Fluorine-containing compounds, compositions containing fluorine-containing compounds, coating solutions, articles, and methods for producing the same.

Abstract

Provided are a fluorine-containing compound capable of forming a surface layer that is excellent in abrasion resistance and fingerprint stain removability even when the chain length of the fluorine-containing organic group is shortened; a fluorine-containing compound-containing composition; a coating liquid; an article having a surface layer on its surface; and a method for producing the same. [(R f -A-)2N-] a1 Q 1 [-T] b1 (R f : a fluoroalkyl group or a group having -O- between carbon atoms of a fluoroalkyl group having 2 or more carbon atoms, A: a divalent organic group having no fluorine atom, Q 1 : a1+b1 valent organic group, T: -Si(R) 3-c (L) c , R: alkyl group, L: hydrolyzable group or hydroxyl group, a1: integer of 1 or more, b1: integer of 2 or more, c: 2 or 3).

Description

[Technical Field]

[0001] The present invention relates to fluorine-containing compounds, fluorine-containing compounds-containing compositions, coating solutions, articles, and methods for producing the same. [Background technology]

[0002] Fluorine-containing compounds having fluorine-containing organic groups such as fluoroalkyl groups and fluoropolyether chains, and hydrolyzable silyl groups, can form a surface layer on the substrate surface exhibiting high lubricity, water repellency, and oil repellency, and are therefore suitable for use as surface treatment agents. Surface treatment agents containing fluorine-containing 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.

[0003] As fluorine-containing compounds that can form a surface layer on the surface of a substrate that has excellent abrasion resistance and fingerprint stain removal properties, fluorine-containing compounds having multiple fluoropolyether chains and multiple hydrolyzable silyl groups have been proposed (compounds (1-2), (1-4), (1-5), (1-7), and (1-8) in paragraph

[0049] of Patent Document 1). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2017 / 187775 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] Surface treatment agents are sometimes used for surface treatment of the back surface (the side opposite the display screen) of mobile devices such as smartphones and tablet devices. When the present inventors evaluated a substrate with a surface layer obtained by surface-treating the entire main surface of a substrate using a surface treatment agent containing a fluorine-containing compound, it was found that although the fingerprint stain removability of the surface layer was good, the anti-slip property was poor (i.e., it was slippery). For example, when the substrate with a surface layer is a mobile device, there is a risk that the mobile device will slip when operating the mobile device or when placing it on a desk or the like. Therefore, the surface layer formed on the back surface of the mobile device is required to have anti-slip property in addition to abrasion resistance and fingerprint stain removability. According to the studies by the present inventors, it has been found that when the chain length of the fluorine-containing organic group is shortened, the anti-slip property of the surface layer tends to improve. However, when the chain length of the fluorine-containing organic group is shortened, the abrasion resistance and fingerprint stain removability of the surface layer tend to decrease.

[0006] An object of the present invention is to provide a fluorine-containing compound, a fluorine-containing compound-containing composition, a coating liquid, an article having a surface layer excellent in abrasion resistance and fingerprint stain removability even when the chain length of the fluorine-containing organic group is shortened, and a method for producing the same. [Means for Solving the Problems]

[0007] The present invention provides a fluorine-containing compound, a fluorine-containing compound-containing composition, a coating liquid, an article, and a method for producing an article having the configurations of the following [1] to

[14] . [1] A fluorine-containing compound which is a compound represented by the following formula (1A) or a compound represented by the following formula (1B). [(R -A-)2N-] a1 Q 1 [-T] b1 ···(1A) [T-] b2 [(R f -A-)2N-] a2 Q 2 -N(R 10 ) 1-a3 (-A-R f ) a3 -A-Q f -A-N(R10 ) 1-a3 (-AR f ) a3 -Q 2 [-N(-AR f )2] a2 [-T] b2 ...(1B) however, R f is a fluoroalkyl group (where at least one fluorine atom is bonded to the carbon atom at the A end), or a group having -O- between carbon atoms of a fluoroalkyl group having 2 or more carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A end), and 2 or more R in formulas (1A) and (1B). f They may be the same or different. Q f This is a fluoroalkylene group (where at least one fluorine atom is bonded to the carbon atom at the A end), or a fluoroalkylene group having -O- between carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A end), A is a divalent organic group that does not contain a fluorine atom, and the two or more A's in formulas (1A) and (1B) may be the same or different. Q 1 This is an organic group with a1+b1 valency, Q 2 This is an a² + b² + 1-valent organic group, and has two Q 2 They may be the same or different. R 10 is a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and has 2 or more R 10 They may be the same or different. T is -Si(R) 3-c (L) c And, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and two or more Ls may be the same or different. a1 is an integer greater than or equal to 1, a2 is an integer greater than or equal to 0, and [(R f-A-)2N-] may be the same or different, a3 is 0 or 1, and a2 + a3 ≥ 1, b1 and b2 are each an integer of 2 or more, and two or more Ts may be the same or different, c is 2 or 3. However, in the compound represented by the formula (1B), Q f The two monovalent groups linked through may be the same or different.

[0008] [2] The fluorine-containing compound of [1], wherein the compound represented by the formula (1B) is a compound represented by the following formula (1BX). {[T-] b2 [(R f -A-)2N-] a2 Q 2 -N(R 10 ) 1-a3 (-A-R f ) a3 -A-}2Q f ···(1BX) [3] The fluorine-containing compound of [1] or [2], wherein R f is a group represented by the following formula (g1a). R f1 -(OR f2 ) m - ···(g1a) However, [[]]R f1 is a fluoroalkyl group having 1 to 6 carbon atoms (however, when m is 0, at least one fluorine atom is bonded to the terminal carbon atom on the A side). R f2 is a fluoroalkylene group having 1 to 6 carbon atoms (however, at least one fluorine atom is bonded to the terminal carbon atom on the A side of R f2 bonded to A). m is an integer of 0 or more, and when m is 2 or more, (OR f2 ) m may consist of two or more OR f2 . [4] The above R f 0 and Q fA fluorine-containing compound of any of [1] to [3], wherein the molecular weights of each are 50 to 1000. [5] The above A is -(CH2) n -, -C(O)-, -(CH2) n -NHC(O)-, -C(O)NH-(CH2) n -C(O)- or -C(O)NH-(CH2) n - (where n is an integer greater than or equal to 1) - a fluorine-containing compound from any of [1] to [4].

[0009] [6] Q 1 However, the base is represented by formula (g2-1) (where a1=d1+d3 and b1=d2+d4), the base is represented by formula (g2-2) (where a1=e1 and b1=e2), the base is represented by formula (g2-3) (where a1=1 and b1=2), the base is represented by formula (g2-4) (where a1=h1 and b1=h2), or the base is represented by formula (g2-5) (where a1=i1 and b1=i2), The aforementioned Q 2 A fluorine-containing compound of any of [1] to [5], wherein the group is represented by formula (g2-1) (where a2+1=d1+d3 and b2=d2+d4), formula (g2-2) (where a2+1=e1 and b2=e2), formula (g2-3) (where a2+1=1 and b2=2), formula (g2-4) (where a2+1=h1 and b2=h2), or formula (g2-5) (where a2+1=i1 and b2=i2). [ka] (-Q 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -) e2 ...(g2-2) -Q 13 -N(-Q 23 -)2···(g2-3) (-Q 14 -) h1 Z(-Q24 -) h2 ···(g2 - 4) (-Q 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -) i2 ···(g2 - 5) However, In formulas (g2 - 1) to (g2 - 5), Q 12 , Q 13 , Q 14 and Q 15 sides are connected to the nitrogen atom of [(R f -A-)2N-] or -N(R 10 ) 1-a3 (-A-R f ) a3 -, and Q 22 , Q 23 , Q 24 and Q 25 sides are connected to T, Q 11 is a single bond, -O-, an alkylene group, or a group having -O- between carbon - carbon atoms of an alkylene group with 2 or more carbon atoms, Q 12 is a single bond, -C(O)-, or an alkylene group, and when Q 1 or Q 2 has two or more Q 12 , the two or more Q 12 may be the same or different, Q 13 is an alkylene group, Q 14 is, when the atom in Z to which Q 14 is bonded is a carbon atom, Q 12 , and when the atom in Z to which Q 14 is bonded is a nitrogen atom, Q 13 , and when Q 1 or Q 2 has two or more Q 14 , the two or more Q 14 may be the same or different, Q 15 is an alkylene group, and Q 1 or Q 2 when Q15 If you have 2 or more Q 15 They may be the same or different. Q 22 This is an alkylene group, an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, a group having -C(O)NH-, -C(O)-, or -O- at the end of the alkylene group that is not connected to Si, or a group having -C(O)NH-, -C(O)-, or -O- between the carbon atoms of an alkylene group having 2 or more carbon atoms and having -C(O)NH-, -C(O)-, or -O- at the end that is not connected to Si, and 2 or more Q 22 They may be the same or different. Q 23 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 Q 23 They may be the same or different. Q 24 Q 24 If the atom at Z to which the bond is formed is a carbon atom, then Q 22 Q 24 If the atom at Z to which it is bonded is a nitrogen atom, then Q 23 And Q is 2 or greater. 24 They may be the same or different. Q 25 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 or more Q 25 They may be the same or different. Z is Q 14 It has a carbon or nitrogen atom that is directly bonded to it and Q 24 It is a group having a ring structure with a1+b1 or a2+b2+1 valency, which has a carbon or nitrogen atom to which it is directly bonded. R 1 Q is a hydrogen atom or an alkyl group, 1 Or Q 2 R 1 If you have 2 or more of these, then 2 or more R 1 They may be the same or different. R 2 is a hydrogen atom or an alkyl group, R 3 It is an alkyl group, d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1 + d3 is an integer between 1 and 4, and d2 + d4 is an integer between 2 and 5. e1 is 1 or 2, e2 is 2 or 3, and e1+e2 is 3 or 4. h1 is an integer greater than or equal to 1, and h2 is an integer greater than or equal to 2. i1 is either 1 or 2, i2 is either 2 or 3, and i1+i2 is either 3 or 4.

[0010] [7] A fluorine-containing composition characterized by containing one or more of the fluorine-containing compounds described in [1] to [6] above, and other fluorine-containing compounds. [8] A coating liquid characterized by comprising any of the fluorine-containing compounds in [1] to [6] above or a fluorine-containing compound-containing composition in [7] and a liquid medium. [9] An article having a surface layer formed from any of the fluorine-containing compounds in [1] to [6] or the fluorine-containing compound-containing composition of [7] on the surface of a substrate.

[10] The article of [9] having the surface layer on the surface of a component that constitutes the surface of the touch panel that is touched by a finger.

[11] A method for manufacturing an article, characterized by treating the surface of a substrate by a dry coating method using any of the fluorine-containing compounds in [1] to [6] or the fluorine-containing compound-containing composition in [7], thereby forming a surface layer on the surface of the substrate made of the fluorine-containing compound or the fluorine-containing compound-containing composition.

[12] A method for manufacturing an article, characterized by applying the coating liquid [8] to the surface of a substrate by a wet coating method and drying it to form a surface layer on the surface of the substrate that is made of the fluorine-containing compound or the fluorine-containing compound-containing composition.

[0011]

[13] A fluorine-containing compound that is represented by the following formula (2A) or the following formula (2B). [(R f -A-)2N-] a1 Q 10 [-CH=CH2] b1 ...(2A) [CH2=CH-] b2 [(R f -A-)2N-] a2 Q 20 -N(-AR f )-AQ f -AN(-AR f )-Q 20 [-N(-AR f )2] a2 [-CH=CH2] b2 ...(2B) however, R f R is a fluoroalkyl group (where at least one fluorine atom is bonded to the carbon atom at the A end), or a group having -O- between carbon atoms of a fluoroalkyl group having 2 or more carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A end), and 2 or more R in formulas (2A) and (2B). f They may be the same or different. Q f This is a fluoroalkylene group (where at least one fluorine atom is bonded to the carbon atom at the A end), or a fluoroalkylene group having -O- between carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A end), A is a divalent organic group that does not contain a fluorine atom, and the two or more A's in formulas (2A) and (2B) may be the same or different. Q 10 This is an organic group with a1+b1 valency, Q 20 This is an a² + b² + 1-valent organic group, and has two Q 20 They may be the same or different. a1 is an integer of 1 or more, a2 is an integer of 0 or more, and two or more [(R f -A-)2N-] may be the same or different, b1 and b2 are each an integer of 2 or more. However, in the compound represented by the formula (2B), the two monovalent groups linked via Q f may be the same or different.

[14] The fluorine-containing compound represented by the formula (2B) is the fluorine-containing compound of

[13] , which is a compound represented by the following formula (2BX). {[CH2=CH-] b2 [(R f -A-)2N-] a2 Q 20 -N(-A-R f )-A-}2Q f ···(2BX) [Advantages of the Invention]

[0012] According to the fluorine-containing compound of the present invention, even when the chain length of the fluorine-containing organic group is shortened, a surface layer excellent in fingerprint stain removability and abrasion resistance can be formed. According to the fluorine-containing compound-containing composition of the present invention, even when the chain length of the fluorine-containing organic group of the fluorine-containing compound is shortened, a surface layer excellent in fingerprint stain removability and abrasion resistance can be formed. According to the coating liquid of the present invention, even when the chain length of the fluorine-containing organic group of the fluorine-containing compound is shortened, a surface layer excellent in fingerprint stain removability and abrasion resistance can be formed. The article of the present invention has a surface layer excellent in fingerprint stain removability and abrasion resistance even when the chain length of the fluorine-containing organic group of the fluorine-containing compound is shortened. According to the method for producing an article of the present invention, an article having a surface layer excellent in fingerprint stain removability and abrasion resistance can be produced even when the chain length of the fluorine-containing organic group of the fluorine-containing compound is shortened. [Embodiments for Carrying Out the Invention]

[0013] In this specification, the compound represented by formula (1A) will be referred to as compound (1A), and the compound represented by formula (1B) will be referred to as compound (1B). The same applies to compounds represented by other formulas. Compound (1A) and compound (1B) will also be collectively referred to as compound (1). Furthermore, the group represented by formula (g1a) will be denoted as group (g1a). Other groups represented by other formulas will be denoted similarly. The chemical formula for an oxyfluoroalkylene unit shall be written with the oxygen atom located to the left of the fluoroalkylene group. The following terms used in this specification have the meanings set forth below. A "hydrolyzable silyl group" refers to a group that can undergo hydrolysis to form a silanol group (Si-OH). A hydrolyzable silyl group or silanol group is, for example, T(-Si(R)) in formula (1A) or formula (1B). 3-c (L) c Hereafter, hydrolyzable silyl groups and silanol groups will be collectively referred to as "reactive silyl groups." The term "surface layer" refers to the layer formed on the surface of the substrate. If the fluorine-containing compound is a mixture of multiple fluorine-containing compounds with different fluoropolyether chain lengths, then R f Or Q f The "molecular weight" is, 1 H-NMR and 19 The number-average molecular weight is calculated by determining the number (average value) of oxyfluoroalkylene units relative to the terminal group using F-NMR. Examples of terminal groups include R in formula (g1a). f1 The term T in equations (1A) and (1B) is an example. Fluorine-containing compounds are R f Ya Q f If the chain length of the fluorine-containing compound is single, then R f Ya Q f The "molecular weight" is, 1 H-NMR and 19 F-NMR f Ya Q f This is the molecular weight calculated by determining the structure of the molecule.

[0014] [Fluorine-containing compounds] The fluorine-containing compound of the present invention is compound (1A) or compound (1B). [(R f -A-)2N-] a1 Q 1 [-T] b1 ...(1A) [T-] b2 [(R f -A-)2N-] a2 Q 2 -N(R 10 ) 1-a3 (-AR f ) a3 -AQ f -AN(R 10 ) 1-a3 (-AR f ) a3 -Q 2 [-N(-AR f )2] a2 [-T] b2 ...(1B) However, R f is a fluoroalkyl group (where at least one fluorine atom is bonded to the carbon atom at the A end), or a group having -O- between carbon atoms of a fluoroalkyl group having 2 or more carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A end), and 2 or more R in formulas (1A) and (1B). f They may be the same or different. Q f A is a fluoroalkylene group (where at least one fluorine atom is bonded to the carbon atom at the A end), or a fluoroalkylene group having -O- between carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A end). A is a divalent organic group that does not have a fluorine atom, and the two or more A's in formulas (1A) and (1B) may be the same or different. Q 1 This is an organic group with a1+b1 valency. Q 2 This is an a² + b² + 1-valent organic group, and has two Q 2 They may be the same or different. 10 is a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and has 2 or more R 10They may be the same or different. T is -Si(R) 3-c (L) c R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, c is 2 or 3, and 2 or more Ls may be the same or different. a1 is an integer of 1 or more, a2 is an integer of 0 or more, and 2 or more [(R f -A-)2N-] may be the same or different. a3 is 0 or 1, and a2+a3≧1. b1 and b2 are integers greater than or equal to 2, and T greater than or equal to 2 may be the same or different.

[0015] In the above compound (1B), Q f The two monovalent groups linked via may be the same or different. That is, the [T-] group of compound (1B) b2 [(R f -A-)2N-] a2 Q 2 -N(R 10 ) 1-a3 (-AR f ) a3 In the two bases represented by -A-, A and Q 2 , R 10 , R f At least one of T, a2, a3, and b2 may be different. As for compound (1B), Q is chosen because it is easy to manufacture compound (1B). f A compound (1B) in which the two monovalent groups linked via are identical is preferred. Hereinafter, Q f A compound (1B) in which two monovalent groups linked via a nucleotide polymorphism are identical is represented by the following formula (1BX). {[T-] b2 [(R f -A-)2N-] a2 Q 2 -N(R 10 ) 1-a3 (-AR f ) a3 -A-}2Q f ...(1BX)

[0016] Compound (1A) is R fIt has multiple instances of R at the end. f Compound (1A) having multiple of these compounds exhibits excellent removal of fingerprints from the surface layer. Compound (1B) has Q f In addition, R f It has multiple of these. Q f In addition, R f Compound (1B) having multiple such compounds exhibits excellent fingerprint stain removal properties on the surface layer. Compound (1) has multiple reactive silyl groups. Compound (1), having multiple reactive silyl groups at its terminals, forms a strong chemical bond with the substrate, resulting in excellent abrasion resistance of the surface layer. For a1, 1 to 6 is preferred, 1 to 4 is more preferred, and 1 or 2 is particularly preferred, from the standpoint of ease of producing compound (1A) and further superior abrasion resistance and fingerprint stain removal of the surface layer. For a2, 0 to 6 is preferred, 0 to 4 is more preferred, and 0 to 2 is particularly preferred, from the standpoint of ease of producing compound (1B) and further superior abrasion resistance and fingerprint stain removal of the surface layer. For b1, 2 to 6 is preferred, 2 to 5 is more preferred, and 2 to 4 is particularly preferred, from the standpoint of ease of manufacturing compound (1A) and further superior abrasion resistance and fingerprint stain removal properties of the surface layer. For b2, 2 to 6 is preferred, 2 to 5 is more preferred, and 2 to 4 is particularly preferred, from the standpoint of ease of manufacturing compound (1B) and further superior abrasion resistance and fingerprint stain removal properties of the surface layer. For a3, 1 is preferred because it facilitates the production of compound (1B) and further improves the abrasion resistance and fingerprint stain removal properties of the surface layer. When a3 is 0, R 10 As the hydrocarbon group, an alkyl group is preferred because it facilitates the production of compound (1B). 10 The number of carbon atoms in the hydrocarbon group is preferably 1 to 3, and particularly preferably 1 to 2.

[0017] R f R is a monovalent fluorine-containing organic group. fAs such, fluoropolyether chains are preferred because they offer even better fingerprint stain removal properties for the surface layer. A fluoropolyether chain is a group having multiple -O- atoms between the carbon atoms of a fluoroalkyl group. Fluoropolyether chains typically have oxyfluoroalkylene units. f In particular, perfluoropolyether chains are more preferable because they offer superior abrasion resistance and fingerprint stain removal properties for the surface layer. Q f It is a divalent fluorine-containing organic group. Q f As such, a fluoropolyether chain is preferred because it offers even better fingerprint stain removal properties for the surface layer. f In particular, perfluoropolyether chains are more preferable because they offer superior abrasion resistance and fingerprint stain removal properties for the surface layer.

[0018] R f and Q f The molecular weights of each are preferably 50 to 1000, more preferably 100 to 900, and particularly preferably 200 to 800, in order to achieve both good fingerprint stain removal and slip resistance of the surface layer. f and Q f If the molecular weight is above the lower limit of the above range, the fingerprint stain removal performance of the surface layer will be even better. f and Q f If the molecular weight is below the upper limit of the above range, the slip resistance of the surface layer will be even better. R f and Q f The molecular weight of the material is preferably 1500 to 10000, more preferably 2000 to 8000, and particularly preferably 2500 to 6000, from the viewpoint of further superior abrasion resistance and fingerprint stain removal of the surface layer. f and Q f If the molecular weight is above the lower limit of the above range, the abrasion resistance and fingerprint stain removal properties of the surface layer are further improved. f and Q f If the molecular weight is below the upper limit of the above range, the abrasion resistance of the surface layer will be even better.

[0019] R f For example, the group (g1a) can be cited. R f1 -(OR f2 ) m - ···(g1a) However, R f1 R is a fluoroalkyl group having 1 to 6 carbon atoms (however, if m is 0, at least one fluorine atom is bonded to the carbon atom at the A end), and f2 This is a fluoroalkylene group having 1 to 6 carbon atoms (where R is bonded to A). f2 At least one fluorine atom is bonded to the carbon atom at the A end of the A side. ) and m is a non-negative integer, and if m is 2 or greater, (OR f2 ) m is two or more ORs f2 It may consist of the following:

[0020] Q f Examples include groups having the group (g1b). -R f2 (OR f2 ) m’ - ···(g1b) However, R f2 This is a fluoroalkylene group having 1 to 6 carbon atoms (where R is bonded to A). f2 At least one fluorine atom is bonded to the carbon atom at the A end of the A side. ) and m' is an integer greater than or equal to 1, and if m' is 2 or greater, (OR f2 ) m’ is two or more ORs f2 It may consist of the following:

[0021] R f1 If the carbon number is between 1 and 6, the abrasion resistance and fingerprint stain removal properties of the surface layer are further improved. f1 The number of carbon atoms in the fluoroalkyl group is preferably 1 to 4, and particularly preferably 1 to 3, from the viewpoint of further improving the abrasion resistance and fingerprint stain removal properties of the surface layer. R f1 As such, perfluoroalkyl groups are preferred because they offer even better abrasion resistance and fingerprint stain removal properties for the surface layer. f1Compound (1A), in which the parent molecule is a perfluoroalkyl group, has a CF3- terminus. Compound (1A), with a CF3- terminus, can form a surface layer with low surface energy, thus further improving the abrasion resistance and fingerprint stain removal properties of the surface layer. R f1 Examples include CF3-, CF3CF2-, CF3CF2CF2-, CF3CF2CF2CF2-, CF3CF2CF2CF2CF2-, CF3CF2CF2CF2CF2CF2-, CF3CF(CF3)-, etc.

[0022] R f2 If the carbon number is between 1 and 6, the abrasion resistance and fingerprint stain removal properties of the surface layer are further improved. R f2 As such, linear fluoroalkylene groups are preferred because they offer even better abrasion resistance and fingerprint stain removal properties for the surface layer. R f2 As such, a perfluoroalkylene group is preferred because it offers even better abrasion resistance and fingerprint stain removal properties for the surface layer. All R f2 The proportion of perfluoroalkylene groups is preferably 60 mol% or more, more preferably 80 mol% or more, and particularly preferably 100 mol%, from the viewpoint of further improving the abrasion resistance and fingerprint stain removal properties of the surface layer.

[0023] When sufficient slip resistance is required for the surface layer, m is preferably an integer between 0 and 30, more preferably an integer between 0 and 20, and particularly preferably an integer between 0 and 10. If m is less than or equal to the upper limit of the above range, the slip resistance of the surface layer is further improved. When sufficient slip resistance is required for the surface layer, m' is preferably an integer between 1 and 30, more preferably an integer between 1 and 20, and particularly preferably an integer between 1 and 10. If m' is less than or equal to the upper limit of the above range, the slip resistance of the surface layer is further improved. When sufficient abrasion resistance and fingerprint stain removal properties are required for the surface layer, m and m' are preferably integers between 2 and 200, more preferably between 5 and 150, and particularly preferably between 10 and 100. If m and m' are above the lower limit of the above range, the abrasion resistance and fingerprint stain removal properties of the surface layer are further improved. If m and m' are below the upper limit of the above range, the abrasion resistance of the surface layer is further improved. In other words, if the number-average molecular weight of compound (1) is too large, the number of hydrolyzable silyl groups per unit molecular weight decreases, and the abrasion resistance of the surface layer decreases.

[0024] Ure f2 In other words, examples of oxyfluoroalkylene units include OCHF, OCF2CHF, OCHFCF2, OCF2CH2, OCH2CF2, OCF2CF2CHF, OCHFCF2CF2, OCF2CF2CH2, OCH2CF2CF2, OCF2CF2CF2CH2, OCH2CF2CF2CF2, OCF2CF2CF2CF2CH2, OCH2CF2CF2CF2CF2, OCF2CF2CF2CF2CF2CH2, OCH2CF2CF2CF2CF2CF2, OCF2, OCF2CF2CF2CF2, OCF(CF3)CF2, OCF2CF2CF2CF2CF2, OCF(CF3)CF2, OCF2CF2CF2CF2CF2, OCF2CF2CF2CF2CF2CF2, etc.

[0025] (OR f2 ) m and (OR f2 ) m’ In this case, two or more OR f2 If present, each OR f2 The order in which they are combined is not limited. For example, if OCF2 and OCF2CF2 exist, OCF2 and OCF2CF2 may be placed randomly, alternately, or in blocks. Two or more ORs f2 The existence of two or more ORs with different numbers of carbon atoms means f2 The existence of two or more ORs with different numbers of hydrogen atoms. f2 The existence of two or more ORs with different hydrogen atom positions. f2The existence of two or more ORs that have the same number of carbon atoms but differ in the presence or absence of side chains or the type of side chains (number of side chains, number of carbon atoms in side chains, etc.) f2 This refers to the existence of something. Two or more ORs f2 Regarding the arrangement, for example, {(OCF2) m1 (OCF2CF2) m2 The structure represented by} represents a random arrangement of m1 (OCF2) and m2 (OCF2CF2). Also, (OCF2CF2-OCF2CF2CF2CF2) m5 The structure represented by this symbol indicates that m5 (OCF2CF2) and m5 (OCF2CF2CF2CF2) are arranged alternately.

[0026] (OR f2 ) m and (OR f2 ) m’ Preferably, it has at least a part of the following structure. {(OCF2) m1 (OCF2CF2) m2}, (OCF2CF2) m3 , (OCF2CF2CF2) m4 , (OCF2CF2-OCF2CF2CF2CF2) m5 , (OCF2CF2CF2CF2CF2) m6 (OCF2) m7 , (OCF2CF2CF2CF2CF2) m6 (OCF2CF2) m7 , (OCF2CF2CF2CF2CF2CF2) m6 (OCF2) m7 , (OCF2CF2CF2CF2CF2CF2) m6 (OCF2CF2) m7 , (OCF2CF2CF2CF2CF2-OCF2) m8 , (OCF2CF2CF2CF2CF2-OCF2CF2)m8 , (OCF2CF2CF2CF2CF2CF2-OCF2) m8 , (OCF2CF2CF2CF2CF2CF2-OCF2CF2 m8 , (OCF2-OCF2CF2CF2CF2CF2) m8 , (OCF2-OCF2CF2CF2CF2CF2CF2) m8 , (OCF2CF2-OCF2CF2CF2CF2CF2) m8 , (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m8 , (OCF(CF3)CF2) m9 . However, m1, m2, m3, m4, m5, m6, m7, m8, and m9 are integers greater than or equal to 1. The upper limits of m1, m2, m3, m4, m5, m6, m7, m8, and m9 are adjusted to match the upper limit of m.

[0027] (OR f2 ) m and (OR f2 ) m’ The following are preferred in terms of ease of producing compound (1). {(OCF2) m1 (OCF2CF2) m2}OCF2, (OCF2CF2) m3 OCF2, (OCF2CF2CF2) m4 OCF2CF2, (OCF2CF2)2{(OCF2) m1 (OCF2CF2) m2}OCF2, (OCF2CF2-OCF2CF2CF2CF2) m5 OCF2CF2OCF2CF2CF2, (OCF2-OCF2CF2CF2CF2CF2) m8 OCF2OCF2CF2CF2CF2, (OCF2-OCF2CF2CF2CF2CF2CF2) m8 OCF2OCF2CF2CF2CF2CF2, (OCF2CF2-OCF2CF2CF2CF2CF2) m8 OCF2CF2OCF2CF2CF2CF2, (OCF2CF2-OCF2CF2CF2CF2CF2CF2) m8 OCF2CF2OCF2CF2CF2CF2CF2, (OCF(CF3)CF2) m9 OCF(CF3).

[0028] A is a divalent linking group. The organic group A can be any group containing a carbon atom. Examples of organic groups A include divalent hydrocarbon groups (alkylene groups, cycloalkylene groups, phenylene groups, and combinations thereof), and bonds containing a carbon atom (-C(O)NR). 4 -, -C(O)O-, -C(O)-, -NHC(O)O-, -NHC(O)NR 4 - etc.), bonded with a divalent hydrocarbon group (-C(O)NR 4 -, -C(O)O-, -C(O)-, -O-, -NR 4 -, -S-, -NHC(O)O-, -NHC(O)NR 4 -, -SO2NR 4 - Combinations with other items are examples. However, R 4 These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. As for A, from the point that compound (1) is easy to produce, -(CH2) n -, -C(O)-, -(CH2) n -NHC(O)-, -C(O)NH-(CH2) n -C(O)- or -C(O)NH-(CH2) n - is preferable. However, n is an integer of 1 or more. n is preferably an integer between 1 and 10, and particularly preferably 1 or 2.

[0029] Q 1 This is a linear or branched linking group with a1+b1 valency. Q 2This is a linear or branched linking group with a² + b² + 1 valency. Q 1 The organic group preferably has at least one branching point (hereinafter referred to as "branching point P") selected from the group consisting of C, N, Si, a ring structure, and an a1+b1 valent organopolysiloxane residue. A specific branched chain is bound to branching point P. Q 2 The organic group preferably has at least one branching point (hereinafter referred to as "branching point P'") selected from the group consisting of C, N, Si, a ring structure, and an a2+b2+1 valent organopolysiloxane residue. A specific branched chain is bound to branching point P'. Here, the specific branched chain is a fluorine-containing organic group (R f Or Q f ) or a chain having a reactive silyl group within its chain.

[0030] As for the ring structure, a type 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, given the ease of producing compound (1) and the superior abrasion resistance, light resistance, and chemical resistance of the surface layer, with the ring structure shown in the following formula being particularly 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).

[0031] [ka]

[0032] Examples of a1+b1 valent organopolysiloxane residues or a2+b2+1 valent organopolysiloxane residues include the following groups. However, R in the following formula 5 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 5 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and particularly preferably 1.

[0033] [ka]

[0034] Q 1 and Q 2 The organic group is -C(O)NR 6 -, -C(O)O-, -C(O)-, -O-, -NR 6 -, -S-, -NHC(O)O-, -NHC(O)NR 6 -, -SO2NR 6 -, -Si(R 6 )2-, -OSi(R 6 ) may have at least one bond selected from the group consisting of 2- and divalent organopolysiloxane residues (hereinafter referred to as "bond B"). However, R 6 These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

[0035] Examples of divalent organopolysiloxane residues include the group shown in the following formula. However, R in the following formula 7 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 7 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and particularly preferably 1.

[0036] [ka]

[0037] As for bond B, -C(O)NR is chosen because it facilitates the production of compound (1). 6 -, -C(O)-, and -O- are preferred, and -C(O)NR is preferred because it further improves the light resistance and chemical resistance of the surface layer. 6 - or -C(O)- is particularly preferred.

[0038] Q 1 Examples include combinations of two or more divalent hydrocarbon groups and one or more branch points P, or combinations of two or more hydrocarbon groups, one or more branch points P, and one or more bonds B. Q 2Examples include combinations of two or more divalent hydrocarbon groups and one or more branch points P', or combinations of two or more hydrocarbon groups, one or more branch points P', and one or more bonds B. Examples of divalent hydrocarbon groups include divalent aliphatic hydrocarbon groups (alkylene groups, cycloalkylene groups, etc.) and divalent aromatic hydrocarbon groups (phenylene groups, etc.). The number of carbon atoms in the divalent hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and particularly preferably 1 to 4.

[0039] Q of the above combination 1 As for ease of producing compound (1A), the following groups are preferred: group (g2-1) (where a1=d1+d3 and b1=d2+d4), group (g2-2) (where a1=e1 and b1=e2), group (g2-3) (where a1=1 and b1=2), group (g2-4) (where a1=h1 and b1=h2), or group (g2-5) (where a1=i1 and b1=i2). Q of the above combination 2 As for ease of producing compound (1B), the following groups are preferred: group (g2-1) (where a2+1=d1+d3 and b2=d2+d4), group (g2-2) (where a2+1=e1 and b2=e2), group (g2-3) (where a2+1=1 and b2=2), group (g2-4) (where a2+1=h1 and b2=h2), or group (g2-5) (where a2+1=i1 and b2=i2).

[0040] [ka]

[0041] (-Q 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -) e2 ...(g2-2) -Q 13 -N(-Q 23 -)2···(g2-3) (-Q14 -) h1 Z(-Q 24 -) h2 ...(g2-4) (-Q 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -) i2 ...(g2-5)

[0042] However, in equations (g2-1) to (g2-5), Q 12 Q 13 Q 14 and Q 15 The side is [(R f -A-)2N-] or -N(R 10 ) 1-a3 (-AR f ) a3 - Connects to the nitrogen atom, Q 22 Q 23 Q 24 and Q 25 The side is connected to T, Q 11 Q is a single bond, -O-, an alkylene group, or an alkylene group having -O- between carbon atoms, and 12 Q is a single bond, -C(O)-, or an alkylene group. 1 Or Q 2 Q 12 If you have 2 or more Q 12 Q can be the same or different, 13 Q is an alkylene group, 14 Q 14 If the atom at Z to which the bond is formed is a carbon atom, then Q 12 Q 14 If the atom at Z to which it is bonded is a nitrogen atom, then Q 13 Q 1 Or Q 2 Q 14 If you have 2 or more Q 14 Q can be the same or different, 15 Q is an alkylene group, 1 Or Q 2 Q 15 If you have 2 or more Q15 Q can be the same or different, 22 This is an alkylene group, an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, a group having -C(O)NH-, -C(O)-, or -O- at the end of the alkylene group that is not connected to Si, or a group having -C(O)NH-, -C(O)-, or -O- between the carbon atoms of an alkylene group having 2 or more carbon atoms and having -C(O)NH-, -C(O)-, or -O- at the end that is not connected to Si, and 2 or more Q 22 Q can be the same or different, 23 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 Q 23 Q can be the same or different, 24 Q 24 If the atom at Z to which the bond is formed is a carbon atom, then Q 22 Q 24 If the atom at Z to which it is bonded is a nitrogen atom, then Q 23 And Q is 2 or greater. 24 Q can be the same or different, 25 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 or more Q 25 They may be the same or different, and Z is Q 14 It has a carbon or nitrogen atom that is directly bonded to it and Q 24 R is a group having a ring structure with a1+b1 or a2+b2+1 valency, which has a carbon or nitrogen atom directly bonded to it. 1 Q is a hydrogen atom or an alkyl group, 1 Or Q 2 R 1 If you have 2 or more of these, then 2 or more R 1 They may be the same or different, R 2 is a hydrogen atom or an alkyl group, and R 3i1 is an alkyl group, d1 is an integer from 0 to 3, preferably 1 or 2, d2 is an integer from 0 to 3, preferably 1 or 2, d1+d2 is an integer from 1 to 3, d3 is an integer from 0 to 3, preferably 1 or 2, d4 is an integer from 0 to 3, preferably 1 or 2, d3+d4 is an integer from 1 to 3, d1+d3 is an integer from 1 to 4, preferably 2 or 3, d2+d4 is an integer from 2 to 5, preferably 2 to 4, e1 is 1 or 2, e2 is 2 or 3, e1+e2 is 3 or 4, h1 is an integer of 1 or more, preferably 1 or 2, h2 is an integer of 2 or more, preferably 2 or 3, i1 is 1 or 2, i2 is 2 or 3, and i1+i2 is 3 or 4.

[0043] Q 11 Q 12 Q 13 Q 14 Q 15 Q 22 Q 23 Q 24 and Q 25 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and particularly 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.

[0044] The ring structure in Z is the ring structure described above, and the preferred form is also the same. Note that the ring structure in Z is Q 14 Ya Q 24 Because they bond directly, for example, an alkylene group is linked to the ring structure, and Q is attached to that alkylene group. 14 Ya Q 24 They will not be connected.

[0045] R 1 , R 2 and R 3 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1). h1 is preferably 1 to 6, more preferably 1 to 4, even more preferably 1 or 2, and particularly preferably 1, from the standpoint of ease of producing compound (1) and further superior abrasion resistance and fingerprint stain removal properties of the surface layer. For h2, 2 to 6 is preferred, 2 to 4 is more preferred, and 2 or 3 is particularly preferred, from the standpoint of facilitating the production of compound (1) and further improving the abrasion resistance and fingerprint stain removal properties of the surface layer.

[0046] Q 1 Other forms of the base include base(g2-6) (where a1=d1+d3 and b1=k), base(g2-7) (where a1=e1 and b1=k), base(g2-8) (where a1=1 and b1=k), base(g2-9) (where a1=h1 and b1=k), or base(g2-10) (where a1=i1 and b1=k). Q 2 Other forms of the base include base(g2-6) (where a2+1=d1+d3 and b2=k), base(g2-7) (where a2+1=e1 and b2=k), base(g2-8) (where a2+1=1 and b2=k), base(g2-9) (where a2+1=h1 and b2=k), or base(g2-10) (where a2+1=i1 and b2=k).

[0047] [ka]

[0048] (-Q 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -G) e2 ...(g2-7) -Q 13 -N(-Q 23 -G)2···(g2-8) (-Q 14 -) h1 Z(-Q 24 -G)h2 ...(g2-9) (-Q 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 25 -G) i2 ...(g2-10)

[0049] However, in equations (g2-6) to (g2-10), Q 12 Q 13 Q 14 and Q 15 The side is [(R f -A-)2N-] or -N(R 10 ) 1-a3 (-AR f ) a3 - is connected to the nitrogen atom, the G side is connected to T, G is a group (g3), Q 1 Or Q 2 The 2 or greater Gs that exist in the equation may be the same or different, and the signs of the elements other than G are the same as the signs in equations (g2-1) to (g2-5). -Si(R 8 ) 3-k (-Q 3 -) k ...(g3) However, in equation (g3), the Si side is Q. 22 Q 23 Q 24 and Q 25 Connect to Q 3 The side is connected to T, R 8 Q is an alkyl group, 3 This refers to an alkylene group, an alkylene group having -C(O)NH-, -C(O)-, or -O- between carbon atoms, or -(OSi(R 9 )2) p -O- and Q is 2 or greater. 3 They may be the same or different, k is 2 or 3, and R 9 is an alkyl group, a phenyl group, or an alkoxy group, and has two R 9 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. 9)2) may be the same or different.

[0050] Q 3 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and particularly 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 8 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1). R 9 The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1). R 9 The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the viewpoint of excellent storage stability of compound (1). p is preferably 0 or 1.

[0051] T is -Si(R) 3-c (L) c It is a reactive silyl group. The number of carbon atoms in the alkyl group of R is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of compound (1).

[0052] The hydrolyzable group L is a group that becomes a hydroxyl group through hydrolysis. That is, Si-L, where L is a hydrolyzable group, becomes a silanol group (Si-OH) through hydrolysis. The silanol group then undergoes further dehydration condensation reactions with other molecules to form a Si-O-Si bond. In addition, the silanol group undergoes dehydration condensation reactions with the hydroxyl group on the surface of the substrate (substrate-OH) to form a chemical bond (substrate-O-Si). Examples of hydrolyzable groups include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, and isocyanate groups. As alkoxy groups, alkoxy groups having 1 to 6 carbon atoms are preferred. As aryloxy groups, aryloxy groups having 3 to 10 carbon atoms are preferred. However, the aryl group of the aryloxy group includes heteroaryl groups. As halogen atoms, chlorine atoms are preferred. As acyl groups, acyl groups having 1 to 6 carbon atoms are preferred. As acyloxy groups, acyloxy groups having 1 to 6 carbon atoms are preferred. As L, alkoxy groups and halogen atoms are preferred because they facilitate the production of compound (1). As L, alkoxy groups having 1 to 4 carbon atoms are preferred because they produce less outgassing during coating and compound (1) has excellent storage stability. Ethoxy groups are particularly preferred when long-term storage stability of compound (1) is required, and methoxy groups are particularly preferred when the reaction time after coating is to be short. Option c is particularly preferred because it results in stronger adhesion between the surface layer and the substrate. The multiple T groups in compound (1) may be the same or different. It is preferable that they be the same group from the standpoint of facilitating the production of compound (1).

[0053] Examples of compound (1) include the compound shown below. The compound shown below is preferred because it is easy to manufacture industrially, easy to handle, and has superior water and oil repellency, abrasion resistance, fingerprint stain removal, lubricity, chemical resistance, light resistance, and chemical resistance of the surface layer, with particularly excellent light resistance. R in the compound shown below f Or Q f This is R in equation (1) above. f Or Q f The same applies to the preferred form.

[0054] Q 1 Examples of compounds (1A) in which (g2-1) is the base (g2-1) include the following compound.

[0055] [ka]

[0056] Q 1 Examples of compounds (1A) in which the group (g2-2) is shown include the following compound.

[0057] [ka]

[0058] [ka]

[0059] Q 1 Examples of compounds (1A) in which (g2-3) is the group include the following compound.

[0060] [ka]

[0061] Q 1 Examples of compounds (1A) in which (g2-4) is the group include the following compound.

[0062] [ka]

[0063] Q 1 Examples of compounds (1A) in which (g2-7) is the base are the compounds shown in the following formula.

[0064] [ka]

[0065] Q 2 Examples of compounds (1B) in which (g2-1) is the base (g2-1) include the compound shown in the following formula.

[0066] [ka]

[0067] Q 2 Examples of compounds (1B) in which the group (g2-2) is shown include the following compound.

[0068] [ka]

[0069] Q 2 Examples of compounds (1B) in which (g2-3) is the group include the compound shown in the following formula.

[0070] [ka]

[0071] Q 2 Examples of compounds (1B) in which (g2-4) is the base are the compounds shown in the following formula.

[0072] [ka]

[0073] Q 2 Examples of compounds (1B) in which (g2-7) is the base are the compounds shown in the following formula.

[0074] [ka]

[0075] (Method for producing compound (1A) and compound (1B)) Compound (1A) can be produced, for example, by hydrosilylation of compound (2A) with compound (3a) or compound (3b). Compound (1B) can be produced, for example, by hydrosilylation of compound (2B) with compound (3a) or compound (3b). [(R f -A-)2N-] a1 Q 10 [-CH=CH2] b1 ...(2A) [CH2=CH-] b2 [(R f -A-)2N-] a2 Q 20 -N(-AR f )-AQ f -AN(-AR f )-Q 20 [-N(-AR f )2] a2 [-CH=CH2] b2 ...(2B) However, in equation (2A), Q 10 is an organic group with a1+b1 valency, Q 10 The signs other than are the same as the signs in equation (1A). In equation (2B), Q 20 This is an a² + b² + 1-valent organic group, and has two Q 20 Q can be the same or different, 20 The signs other than those shown are the same as the signs in equation (1B). Q 10 [-CH=CH2] b1 Q in compound (1A) after hydrosilylation. 1 This is the result. Q 10 Q 1 Similar groups can be cited, and the preferred forms are also similar. Q 20 [-CH=CH2] b2 Q in compound (1B) after hydrosilylation. 2 This is the result. Q 20 Q 2 Similar groups can be cited, and the preferred forms are also similar.

[0076] In the above compound (2B), Q f The two monovalent groups linked via may be the same or different. That is, the [CH2=CH-] group of compound (2B) b2 [(R f -A-)2N-] a2 Q 20 -N(-ARf In two bases represented by )-A-, A and Q 20 , R f At least one of a2 and b2 may be different. As for compound (2B), Q is chosen because it is easy to manufacture compound (2B). f A compound (2B) in which the two monovalent groups linked via are identical is preferred. (See below for Q) f A compound (2B) in which two monovalent groups linked via a nucleotide polymorphism are identical is represented by the following formula (2BX). {[CH2=CH-] b2 [(R f -A-)2N-] a2 Q 20 -N(-AR f )-A-}2Q f ...(2BX)

[0077] HSi(R) 3-c (L) c ...(3a) HSi(R 8 ) 3-k [-(OSi(R 9 )2) p -O-Si(R) 3-c (L) c ] k ...(3b) However, the signs in formulas (3a) and (3b) are the same as the signs in formulas (1) and (g3). Compound (3b) can be produced, for example, by the method described in the specification of Japanese Patent Application No. 2018-085493.

[0078] Q 10 [-CH=CH2] b1 As for ease of producing compound (1A), the following groups are preferred: group (g4-1) (where a1=d1+d3 and b1=d2+d4), group (g4-2) (where a1=e1 and b1=e2), group (g4-3) (where a1=1 and b1=2), group (g4-4) (where a1=h1 and b1=h2), or group (g4-5) (where a1=i1 and b1=i2). Q 20 [-CH=CH2]b2 As for ease of producing compound (1B), the following groups are preferred: group (g4-1) (where a2+1=d1+d3 and b2=d2+d4), group (g4-2) (where a2+1=e1 and b2=e2), group (g4-3) (where a2+1=1 and b2=2), group (g4-4) (where a2+1=h1 and b2=h2), or group (g4-5) (where a2+1=i1 and b2=i2).

[0079] [ka]

[0080] (-Q 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 220 -CH=CH2) e2 ...(g4-2) -Q 13 -N(-Q 230 -CH=CH2)2···(g4-3) (-Q 14 -) h1 Z(-Q 240 -CH=CH2) h2 ...(g4-4) (-Q 15 -) i1 Si(R 3 ) 4-i1-i2 (-Q 250 -CH=CH2) i2 ...(g4-5)

[0081] However, Q 220 This is an alkylene group, an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, a group having -C(O)NH-, -C(O)-, or -O- at the end of the alkylene group that is not connected to Si, or a group having -C(O)NH-, -C(O)-, or -O- between the carbon atoms of an alkylene group having 2 or more carbon atoms and having -C(O)NH-, -C(O)-, or -O- at the end that is not connected to Si, and 2 or more Q 220Q can be the same or different, 230 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 or more Q 230 Q can be the same or different, 240 Q 240 If the atom at Z to which the bond is formed is a carbon atom, then Q 220 Q 240 If the atom at Z to which it is bonded is a nitrogen atom, then Q 230 And Q is 2 or greater. 240 Q can be the same or different, 250 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 or more Q 250 Q can be the same or different, 220 Q 230 Q 240 and Q 250 The signs other than those shown are the same as the signs in equations (g2-1) to (g2-5).

[0082] Q 220 -CH=CH2 is Q in compound (1) after hydrosilylation. 22 This is the result. Q 220 Q 22 Similar groups can be cited, and the preferred forms are also similar. Q 230 -CH=CH2 is Q in compound (1) after hydrosilylation. 23 This is the result. Q 230 Q 23 Similar groups can be cited, and the preferred forms are also similar. Q 240 -CH=CH2 is Q in compound (1) after hydrosilylation. 24 This is the result. Q 240 Q 24 Similar groups can be cited, and the preferred forms are also similar. Q 250 -CH=CH2 is Q in compound (1) after hydrosilylation. 25 This is the result. Q 250Q 25 Similar groups can be cited, and the preferred forms are also similar.

[0083] Q 10 [-CH=CH2] b1 Other forms of the base include base(g4-6) (where a1=d1+d3 and b1=k), base(g4-7) (where a1=e1 and b1=k), base(g4-8) (where a1=1 and b1=k), base(g4-9) (where a1=h1 and b1=k), or base(g4-10) (where a1=i1 and b1=k). Q 20 [-CH=CH2] b2 Other forms of the base include base(g4-6) (where a2+1=d1+d3 and b2=k), base(g4-7) (where a2+1=e1 and b2=k), base(g4-8) (where a2+1=1 and b2=k), base(g4-9) (where a2+1=h1 and b2=k), or base(g4-10) (where a2+1=i1 and b2=k).

[0084] [ka]

[0085] (-Q 12 -) e1 C(R 2 ) 4-e1-e2 (-Q 22 -G 1 ) e2 ...(g4-7) -Q 13 -N(-Q 23 -G 1 )2···(g4-8) (-Q 14 -) h1 Z(-Q 24 -G 1 ) h2 ...(g4-9) (-Q 15 -) i1Si(R 3 ) 4-i1-i2 (-Q 25 -G 1 ) i2 ...(g4-10)

[0086] However, G 1 is the base (g5), Q 10 [-CH=CH2] b1 Or Q 20 [-CH=CH2] b2 2 or more G 1 They may be the same or different, G 1 The signs other than those shown are the same as the signs in equations (g2-1) to (g2-5). -Si(R 8 ) 3-k (-Q 30 -CH=CH2) k ...(g5) However, Q 30 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(O)NH-, -C(O)-, or -O- between the carbon atoms, and has 2 or more Q 30 Q can be the same or different, 30 The signs other than are the same as the signs in equation (g3). Q 30 -CH=CH2 is a group with Q in the (g3) group after hydrosilylation. 3 This is the result. Q 30 Q 3 Similar groups can be listed (however, -(OSi(R 9 )2) p (Excluding -O-), the same applies to preferred forms.

[0087] (Method for producing compound (2A) and compound (2B)) Compound (2A) can be produced, for example, by the following procedure. Compound (4A) and compound (5a) are subjected to an amidation reaction to obtain compound (6A). [H2N-] a1 Q 10 [-CH=CH2] b1 ...(4A) Rf -C(O)-X ···(5a) [R f -C(O)-NH-] a1 Q 10 [-CH=CH2] b1 ...(6A) However, X is a halogen atom, an alkoxy group, or a hydroxyl group, and the signs of all other elements are the same as those in formula (2A).

[0088] Compound (4A) is available as a commercially available compound. Furthermore, compound (4A) can be produced, for example, by the method described in Patent Document 1 or the method described in International Publication No. 2019 / 039186. Compound (5a) can be produced, for example, by the method described in International Publication No. 2009 / 008380, International Publication No. 2013 / 121984, International Publication No. 2013 / 121986, International Publication No. 2015 / 087902, International Publication No. 2017 / 038830, International Publication No. 2017 / 038832, International Publication No. 2018 / 143433, and International Publication No. 2018 / 216630. Q 10 [-CH=CH2] b1 A compound (6A) in which is the group (g4-1) can be produced, for example, by the method described in Patent Document 1 (d1 and d3=1, d2 and d4=2). Q 10 [-CH=CH2] b1 Compound (6A) having (g4-2) as the base is, for example, the method described in Patent Document 1 (e1=2, e2=2), the method described in International Publication No. 2017 / 038830 (e1=1, e2=3), the method described in International Publication No. 2019 / 039226 (e1=1, e2=2, R 2 It can be produced by (= hydrogen atoms or alkyl groups). Q 10 [-CH=CH2] b1 Compound (6A), in which (g4-3) is the base, can be produced, for example, by the method described in International Publication No. 2017 / 038832. Q 10 [-CH=CH2]b1 Compound (6A), in which (g4-4) is the base, can be produced, for example, by the method described in International Publication No. 2019 / 039186. Q 10 [-CH=CH2] b1 Compound (6A), in which the group is (g4-7) to (g4-9), can be produced, for example, by the method described in International Publication No. 2019 / 163282.

[0089] Compound (6A) is reacted with a reducing agent (such as sodium borohydride or lithium aluminum hydride) to obtain compound (7A). [R f -CH2-NH-] a1 Q 10 [-CH=CH2] b1 ...(7A) However, the signs in equation (7A) are the same as the signs in equation (2A).

[0090] Compound (7A) and compound (5a) are subjected to an amidation reaction to obtain compound (2Aa). [(R f -CH2-)(R f -C(O)-)N-] a1 Q 10 [-CH=CH2] b1 ...(2Aa) However, the sign in equation (2Aa) is the same as the sign in equation (2A).

[0091] Compound (2Ab) may be obtained by reacting compound (2Aa) with a reducing agent (such as sodium borohydride or lithium aluminum hydride). [(R f -CH2-)2N-] a1 Q 10 [-CH=CH2] b1 ...(2Ab) However, the sign in equation (2Ab) is the same as the sign in equation (2A).

[0092] Compound (2B) can be produced, for example, by the following procedure when a2 is 1 or greater. Compound (4B) and compound (5a) are subjected to an amidation reaction to obtain compound (6B). [H2N-] a2+1 Q 20 [-CH=CH2] b2 ...(4B) R f -C(O)-X ···(5a) [R f -C(O)-NH-] a2 [H2N-]Q 20 [-CH=CH2] b2 ...(6B) However, X is a halogen atom, an alkoxy group, or a hydroxyl group, and the signs of all other elements are the same as those in formula (2B). Examples of compound (4B) include those similar to compound (4A).

[0093] Compound (6B') is obtained by amidation reaction between compound (6B) and compound (5b). XC(O)-Q f -C(O)-X ···(5b) [CH2=CH-] b2 [R f -C(O)-NH-] a2 Q 20 -NH-C(O)-Q f -C(O)-NH-Q 20 [-NH-C(O)-R f ] a2 [-CH=CH2] b2 ...(6B') However, X is a halogen atom, an alkoxy group, or a hydroxyl group, and the signs of all other elements are the same as those in formula (2B). Compound (5b) can be produced in the same manner as compound (5a).

[0094] Compound (6B') is reacted with a reducing agent (such as sodium borohydride or lithium aluminum hydride) to obtain compound (7B). [CH2=CH-] b2 [R f -CH2-NH-] a2 Q 20-NH-CH2-Q f -CH2-NH-Q 20 [-NH-CH2-R f ] a2 [-CH=CH2] b2 ...(7B) However, the sign in equation (7B) is the same as the sign in equation (2B).

[0095] Compound (7B) and compound (5a) are subjected to an amidation reaction to obtain compound (2Ba). [CH2=CH-] b2 [(R f -CH2-)(R f -C(O)-)N-] a2 Q 20 -N(-C(O)-R f )-CH2-Q f -CH2-N(-C(O)-R f )-Q 20 [-N(-C(O)-R f )(-CH2-R f )] a2 [-CH=CH2] b2 ...(2Ba) However, the signs in equation (2Ba) are the same as the signs in equation (2B).

[0096] Compound (2Bb) may be obtained by reacting compound (2Ba) with a reducing agent (such as sodium borohydride or lithium aluminum hydride). [CH2=CH-] b2 [(R f -CH2-)2N-] a2 Q 20 -N(-CH2-R f )-CH2-Q f -CH2-N(-CH2-R f )-Q 20 [-N(-CH2-R f )2] a2 [-CH=CH2] b2 ...(2Bb) However, the sign in equation (2Bb) is the same as the sign in equation (2B).

[0097] Compound (2B) can be produced, for example, by the following procedure when a2 is 0. Compound (4C) and compound (5b) are subjected to an amidation reaction to obtain compound (6C). H2N-Q 20 [-CH=CH2] b2 ...(4C) XC(O)-Q f -C(O)-X ···(5b) [CH2=CH-] b2 Q 20 -NH-C(O)-Q f -C(O)-NH-Q 20 [-CH=CH2] b2 ...(6C) However, X is a halogen atom, an alkoxy group, or a hydroxyl group, and the signs of all other elements are the same as those in formula (2B).

[0098] Compound (6C) is reacted with a reducing agent (such as sodium borohydride or lithium aluminum hydride) to obtain compound (7C). [CH2=CH-] b2 Q 20 -NH-CH2-Q f -CH2-NH-Q 20 [-CH=CH2] b2 ...(7C)

[0099] Compound (7C) and compound (5a) are subjected to an amidation reaction to obtain compound (2Bc). [CH2=CH-] b2 Q 20 -N(-C(O)-R f )-CH2-Q f -CH2-N(-C(O)-R f )-Q 20 [-CH=CH2] b2 ...(2Bc) However, the sign in equation (2Bc) is the same as the sign in equation (2B).

[0100] Compound (2Bd) may be obtained by reacting compound (2Bc) with a reducing agent (such as sodium borohydride or lithium aluminum hydride). [CH2=CH-] b2 Q 20 -N(-CH2-R f )-CH2-Q f -CH2-N(-CH2-R f )-Q 20 [-CH=CH2] b2 ...(2Bd) However, the sign in equation (2Bd) is the same as the sign in equation (2B).

[0101] In the compound (1) described above, a surface layer with excellent friction resistance and fingerprint stain removal properties can be formed even when the chain length of the fluorine-containing organic group is shortened, for the following reasons. The fluorine-containing compound described in Patent Document 1 has multiple fluorine-containing organic groups (fluoropolyether chains), but because the distance between the fluorine-containing organic groups is large, the density of fluorine-containing organic groups in the surface layer is low. Therefore, when attempting to improve the slip resistance of the surface layer by shortening the chain length of the fluorine-containing organic groups, the abrasion resistance and fingerprint stain removal properties of the surface layer tend to decrease. On the other hand, (1) of the present invention involves two fluorine-containing organic groups (R) via an A group in a branching by an N atom. f and R f , or R f and Q f Because the fluorine-containing organic groups are bonded together, the two fluorine-containing organic groups are in close proximity. As a result, the distance between the fluorine-containing organic groups is short, and the density of fluorine-containing organic groups in the surface layer is high. Therefore, even when the chain length of the fluorine-containing organic groups is shortened, a surface layer with excellent abrasion resistance and fingerprint stain removal properties can be formed.

[0102] [Fluorine-containing compound-containing composition] The fluorine-containing compound-containing composition of the present invention (hereinafter also referred to as "this composition") comprises one or more of compound (1) and other fluorine-containing compounds.

[0103] Other fluorine-containing compounds include fluorine-containing compounds produced as by-products in the manufacturing process of compound (1) (hereinafter also referred to as "by-product fluorine-containing compounds"), and known fluorine-containing compounds used for the same purposes as compound (1). As for other fluorine-containing compounds, compounds that are less likely to degrade the properties of compound (1) are preferred.

[0104] Examples of by-product fluorine-containing compounds include unreacted compound (2A) or compound (2B), and fluorine-containing compounds in which a portion of the allyl group isomerized to an inner olefin during hydrosilylation in the production of compound (1). Known fluorine-containing compounds include those commercially available as surface treatment agents. When this composition contains known fluorine-containing compounds, new effects such as complementing the properties of compound (1) may be exhibited.

[0105] The content of compound (1) in this 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 particularly preferably 80% by mass or more and less than 100% by mass. The content of other fluorine-containing compounds in this composition is preferably more than 0% by mass and 40% by mass or less, more preferably more than 0% by mass and 30% by mass or less, and particularly preferably more than 0% by mass and 20% by mass or less. The total content of compound (1) and other fluorine-containing compounds is preferably 80 to 100% by mass, and particularly preferably 85 to 100% by mass, of the composition. If the content of compound (1) and the content of other fluorine-containing compounds 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 are further improved.

[0106] This composition may contain components other than compound (1) and other fluorine-containing compounds, to the extent that it does not impair the effects of the present invention. Other components include by-products generated in the manufacturing process of compound (1) or known fluorine-containing compounds (excluding by-product fluorine-containing compounds), unreacted raw materials, and other compounds that are unavoidable in the manufacturing process. Other components include additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reactions of hydrolyzable silyl groups. Examples of acid catalysts include hydrochloric acid, nitric acid, acetic acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid. Examples of basic catalysts include sodium hydroxide, potassium hydroxide, and ammonia. The content of other components is preferably 0 to 9.999% by mass, and particularly preferably 0 to 0.99% by mass, of the composition.

[0107] [Coating liquid] The coating solution of the present invention (hereinafter also referred to as "the coating solution") comprises compound (1) or the composition and a liquid medium. The coating solution may be a solution or a dispersion.

[0108] An organic solvent is preferred as the liquid medium. The organic solvent may be a fluorine-containing organic solvent or a non-fluorine organic solvent, or it may contain both. Examples of fluorine-containing organic solvents include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, and fluoroalcohols. As the fluorinated alkane, compounds with 4 to 8 carbon atoms are preferred. A commercially available example 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). 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. Commercially available examples 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). Examples of fluorinated alkylamines include perfluorotripropylamine and perfluorotributylamine. Examples of fluoroalcohols include 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol. Preferred non-fluorine organic solvents include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms, and examples include hydrocarbons, alcohols, ketones, ethers, and esters. The liquid medium may be a mixed medium obtained by mixing two or more types.

[0109] The content of compound (1) or the composition is preferably 0.001 to 10% by mass, and particularly preferably 0.01 to 1% by mass, of the coating liquid. The liquid medium content of the coating solution is preferably 90 to 99.999% by mass, and particularly preferably 99 to 99.99% by mass.

[0110] [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. The surface layer may be formed on a part of the surface of the substrate or on the entire surface of the substrate. The surface layer may spread as a film on the surface of the substrate or may be scattered as dots. The surface layer contains compound (1) in a state in which some or all of the hydrolyzable silyl groups of compound (1) have undergone hydrolysis and the silanol groups have undergone dehydration condensation.

[0111] The surface layer thickness is preferably 1 to 100 nm, and particularly preferably 1 to 50 nm. If the surface layer thickness is 1 nm or more, the effects of the surface treatment are easily obtained. If the surface layer thickness is 100 nm or less, the utilization efficiency is high. The surface layer thickness can be calculated from the vibration period of the interference pattern obtained by the X-ray reflectivity method using a thin-film analysis X-ray diffractometer (RIGAKU Corporation, ATX-G).

[0112] Examples of substrates include those that require water-repellent and oil-repellent properties. These include substrates that may come into contact with other items (e.g., styluses) or people's fingers during use, substrates that may be held by people's fingers during operation, and substrates that may be placed on other items (e.g., stands). Examples of substrate materials include metals, resins, glass, sapphires, ceramics, stones, and composite materials thereof. The glass may be chemically strengthened. An undercoat, such as an SiO2 film, may be formed on the surface of the substrate. Suitable substrates include touch panel substrates, display substrates, and eyeglass lenses, with touch panel substrates being particularly preferred. Glass or transparent resin are preferred materials for the touch panel substrate. Furthermore, glass or resin films used for the exterior parts (excluding the display) of devices such as mobile phones (e.g., smartphones), personal digital assistants (e.g., tablet devices), game consoles, and remote controls are also preferred as substrates.

[0113] [Method of manufacturing articles] This article can be manufactured, for example, by the following method. A method for treating the surface of a substrate by a dry coating method using compound (1) or the composition, thereby forming a surface layer on the surface of the substrate made from compound (1) or the composition. A method of applying the coating liquid to the surface of a substrate by a wet coating method and drying it to form a surface layer on the surface of the substrate that is made of compound (1) or the composition.

[0114] Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferred as a dry coating method due to its ability to suppress the decomposition of compound (1) and its simplicity of equipment. During vacuum deposition, a pellet-like material impregnated with compound (1) or this composition may be used in a porous metal such as iron or steel. Alternatively, this coating solution may be impregnated into a porous metal such as iron or steel, the liquid medium may be dried, and a pellet-like material impregnated with compound (1) or this composition may be used.

[0115] Wet coating methods include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, cast coating, Langmuir-Bludget coating, and gravure coating. [Examples]

[0116] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. In the following, "%" refers to "mass%" unless otherwise specified. Examples 1-4 and 9-12 are examples, and Examples 5-8 and 13-16 are comparative examples.

[0117] [Example 1] (Example 1-1) 5.51 g of adiponitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 500 mL of tetrahydrofuran (hereinafter also referred to as "THF") were added to a 1000 mL four-necked flask and stirred while cooling in a dry ice-acetone bath under a nitrogen atmosphere. Then, 50 mL of hexane solution of lithium diisopropylamide (1.1 mol / L, manufactured by Aldrich) was slowly added, followed by the slow addition of 7.5 g of allyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.). This procedure was repeated four times, adding a total of 200 mL of hexane solution of lithium diisopropylamide and a total of 29.9 g of allyl bromide. The contents of the flask were stirred for 12 hours while slowly returning to 25°C. Then, 300 mL of 1N hydrochloric acid aqueous solution was added, and liquid-liquid separation was performed using methylene chloride. The resulting organic layer was dried over magnesium sulfate, the solid was removed by filtration, and the liquid was concentrated. The obtained crude material was purified by silica gel column chromatography to obtain 5.47 g of compound (8-1). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 5.9~5.7 (4H), 5.4~5.1 (8H), 2.3 (8H), 1.7 (4H).

[0118] [ka]

[0119] (Examples 1-2) 5.47 g of compound (8-1) obtained in Example 1-1 and 500 mL of THF were added to a 1000 mL four-necked flask, and the mixture was stirred in an ice bath under a nitrogen atmosphere. Then, a THF solution of lithium aluminum hydride (2.5 mol / L, manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added. The contents of the flask were stirred for 14 hours while slowly returning to 25°C. Then, 2 mL of deionized water and 2 mL of 15% sodium hydroxide aqueous solution were added and stirred, and a further 6 mL of deionized water was added and stirred. The precipitated solid was removed by Celite filtration to obtain 5.64 g of crude compound (4-1).

[0120] [ka]

[0121] (Examples 1-3) Compound (5-1) was obtained according to the method described in Example 1 of International Publication No. 2008 / 026707, and compound (5-2) was obtained by reacting compound (5-1) with methanol. CF3CF2OCF2CF2OCF2C(O)F ···(5-1) CF3CF2OCF2CF2OCF2C(O)OCH3...(5-2) 16.36 g of compound (5-2) was added to the crude compound (4-1) obtained in Example 1-2, and the mixture was stirred at 25°C for 3 hours. The reaction product was then concentrated and purified by silica gel column chromatography to obtain 9.24 g of compound (6-1). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 6.9 (2H), 5.9~5.7 (4H), 5.2~5.0 (8H), 3.2 (4H), 2.0 (8H), 1.3 (4H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -79 (4F), -87 (6F), -88~-89 (12F).

[0122] [ka]

[0123] (Examples 1-4) 5.04 g of compound (6-1) obtained in Example 1-3 and 100 mL of THF were added to a 200 mL round-bottom flask and stirred at 25°C. Then, 7 mL of lithium aluminum hydride THF solution (2.5 mol / L) was slowly added dropwise, and the mixture was stirred under reflux for 13 hours. After that, the reaction system was cooled in an ice bath, and 0.6 mL of deionized water and 1.8 mL of 15% sodium hydroxide aqueous solution were added and stirred, followed by the addition of another 1.8 mL of deionized water and stirring. The precipitated solid was removed by Celite filtration, and the solvent was removed by distillation. The resulting crude product was purified by silica gel column chromatography to obtain 2.4 g of compound (7-1). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 5.9~5.7 (4H), 5.2~5.0 (8H), 3.2 (4H), 2.5 (4H), 2.0 (8H), 1.3 (4H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -76 (4F), -87 (6F), -88~-89 (12F).

[0124] [ka]

[0125] (Examples 1-5) Under a nitrogen atmosphere, 0.62 g of compound (7-1) obtained in Example 1-4, 1.28 g of triethylamine, and 13 mL of methylene chloride were added to a 20 mL vial and stirred at 25°C. Then, 1.04 g of compound (5-1) obtained in Example 1-3 was added and stirred at 25°C for 2 hours, after which another 0.37 g of compound (5-1) was added and stirred for 12 hours. The mixture was extracted with 1N hydrochloric acid aqueous solution, the resulting organic layer was dried over magnesium sulfate, and then concentrated. Subsequently, it was purified by silica gel column chromatography to obtain 1.00 g of compound (2a-1). 1¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 5.9~5.7 (4H), 5.2~5.0 (8H), 4.1 (4H), 3.5 (4H), 2.0 (8H), 1.3 (4H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -70~-73(8F), -87(12F), -88~-89(24F).

[0126] [ka]

[0127] (Examples 1-6) Under a nitrogen atmosphere, 3.5 mg of aniline, 5.2 mg of platinum(0)-1,3-divinyltetramethyldisiloxane complex, and 10 g of 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane (AGC, AC-6000) were mixed to prepare a catalyst solution. Under a nitrogen atmosphere, 0.51 g of compound (2a-1) obtained in Example 1-5, 0.18 g of trimethoxysilane, and 0.52 g of the catalyst solution were added to a 5 mL vial and stirred at 40°C for 3 days. The solvent was then removed by distillation to obtain 0.58 g of compound (1-1).

[0128] [ka]

[0129] 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 4.1 (4H), 3.6-3.4 (40H), 1.5-1.0 (20H), 0.5 (8H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -70~-73(8F), -87(12F), -88~-89(24F).

[0130] [Example 2] (Example 2-1) Compound (4-2)(2,2-diallylpropane-1,3-diamine) was obtained using the same method as in Examples 1-1 and 1-2, except that the starting material in Example 1-1 was changed from adiponitrile to malononitrile. Under a nitrogen atmosphere, 13.8 g of compound (5-2) obtained in Example 1-3 was added to a 50 mL three-necked flask and stirred in an ice bath. Then, 2.46 g of compound (4-2) was added over 2 hours and stirred for 3 hours. The crude product was purified by silica gel column chromatography to obtain 12.3 g of compound (6-2). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 5.93~5.84 (2H,m), 5.22~5.12 (4H,m), 3.20 (4H,d,J=6.9Hz), 2.03 (4H,d,J=7.3Hz). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ(ppm): -78.50 (4F,t,J=12.0Hz), -87.00(6F,s), -88.69(4F,t,J=12.0Hz), -88.82(8F,s).

[0131] [ka]

[0132] (Example 2-2) 9.18 g of compound (6-2) obtained in Example 2-1 and 1000 mL of THF were added to a 1000 mL round-bottom flask and stirred at 25°C. Then, 30 mL of lithium aluminum hydride THF solution (2.5 mol / L) was slowly added dropwise, and the mixture was stirred under reflux for 16 hours. After that, the reaction system was cooled in an ice bath, and sodium sulfate decahydrate was added while stirring until the foaming stopped. The precipitated solid was removed by Celite filtration, and the solvent was removed by distillation. The resulting crude product was purified by silica gel column chromatography to obtain 7.38 g of compound (7-2). 1H-NMR (300.4MHz, Solvent: CDCl3, Standard: Tetramethylsilane) δ(ppm): 5.86~5.72(2H,m), 5.09~5.03(4H,m), 3.15(4H,t,J=10.5 Hz), 2.58(4H,s), 2.03(4H,d,J=7.5Hz), 1.49(2H,s). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ(ppm): -75.67~-75.84(4F,m), -87.03(6F,s), -88.87~-89.04(8F,m), -89.16~-89.22(4F,m).

[0133] [ka]

[0134] (Examples 2-3) Under a nitrogen atmosphere, 1.10 g of compound (7-2) obtained in Example 2-2, 2.89 g of triethylamine, and 25 mL of methylene chloride were added to a 50 mL three-necked flask and stirred at 25°C. Then, 2.30 g of compound (5-1) obtained in Example 1-3 was added and stirred at 25°C for 2 hours, after which 1.52 g of compound (5-1) was added and stirred for 3 hours. Then, 1.65 g of compound (5-1) was added and stirred for 21 hours. 60 mL of 1 N hydrochloric acid aqueous solution was added and extracted three times using 50 mL of methylene chloride. The resulting organic layer was dried over magnesium sulfate and then concentrated. Subsequently, it was purified by silica gel column chromatography to obtain 0.61 g of compound (2a-2). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 5.87~5.73 (2H,m), 5.25~5.08 (4H,m), 4.12 (4H,t,J=8.8Hz), 3.56 (4H,s), 2.07 (4H,d,J=6.9Hz). 19F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ(ppm): -71.09(4F,s), -71.82(4F,s), -87.50(6F,s), -87.53(6F,s), -88.84~-89.72(24F,m).

[0135] [ka]

[0136] (Examples 2-4) Under a nitrogen atmosphere, 0.56 g of compound (2a-2) obtained in Example 2-3, 0.12 g of trimethoxysilane, 1.9 mg of aniline, 5.2 mg of platinum(0)-1,3-divinyltetramethyldisiloxane complex, and 0.63 g of AC-6000 were added to a 5 mL vial and stirred at 40°C for 3 hours. The solvent was then removed by distillation to obtain 0.65 g of compound (1-2). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 4.11 (4H,t,J=8.9 Hz), 3.51 (18H,s), 3.51 (4H,s), 1.38 (4H,t,J=6.0 Hz), 1.26 (4H,t,J=7.6 Hz), 0.54 (4H,t,J=7.2 Hz). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ(ppm): -71.09(4F,s), -71.82(4F,s), -87.50(6F,s), -87.53(6F,s), -88.84~-89.72(24F,m).

[0137] [ka]

[0138] [Example 3] (Example 3-1) Compound (4-3) was obtained using the same method as in Examples 1-1 and 1-2, except that the starting material in Example 1-1 was changed from adiponitrile to acetonitrile. Under a nitrogen atmosphere, 2.45 g of compound (5-2) obtained in Example 1-3 was added to a 50 mL three-necked flask and stirred in an ice bath. Then, 1.04 g of compound (4-3) was added and stirred for 7 hours. The crude product was purified by silica gel column chromatography to obtain 2.89 g of compound (6-3). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 6.5 (1H), 6.0-5.7 (3H), 5.2-5.0 (6H), 3.3 (2H), 2.0 (6H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -76 (2F), -87 (3F), -89 (6F).

[0139] [ka]

[0140] (Example 3-2) 2.0 g of compound (6-3) obtained in Example 3-1 and 200 mL of THF were added to a 300 mL round-bottom flask and stirred at 25°C. Then, 10 mL of lithium aluminum hydride THF solution (2.5 mol / L) was slowly added dropwise, and the mixture was stirred under reflux for 16 hours. After that, the reaction system was cooled in an ice bath, and sodium sulfate decahydrate was added while stirring until the foaming stopped. The precipitated solid was removed by Celite filtration, and the solvent was removed by distillation. The resulting crude product was purified by silica gel column chromatography to obtain 0.92 g of compound (7-3). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 6.0~5.7 (3H), 5.2~5.0 (6H), 3.1 (2H), 2.5 (2H), 2.0 (6H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -76 (2F), -87 (3F), -88~-89 (6F).

[0141] [ka]

[0142] (Example 3-3) Under a nitrogen atmosphere, 0.92 g of compound (7-3) obtained in Example 3-2, 3 mL of triethylamine, and 21 mL of methylene chloride were added to a 50 mL three-necked flask and stirred at 25°C. Then, 1.81 g of compound (5-1) obtained in Example 1-3 was added and stirred at 25°C for 2 hours. Subsequently, another 1.54 g of compound (5-1) was added and stirred for 2 hours. The mixture was extracted with 1 N hydrochloric acid aqueous solution, and the resulting organic layer was dried over magnesium sulfate and then concentrated. The mixture was then purified by silica gel column chromatography to obtain 1.42 g of compound (2a-3). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 5.9~5.7 (3H), 5.2~5.0 (6H), 4.1 (2H), 3.5 (2H), 2.0 (6H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -72~-76(4F), -89(6F), -92(12F).

[0143] [ka]

[0144] (Example 3-4) Under a nitrogen atmosphere, 0.55 g of compound (2a-3) obtained in Example 3-3, 0.36 g of trimethoxysilane, 1.9 mg of aniline, 3.2 mg of platinum(0)-1,3-divinyltetramethyldisiloxane complex, and 0.55 g of AC-6000 were added to a 5 mL vial and stirred at 40°C for 3 hours. The solvent was then removed by distillation to obtain 0.77 g of compound (1-3). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 4.1 (2H), 3.7 (27H), 3.2 (2H), 1.4 (6H), 1.2 (6H), 1.5 (6H). 19F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -72~-76(4F), -89(6F), -92(12F).

[0145] [ka]

[0146] [Example 4] Compound (5-3) was obtained according to the method described in Example 1 of International Publication No. 2009 / 008380. The mean value of x was 7. Compound (5-4) was obtained according to the method described in Example 1 of International Publication No. 2009 / 008380. The mean value of x was 7. CF3(OCF2CF2) x OCF2C(O)F ···(5-3) CF3(OCF2CF2) x OCF2C(O)OCH2CH3···(5-4) Compound (1-4) was obtained in the same manner as in Examples 1-3 to 1-6, except that compound (5-4) was used instead of compound (5-2) and compound (5-3) was used instead of compound (5-1). The mean value of x is 7. R f The average molecular weight is 1000.

[0147] [ka]

[0148] [Example 5] Under a nitrogen atmosphere, 1.05 g of compound (6-1) obtained in Example 1-3, 0.62 g of trimethoxysilane, 2.8 mg of aniline, 2.8 mg of platinum(0)-1,3-divinyltetramethyldisiloxane complex, and 1.06 g of AC-6000 were added to a 20 mL vial and stirred at 40°C for 5 hours. The reaction mixture was then concentrated to obtain 1.6 g of compound (10-1). 1¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 7.5 (2H), 3.5 (36H), 3.1 (4H), 1.5~0.9 (20H), 0.5 (8H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -79 (4F), -87 (6F), -88~-89 (12F).

[0149] [ka]

[0150] [Example 6] Under a nitrogen atmosphere, 0.50 g of compound (6-2) obtained in Example 2-1, 0.28 g of trimethoxysilane, 1.2 mg of aniline, 5.8 mg of platinum(0)-1,3-divinyltetramethyldisiloxane complex, and 0.55 g of AC-6000 were added to a 5 mL vial and stirred at 40°C for 3 hours. The solvent was then removed by distillation to obtain 0.64 g of compound (10-2). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 3.6 (18H), 3.2 (4H,s), 1.4 (4H), 1.2 (4H), 0.5 (4H). 19 F-NMR (282.7 MHz, solvent: CDCl3, reference: C6F6) δ (ppm): -78 (4F), -87 (6F), -88 (4F), -88 (8F).

[0151] [ka]

[0152] [Example 7] Under a nitrogen atmosphere, 0.60 g of compound (6-3) obtained in Example 3-1, 0.49 g of trimethoxysilane, 2.2 mg of aniline, 5.2 mg of platinum(0)-1,3-divinyltetramethyldisiloxane complex, and 0.55 g of AC-6000 were added to a 5 mL vial and stirred at 40°C for 3 hours. The solvent was then removed by distillation to obtain 1.01 g of compound (10-3). 1 ¹H-NMR (300.4 MHz, solvent: CDCl3, reference: tetramethylsilane) δ (ppm): 3.7 (27H), 3.2 (2H), 1.4 (6H), 1.2 (6H), 1.5 (6H). 19 F-NMR (282.7MHz, solvent: CDCl3, standard: C6F6) δ (ppm): -76 (2F), -87 (3F), -89 (6F).

[0153] [ka]

[0154] [Example 8] Compound (10-4) was obtained in the same manner as in Examples 1-3 and 5, except that compound (5-4) obtained in Example 4 was used instead of compound (5-2). The average value of x was 7.

[0155] [ka]

[0156] [Examples 9-16: Manufacturing and evaluation of goods] The substrates were surface-treated using the compounds obtained in Examples 1-8 to obtain the articles of Examples 9-16. For each example, the following dry coating and wet coating methods were used as surface treatment methods. Chemically strengthened glass was used as the substrate. The obtained articles were evaluated using the following methods. The results are shown in Table 1.

[0157] (Dry coating method) Dry coating was performed using a vacuum deposition apparatus (ULVAC, VTR350M) (vacuum deposition method). 0.5 g of each compound obtained in Examples 1-8 was packed into a molybdenum boat in the vacuum deposition apparatus, and the inside of the vacuum deposition apparatus was filled to 1 × 10⁻⁶ -3 The air was evacuated to below Pa. The boat containing the compound was heated at a rate of 10°C / min or less, and when the deposition rate measured by a quartz crystal film thickness gauge exceeded 1 nm / second, the shutter was opened to begin film formation on the substrate surface. When the film thickness reached approximately 50 nm, the shutter was closed to end film formation on the substrate surface. The substrate on which the compound was deposited was heat-treated at 200°C for 30 minutes and washed with dichloropentafluoropropane (AGC, AK-225) to obtain an article with a surface layer on the substrate surface.

[0158] (Wet coating method) Each compound obtained in Examples 1-8 was mixed with C4F9OC2H5 (3M, Novec® 7200) 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 having a surface layer on the surface of the substrate.

[0159] (Evaluation method) <Method for measuring the water contact angle> The contact angle of approximately 2 μL of distilled water 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.

[0160] <Initial water contact angle> The initial water contact angle of the surface layer was measured using the measurement method described above. The evaluation criteria are as follows. ○ (Good): 100 degrees or higher. × (Not allowed): Below 100 degrees.

[0161] <Slip resistance> A fully automatic contact angle meter (DMo-701, manufactured by Kyowa Interface Science Co., Ltd.) with its main surface held horizontally was prepared. An object was placed on the surface (horizontal plane) of a polyethylene sheet (Hagitec Co., Ltd., rigid polyethylene sheet (high-density polyethylene)) so that the surface layer was in contact with it. The fully automatic contact angle meter was then used to gradually tilt the sheet, and the angle between the surface layer of the object and the horizontal plane (sliding angle) at which the object began to slide was measured. The judgment criteria are shown below. The measurement was performed under the following conditions: contact area between the object and the polyethylene sheet: 6 cm × 6 cm, and load on the object: 0.98 N. ◎(Excellent): The angle of descent is 5 degrees or more. ○ (Good): The angle of descent is 2 degrees or more and less than 5 degrees. × (Not acceptable): The angle of fall is less than 2 degrees.

[0162] <Abrasion resistance> 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). A cellulose nonwoven fabric (manufactured by Asahi Kasei Corporation, Bencot® M-3) was subjected to a load of 9.8 N and a speed of 320 cm / min for 10,000 reciprocating cycles, after which the water contact angle was measured. The smaller the decrease in water repellency (water contact angle) after friction, the smaller the performance degradation due to friction and the superior abrasion resistance. The evaluation criteria are as follows. ◎(Excellent): The change in water contact angle after 10,000 cycles is 10 degrees or less. ○ (Good): The change in water contact angle after 10,000 cycles is between 10 degrees and 15 degrees. × (Not acceptable): The change in water contact angle after 10,000 round trips exceeds 15 degrees.

[0163] <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.

[0164] [Table 1]

[0165] Examples 9-12 using compound (1A) were confirmed to exhibit excellent initial water and oil repellency, abrasion resistance, fingerprint stain removal, and slip resistance. [Industrial applicability]

[0166] The fluorine-containing compound of the present invention can be used in various applications where lubrication and water / oil repellency are required. For example, it can be used in display input devices such as touch panels, surface protective coatings for transparent glass or transparent plastic components, anti-fouling coatings for kitchens, water-repellent and moisture-proof coatings and anti-fouling coatings for electronic devices, heat exchangers, batteries, etc., anti-fouling coatings for toiletries, coatings for components that require both conductivity and liquid repellency, water-repellent, waterproof and water-slip coatings for heat exchangers, and low-friction surface coatings for vibrating screens and the inside of cylinders. More specific examples of use include front protective plates, anti-reflective plates, polarizing plates, anti-glare plates for displays, or those with anti-reflective coatings applied to their surfaces; touch panel sheets and touch panel displays for mobile phones and other devices with display input devices that allow users to operate the screen with their fingers or palms; decorative building materials for wet areas such as toilets, bathrooms, washrooms, and kitchens; waterproof coatings for wiring boards; water-repellent and waterproof coatings for heat exchangers; water-repellent coatings for solar cells; waterproof and water-repellent coatings for printed circuit boards; waterproof and water-repellent coatings for electronic equipment casings and electronic components; insulation-enhancing coatings for power transmission lines; waterproof and water-repellent coatings for various filters; waterproof coatings for radio wave absorbing materials and sound-absorbing materials; anti-fouling coatings for baths, kitchen equipment, and toiletries; water-repellent, waterproof, and water-slip coatings for heat exchangers; low-friction surface coatings for vibrating screens and cylinder interiors; and surface protection coatings for machine parts, vacuum equipment parts, bearing parts, automobile parts, tools, etc. Furthermore, the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2018-222871, filed on November 28, 2018, are incorporated herein by reference as disclosure of the present invention.

Claims

1. A fluorine-containing compound, represented by the formula (1A) below. [(R ｆ -A-) ２ N-] ａ１ Q １ [-T] ｂ１ ・・・(1A) however, R ｆ R is a fluoroalkyl group (where at least one fluorine atom is bonded to the carbon atom at the A terminal), or a group having -O- between carbon atoms of a fluoroalkyl group having 2 or more carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A terminal), and 2 or more R in formula (1A) ｆ They may be the same or different. A is a divalent organic group that does not contain a fluorine atom, and the two or more A's in formula (1A) may be the same or different. However, (R ｆ -A-) ２ Of the two As constituting N, one is -(CH ２ ) ｎ -(where n is an integer of 1 to 10), and the other is -C(O)-, Q １ This is an organic group with a1+b1 valency, T is -Si(R) ３－ｃ (L) ｃ And, R is an alkyl group, L is a hydrolyzable group or a hydroxyl group, and two or more Ls may be the same or different. a1 is an integer greater than or equal to 1, and is greater than or equal to 2 [(R ｆ -A-) ２ N-] may be the same or different. b1 is an integer greater than or equal to 2, and T, which is greater than or equal to 2, may be the same or different. c is 2 or 3, The aforementioned Q １ However, these are the groups represented by formula (g2-1) (where a1 = d1 + d3 and b1 = d2 + d4), the groups represented by formula (g2-2) (where a1 = e1 and b1 = e2), the groups represented by formula (g2-3) (where a1 = 1 and b1 = 2), the groups represented by formula (g2-4) (where a1 = h1 and b1 = h2), or the groups represented by formula (g2-5) (where a1 = i1 and b1 = i2). 【Chemistry 1】 (-Q １２ -) ｅ１ C(R ２ ) ４－ｅ１－ｅ２ (-Q ２２ -) ｅ２ ・・・(g2-2) -Q １３ -N(-Q ２３ -) ２ ・・・(g2-3) (-Q １４ -) ｈ１ Z(-Q ２４ -) ｈ２ ・・・(g2-4) (-Q １５ -) ｉ１ Si(R ３ ) ４－ｉ１－ｉ２ (-Q ２５ -) ｉ２ ・・・(g2-5) however, In equations (g2-1) to (g2-5), Q １２ Q １３ Q １４ and Q １５ The side is [(R ｆ -A-) ２ Connect to the nitrogen atom of [N-], Q ２２ Q ２３ Q ２４ and Q ２５ The side is connected to T, Q １１ This refers to a single bond, an -O-, an alkylene group, or an alkylene group having -O- between carbon atoms of two or more carbon atoms. Q １２ Q is a single bond, -C(O)-, or an alkylene group. １ Q １２ If you have two or more Q １２ They may be the same or different. Q １３ It is an alkylene group, Q １４ Q １４ If the atom at Z to which it is bonded is a carbon atom, then Q １２ Q １４ If the atom at Z to which the bond is formed is a nitrogen atom, then Q １３ Q １ Q １４ If you have two or more Q １４ They may be the same or different. Q １５ Q is an alkylene group, １ Q １５ If you have two or more Q １５ They may be the same or different. Q ２２ is an alkylene group having 2 or more carbon atoms, and 2 or more Q ２２ They may be the same or different. Q ２３ This is an alkylene group having 2 or more carbon atoms, and has two Q ２３ They may be the same or different. Q ２４ Q ２４ If the atom at Z to which it is bonded is a carbon atom, then Q ２２ Q ２４ If the atom at Z to which the bond is formed is a nitrogen atom, then Q ２３ And Q is 2 or more. ２４ They may be the same or different. Q ２５ is an alkylene group having 2 or more carbon atoms, and 2 or more Q ２５ They may be the same or different. Z is Q １４ It has a carbon or nitrogen atom that is directly bonded to it and Q ２４ It is a group having an a1+b1 valent ring structure with a carbon or nitrogen atom to which it is directly bonded, R １ Q is a hydrogen atom or an alkyl group, １ R １ If there are two or more, then there are two or more R １ They may be the same or different. R ２ is a hydrogen atom or an alkyl group, R ３ is an alkyl group, d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1 + d3 is an integer between 1 and 4, and d2 + d4 is an integer between 2 and 5. e1 is 1 or 2, e2 is 2 or 3, and e1 + e2 is 3 or 4. h1 is an integer greater than or equal to 1, and h2 is an integer greater than or equal to 2. i1 is either 1 or 2, i2 is either 2 or 3, and i1 + i2 is either 3 or 4.

2. The aforementioned R ｆ The fluorine-containing compound according to claim 1, wherein the group is represented by the following formula (g1a). R ｆ１ -(OR ｆ２ ) ｍ - ・・・(g1a) however, R ｆ１ This is a fluoroalkyl group having 1 to 6 carbon atoms (wherein m is 0, at least one fluorine atom is bonded to the terminal carbon atom on the A side). R ｆ２ is a fluoroalkylene group having 1 to 6 carbon atoms (however, at least one fluorine atom is bonded to the carbon atom at the terminal on the A side of R ｆ２ bonded to A).), and m is a non-negative integer, and if m is 2 or greater, (OR ｆ２ ) ｍ is two or more OR ｆ２ It may consist of the following:

3. The aforementioned R ｆ The fluorine-containing compound according to claim 1 or 2, wherein the molecular weight is 50 to 1000.

4. A fluorine-containing compound-containing composition characterized by comprising one or more fluorine-containing compounds described in any one of claims 1 to 3, and other fluorine-containing compounds.

5. A fluorine-containing compound according to any one of claims 1 to 3 or a fluorine-containing compound-containing composition according to claim 4, A coating liquid characterized by containing a liquid medium.

6. An article characterized by having a surface layer formed from a fluorine-containing compound according to any one of claims 1 to 3 or a fluorine-containing compound-containing composition according to claim 4 on the surface of a substrate.

7. The article according to claim 6, 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.

8. A method for manufacturing an article, characterized by treating the surface of a substrate by a dry coating method using a fluorine-containing compound according to any one of claims 1 to 3 or a fluorine-containing compound-containing composition according to claim 4, thereby forming a surface layer on the surface of the substrate made of the fluorine-containing compound or the fluorine-containing compound-containing composition.

9. A method for manufacturing an article, characterized by applying the coating liquid described in claim 5 to the surface of a substrate by a wet coating method and drying it to form a surface layer on the surface of the substrate that is made of the fluorine-containing compound or the fluorine-containing compound-containing composition.

10. A fluorine-containing compound, represented by the formula (2A) below. [(R ｆ -A-) ２ N-] ａ１ Q １０ [-CH=CH ２ ] ｂ１ ・・・(2A) however, R ｆ R is a fluoroalkyl group (where at least one fluorine atom is bonded to the carbon atom at the A terminal), or a group of a fluoroalkyl group having 2 or more carbon atoms with -O- between the carbon atoms (where at least one fluorine atom is bonded to the carbon atom at the A terminal), and 2 or more R in formula (2A) ｆ They may be the same or different. A is a divalent organic group that does not contain a fluorine atom, and the two or more A's in formula (2A) may be the same or different. However, (R ｆ -A-) ２ One of the two A's that make up N is -(CH ２ ) ｎ - (where n is an integer from 1 to 10), and the other is -C(O)-, Q １０ This is an organic group with a1+b1 valency, a1 is an integer greater than or equal to 1, and is greater than or equal to 2 [(R ｆ -A-) ２ N-] may be the same or different. b1 is an integer greater than or equal to 2, The aforementioned Q １０ [-CH=CH ２ ] ｂ１ However, the base is (g4-1) (where a1 = d1 + d3 and b1 = d2 + d4), base (g4-2) (where a1 = e1 and b1 = e2), base (g4-3) (where a1 = 1 and b1 = 2), base (g4-4) (where a1 = h1 and b1 = h2), or base (g4-5) (where a1 = i1 and b1 = i2). 【Chemistry 2】 (-Q １２ -) ｅ１ C(R ２ ) ４－ｅ１－ｅ２ (-Q ２２０ -CH=CH ２ ) ｅ２ ・・・(g4-2) -Q １３ -N(-Q ２３０ -CH=CH ２ ) ２ ・・・(g4-3) (-Q １４ -) ｈ１ Z(-Q ２４０ -CH=CH ２ ) ｈ２ ・・・(g4-4) (-Q) １５ -) ｉ１ Si(R ３ ) ４－ｉ１－ｉ２ (-Q) ２５０ -EH=EH ２ ) ｉ２ ・・・('4-5) however, Q １１ This refers to a single bond, an -O-, an alkylene group, or an alkylene group having -O- between carbon atoms of two or more carbon atoms. Q １２ Q is a single bond, -C(O)-, or an alkylene group. １０ Q １２ If you have two or more Q １２ They may be the same or different. Q １３ It is an alkylene group, Q １４ Q １４ If the atom at Z to which it is bonded is a carbon atom, then Q １２ Q １４ If the atom at Z to which the bond is formed is a nitrogen atom, then Q １３ Q １０ Q １４ If you have two or more Q １４ They may be the same or different. Q １５ Q is an alkylene group, １０ Q １５ If you have two or more Q １５ They may be the same or different. Q ２２０ is an alkylene group, and 2 or more Q ２２０ They may be the same or different. Q ２３０ is an alkylene group, and 2 or more Q ２３０ They may be the same or different. Q ２４０ Q ２４０ If the atom at Z to which it is bonded is a carbon atom, then Q ２２０ Q ２４０ If the atom at Z to which the bond is formed is a nitrogen atom, then Q ２３０ And Q is 2 or more. ２４０ They may be the same or different. Q ２５０ is an alkylene group, and 2 or more Q ２５０ They may be the same or different. Z is Q １４ Q240 is a group having an a1+b1 valent ring structure with a carbon or nitrogen atom to which it is directly bonded, R １ Q is a hydrogen atom or an alkyl group, １０ R １ If there are two or more, then there are two or more R １ They may be the same or different. R ２ is a hydrogen atom or an alkyl group, R ３ is an alkyl group, d1 is an integer between 0 and 3, d2 is an integer between 0 and 3, and d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, d4 is an integer between 0 and 3, and d3 + d4 is an integer between 1 and 3. d1 + d3 is an integer between 1 and 4, and d2 + d4 is an integer between 2 and 5. e1 is 1 or 2, e2 is 2 or 3, and e1 + e2 is 3 or 4. h1 is an integer greater than or equal to 1, and h2 is an integer greater than or equal to 2. i1 is either 1 or 2, i2 is either 2 or 3, and i1 + i2 is either 3 or 4.

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