Compound, composition, surface treatment agent, coating liquid, article, and method for producing article

Abstract

The present invention provides a fluorine-containing ether compound which is represented by formula (1) or formula (2).　Formula (1): A1-(ORf1)y1-R1-Q1-R2-L1-(R3-T1)x1 Formula (2): (T3-R9)x3-L3-R8-Q3-R7-Rf-(ORf2)y2-R4-Q2-R5-L2-(R6-T2)x2 In the formulae, the symbols are as defined in the description.

Description

Compound, composition, surface treatment agent, coating liquid, article, and method for manufacturing article

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

[0002] Fluorine-containing ether compounds have excellent properties such as low refractive index, low dielectric constant, water and oil repellency, heat resistance, chemical resistance, chemical stability, and transparency, and are used in a wide variety of fields, including electrical and electronic materials, semiconductor materials, optical materials, and surface treatment agents.

[0003] For example, a fluorine-containing ether compound having a perfluoropolyether chain and a hydrolyzable silyl group is suitable for use as a surface treatment agent because it can form a surface layer on the surface of a substrate that exhibits high lubricity, water and oil repellency, etc. Surface treatment agents containing fluorine-containing ether compounds are used in applications where it is required that the performance of the surface layer not easily reduced in water and oil repellency even when rubbed repeatedly with fingers (abrasion resistance) and the performance of easily removing fingerprints attached to the surface layer by wiping (fingerprint stain removability) be maintained for a long period of time, such as surface treatment agents for components constituting the surfaces of touch panels that are touched by fingers, eyeglass lenses, and displays of wearable devices.

[0004] As a fluorine-containing ether compound capable of forming a surface layer having excellent abrasion resistance on the surface of a substrate, a fluorine-containing ether compound having a perfluoropolyether chain and a hydrolyzable silyl group has been proposed (Patent Document 1).

[0005] JP 2016-037541 A

[0006] As described above, fluorine-containing ether compounds are useful as surface treatment agents for imparting the above-mentioned various physical properties, and there is an increasing demand for fluorine-containing ether compounds that can be used in a variety of environments. The present inventors have conducted studies with the aim of further improving the abrasion resistance and light fastness.

[0007] An object of the present invention is to provide a compound, composition, surface treatment agent, coating liquid, article, and method for producing an article, which are excellent in abrasion resistance and light resistance.

[0008] The present invention provides a fluorine-containing ether compound, a composition, a surface treatment agent, a coating liquid, an article, and a method for producing an article, each having the following structures [1] to

[11] . [1] A compound represented by the following formula (1) or (2): １ - (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２ -L １ - (R ３ -T １ ) ｘ１ ...Formula (1) (T ３ -R ９ ) ｘ３ -L ３ -R ８ -Q ３ -R ７ -R ｆ - (OR ｆ２ ) ｙ２ -R ４ -Q ２ -R ５ -L ２ - (R ６ -T ２ ) ｘ２ ...Equation (2) where A １ is a fluoroalkyl group having 1 to 20 carbon atoms, and R ｆ１ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ１ If there are multiple R ｆ１ may be the same or different, R １ is a single bond or a divalent group, and Q １ contains one or more ring structures, and the atoms constituting the ring structures are R １ and R ２ is a divalent group bonded to R ２ is a single bond or a divalent group, L １ is a single bond or a 1+x1-valent group which may have N, O, S, or Si and may have a branch point, and R ２ and R ３ Atoms bonded to R are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (=O), ３is an alkylene group, or L １ an alkylene group having an ether oxygen atom at the terminal or between carbon atoms of the R ３ If there are multiple R ３ may be the same or different, T １ is -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ and R ａ１ is a hydroxyl group or a hydrolyzable group, and R ａ１ If there are multiple R ａ１ may be the same or different, R ａ１１ is a non-hydrolyzable group, and R ａ１１ If there are multiple R ａ１１ may be the same or different, z1 is an integer of 0 to 3, and when there are a plurality of z1, the plurality of z1 may be the same or different, provided that at least one of z1 is an integer of 1 to 3, x1 is an integer of 1 or more, y1 is an integer of 1 or more, R ｆ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ２ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ２ If there are multiple R ｆ２ may be the same or different, R ４ is a single bond or a divalent group, and Q ２ contains one or more ring structures, and the atoms constituting the ring structures are R ４ and R ５ is a divalent group bonded to R ５ is a single bond or a divalent group, L ２ is a single bond or a 1+x divalent group which may have N, O, S, or Si and may have a branch point, and R ５ and R ６ Atoms bonded to R are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (=O), ６ is an alkylene group, or L ２an alkylene group having an ether oxygen atom at the terminal or between carbon atoms of the R ６ If there are multiple R ６ may be the same or different, T ２ is -SiR ａ２ ｚ２ R ａ１２ ３－ｚ２ and R ａ２ is a hydroxyl group or a hydrolyzable group, and R ａ２ If there are multiple R ａ２ may be the same or different, R ａ１２ is a non-hydrolyzable group, and R ａ１２ If there are multiple R ａ１２ may be the same or different from each other, z2 is an integer of 0 to 3, and when there are a plurality of z2, the plurality of z2 may be the same or different from each other, provided that at least one of z2 is an integer of 1 to 3, R ７ is a single bond or a divalent group, and Q ３ contains one or more ring structures, and the atoms constituting the ring structures are R ７ and R ８ is a divalent group bonded to R ８ is a single bond or a divalent group, L ３ is a single bond or a 1+x trivalent group which may have N, O, S, or Si and may have a branch point, and R ８ and R ９ Atoms bonded to R are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (=O), ９ is an alkylene group, or L ３ an alkylene group having an ether oxygen atom at the terminal or between carbon atoms of the R ９ If there are multiple R ９ may be the same or different, T ３ is -SiR ａ３ ｚ３ R ａ１３ ３－ｚ３ and R ａ３is a hydroxyl group or a hydrolyzable group, and R ａ３ If there are multiple R ａ３ may be the same or different, R ａ１３ is a non-hydrolyzable group, and R ａ１３ If there are multiple R ａ１３ may be the same or different, z3 is an integer of 0 to 3, and when there are multiple z3s, the multiple z3s may be the same or different, provided that at least one of the z3s is an integer of 1 to 3, x2 and x3 are each independently an integer of 1 or more, and y2 is an integer of 1 or more. [2] Q １ , Q ２ and Q ３ The compound of claim [1], wherein at least one of Q is a divalent group containing one monocyclic or condensed ring. １ , Q ２ and Q ３ [4] The compound of [1] or [2], wherein at least one of R is a divalent group that forms a ring and has bonds on adjacent carbon atoms. １ , R ４ and R ７ [5] The compound according to any one of [1] to [3], wherein at least one of R is an alkylene group. ２ , R ５ and R ８ wherein at least one of the groups is a single bond or an alkylene group. [6] A composition containing any of the compounds [1] to [5] and another fluorine-containing ether compound. [7] A surface treatment agent containing any of the compounds [1] to [5] or the composition [6]. [8] A coating liquid containing any of the compounds [1] to [5] or the composition [6] and a liquid medium. [9] An article having a surface layer formed on the surface of a substrate from any of the compounds [1] to [5], the composition [6], or the surface treatment agent [7].

[10] A method for producing an article, comprising forming a surface layer by a dry coating method or a wet coating method using any of the compounds [1] to [5], the composition [6], the surface treatment agent [7], or the coating liquid [9].

[11] A compound represented by the following formula (3) or (4): A１ - (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２１ -D １ ...Formula (3) D ３ -R ８１ -Q ３ -R ７ -R ｆ - (OR ｆ２ ) ｙ２ -R ４ -Q ２ -R ５１ -D ２ ...Equation (4) where A １ is a fluoroalkyl group having 1 to 20 carbon atoms, and R ｆ１ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ１ If there are multiple R ｆ１ may be the same or different, R １ is a single bond or a divalent group, and Q １ contains one or more ring structures, and the atoms constituting the ring structures are R １ and R ２ is a divalent group bonded to R ２１ is a single bond or a divalent group, １ is a halogen atom, y1 is an integer of 1 or more, R ｆ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ２ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ２ If there are multiple R ｆ２ may be the same or different, R ４ is a single bond or a divalent group, and Q ２ contains one or more ring structures, and the atoms constituting the ring structures are R ４ and R ５ is a divalent group bonded to R ５１ is a single bond or a divalent group, R ７ is a single bond or a divalent group, and Q ３ contains one or more ring structures, and the atoms constituting the ring structures are R ７ and R８ is a divalent group bonded to R ８１ is a single bond or a divalent group, ２ and D ３ are each independently a halogen atom, and y2 is an integer of 1 or more.

[0009] The present invention provides a compound, composition, surface treatment agent, coating liquid, article, and method for producing an article, all of which have excellent abrasion resistance and light resistance.

[0010] 1 is a schematic cross-sectional view showing an example of an article of the present invention.

[0011] 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 in this manner. "(Poly)oxyfluoroalkylene" is a general term for oxyfluoroalkylene and polyoxyfluoroalkylene. "Fluoroalkyl group" is a general term that includes perfluoroalkyl and partial fluoroalkyl groups. "Perfluoroalkyl group" refers to a group in which all hydrogen atoms of an alkyl group are substituted with fluorine atoms. "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. "Reactive silyl group" is a general term for hydrolyzable silyl groups and silanol groups (Si—OH), and "hydrolyzable silyl group" refers to a group that can form a silanol group by hydrolysis. "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 "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 "surface layer" refers to a layer formed on the surface of the substrate. The "molecular weight" of the fluoropolyether chain is １ H-NMR and １９The number average molecular weight is calculated by F-NMR to determine the number (average value) of oxyfluoroalkylene units based on the terminal groups. The range of values ​​indicated by "to" means that the values ​​before and after it are included as the lower and upper limits.

[0012] [Compound] The compound of the present invention is characterized by being represented by the following formula (1) or (2): １ - (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２ -L １ - (R ３ -T １ ) ｘ１ ...Formula (1) (T ３ -R ９ ) ｘ３ -L ３ -R ８ -Q ３ -R ７ -R ｆ - (OR ｆ２ ) ｙ２ -R ４ -Q ２ -R ５ -L ２ - (R ６ -T ２ ) ｘ２ ...Equation (2) where A １ is a fluoroalkyl group having 1 to 20 carbon atoms, and R ｆ１ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ１ If there are multiple R ｆ１ may be the same or different, R １ is a single bond or a divalent group, and Q １ contains one or more ring structures, and the atoms constituting the ring structures are R １ and R ２ is a divalent group bonded to R ２ is a single bond or a divalent group, L １ is a single bond or a 1+x1-valent group which may have N, O, S, or Si and may have a branch point, and R ２ and R ３Atoms bonded to R are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (=O), ３ is an alkylene group, or L １ an alkylene group having an ether oxygen atom at the terminal or between carbon atoms of the R ３ If there are multiple R ３ may be the same or different, T １ is -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ and R ａ１ is a hydroxyl group or a hydrolyzable group, and R ａ１ If there are multiple R ａ１ may be the same or different, R ａ１１ is a non-hydrolyzable group, and R ａ１１ If there are multiple R ａ１１ may be the same or different, z1 is an integer of 0 to 3, and when there are a plurality of z1, the plurality of z1 may be the same or different, provided that at least one of z1 is an integer of 1 to 3, x1 is an integer of 1 or more, y1 is an integer of 1 or more, R ｆ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ２ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ２ If there are multiple R ｆ２ may be the same or different, R ４ is a single bond or a divalent group, and Q ２ contains one or more ring structures, and the atoms constituting the ring structures are R ４ and R ５ is a divalent group bonded to R ５ is a single bond or a divalent group, L ２ is a single bond or a 1+x divalent group which may have N, O, S, or Si and may have a branch point, and R ５ and R ６Atoms bonded to R are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (=O), ６ is an alkylene group, or L ２ an alkylene group having an ether oxygen atom at the terminal or between carbon atoms of the R ６ If there are multiple R ６ may be the same or different, T ２ is -SiR ａ２ ｚ２ R ａ１２ ３－ｚ２ and R ａ２ is a hydroxyl group or a hydrolyzable group, and R ａ２ If there are multiple R ａ２ may be the same or different, R ａ１２ is a non-hydrolyzable group, and R ａ１２ If there are multiple R ａ１２ may be the same or different from each other, z2 is an integer of 0 to 3, and when there are a plurality of z2, the plurality of z2 may be the same or different from each other, provided that at least one of z2 is an integer of 1 to 3, R ７ is a single bond or a divalent group, and Q ３ contains one or more ring structures, and the atoms constituting the ring structures are R ７ and R ８ is a divalent group bonded to R ８ is a single bond or a divalent group, L ３ is a single bond or a 1+x trivalent group which may have N, O, S, or Si and may have a branch point, and R ８ and R ９ Atoms bonded to R are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having a hydroxyl group or an oxo group (=O), ９ is an alkylene group, or L ３ an alkylene group having an ether oxygen atom at the terminal or between carbon atoms of the R ９ If there are multiple R ９may be the same or different, T ３ is -SiR ａ３ ｚ３ R ａ１３ ３－ｚ３ and R ａ３ is a hydroxyl group or a hydrolyzable group, and R ａ３ If there are multiple R ａ３ may be the same or different, R ａ１３ is a non-hydrolyzable group, and R ａ１３ If there are multiple R ａ１３ may be the same or different from each other, z3 is an integer of 0 to 3, and when there are multiple z3's, the multiple z3's may be the same or different from each other, provided that at least one of the z3's is an integer of 1 to 3, x2 and x3 are each independently an integer of 1 or more, and y2 is an integer of 1 or more.

[0013] Compound 1 roughly has a structure of "fluoropolyether chain-linking group containing a ring structure-reactive silyl group." Compound 2 roughly has a structure of "reactive silyl group-linking group containing a ring structure-fluoropolyether chain-linking group containing a ring structure-reactive silyl group." Because this compound has a fluoropolyether chain, the surface layer obtained using this compound has excellent water and oil repellency and fingerprint stain removability. This compound has a reactive silyl group. The reactive silyl group firmly chemically bonds to the substrate, so the surface layer obtained has excellent durability, such as abrasion resistance. In compounds 1 and 2, the fluoroether chain and the reactive silyl group are linked by a linking group containing a ring structure. The linking group containing a ring structure can maintain the link between the polyfluoroether chain and the reactive silyl group even if some of the bonds contained in the ring structure are cleaved, for example, by friction or light irradiation. Therefore, the surface layer formed by this compound has excellent water and oil repellency and fingerprint stain removability, as well as excellent abrasion resistance and light fastness. The structure of each compound will be explained below, and symbols having similar structures will be indicated as such and can be read interchangeably for reference as appropriate.

[0014] <Compound 1> Compound 1 has a structure represented by the following formula (1): １- (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２ -L １ - (R ３ -T １ ) ｘ１ ...Equation (1) where the symbols in equation (1) are as described above.

[0015] A １ is a fluoroalkyl group having 1 to 20 carbon atoms. The fluoroalkyl group may be a linear alkyl group or an alkyl group having a branched and / or cyclic structure. From the viewpoint of abrasion resistance, a linear fluoroalkyl group is preferred. Furthermore, from the viewpoint of ease of synthesis, the fluoroalkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.

[0016] R ｆ１ is a fluoroalkylene group having 1 to 6 carbon atoms, and R ｆ１ If there are multiple R ｆ１ may be the same or different. (OR ｆ１ ) ｙ１ is a fluoropolyether chain, and y1 is an integer of 1 or more.

[0017] (OR ｆ１ ) ｙ１ The fluoropolyether chain in the formula (G1) preferably has a structure represented by the following formula (G1): ｆ１ ) ｍ１ (OG ｆ２ ) ｍ２ (OG ｆ３ ) ｍ３ (OG ｆ４ ) ｍ４ (OG ｆ５ ) ｍ５ (OG ｆ６ ) ｍ６ ]- Formula (G1) where G ｆ１ is a fluoroalkylene group having 1 carbon atom, ｆ２ is a fluoroalkylene group having 2 carbon atoms, ｆ３ is a fluoroalkylene group having 3 carbon atoms, ｆ４is a fluoroalkylene group having 4 carbon atoms, ｆ５ is a fluoroalkylene group having 5 carbon atoms, ｆ６ is a fluoroalkylene group having 6 carbon atoms, m1, m2, m3, m4, m5, and m6 each independently represent an integer of 0 or 1 or more, and m1+m2+m3+m4+m5+m6 is an integer of 1 to 200. ｆ１ ) ~ (OG ｆ６ The bonding order of m1 to m6 in formula (G1) is arbitrary. ｆ１ ) ~ (OG ｆ６ ) and does not represent the arrangement. For example, (OG ｆ５ ) ｍ５ (OG ｆ５ ) is m5, and (OG ｆ５ ) ｍ５ Similarly, it does not represent the block arrangement structure of (OG ｆ１ ) ~ (OG ｆ６ The order of the units does not represent the bonding order of the units. The fluoroalkylene group having 3 to 6 carbon atoms may be a linear fluoroalkylene group or a fluoroalkylene group having a branched or cyclic structure.

[0018] G ｆ１ Specific examples of the group include -CF ２ -, -CHF-. ｆ２ Specific examples of the group include -CF ２ CF ２ -, -CHFCF ２ -, -CHFCHF-, -CH ２ CF ２ -, -CH ２ CHF-, etc. ｆ３ Specific examples of the group include -CF ２ CF ２ CF ２ -, -CF ２ CHFCF ２ -, -CF ２ CH ２ CF ２ -, -CHFCF ２ CF ２ -, -CHFCHFCF２ -、-CHFCHFCHF-、-CHFCH ２ CF ２ -、-CH ２ CF ２ CF ２ -、-CH ２ CHFCF ２ -、-CH ２ CH ２ CF ２ -、-CH ２ CF ２ CHF-、-CH ２ CHFCHF-、-CH ２ CH ２ CHF-、-CF(CF ３ )-CF ２ -、-CF(CHF ２ )-CF ２ -、-CF(CH ２ F)-CF ２ -、-CF(CH ３ )-CF ２ -、-CF(CF ３ )-CHF-、-CF(CHF ２ )-CHF-、-CF(CH ２ F)-CHF-、-CF(CH ３ )-CHF-、-CF(CF ３ )-CH ２ -、-CF(CHF ２ )-CH ２ -、-CF(CH ２ F)-CH ２ -、-CF(CH ３ )-CH ２ -、-CH(CF ３ )-CF ２ -、-CH(CHF ２ )-CF ２ -、-CH(CH ２ F)-CF ２ -、-CH(CH ３ )-CF ２ -、-CH(CF ３ )-CHF-、-CH(CHF ２ )-CHF-、-CH(CH ２ F)-CHF-、-CH(CH ３ )-CHF-、-CH(CF ３ )-CH ２-, -CH(CHF ２ ) - CH ２ -, -CH(CH ２ F) - CH ２ - etc. are cited. G ｆ４ As a specific example of, -CF ２ CF ２ CF ２ CF ２ -, -CHFCF ２ CF ２ CF ２ -, -CH ２ CF ２ CF ２ CF ２ -, -CF[[ID=3\3]] ２ CHFCF ２ CF ２ -, -CHFCHFCF ２ CF ２ -, -CH ２ CHFCF ２ CF ２ -, -CF ２ CH ２ CF ２ CF ２ -, -CHFCH ２ CF ２ CF ２ -, -CH<{ ２ CH ２ CF<000\0417>CF ２ -, -CHFCF ２ CHFCF ２ -, -CH ２ CF<000042\2>CHFCF ２ -, -CF ２ CHFCHFCF ２ -, -CHFCHFCHFCF ２ -, -CH ２ CHFCHFCF ２ -, -CF ２ CH[[ID=9\3]] ２ CHFCF ２ -, -CHFCH ２ CHFCF ２ -, -CH ２ CH ２ CHFCF ２ -, -CF ２ CH ２ CH ２ CF２ -, -CHFCH ２ CH ２ CF ２ -, -CH ２ CH ２ CH ２ CF ２ -, -CHFCH ２ CH ２ CHF-, -CH ２ CH ２ CH ２ CHF-, -cycloC ４ F ６ - etc. are listed. G ｆ５ As a specific example of G, -CF ２ CF ２ CF ２ CF ２ CF ２ -, -CHFCF ２ CF ２ CF ２ CF ２ -, -CH ２ CHFCF ２ CF ２ CF ２ -, -CF ２ CHFCF ２ CF ２ CF ２ -, -CHFCHFCF ２ CF<工业产权局: ２ CF ２ -, -CF ２ CH ２ CF ２ CF ２ CF ２ -, -CHFCH ２ CF ２ CF ２ CF ２ -, -CH ２ CH ２ CF ２ CF ２ CF ２ -, -CF ２ CF ２ CHFCF ２ CF ２ -, -CHFCF ２ CHFCHF ２ CF ２ -, -CH ２ CF ２ CHFCF２ CF ２ -, -CH ２ CF ２ CF ２ CF ２ CH ２ -, -cycloC ５ F ８ - and others. ｆ６ Specific examples of the group include -CF ２ CF ２ CF ２ CF ２ CF ２ CF ２ -, -CF ２ CF ２ CHFCHFCF ２ CF ２ -, -CHFCF ２ CF ２ CF ２ CF ２ CF ２ -, -CHFCHFCHFCHFCHFCHF-, -CHFCF ２ CF ２ CF ２ CF ２ CH ２ -, -CH ２ CF ２ CF ２ CF ２ CF ２ CH ２ -, -cycloC ６ F １０ -, etc. Here, -cycloC ４ F ６ - means a perfluorocyclobutanediyl group, and a specific example thereof is a perfluorocyclobutane-1,2-diyl group. ５ F ８ - means a perfluorocyclopentanediyl group, and a specific example thereof is a perfluorocyclopentane-1,3-diyl group. ６ F １０ "-" means a perfluorocyclohexanediyl group, and a specific example thereof is a perfluorocyclohexane-1,4-diyl group.

[0019] (OR ｆ１ )ｙ１ In particular, it is preferable that the compound has a structure represented by the following formula (G2) to formula (G4) because it has excellent water and oil repellency, abrasion resistance, and fingerprint stain removal properties. ｆ１ ) ｍ１ - (OG ｆ２ ) ｍ２ ...Formula (G2) (OG ｆ２ ) ｍ２ - (OG ｆ４ ) ｍ４ ...Formula (G3) (OG ｆ３ ) ｍ３ Formula (G4) Here, the symbols in formulas (G2) to (G4) are the same as those in formula (G1).

[0020] In formula (G2) and formula (G3), (OG ｆ１ ) and (OG ｆ２ ), (OG ｆ２ ) and (OG ｆ４ ) can be bonded in any order. For example, (OG ｆ１ ) and (OG ｆ２ ) may be alternately arranged, and (OG ｆ１ ) and (OG ｆ２ ) may be arranged in blocks or randomly. The same applies to formula (G3). In formula (G2), m1 is preferably 1 to 50, more preferably 1 to 30. Furthermore, m2 is preferably 1 to 50, more preferably 1 to 30. In formula (G3), m2 is preferably 1 to 50, more preferably 1 to 30. Furthermore, m4 is preferably 1 to 50, more preferably 1 to 30. In formula (G4), m3 is preferably 1 to 50, more preferably 1 to 30.

[0021] The fluoropolyether chain (OR ｆ１ ) ｙ１ The proportion of fluorine atoms in the fluoropolyether chain (OR) [{number of fluorine atoms / (number of fluorine atoms+number of hydrogen atoms)}×100(%)] is preferably 60% or more, more preferably 70% or more, and even more preferably 80% or more, from the viewpoint of excellent water and oil repellency and fingerprint removability. ｆ１ ) ｙ１From the viewpoint of abrasion resistance, the molecular weight of the R moiety is preferably 200 to 30,000, more preferably 600 to 25,000, and even more preferably 1,000 to 20,000. ｆ１ R in １ or Q １ The carbon atom bonded to is bonded to at least one fluorine atom.

[0022] R １ is a single bond or a divalent group. １ is a single bond, the compound has R ｆ１ But, Q １ It has a structure directly bonded to R １ is a divalent group, R １ is, for example, —O—, —S—, —C(═O)NR Ｎ -, -NR Ｎ A bond B selected from C(=O)-, -C(=O)O-, -OC(=O)-, and -C(=O)- １ , or R ｆ１ Side end, Q １ The bond B １ and alkylene groups which may have R Ｎ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. The alkylene group may be linear or branched. From the viewpoint of abrasion resistance, a linear alkylene group is preferred. From the viewpoint of ease of synthesis, the number of carbon atoms in the alkylene group is preferably 1 to 6, and more preferably 1 to 3. Furthermore, the bond B that the alkylene group may have is １ As R, —O— is preferred. １ From the viewpoint of ease of synthesis, *-R is preferably a group represented by the following formula (g1): ３１ -(O-R ３２ ) ａ１ -** ... formula (g1) where R ３１ is a single bond or a linear alkylene group having 1 to 6 carbon atoms; R ３２ is a linear alkylene group having 1 to 6 carbon atoms, a1 is an integer of 0 to 3, * is R ｆ１ ** is a side bond of Q １It is a side bond. ３１ When is an alkylene group, R ｆ１ No, R ３１ The carbon atom bonded to is bonded to one or more fluorine atoms.

[0023] Furthermore, R １ From the viewpoint of ease of synthesis, a group represented by the following formula (g1a) is more preferred: *-(O) ａ２ -R ３３ -** ... Formula (g1a) where R ３３ is a linear alkylene group having 1 to 6 carbon atoms, a2 is an integer of 0 or 1, * is R ｆ１ ** is a side bond of Q １ When a2 is 0, R ｆ１ No, R ３３ The carbon atom bonded to is bonded to one or more fluorine atoms.

[0024] Furthermore, from the viewpoint of ease of synthesis, R １ is preferably an alkylene group, more preferably a linear alkylene group having 1 to 3 carbon atoms.

[0025] Q １ contains one or more ring structures, and the atoms constituting the ring structures are R １ and R ２ Specifically, Q is a divalent group that bonds to １ can be expressed by the following formula (Q1): １ - (R Ｊ１ -J ２ ) ｋ１ -** ... Formula (Q1) where J １ and J ２ are each independently a ring structure, ２ If there are multiple J ２ may be the same or different, R Ｊ１ is a single bond or a divalent group, and R Ｊ１ If there are multiple R Ｊ１ may be the same or different, k1 is an integer of 0 or more, * is R １ is a side bond, and ** is R ２ It is a side bond.

[0026] Q １ The ring structure J contains １ and J ２ The ring structure may be either a monocyclic structure or a fused ring structure, may have a heteroatom, or may further have a bridged structure within the ring structure. Examples of the heteroatom include O, N, S, and Si. From the viewpoint of the stability of the ring structure, each ring structure is preferably a 3- to 11-membered ring, more preferably a 4- to 8-membered ring, and even more preferably a 5- to 8-membered ring.

[0027] Examples of the monocyclic structure include structures derived from aromatic rings such as benzene, furan, thiophene, pyrrole, pyran, pyridine, pyrazole, oxazole, imidazole, and thiazole; structures derived from aliphatic rings which may have a double bond, such as cyclopropane, cyclobutane, cyclopentane, cyclopentene, cyclohexane, and cyclohexene; structures derived from cyclic ethers such as oxetane, tetrahydrofuran, and tetrahydropyran; and structures derived from cyclic amines such as pyrrolidine, pyrrolidone, and piperidine. Examples of the fused ring structure include structures derived from polycyclic aromatic rings such as naphthalene, anthracene, benzofuran, thionaphthene, carbazole, benzo-pyrone, quinoline, acridine, phthalazine, and quinoxaline; structures derived from fused aliphatic rings such as decahydronaphthalene; and fused rings of aromatic rings and aliphatic rings such as tetralin. Examples of structures having a bridged structure within a ring structure include norbornane, bicyclo[2,2,2]octane, and adamantane. Note that the above J １ and J ２ The ring structure in the above formula (I) refers to a structure in which any two hydrogen atoms of the ring are bonded together.

[0028] R Ｊ１ is a divalent group, R Ｊ１ is, for example, —O—, —S—, —C(═O)NR Ｎ１ -, -NR Ｎ１ A bond B selected from C(=O)-, -C(=O)O-, -OC(=O)-, and -C(=O)- ２ , or J １ Lateral end, J ２The bond B ２ and an alkylene group which may have a carbon-carbon double bond. Ｎ１ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0029] k1 is an integer equal to or greater than 0. When k1 is 0, Q １ is the ring structure J １ When k1 is 1 or more, Q is a group consisting of only １ is a group in which multiple ring structures are linked together. １ Specific examples of k1 include structures derived from biphenyl, terphenyl, diphenylmethane, stilbene, and diphenyl ether. In terms of ease of synthesis, abrasion resistance, and light fastness, k1 is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0030] Q １ From the viewpoints of abrasion resistance, light resistance, etc., the ring structure contained in Q is preferably a carbon ring structure having no heteroatom. １ The ring structure contained in Q is preferably a divalent group having bonds on adjacent carbon atoms that form a ring. １ The ring structure contained in is not limited to a structure in which adjacent carbon atoms constituting the ring have bonds, and may be, for example, a structure in which non-adjacent carbon atoms constituting the ring have bonds.

[0031] Q １ Specific examples of the ring structure contained in R include the following structures: Ｑ may be a protecting group for protecting an amino group contained in the ring structure, or may be a monovalent hydrocarbon group, or R １ or R ２ Each n1 is independently an integer of 1 to 3.

[0032]

[0033] R ２ is a single bond or a divalent group.２ is a single bond, the compound １ L １ It has a structure directly bonded to R ２ is a divalent group, R ２ is, for example, —O—, —S—, —C(═O)NR Ｎ２ -, -NR Ｎ２ C(=O)-, -C(=O)O-, -OC(=O)-, -C(=O)-, -NR ２ -, -SO ２ NR Ｎ２ -, -Si(R Ｎ２ ) ２ -, -OSi(R Ｎ２ ) ２ Bond B selected from ３ , or Q １ Side end, L １ The bond B ３ is an alkylene group which may have the formula: Ｎ２ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. The alkylene group may be linear or branched. From the viewpoint of abrasion resistance, a linear alkylene group is preferred. From the viewpoint of ease of synthesis, the number of carbon atoms in the alkylene group is preferably 1 to 6, and more preferably 1 to 3. Furthermore, the bond B that the alkylene group may have is １ As R, —O— is preferred. ２ From the viewpoint of ease of synthesis, *-R is preferably a group represented by the following formula (g2): ３４ -(O-R ３５ ) ａ３ -** ... formula (g2) where R ３４ is a linear alkylene group having 1 to 6 carbon atoms, and R ３５ is a linear alkylene group having 1 to 6 carbon atoms, and R ３４ If there are multiple R ３４ may be the same or different, a3 is an integer of 0 to 3, * is Q １ ** is a side bond, and L １ Furthermore, from the viewpoint of ease of synthesis, R ２is preferably an alkylene group, more preferably a linear alkylene group having 1 to 3 carbon atoms.

[0034] L １ is a single bond or a 1+x1-valent group which may have N, O, S, or Si and may have a branch point, and R ２ and R ３ The atoms bonded to are each independently an N, O, S, or Si atom, or a carbon atom constituting a hydroxyl group or a branch point.

[0035] L １ When R in formula (1) is a single bond, ２ and R ３ is directly bonded.

[0036] L １ When L is a trivalent or higher valent group, １ is at least one branch point (hereinafter referred to as "branch point P") selected from the group consisting of C, N, Si, a ring structure, and a (1+x1)-valent organopolysiloxane residue. １ ").

[0037] N is the branch point P １ If so, the branch point P １ For example, *-N(-**) ２ where * is R ２ is a bond on the side, and ** is R ３ C is the branch point P １ If so, the branch point P １ For example, *-C(-**) ３ or *-CR ２９ (-**) ２ where * is R ２ is a bond on the side, and ** is R ３ side bond, R ２９ is a monovalent group, and examples thereof include a hydrogen atom, a hydroxyl group, an alkyl group, and an alkoxy group. １ If so, the branch point P １ For example, *-Si(-**) ３ or *-SiR ２９ (-**) ２ where * is R ２ is a bond on the side, and ** is R ３side bond, R ２９ is a monovalent group, and examples thereof include a hydrogen atom, a hydroxyl group, an alkyl group, and an alkoxy group.

[0038] Branch point P １ From the viewpoints of ease of production of the present compound and of further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer, the ring structure constituting the formula (I) is preferably one selected from the group consisting of a 3- to 8-membered aliphatic ring, a 3- to 8-membered aromatic ring, a 3- to 8-membered heterocycle, and a fused ring consisting of two or more of these rings, and particularly preferably a ring structure represented by the following formula: 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).

[0039]

[0040] Branch point P １ Examples of the organopolysiloxane residue constituting the formula include the following groups: ２５ is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. ２５ The alkyl group and alkoxy group preferably have 1 to 10 carbon atoms, and more preferably 1 carbon atom.

[0041]

[0042] Divalent or higher L １ is -C(O)N(R ２６ ) -, -N(R ２６ )C(O)-, -C(O)O-, -OC(O)-, -C(O)-, -O-, -N(R ２６ )-, -S-, -OC(O)O-, -NHC(O)O-, -OC(O)NH-, -NHC(O)N(R ２６ ) -, -SO ２ N (R ２６ ) -, -N(R ２６ ) SO ２ -, -Si(R ２６ ) ２ -, -OSi(R ２６ ) ２ -, -Si(CH ３ ) ２-Ph-Si(CH ３ ) ２ - and at least one bond selected from the group consisting of a divalent organopolysiloxane residue (hereinafter referred to as "bond B ４ "). However, R ２６ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph 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 the present compound.

[0043] Examples of the divalent organopolysiloxane residue include groups of the following formula: ２７ is 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.

[0044]

[0045] Join B ４ As the group, —C(O)NR is preferred in terms of ease of production of the present compound. ２６ -, -N(R ２６ )C(O)—, —C(O)—, and —NR ２６ In view of the superior light resistance and chemical resistance of the surface layer, at least one bond selected from the group consisting of —C(O)NR ２６ -, -N(R ２６ )C(O)- or -C(O)- is more preferred.

[0046] Trivalent or higher L １ is R ２ and R ３ are each independently an N, O, S, or Si atom, a carbon atom constituting a branch point, or a carbon atom having an oxo group (=O). ２ and R ３ The atoms adjacent to each bond B ４ Or branch point P １ It is a constituent element of trivalent or higher L １ As a specific example of １ (For example, {*-P１ (-**) ｘ１}), one or more branch points P １ and one or more bonds B ４ and combinations (for example, *-B ４ -R ２８ -P １ (-**) ｘ１}, {*-B ４ -R ２８ -P １ (-R ２８ -B ４ -**) ｘ１}), etc. However, R ２８ is a single bond or a divalent organic group, and * is R ２ is a bond on the side, and ** is R ３ It is the connecting hand on the side.

[0047] Also, divalent L １ As for R ２ and R ３ are each independently an N, O, S, or Si atom or a carbon atom having an oxo group (=O). ２ and R ３ The atoms adjacent to each bond B ４ It is a constituent element of divalent or higher L １ Specific examples of B include a single bond, one or more bonds B ４ (For example, *-B ４ -**, *-B ４ -R ２８ -B ４ -**), etc. However, R ２８ is a single bond or a divalent organic group, and * is R ２ is a bond on the side, and ** is R ３ It is the connecting hand on the side.

[0048] 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 its carbon atom and its carbon atom. ４ The divalent organic group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms.

[0049] Said L １ As the group, a group represented by any one of the following formulae (E1) to (E7) is preferred in terms of ease of production of the present compound.

[0050] ... Formula (E1) -E １ -C(R Ｅ２ ) ３－ｅ３ (-E ２２ -) ｅ３ ...Formula (E2) -E ２ -N (-E ２３ -) ２ ...Formula (E3) -E ３ -Z １ (-E ２４ -) ｅ４ ... Formula (E4) -E ２ -Si(R Ｅ３ ) ３－ｅ３ (-E ２５ -) ｅ３ ...Formula (E5) -E １ -E ２６ -...Formula (E6) -E １ -CH(-E ２２ -)-Si(R Ｅ３ ) ３－ｅ５ (-E ２５ -) ｅ５ ...Formula (E7) However, in formulas (E1) to (E7), E １ , E ２ or E ３ side is R in formula (1) ２ Connect with E ２２ , E ２３ , E ２４ , E ２５ or E ２６ Side is R ３ where E １ is a single bond, -B ５ -, -B ６ -R ４０ - or -B ６ -R ４０ -B ５ - and 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-, ５ is -C(O)NR Ｅ６ -, -C(O)-, -NR Ｅ６ - or -O-, B ６ -C(O)NR Ｅ６ -, -C(O)-, or -NR Ｅ６ - and E ２ is a single bond or -B ６ -R ４０ - and E 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 —C(O)NR between carbon atoms of an alkylene group having two or more 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 If there are two or more, there are two or more Q ２２ may be the same or different, E ２３ is a single bond or -R ４０ -B ６ - and two E ２３ may 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 -R４０ -B ６ - and E ２５ When there are two or more, there are two or more E ２５ may be the same or different, E ２６ is a single bond or -R ４０ -B ６ - and 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, 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 3, e2 is an integer from 0 to 3, and e1+e2 is an integer from 1 to 6, 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=x1.

[0051] 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 the present compound and of further improving the 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.

[0052] Z １ The ring structure in １ 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.

[0053] 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 the present compound. Ｅ２ The number of carbon atoms in the alkyl group moiety of the acyloxy 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 the compound 1. g4 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 the compound and further improved abrasion resistance and fingerprint removability of the surface layer.

[0054] Said L １ Other examples of the group include groups represented by any of the following formulae (E11) to (E17).

[0055] ...Formula (E11) -E １ -C(R Ｅ２ ) ３－ｅ３ (-E ２２ -E Ｇ ) ｅ３ ...Formula (E12) -E ２ -N (-E ２３ -E Ｇ ) ２ ...Formula (E13) -E ３ -Z １ (-E ２４ -E Ｇ ) ｅ４ ...Formula (E14) -E ２ -Si(R Ｅ３ ) ３－ｅ３ (-E ２５ -E Ｇ ) ｅ３ ...Formula (E15) -E １ -E ２６ -E Ｇ ...Formula (E16) -E １ -CH(-E ２２ -)-Si(R Ｅ３ ) ３－ｅ５ (-E ２５ -E Ｇ ) ｅ５ ...Formula (E17)

[0056] However, in the formulas (E11) to (E17), E １ , E ２ or E ３ side is R in formula (1) ２ Connect with E ２２ , E ２３ , E ２４ , E ２５ or E ２６ Side is R ３ Connect to E Ｇ is expressed by the following formula (E Ｇ ) and L １ has 2 or more E Ｇ may be the same or different. The symbols other than G are the same as those in formulas (E1) to (E7). -Si(R ２３ ) ３－ｋ (-E ３ -) ｋ Formula (E Ｇ ) where the formula (E Ｇ ) in which the Si side is E ２２ , E ２３ , E ２４ , E ２５ or E ２６ Connect to E ３ Side is R ３ Connect to R ２３ is an alkyl group. ３ 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 ３ 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. ２４ is an alkyl group, a phenyl group, or an alkoxy group, and two R ２４may 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.

[0057] E ３ 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 the present compound 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 the present compound. 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 the present compound. ２４ In view of excellent storage stability of the present compound, 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. p is preferably 0 or 1.

[0058] R ３ Is, L １ The atom bonded to R may be an ethereal oxygen atom, and an alkylene group may have an ethereal oxygen atom between carbon atoms, ３ If there are multiple R ３ may be the same or different. ３ is preferably a group represented by the following formula (g5): *-(O) ａ４ - (R ｇ１ O) ａ５ -R ｇ２ -** ... (g5) where R ｇ１ is an alkylene group having 1 to 12 carbon atoms, and a plurality of R ｇ１ may be the same or different, R ｇ２ represents an alkylene group having 1 to 18 carbon atoms, a4 represents 0 or 1, a5 represents an integer of 0 or more, * represents L １ is the bond to be bonded, and ** is T １is the bond that bonds to

[0059] When a4 is 0, the atom having the bond * is a carbon atom, and when a3 is 1, the atom having the bond * is an oxygen atom. In this compound, a3 may be either 0 or 1, and may be appropriately selected from the viewpoint of synthesis, etc. a5 is R ｇ１ R is the number of repetitions of O, and from the viewpoint of durability as a surface layer, it is preferably 0 to 6, more preferably 0 to 3, and even more preferably 0 to 1. ｇ１ The alkylene group in R 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. ｇ２ The alkylene group may be a linear or branched alkylene group having 1 to 18 carbon atoms, preferably an alkylene group having 1 to 12 carbon atoms, more preferably an alkylene group having 1 to 8 carbon atoms, still more preferably an alkylene group having 2 to 6 carbon atoms, and particularly preferably an alkylene group having 2 to 3 carbon atoms. The alkylene group is preferably a linear alkylene group.

[0060] T １ is -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ It is. ａ１ is a hydroxyl group or a hydrolyzable group, and R ａ１ If there are multiple R ａ１ may be the same or different, R ａ１１ is a non-hydrolyzable group, and R ａ１１ If there are multiple R ａ１１ may be the same or different. z1 is an integer of 0 to 3, and when there are multiple z1, the multiple z1 may be the same or different, provided that at least one of z1 is an integer of 1 to 3.

[0061] R ａ１is 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). This compound A1 is T １ By containing one or more of the above, the surface layer has excellent abrasion resistance after formation.

[0062] R ａ１ Examples of the hydrolyzable group in R include an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanate group (-NCO). The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. The acyl group is preferably an acyl group having 1 to 6 carbon atoms. The acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms. ａ１ In view of ease of production of the present compound, R is preferably an alkoxy group having 1 to 4 carbon atoms or a halogen atom. ａ１ In terms of the alkoxy group, an alkoxy group having 1 to 4 carbon atoms is preferred, as it provides excellent storage stability for the compound and suppresses outgassing during the reaction, an ethoxy group is particularly preferred from the standpoint of long-term storage stability, and a methoxy group is particularly preferred from the standpoint of shortening the hydrolysis reaction time. Also, as the halogen atom, a chlorine atom is particularly preferred.

[0063] R ａ１１ The non-hydrolyzable group is a hydrogen atom or a monovalent hydrocarbon group. Examples of the hydrocarbon group include an alkyl group, a cycloalkyl group, an alkenyl group, and an allyl group, and from the viewpoint of ease of production, an alkyl group is preferred. From the viewpoint of ease of production, the number of carbon atoms in the hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.

[0064] One T １ Within, R ａ１ The number z1 may be 1 to 3, and from the viewpoint of adhesion to the substrate, 2 or 3 is preferable, and 3 is more preferable. １ Specific examples of -Si(OCH ３ )３ , -SiCH ３ (OCH ３ ) ２ , -Si(OCH ２ CH ３ ) ３ , -SiCl ３ , -Si(OCOCH ３ ) ３ , —Si(NCO) ３ From the viewpoint of ease of handling in production, -Si(OCH ３ ) ３ is particularly preferred.

[0065] T in one molecule of Compound 1 １ The number x1 may be 1 to 20, and from the viewpoints of ease of synthesis and ease of handling of compound A1, x1 is preferably 1 to 12, more preferably 1 to 6. １ If there is a T １ may have the same structure as each other or may have different structures.

[0066] Specific examples of Compound 1 include the following: wherein each n is independently an integer of 1 or more, and each n1 is independently an integer of 1 to 3.

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] <Compound 2> Compound 2 is a compound represented by the following formula (2): (T ３ -R ９ ) ｘ３ -L ３ -R ８ -Q ３ -R ７ -R ｆ - (ORｆ２ ) ｙ２ -R ４ -Q ２ -R ５ -L ２ - (R ６ -T ２ ) ｘ２ ...Equation (2) where the symbols in the equation are as defined above.

[0074] R ｆ is a fluoroalkylene group having 1 to 6 carbon atoms. The fluoroalkylene group is R ｆ１ The same applies to the preferred embodiments. ｆ２ and (OR ｆ２ ) ｙ２ is R of Compound 1 ｆ , and (OR ｆ１ ) ｙ１ Corresponds to R ｆ２ and (OR ｆ２ ) ｙ２ The structure of each independently represents R ｆ , and (OR ｆ１ ) ｙ１ The same applies to the preferred embodiments. ３ -R ９ ) ｘ３ and (R ６ -T ２ ) ｘ２ is the (R ３ -T １ ) ｘ１ Corresponding to (T ３ -R ９ ) ｘ３ and (R ６ -T ２ ) ｘ２ The structure of each independently represents (R ３ -T １ ) ｘ１ The same applies to the preferred embodiments. ４ and R ７ is R of Compound 1 １ Corresponds to R ４ and R ７ The structure of each independently represents R １ The same applies to the preferred embodiments. ２ and Q ３ is the Q of Compound 1１ Corresponds to Q ２ and Q ３ The structures of each independently represent Q １ The same applies to the preferred embodiments. ５ and R ８ is R of Compound 1 ２ Corresponds to R ５ and R ８ The structure of each independently represents R ２ The same applies to the preferred embodiments. ２ and L ３ is L of Compound 1 １ Corresponds to L ２ and L ３ The structures of each independently represent L １ The same applies to the preferred embodiments.

[0075] Specific examples of Compound 2 include the following: wherein each n is independently an integer of 1 or more.

[0076]

[0077] (Method for Producing Compounds 1 and 2) The method for producing Compounds 1 and 2 is not particularly limited, but from the viewpoint of obtaining a high yield, a method of subjecting a compound represented by the following formula (5) or a compound represented by the following formula (6) to a hydrosilylation reaction with Compound 101 represented by the following formula (101) is preferred. １ - (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２ -L １ - (R Ｃ１ -CH=CH ２ ) ｘ１ ...Formula (5) (CH ２ =CH-R Ｃ３ ) ｘ３ -L ３ -R ８ -Q ３ -R ７ -R ｆ - (OR ｆ２ ) ｙ２ -R ４ -Q ２ -R５ -L ２ - (R Ｃ２ -CH=CH ２ ) ｘ２ ...Formula (6) HSiR ａ１ ｚ１ R ａ１１ ３－ｚ１ ...Equation (101) where R Ｃ１ , R Ｃ２ and R Ｃ３ are each independently L １ , L ２ or L ３ an alkylene group which may have an ether oxygen atom at the terminal or between carbon atoms of the R Ｃ１ , R Ｃ２ or R Ｃ３ If there are multiple R Ｃ１ , R Ｃ２ or R Ｃ３ may be the same or different from each other independently, and the other symbols are the same as the symbols in the formula (1) or (2), and the preferred embodiments are also the same. Ｃ１ -CH=CH ２ is R in formula (1) after the reaction. ３ corresponds to R Ｃ１ -CH=CH ２ After the reaction, R in formula (2) ６ Corresponding to CH ２ =CH-R Ｃ３ After the reaction, R in formula (2) ９ Corresponds to.

[0078] Compounds 5 and 6 can be produced, for example, by coupling a compound represented by the following formula (3) or a compound represented by the following formula (4) with a compound represented by the following formula (102) in the presence of a transition metal catalyst and a ligand. １ - (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２１ -D １ ...Formula (3) D ３ -R ８１ -Q ３ -R ７ -Rｆ - (OR ｆ２ ) ｙ２ -R ４ -Q ２ -R ５１ -D ２ ...Formula (4) D １１ -R ２２ -L １ - (R Ｃ１ -CH=CH ２ ) ｘ１ ...Equation (102) where D １ , D ２ and D ３ are each independently a halogen atom; １１ is R ２２ an atomic group containing any one atom selected from the group consisting of Mg, Zn, Sn, B, Si, and Al, directly bonded to R ２２ is a single bond or an alkylene group, and the other symbols are as described above. However, when formula (102) is reacted with formula (4), L in formula (102) １ Is L ２ or L ３ corresponds to R Ｃ１ is R Ｃ２ or R Ｃ３ and x1 corresponds to x2 or x3. After the reaction, -R ２１ -R ２２ - is -R ２ corresponds to -R ５１ -R ２２ - is -R ５ corresponds to -R ８１ -R ２２ - is -R ８ Corresponds to -.

[0079] The transition metal catalyst is, for example, CuCl ２ Examples of the ligand include copper salts such as those described above. Examples of the ligand include pi ligands in which a carbon-carbon multiple bond, such as 1-phenyl-1-propyne, is coordinated to a metal atom. Compound 102 can be synthesized, for example, by referring to the method described in International Publication No. 2021 / 054413.

[0080] Compounds 3 and 4 are novel compounds in which a ring structure is bonded to at least one end of a fluoropolyether chain. Compounds 3 and 4 are suitable for producing Compounds 1 and 2. １ - (OR ｆ１ ) ｙ１ -R １ -Q １ -R ２１ -D １ ...Formula (3) D ３ -R ８１ -Q ３ -R ７ -R ｆ - (OR ｆ２ ) ｙ２ -R ４ -Q ２ -R ５１ -D ２ ...Equation (4) where the symbols in the equation are as described above, and D １ , D ２ and D ３ In terms of reactivity, the halogen atom in is preferably a chlorine atom, a bromine atom, or an iodine atom, and is particularly preferably an iodine atom.

[0081] R ２１ is a single bond, the compound １ D １ It has a structure directly bonded to R ２１ is a divalent group, R ２１ is, for example, -NR Ｎ R is —C(═O)—, —OC(═O)—, —C(═O)—, or an alkylene group. ２ When Q is an alkylene group, １ -O-, -S-, or -C(=O)NR at the end of the bond or between the carbon-carbon bonds Ｎ -, -NR Ｎ may have -C(=O)-, -C(=O)O-, -OC(=O)-, or -C(=O)-, D １ -NR at the end of the bond Ｎ From the viewpoint of ease of synthesis, R ２１is preferably an alkylene group, and particularly preferably a methylene group. ５１ and R ８１ is R of compound 3 ２１ The same applies to the preferred embodiments.

[0082] D １ is a halogen atom. From the viewpoint of reactivity, D １ is preferably a chlorine atom, a bromine atom, or an iodine atom, and is particularly preferably an iodine atom. ２ and D ３ is D of compound 3 １ The same applies to the preferred embodiments.

[0083] (Method for Producing Compounds 3 and 4) Examples of methods for synthesizing Compounds 3 and 4 include (I) a method of introducing a reactive group into the end of a fluoropolyether chain and then subjecting the reactive group to an addition reaction with a compound having a ring structure and a substituent that undergoes an addition reaction with the reactive group, and (II) a method of subjecting a compound represented by the following formula (7) or a compound represented by the following formula (8) to a radical cyclization reaction with a diene in the presence of a radical initiator. １ - (OR ｆ１ ) ｙ１ -D １ ...Formula (7) D ３ -R ｆ - (OR ｆ２ ) ｙ２ -D ２ ...Equation (8) where the symbols in the equation are as described above.

[0084] Compounds 7 and 8 can be produced, for example, by the production method described in WO 2019 / 163282. Examples of the radical initiator include azo compounds such as 2,2-azobis(2-methylbutyronitrile) and azobisisobutyronitrile, and organic peroxides.

[0085] An example of the diene is a compound represented by the following formula (103). For example, when compound 103 and compound 7 are used, a mixture of compounds 3A and 3B represented by the following formulas (3A) and (3B) may be obtained as the reaction product. Both compounds 3A and 3B can be used as compound 3. Compounds 3A and 3B may be used after separation and purification, or may be used as a mixture containing two types of compound 3. CH ２ =CH-R １０３ -CH=CH ２ ...Equation (103) where R １０３ is an ether oxygen or -NR Ｎ It is an alkylene group which may have -, and from the viewpoint of ease of synthesis, it is preferable that the main chain contains 3 to 6 atoms.

[0086] ...Formula (3A) ...Formula (3B)

[0087] Also, the group Q in compound 3 １ When A is an aryl group, compound 3 may be produced by coupling reaction of compound 7 with compound 104 represented by the following formula (104) in the presence of a suitable transition metal catalyst and a suitable ligand. １ - (OR ｆ１ ) ｙ１ -R １ -D １３ ...Formula (7) D １４ -Q １ -R ２１ -D １ ...Equation (104) where D １ is a halogen, and D １３ is R １ an atomic group containing any one atom selected from the group consisting of Mg, Zn, Sn, B, Si, and Al, directly bonded to D; １４ is a halogen atom or a leaving group such as -OTs, where Ts is a tosyl group.

[0088] [Fluorine-Containing Compound-Containing Composition] The fluorine-containing compound-containing composition of the present invention (hereinafter also referred to as "the composition") contains one or more fluorine-containing ether compounds which are the present compounds, and a fluorine-containing ether compound other than the present compounds. The composition may contain, for example, both Compound 1 and Compound 2 as the present compounds. Furthermore, the composition may contain both Compound 1 synthesized from Compound 3A and Compound 1 synthesized from Compound 3B. Note that the composition does not contain a liquid medium, which will be described later.

[0089] The other fluorine-containing ether compounds include both compounds that are inevitably contained and compounds that are used in combination depending on the application, etc.

[0090] Compounds that can be used in combination with the present compound include known fluorine-containing ether compounds and fluorine-containing oils.

[0091] Examples of fluorine-containing oils include polytetrafluoroethylene (PTFE), ethylene-chlorotrifluoroethylene copolymer (ECTFE), polyvinylidene fluoride (PVDF), polyvinyl fluoride (PVF), and polychlorotrifluoroethylene (PCTFE).

[0092] Further, examples of known fluorine-containing ether compounds include fluorine-containing ether compounds commercially available as surface treatment agents. When the present composition contains a known fluorine-containing ether compound, new effects such as complementing the properties of the present compound may be exhibited. Examples of known fluorine-containing ether compounds include those described in the following documents: perfluoropolyether-modified aminosilanes described in JP-A-11-029585, silicon-containing organic fluorine-containing polymers described in JP-A-2874715, organosilicon compounds described in JP-A-2000-144097, perfluoropolyether-modified aminosilanes described in JP-A-2000-327772, fluorinated siloxanes described in JP-A-2002-506887, organosilicon compounds described in JP-A-2008-534696, fluorinated modified hydrogen-containing polymers described in JP-A-4138936, compounds described in U.S. Patent Application Publication No. 2010 / 0129672, WO 2014 / 126064 and JP-A-2014-070163, Organosilicon compounds described in WO 2011 / 060047 and WO 2011 / 059430; fluorine-containing organosilane compounds described in WO 2012 / 064649; fluorooxyalkylene group-containing polymers described in JP 2012-72272 A; fluorine-containing ether compounds described in WO 2013 / 042732, WO 2013 / 121984, WO 2013 / 121985, WO 2013 / 121986, WO 2014 / 163004, JP 2014-080473 A, WO 2015 / 087902, WO 2017 / 038830, WO 2017 / 038832, and WO 2017 / 187775; perfluoro(poly)ether-containing silane compounds described in JP 2014-218639 A, WO 2017 / 022437, WO 2018 / 079743, and WO 2018 / 143433;Fluoropolyether group-containing polymer-modified silanes described in Japanese Patent Application Laid-Open No. 2015-199906, Japanese Patent Application Laid-Open No. 2016-204656, Japanese Patent Application Laid-Open No. 2016-210854, and Japanese Patent Application Laid-Open No. 2016-222859 WO 2018 / 216630, WO 2019 / 039226, WO 2019 / 039341, WO 2019 / 039186, WO 2019 / 044479, Japanese Patent Application Laid-Open No. 2019-44158, WO 2019 / 044479, and WO 2019 / 163282 Fluorine-containing ether compounds described in. Commercially available fluorine-containing compounds include the KY-100 series (KY-178, KY-185, KY-195, etc.) manufactured by Shin-Etsu Chemical Co., Ltd., the SURECO AF series such as SURECO (registered trademark) 2101S manufactured by AGC Inc., and OPTOOL (registered trademark) DSX, OPTOOL (registered trademark) AES, OPTOOL (registered trademark) UF503, and OPTOOL (registered trademark) UD509 manufactured by Daikin Industries, Ltd.

[0093] When the present compound is combined with a known fluorinated ether compound in the present composition, the content ratio may be adjusted appropriately depending on the application, etc. The content ratio of the present compound in the present composition is preferably 10 to 90 mass%, more preferably 20 to 80 mass%, and even more preferably 25 to 75 mass%. By setting the content within the above range, the properties of the present compound can be fully exhibited, and the properties of the fluorinated ether compound used in combination can also be fully obtained.

[0094] Examples of compounds that are inevitably contained include fluorine-containing ether compounds produced as by-products in the production process of the present compound (hereinafter also referred to as "by-product fluorine-containing ether compounds"). Examples of by-product fluorine-containing ether compounds include unreacted fluorine-containing compounds (e.g., Compound 3 or Compound 4) and fluorine-containing ether compounds in which part of the allyl groups has been isomerized to an inner olefin during hydrosilylation in the production of the present compound.

[0095] When the composition contains a by-produced fluorinated ether compound, the by-produced fluorinated ether compound can be removed by purification, but may be contained in the composition to the extent that the properties of the compound can be fully exhibited. This simplifies the purification process of the by-produced fluorinated ether compound. When a known fluorinated ether compound is not combined, the content of the compound in the composition is preferably 60% by mass or more but less than 100% by mass, more preferably 70% by mass or more but less than 100% by mass, and particularly preferably 80% by mass or more but less than 100% by mass. The content of the by-produced fluorinated ether compound in the composition is preferably more than 0% by mass but less than 40% by mass, more preferably more than 0% by mass but less than 30% by mass, and particularly preferably more than 0% by mass but less than 20% by mass. When the content of the compound and the content of the by-produced fluorinated ether compound are within the above ranges, the initial water and oil repellency, abrasion resistance, fingerprint stain removability, light fastness, and chemical resistance of the surface layer are even more excellent.

[0096] Inevitably contained compounds include additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reaction of hydrolyzable silyl groups. Examples of acid catalysts include hydrochloric acid, nitric acid, acetic acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid. Examples of basic catalysts include sodium hydroxide, potassium hydroxide, and ammonia. The content of these catalysts in the composition is preferably 0 to 9.999% by mass, and particularly preferably 0 to 0.99% by mass.

[0097] [Surface Treatment Agent] A surface treatment agent containing the present fluorinated ether compound (hereinafter also referred to as the present surface treatment agent) is suitably used in applications where 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) must be maintained for a long period of time, such as for members constituting the surfaces of touch panels that are touched with fingers, eyeglass lenses, and displays of wearable devices.

[0098] [Coating Liquid] The coating liquid of the present invention (hereinafter also referred to as the present coating liquid) contains the present fluorinated ether compound and a liquid medium. The present coating liquid may be in liquid form, and may be a solution or a dispersion. The present coating liquid may contain the present fluorinated ether compound, and may contain impurities such as by-products produced in the production process of the present fluorinated ether compound. The concentration of the present fluorinated ether compound in the present coating liquid is preferably 0.001 to 40% by mass, preferably 0.01 to 20% by mass, and more preferably 0.1 to 10% by mass.

[0099] 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. Examples of the fluorine-containing organic solvent include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, and fluoroalcohols. As the fluorinated alkane, a compound having 4 to 8 carbon atoms is preferred. Commercially available products include, for example, C ６ F １３ H (manufactured by AGC, Asahiklin (registered trademark) AC-2000), C ６ F １３ C ２ H ５ (ASAHIKLIN (registered trademark) AC-6000, manufactured by AGC), C ２ F ５ CHFCHFCF ３ (Vertrel (registered trademark) XF, manufactured by Chemours) and the like. Examples of fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene. Preferred fluoroalkyl ethers are compounds having 4 to 12 carbon atoms. Commercially available products include, for example, 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 F９ 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). Fluorinated alkylamines include, for example, perfluorotripropylamine and perfluorotributylamine. Fluoroalcohols include, for example, 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol. Non-fluorinated organic solvents are preferably compounds consisting of only hydrogen atoms and carbon atoms, and compounds consisting of only hydrogen atoms, carbon atoms, and oxygen atoms, and examples of such non-fluorinated organic solvents include hydrocarbon organic solvents, alcohol organic solvents, ketone organic solvents, ether organic solvents, and ester organic solvents. The coating liquid preferably contains 75 to 99.999% by mass of the liquid medium, more preferably 85 to 99.99% by mass, and particularly preferably 90 to 99.9% by mass.

[0100] In addition to the present fluorine-containing ether compound and the liquid medium, the present coating liquid may contain other components as long as the effects of the present invention 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 coating liquid is preferably 10% by mass or less, more preferably 1% by mass or less.

[0101] The total concentration of the present fluorinated ether compound and other components in the present coating liquid (hereinafter also referred to as solids concentration) is preferably 0.001 to 40 mass%, more preferably 0.01 to 20 mass%, still 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.

[0102] [Article] Figure 1 is a schematic cross-sectional view showing an example of an article of the present invention. The first article of the present invention 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 a silicon-containing oxide and the surface layer 22 contains a condensate of the present composition.

[0103] The material and shape of the substrate 12 in the first article 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 constitute 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.

[0104] 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.

[0105] 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 １ is dehydrated and condensed to form Si—O—Si bonds with the underlayer 14, forming a surface layer 22 with excellent abrasion resistance.

[0106] The content of silicon oxide in the underlayer 14 may be 65% by mass or more, preferably 80% by mass or more, more preferably 85% by mass or more, and even more 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.

[0107] From the viewpoint of 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 present composition, improving wear resistance.

[0108] 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 1100 ppm by mass, more preferably 50 to 1100 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 2500 ppm by mass, more preferably 15 to 2000 ppm by mass, and even more preferably 20 to 1000 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 mass ppm to 800 mass ppm, more preferably 0.04 mass ppm to 600 mass ppm, and even more preferably 0.7 mass ppm to 200 mass ppm. 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, from the viewpoint of the wear resistance of the surface layer 22. When the underlayer 14 contains alkaline earth metal elements, the total content thereof, expressed as the ratio of the molar concentration of the total alkaline earth metal elements to the molar concentration of silicon, is preferably 0.005 to 5, more preferably 0.005 to 2, and even more preferably 0.007 to 2, from the viewpoint of the wear resistance of the surface layer 22. Examples of alkaline earth metal elements include lithium, sodium, potassium, rubidium, and cesium.

[0109] From the viewpoint of improving the adhesiveness of the composition 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 particular, 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 preferably 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 the alkali metal atoms is preferably 4.0×10 or more. ２２ atoms / cm ３ It is preferable that:

[0110] The thickness of the underlayer 14 is preferably 1 to 200 nm, and particularly preferably 2 to 20 nm. If the thickness of the underlayer 14 is at least the lower limit of the above range, the underlayer 14 is likely to sufficiently improve adhesion. If the thickness of the underlayer 14 is at most the upper limit of the above range, the underlayer 14 itself will have high abrasion resistance. 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 profilometer, etc.

[0111] The underlayer 14 can be formed, for example, by depositing a deposition material having a desired composition for the underlayer 14 on the surface of the substrate 12. One example of the deposition method is vacuum deposition. Vacuum deposition is a method in which the deposition material is evaporated in a vacuum chamber and attached to the surface of the substrate 12. The temperature during deposition (for example, when using a vacuum deposition device, the temperature of the boat on which the deposition material is placed) is preferably 100 to 3000°C, and particularly preferably 500 to 3000°C. The pressure during deposition (for example, when using a vacuum deposition apparatus, the absolute pressure in a tank in which the deposition material is placed is preferably 1 Pa or less, and particularly preferably 0.1 Pa or less. When forming the underlayer 14 using a deposition material, one deposition material may be used, or two or more deposition materials containing different elements may be used. Methods for evaporating the deposition material include a resistance heating method in which the deposition material is melted and evaporated on a resistance heating boat made of a high-melting-point metal, and an electron gun method in which the deposition material is irradiated with an electron beam to directly heat the deposition material and melt and evaporate the surface. The electron gun method is preferred as a method for evaporating the deposition material because it can be heated locally and therefore high-melting-point substances can be evaporated, and because areas not irradiated by the electron beam are at low temperatures, there is no risk of reaction with the container or the inclusion of impurities. The deposition material used in the electron gun method is preferably a molten granular or sintered material because it is less likely to scatter even when an air current is generated.

[0112] The surface layer 22 on the underlayer 14 contains a condensate of a compound contained in the present composition. Condensates of the present compound include those formed by hydrolysis of a hydrolyzable silyl group in a compound contained in the present composition to form a silanol group (Si—OH), which then undergoes an intermolecular condensation reaction to form an Si—O—Si bond, and those formed by condensation of a silanol group in the present compound with a silanol group or a Si—OM group (where M is an alkali metal element) on the surface of the underlayer 14 to form an Si—O—Si bond. The surface layer 22 may also contain a condensate of a fluorine-containing compound other than the compound contained in the present composition. That is, the surface layer 22 contains a fluorine-containing compound having a reactive silyl group in a state in which some or all of the reactive silyl groups of the fluorine-containing compound have undergone a condensation reaction.

[0113] The thickness of the surface layer 22 is preferably 1 to 100 nm, and particularly 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.

[0114] The second article of the present invention is an article 20 having, in this order, a substrate 10 with an undercoat layer and a surface layer 22, in which the substrate 10 with an undercoat layer contains an oxide containing silicon, and the surface layer 22 contains a condensate of the present composition.

[0115] 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.

[0116] [Method for Producing an Article] The method for producing an article according to the present invention is a method for forming a surface layer by a dry coating method or a wet coating method using the fluorinated ether compound, the surface treatment agent, or the coating liquid.

[0117] The present fluorine-containing ether compound and the present surface treatment agent can be used directly in a dry coating method. Furthermore, the present composition and the present surface treatment agent are suitable for forming a surface layer with excellent adhesion by a dry coating method. Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferred because it suppresses decomposition of the present composition and because the equipment is simple. For vacuum deposition, a pellet-shaped material in which the present composition 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 the present composition is supported can be produced by impregnating a porous metal body with a solution of the present composition, drying it, and removing the liquid medium. The present coating liquid can be used as the solution of the present composition.

[0118] The present coating liquid can be suitably used for 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.

[0119] To improve the abrasion resistance of the surface layer, an operation to promote the reaction between the composition and the substrate may be performed as needed. 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 moist 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 or wiping it off with a cloth soaked in the solvent.

[0120] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. In the following, "%" means "% by mass" unless otherwise specified. Examples 1 to 5 are examples, and Examples 6 and 7 are comparative examples.

[0121] [Example 1] (Synthesis Example 1-1) The following compound 1-1 was obtained according to the synthesis method described in Example 2-2 of WO 2019 / 163282. CF ３ -O-(CF ２ CF ２ O-CF ２ CF ２ CF ２ CF ２ O) ｎ２ CF ２ CF ２ O-CF ２ CF ２ CF ２ -I Formula 7-1 where the average value of the repeating unit n2 is 13.

[0122] (Synthesis Example 1-2) The following compound 1-2 was obtained according to the synthesis method described in Example 2 of WO 2021 / 054413.

[0123] ...Formula 1-2

[0124] Synthesis Example 1-3: 5 g of compound 1-1 obtained in Synthesis Example 1-1, 0.36 g of diallyl ether, 0.23 g of 2,2-azobis(2-methylbutyronitrile), and 7.2 g of AC-6000 were placed in a 50 mL recovery flask and stirred at 80°C for 3 hours. The temperature inside the recovery flask was brought to 25°C, acetone was added, the liquid was separated, the lower phase was separated, and the solvent was removed. The obtained crude product was purified by silica gel column chromatography to obtain 2.4 g of compound 1-3.

[0125] ...Formula (1-3)

[0126] NMR spectrum of compound 3-1; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 4.1 to 4.0 (2H), 3.8 to 3.6 (2H), 3.0 to 2.7 (2H), 2.6 to 2.3 (2H), 2.3 to 2.1 (2H) １９H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −111.0 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n3: 13.

[0127] Synthesis Example 1-4 In a 20 mL recovery flask, 2 g of Compound 1-3 obtained in Synthesis Example 1-3, 4.9 mg of 1-phenyl-1-propyne, CuCl ２ 2.8 mg of 1-4, 4 g of AE-3000, and 0.26 g of compound 1-2 obtained in Synthesis Example 1-2 were placed in a flask and stirred at 40°C for 20 hours. The temperature inside the recovery flask was brought to 25°C, hydrochloric acid was added, the liquids were separated, the organic layer was recovered, and the solvent was distilled off. The obtained crude product was purified using a silica gel column to obtain 1.3 g of compound 1-4.

[0128] ...Formula (1-4)

[0129] NMR spectrum of compounds 1-4; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 5.9-5.7 (3H), 5.1-4.9 (6H), 4.1-4.0 (2H), 3.8-3.6 (2H), 2.5-1.1 (14H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.7 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n4: 13.

[0130] Synthesis Example 1-5: 1 g of compound 1-4 obtained in Synthesis Example 1-4, 0.11 g of trimethoxysilane, 1.3 mg of aniline, 1 g of AC-6000, and 3.6 mg of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were placed in a 10 mL recovery flask and stirred at 40° C. The solvent was distilled off under reduced pressure, yielding 1.1 g of compound (I).

[0131] Formula (I)

[0132] NMR spectrum of compound (I); １H-NMR (400MHz, Chloroform-d) δ (ppm): 4.1-4.0 (2H), 3.8-3.6 (2H), 3.6 (27H), 2.6-0.8 (20H), 0.6 (6H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.5 to −114.7 (2F), −124.8 (52F), −125.4 (2F) Average value of n5: 13.

[0133] Example 2 Synthesis Example 2-1 4.2 g of Compound 2-1 was obtained in the same manner as in Synthesis Example 1-3, except that the diallyl ether in Synthesis Example 1-3 was changed to 0.21 g of 1,6-heptadiene.

[0134] ...Formula (2-1)

[0135] NMR spectrum of compound 2-1; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.5-3.0 (2H), 2.6-1.3 (10H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −111.0 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n6: 13.

[0136] Synthesis Example 2-2 1.6 g of Compound 2-2 was obtained in the same manner as in Synthesis Example 1-4, except that Compound 1-3 in Synthesis Example 1-4 was changed to Compound 2-1.

[0137] ...Formula (2-2)

[0138] NMR spectrum of compound 2-2; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 5.9-5.7 (3H), 5.1-4.9 (6H), 2.5-1.1 (20H) １９H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.7 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n7: 13.

[0139] Synthesis Example 2-3 1.1 g of compound (II) was obtained in the same manner as in Synthesis Example 1-5, except that compound 1-4 in Synthesis Example 1-5 was changed to compound 2-2.

[0140] ...Formula (II)

[0141] NMR spectrum of compound (II); １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.6 (27H), 2.6-0.8 (26H), 0.6 (6H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.5 to −114.7 (2F), −124.8 (52F), −125.4 (2F) Average value of n8: 13.

[0142] Example 3 Synthesis Example 3-1 2.6 g of Compound 3-1 was obtained in the same manner as in Synthesis Example 1-3, except that the diallyl ether in Synthesis Example 1-3 was changed to 0.28 g of 1,5-hexadiene.

[0143] ...Formula (3-1)

[0144] NMR spectrum of compound 3-1; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.2-2.7 (2H), 2.5-1.9 (8H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.4 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n9: 13.

[0145] Synthesis Example 3-2 1.4 g of compound 3-2 was obtained in the same manner as in Synthesis Example 1-4, except that compound 1-3 in Synthesis Example 1-4 was changed to compound 3-1.

[0146] ...Formula (3-2)

[0147] NMR spectrum of compound 5-3; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 5.9-5.7 (3H), 5.1-4.9 (6H), 2.5-1.1 (18H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.2 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n10: 13.

[0148] Synthesis Example 3-3 1.1 g of compound (III) was obtained in the same manner as in Synthesis Example 1-5, except that compound 1-4 in Synthesis Example 1-5 was changed to compound 3-2.

[0149] ...Formula (III)

[0150] NMR spectrum of compound (III); １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.6 (27H), 2.6-0.8 (24H), 0.6 (6H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.1 to −114.6 (2F), −124.8 (52F), −125.4 (2F) Average value of n11: 13.

[0151] Example 4 Synthesis Example 4-1 2.7 g of Compound 4-1 was obtained in the same manner as in Synthesis Example 1-3, except that the diallyl ether in Synthesis Example 1-3 was changed to 0.36 g of 1,7-octadiene.

[0152] ...Formula (4-1)

[0153] NMR spectrum of compound 4-1; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.1 to 2.7 (2H), 2.5 to 1.2 (12H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.6 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n12: 13.

[0154] Synthesis Example 4-2 1.3 g of compound 4-2 was obtained in the same manner as in Synthesis Example 1-4, except that compound 1-3 in Synthesis Example 1-4 was changed to compound 4-1.

[0155] ...Formula (4-2)

[0156] NMR spectrum of compound 4-2; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 5.9-5.7 (3H), 5.1-4.9 (6H), 2.5-1.1 (22H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.4 to −114.9 (2F), −124.8 (52F), −125.4 (2F) Average value of n13: 13.

[0157] Synthesis Example 4-3 1.0 g of compound (IV) was obtained in the same manner as in Synthesis Example 1-5, except that compound 1-4 in Synthesis Example 1-5 was changed to compound 4-2.

[0158] ...Formula (IV)

[0159] NMR spectrum of compound (IV); １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.6 (27H), 2.6-0.8 (28H), 0.6 (6H) １９H-NMR (376 MHz, Chloroform-d) δ (ppm): −55.2 (3F), −82.3 (54F), −87.8 (54F), −89.9 (2F), −110.2 to −114.6 (2F), −124.8 (52F), −125.4 (2F) Average value of n14: 13.

[0160] Example 5 The above compound (II) and compound (III) were mixed in a mass ratio of 50:50 to obtain a composition of Example 5.

[0161] [Example 6] The following compound (VI) was obtained according to the synthesis method described in the examples of JP 2014-218639 A, where the average value of n15 is 13.

[0162] Formula (VI)

[0163] [Example 7] The following (VII) was obtained according to the synthesis method described in the examples of WO 2017 / 038830, where the average value of n16 is 13.

[0164] ...Formula (VII)

[0165] [Production and Evaluation of Articles] Substrates were surface-treated using the compositions and compounds obtained by the above-mentioned production methods to obtain articles. The surface treatment methods used in each example were the dry coating method and the wet coating method described below. Chemically strengthened glass was used as the substrate. The obtained articles were evaluated by the following methods. The results are shown in the table.

[0166] Dry coating was carried out using a vacuum deposition apparatus (VTR350M, manufactured by ULVAC) (vacuum deposition method). 0.5 g of each compound was placed in a molybdenum boat in the vacuum deposition apparatus, and the inside of the vacuum deposition apparatus was heated to 1×10 －３The chamber was evacuated to a pressure of 10 Pa or less. The boat on which the compound was placed was heated at a temperature increase rate of 10°C / min or less, and when the deposition rate measured by a quartz crystal oscillator film thickness meter exceeded 1 nm / sec, the shutter was opened to start film formation on the surface of the substrate. When the film thickness reached approximately 50 nm, the shutter was closed to terminate film formation on the surface of the substrate. The substrate on which the compound had been deposited was heat-treated at 200°C for 30 minutes and washed with dichloropentafluoropropane (AK-225, manufactured by AGC) to obtain an article having a surface layer on the surface of the substrate.

[0167] [Wet Coating Method] Each compound and C as a medium ４ F ９ O.C. ２ H ５ (Novec (registered trademark) 7200, manufactured by 3M Company) was mixed to prepare a coating solution with a solids concentration of 0.05%. A substrate was dipped into the coating solution, allowed to stand for 30 minutes, and then pulled out (dip coating method). The coating film was dried at 200°C for 30 minutes and washed with AK-225 to obtain an article having a surface layer on the surface of the substrate.

[0168] (Evaluation Method) <Contact Angle Measurement Method> The contact angle of approximately 2 μL of distilled water or n-hexadecane placed on the surface of the surface layer was measured using a contact angle measurement device (DM-500, manufactured by Kyowa Interface Science Co., Ltd.). Measurements were taken at five different points on the surface of the surface layer, and the average value was calculated. The 2θ method was used to calculate the contact angle.

[0169] <Initial Contact Angle> The initial water contact angle and n-hexadecane contact angle of the surface layer were measured by the above-mentioned measurement method. The evaluation criteria are as follows: A (Excellent): 115 degrees or more. B (Good): 110 degrees or more and less than 115 degrees. C (Fair): 100 degrees or more and less than 110 degrees. D (Fail): Less than 100 degrees.

[0170] <Abrasion Resistance (Steel Wool)> For the surface layer, a reciprocating traverse tester (manufactured by KNT Corporation) was used in accordance with JIS L0849:2013 (ISO 105-X12:2001) to reciprocate steel wool Bonstar (#0000) 10,000 times at a pressure of 98.07 kPa and a speed of 320 cm / min, and the water contact angle was then measured using the method described above. The smaller the decrease in water repellency (water contact angle) after abrasion, the smaller the decrease in performance due to friction, indicating superior abrasion resistance. The evaluation criteria are as follows: A (Excellent): The change in water contact angle after 15,000 reciprocating cycles is 2 degrees or less. B (Good): The change in water contact angle after 15,000 reciprocating cycles is more than 2 degrees and not more than 5 degrees. C (Fair): The change in water contact angle after 15,000 reciprocating cycles is more than 5 degrees and not more than 10 degrees. D (unacceptable): The change in the water contact angle after 15,000 reciprocating strokes exceeds 10 degrees.

[0171] <Rubbing Resistance (Steel Wool)> The surface layer was subjected to a light resistance test using a tabletop xenon arc lamp accelerated light resistance tester (SUNTEST XLS+, manufactured by Toyo Seiki Seisakusho Co., Ltd.) at a black panel temperature of 63°C and a light beam (650 W / m ２ , 300 to 700 nm) for 1000 hours, and then the water contact angle was measured by the above method. The smaller the decrease in water repellency (water contact angle) after light irradiation, the smaller the decrease in performance due to light and the more excellent the light resistance. The evaluation criteria are as follows: A (Excellent): The change in water contact angle after light irradiation is 2 degrees or less. B (Good): The change in water contact angle after light irradiation is more than 2 degrees and not more than 5 degrees. C (Fair): The change in water contact angle after light irradiation is more than 5 degrees and not more than 10 degrees. D (Fail): The change in water contact angle after light irradiation is more than 10 degrees.

[0172]

[0173] As shown in Table 1, it was clear that the surface layer formed using the present composition was excellent in abrasion resistance and light resistance.

[0174] Furthermore, various fluorine-containing ether compounds were synthesized. Synthesis examples are shown below. [Example 8] The following compound 8-0 was obtained according to the synthesis method described in Example 1 of Japanese Patent No. 6044211. CF ３ CF ２ -O-(CF２ O) ｍ７ -(CF ２ CF ２ O) ｎ１７ -CF ２ CF ２ -I Formula (8-0) where the average values ​​of repeating units m7 and n17 are 22 and 24, respectively.

[0175] Synthesis Example 8-1 4.1 g of compound 8-1 was obtained in the same manner as in Synthesis Example 2-1, except that compound 1-1 in Synthesis Example 2-1 was changed to 5 g of compound 8-0.

[0176] ...Formula (8-1)

[0177] NMR spectrum of compound 8-1; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.5-3.0 (2H), 2.6-1.3 (10H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): -52.0 to -58.2 (44F), -85.8 (2F), -89.2 (3F), -89.6 to -92.3 (98F), 110.9 to -115.8 (2F) Average value of m8: 22, average value of n18: 24.

[0178] Synthesis Example 8-2 1.4 g of compound 8-2 was obtained in the same manner as in Synthesis Example 2-2, except that compound 2-1 in Synthesis Example 2-2 was changed to compound 8-1.

[0179] ...Formula (8-2)

[0180] NMR spectrum of compound 8-2; １ H-NMR (400MHz, Chloroform-d) δ (ppm): 5.9-5.7 (3H), 5.1-4.9 (6H), 2.5-1.1 (20H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): -52.0 to -58.2 (44F), -85.8 (2F), -89.2 (3F), -89.6 to -92.3 (98F), 110.6 to -115.8 (2F) Average value of m9: 22, average value of n19: 24.

[0181] Synthesis Example 8-3 1.0 g of compound (VIII) was obtained in the same manner as in Synthesis Example 2-3, except that compound 2-2 in Synthesis Example 2-3 was changed to compound 8-2.

[0182] ... NMR spectrum of compound (8-3) of formula (VIII); １ H-NMR (400MHz, Chloroform-d) δ (ppm): 3.6 (27H), 2.6-0.8 (26H), 0.6 (6H) １９ H-NMR (376 MHz, Chloroform-d) δ (ppm): -52.0 to -58.2 (44F), -85.8 (2F), -89.2 (3F), -89.6 to -92.3 (98F), 110.4 to -115.7 (2F) Average value of m10: 22, average value of n20: 24.

[0183] Examples of articles having a surface layer containing the present compound include optical articles used as parts of the following products, touch panels, anti-reflection films, anti-reflection glass, 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.

[0184] This application claims priority based on Japanese Patent Application No. 2021-191387, filed on November 25, 2021, the disclosure of which is incorporated herein in its entirety.

[0185] 10: Base material with undercoat layer, 12: Base material, 14: Undercoat layer, 20: Article, 22: Surface layer

Claims

1. A compound represented by the following formula (1) or the following formula (2). A １ -(OR ｆ１ ) ｙ１ -R １ -Q １ -R ２ -L １ -(R ３ -T １ ) ｘ１ ・・・Formula (1) (T ３ - R ９ ) ｘ３ - L ３ - R ８ - Q ３ - R ７ - R ｆ - (OR ｆ２ ) ｙ２ - R ４ - Q ２ - R ５ - L ２ - (R ６ - T ２ ) ｘ２ ・・・ Formula (2) However, A １ is a fluoroalkyl group having 1 to 20 carbon atoms, R ｆ１ is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are a plurality of R ｆ１ s, the plurality of R ｆ１ s may be the same as or different from each other. R １ is a single bond or a divalent group, Q １ contains one or more ring structures, and the atoms constituting the ring structure are divalent groups that bond with R １ and R ２ and are divalent groups that bond with R R ２ is a single bond or a divalent group, L １ is a 1 + x-valent group which may have a single bond or contain N, O, S, Si and may have a branching point, where the ２ atoms bonded to R ３ and R are each independently an N, O, S, Si atom, a carbon atom forming a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O). R ３ is an alkylene group or an alkylene group having an etheric oxygen atom at the terminal on the L １ side or between carbon-carbon atoms, and when there are a plurality of R ３ the plurality of R ３ may be the same as or different from each other. T １ is -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ wherein R ａ１ is a hydroxyl group or a hydrolyzable group, and when there are a plurality of R ａ１ s, the plurality of Rs ａ１ may be the same as or different from each other R ａ１１ is a non-hydrolyzable group, and when there are a plurality of R ａ１１ , the plurality of R ａ１１ may be the same as or different from each other. z1 is an integer from 0 to 3, and when there are a plurality of z1, the plurality of z1 may be the same as or different from each other, provided that at least one of z1 is an integer from 1 to 3, x1 is an integer of 1 or more, y1 is an integer of 1 or more, R ｆ is a fluoroalkylene group having 1 to 6 carbon atoms, R ｆ２ is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are a plurality of R ｆ２ s, the plurality of Rs ｆ２ may be the same as or different from each other. R ４ is a single bond or a divalent group, Q ２ contains one or more ring structures, and the atoms constituting the ring structure are divalent groups that bond to R ４ and R ５ and is a divalent group that binds to R ５ is a single bond or a divalent group, L ２ is a 1 + x divalent group which may have a single bond or contain N, O, S, Si and may have a branching point, and the ５ atoms bonded to R ６ and R are each independently an N, O, S, Si atom, a carbon atom forming a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O). R ６ is an alkylene group or an alkylene group having an etheric oxygen atom at the terminal on the L ２ side or between carbon-carbon atoms, and when there are a plurality of R ６ the plurality of R ６ may be the same as or different from each other. T ２ is -SiR ａ２ ｚ２ R ａ１２ ３－ｚ２ and is R ａ２ is a hydroxyl group or a hydrolyzable group, and when there are a plurality of R ａ２ , the plurality of R ａ２ may be the same as or different from each other. R ａ１２ is a non-hydrolyzable group, and when there are a plurality of R ａ１２ , the plurality of R ａ１２ may be the same as or different from each other. z2 is an integer from 0 to 3, and when there are a plurality of z2, the plurality of z2 may be the same as or different from each other, provided that at least one of z2 is an integer from 1 to 3, R ７ is a single bond or a divalent group, Q ３ contains one or more ring structures, and the atoms constituting the ring structure are divalent groups that bond to R ７ and R ８ and is a divalent group that binds to R ８ is a single bond or a divalent group, L ３ is a 1 + x trivalent group which may have a single bond or contain N, O, S, Si and may have a branching point, where R ８ and R ９ are each independently an N, O, S, Si atom, a carbon atom forming a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O). R ９ is an alkylene group or an alkylene group having an etheric oxygen atom at the terminal on the L ３ side or between carbon-carbon atoms, and when there are a plurality of R ９ the plurality of R ９ may be the same as or different from each other. T ３ is —SiR ａ３ ｚ３ R ａ１３ ３－ｚ３ and is R ａ３ is a hydroxyl group or a hydrolyzable group, and when there are a plurality of R ａ３ s, the plurality of R ａ３ s may be the same as or different from each other. R ａ１３ is a non-hydrolyzable group, and when there are a plurality of R ａ１３ , the plurality of R ａ１３ may be the same as or different from each other. z3 is an integer from 0 to 3, and when there are a plurality of z3, the plurality of z3 may be the same as or different from each other, provided that at least one of z3 is an integer from 1 to 3, x2 and x3 are each independently an integer of 1 or more, y2 is an integer of 1 or more.

2. Q １ , Q ２ and Q ３ The compound according to claim 1, wherein at least one of

3. Q １ , Q ２ and Q ３ The compound according to claim 1 or 2, wherein at least one of

4. R １ , R ４ and R ７ The compound according to claim 1 or 2, wherein at least one of

5. The compound according to claim 3, wherein at least one of R1, R4 and R7 is an alkylene group.

6. R ２ , R ５ and R ８ The compound according to claim 1 or 2, wherein at least one of

7. The compound according to claim 3, wherein at least one of R2, R5 and R8 is a single bond or an alkylene group.

8. The compound according to claim 4, wherein at least one of R2, R5 and R8 is a single bond or an alkylene group.

9. The compound according to claim 5, wherein at least one of R2, R5 and R8 is a single bond or an alkylene group.

10. A composition containing the compound according to claim 1 or 2 and another fluorine-containing ether compound.

11. A surface treatment agent containing the compound according to claim 1 or 2, or a composition containing the compound according to claim 1 or 2 and another fluorine-containing ether compound.

12. A coating liquid containing the compound according to claim 1 or 2, or a composition containing the compound according to claim 1 or 2 and another fluorine-containing ether compound, and a liquid medium.

13. An article having a surface layer formed from the compound according to claim 1 or 2, a composition containing the compound according to claim 1 or 2 and another fluorine-containing ether compound, or a surface treatment agent containing the compound or the composition on the surface of a substrate.

14. A method for manufacturing an article, which comprises forming a surface layer by a dry coating method or a wet coating method using the compound according to claim 1 or 2, a composition containing the compound according to claim 1 or 2 and another fluorine-containing ether compound, a surface treatment agent containing the compound or the composition, or a coating liquid containing the compound or the composition and a liquid medium.

15. A compound represented by the following formula (3) or (4). A １ -(OR ｆ１ ) ｙ１ -R １ -Q １ -R ２１ -D １ ・・・Formula (3) D ３ -R ８１ -Q ３ -R ７ -R ｆ -(OR ｆ２ ) ｙ２ -R ４ -Q ２ -R ５１ -D ２ ... Formula (4) However, A １ is a fluoroalkyl group having 1 to 20 carbon atoms, R ｆ１ is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are a plurality of R ｆ１ , the plurality of R ｆ１ may be the same as or different from each other. R １ is a single bond or a divalent group, Q １ contains one or more ring structures, and the atoms constituting the ring structure are divalent groups that bind to R １ and R ２ and is a divalent group that binds to R ２１ is a single bond or a divalent group, D １ is a halogen atom, y1 is an integer of 1 or more, R ｆ is a fluoroalkylene group having 1 to 6 carbon atoms, R ｆ２ is a fluoroalkylene group having 1 to 6 carbon atoms, and when there are a plurality of R ｆ２ , the plurality of R ｆ２ may be the same as or different from each other. R ４ is a single bond or a divalent group, Q ２ contains one or more ring structures, and the atoms constituting the ring structure are divalent groups that bond to R ４ and R ５ and are divalent groups that bond to R R ５１ is a single bond or a divalent group, R ７ is a single bond or a divalent group, Q ３ contains one or more ring structures, and the atoms constituting the ring structure are divalent groups that bond to R ７ and R ８ and are divalent groups that bond to R ８１ is a single bond or a divalent group, D ２ and D ３ are each independently a halogen atom, y2 is an integer of 1 or more.