradiated onto the vapor deposition material to directly heat the vapor deposition material and melt and evaporate the surface. The electron gun method is preferred as a method for evaporating the deposition material because it can evaporate high-melting-point substances because it can heat locally, and because areas not irradiated by the electron beam are at low temperatures, there is no risk of reaction with the container or contamination with impurities. The deposition material used in the electron gun method is preferably a molten granular material or a sintered material because it is less likely to scatter even when an air current is generated.

[0133] The surface layer 22 on the underlayer 14 contains a condensate of Compound 1. Condensates of Compound 1 include those formed by hydrolysis of hydrolyzable silyl groups in Compound 1 to form silanol groups (Si—OH), which then undergo an intermolecular condensation reaction to form Si—O—Si bonds, and those formed by condensation of silanol groups in Compound 1 with silanol groups or Si—OM groups (where M is an alkali metal element) on the surface of the underlayer 14 to form Si—O—Si bonds. Furthermore, the surface layer 22 may contain a condensate of a compound other than Compound 1 contained in the surface treatment agent. The surface layer 22 may contain a compound having a reactive silyl group in a state in which some or all of the reactive silyl groups of the compound have undergone condensation reaction.

[0134] The thickness of the surface layer 22 is preferably 1 to 100 nm, and more preferably 1 to 50 nm. When the thickness of the surface layer 22 is equal to or greater than the lower limit of the above range, the effect of the surface layer 22 can be sufficiently obtained. When the thickness of the surface layer 22 is equal to or less than the upper limit of the above range, the utilization efficiency is high. The thickness of the surface layer 22 is a thickness obtained using an X-ray diffractometer for thin film analysis. The thickness of the surface layer 22 can be calculated from the oscillation period of the interference pattern obtained by X-ray reflectivity method using an X-ray diffractometer for thin film analysis.

[0135] Another example of the article of the present invention is article 20. The second article is article 20 having substrate 10 with an undercoat layer and surface layer 22 in this order, in which substrate 10 with an undercoat layer contains an oxide containing silicon, and surface layer 22 contains a condensate of Compound 1.

[0136] In the second article, the base layer-attached substrate 10 has the same composition as the base layer 14 in the first article, and therefore the surface layer 22 has excellent abrasion resistance even when the surface layer 22 is formed directly on the base layer-attached substrate 10. The material of the base layer-attached substrate 10 in the second article may be any material as long as it has the composition of the base layer 14, and may be, for example, a glass substrate. Details of the material of the base layer-attached substrate 10 are the same as the materials of the substrate 12 and the base layer 14, and therefore will not be described here. The configuration of the surface layer 22 is also the same as that of the first article, and therefore will not be described here.

[0137] Specific examples of the article of the present invention include optical members, touch panels, anti-reflection films, anti-reflection glass, and SiO ２ Examples include treated glass, tempered glass, sapphire glass, quartz substrates, and mold metals.Products: car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (gastroscopes, etc.), copiers, personal computers (PCs), liquid crystal displays, organic electroluminescent displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc.

[0138] [Method for Producing an Article] The method for producing an article of the present invention is a method for forming a surface layer by a dry coating method or a wet coating method using Compound 1 or the present surface treatment agent.

[0139] Compound 1 and the present surface treatment agent can be used directly in a dry coating method and are suitable for forming a surface layer with excellent adhesion by the dry coating method. Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferred in terms of suppressing decomposition of the present surface treatment agent and simplifying the equipment. For vacuum deposition, a pellet-shaped material in which compound 1 or the like is supported on a porous metal body made of a metal material such as iron or steel may be used. The pellet-shaped material in which compound 1 or the like is supported can be produced by impregnating a porous metal body with a solution containing compound 1, drying it, and removing the liquid medium.

[0140] The present surface treatment agent (coating liquid) containing a liquid medium can be suitably used in wet coating methods, such as 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.

[0141] In order to improve the abrasion resistance of the surface layer, an operation for promoting the reaction between Compound 1 and the substrate may be performed as necessary. Examples of such an operation include heating, humidification, and light irradiation. For example, the substrate on which the surface layer has been formed can be heated in a humid atmosphere to 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 the condensation reaction of silanol groups. After the surface treatment, compounds in the surface layer that are not chemically bonded to other compounds or the substrate may be removed as needed. Specific methods include, for example, pouring a solvent over the surface layer and wiping with a cloth soaked in the solvent.

[0142] The present invention will be described in detail below with reference to examples. Among Examples 1 to 15, Examples 1 to 5 and 7 to 15 are working examples, and Example 6 is a comparative example. However, the present invention is not limited to these examples.

[0143] [Example 1] <Synthesis of Compound A> Under a nitrogen atmosphere, pentaerythritol monobenzyl ether (1.0 g), silver trifluoromethanesulfonate (17 g), cesium fluoride (12 g), Selectfluor (registered trademark, manufactured by Tokyo Chemical Industry Co., Ltd., 19 g), 2-fluoropyridine (5.7 mL), and dry toluene (100 mL) were added to a flask in a glove box and stirred at 25°C for 10 minutes. Next, with stirring, (trifluoromethyl)trimethylsilane (9.8 mL) was added dropwise over 5 minutes, and the mixture was stirred at 25°C for an additional 15 hours. After the reaction, the resulting precipitate was filtered off using Celite, the residue was washed with hexane, and the low-boiling components of the obtained filtrate were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane) to obtain 1.0 g of Compound A. The structure of Compound A was confirmed by the following NMR data.

[0144]

[0145] (NMR spectrum of compound A) 1 H-NMR (400MHz, CDCl3) δ 7.39 - 7.28 (m, 5H), 4.52 (s, 2H), 4.04 (s, 6H), 3.49 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-62.9.

[0146] <Synthesis of Compound B> Compound A (1.0 g) and methanol (15 mL) were added to a recovery flask and stirred at 25°C until homogenous. Next, 10% palladium carbon (1.0 g) was added, and the gas in the flask was replaced with a hydrogen atmosphere. The reaction suspension was stirred at 25°C for 15 hours, and then the precipitate was removed by passing it through Celite. Low-boiling point components of the obtained filtrate were distilled off under reduced pressure, and the obtained crude liquid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 760 mg of compound B. The structure of compound B was confirmed by the following NMR data.

[0147]

[0148] (NMR spectrum of compound B) 1 H-NMR (400MHz, CDCl3) δ4.05 (s, 6H), 3.74 (d, J = 5.0 Hz, 2H), 1.63 (t, J = 5.0 Hz, 1H). 19 F-NMR (376MHz, CDCl3) δ-62.9.

[0149] <Synthesis of Compound C> Under a nitrogen atmosphere, dried dimethylformamide (10 mL) and 60% sodium hydride (dispersed in liquid paraffin, 110 mg) were added to Compound B (270 mg) and stirred at 25°C for 10 minutes. Thereafter, 18-iodo-1-octadecene (980 mg) was added, and the mixture was stirred at 25°C for an additional 15 hours. Next, water was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The low-boiling components were distilled off under reduced pressure, and the resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane) to obtain 190 mg of Compound C. The structure of Compound C was confirmed by the following NMR data.

[0150]

[0151] (NMR spectrum of compound C) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 4.02 (s, 6H), 3.43 - 3.40 (m, 4H), 2.07 - 2.01 (m, 2H), 1.56 - 1.51 (m, 2H), 1.39 - 1.26 (m, 26H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0152] <Synthesis of Compound 1-1A> A toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (0.3 mg), and trimethoxysilane (58 mg) were added to compound C (190 mg) dissolved in dichloromethane (1 mL), and the mixture was stirred at 25°C for 2 hours. The solvent was removed by distillation under reduced pressure, yielding 230 mg of compound 1-1A. The structure of compound 1-1A was confirmed by the following NMR data.

[0153]

[0154] (NMR spectrum of compound 1-1A) 1 H-NMR (400MHz, CDCl3) δ4.02 (s, 6H), 3.57 (s, 9H), 3.43 - 3.40 (m, 4H), 1.57 - 1.51 (m, 2H), 1.44 - 1.25 (m, 30H), 0.66 - 0.62 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.7.

[0155] Example 2 Synthesis of Compound D A Grignard reagent prepared from 18-bromo-1-octadecene (1.9 g), magnesium (640 mg), and dry THF (tetrahydrofuran, 50 mL) was cooled to -10°C, and copper iodide (560 mg) was added. The mixture was stirred for 15 minutes, and then tert-butyldimethylsilyl glycidyl ether (970 mg) was added dropwise. The reaction solution was then heated to 0°C and stirred for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction solution, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting residue (2.0 g) was used as a crude product in the subsequent reaction. The crude product contained Compound D.

[0156]

[0157] <Synthesis of Compound E> A crude product (2.0 g) containing Compound D was dissolved in THF (10 mL) and cooled to 0°C, followed by dropwise addition of a THF solution (1.0 mol / L, 6 mL) of tetrabutylammonium fluoride. After stirring the mixture for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction solution, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 520 mg of Compound E. The structure of Compound E was confirmed by the following NMR data.

[0158] (NMR spectrum of compound E) 1 H-NMR (400MHz, CDCl3) δ 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.03 - 4.92 (m, 2H), 3.74 - 3.65 (m, 2H), 3.48 - 3.42 (m, 1H), 2.07 - 2.02 (m, 2H), 1.97 (d, J = 4.3 Hz, 1H), 1.83 (t, J = 6.0 Hz, 1H), 1.45 - 1.26 (m, 32H).

[0159]

[0160] <Synthesis of Compound F> Under a nitrogen atmosphere, compound E (1.2 g), silver trifluoromethanesulfonate (7.2 g), cesium fluoride (6.4 g), Selectfluor (registered trademark, manufactured by Tokyo Chemical Industry Co., Ltd., 19 g), 2-fluoropyridine (2.4 mL), and dry toluene (30 mL) were added to a 100 mL flask in a glove box and stirred at 25°C for 10 minutes. Next, while stirring, (trifluoromethyl)trimethylsilane (4.2 mL) was added dropwise over 5 minutes, and the mixture was stirred at 25°C for an additional 15 hours. After the reaction, the resulting precipitate was filtered off using Celite, the residue was washed with hexane, and the low-boiling components of the obtained filtrate were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane) to obtain 400 mg of compound F. The structure of compound F was confirmed by the following NMR data.

[0161]

[0162] (NMR spectrum of compound F) 1 H-NMR (400MHz, CDCl3) δ5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.4 Hz, 1H), 5.02 - 4.91 (m, 2H), 4.38 - 4.32 (m, 1H), 4.02 (d, J = 4.8 Hz, 2H), 2.06 - 2.01 (m, 2H), 1.73 - 1.64 (m, 2H), 1.45 - 1.26 (m, 30H). 19 F-NMR (376MHz, CDCl3) δ-58.4 (s), -61.2 (s).

[0163] <Synthesis of Compound 1-1B> 420 mg of compound 1-1B was obtained in the same manner as in the synthesis procedure for compound 1-1A, except that compound F (330 mg) was used instead of compound C. The structure of compound 1-1B was confirmed by the following NMR data.

[0164]

[0165] (NMR spectrum of compound 1-1B) 1H-NMR (400MHz, CDCl3) δ4.38 - 4.32 (m, 1H), 4.02 (d, J = 4.8 Hz, 2H), 3.56 (s, 9H), 1.73 - 1.64 (m, 2H), 1.42 - 1.25 (m, 34H), 0.67 - 0.62 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-58.4 (s), -61.2 (s).

[0166] [Example 3] <Synthesis of Compound G> Under a nitrogen atmosphere, dry dimethylformamide (50 mL) and 60% sodium hydride (dispersed in liquid paraffin, 1.4 g) were added to 2-phenyl-1,3-dioxan-5-ol (2.5 g) and stirred at 25°C for 10 minutes. Then, 18-bromo-1-octadecene (9.2 g) was added, and the mixture was stirred for an additional 2 hours at 25°C. Next, water was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The low-boiling components were distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), yielding 6.0 g of Compound G. The structure of Compound G was confirmed by the following NMR data.

[0167]

[0168] (NMR spectrum of compound G) 1H-NMR (400MHz, CDCl3) δ7.52 - 7.50 (m, 2H), 7.37 - 7.32 (m, 3H), 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.55 (s, 1H), 5.02 - 4.91 (m, 2H), 4.34 (dd, J = 12.4 Hz, 1.2 Hz, 2H), 4.05 (dd, J = 12.4 Hz, 1.4 Hz, 2H), 3.55 (t, J = 6.9 Hz, 2H), 3.27 - 3.25 (m, 1H), 2.06 - 2.01 (m, 2H), 1.68 - 1.61 (m, 2H), 1.39 - 1.24 (m, 26H).

[0169] <Synthesis of Compound H> Compound G (6.0 g) was dispersed in methanol (100 mL), p-toluenesulfonic acid monohydrate (1.5 g) was added, and the mixture was stirred at 25°C for 6 hours. Next, a saturated aqueous solution of sodium bicarbonate was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The low-boiling components were distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), yielding 4.2 g of Compound H. The structure of Compound H was confirmed by the following NMR data.

[0170]

[0171] (NMR spectrum of compound H) 1 H-NMR (400MHz, CDCl3) δ5.81 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.80 - 3.65 (m, 4H), 3.57 (t, J = 6.7 Hz, 2H), 3.46 (quint, J = 5.0 Hz, 1H), 2.07 - 2.01 (m, 2H), 1.93 (d, J = 6.0 Hz, 2H), 1.63 - 1.56 (m, 2H), 1.39 - 1.25 (m, 26H).

[0172] <Synthesis of Compound J> 460 mg of Compound J was obtained in the same manner as in the synthesis procedure of Compound F, except that Compound H (1.0 g) was used instead of Compound E. The structure of Compound J was confirmed by the following NMR data.

[0173] (NMR spectrum of compound J) 1 H-NMR (400MHz, CDCl3) δ5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.0 Hz, 1H), 3.57 (t, J = 6.4 Hz, 2H), 2.06 - 2.01 (m, 2H), 1.61 - 1.52 (m, 2H), 1.39 - 1.22 (m, 26H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0174]

[0175] <Synthesis of Compound 1-1C> 550 mg of compound 1-1C was obtained in the same manner as in the synthesis procedure of compound 1-1A, except that compound J (460 mg) was used instead of compound C. The structure of compound 1-1C was confirmed by the following NMR data.

[0176]

[0177] (NMR spectrum of compound 1-1C) 1 H-NMR (400 MHz, CDCl3) δ4.07 - 3.99 (m, 4H), 3.74 (quint, J = 5.3 Hz, 1H), 3.59 - 3.56 (m, 11H), 1.61 - 1.54 (m, 2H), 1.41 - 1.25 (m, 30H), 0.67 - 0.63 (m, 2H). 19 F-NMR (376 MHz, CDCl3) δ-61.2.

[0178] Example 4 Synthesis of Compound K Under a nitrogen atmosphere, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 5.3 mg) and dichloromethylsilane (72 mg) were added to compound J (200 mg) dissolved in dry dichloromethane (1 mL), and the mixture was stirred at 25°C for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was dissolved in dry THF (10 mL). A THF solution of allyl magnesium chloride (2.0 mol / L, 0.8 mL) was added dropwise, and the mixture was stirred at 25°C for 1.5 hours. Next, a saturated aqueous ammonium chloride solution was added to the solution, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and saturated saline and dried over magnesium sulfate, and then the solvent and low-boiling components were evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), yielding 130 mg of compound K. The structure of Compound K was confirmed by the following NMR data.

[0179]

[0180] (NMR spectrum of compound K) 1 H-NMR (400MHz, CDCl3) δ5.83 - 5.72 (m, 2H), 4.88- 4.82 (m, 4H), 4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.3 Hz, 1H), 3.57 (t, d = 6.7 Hz, 2H), 1.61 - 1.53 (m, 6H), 1.34 - 1.25 (m, 30H), 0.56 - 0.52 (m, 2H), -0.08 (s, 3H). 19 F-NMR (376MHz, CDCl3) δ-61.2.

[0181] <Synthesis of Compound 1-1D> 180 mg of compound 1-1D was obtained in the same manner as in the synthesis procedure for compound 1-1A, except that compound K (130 mg) was used instead of compound C. The structure of compound 1-1D was confirmed by the following NMR data.

[0182]

[0183] (NMR spectrum of compound 1-1D) 1 H-NMR (400MHz, CDCl3) δ 4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.0 Hz, 1H), 3.59 - 3.56 (m, 20H), 1.61 - 1.52 (m, 2H), 1.45 - 1.40 (m, 4H), 1.32 - 1.25 (m, 30H), 0.73 - 0.69 (m, 4H), 0.60 - 0.56 (m, 4H), 0.49 - 0.45 (m, 2H), -0.03 (s, 3H). 19 F-NMR (376MHz, CDCl3) δ-61.2.

[0184] [Example 5] <Synthesis of Compound L> Under a nitrogen atmosphere, dry dimethylformamide (50 mL), dry THF (50 mL), and 60% sodium hydride (dispersed in liquid paraffin, 0.75 g) were added to dimethyl malonate (3.0 g) and stirred at 25°C for 10 minutes. Then, 18-bromo-1-octadecene (5.0 g) was added, and the mixture was heated to 60°C and stirred for 5 hours. Water was then added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate. The solvent and low-boiling components were then distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), yielding 5.8 g of Compound L. The structure of Compound L was confirmed by the following NMR data.

[0185]

[0186] (NMR spectrum of compound L) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.74 (s, 6H), 3.36 (t, J = 7.6 Hz, 1H), 2.06 - 2.01 (m, 2H), 1.92 -1.86 (m,2H), 1.39 - 1.25 (m, 28H).

[0187] <Synthesis of Compound M> Under a nitrogen atmosphere, lithium aluminum hydride (0.62 g) and dry THF (10 mL) were mixed, and the resulting suspension was cooled to 0°C. Next, compound L (2.5 g) dissolved in dry THF (15 mL) was added dropwise, and the mixture was stirred at 0°C for 15 minutes. The temperature was then raised to 25°C, and the mixture was stirred for an additional 2 hours. Next, the reaction solution was cooled again to 0°C, and saturated aqueous sodium sulfate solution was added dropwise to terminate the reaction. The resulting precipitate was filtered through Celite, the residue was washed with THF, and the low-boiling components of the obtained filtrate were distilled off under reduced pressure. The resulting solid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), yielding 1.5 g of compound M. The structure of compound M was confirmed by the following NMR data.

[0188]

[0189] (NMR spectrum of compound M) 1 H-NMR (400MHz, CDCl3) δ5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.85 - 3.80 (m, 2H), 3.69 - 3.63 (m, 2H), 2.11 (t, J = 5.5 Hz, 2H), 2.06 - 2.01 (m, 2H), 1.81 - 1.74 (m, 1H), 1.39 - 1.21 (m, 30H).

[0190] <Synthesis of Compound N> 450 mg of Compound N was obtained in the same manner as in the synthesis procedure of Compound F, except that Compound M (1.4 g) was used instead of Compound E. The structure of Compound N was confirmed by the following NMR data.

[0191]

[0192] (NMR spectrum of compound N) 1H-NMR (400MHz, CDCl3) δ5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 2.06 - 2.01 (m, 3H), 1.41 - 1.26 (m, 30H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0193] <Synthesis of Compound 1-1E> 220 mg of compound 1-1E was obtained in the same manner as in the synthesis procedure for compound 1-1A, except that compound N (180 mg) was used instead of compound C. The structure of compound 1-1E was confirmed by the following NMR data.

[0194]

[0195] (NMR spectrum of compound 1-1E) 1 H-NMR (400MHz, CDCl3) δ3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.57 (s, 9H), 2.09 - 2.01 (m, 1H), 1.39 - 1.26 (m, 34H), 0.67 - 0.63 (m, 2H). 19 F-NMR (376 MHz, CDCl3) δ-61.1. [Example 6] n-Octadecyltrimethoxysilane described in WO 2008 / 016029 was designated as compound C1-1.

[0196] Example 7 Synthesis of Compound AA 180 mg of Compound AA was obtained in the same manner as in the synthesis of Compound K, except that Compound 1-1A (200 mg) was used instead of Compound J. The structure of Compound AA was confirmed by the following NMR data.

[0197]

[0198] (NMR spectrum of compound AA) 1H-NMR (400MHz, CDCl3) δ 5.83 - 5.73 (m, 2H), 4.88 - 4.81 (m, 4H), 4.02 (s, 6H), 3.43 - 3.40 (m, 4H), 1.56 - 1.52 (m, 6H), 1.30 - 1.25 (m, 30H), 0.56 - 0.52 (m, 2H), -0.03 (s, 3H). 19 F-NMR (376MHz, CDCl3) δ-62.9

[0199] <Synthesis of Compound 1-1F> 230 mg of Compound 1-1F was obtained in the same manner as in the synthesis procedure for Compound 1-1A, except that Compound AA (180 mg) was used instead of Compound C. The structure of Compound 1-1F was confirmed by the following NMR data.

[0200]

[0201] (NMR spectrum of compound 1-1F) 1 H-NMR (400MHz, CDCl3) δ 4.02 (s, 6H), 3.56 (s, 18H), 3.43 - 3.38 (m, 4H), 1.57 - 1.51 (m, 2H), 1.47 - 1.25 (m, 34H), 0.73 - 0.69 (m, 4H), 0.60 - 0.56 (m, 4H), 0.49 - 0.46 (m, 2H), -0.08 (s, 3H). 19 F-NMR (376MHz, CDCl3) δ-62.9.

[0202] Example 8 Synthesis of Compound AB To 10-undecenal (10 g), an aqueous formaldehyde solution (38% by mass, 47 g), ethanol (100 mL), and calcium oxide (4.7 g) were added, and the mixture was stirred at 37°C for 24 hours. The temperature was then raised to 60°C and the mixture was stirred for 2 hours. After the reaction, the mixture was neutralized using dry ice, and the volatile components were distilled off under reduced pressure. Methylene chloride (100 g) was added to the crude liquid, and the insoluble components were removed using Celite. The separated organic phase was washed with saturated saline and dried over magnesium sulfate, and the solvent and low-boiling components were then distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: methylene chloride / methanol), yielding 6.8 g of Compound AB. The structure of Compound AB was confirmed by the following NMR data.

[0203]

[0204] (NMR spectrum of compound AB) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.75 (d, J = 5.5 Hz, 6H), 2.44 (t, J = 5.5 Hz, 3H), 2.06 - 2.01 (m, 2H), 1.38 - 1.18 (m, 12H).

[0205] <Synthesis of Compound AC> Compound AC (1.2 g) was obtained in the same manner as in the synthesis of Compound A, except that Compound AB (2.0 g) was used instead of pentaerythritol monobenzyl ether. The structure of Compound AC was confirmed by the following NMR data.

[0206]

[0207] (NMR spectrum of compound AC) 1H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.03 - 4.92 (m, 2H), 3.91 (s, 6H), 2.07 - 2.02 (m, 2H), 1.50 - 1.28 (m, 12H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0208] <Synthesis of Compound AD> Under a nitrogen atmosphere, dry dichloromethane (5.0 mL) and zirconocene chloride hydride (400 mg) were added to Compound AC (600 mg), and the mixture was stirred at room temperature for 30 minutes. Thereafter, N-bromosuccinimide (730 mg) was added to the solution, and the mixture was stirred at room temperature for an additional 30 minutes. The reaction was terminated using an aqueous sodium thiosulfate solution, and hexane was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane) to obtain 700 mg of Compound AD. The structure of Compound AD was confirmed by the following NMR data.

[0209]

[0210] (NMR spectrum of compound AD) 1 H-NMR (400MHz, CDCl3) δ 3.90 (s, 6H), 3.41 (t, J = 6.9 Hz, 2H), 1.89 - 1.82 (m, 2H), 1.50 - 1.28 (m, 14H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0211] <Synthesis of Compound AE> Under a nitrogen atmosphere, 18-bromo-1-octadecene (1.0 g) and magnesium (70 mg) were stirred in dry tetrahydrofuran (3.0 mL) for 1 hour, and the solid components were then removed by filtration to obtain the corresponding Grignard reagent. Compound AD (700 mg) was dissolved in dry tetrahydrofuran (2.0 mL), copper(II) chloride (1.0 mg) was added, and the prepared Grignard reagent was added dropwise. The mixture was stirred at room temperature for 15 hours, and the reaction was terminated by adding an aqueous ammonium chloride solution. Hexane was added to the mixture, and the organic phase was separated. The organic phase was washed with water and saturated saline and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane) to obtain 620 mg of Compound AE. The structure of Compound AE was confirmed by the following NMR data.

[0212]

[0213] (NMR spectrum of compound AE) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.90 (s, 6H), 2.06 - 2.01 (m, 2H), 1.49 - 1.25 (m, 48H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0214] <Synthesis of Compound 1-1G> 730 mg of compound 1-1G was obtained in the same manner as in the synthesis procedure for compound 1-1A, except that compound AE (620 mg) was used instead of compound C. The structure of compound 1-1G was confirmed by the following NMR data.

[0215]

[0216] (NMR spectrum of compound 1-1G) 1H-NMR (400MHz, CDCl3) δ3.90 (s, 6H), 3.57 (s, 9H), 1.49 - 1.25 (m, 52H), 0.67 - 0.63 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0217] Example 9 Synthesis of Compound 1-1H 240 mg of Compound 1-1H was obtained in the same manner as in the synthesis of Compound 1-1A, except that Compound AE (200 mg) was used instead of Compound C and triethoxysilane (70 mg) was used instead of trimethoxysilane. The structure of Compound 1-1H was confirmed by the following NMR data.

[0218]

[0219] (NMR spectrum of compound 1-1H) 1 H-NMR (400MHz, CDCl3) δ 3.90 (s, 6H), 3.82 (q, J = 6.9 Hz, 6H), 1.49 - 1.25 (m, 61H), 0.65 - 0.61 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0220] [Example 10] <Synthesis of Compound AF> Under a nitrogen atmosphere, dry tetrahydrofuran (2.0 mL) and magnesium (60 mg) were added to Compound AD (600 mg) and stirred at room temperature for 1 hour. Then, dry ice pieces (2.0 g) were added to the solution, and the mixture was further stirred at room temperature for 1 hour. The reaction was terminated by adding 1N hydrochloric acid. Hexane was added to the mixture to separate the organic phase. The organic phase was washed with water and saturated saline and dried over magnesium sulfate, and then the solvent and low-boiling components were distilled off under reduced pressure. The crude reaction solution was then purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 320 mg of Compound AF. The structure of Compound AF was confirmed by the following NMR data.

[0221]

[0222] (NMR spectrum of compound AF) 1H-NMR (400MHz, CDCl3) δ 3.90 (s, 6H), 2.23 (t, J = 7.4 Hz, 2H), 1.68 - 1.25 (m, 16H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0223] <Synthesis of Compound AG> Under a nitrogen atmosphere, Compound AF (300 mg), dry tetrahydrofuran (2.0 mL), N,N-diisopropylethylamine (320 mg), 2-(undec-1-enyl)tridec-12-en-1-amine (440 mg), and propylphosphonic anhydride (1.7 M, 0.75 mL) were added and stirred at room temperature for 15 hours. Thereafter, 1N hydrochloric acid was added to the crude liquid, and the organic layer was separated using ethyl acetate. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 460 mg of Compound AG. The structure of Compound AG was confirmed by the following NMR data.

[0224]

[0225] (NMR spectrum of compound AG) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.31 (br, 1H), 5.02 - 4.91 (m, 4H), 3.90 (s, 6H), 3.19 - 3.16 (m, 2H), 2.16 (t, J = 7.4 Hz, 2H), 2.06 - 2.01 (m, 4H), 1.69 - 1.56 (m, 3H), 1.49 - 1.24 (m, 46H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0226] <Synthesis of Compound 1-1I> 600 mg of Compound 1-1I was obtained in the same manner as in the synthesis procedure for Compound 1-1A, except that Compound AG (460 mg) was used instead of Compound C. The structure of Compound 1-1I was confirmed by the following NMR data.

[0227]

[0228] (NMR spectrum of compound 1-1I) 1 H-NMR (400MHz, CDCl3) δ 5.30 (br, 1H), 3.90 (s, 6H), 3.57 (s, 18H), 3.19 - 3.16 (m, 2H), 2.16 (t, J = 7.4 Hz, 2H), 1.69 - 1.56 (m, 3H), 1.44 - 1.25 (m, 54H), 0.66 - 0.62 (m, 4H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0229] [Example 11] <Synthesis of Compound AH> 620 mg of Compound AH was obtained in the same manner as in the synthesis of Compound AD, except that Compound J (600 mg) was used instead of Compound AC. The structure of Compound AH was confirmed by the following NMR data.

[0230]

[0231] (NMR spectrum of compound AH) 1 H-NMR (400MHz, CDCl3) δ 4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.1 Hz, 1H), 3.57 (t, J = 6.7 Hz, 2H), 3.41 (t, J = 6.9 Hz, 2H), 1.89 - 1.82 (m, 2H), 1.61 - 1.54 (m, 2H), 1.45 - 1.24 (m, 28H). 19 F-NMR (376MHz, CDCl3) δ-61.2.

[0232] Synthesis of Compound AI: 520 mg of Compound AI was obtained in the same manner as in the synthesis of Compound AE, except that Compound AH (620 mg) was used instead of Compound AE. The structure of Compound AI was confirmed by the following NMR data.

[0233]

[0234] (NMR spectrum of compound AI) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.0 Hz, 1H), 3.57 (t, J = 6.7 Hz, 2H), 2.07 - 2.01 (m, 2H), 1.61 - 1.55 (m, 2H), 1.39 - 1.21 (m, 62H). 19 F-NMR (376MHz, CDCl3) δ-61.2.

[0235] <Synthesis of Compound 1-1J> 600 mg of compound 1-1J was obtained in the same manner as in the synthesis procedure of compound 1-1A, except that compound AI (520 mg) was used instead of compound C. The structure of compound 1-1J was confirmed by the following NMR data.

[0236]

[0237] (NMR spectrum of compound 1-1J) 1 H-NMR (400MHz, CDCl3) δ4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.0 Hz, 1H), 3.59 - 3.56 (m, 11H), 1.61 - 1.55 (m, 2H), 1.42 - 1.21 (m, 66H), 0.67 - 0.63 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.2.

[0238] [Example 12] <Synthesis of Compound AN> 1.4 g of Compound AN was obtained in the same manner as in the synthesis of Compound AD, except that Compound N (1.5 g) was used instead of Compound AC. The structure of Compound AN was confirmed by the following NMR data.

[0239]

[0240] (NMR spectrum of compound AN) 1H-NMR (400MHz, CDCl3) δ3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.41 (t, J = 6.9 Hz, 2H), 2.09 - 2.00 (m, 1H), 1.89 - 1.81 (m, 2H), 1.43 - 1.25 (m, 32H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0241] <Synthesis of Compound AO> 770 mg of Compound AO was obtained in the same manner as in the synthesis procedure for Compound AE, except that Compound AN (1.4 g) was used instead of Compound AD and 11-bromo-1-undecene (1.3 g) was used instead of 18-bromo-1-octadecene. The structure of Compound AO was confirmed by the following NMR data.

[0242]

[0243] (NMR spectrum of compound AO) 1 H-NMR (400MHz, CDCl3) δ 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 2.06 - 2.01 (m, 3H), 1.43 - 1.25 (m, 52H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0244] <Synthesis of Compound 1-1K> 920 mg of compound 1-1K was obtained in the same synthetic procedure as compound 1-1A, except that compound AO (770 mg) was used instead of compound C. The structure of compound 1-1K was confirmed by the following NMR data.

[0245]

[0246] (NMR spectrum of compound 1-1K) 1H-NMR (400MHz, CDCl3) δ 3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.57 (s, 9H), 2.07 - 2.00 (m, 1H), 1.41 - 1.25 (m, 56H), 0.67 - 0.62 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0247] Example 13 Synthesis of Compound 1-1L 380 mg of Compound 1-1L was obtained in the same manner as in the synthesis of Compound 1-1A, except that Compound AO (300 mg) was used instead of Compound C and triethoxysilane (120 mg) was used instead of trimethoxysilane. The structure of Compound 1-1L was confirmed by the following NMR data.

[0248]

[0249] (NMR spectrum of compound 1-1L) 1 H-NMR (400MHz, CDCl3) δ 3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.82 (q, J = 6.9 Hz, 6H), 2.07 - 2.00 (m, 1H), 1.41 - 1.18 (m, 65H), 0.65 - 0.61 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0250] Example 14 Synthesis of Compound AP Under a nitrogen atmosphere, dry dimethylformamide (100 mL) and 60% sodium hydride (1.5 g, dispersed in liquid paraffin) were added to O,O'-benzylidenepentaerythritol (11 g) and stirred at room temperature for 30 minutes. 18-Bromo-1-octadecene (8.0 g) was then added and stirred at room temperature for 15 hours. Water was then added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 5.1 g of Compound AP.

[0251]

[0252] <Synthesis of Compound AQ> Under a nitrogen atmosphere, dry tetrahydrofuran (20 mL), carbon tetrabromide (3.9 g), and triphenylphosphine (3.1 g) were added to Compound AP (5.1 g) at 0°C, and the mixture was heated to room temperature and stirred for 1 hour. Hexane was added to the crude liquid, and the precipitate was filtered using Celite. The solvent and low-boiling components were distilled off under reduced pressure from the obtained filtrate. The obtained crude liquid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 3.8 g of Compound AQ.

[0253]

[0254] <Synthesis of Compound AR> Under a nitrogen atmosphere, dry dimethylformamide (20 mL) and 60% sodium hydride (dispersed in liquid paraffin, 350 mg) were added to 2-phenyl-1,3-dioxan-5-ol (600 mg) and stirred at room temperature for 30 minutes. Thereafter, Compound AQ (3.7 g) was added, and the mixture was stirred at 80°C for 15 hours. Next, water was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 1.8 g of Compound AR.

[0255]

[0256] <Synthesis of Compound AS> Methanol (50 mL) and p-toluenesulfonic acid monohydrate (500 mg) were added to Compound AR (1.8 g) and the mixture was stirred at room temperature for 15 hours. Thereafter, the reaction was terminated using an aqueous sodium bicarbonate solution. The solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: methylene chloride / methanol) to obtain 1.1 g of Compound AS. The structure of Compound AS was confirmed by the following NMR data.

[0257]

[0258] (NMR spectrum of compound AS) 1 H-NMR (400MHz, CDCl3) δ 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.80 - 3.38 (m, 15H), 2.98 (t, J = 6.0 Hz, 2H), 2.80 (t, J = 6.0 Hz, 2H), 2.07 - 2.01 (m, 2H), 1.57 - 1.52 (m, 2H), 1.39 - 1.24 (m, 26H).

[0259] <Synthesis of Compound AT> Compound AT (440 mg) was obtained in the same manner as in the synthesis of Compound A, except that Compound AS (1.0 g) was used instead of pentaerythritol monobenzyl ether. The structure of Compound AT was confirmed by the following NMR data.

[0260]

[0261] (NMR spectrum of compound AT) 1H-NMR (400MHz, CDCl3) δ 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 4.07 - 3.99 (m, 8H), 3.75 (quint, J = 5.3 Hz, 1H), 3.62 (s, 2H), 3.40 - 3.37 (m, 4H), 2.07 - 2.01 (m, 2H), 1.57 - 1.51 (m, 2H), 1.42 - 1.25 (m, 26H). 19 F-NMR (376MHz, CDCl3) δ -61.4.

[0262] <Synthesis of Compound 1-1M> 510 mg of compound 1-1M was obtained in the same manner as in the synthesis procedure for compound 1-1A, except that compound AT (440 mg) was used instead of compound C. The structure of compound 1-1M was confirmed by the following NMR data.

[0263]

[0264] (NMR spectrum of compound 1-1M) 1 H-NMR (400MHz, CDCl3) δ4.07 - 3.99 (m, 8H), 3.75 (quint, J = 5.3 Hz, 1H), 3.62 (s, 2H), 3.57 (s, 9H), 3.40 - 3.37 (m, 4H), 1.57 - 1.51 (m, 2H), 1.42 - 1.25 (m, 26H), 0.67 - 0.62 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ -61.4.

[0265] [Example 15] <Synthesis of Compound AU> 4.2 g of Compound AU was obtained in the same manner as in the synthesis of Compound AP, except that pentaerythritol (6.7 g) was used instead of O,O'-benzylidenepentaerythritol. The structure of Compound AU was confirmed by the following NMR data.

[0266]

[0267] (NMR spectrum of compound AU)1 H-NMR (400MHz, CDCl3) δ 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.55 (s, 2H), 3.47 - 3.37 (m, 8H), 2.86 (t, J = 6.0 Hz, 3H), 2.07 - 2.01 (m, 2H), 1.58 - 1.52 (m, 2H), 1.39 - 1.27 (m, 26H).

[0268] <Synthesis of Compound AV> Under a nitrogen atmosphere, dried dimethylformamide (50 mL) and 60% sodium hydride (1.9 g, dispersed in liquid paraffin) were added to Compound AU (4.0 g) and stirred at room temperature for 30 minutes. Subsequently, 1-bromo-2-(trifluoromethoxy)ethane (8.9 g) was added at 0°C, followed by stirring at room temperature for 15 hours. Next, water was added to the mixture to terminate the reaction, and hexane was added to separate the organic phase. The organic phase was washed with water and saturated brine and dried over magnesium sulfate, after which the solvent and low-boiling components were distilled off under reduced pressure. The resulting crude liquid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 6.2 g of Compound AV. The structure of Compound AV was confirmed by the following NMR data.

[0269]

[0270] (NMR spectrum of compound AV) 1 H-NMR (400MHz, CDCl3) δ 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.78 - 3.72 (m, 12H), 3.55 (s, 2H), 3.48 (s, 6H), 3.42 - 3.37 (m, 2H), 2.07 - 2.01 (m, 2H), 1.58 - 1.52 (m, 2H), 1.39 - 1.25 (m, 26H). 19 F-NMR (376MHz, CDCl3) δ-62.2.

[0271] <Synthesis of Compound 1-1N> 1.1 g of Compound 1-1N was obtained in the same manner as in the synthesis procedure for Compound 1-1A, except that Compound AV (1.0 g) was used instead of Compound C. The structure of Compound 1-1N was confirmed by the following NMR data.

[0272]

[0273] (NMR spectrum of compound 1-1N) 1 H-NMR (400MHz, CDCl3) δ 3.78 - 3.72 (m, 12H), 3.57 (s, 9H), 3.55 (s, 2H), 3.48 (s, 6H), 3.42 - 3.37 (m, 2H), 1.58 - 1.52 (m, 2H), 1.39 - 1.24 (m, 30H), 0.67 - 0.62 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-62.2.

[0274] [Production of Article] 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 chamber was evacuated to a pressure of 100 Pa or less. The hearth was heated to approximately 2,000°C, and silicon oxide was vacuum-deposited onto the surface of the substrate, preparing a silicon oxide layer-coated substrate having a silicon oxide layer approximately 20 nm thick. The silicon oxide layer-coated substrate was placed on the sample stage of a spray coater (API-90RS, manufactured by Apiros Co., Ltd.) with the silicon oxide layer facing up. Next, 13 g of a heptane solution containing 0.2 mass% of the compound obtained in each example was placed into a syringe in the spray coater and spray-coated at an atomization pressure of 130 kPa, a nozzle-to-sample surface distance of 50 mm, and a scanning speed of 300 mm / sec (wet coating method). The silicon oxide layer-coated substrate with the compound coated on its surface was then heat-treated at 140°C for 30 minutes, yielding an evaluation sample (article) in which the substrate, silicon oxide layer, and surface layer were laminated in this order.

[0275] [Evaluation] The following evaluations were carried out using the obtained articles. The results of the evaluation tests are shown in Table 1.

[0276] <Oil repellency> Approximately 2 μL of oleic acid was dropped onto the surface layer of the article, and the initial oil contact angle (oleic acid contact angle) was measured using a contact angle measuring device (product name "DM-500", manufactured by Kyowa Interface Science Co., Ltd.). Measurements were taken at five points on the surface layer, and the average value was calculated to evaluate the oil repellency of the surface layer. The 2θ method was used to calculate the oil contact angle. The evaluation criteria are as follows: S: Average oil contact angle is 62 degrees or more A: Average oil contact angle is 55 degrees or more and less than 62 degrees B: Average oil contact angle is 50 degrees or more and less than 55 degrees C: Average oil contact angle is less than 50 degrees

[0277] <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. Subsequently, an article with a surface treatment layer formed thereon was placed on a hot plate adjusted to 23°C, and the fingerprint stamp was stamped onto 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 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 are as follows: A: Haze value less than 0.1%. B: Haze value 0.1% or more but less than 0.5%. C: Haze value 0.5% or more.

[0278]

[0279] As shown in Table 1, it was confirmed that the compounds obtained in Examples 1 to 5 and Examples 7 to 15 were capable of forming a surface layer having excellent oil repellency.

[0280] Examples of the article having a surface layer containing Compound 1 include optical articles, touch panels, anti-reflection films, anti-reflection glass, and SiO ２ Useful as treated glass, tempered glass, sapphire glass, quartz substrates, mold metal, etc. Products: car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio, game devices, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (gastroscopes, etc.), copiers, personal computers (PCs), liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc.

[0281] This application claims priority based on Japanese Patent Application No. 2024-147839, filed August 29, 2024, the disclosure of which is incorporated herein in its entirety by reference.

[0282] 10 Substrate with underlayer 12 Substrate 14 Underlayer 20 Article 22 Surface layer

Claims

1. A compound represented by the following formula (1): (R ｆ ) ｎ -L ３ -L ４ -L １ - (T １ ) ｘ１ (1) However, R ｆ is -OCF ３ , -SCF ３ , -SF ４ X １１ , -N(CF ３ ) X １２ , -CHF ２ , -CH ２ F, -C ６ F ５ , or -C ８ F ７ and X １１ is an alkyl group or a halogen atom, and X １２ is an alkyl group or —CF ３ n is an integer of 2 or more; L ３ is an (n+1)-valent group that is free of fluorine atoms and organosiloxane residues, or an (n+1)-valent group that contains a cyclic hydrocarbon group in which at least one hydrogen atom is substituted with a fluorine atom and that is free of organosiloxane residues, and which may contain an oxygen atom or a nitrogen atom as a ring member atom; L ４ is -O-, -C(=O)-, -C(=O)NX １３ -, -C(=O)O-, -NX １３ C(=O)NX １４ -, -NX １３ C(=S)NX １４ -, -NX １３ C(=O)O-, -Si(X １３ ) ２ -, and a divalent aromatic heterocycle, and when the divalent hydrocarbon group contains a cyclic hydrocarbon group, the cyclic hydrocarbon group may have a substituent; X １３ and X １４ are each independently a hydrogen atom or an alkyl group, and L １ represents a single bond or a trivalent or higher (1+x1)-valent group, １ is a reactive group (excluding vinyl, 1-methylvinyl, (meth)acryloyl, and (meth)acryloyloxy groups), x1 is an integer of 1 to 10, and when x1 is 1, L １ is a single bond, and there are multiple R ｆ may be the same or different, T １ In the case where there are multiple T １ may be the same or different from each other.

2. The compound according to claim 1, wherein the compound represented by formula (1) is a compound represented by the following formula (1-1): However, in formula (1-1), L ３１ represents a single bond or an (n1+1)-valent hydrocarbon group which may have —O—; L ３２ represents N, C, Si, or a cyclic hydrocarbon group which may contain an oxygen atom or a nitrogen atom as a ring member atom and which may be substituted with a fluorine atom; R １１ represents a hydrogen atom or an alkyl group which may have —O—; １１ represents a single bond or a trivalent or higher (1+x1)-valent group, １２ represents a single bond or a hydrocarbon group which may have —O—, n1 represents an integer of 1 or more, n2 represents an integer of 2 or more, n3 represents an integer of 0 or more, and L ３２ is N, n2 is 2, n3 is 0, and L ３２ is C or Si, n2+n3 is 3, and R ｆ , L ４ , T １ , and x1 are R in formula (1), respectively. ｆ , L ４ , T １ , and x1, and there are multiple (R ｆ ) ｎ１ -L ３１ - may be the same or different.

3. A surface treatment agent comprising the compound according to claim 1 or 2.

4. The surface treatment agent according to claim 3, further comprising a liquid medium.

5. The surface treatment agent according to claim 3, which is an antifouling coating agent or a waterproof coating agent.

6. The surface treatment agent according to claim 4, which is an antifouling coating agent or a waterproof coating agent.

7. An article having a surface layer formed on the surface of a substrate using the compound according to claim 1 or 2.

8. The article according to claim 7, which is an optical element.

9. The article according to claim 7, which has the surface layer on the surface of a member that constitutes the surface of a touch panel that is touched by a finger.

10. A method for manufacturing an article, which comprises forming a surface layer by a dry coating method using the surface treatment agent according to claim 3.

11. A method for manufacturing an article, which comprises forming a surface layer by a dry coating method using the surface treatment agent according to claim 4.

12. A method for manufacturing an article, which comprises forming a surface layer by a wet coating method using the surface treatment agent according to claim 4.

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