Compounds, compositions, surface treatment agents, articles, and methods for manufacturing articles

Abstract

Provided are a compound, a composition, a surface treatment agent capable of forming a surface layer excellent in abrasion resistance, fingerprint stain removal property, and slip resistance, an article having a surface layer formed from the compound or the like, and a method for producing the article. Also provided is a novel compound that can be used in the production of the above compound. 【Solution means】The compound of the present invention is represented by formula (1). R f1 -R f2 -(OR f3 ) y1 -R 1 -L 1 -(R 2 -T 1 ) x1 ···(1) R f1 is an organic group containing a ring structure or a chain hydrocarbon group having 3 or more carbon atoms and having no fluorine atom, R f2 is a fluoroalkylene group having 1 to 6 carbon atoms or the like, R f3 is a fluoroalkylene group having 1 to 6 carbon atoms, R 1 is an alkylene group having 1 to 20 carbon atoms or the like, L 1 is a (1 + x1)-valent group or the like, R 2 is an alkylene group or the like, T 1 is a reactive group, y1 is an integer of 2 or more, and x1 is an integer of 1 to

Description

[Technical Field]

[0001] The present invention relates to compounds, compositions, surface treatment agents, articles, and methods for manufacturing articles. [Background technology]

[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. For example, fluorine-containing ether compounds having a perfluoropolyether chain and a hydrolyzable silyl group can form a surface layer on the substrate surface that exhibits high lubricity, water repellency, and oil repellency, making them suitable for use as surface treatment agents. Surface treatment agents containing fluorine-containing ether compounds are used in applications where it is required that the surface layer maintains its water repellency and oil repellency even after repeated friction with fingers (friction resistance) and that fingerprints adhering to the surface layer can be easily removed by wiping (fingerprint stain removal) for a long period of time, such as components that make up the surface touched by fingers on touch panels, eyeglass lenses, and displays of wearable devices. Furthermore, depending on the application of the component, it may be required to have properties other than those mentioned above, such as slip resistance. For example, Patent Document 1 discloses forming a surface layer using a specific fluorine-containing ether compound to make the surface of an electronic device less slippery. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] International Publication No. 2019 / 151445 [Overview of the project] [Problems that the invention aims to solve]

[0004] In recent years, mobile devices such as smartphones and tablet terminals may use a housing coated with glass, and the above surface treatment agent may be used on the housing side. In addition, the use of wireless chargers as mobile phone chargers is increasing. The surface layer formed by the current surface treatment agent may be slippery, and there is a risk of slipping when operating a mobile device or when it is placed on a desk or a wireless charger. Thus, the required performance for the surface layer formed using the fluorine-containing ether compound has increased, and it is required to be excellent not only in abrasion resistance and fingerprint stain removal properties but also in anti-slip properties. When the inventors evaluated the surface layer formed using the surface treatment agent containing the fluorine-containing ether compound by referring to the surface treatment agent described in Patent Document 1, it was found that at least in terms of anti-slip properties, it did not reach the level required in recent years and there was room for improvement.

[0005] In view of the above problems, an object of the present invention is to provide a compound, a composition, a surface treatment agent capable of forming a surface layer excellent in abrasion resistance, fingerprint stain removal properties, and anti-slip properties, an article having a surface layer formed from the compound and the like, and a method for producing the article. Another object is to provide a novel compound that can be used in the production of the above compound. [Means for Solving the Problems]

[0006] As a result of intensive studies on the above problems, the inventors have found that the above problems can be solved by the following configuration. [1] A compound represented by the following formula (1). R f1 -R f2 -(OR f3 ) y1 -R 1 -L 1 -(R 2 -T 1 ) x1 ···(1) However, R f1This is an organic group that contains a cyclic structure or a chain-like hydrocarbon group having 3 or more carbon atoms and does not have a fluorine atom. R f2 This is a single bond or a fluoroalkylene group having 1 to 6 carbon atoms. R f3 This is a fluoroalkylene group having 1 to 6 carbon atoms. R 1 This is a single bond, a fluoroalkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 20 carbon atoms, or an alkylene group having 1 to 20 carbon atoms with an etheric oxygen atom. L 1 It is a single bond or a 1+x1 valent group. R 2 This is an alkylene group, or an alkylene group having an etheric oxygen atom. T 1 It is a reactive group, y1 is an integer greater than or equal to 2. x1 is an integer between 1 and 10. R f3 , R 2 , or T 1 When there are multiple R f3 , R 2 , or T 1 They may be the same or different from one another. [2] The above T 1 However, -Ar, -SR 10 , -NOR 10 -C(=O)R 10 , -N(R 10 )2, -N + (R 10 )3X 3 -C≡N, -C(=NR) 10 )-R 10 , -N + ≡N, -N=NR 10 , -C(=O)OR 10 -C(=O)OX 2 -C(=O)X 4 -C(=O)OC(=O)R 10 , -SO2R 10 -SO3H, -SO3X 2 -OP(=O)(-OR10 )2, -OP(=O)(-OR 10 )(-OX 2 ), -N=C=O, -SiR a1 z1 R a11 3-z1 , -C(R 10 )=C(R 10 )2, -C≡C(R 10 ), -C(=O)N(R 10 )2, -N(R 10 )C(=O)R 10 , -Si(R 10 )2-O-Si(R 10 )3, -NH-C(=O)R 10 -C(=O)NHR 10 ,-I, [ka] The compound described in [1], which is one of the following: however, R 10 This is a hydrogen atom, an optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 fluoroalkyl group, or an optionally substituted aryl group. Ar is an aryl group which may have substituents. X 2 These are alkali metal ions or ammonium ions, X 3 It is a halide ion, X 4 It is a halogen atom, R a1 This is a hydrolyzable group or a hydroxyl group, R a11 It is a hydrocarbon group, z1 is an integer between 1 and 3. R 10 , R a1 , or R a11 When there are multiple R 10 , R a1 , or R a11 They may be the same or different from one another. [3] The above T 1 However, -SiR a1 z1 R a11 3-z1 The compound described in [2]. [4] The above R f1 The compound according to any one of [1] to [3], wherein the ring structure in comprises at least one selected from the group consisting of an aliphatic hydrocarbon ring and an aromatic ring. [5] The above R f1 However, the compound is one of the compounds listed in [1] to [4], which has a group represented by the following formula (2). XLY- ···(2) however, X is an aliphatic hydrocarbon ring group which may have substituents, an aromatic ring group which may have substituents, or a chain hydrocarbon group having 3 or more carbon atoms. L is a single bond, an alkylene group which may have substituents, *-P(R L1 )-R L2 -**, or -Si(R L3 )2- and R L1 R is an alkyl group or a phenyl group, L2 It is an alkylene group, and has two R L3 Each is independently an alkyl group or a phenyl group, * is the bond position with X in formula (2), ** is the bond position with Y in formula (2), and if L is an optionally substituted alkylene group, X is an optionally substituted aliphatic hydrocarbon ring group or an optionally substituted aromatic ring group. Y is -O-, -NR 11 C(=O)- or -OC(=O)-, and R 11 This is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or -LX. R 11 If the expression is -LX, the multiple L or X values ​​may be the same or different from one another. [6] The compound described in [5], wherein Y is -O-. [7] The above Rf1 The compound according to any one of [1] to [6], wherein the organic group in f1 contains a ring structure. [8] A composition comprising the compound according to [1] and another fluorine-containing compound. [9] A surface treatment agent comprising the compound according to any one of [1] to [7] or the composition according to [8].

[10] The surface treatment agent according to [9], which is an antifouling coating agent or a waterproof coating agent.

[11] The surface treatment agent according to [9] or

[10] , further comprising a liquid medium.

[12] An article having a surface layer formed on the surface of a substrate using the compound according to any one of [1] to [7] or the composition according to any one of [8] to

[11] .

[13] The article according to

[12] , having the above surface layer on the surface of a member constituting a surface touched by a finger of a touch panel.

[14] The article according to

[12] or

[13] , which is an optical member.

[15] A method for manufacturing an article, wherein a surface layer is formed by a dry coating method using the surface treatment agent according to any one of [9] to

[11] .

[16] A method for manufacturing an article, wherein a surface layer is formed by a wet coating method using the surface treatment agent according to any one of [9] to

[11] .

[17] A compound represented by the following formula (M1). CF2=CF-(OR f ) y -C(=O)N(R m1 )-L m2 -C(R m2 -CH2=CH2)3···(M1) However, R f is a fluoroalkylene group having 1 to 6 carbon atoms, R m1is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, L m2 is a single bond or a divalent organic group, R m2 is a single bond, an alkylene group, or an alkylene group having an etheric oxygen atom, y is an integer of 2 or more, a plurality of R f , or R m2 may be the same as or different from each other.

Advantages of the Invention

[0007] According to the present invention, it is possible to provide a compound, a composition, a surface treatment agent capable of forming a surface layer excellent in antifriction property, fingerprint stain removal property, and anti-slip property, an article having a surface layer formed from the compound or the like, and a method for producing the article. Further, it is also possible to provide a novel compound usable for the production of the above compound.

Brief Description of the Drawings

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

Modes for Carrying Out the Invention

[0009] The meanings of the terms in the present invention are as follows. In the present specification, the compound represented by formula (1) is referred to as compound 1. Compounds and the like represented by other formulas are also in accordance with this. The fluoroalkyl group is a general term for a perfluoroalkyl group and a partial fluoroalkyl group. The perfluoroalkyl group means a group in which all hydrogen atoms of an alkyl group are substituted with fluorine atoms. The partial fluoroalkyl group is an alkyl group in which one or more hydrogen atoms are substituted with fluorine atoms and which has one or more hydrogen atoms. That is, the fluoroalkyl group is an alkyl group having one or more fluorine atoms. The fluoroalkylene group is also in accordance with this. "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 undergo hydrolysis to form a silanol group. An "organic group" refers to a hydrocarbon group that may have substituents and may have heteroatoms or other bonds in its carbon chain. A "hydrocarbon group" is a group consisting of aliphatic hydrocarbon groups (such as linear alkylene groups, branched alkylene groups, and cycloalkylene groups), aromatic hydrocarbon groups (such as phenylene groups), and combinations thereof. The term "surface layer" refers to the layer formed on the surface of the substrate. The "molecular weight" of a polyfluoroether chain is, 1 H-NMR and 19 This is the number-average molecular weight calculated by determining the number (average value) of oxyfluoroalkylene units based on the terminal groups using F-NMR. The "~" symbol indicating a numerical range means that the numbers before and after it are included as the lower and upper limits, respectively. The bonding order in each divalent group is not limited unless otherwise specified. For example, L, which will be discussed later. 1 -C(O)N(R 26 If the group is represented by )-, the left-hand bond is R of formula (1) 1 The bond may be on the side, or the bond on the right side may be R in equation (1) 1 It may be attached to the side.

[0010] [Compound 1] The compound of the present invention is represented by the following formula (1). In this specification, the compound represented by formula (1) is also referred to as "compound 1".

[0011] R f1 -R f2 -(OR f3 ) y1 -R 1 -L 1 -(R 2 -T 1 ) x1 ...(1)

[0012] In formula (1), Rf1 This is an organic group that contains a ring structure or a chain-like hydrocarbon group having 3 or more carbon atoms and does not have a fluorine atom. R f2 This is a single bond or a fluoroalkylene group having 1 to 6 carbon atoms. R f3 This is a fluoroalkylene group having 1 to 6 carbon atoms. R 1 This is a single bond, a fluoroalkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 20 carbon atoms, or an alkylene group having 1 to 20 carbon atoms with an etheric oxygen atom. L 1 It is a single bond or a 1+x1 valent group. R 2 This is an alkylene group, or an alkylene group having an etheric oxygen atom. T 1 It is a reactive group, y1 is an integer greater than or equal to 2. x1 is an integer between 1 and 10. R f3 , R 2 , or T 1 When there are multiple R f3 , R 2 , or T 1 They may be the same or different from one another.

[0013] Compound 1 has, in general terms, a structure consisting of a "fluoropolyether chain" - "linking group" - "reactive group placed on the substrate surface," with an organic group (hereinafter also referred to as a "specific organic group") containing a cyclic structure or a chain-like hydrocarbon group with 3 or more carbon atoms and no fluorine atoms, positioned at the end of the fluoropolyether chain. When forming a surface layer using compound 1, the reactive groups of compound 1 are easily positioned on the substrate side, and these reactive groups form strong chemical bonds with the substrate, resulting in a surface layer with excellent abrasion resistance. Furthermore, specific organic groups are easily positioned on the side of the surface layer opposite to the substrate, and these specific organic groups, compared to fluoroalkyl groups, exhibit superior abrasion resistance in the resulting surface layer due to intermolecular interactions. On the surface opposite to the base material in the surface layer, a fluoropolyether chain having a specific organic group at the terminal is arranged. Therefore, the resulting surface layer is excellent in fingerprint stain removability and also in water and oil repellency. Furthermore, since in Compound 1 a specific organic group is arranged at the terminal of the fluoropolyether chain, it is presumed that the movement of the fluoropolyether chain on the surface is restricted as compared with a fluorinated ether compound having a fluoroalkyl group at the terminal. As a result, the surface layer formed by Compound 1 has a high coefficient of friction. From these facts, an article having a surface layer obtained by using Compound 1 is excellent in fingerprint stain removability and abrasion resistance, and also in slip resistance.

[0014] Hereinafter, the structures of the respective compounds will be described. For symbols having the same structure, it is shown as such, and it is assumed that they can be read appropriately and referred to.

[0015] R f1 is an organic group that includes a ring structure or a chain hydrocarbon group having 3 or more carbon atoms and does not have a fluorine atom.

[0016] R f1 Examples of the ring structure in R include an aliphatic hydrocarbon ring, an aromatic ring, and a heterocyclic ring. From the viewpoint that the effects of the present invention are more excellent, it preferably contains at least one selected from the group consisting of an aliphatic hydrocarbon ring and an aromatic ring. Specific examples of the aliphatic hydrocarbon ring include monocyclic aliphatic hydrocarbons such as cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, polycyclic aliphatic hydrocarbons such as 4-cyclohexylcyclohexane, decahydronaphthalene, aliphatic hydrocarbons having a bridged ring structure such as bicyclopentane, norbornane, norbornene, adamantane, and aliphatic hydrocarbons having a spiro ring structure such as spiro[3.4]octane. Specific examples of the aromatic ring include aromatic hydrocarbon rings such as benzene, naphthalene, anthracene, and aromatic heterocyclic rings such as furan, pyrrole, thiophene, pyridine, triazine, triazole, pyrazole, thiazole, benzothiazole. Specific examples of heterocycles include pyrrolidine, piperidine, tetrahydrofuran, tetrahydropyran, dioxane, quinuclidine, and crown ethers. Aliphatic hydrocarbon rings, aromatic rings, and heterocycles may have substituents, and specific examples of substituents are described below.

[0017] R f1 The linear hydrocarbon group in this product may be saturated or unsaturated, but it is preferable that it be saturated (i.e., a linear alkyl group) in order to achieve superior effects of the present invention. R f1 The number of carbon atoms in the chain-like hydrocarbon group is 3 or more, preferably 8 or more, and more preferably 16 or more, from the viewpoint of superior friction resistance and slip resistance. R f1 The number of carbon atoms in the chain hydrocarbon group is preferably 30 or less, more preferably 25 or less, and even more preferably 20 or less, from the viewpoint of superior antifouling performance.

[0018] R f1 The organic group in this material preferably contains a ring structure because it offers superior slip resistance.

[0019] R f1 From the viewpoint of achieving superior effects in the present invention, it is preferable that the group is represented by the following formula (2). XLY- ···(2)

[0020] In formula (2), X is an aliphatic hydrocarbon ring group which may have substituents, an aromatic ring group which may have substituents, or a chain hydrocarbon group having 3 or more carbon atoms. L is a single bond, an alkylene group which may have substituents, *-P(R L1 )-R L2 -**, or -Si(R L3 )2- and R L1 R is an alkyl group or a phenyl group, L2 It is an alkylene group, and has two R L3Each is independently an alkyl group or a phenyl group, * is the bond position with X in formula (2), ** is the bond position with Y in formula (2), and if L is an optionally substituted alkylene group, X is an optionally substituted aliphatic hydrocarbon ring group or an optionally substituted aromatic ring group. Y is -O-, -NR 11 C(=O)- or -OC(=O)-, and R 11 This is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or -LX. R 11 If the expression is -LX, the multiple L or X values ​​may be the same or different from one another. Note that X, L, and Y do not contain any fluorine atoms.

[0021] R 11 The number of carbon atoms in the alkyl group is 1 to 6, preferably 1 to 4. When the number of carbon atoms in the alkyl group is 3 or more, the alkyl group may be linear, branched, or have a ring structure.

[0022] Specific examples of aliphatic hydrocarbon ring groups and aromatic ring groups in X are, respectively, R f1 The aliphatic hydrocarbon ring and aromatic ring described in [previous section] are the same, and the preferred embodiments are also the same. A specific example of a chain hydrocarbon group with 3 or more carbon atoms in X is R f1 This is similar to the chain-like hydrocarbon group having 3 or more carbon atoms described above, and the preferred embodiment is also the same.

[0023] Specific examples of substituents that the aliphatic hydrocarbon ring group and aromatic ring group in X may have include alkyl groups (preferably with 1 to 20 carbon atoms), alkoxy groups (preferably with 1 to 3 carbon atoms), and -N(R X1 )2. Examples include a phenyl group, a phenoxy group, and a pyridyl group, and these groups may have further substituents. 2 R X1 Each of these is independently a hydrogen atom, an alkyl group, or a phenyl group.

[0024] The number of carbon atoms in the alkylene group L, which may have substituents, is preferably 1 to 30, more preferably 3 to 25, and even more preferably 6 to 20, from the viewpoint of friction resistance, slip resistance, and antifouling performance. Note that carbon atoms included in substituents are not included in the number of carbon atoms of the alkylene group. If the alkylene group in L, which may have substituents, has 3 or more carbon atoms, the alkylene group may be linear, branched, or have a cyclic structure, but a linear alkylene group or a branched alkylene group is preferred. A specific example of a substituent that the alkylene group in L may have is the phenyl group.

[0025] *-P(R) in L L1 )-R L2 -**, R L1 This is an alkyl group or a phenyl group. R L1 The alkyl group in R may be linear, branched, or have a ring structure. L1 The number of carbon atoms in the alkyl group is preferably 1 to 3. R L2 The alkylene group in R may be linear, branched, or have a ring structure. L2 The number of carbon atoms in the alkylene group is preferably 1 to 6.

[0026] -Si(R) at L L3 )2-, 2 R L3 Each of these is independently an alkyl group or a phenyl group. R L3 The alkyl group in R may be linear, branched, or have a ring structure. L3 The number of carbon atoms in the alkyl group is preferably 1 to 6.

[0027] L is preferably a single bond or an alkylene group which may have substituents, from the viewpoint of achieving superior effects of the present invention.

[0028] Y is -O- or -NR in terms of superior effects of the present invention. 11C(=O)- is preferred, and -O- is even more preferred due to its particularly excellent abrasion resistance.

[0029] R f2 It may be a single bond. f2 If it is a single bond, R f1 is (OR f3 ) y1 It bonds with the terminal oxygen atom. R f2 This may be a fluoroalkylene group having 1 to 6 carbon atoms. If the fluoroalkylene group has 3 to 6 carbon atoms, the 3 to 6 carbon atom fluoroalkylene group may be linear, branched, or have a cyclic structure. R f2 The number of carbon atoms is preferably 1 to 3, from the viewpoint of ease of synthesis, etc. R f2 Specific examples of fluoroalkyl groups in this context include -CF2-, -CHF-, -CF2CF2-, -CF2CHF-, -CF2CF2CF2-, -CF2CHFCF2-, -CF2CHFCHF-, -CF2CF(CF3)-, -CF2CF2CF2CF2-, -CF2CHFCF2CF2, -CF2CF(CF3)-CF2-, -CF2C(CF3)2-CF2-, -CF2CF2CF2CF2CF2-, and -CF2CF2CF2CF2CF2CF2-.

[0030] (OR f3 ) y1 is a fluoropolyether chain, and y1 is an integer greater than or equal to 2. (OR f3 ) y1 The fluoropolyether chain in this product preferably has a structure represented by the following formula (G1).

[0031] [(OG f1 ) m1 (OG f2 ) m2 (OG f3 ) m3 (OG f4 ) m4 (OG f5 ) m5 (OG f6 )m6 ] ···(G1)

[0032] In formula (G1), G f1 This is a fluoroalkylene group having 1 carbon atom, G f2 This is a fluoroalkylene group with 2 carbon atoms, G f3 This is a fluoroalkylene group with 3 carbon atoms, G f4 This is a fluoroalkylene group with 4 carbon atoms, G f5 This is a fluoroalkylene group with 5 carbon atoms, G f6 This is a fluoroalkylene group with 6 carbon atoms, m1, m2, m3, m4, m5, and m6 each independently represent an integer of 0 or greater than or equal to 1. m1+m2+m3+m4+m5+m6 (y1 in equation (1)) is an integer between 2 and 200. Note that in equation (G1) (OG f1 )~(OG f6 The order of joining the terms is arbitrary. In equation (G1), m1 to m6 are, respectively, (OG f1 )~(OG f6 This represents the number of ) and not the arrangement. For example, (OG f5 ) m5 (OG f5 This indicates that the number of ) is m5, and (OG f5 ) m5 This does not represent the block arrangement structure. Similarly, (OG f1 )~(OG f6 The order in which the terms are listed does not indicate the order in which the units are combined. Furthermore, the fluoroalkylene group having 3 to 6 carbon atoms may be linear, branched, or have a cyclic structure.

[0033] G f1 Specific examples include -CF2- and -CHF-. G f2Specific examples include -CF2CF2-, -CHFCF2-, -CHFCHF-, -CH2CF2-, and -CH2CHF-. G f3 Specific examples include -CF2CF2CF2-, -CF2CHFCF2-, -CF2CH2CF2-, -CHFCF2CF2-, -CHFCHFCF2-, -CHFCHFCHF-, -CHFCH2CF2-, -CH2CF2CF2-, -CH2CHFCF2-, -CH2CH2CF2-, -CH2CF2CHF-, -CH2CHFCHF-, -CH2CH2CHF-, -CF(CF3)-CF2-, -CF(CHF2)-CF2-, -CF(CH2F)-CF2-, -CF(CH3)-CF2-, -CF(CF3)-CHF-, -CF(CHF2)-CHF-, -CF(CH2F)-CHF-, -CF(CH3)-CHF-, -CF(CF3)-CH2-, -CF(CHF2)-CH2-, -CF(CH2F)-CH2-, -CF(CH3)-CH2-, -CH(CF3)-CF2-, -CH(CHF2)-CF2-, -CH(CH2F)- Examples include CF2-, -CH(CH3)-CF2-, -CH(CF3)-CHF-, -CH(CHF2)-CHF-, -CH(CH2F)-CHF-, -CH(CH3)-CHF-, -CH(CF3)-CH2-, -CH(CHF2)-CH2-, -CH(CH2F)-CH2-. G f4 Specific examples include -CF2CF2CF2CF2-, -CHFCF2CF2CF2-, -CH2CF2CF2CF2-, -CF2CHFCF2CF2-, -CHFCHFCF2CF2-, -CH2CHFCF2CF2-, -CF2CH2CF2CF2-, -CHFCH2CF2CF2-, -CH2CH2CF2CF2-, -CHFCF2CHFCF2-, -CH2CF2CHFCF2-, -CF2 Examples include CHFCHFCF2-, -CHFCHFCHFCF2-, -CH2CHFCHFCF2-, -CF2CH2CHFCF2-, -CHFCH2CHFCF2-, -CH2CH2CHFCF2-, -CF2CH2CH2CF2-, -CHFCH2CH2CF2-, -CH2CH2CH2CF2-, -CHFCH2CH2CHF-, -CH2CH2CH2CHF-, and -cycloC4F6-. G f5Specific examples include -CF2CF2CF2CF2CF2-, -CHFCF2CF2CF2CF2-, -CH2CHFCF2CF2CF2-, -CF2CHFCF2CF2CF2-, -CHFCHFCF2CF2CF2-, -CF2CH2CF2CF2CF2-, -CHFCH2CF2CF2CF2-, -CH2CH2CF2CF2CF2-, -CF2CF2CHFCF2CF2-, -CHFCF2CHFCF2CF2-, -CH2CF2CHFCF2CF2-, -CH2CF2CF2CF2CH2-, and -cycloC5F8-. G f6 Specific examples include -CF2CF2CF2CF2CF2CF2-, -CF2CF2CHFCHFCF2CF2-, -CHFCF2CF2CF2CF2CF2-, -CHFCHFCHFCHFCHFCHF-, -CHFCF2CF2CF2CF2CH2-, -CH2CF2CF2CF2CF2CH2-, -cycloC6F 10 - are listed. Here, -cycloC4F6- represents a perfluorocyclobutanediyl group, a specific example being the perfluorocyclobutane-1,2-diyl group. -cycloC5F8- represents a perfluorocyclopentanediyl group, a specific example being the perfluorocyclopentane-1,3-diyl group. -cycloC6F 10 - represents a perfluorocyclohexanediyl group, a specific example of which is the perfluorocyclohexane-1,4-diyl group.

[0034] (OR f2 ) y1 In terms of superior water-repellent and oil-repellent properties, abrasion resistance, and fingerprint stain removal, it is preferable to have a structure represented by the following formulas (G2) to (G4).

[0035] (OG f1 ) m1 -(OG f2 ) m2 ...Formula (G2) (OG f2 ) m2 -(OG f4 ) m4...Formula (G3) (OG f3 ) m3 ...Formula (G4)

[0036] The signs in equations (G2) to (G4) are the same as those in equation (G1) above.

[0037] In equations (G2) and (G3), (OG f1 ) and (OG f2 ), (OG f2 ) and (OG f4 The order in which the elements are joined is arbitrary. For example, (OG f1 ) and (OG f2 ) may be arranged alternately, (OG f1 ) and (OG f2 The elements may be placed in each block, or they may be placed randomly. The same applies to equation (G3). In formula (G2), m1 + m2 is 2 or greater. m1 is preferably 1 to 50, and more preferably 1 to 30. m2 is preferably 1 to 50, and more preferably 1 to 30. In formula (G3), m2 + m4 is 2 or greater. m2 is preferably 1 to 50, and more preferably 1 to 30. m4 is preferably 1 to 50, and more preferably 1 to 30. In formula (G4), m3 is 2 or more, preferably 2 to 50, and more preferably 2 to 30.

[0038] Fluoropolyether chain (OR f3 ) y1 It may have hydrogen atoms. On the other hand, in terms of superior abrasion resistance and fingerprint stain removal of the surface layer, (OR f3 ) y1 The proportion of fluorine atoms in the material is preferably 60% or more, more preferably 80% or more, and even more preferably substantially 100%, i.e., a perfluoropolyether chain. If the proportion of fluorine atoms is 60% or more, the amount of fluorine in the fluoropolyether chain increases, further improving the slipperiness and fingerprint removal properties. The proportion of fluorine atoms here is calculated using the following formula (I). Formula (I): Percentage of fluorine atoms (%) = (Number of fluorine atoms) / {(Number of fluorine atoms) + (Number of hydrogen atoms)} × 100

[0039] R 1 This is a single bond, a fluoroalkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 20 carbon atoms, or an alkylene group having 1 to 20 carbon atoms with an etheric oxygen atom. 1 If it is a single bond, (OR f3 ) y1 R located at the end f3 However, L 1 It connects directly with it.

[0040] R 1 When the group is a fluoroalkylene group having 3 to 20 carbon atoms, the fluoroalkylene group may be linear, branched, or have a cyclic structure. R 1 If the alkylene group has 3 to 20 carbon atoms, the alkylene group may be linear, branched, or have a ring structure. R 1 If the alkylene group has 3 to 20 carbon atoms and contains an etheric oxygen atom, the alkylene group may be linear, branched, or cyclic. The etheric oxygen atom may be located at the end of the alkylene group or between carbon atoms. R 1 If R is a fluoroalkylene group, an alkylene group, or an alkylene group having an etheric oxygen atom, 1 The number of carbon atoms is 1 to 20, preferably 1 to 6, and more preferably 1 to 3.

[0041] L 1 This is a single bond or a 1+x1 valent group. The 1+x1 valent group may have heteroatoms such as N, O, S, Si, etc., and may have branching points. 1 R inside 1 and R 2 The atoms bonded are preferably N, O, S, Si, a carbon atom constituting a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O), each independently. L1 If it is a single bond, then R in equation (1) 1 and R 2 They bond directly. Also, L 1 It is a single bond, and R 1 If it is a single bond, compound 1 is (OR f3 ) y1 and R 2 They are directly joined.

[0042] L 1 If the group is trivalent or higher, L 1 This is at least one branching point selected from the group consisting of C, N, Si, ring structures, and (1+x1) valent organopolysiloxane residues (hereinafter referred to as "branching point P"). 1 It is written as follows: ) has.

[0043] N is the branching point P. 1 In the case where this is the case, branch point P 1 This can be expressed as, for example, *-N(-**)², where * is R 1 It is a side coupling, and ** is R 2 It is a side joint. C is the branching point P 1 In the case where this is the case, branch point P 1 For example, *-C(-**)3 or *-CR 29 It is represented as (-**)2, where * and ** are the branching point P when N is the branching point. 1 This is similar to the case where R 29 A monovalent group is a group such as a hydrogen atom, a hydroxyl group, an alkyl group, or an alkoxy group. Si at branch point P 1 In the case where this is the case, branch point P 1 For example, *-Si(-**)3 or *-SiR 29 It is represented as (-**)2, where * and ** are the branching point P when N is the branching point. 1 This is similar to the case where R 29 C is the branching point P. 1 This is similar to the case where this occurs.

[0044] Branch point P 1As for the ring structure constituting the ring, from the standpoint of ease of synthesis and superior abrasion resistance, light resistance, and chemical resistance of the surface layer, one selected from the group consisting of a 3- to 8-membered aliphatic ring, a 3- to 8-membered aromatic ring, a 3- to 8-membered heteroring, and a fused ring consisting of two or more of these rings is preferred, and the ring structure shown in the following formula is more preferred. The ring structure may have substituents such as halogen atoms, alkyl groups (which may contain etheric oxygen atoms between carbon atoms), cycloalkyl groups, alkenyl groups, allyl groups, alkoxy groups, and oxo groups (=O).

[0045] [ka]

[0046] Branch point P 1 Examples of organopolysiloxane residues that make up the compound include the following groups. However, R in the following formula 25 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 25 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and more preferably 1.

[0047] [ka]

[0048] L with 2 or more valent values 1 is -C(O)N(R 26 )-, -C(O)O-, -C(O)-, -C(OH)-, -O-, -N(R 26 )-, -S-, -OC(O)O-, -NHC(O)O-, -NHC(O)N(R 26 )-,-SO2N(R 26 )-,-N(R 26 )SO2-,-Si(R 26 )2-, -OSi(R 26 )2-, -Si(CH3)2-Ph-Si(CH3)2- and divalent organopolysiloxane residues, at least one type of bond selected from this group (hereinafter referred to as "bond B").1 It may have the following: However, R 26 R 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 to 2, from the standpoint of facilitating the production of compound 1.

[0049] Examples of divalent organopolysiloxane residues include the group shown in the following formula. However, R in the following equation 27 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 27 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and more preferably 1.

[0050] [ka]

[0051] Join B 1 From the standpoint of ease of synthesis, -C(O)NR 26 -, -N(R 26 )C(O)-, -C(O)-, and -NR 26 -C(O)NR is preferred because it provides even better light resistance and chemical resistance to the surface layer. 26 -, -N(R 26 )C(O)- or -C(O)- is more preferred.

[0052] divalent L 1 For example, R 1 and R 2 It is preferable that the atoms bonded to each are independently N, O, S, Si atoms, or carbon atoms having a hydroxyl group or an oxo group (=O). That is, R 1 and R 2 Each adjacent atom is bonded to B 1 It is preferable that it be a constituent element of . L with a valency of 2 or higher 1 A specific example is one or more bonds B 1(For example, *-B 1 -**, *-B 1 -R 28 -B 1 -**) is one example. However, R 28 * is a single bond or a divalent organic group, and * is R 1 It is a side coupling, and ** is R 2 It is a side joint.

[0053] L with a valent or higher chromosome 1 R 1 and R 2 It is preferable that the atoms bonded to each are, independently, N, O, S, Si, a carbon atom constituting a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O). That is, R 1 and R 2 Each adjacent atom is bonded to B 1 Or branch point P 1 It is preferable that it be a constituent element of . L with a valency of 3 or higher. 1 A concrete example of this is one or more branching points P. 1 (For example {*-P 1 (-**) x1}), one or more branching points P 1 and one or more bonds B 1 A combination with {*-B 1 -R 28 -P 1 (-**) x1}, {*-B 1 -R 28 -P 1 (-R 28 -B 1 -**) x1}) is one example. However, R 28 * is a single bond or a divalent organic group, and * is R 1 It is a side coupling, and ** is R 2 It is a side joint.

[0054] The above R 28 Examples of divalent organic groups in this context include divalent aliphatic hydrocarbon groups (alkylene groups, cycloalkylene groups, etc.) and divalent aromatic hydrocarbon groups (phenylene groups, etc.), where a bond exists between carbon atoms in hydrocarbon groups with two or more carbon atoms.1 It may have a divalent organic group. The number of carbon atoms in the divalent organic group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.

[0055] The above L 1 As such, a group represented by any of the following formulas (E1) to (E7) is preferred because it facilitates the production of compound 1.

[0056] [ka] -E 1 -C(R E2 ) 3-e3 (-E 22 -) e3 ...Equation (E2) -E 2 -N(-E 23 -)2...Equation (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 equations (E1) to (E7), E 1 , E 2 or E 3 The side is R in equation (1) 1 Connect to E 22 , E 23 , E 24 , E 25 or E 26 The side is R 2 Connect to it. Here, E1 is a single bond, -B 5 -, -B 6 -R 40 -, or -B 6 -R 40 -B 5 -and R 40 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms, with -C(O)NR between carbon atoms. E6 -, -C(O)-, -NR E6 A group having - or -O-, B 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 that joins 1 If the atom in is a carbon atom, then E 1 E 3 Z that joins 1 If the atom in is a nitrogen atom, then E 2 And, E 11 This refers to a single bond, -O-, an alkylene group, or an alkylene group with 2 or more carbon atoms with -C(O)NR between carbon atoms. E6 -, -C(O)-, -NR E6 A group having - or -O- E 22 is a single bond, -B 5 -, -R 40 -B 6 -or-B 5 -R 40 -B 6 - and E 22 If you have 2 or more E 22 They may be the same or different. E 23 is a single bond or -R 40 -B 6 - and 2 E23 They may be the same or different. E 24 is, E 24 Z that joins 1 If the atom in is a carbon atom, then E 22 E 24 Z that joins 1 If the atom in is a nitrogen atom, then E 23 E 24 If you have 2 or more E 24 They may be the same or different. E 25 This is a single bond, or -R 40 -B 6 - and E 25 If you have 2 or more E 25 They may be the same or different. E 26 is a single bond or -R 40 -B 6 -and, Z 1 is, E 3 It has a carbon or nitrogen atom that is directly bonded to it and E 24 It is a group having a (e4+1) valence ring structure with a carbon or nitrogen atom to which it is directly bonded, R E1 is a hydrogen atom or an alkyl group, and R E1 If you have 2 or more of these, then 2 or more R E1 They 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, R E6 These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. e1 is an integer between 0 and 2, e2 is an integer between 0 and 3, and e1 + e2 is an integer between 1 and 5. e3 is an integer between 1 and 3. e4 is an integer greater than or equal to 1. e5 is an integer between 1 and 3. Furthermore, e1+e2=x1, e3=x1, e4=x1, and e5+1=x1.

[0057] 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 standpoint of facilitating the production of compound 1 and further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. However, the lower limit of the number of carbon atoms in the alkylene group when there is a specific bond between carbon atoms is 2.

[0058] Z 1 The ring structure in is the ring structure described above, and the preferred form is also the same. 1 The ring structure in E 24 Because they bond directly, for example, an alkylene group is linked to the ring structure, and E is attached to that alkylene group. 24 They will not be connected.

[0059] R E1 , R E2 or R E3 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the standpoint of facilitating the production of compound 1. R E2 The number of carbon atoms in the alkyl group portion of the acyloxy group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the standpoint of facilitating the production of compound 1. e4 is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3, due to the ease of producing compound 1 and the superior abrasion resistance and fingerprint stain removal properties of the surface layer.

[0060] L 1 Other forms of this include groups represented by any of the following formulas (E11) to (E17).

[0061] [ka] -E 1 -C(R E2 ) 3-e3 (-E22 -E G ) e3 ...Formula (E12) -E 2 -N(-E 23 -E G )2...Equation (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)

[0062] However, in equations (E11) to (E17), E 1 , E 2 or E 3 The side is R in equation (1) 1 Connect to E 22 , E 23 , E 24 , E 25 or E 26 The side is R 2 Connect to E G This is expressed by the following formula (E G ) and L 1 two or more E G These may be the same or different. The signs other than G are the same as the signs in equations (E1) to (E7). -Si(R 23 ) 3-k (-E 3 -) k ...Equation(E G ) However, equation (E G ) where Si side is E 22 , E 23 , E 24 , E 25 or E 26 Connect to E 3 The side is R 2 Connect to R. 23 E is an alkyl group. 3 This is a single bond, or -R 45 -B 6 -and R 45 This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms, with -C(O)NR between carbon atoms. 46 -, -C(O)-, -NR 46 - or a group having -O- or -(OSi(R 24 )2) p -O- and E greater than or equal to 2 3 They may be the same or different. k is 2 or 3. R 46 R 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 has two R 24 They may be the same or different. p is an integer from 0 to 5, and if p is 2 or greater, then (OSi(R) is 2 or greater. 24 )2) may be the same or different.

[0063] 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 standpoint of facilitating the production of compound 1 and further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. However, the lower limit of the number of carbon atoms in the alkylene group when there is a specific bond between carbon atoms is 2. R 23 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the standpoint of facilitating the production of compound 1. R 24 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the standpoint of facilitating the production of compound 1. R 24The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the viewpoint of excellent storage stability of compound 1. p is preferably 0 or 1.

[0064] R 2 This is an alkylene group or an alkylene group having an etheric oxygen atom. In an alkylene group having an etheric oxygen atom, L 1 The atom bonded may be an etheric oxygen atom, and there may be an etheric oxygen atom between the carbon atoms. R 2 When there are multiple R 2 These may be the same or different from each other. 2 Preferably, the group is represented by the following formula (H1). *-(O) a4 -(R g11 O) a5 -R g12 -** ···(H1) however, R g11 R is an alkylene group having 1 to 12 carbon atoms, and there are multiple R g11 They may be the same or different from each other. R g12 This is an alkylene group having 1 to 12 carbon atoms. a4 is either 0 or 1. a5 is a non-negative integer, * is L 1 It is a bonding hand that connects, ** is T 1 It is a bonding hand that connects to [something].

[0065] When a4 is 0, the atom with a bond* is a carbon atom, and when a4 is 1, the atom with a bond* is an oxygen atom. In compound 1, a4 may be either 0 or 1, and can be appropriately selected from the standpoint of ease of synthesis, etc. a5 is R g11This refers to the number of O repeats, and from the standpoint of durability as a surface layer, 0 to 6 is preferred, 0 to 3 is more preferred, and 0 to 1 is even more preferred. R g11 The alkylene group may be a linear or branched alkylene group having 1 to 12 carbon atoms, with a preference for an alkylene group having 1 to 6 carbon atoms, and a preference for an alkylene group having 1 to 3 carbon atoms. Furthermore, a linear alkylene group is preferred. R g12 The alkylene group may be any linear or branched alkylene group having 1 to 12 carbon atoms, with a preference for an alkylene group having 2 to 6 carbon atoms, and a preference for an alkylene group having 2 to 3 carbon atoms. Furthermore, a linear alkylene group is preferred.

[0066] L 1 However, in the case of a single bond, -R 1 -L 1 (-R 2 -T 1 ) x1 This can be expressed by the following equation (RL-1). *-R 43 -(OR 44 ) y3 -T 1 ...Formula (RL-1) however, R 43 This is a single bond or an alkylene group having 1 to 6 carbon atoms. R 44 R is an alkylene group having 1 to 6 carbon atoms. 44 If there are multiple R 44 They may be the same or different from each other. y3 is a non-negative integer, * is (OR in equation (1) f3 ) y1 The terminal R f3 This is a bonding operation that connects to [another bond]. Note, R 43 If it is a single bond, compound 1 is (OR 44 ) y3 The O at the end of is (OR) in equation (1). f3 ) y1 The terminal R f3It has a structure that directly bonds to [something]. Also, if y3 is 0, compound 1 is R 43 is T 1 It has a structure that directly bonds to [something].

[0067] T 1 T is a reactive group, 1 Due to its reactivity, compound 1 exhibits various functions. These functions include, for example, improving adhesion to the substrate surface, imparting photocurability or thermosetting properties to compound 1, imparting acidity or alkalinity to compound 1, adjusting the solubility of compound 1 in specific solvents, and functioning as a precursor when synthesizing other compounds.

[0068] T 1 Specific examples include -Ar and -SR. 10 , -NOR 10 -C(=O)R 10 , -N(R 10 )2, -N + (R 10 )3X 3 -C≡N, -C(=NR) 10 )-R 10 , -N + ≡N, -N=NR 10 , -C(=O)OR 10 -C(=O)OX 2 -C(=O)X 4 -C(=O)OC(=O)R 10 , -SO2R 10 -SO3H, -SO3X 2 -OP(=O)(-OR 10 )2, -OP(=O)(-OR 10 )(-OX 2 ), -N=C=O, -SiR a1 z1 R a11 3-z1 , -C(R 10 )=C(R 10 )2, -C≡C(R 10 ), -C(=O)N(R 10 )2, -N(R 10 )C(=O)R 10 , -Si(R10 )2-O-Si(R 10 )3, -NH-C(=O)R 10 -C(=O)NHR 10 The following are examples of groups: -I, and the groups represented below.

[0069] [ka]

[0070] however, R 10 This is a hydrogen atom, a C1-C6 alkyl group or fluoroalkyl group which may have substituents, or an aryl group which may have substituents. Ar is an aryl group which may have substituents. X 2 These are alkali metal ions or ammonium ions, X 3 It is a halide ion, X 4 It is a halogen atom, R a1 This is a hydrolyzable group or a hydroxyl group, R a11 It is a hydrocarbon group, z1 is an integer between 1 and 3. R 10 , R a1 or R a11 When there are multiple R 10 , R a1 or R a11 They may be the same or different from one another.

[0071] R 10The fluoroalkyl group in is preferably one to six carbon atoms. The fluoroalkyl group may have other substituents. Compound 1 having a fluoroalkyl group as T is a compound with a high fluorine content and exhibits excellent properties such as low refractive index, low dielectric constant, water and oil repellency, heat resistance, chemical resistance, chemical stability, and transparency. Substituents that the fluoroalkyl group may have include halogen atoms such as chlorine atoms, and those similar to those exemplified as the functionalizing group T. Ar and R 10 The aryl group in this formula includes phenyl groups, naphthyl groups, and others, and may have substituents. Substituents that the aryl group may have include fluorine atoms, halogen atoms such as chlorine atoms, C1-C6 alkyl groups, and those similar to those exemplified as functionality-granting groups T. R 10 The alkyl group in is preferably one to six carbon atoms. The alkyl group may have other substituents. Examples of substituents that the alkyl group may have include halogen atoms such as chlorine atoms, and those similar to those exemplified as the functionalizing group T.

[0072] reactive group T 1 Compound 1, which has a hydroxyl group, N-hydroxyl group, aldehyde group, ketone group, amino group, quaternary ammonium group, nitrile group, imino group, diazo group, carboxyl group, carboxylate, acid anhydride group, sulfo group, sulfonate, phosphate group, or phosphate (hereinafter, these groups are also referred to as "functionality-imparting groups T"), is endowed with various properties such as acidity, alkalinity, and hydrophilicity by the functionality-imparting groups T, and provides functions such as improved solubility in a specific solvent or improved adhesion to a specific substrate. Examples of counterions for the quaternary ammonium group include halide ions. Examples of counterions for carboxylates, sulfonates, and phosphates include alkali metal ions and ammonium ions. Groups having a carbon-carbon double bond include vinyl groups, acryloyloxy groups, methacryloyloxy groups, and olefins. Compound 1 having a carbon-carbon double bond can be combined with a photoinitiator to prepare a photocurable composition, and the cured coating obtained from this composition possesses both water-repellent and oil-repellent properties as well as hard-coat properties. Furthermore, compound 1, which has an isocyanate group, an epoxy group, a glycidyl group, an oxetanyl group, and a mercapto group, can be combined with an epoxy curing agent to prepare a thermosetting or photocurable composition, and the cured coating film obtained from this composition possesses both water-repellent and oil-repellent properties as well as hard coat properties. reactive group T 1 In T, the amide bond, ester bond, ether bond, thioether bond, siloxane bond, and urea bond are T 1 These are bonds that connect alkyl groups, fluoroalkyl groups, aryl groups, heteroaryl groups, etc., contained within the compound. These bonds may also contain other functional groups.

[0073] Reactive group T of compound 1 1 From the standpoint of synthesis, chemical stability, and adhesion to the substrate, hydroxyl groups, amino groups, or groups having a carbon-carbon double bond are preferred. Among the groups having a carbon-carbon double bond, acryloyl groups, methacryloyl groups, vinyl groups, allyl groups, or olefins are preferred.

[0074] Furthermore, when compound 1 is used as a surface treatment agent to form a surface layer with excellent durability such as abrasion resistance, T 1 It is preferable that the group has a reactive silyl group. As a group having a reactive silyl group, the group represented by the following formula (2) is preferred.

[0075] -SiR a1 z1 R a11 3-z1 ...Equation (2)

[0076] In formula (2), R a1This is a hydrolyzable group or a hydroxyl group, R a11 It is a hydrocarbon group, z1 is an integer between 1 and 3. R a1 , or R a11 If there are multiple R a1 , or R a11 These may be the same or different.

[0077] R a1 If it is a hydroxyl group, it forms a silanol (Si-OH) group together with the Si atom. Furthermore, hydrolyzable groups are groups that become hydroxyl groups through hydrolysis. The silanol group further reacts intermolecularly to form a Si-O-Si bond. Also, the silanol group undergoes a dehydration condensation reaction with the hydroxyl group on the surface of the substrate (substrate-OH) to form a chemical bond (substrate-O-Si). Compound 1 is T 1 Having one or more of these features provides excellent abrasion resistance after the surface layer is formed.

[0078] R a1 Examples of hydrolyzable groups include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, and isocyanate groups (-NCO). Preferred alkoxy groups are those having 1 to 4 carbon atoms. Preferred acyl groups are those having 1 to 6 carbon atoms. Preferred acyloxy groups are those having 1 to 6 carbon atoms.

[0079] R a1 From the viewpoint of ease of synthesis, an alkoxy group or halogen atom having 1 to 4 carbon atoms is preferred. a1 In this compound, the alkoxy group is preferably a C1-C4 alkoxy group because it provides excellent storage stability for compound 1 and suppresses outgassing during the reaction. An ethoxy group is more preferable in terms of long-term storage stability, and a methoxy group is more preferable in terms of shortening the hydrolysis reaction time. Furthermore, a chlorine atom is particularly preferred as the halogen atom.

[0080] R a11This is a hydrocarbon group. Examples of hydrocarbon groups include alkyl groups, cycloalkyl groups, alkenyl groups, and allyl groups, with alkyl groups being preferred from the viewpoint of ease of synthesis. Furthermore, from the viewpoint of ease of synthesis, the number of carbon atoms in the hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.

[0081] One T 1 Within, R a1 The number z1 can be 1 to 3, and from the viewpoint of adhesion to the substrate, 2 or 3 is preferred, and 3 is more preferred. T 1 Specific examples include -Si(OCH3)3, -SiCH3(OCH3)2, -Si(OCH2CH3)3, -SiCl3, -Si(OCOCH3)3, and -Si(NCO)3. -Si(OCH3)3 is preferred in terms of ease of handling during manufacturing.

[0082] T in one molecule of compound 1 1 The number x1 can be between 1 and 10, and from the viewpoint of ease of synthesis and ease of handling of compound 1, x1 is preferably between 1 and 6, and more preferably between 1 and 3. Compound 1 has 2 or more T molecules. 1 In cases where T 1 These may have the same structure or they may have different structures.

[0083] T 1 A specific example of a case where does not have a reactive silyl group is the following structure. However, R in the formula a R represents an alkyl group, fluoroalkyl group, or aryl group which may have substituents. b * represents a fluoroalkyl group or aryl group which may have substituents, and * represents a bond.

[0084] [ka]

[0085] Also L 1 -(R 2 -T1 ) x1 Specific examples include the groups shown in the following formula.

[0086] [ka]

[0087] A specific example of compound 1 is the compound represented by the following formula, where n and m are independent integers of 1 or more, and Me is a methyl group.

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] <Method for producing compound 1> The method for producing compound 1 is not particularly limited, but a specific example will be given. Fluoropolyether chain (OR f3 ) y1 To, R f1 One example of a method for adding is to react a compound represented by formula (3) below with a compound represented by formula (4) below.

[0103] R f31 -D 1 ...(3) D 2 -R f2 -(OR f3 ) y1 -D 3 ...(4)

[0104] however, R f31 This is a group that includes a ring structure or a chain-like hydrocarbon group having 3 or more carbon atoms, and does not contain a fluorine atom. D 1 D 2 It is a group that can react with a fluorine atom, D 2 D 1 It is a group that can react with a fluorine atom, D 3 is, -R 1 -L 1 -(R 2 -T 1 ) x1 Either or, by subsequent operations, -R 1 -L 1 -(R 2 -T 1 ) x1 It is a base that can be introduced, R f31 , D 1 and D 2 After the reaction, R in equation (1) f1 It is a base that is The other signs are the same as those in equation (1) above.

[0105] D 1 and D 2 The combinations are not particularly limited; for example, a combination of an amino group and an alkyloxycarbonyl group can be used. D 3 ni-R 1 -L 1 -(R 2 -T 1 ) x1 For information on how to implement this, refer to the literature describing known fluorine-containing ether compounds, such as International Publication No. 2017 / 038832, as described below.

[0106] Fluoropolyether chain (OR f3 ) y1 To, R f1Another example of a method for adding is a method of reacting a compound represented by formula (5) below with a compound represented by formula (6) below.

[0107] R f31 -D 4 ...(5) D 5 -(OR f3 ) y1 -D 3 ...(6)

[0108] however, D 4 D 5 It is a group that can react with a fluorine atom, D 5 D 4 It is a group that contains a group that can react with, R f31 and D 4 After the reaction, R in equation (1) f1 It is a base that is D 5 After the reaction, R in equation (1) f1 It is a base that is Other signs are the same as in equations (1), (3), and (4) above.

[0109] D 4 and D 5 The combinations are not particularly limited; for example, a combination of a hydroxyl group and a fluorine-containing olefin can be used.

[0110] [Composition] The composition of the present invention (hereinafter also referred to as "this composition") comprises compound 1 and other fluorine-containing compounds other than compound 1. This composition does not contain the liquid medium described later.

[0111] Other fluorine-containing compounds include both compounds that are inevitably included and compounds that are used in combination depending on the application.

[0112] Examples of compounds used in combination with compound 1 include known fluorine-containing ether compounds and fluorine-containing oils.

[0113] Examples of fluorinated oils include polytetrafluoroethylene (PTFE), ethylene-chlorotrifluoroethylene copolymer (ECTFE), polyvinylidene fluoride (PVDF), polyvinyl fluoride (PVF), and polychlorotrifluoroethylene (PCTFE).

[0114] Furthermore, known fluorine-containing ether compounds include, for example, fluorine-containing ether compounds that are commercially available as surface treatment agents. When this composition contains known fluorine-containing ether compounds, new effects such as complementing the properties of compound 1 may be exhibited. Examples of known fluorine-containing ether compounds include those described in the following literature. Perfluoropolyether-modified aminosilane as described in Japanese Patent Publication No. 11-029585, Silicon-containing organic fluorine polymer as described in Japanese Patent Publication No. 2874715, Organosilicon compounds described in Japanese Patent Publication No. 2000-144097, Perfluoropolyether-modified aminosilane as described in Japanese Patent Publication No. 2000-327772, Fluorinated siloxane as described in Japanese Patent Publication No. 2002-506887, Organic silicone compounds described in Japanese Patent Publication No. 2008-534696, Fluorinated modified hydrogen-containing polymer as described in Japanese Patent Publication No. 4138936, The compounds described in U.S. Patent Application Publication No. 2010 / 0129672, International Publication No. 2014 / 126064, and Japanese Patent Publication No. 2014-070163, Organosilicon compounds described in International Publication No. 2011 / 060047 and International Publication No. 2011 / 059430, Fluorine-containing organosilane compounds described in International Publication No. 2012 / 064649, A fluorooxyalkylene group-containing polymer described in Japanese Patent Publication No. 2012-72272, Fluorine-containing ether compounds as described in International Publication No. 2013 / 042732, International Publication No. 2013 / 121984, International Publication No. 2013 / 121985, International Publication No. 2013 / 121986, International Publication No. 2014 / 163004, Japanese Patent Publication No. 2014-080473, International Publication No. 2015 / 087902, International Publication No. 2017 / 038830, International Publication No. 2017 / 038832, and International Publication No. 2017 / 187775. Perfluoro(poly)ether-containing silane compounds described in Japanese Patent Publication No. 2014-218639, International Publication No. 2017 / 022437, International Publication No. 2018 / 079743, and International Publication No. 2018 / 143433. Fluoropolyether group-containing polymer-modified silanes described in Japanese Patent Publication No. 2015-199906, Japanese Patent Publication No. 2016-204656, Japanese Patent Publication No. 2016-210854, and Japanese Patent Publication No. 2016-222859. Fluorine-containing ether compounds as described in International Publication No. 2018 / 216630, International Publication No. 2019 / 039226, International Publication No. 2019 / 039341, International Publication No. 2019 / 039186, International Publication No. 2019 / 044479, Japanese Patent Publication No. 2019-44158, International Publication No. 2019 / 044479, and International Publication No. 2019 / 163282. Fluorine-containing ether compounds as described in International Publication No. 2019 / 151442, International Publication No. 2019 / 151445, International Publication No. 2020 / 066534, International Publication No. 2020 / 066533, International Publication No. 2020 / 111138, International Publication No. 2021 / 029187, International Publication No. 2021 / 111992, and Japanese Patent Publication No. 2022-19577. Furthermore, commercially available products of the compound include the KY-100 series (KY-178, KY-185, KY-195, etc.) from Shin-Etsu Chemical Co., Ltd., the SURECO AF series such as SURECO® 2101S from AGC Inc., and Optool® DSX, Optool® AES, Optool® UF503, Optool® UD509, and Optool® UD120 from Daikin Industries, Ltd.

[0115] In this composition, when compound 1 is combined with a known fluorine-containing ether compound, the content ratio may be adjusted as appropriate depending on the application. The content of compound 1 in this composition is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and even more preferably 25 to 75% by mass. By setting the content within the above range, the properties of compound 1 can be fully exhibited, and the properties of the fluorine-containing ether compound used in combination can also be fully obtained.

[0116] Compounds that are inevitably included include fluorine-containing ether compounds produced as by-products in the manufacturing process of compound 1 (hereinafter also referred to as "by-product fluorine-containing ether compounds"). Examples of by-product fluorine-containing ether compounds include unreacted compounds and fluorine-containing ether compounds in which some of the allyl groups are isomerized to inner olefins during hydrosilylation in the manufacturing of compound 1.

[0117] If this composition contains a by-product fluorine-containing ether compound, the by-product fluorine-containing ether compound can be removed by purification. Alternatively, it may be included in the composition to the extent that the properties of compound 1 are fully exhibited. This simplifies the purification process for the by-product fluorine-containing ether compound.

[0118] When no known fluorine-containing ether compounds are combined, the content of compound 1 in the composition is preferably 60% by mass or more and less than 100% by mass, more preferably 70% by mass or more and less than 100% by mass, and even more preferably 80% by mass or more and less than 100% by mass. The content of by-product fluorine-containing ether compounds is preferably greater than 0% by mass and 40% by mass or less, more preferably greater than 0% by mass and 30% by mass or less, and even more preferably greater than 0% by mass and 20% by mass or less.

[0119] If the content of compound 1 and the content of the by-product fluorine-containing ether compound are within the above range, the initial water- and oil-repellent properties, abrasion resistance, fingerprint stain removal properties, light resistance, and chemical resistance of the surface layer will be further improved.

[0120] In addition, additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reactions of hydrolyzable silyl groups are inevitably included. 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 is preferably 0 to 9.999% by mass, and more preferably 0 to 0.99% by mass, of the composition.

[0121] [Surface treatment agent] The surface treatment agent of the present invention (hereinafter also referred to as "this surface treatment agent") comprises compound 1 or this composition. This surface treatment agent is suitable for applications where it is required that the water-repellent and oil-repellent properties of the surface layer not deteriorate even when repeatedly rubbed with fingers (abrasion resistance) and that fingerprints adhering to the surface layer can be easily removed by wiping (fingerprint stain removal properties) be maintained for a long period of time, such as components that make up the surface that is touched by fingers on a touch panel, eyeglass lenses, and displays of wearable devices. Furthermore, because this surface treatment agent has excellent slip resistance, it is also suitable for use on glass-coated casings of mobile devices such as smartphones and tablet terminals. This surface treatment agent is also suitably used as an antifouling coating agent or a waterproof coating agent.

[0122] This surface treatment agent may further contain a liquid medium. In the following description, this surface treatment agent containing a liquid medium may be referred to as a coating solution. The coating solution may be a liquid, a solution, or a dispersion. The coating solution may contain compound 1, and may also contain impurities such as by-products generated during the manufacturing process of compound 1. The concentration of compound 1 in the coating solution is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass.

[0123] An organic solvent is preferred as the liquid medium. The organic solvent may be a fluorine-containing organic solvent, a non-fluorine-containing organic solvent, or a mixture of both. Specific examples of fluorinated organic solvents include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, and fluoroalcohols. As fluorinated alkanes, compounds with 4 to 8 carbon atoms are preferred. A specific example of a commercially available product is C6F 13 H (manufactured by AGC Corporation, Asahi Clean® AC-2000), C6F 13 Examples include C2H5 (manufactured by AGC, Asahi Clean® AC-6000) and C2F5CHFCHFCF3 (manufactured by Chemours, Bartrell® XF). Specific examples of fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene. As fluoroalkyl ethers, compounds having 4 to 12 carbon atoms are preferred. Specific examples of commercially available products include CF3CH2OCF2CF2H (manufactured by AGC, Asahi Clean® AE-3000), C4F9OCH3 (manufactured by 3M, Novec® 7100), C4F9OC2H5 (manufactured by 3M, Novec® 7200), and C2F5CF(OCH3)C3F7 (manufactured by 3M, Novec® 7300). Specific examples of fluorinated alkylamines include perfluorotripropylamine and perfluorotributylamine. Specific examples of fluoroalcohols include 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol. Preferred nonfluorinated organic solvents include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms. Examples include hydrocarbon organic solvents, alcohol organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, and glycol organic solvents.

[0124] Specific examples of hydrocarbon organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexyl, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.

[0125] Specific examples of alcoholic organic solvents include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3-butanediol, 1,3-butanediol, 1,3-butylene glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4-methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isotridecanol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol, 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol.

[0126] Specific examples of ketone organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, and 3,3,5-trimethylcyclohexanone and isophorone.

[0127] Specific examples of ether-based organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.

[0128] Specific examples of ester-based organic solvents include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and diethylene glycol monoethyl Examples include ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol diacetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.

[0129] Specific examples of glycol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, diethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monotert-butyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol Examples include polypropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butylene glycol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, diethylene glycol monoethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol dimethyl ether, dipropylene glycol dimethyl ether pentane, triethylene glycol dimethyl ether, and polyethylene glycol dimethyl ether.

[0130] Other organic solvents include chlorinated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds.

[0131] Specific examples of chlorinated organic solvents include dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0132] Examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0133] Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0134] Examples of siloxane compounds include hexamethyldisiloxane, octamethyltrisiloxane, and decamethyltetrasiloxane.

[0135] The coating liquid preferably contains 75 to 99.999% by mass of the liquid medium, more preferably 85 to 99.99% by mass, and even more preferably 90 to 99.9% by mass.

[0136] In addition to compound 1 and the liquid medium, the coating solution may contain other components as long as they do not impair the effects of the present disclosure. 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 coating solution is preferably 10% by mass or less, and more preferably 1% by mass or less.

[0137] The total concentration of compound 1 and other components in the coating solution (hereinafter also referred to as the "solid content concentration") is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, even more preferably 0.01 to 10% by mass, and particularly preferably 0.01 to 1% by mass. The solid content concentration of the coating solution is calculated from the mass of the coating solution before heating and the mass after heating in a convection dryer at 120°C for 4 hours.

[0138] [Goods] The article of the present invention (hereinafter also referred to as "the Article") has a surface layer formed from compound 1 or the Composition on the surface of a substrate. An example of this article will be described with reference to the drawings. Figure 1 is a schematic cross-sectional view showing a first article, which is an example of this article. The first article is an article 20 having a base material 12, a sub-layer 14, and a surface layer 22 in that order, wherein the sub-layer 14 contains an oxide containing silicon, and the surface layer 22 contains a condensate of compound 1.

[0139] The material and shape of the base material 12 may be appropriately selected depending on the intended use of the article 20. Examples of materials for the base material 12 include glass, resin, sapphire, metal, ceramic, stone, and composite materials thereof. The glass may be chemically strengthened. In particular, examples of substrates 12 that require water-repellent and oil-repellent properties include substrates for touch panels, substrates for displays, and substrates that constitute the casings of electronic devices. Substrates for touch panels and displays are translucent. "Translucent" means that the normal incidence visible light transmittance is 25% or more, in accordance with JIS R3106:1998 (ISO 9050:1990). Glass or transparent resin is preferred as the material for the substrate of the touch panel.

[0140] The base material 12 may have surface treatments such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment applied to the surface on which the underlayer 14 is provided. Surface treatment further improves the adhesion between the base material 12 and the underlayer 14, and as a result, the abrasion resistance of the surface layer 22 is further improved. As for surface treatment, corona discharge treatment or plasma treatment is preferred because it provides even better abrasion resistance to the surface layer 22.

[0141] The base layer 14 is a layer containing an oxide that includes at least silicon, and may also contain other elements. The presence of silicon oxide in the base layer 14 allows for the T of compound 1 to be determined. 1 Dehydration condensation occurs, forming Si-O-Si bonds with the base layer 14, creating a surface layer 22 with superior abrasion resistance.

[0142] The silicon dioxide content in the base layer 14 is preferably 65% ​​by mass or more, more preferably 80% by mass or more, even more preferably 85% by mass or more, and particularly preferably 90% by mass or more. If the silicon dioxide content is above the lower limit of the above range, sufficient Si-O-Si bonds are formed in the base layer 14, and the mechanical properties of the base layer 14 are sufficiently ensured. The silicon dioxide content is the remainder obtained by subtracting the total content of other elements (or the amount converted to oxides in the case of oxides) from the mass of the underlying layer 14.

[0143] From the standpoint of durability of the surface layer 22, it is preferable that the oxide in the base layer 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. Including these elements strengthens the bond between the base layer 14 and compound 1, improving abrasion resistance.

[0144] When the base layer 14 contains one or more elements selected from iron, nickel, and chromium, the total content of these elements 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, in proportion to silicon dioxide. When the underlayer 14 contains one or more selected from aluminum and zirconium, the total content of these 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 base layer 14 contains alkali metal elements, 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 base layer 14 contains platinum group elements, the total content of these elements is preferably 0.02 ppm or more and 800 ppm or less, more preferably 0.04 ppm or more and 600 ppm or less, and even more preferably 0.7 ppm or more and 200 ppm or less. Examples of platinum group elements include platinum, rhodium, ruthenium, palladium, osmium, and iridium. When the base layer 14 contains one or more elements selected from boron and phosphorus, the total content of these elements is preferably 0.003 to 9, more preferably 0.003 to 2, and more preferably 0.003 to 0.5, as the ratio of the total molar concentration of boron and phosphorus to the molar concentration of silicon, from the viewpoint of the abrasion resistance of the surface layer 22. When the base layer 14 contains alkaline earth metal elements, the total content of these elements is preferably 0.005 to 5, more preferably 0.005 to 2, and more preferably 0.007 to 2, as the ratio of the molar concentration of the total alkaline earth metal elements to the molar concentration of silicon, from the viewpoint of the abrasion resistance of the surface layer 22. Examples of alkaline earth metal elements include lithium, sodium, potassium, rubidium, and cesium.

[0145] To improve the adhesion of this composition and enhance the water-repellent, oil-repellent, and abrasion-resistant properties of article 20, the base layer 14 is preferably a silicon oxide layer containing alkali metal atoms. In the silicon oxide layer, the average concentration of alkali metal atoms in the region at a depth of 0.1 to 0.3 nm from the surface in contact with the surface layer 22 is 2.0 × 10⁻¹⁴. 19 atoms / cm 3The above is particularly preferable. On the other hand, in order to ensure sufficient mechanical properties of the silicon oxide layer, the average concentration of alkali metal atoms should be 4.0 × 10 22 atoms / cm 3 The following is preferable:

[0146] The thickness of the base layer 14 is preferably 1 to 200 nm, and particularly preferably 2 to 20 nm. If the thickness of the base layer 14 is greater than or equal to the lower limit of the above range, the adhesive improvement effect of the base layer 14 is likely to be sufficiently obtained. If the thickness of the base layer 14 is less than or equal to the upper limit of the above range, the abrasion resistance of the base layer 14 itself will be increased. Methods for measuring the thickness of the underlying layer 14 include cross-sectional observation of the underlying layer 14 using an electron microscope (SEM, TEM, etc.), and methods using optical interferometry film thickness gauges, spectroscopic ellipsometers, step gauges, etc.

[0147] A specific example of a method for forming the underlayer 14 is a method of depositing a vapor deposition material having the desired composition of the underlayer 14 onto the surface of the substrate 12. One example of a vapor deposition method is vacuum deposition. Vacuum deposition is a method in which a deposition material is evaporated in a vacuum chamber and deposited onto the surface of a substrate 12. The temperature during deposition (for example, the temperature of the boat on which the deposition material is placed when using a vacuum deposition apparatus) 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 the chamber where 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 vapor deposition material, one vapor deposition material may be used, or two or more vapor deposition materials containing different elements may be used. Methods for evaporating deposition materials include resistance heating, in which the deposition material is melted and evaporated on a resistance heating boat made of a high-melting-point metal, and electron gun methods, in which an electron beam is irradiated onto the deposition material to directly heat it, melt the surface, and evaporate it. Of the evaporation methods for deposition materials, the electron gun method is preferred because it can evaporate high-melting-point substances because it can heat locally, and because the temperature is low in areas not hit by the electron beam, eliminating the risk of reaction with the container or contamination by impurities. As the deposition material used in the electron gun method, molten granules or sintered bodies are preferred because they are less likely to scatter even if an airflow is generated.

[0148] The surface layer 22 on the underlayer 14 contains a condensate of compound 1. The condensate of compound 1 includes a form in which hydrolyzable silyl groups in compound 1 undergo hydrolysis to form silanol groups (Si-OH), and these silanol groups undergo intermolecular condensation to form Si-O-Si bonds, and a form in which silanol groups in compound 1 undergo condensation with silanol groups or Si-OM groups (where M is an alkali metal element) on the surface of the underlayer 14 to form Si-O-Si bonds. Furthermore, the surface layer 22 may contain condensates of compounds other than those included in this composition. That is, the surface layer 22 contains compounds having reactive silyl groups in a state in which some or all of the reactive silyl groups of the compound have undergone a condensation reaction.

[0149] The thickness of the surface layer 22 is preferably 1 to 100 nm, and particularly preferably 1 to 50 nm. If the thickness of the surface layer 22 is greater than or equal to the lower limit of the above range, the effect of the surface layer 22 can be fully obtained. If the thickness of the surface layer 22 is less than or equal to the upper limit of the above range, the utilization efficiency is high. The thickness of the surface layer 22 is the thickness obtained using a thin-film X-ray diffractometer. The thickness of the surface layer 22 can be calculated from the vibration period of the interference pattern obtained by the X-ray reflectivity method using a thin-film X-ray diffractometer.

[0150] Another example of the article of the present invention is the second article. The second article is an article 20 having a substrate 10 with a base layer and a surface layer 22 in that order, wherein the substrate 10 with the base layer contains an oxide containing silicon, and the surface layer 22 contains a condensate of compound 1.

[0151] In the second article, since the substrate 10 with the underlayment has the same composition as the underlayment 14 in the first article, the surface layer 22 has excellent abrasion resistance even when the surface layer 22 is directly formed on the substrate 10 with the underlayment. The material of the substrate 10 with the underlayment in the second article can be any material having the same composition as the underlayment 14, and may be, for example, a glass substrate. The details of the material of the substrate 10 with the underlayment are the same as those of the substrate 12 and the underlayment 14, so the explanation is omitted here. Furthermore, since the structure of the surface layer 22 is the same as that of the first article described above, its explanation is omitted here.

[0152] Specific examples of articles of the present invention include optical components, touch panels, anti-reflective films, anti-reflective glass, SiO2-treated glass, tempered glass, sapphire glass, quartz substrates, and mold metals, which are used as parts of the following products. Products: Car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio systems, gaming devices, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (endoscopes, etc.), photocopiers, personal computers (PCs), LCD displays, OLED displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc.

[0153] [Method of manufacturing articles] The present invention relates to a method for manufacturing an article, which involves forming a surface layer using compound 1, the present composition, or the present surface treatment agent by a dry coating method or a wet coating method.

[0154] Compound 1, this composition, and this surface treatment agent can be used directly in a dry coating method and are suitable for forming a surface layer with excellent adhesion by the dry coating method. Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferably used because it suppresses the decomposition of this composition and the equipment is simple. For vacuum deposition, a pellet-like material may be used in which compound 1 or the like is supported on a porous metal body made of a metal material such as iron or steel. The pellet-like material supported on compound 1 or the like can be manufactured by impregnating the porous metal body with a solution containing compound 1 and drying it to remove the liquid medium.

[0155] This surface treatment agent (coating solution) containing a liquid medium can be suitably used in wet coating methods. Examples of wet coating methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, Langmuir-Bludget coating, and gravure coating.

[0156] To improve the abrasion resistance of the surface layer, operations to promote the reaction between compound 1 and the substrate may be performed as needed. Such operations include heating, humidification, and light irradiation. For example, heating a substrate with a surface layer formed in a humid atmosphere can promote reactions such as the hydrolysis of hydrolyzable groups, the reaction between hydroxyl groups on the substrate surface and silanol groups, and the formation of siloxane bonds through the condensation reaction of silanol groups. After 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 onto the surface layer or wiping it with a cloth soaked in the solvent.

[0157] [Compound M1] Compound M1 is represented by the following formula (M1) and can be used, for example, in the production of compound 1.

[0158] CF2 = CF - (OR f ) y -C(=O)N(R m1 )-L m2 -C(R m2 -CH2=CH2)3···(M1)

[0159] however, R f This is a fluoroalkylene group having 1 to 6 carbon atoms. R m1 These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. L m2 These are single bonds or divalent organic groups. R m2 This is a single bond, an alkylene group, or an alkylene group having an etheric oxygen atom. y is an integer greater than or equal to 2, Multiple R f , or R m2 They may be the same or different from one another.

[0160] R f In the case where the fluoroalkylene group has 3 to 6 carbon atoms, the fluoroalkylene group with 3 to 6 carbon atoms may be linear, branched, or have a cyclic structure. (OR f ) y Specific examples and preferred embodiments are given by formula (1) (OR f3 ) y1 It is similar to that.

[0161] R m1 The number of carbon atoms in the alkyl group is 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. R m1 If the alkyl group in the formula has three or more carbon atoms, the alkyl group with three or more carbon atoms may be linear, branched, or have a ring structure.

[0162] L m2Examples of divalent organic groups include divalent aliphatic hydrocarbon groups (such as alkylene groups and cycloalkylene groups) and divalent aromatic hydrocarbon groups (such as phenylene groups), with divalent aliphatic hydrocarbon groups being preferred and alkylene groups being preferred. The number of carbon atoms in the divalent organic group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. L m2 In the case where the divalent organic group is an alkylene group having 3 or more carbon atoms, the alkylene group having 3 or more carbon atoms may be linear or branched.

[0163] R m2 A preferred embodiment of the alkylene group and the alkylene group having an etheric oxygen atom is the R of formula (1). 2 It is similar to that.

[0164] A specific example of compound M1 is the compound represented by the following formula, where n is an integer greater than or equal to 1.

[0165] [ka]

[0166] Compound M1 can be produced, for example, by the method described in the Examples section below, using compound M1-1 as a raw material.

[0167] CF2 = CF - (OR fm ) ym -C(=O)-OR m ...(M1-1)

[0168] however, R fm This is a fluoroalkylene group having 1 to 6 carbon atoms. R m is a hydrogen atom or an alkyl group, ym is an integer greater than or equal to 1, R fm When there are multiple R fm They may be the same or different from one another.

[0169] R f In the case where the fluoroalkylene group has 3 to 6 carbon atoms, the fluoroalkylene group with 3 to 6 carbon atoms may be linear, branched, or have a cyclic structure. If ym is 2 or greater, (OR fm ) ym Specific examples and preferred embodiments are given by formula (1) (OR f3 ) y1 It is similar to that.

[0170] R m The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. R m If the alkyl group in the formula has three or more carbon atoms, the alkyl group with three or more carbon atoms may be linear, branched, or have a ring structure.

[0171] ym is an integer greater than or equal to 1, preferably between 1 and 200, more preferably between 1 and 150, and even more preferably between 1 and 100.

[0172] A specific example of compound M1-1 is the compound represented by the following formula.

[0173] CF2 = CF - OCF2CF2CF2 - C(=O) - OCH3 [Examples]

[0174] The present invention will be described in detail below with reference to examples. Examples 1 to 6 are examples, and Example 7 is a comparative example. However, the present invention is not limited to these examples.

[0175] [Example 1] <Synthesis of Compound 1-1> Compound 1-1 was synthesized according to a known method. The average of n+m was 9.

[0176] [ka]

[0177] <Synthesis of Compounds 1-2> 46 g of compound (1-1) was added to a 100 mL round-bottom flask equipped with a stirring bar, and 46 g of 1,3-bis(trifluoromethyl)benzene was added and stirred until homogeneous. While stirring, 3.7 g of 2,2-di-2-allyl-4-penten-1-amine was slowly added, and the mixture was stirred at 40°C for 24 hours to obtain the crude reaction solution. The obtained crude reaction solution was purified by column chromatography to obtain 10 g of compound 1-2.

[0178] [ka]

[0179] (NMR spectra of compounds 1-2) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(3H), 5.2(6H), 4.1(3H), 3.4(2H), 2.2(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -120(2F), -121(2F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0180] <Synthesis of Compounds 1-3> 2.0 g of compound 1-2 was added to a 50 mL round-bottom flask equipped with a stirring bar, followed by 0.084 g of 1-aminodecane and 2.1 g of 1,3-bis(trifluoromethyl)benzene. The mixture was stirred at 40°C for 24 hours to obtain the crude reaction solution. The crude reaction solution was purified by column chromatography to obtain 1.8 g of compound 1-3.

[0181] [ka]

[0182] (NMR spectra of compounds 1-3) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.4(1H), 6.0(3H), 5.2(6H), 3.5(2H), 3.4(2H), 2.2(6H), 1.8(2H), 1.4(14H), 0.9(3H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -121(4F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0183] <Synthesis of Compounds 1-4> In a 50 mL round-bottom flask equipped with a stirring bar, 1.0 g of compound 1-3, 0.10 g of trimethoxysilane, 0.0010 g of aniline, 1.0 g of AC-6000, and 0.0033 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were added and stirred at 40°C for 24 hours, followed by distillation under reduced pressure at 0 hPa and 60°C for 24 hours. In this way, 1.1 g of compound 1-4 was obtained.

[0184] [ka]

[0185] (NMR spectra of compounds 1-4) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.4(1H), 3.6(27H), 3.5(2H), 3.4(2H), 1.8(2H), 1.4(26H), 0.9(3H), 0.6(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -121(4F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0186] [Example 2] <Synthesis of Compound 2-1> In a 50 mL round-bottom flask equipped with a stirring bar, 2.0 g of compound 1-2, 0.15 g of stearylamine, and 2.1 g of 1,3-bis(trifluoromethyl)benzene were added and stirred at 40°C for 24 hours to obtain a crude reaction solution. The obtained crude reaction solution was purified by column chromatography to obtain 1.7 g of compound 2-1.

[0187] [ka]

[0188] (NMR spectrum of compound 2-1) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.4(1H), 6.0(3H), 5.2(6H), 3.5(2H), 3.4(2H), 2.2(6H), 1.8(2H), 1.4(30H), 0.9(3H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -121(4F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0189] <Synthesis of Compound 2-2> In a 50 mL round-bottom flask equipped with a stirring bar, 1.0 g of compound 2-1, 0.10 g of trimethoxysilane, 0.0010 g of aniline, 1.0 g of AC-6000, and 0.0033 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were added and stirred at 40°C for 24 hours, followed by distillation under reduced pressure at 0 hPa and 60°C for 24 hours. In this way, 1.1 g of compound 2-2 was obtained.

[0190] [ka]

[0191] (NMR spectrum of compound 2-2) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.4(1H), 3.6(27H), 3.5(2H), 3.4(2H), 1.8(2H), 1.4(42H), 0.9(3H), 0.6(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -121(4F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0192] [Example 3] <Synthesis of Compound 3-1> In a 50 mL round-bottom flask equipped with a stirring bar, 1.5 g of compound 1-2, 0.070 g of 1-adamantanamine, and 1.5 g of 1,3-bis(trifluoromethyl)benzene were added and stirred at 40°C for 24 hours to obtain a crude reaction solution. The obtained crude reaction solution was purified by column chromatography to obtain 1.1 g of compound 3-1.

[0193] [ka]

[0194] (NMR spectrum of compound 3-1) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.4(1H), 6.0(3H), 5.2(6H), 3.5(2H), 3.4(2H), 2.2(6H), 2.1(3H), 1.8(6H), 1.6(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -121(4F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0195] <Synthesis of Compound 3-2> In a 50 mL round-bottom flask equipped with a stirring bar, 1.0 g of compound 3-1, 0.10 g of trimethoxysilane, 0.0010 g of aniline, 1.0 g of AC-6000, and 0.0033 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were added and stirred at 40°C for 24 hours, followed by distillation under reduced pressure at 0 hPa and 60°C for 24 hours. In this way, 1.1 g of compound 3-2 was obtained.

[0196] [ka]

[0197] (NMR spectrum of compound 3-2) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.4(1H), 3.6(27H), 3.5(2H), 3.4(2H), 2.1(3H), 1.8(6H), 1.6(6H), 1.3(6H), 1.1(6H), 0.6(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -81--86(40F), -90(36F), -121(4F), -126(40F), -127(4F), -128--134(4F), -138--140(2F).

[0198] [Example 4] <Synthesis of Compound 4-1> 8.1 g of methyl 2,2,3,3,4,4,hexafluoro-4-[(trifluorovinyl)oxy]butanoate and 60 g of carbon tetrachloride were added to a 500 mL three-necked flask equipped with a stirring bar. To this, 30 g of 6.0 M hydrochloric acid aqueous solution was added dropwise to 5.3 g of calcium hypochlorite to generate chlorine gas, and the chlorine gas diluted with nitrogen gas was bubbled through the solution. After stirring continued at 0°C for 2 hours while bubbling nitrogen gas, the solution was quenched with thiosulfate aqueous solution and the organic phase was concentrated. In this way, 6.5 g of compound 4-1 was obtained.

[0199] [ka]

[0200] (NMR spectrum of compound 4-1) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm):4.0(3H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -71(2F), -77(1F), -84(1F), -85(1F), -118(2F), -127(2F).

[0201] <Synthesis of Compound 4-2> In a 300 mL round-bottom flask equipped with a stirring bar, 2.1 g of sodium tetraborate and 40 mL of tetrahydrofuran were added. Then, a solution of 6.5 g of compound 4-1 and 0.60 g of methanol dissolved in 20 g of tetrahydrofuran was added dropwise at 0°C, and stirring was continued for 15 hours. After adding 50 g of dichloromethane and 2.0 M aqueous hydrochloric acid solution, the mixture was separated, and the organic phase was concentrated using an evaporator. In this way, 6.0 g of compound 4-2 was obtained.

[0202] [ka]

[0203] (NMR spectrum of compound 4-2) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 4.1(2H), 2.4(1H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -71(2F), -77(1F), -84(1F), -85(1F), -123(2F), -127(2F).

[0204] <Synthesis of Compound 4-3> 6.0 g of compound 4-2 and 2.5 g of potassium carbonate were added to a 300 mL round-bottom flask equipped with a stirring bar. The mixture was then stirred at 120°C, and 36.6 g of 2,2,3,3,4,4-hexafluoro-4-[(trifluorovinyl)oxy]butan-1-ol was added dropwise, while stirring was continued at 120°C for 16 hours. After that, the contents of the round-bottom flask were allowed to cool to room temperature (23°C), and 100 g each of AC-2000 and hydrochloric acid aqueous solution were added and separated. The organic layer was concentrated using an evaporator. The resulting crude solution was purified by column chromatography to obtain 29.9 g of compound 4-3.

[0205] [ka]

[0206] (NMR spectrum of compound 4-3) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.0-5.8(7H), 4.4-4.3(14H), 4.1(2H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -70(2F), -77(1F), -84(1F), -85--87(15F), -90(14F), -121(14F), -124(2F), -127(16F), -145(7F).

[0207] <Synthesis of Compound 4-4> In a 100 mL round-bottom flask equipped with a stirring bar, 29.0 g of compound 4-3, 2.8 g of sodium fluoride powder, and 30 g of AC-2000 were added. While stirring, 4.1 g of perfluoro(2-methyl-3-oxahexanoyl)fluoride was added, and stirring was continued for 14 hours to obtain a crude reaction solution. The obtained crude reaction solution was filtered to obtain 33.5 g of compound 4-4.

[0208] [ka]

[0209] (NMR spectrum of compound 4-4) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm):6.0-5.8(7H), 4.8(2H)4.6-4.4(14H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -70(2F), -77(1F), -81(1F), -83--84(7F), -85--87(17F), -90(14F), -121(16F), -127(16F), -131(2F), -134(1F), -145(7F).

[0210] <Synthesis of Compounds 4-5> 250 g of CFE-419 (ClCF2CFClCF2OCF2CF2Cl) was added to a 500 mL metal reactor, and nitrogen gas was bubbled in, followed by the bubbled fluorine gas diluted with nitrogen gas. While continuing to bubble the fluorine gas, 213 g of a solution of compound 4-4 diluted with 32.1 g of CFE-419 was introduced over 4 hours. Furthermore, a 0.1 mass% CFE-419 solution of benzene was introduced over 1 hour, followed by the bubbled fluorine gas diluted with nitrogen gas, and then the bubbled nitrogen gas to obtain the crude solution. The obtained crude solution was concentrated in an evaporator to obtain 35.3 g of compound 4-5.

[0211] [ka]

[0212] (NMR spectra of compounds 4-5) 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -70(2F), -77(1F), -81(1F), -83--85(38F), -86(1F), -90(28F), -127(32F), -131(2F), -134(1F).

[0213] <Synthesis of Compounds 4-6> 35.3 g of compound 4-5, 2.8 g of sodium fluoride, and 35 g of methanol were added to a 200 mL round-bottom flask equipped with a stirring bar, and the mixture was stirred for 16 hours to obtain a crude reaction solution. The crude reaction solution was then filtered, and the resulting filtrate was concentrated using an evaporator to obtain 30.4 g of compound 4-6.

[0214] [ka]

[0215] (NMR spectra of compounds 4-6) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm):4.1(3H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -70(2F), -77(1F), -83--85(30F), -86(1F), -90(28F), -121(2F), -127(30F).

[0216] <Synthesis of Compounds 4-7> In a 200 mL round-bottom flask equipped with a stirring bar, 10.0 g of compound 4-6, 1.6 g of 2,2-di-2-allyl-4-penten-1-amine, and 10 g of AC-6000 were added and stirred at 60°C for 22 hours to obtain a crude reaction solution. The obtained crude reaction solution was purified by column chromatography to obtain 5.7 g of compound 4-7.

[0217] [ka]

[0218] (NMR spectra of compounds 4-7) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(3H), 5.1(6H), 3.3(2H), 2.1(6H). 19 F-NMR (376.46 MHz, CDCl) 3 CFCl3 ) σ(ppm): -70(2F), -77(1F), -83--85(30F), -86(1F), -90(28F), -122(2F), -127(30F).

[0219] <Synthesis of Compounds 4-8> 2.3 g of compound 4-7, 0.26 g of zinc powder, 2.3 g of acetic acid, and 0.8 g of dimethylformamide were added to a 100 mL round-bottom flask equipped with a stirring bar, and the mixture was stirred at 140°C for 15 hours to obtain a crude reaction solution. The obtained crude reaction solution was filtered, 50 g of AC-2000 and 1.0 M hydrochloric acid aqueous solution were added, and the mixture was separated. The organic phase was concentrated using an evaporator to obtain 2.0 g of compound 4-8.

[0220] [ka]

[0221] (NMR spectra of compounds 4-8) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(3H), 5.1(6H), 3.3(2H), 2.1(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(28F), -86(2F), -90(28F), -116(1F), -122(2F), -124(1F), -127(30F), -138(1F).

[0222] <Synthesis of Compounds 4-9> In a 50 mL round-bottom flask equipped with a stirring bar, 0.60 g of compound 4-8, 0.035 g of potassium hydroxide aqueous solution, 0.038 g of 1-adamantan methanol, and 1.0 g of 1,3-bis(trifluoromethyl)benzene (manufactured by AGC Seimi Chemical Co., Ltd.) were added and stirred at 80°C for 17 hours. Then, 20 g of AC-2000 and 1.0 M hydrochloric acid aqueous solution were added to obtain the crude reaction solution. The crude reaction solution was separated, the organic phase was concentrated using an evaporator, and then purified by column chromatography to obtain 0.30 g of compound 4-9.

[0223] [ka]

[0224] (NMR spectra of compounds 4-9) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(4H), 5.1(6H), 3.8(2H), 3.3(2H), 2.1(6H), 2.0(3H), 1.7(6H), 1.5(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(30F), -90(30F), -122(2F), -127(30F), -145(1F).

[0225] <Synthesis of Compound 4-10> In a 50 mL round-bottom flask equipped with a stirring bar, 0.30 g of compound 4-9, 0.054 g of trimethoxysilane, 0.000092 g of aniline, 1.0 g of AC-6000, and 0.0013 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were added and stirred at 60°C for 4 hours, followed by distillation under reduced pressure at 0 hPa and 60°C for 17 hours. In this way, 0.32 g of compound 4-10 was obtained.

[0226] [ka]

[0227] (NMR spectra of compounds 4-10) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(1H), 3.8(2H), 3.6(27H), 3.3(2H), 2.0(3H), 1.7(6H), 1.5(6H), 1.4(6H), 1.1(6H), 0.6(6H). 19F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(30F), -90(30F), -122(2F), -127(30F), -145(1F).

[0228] [Example 5] <Synthesis of Compound 5-1> In a 50 mL round-bottom flask equipped with a stirring bar, 0.60 g of compound 4-8, 0.035 g of potassium hydroxide aqueous solution, 0.041 g of 1-decanol, and 1.0 g of 1,3-bis(trifluoromethyl)benzene (manufactured by AGC Seimi Chemical Co., Ltd.) were added and stirred at 80°C for 17 hours. Then, 20 g of AC-2000 and 1.0 M hydrochloric acid aqueous solution were added and the mixture was separated. The resulting organic phase was concentrated using an evaporator and purified by column chromatography to obtain 0.30 g of compound 5-1.

[0229] [ka]

[0230] (NMR spectrum of compound 5-1) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(4H), 5.1(6H), 4.0(2H), 3.3(2H), 2.1(6H), 1.5-1.2(16H), 0.9(3H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(30F), -90(30F), -122(2F), -127(30F), -145(1F).

[0231] <Synthesis of Compound 5-2> In a 50 mL round-bottom flask equipped with a stirring bar, 0.30 g of compound 5-1, 0.056 g of trimethoxysilane, 0.000096 g of aniline, 1.0 g of AC-6000, and 0.0013 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were added and stirred at 60°C for 4 hours, followed by distillation under reduced pressure at 0 hPa and 60°C for 17 hours. In this way, 0.32 g of compound 5-2 was obtained.

[0232] [ka]

[0233] (NMR spectrum of compound 5-2) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(1H), 4.0(2H), 3.6(27H), 3.3(2H), 1.5-1.3(22H), 1.1(6H), 0.9(3H), 0.6(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(30F), -90(30F), -122(2F), -127(30F), -145(1F).

[0234] [Example 6] <Synthesis of Compound 6-1> In a 50 mL round-bottom flask equipped with a stirring bar, 0.60 g of compound 4-8, 0.035 g of potassium hydroxide aqueous solution, 0.078 g of 1-eicosanol, and 1.0 g of 1,3-bis(trifluoromethyl)benzene (manufactured by AGC Seimi Chemical Co., Ltd.) were added and stirred at 80°C for 17 hours. Then, 20 g of AC-2000 and 1.0 M hydrochloric acid aqueous solution were added and the mixture was separated. The resulting organic phase was concentrated using an evaporator and purified by column chromatography to obtain 0.32 g of compound 6-1.

[0235] [ka]

[0236] (NMR spectrum of compound 6-1) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(4H), 5.1(6H), 4.0(2H), 3.3(2H), 2.1(6H), 1.5-1.2(36H), 0.9(3H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(30F), -90(30F), -122(2F), -127(30F), -145(1F).

[0237] <Synthesis of Compound 6-2> In a 50 mL round-bottom flask equipped with a stirring bar, 0.32 g of compound 6-1, 0.057 g of trimethoxysilane, 0.000097 g of aniline, 1.0 g of AC-6000, and 0.0013 g of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex were added and stirred at 60°C for 4 hours, followed by distillation under reduced pressure at 0 hPa and 60°C for 17 hours. In this way, 0.33 g of compound 6-2 was obtained.

[0238] [ka]

[0239] (NMR spectrum of compound 6-2) 1 H-NMR (400.13MHz, CDCl3, TMS) σ(ppm): 6.6(1H), 6.0(1H), 4.0(2H), 3.6(27H), 3.3(2H), 1.5-1.3(42H), 1.1(6H), 0.9(3H), 0.6(6H). 19 F-NMR (376.46MHz, CDCl3, CFCl3) σ(ppm): -83--85(30F), -90(30F), -122(2F), -127(30F), -145(1F).

[0240] [Example 7] A perfluoropolyether group-containing silane compound (F) described in International Publication No. 2019-151445 was used as compound 7. CF3CF2CF2[OCF(CF3)CF2] 11 OCF(CF3)CONHCH2C[CH2CH2CH2Si(OCH3)3]3...Formula (7)

[0241] [Manufacturing of goods] Each compound obtained in Examples 1-7 was mixed with C4F9OC2H5 (Novec® 7200, manufactured by 3M Corporation) as a medium to prepare a coating solution with a solid content of 0.05%. The substrate was dipped into the coating solution and left for 30 minutes before being removed (dip coating method). The coating film was dried at 200°C for 30 minutes and washed with AK-225 to obtain an article with a surface layer on the surface of the substrate. Chemically strengthened glass was used as the substrate.

[0242] [evaluation] The following evaluation tests were conducted using each of the obtained items. The results of the evaluation tests are shown in Table 1.

[0243] <Method for measuring contact angle> 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 measuring device (Kyowa Interface Science Co., Ltd., DM-500). Measurements were taken at five different locations on the surface of the surface layer, and the average value was calculated. The 2θ method was used to calculate the contact angle.

[0244] (Initial contact angle) The initial water contact angle and initial n-hexadecane contact angle of the surface layer were measured using the measurement method described above. The evaluation criteria are as follows. Initial water contact angle: ◎ (Excellent): 115 degrees or higher. ○ (Good): 110 degrees or higher and less than 115 degrees. △ (Acceptable): 100 degrees or more and less than 110 degrees. × (Not allowed): Below 100 degrees. Initial n-hexadecane contact angle: ◎ (Excellent): 66 degrees or higher. ○ (Good): 65 degrees or higher and less than 66 degrees. △ (Acceptable): 63 degrees or higher and less than 65 degrees. × (Not allowed): Below 63 degrees.

[0245] <Abrasion resistance (steel wool)> For the surface layer, a reciprocating traverse tester (manufactured by KNT Co., Ltd.) was used in accordance with JIS L0849:2013 (ISO 105-X12:2001). Steel wool bonstar (#0000) was traversed 15,000 times at a pressure of 98.07 kPa and a speed of 320 cm / min, and the water contact angle was measured using the method described above. The smaller the decrease in water repellency (water contact angle) after friction, the smaller the decrease in performance due to friction and the better the abrasion resistance. The evaluation criteria are as follows. ◎(Excellent): The change in water contact angle after 15,000 cycles is 2 degrees or less. ○ (Good): The change in water contact angle after 15,000 cycles is greater than 2 degrees and less than or equal to 5 degrees. △ (Acceptable): The change in water contact angle after 15,000 cycles is greater than 5 degrees and less than or equal to 10 degrees. × (Not acceptable): The change in water contact angle after 15,000 cycles exceeds 10 degrees.

[0246] <Slip resistance> The coefficient of dynamic friction of the surface layer of artificial skin (Idemitsu Technofine, PBZ13001) was measured using a load-variable friction and wear testing system (Shinto Kagaku Co., Ltd., HHS2000) under the conditions of a contact area of ​​3 cm × 3 cm and a load of 0.98 N. A higher coefficient of dynamic friction indicates better slip resistance. The evaluation criteria are as follows. ◎(Excellent): The coefficient of kinetic friction is 0.6 or higher. ○ (Good): The coefficient of kinetic friction is 0.5 or higher and less than 0.6. △ (Acceptable): The coefficient of kinetic friction is 0.4 or higher and less than 0.5. × (Not acceptable): The coefficient of kinetic friction is less than 0.4.

[0247] <Fingerprint stain removal> An artificial fingerprint solution (a solution consisting of oleic acid and squalene) was applied to the flat surface of a silicone rubber stopper. Excess oil was then wiped off with a nonwoven fabric (Asahi Kasei Corporation, Bencot® M-3) to prepare a fingerprint stamp. The fingerprint stamp was placed on the surface layer and pressed down with a load of 9.8 N for 10 seconds. The haze at the fingerprint site was measured with a haze meter and set as the initial value. The fingerprint site was wiped with a reciprocating traverse tester (KNT Corporation) equipped with tissue paper, under a load of 4.9 N. The haze value was measured after each reciprocating wipe, and the number of wipes required to reduce the haze to 10% or less of the initial value was determined. Fewer wipes indicate easier removal of fingerprint stains and superior fingerprint stain removal performance. The evaluation criteria are as follows. ◎(Excellent): Wiping required 3 times or less. ○ (Good): Wipeable 4-5 times. △ (Acceptable): Wipes 6-8 times. × (Not allowed): Wiping more than 9 times.

[0248] [Table 1]

[0249] As shown in Table 1, the compounds of the present invention were confirmed to be able to form a surface layer with excellent friction resistance, fingerprint stain removal properties, and slip resistance (Examples 1-6). [Industrial applicability]

[0250] Articles having a surface layer containing compound 1 are useful, for example, as optical articles, touch panels, anti-reflective films, anti-reflective glass, SiO2-treated glass, tempered glass, sapphire glass, quartz substrates, mold metals, etc., used as parts of the following products. Products: Car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio systems, gaming devices, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (such as endoscopes), photocopiers, personal computers (PCs), LCD displays, OLED displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc. [Explanation of Symbols]

[0251] 10 Substrate with undercoat 12 Base material 14 Base layer 20 Goods 22 Surface layer

Claims

1. A compound represented by the following formula (1). R ｆ１ -R ｆ２ -(OR ｆ３ ) ｙ１ -R １ -L １ -(R ２ -T １ ) ｘ１ ・・・(1) however, R ｆ１ This is an organic group that contains a cyclic structure or a chain-like hydrocarbon group having 3 or more carbon atoms and does not have a fluorine atom. R ｆ２ This is a single bond or a fluoroalkylene group having 1 to 6 carbon atoms. R ｆ３ This is a fluoroalkylene group having 1 to 6 carbon atoms. R １ This is a single bond, a fluoroalkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 20 carbon atoms, or an alkylene group having 1 to 20 carbon atoms with an etheric oxygen atom. L １ It is a single bond or a 1+x1 valent group, R ２ This is an alkylene group, or an alkylene group having an etheric oxygen atom. T １ It is a reactive group, y1 is an integer greater than or equal to 2, x1 is an integer between 1 and 10. R ｆ３ , R ２ , or T １ When there are multiple R ｆ３ , R ２ , or T １ They may be the same or different from one another.

2. Said T １ is -Ar, -SR １０ ,-NOR １０ ,-C(=O)R １０ ,-N(R １０ ), -N ２ ,-N ＋ (R １０ ), -N ３ X ３ ,-C≡N, -C(=NR １０ )-R １０ ,-N ＋ ≡N, -N=N R １０ ,-C(=O)OR １０ ,-C(=O)OX ２ ,-C(=O)X ４ ,-C(=O)OC(=O)R １０ ,-SO ２ R １０ ,-SO ３ H, -SO ３ X ２ ,-O-P(=O)(-OR １０ ), -O-P(=O)(-OR ２ )(-OX １０ ), -N=C=O, -SiR ２ ａ１ ｚ１ R ａ１１ ３－ｚ１ １０ ,-C(R １０ )=C(R ２ [[ID=6V]] １０ ), -C≡C(R １０ ), -C(=O)N(R ２ ), -N(R １０ ), -N(R １０ )C(=O)R １０ ,-Si(R ２ ), -Si(R １０ )-O-Si(R ３ ), -NH-C(=O)R １０ ,-C(=O)NHR １０ ,-I,​​​ 【Chemistry 1】 The compound according to claim 1, which is any of the following. however, R １０ This is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have substituents, a fluoroalkyl group having 1 to 6 carbon atoms which may have substituents, or an aryl group which may have substituents. Ar is an aryl group which may have substituents. X ２ These are alkali metal ions or ammonium ions, X ３ It is a halide ion, X ４ It is a halogen atom, R ａ１ This is a hydrolyzable group or a hydroxyl group, R ａ１１ It is a hydrocarbon group, z1 is an integer between 1 and 3. R １０ , R ａ１ , or R ａ１１ When there are multiple R １０ , R ａ１ , or R ａ１１ They may be the same or different from one another.

3. Said T １ However, -SiR ａ１ ｚ１ R ａ１１ ３－ｚ１ The compound according to claim 2.

4. The aforementioned R ｆ１ The compound according to claim 1, wherein the ring structure in comprises at least one selected from the group consisting of an aliphatic hydrocarbon ring and an aromatic ring.

5. The aforementioned R ｆ１ The compound according to claim 1, wherein the group is represented by the following formula (2). X-L-Y-...(2) however, X is an aliphatic hydrocarbon ring group which may have substituents, an aromatic ring group which may have substituents, or a chain hydrocarbon group having 3 or more carbon atoms. L is a single bond, an alkylene group which may have a substituent, *-P(R Ｌ１ )-R Ｌ２ -**, or -Si(R Ｌ３ ) ２ -, where R Ｌ１ is an alkyl group or a phenyl group, R Ｌ２ is an alkylene group, two R Ｌ３ are each independently an alkyl group or a phenyl group, * is the bonding position with X of formula (2), ** is the bonding position with Y of formula (2), and when L is an alkylene group which may have a substituent, X is an aliphatic hydrocarbon ring group which may have a substituent, or an aromatic ring group which may have a substituent, Y is -O-, -NR １１ C(=O)-, or -O-C(=O)-, and R １１ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or -L-X. R １１ If the condition is -L-X, then the multiple L or X values ​​may be the same or different from each other.

6. The compound according to claim 5, wherein Y is -O-.

7. The R ｆ１ The compound according to claim 1, wherein the organic group in R contains a ring structure.

8. A composition comprising the compound described in claim 1 and another fluorine-containing compound.

9. A surface treatment agent comprising the compound described in claim 1, or the composition described in claim 8.

10. The surface treatment agent according to claim 9, which is a stain-resistant coating agent or a waterproof coating agent.

11. The surface treatment agent according to claim 9, further comprising a liquid medium.

12. An article having a surface layer formed using the compound described in claim 1 or the composition described in claim 8 on the surface of a substrate.

13. The article according to claim 12, wherein the surface layer is provided on the surface of a component that constitutes the surface of a touch panel that is touched by a finger.

14. The article according to claim 12, which is an optical component.

15. A method for manufacturing an article, comprising forming a surface layer by a dry coating method using the surface treatment agent described in claim 9.

16. A method for manufacturing an article, comprising forming a surface layer by a wet coating method using the surface treatment agent described in claim 11.

17. A compound represented by the following formula (M1). CF ２ =CF-(OR ｆ ) ｙ -C(=O)N(R ｍ１ )-L ｍ２ -C(R ｍ２ -CH ２ =CH ２ ) ３ ・・・(M1) however, R ｆ This is a fluoroalkylene group having 1 to 6 carbon atoms. R ｍ１ These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. L ｍ２ These are single bonds or divalent organic groups. R ｍ２ This is a single bond, an alkylene group, or an alkylene group having an etheric oxygen atom. y is an integer greater than or equal to 2, Multiple R ｆ , or R ｍ２ They may be the same or different from one another.

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