Fluorine atom-containing silane compound

Abstract

A fluorine atom-containing silane compound represented by formula (1), wherein the meaning of each symbol is the same as that described in the description. (Rf1) [alpha] 1-XA-(RSi) [alpha] 2... (1)

Description

Technical Field

[0001] The present invention relates to a fluorine atom-containing silane compound. Background Art

[0002] When certain types of silane compounds are used for surface treatment of a substrate, they can provide excellent water and oil repellency (Patent Document 1).

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2019-44179 Summary of the Invention

[0006] Technical Problem to be Solved by the Invention

[0007] An object of the present invention is to provide a fluorine atom-containing silane compound (fluorine atom-containing silane compound) as a novel compound.

[0008] Technical Means for Solving the Technical Problem

[0009] The present invention provides the following [1] to

[23] .

[0010] [1] A fluorine atom-containing silane compound represented by the following formula (1).

[0011] (Rf 1 ) α1 -X A -(R Si )α 2 …(1)

[0012] [In the formula:

[0013] Rf 1 Each independently has at least one group selected from a monovalent organic group having A 1 γ11 A 2 γ12 C-, and a monovalent organic group including a cyclic structure containing CF≡;

[0014] A 1 is a fluorine atom;

[0015] A 2 Each independently is a hydrogen atom, a chlorine atom or a bromine atom;

[0016] γ11 are each independently 1 or 2;

[0017] γ12 are each independently 1 or 2;

[0018] The sum of γ11 and γ12 is 3;

[0019] X A is independently a single bond, an oxygen atom or a divalent to decavalent organic group;

[0020] R Si is a monovalent group containing a Si atom bonded with a hydroxyl group or a hydrolyzable group;

[0021] α1 is an integer from 1 to 9; and

[0022] α2 is an integer from 1 to 9.

[0023] [2] The fluorine atom-containing silane compound as described in [1], wherein Rf 1 is A 1 γ11 A 2 γ12 C-X B -represented group.

[0024] [In the formula:

[0025] A 1 is a fluorine atom;

[0026] A 2 are independently a hydrogen atom, a chlorine atom or a bromine atom;

[0027] γ11 are independently 1 or 2;

[0028] γ12 are independently 1 or 2;

[0029] The sum of γ11 and γ12 is 3;

[0030] X B is a single bond, a divalent polysiloxane-containing group or -(CR A1 e1 H 2－e1 ) a1 -(CFH) b1 -(CH 2 ) c1 -(O) d1 -represented group.

[0031] (In the formula,

[0032] R A1 is a monovalent organic group having A 1 γ11 A 2 γ12 C-;

[0033] e1 is 1 or 2;

[0034] a1 is an integer from 0 to 200;

[0035] b1 is an integer from 0 to 200;

[0036] c1 is an integer from 0 to 200;

[0037] d1 is an integer from 0 to 200; and

[0038] The order of existence of each repeating unit with the labeling symbols a1, b1, c1, and d1 enclosed in parentheses is arbitrary.)]

[0039] [3] The fluorine atom-containing silane compound according to [2], wherein X B is -(CR A1 e1 H 2－e1 ) a1 -(CFH) b1 -(CH 2 ) c1 -(O) d1 - the group shown.

[0040] [In the formula:

[0041] R A1 is a monovalent organic group having A 1 γ11 A 2 γ12 C-;

[0042] A 1 , A 2 , γ11, γ12, e1, a1, b1, c1, and d1 have the same meanings as in [2];

[0043] The order of existence of each repeating unit with the labeling symbols a1, b1, c1, and d1 enclosed in parentheses is arbitrary.)]

[0044] [4] The fluorine atom-containing silane compound according to [2], wherein X B is -(CFH) b1 -(CH 2 ) c1 -(O) d1 - the group shown.

[0045] [In the formula:

[0046] b1 and c1 have the same meanings as in [2];

[0047] d1 is an integer from 0 to 10; and

[0048] The order of existence of each repeating unit with the labeling symbols b1, c1, and d1 enclosed in parentheses is arbitrary.)]

[0049] [5] The fluorine atom-containing silane compound as described in [2], wherein X B is a group represented by -(CH 2 ) c1 -.

[0050] [In the formula, c1 is an integer from 0 to 30.]

[0051] [6] The fluorine atom-containing silane compound as described in [2], wherein X B is a group represented by -O-(CH 2 ) c1 -.

[0052] [In the formula, c1 is an integer from 0 to 30.]

[0053] [7] The fluorine atom-containing silane compound as described in [2], wherein X B is a group represented by -(CH 2 ) g1 -SiR s 2 O(-SiR s 2 O-) n11 SiR s 2 -(CH 2 ) g1 -.

[0054] [In the formula:

[0055] R s are each independently a hydrogen atom, a hydroxyl group or a hydrocarbon group,

[0056] n11 is an integer from 1 to 1500,

[0057] g1 are each independently an integer from 0 to 30.]

[0058] [8] The fluorine atom-containing silane compound according to any one of [1] to [7], wherein A 1 γ11 A 2 γ12 C- is HCF 2 -.

[0059] [9] The fluorine atom-containing silane compound according to any one of [1] to [8], wherein X A is a single bond, -(X 52 ) l5 - or a group represented by the formula (X A1 ):

[0060] shown.

[0061] [Wherein:

[0062] X 52 are each independently selected from -O-, -S-, ortho-phenylene, meta-phenylene or para-phenylene, -CO-, -C(O)O-, -OC(O)-, -CONR 53 -, -NR 53 CO-, -O-CONR 53 -, -NR 53 CO-O-, -NR 53 CONR 5 -, -NR 54 -, and -(CH 2 ) n5 -;

[0063] R 54 are each independently a hydrogen atom or a monovalent organic group;

[0064] n5 are each independently an integer from 1 to 30;

[0065] l5 is an integer from 1 to 10;

[0066] X a are each independently a single bond or a divalent linking group.]

[0067]

[10] The fluorine atom-containing silane compound according to any one of [1] to [9], wherein R Si is a group represented by the following formula (S1), (S2), (S3), (S4) or (S5).

[0068]

[0069] -SiR 11 n1 R 12 3-n1 (S2)

[0070] -SiR a1 k1 R b1 11 R c1 m1 (S3)

[0071] -CR d1 k2 R e1 l2 R f1 m2 (S4)

[0072] -NR g1 k3 R h113 (S5)

[0073] [wherein:

[0074] R 11 are each independently a hydroxyl group or a hydrolyzable group;

[0075] R 12 are each independently a monovalent organic group;

[0076] n1 is each independently an integer of 0 to 3 in each (SiR 11 n1 R 12 3－n1 ) unit;

[0077] X 11 are each independently a single bond or a divalent organic group;

[0078] R 13 are each independently a hydrogen atom or a monovalent organic group;

[0079] t is each independently an integer of 2 or more;

[0080] R 14 are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3－n1 ;

[0081] R 15 are each independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms;

[0082] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 ;

[0083] Z 1 are each independently a divalent organic group;

[0084] R 21 are each independently -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' ;

[0085] R 22Each is independently a hydroxyl group or a hydrolyzable group;

[0086] R 23 Each is independently a monovalent organic group;

[0087] p1 is independently an integer from 0 to 3;

[0088] q1 is independently an integer from 0 to 3;

[0089] r1 is independently an integer from 0 to 3;

[0090] Z 1' Each is independently a divalent organic group;

[0091] R 21' Each is independently -Z 1” -SiR 22” q1” R 23” r1” ;

[0092] R 22' Each is independently a hydroxyl group or a hydrolyzable group;

[0093] R 23' Each is independently a monovalent organic group;

[0094] p1' is independently an integer from 0 to 3;

[0095] q1' is independently an integer from 0 to 3;

[0096] r1' is independently an integer from 0 to 3;

[0097] Z 1” Each is independently a divalent organic group;

[0098] R 22” Each is independently a hydroxyl group or a hydrolyzable group;

[0099] R 23” Each is independently a monovalent organic group;

[0100] q1” is independently an integer from 0 to 3;

[0101] r1” is independently an integer from 0 to 3;

[0102] R b1 Each is independently a hydroxyl group or a hydrolyzable group;

[0103] R c1 Each is independently a monovalent organic group;

[0104] k1 is independently an integer from 0 to 3;

[0105] l1 is independently an integer from 0 to 3;

[0106] m1 is independently an integer from 0 to 3;

[0107] R d1 is independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 ;

[0108] Z 2 is independently a single bond, an oxygen atom or a divalent organic group;

[0109] R 31 is independently -Z 2' -CR 32' q2' R 33' r2' ;

[0110] R 32 is independently -Z 3 -SiR 34 n2 R 35 3－n2 ;

[0111] R 33 is independently a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0112] p2 is independently an integer from 0 to 3;

[0113] q2 is independently an integer from 0 to 3;

[0114] r2 is independently an integer from 0 to 3;

[0115] Z 2' is independently a single bond, an oxygen atom or a divalent organic group;

[0116] R 32' is independently -Z 3 -SiR 34 n2 R 35 3－n2 ;

[0117] R 33' is independently a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0118] q2' is independently an integer from 0 to 3;

[0119] r2' is independently an integer from 0 to 3;

[0120] Z 3 are independently a single bond, an oxygen atom or a divalent organic group;

[0121] R 34 are independently a hydroxyl group or a hydrolyzable group;

[0122] R 35 are each independently a monovalent organic group;

[0123] n2 are each independently an integer from 0 to 3;

[0124] R e1 Independently -Z 3 -SiR 34 n2 R 35 3－n2 ;

[0125] R f1 are independently a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0126] k2 are each independently an integer from 0 to 3;

[0127] l2 are each independently an integer from 0 to 3;

[0128] m2 is an integer of 0-3 respectively independently.

[0129] R g1 and R h1 Independently -Z 4 -SiR 11 n1 R 12 3－n1 , -Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 ;

[0130] Z 4 are independently a single bond, an oxygen atom or a divalent organic group;

[0131] k3 is 1 or 2;

[0132] l3 is 0 or 1;

[0133] Among them, in formula (S1), (S2), (S3), (S4) or (S5), there are at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group.

[0134]

[11] A surface treatment agent containing the fluorine atom-containing silane compound described in any one of [1] to

[10] .

[0135]

[12] The surface treatment agent as described in

[11] , which further contains a condensate of the fluorine atom-containing silane compound described in [1].

[0136]

[13] The surface treatment agent as described in

[11] or

[12] , which further contains an alcohol represented by R 90 -OH (wherein R 90 is a monovalent organic group).

[0137]

[14] The surface treatment agent as described in any one of

[11] to

[13] , which is used for vacuum evaporation coating.

[0138]

[15] The surface treatment agent as described in any one of

[11] to

[13] , which is used for wet covering.

[0139]

[16] A pellet containing the surface treatment agent as described in any one of

[11] to

[15] .

[0140]

[17] An article including a substrate and a layer formed of the fluorine atom-containing silane compound described in any one of [1] to

[10] on the substrate.

[0141]

[18] The article as described in

[17] , wherein an intermediate layer containing silicon oxide is included between the above-mentioned substrate and the above-mentioned layer.

[0142]

[19] The article as described in

[18] , wherein the above-mentioned intermediate layer contains an alkali metal atom.

[0143]

[20] The article as described in

[19] , wherein at least a part of the above-mentioned alkali metal atoms is sodium.

[0144]

[21] The article as described in any one of

[17] to

[20] , which is an optical component.

[0145]

[22] The article as described in

[21] , which is a display.

[0146]

[23] Compounds represented by the following formulas (2a) to (2g).

[0147]

[0148] Rf 1’ -XB3 -X A3 -CH=CH 2 …(2b)

[0149] Rf 1’ -X B4 -X A4 -Si(X A5 -CH=CH 2 ) δ3 R 95 3-δ3 …(2c)

[0150] Rf 1’ -X B4 -X A4 -C(X A6 -CH=CH 2 ) δ4 R 96 3-84 …(2d)

[0151] Rf 1’ -X B4 -X A4 -NR 97 2 …(2e)

[0152] Rf 1’ -X B5 -X A7 -NR 53 -R 98 …(2f)

[0153]

[0154] [wherein:

[0155] Rf 1' -are each independently A 11 γ11 A 12 γ12 C-or a cyclic structure containing CF≡;

[0156] A 11 is a fluorine atom;

[0157] A 12 are each independently a hydrogen atom, a chlorine atom or a bromine atom;

[0158] γ11 are each independently 0 or 1;

[0159] γ12 are each independently 1 or 2;

[0160] The sum of γ11 and γ12 is 3;

[0161] -R 91 is hydroxyl, -F, -Cl or -O-C 1－3 alkyl;

[0162] X B2 is (CH 2 ) c21 , (CH 2 ) c22 -O-(CH 2 ) c23 or a divalent polysiloxane-containing group;

[0163] c21, c22 and c23 are each independently an integer from 0 to 200;

[0164] wherein the sum of c22 and c23 is an integer from 0 to 200;

[0165] Rf 1' -X B2 - is Rf 1 -;

[0166] Rf 1 - each independently has at least one group selected from monovalent organic groups having A 1 γ11 A 2 γ12 C- and monovalent organic groups including a cyclic structure containing CF≡;

[0167] X B3 is (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group;

[0168] c11, c12 and c13 are each independently an integer from 0 to 200;

[0169] wherein the sum of c12 and c13 is an integer from 0 to 200;

[0170] X A3 each independently is a single bond or C(=O)NR 53 -(CH 2 ) c14 ;

[0171] R 53 is a hydrogen atom or a monovalent organic group;

[0172] c14 is an integer from 0 to 30;

[0173] X B4Each is independently (CH 2 ) c11 、(CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group;

[0174] c11, c12 and c13 are each independently an integer from 0 to 200;

[0175] wherein, the sum of c12 and c13 is an integer from 0 to 200;

[0176] Rf 1' -X B4 -is equivalent to Rf 1 -;

[0177] Rf 1 -each independently has at least one group selected from monovalent organic groups having A 1 γ11 A 2 γ12 C-and monovalent organic groups including a cyclic structure containing CF≡;

[0178] X A4 each independently is a single bond or C(=O)NR 53 -(CH 2 ) c15 ;

[0179] c15 is an integer from 0 to 30;

[0180] X A5 each independently is a single bond or a divalent organic group;

[0181] R 95 each independently is a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0182] δ3 is an integer from 1 to 3;

[0183] X A6 each independently is a single bond, an oxygen atom or a divalent organic group;

[0184] R 96 each independently is a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0185] δ4 is an integer from 1 to 3;

[0186] -R 97 each independently consists of -R 92 -CH=CH 2 or -R 94 -Q A1 (R92 -CH=CH 2 ) δ31 R 93 δ32 represents;

[0187] R 92 is a single bond, an oxygen atom or a divalent organic group;

[0188] R 94 is a single bond, an oxygen atom or a divalent organic group;

[0189] Q A1 are each independently N, Si or C;

[0190] R 93 is a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0191] δ31 and δ32 are each independently an integer of 1 or more;

[0192] The sum of δ31 and δ32 is Q A1 valence number - 1;

[0193] X B5 is represented by (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group;

[0194] c11, c12 and c13 are each independently an integer from 0 to 200;

[0195] wherein the sum of c12 and c13 is an integer from 0 to 200;

[0196] X A7 is a single bond or C(=O);

[0197] -R 98 is represented by -R 92 -CH=CH 2 or -R 94 -Q A1 (R 92 -CH=CH 2 ) δ31 R 93 δ32 represents;

[0198] -R A31 is represented by -Rf 1 represents;

[0199] Rf 1 - each independently has a selected from those having A1 γ11 A 2 γ12 At least one group selected from a monovalent organic group of C− and a monovalent organic group including a cyclic structure containing CF≡;

[0200] -R A32 Consisting of -X A31 -CH=CH 2 Or -X A33 -Q A2 (X A32 -CH=CH 2 ) δ41 R 36 δ42 Denote;

[0201] -R A33 Consisting of -Rf 1 , -X A31 -CH=CH 2 Or -X A33 -Q A2 (X A32 -CH=CH 2 ) δ41 R 36 δ42 Denote;

[0202] X A31 , X A32 And X A33 Are each independently a single bond, an oxygen atom or a divalent organic group;

[0203] Q A2 Are each independently N, Si or C;

[0204] R 36 Is a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0205] δ41 and δ42 are each independently an integer of 1 or more;

[0206] The sum of δ41 and δ42 is the valence number of Q A2 −1.]

[0207] Advantages of the Invention

[0208] According to the present invention, a novel fluorine atom-containing silane compound can be provided. Detailed Embodiments

[0209] As used in this specification, the "monovalent organic group" refers to a monovalent group containing carbon. The monovalent organic group is not particularly limited and may be a hydrocarbon group or a derivative thereof. The derivative of the hydrocarbon group refers to a group having one or more N, O, S, Si, amide group, sulfonyl group, siloxane, carbonyl group, carbonyloxy group, etc. at the end or in the molecular chain of the hydrocarbon group.

[0210] As used in this specification, the "divalent organic group" is not particularly limited, and examples thereof include divalent groups obtained by further removing one hydrogen atom from a hydrocarbon group.

[0211] As used in this specification, the "hydrocarbon group" is a group containing carbon and hydrogen, and refers to a group obtained by removing one hydrogen atom from a molecule. The hydrocarbon group is not particularly limited, and examples thereof include hydrocarbon groups having 1 to 20 carbon atoms, such as aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The above-mentioned "aliphatic hydrocarbon group" may be any of linear, branched or cyclic, and may be any of saturated or unsaturated. In addition, the hydrocarbon group may contain one or more ring structures. Such a hydrocarbon group may also be substituted with one or more substituents. Further, such a hydrocarbon group may have one or more N, O, S, Si, amide group, sulfonyl group, siloxane, carbonyl group, carbonyloxy group, etc. at its end or in the molecular chain.

[0212] As used in this specification, the substituents of the "hydrocarbon group" are not particularly limited, and examples thereof include groups selected from a halogen atom, a C 1－6 alkyl group which may be substituted with one or more halogen atoms, a C 2－6 alkenyl group, a C 2－6 alkynyl group, a C 3－10 cycloalkyl group, a C 3－10 unsaturated cycloalkyl group, a 5- to 10-membered heterocyclic group, a 5- to 10-membered unsaturated heterocyclic group, a C 6－10 aryl group, and a 5- to 10-membered heteroaryl group.

[0213] As used in this specification, the "hydrolyzable group" refers to a group capable of undergoing a hydrolysis reaction, that is, a group capable of detaching from the main skeleton of a compound through a hydrolysis reaction. Examples of the hydrolyzable group include -OR h , -OCOR h , -O-N=CR h 2 , -NR h 2 , -NHR h or -NCO (in these formulas, R h represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms), etc., and preferably -OR h (i.e., an alkoxy group). R hExamples include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl; and substituted alkyl groups such as chloromethyl. Among these, alkyl groups are preferred, unsubstituted alkyl groups are particularly preferred, and methyl or ethyl is more preferred. In one embodiment, R h is methyl, and in another embodiment, R h is ethyl.

[0214] [Silane compound containing fluorine atoms]

[0215] The silane compound containing fluorine atoms of the present invention is represented by the following formula (1).

[0216] (Rf 1 ) α1 -X A -(R Si ) α2 …(1)

[0217] Rf 1 each independently has at least one group selected from monovalent organic groups having A 1 γ11 A 2 γ12 C- and monovalent organic groups including a cyclic structure containing a CF≡ group.

[0218] A 1 is a fluorine atom.

[0219] A 2 each independently is a hydrogen atom, a chlorine atom or a bromine atom.

[0220] In one embodiment, A 2 is a hydrogen atom. In one embodiment, A 2 is a chlorine atom. In another embodiment, A 2 is a bromine atom.

[0221] The above A 2 is preferably a hydrogen atom.

[0222] In one embodiment, A 1 γ11 A 2 γ12 C- is HF 2 C-.

[0223] γ11 are each independently 1 or 2; γ12 are each independently 1 or 2. Among them, the sum of γ11 and γ12 is 3.

[0224] In one embodiment, γ11 is 1. In one embodiment, γ11 is 2.

[0225] In one embodiment, γ12 is 1. In one embodiment, γ12 is 2.

[0226] The above-mentioned "ring structure containing CF≡" is a structure in which a carbon atom has a fluorine atom and three connecting parts, and the connecting parts form a part of the ring structure.

[0227] In one embodiment, Rf 1 is a monovalent organic group including a ring structure containing CF≡, for example, a monovalent organic group including the following structure. * represents the bonding site.

[0228]

[0229] In one embodiment, Rf 1 is A 1 γ11 A 2 γ12 C-X B -shown group.

[0230] A 1 、A 2 、γ11 and γ12 have the same meanings as above.

[0231] X B is a single bond, a divalent polysiloxane-containing group or -(CR A1 e1 H 2－e1 ) a1 -(CFH) b1 -(CH 2 ) c1 -(O) d1 -shown group. Wherein in X B , the left side is bonded to A 1 γ11 A 2 γ12 C-, and the right side is bonded to -X A -.

[0232] As a specific example of Rf 1 , for example, the following groups can be listed. In the following formula, * represents the bonding position with X A .

[0233]

[0234] In X B ,

[0235] R A1 is a monovalent organic group having A 1 γ11 A 2 γ12 C-;

[0236] e1 is 1 or 2.

[0237] a1 is an integer from 0 to 200;

[0238] b1 is an integer from 0 to 200;

[0239] c1 is an integer from 0 to 200;

[0240] d1 is an integer from 0 to 200; and,

[0241] The order of existence of each repeating unit in which the labeling symbols a1, b1, c1, and d1 are enclosed in parentheses is arbitrary. Preferably X B does not contain a structure in which two or more oxygen atoms are continuously bonded.

[0242] In one embodiment, X B is a group represented by -(CR A1 e1 H 2－e1 ) a1 -(CFH) b1 -(CH 2 ) c1 -(O) d1 -.

[0243] R A1 , e1, a1, b1, c1, and d1 have the same meanings as above. The order of existence of each repeating unit in which the labeling symbols a1, b1, c1, and d1 are enclosed in parentheses is arbitrary.

[0244] In one embodiment, R A1 is HCF 2 - or HCF 2 O-.

[0245] In one embodiment, e1 is 1, and in another embodiment, e1 is 2.

[0246] In one embodiment, a1 is 0 or 1.

[0247] In one embodiment, b1 is an integer from 0 to 6.

[0248] In one embodiment, c1 is an integer from 0 to 30.

[0249] In one embodiment, d1 is an integer from 0 to 10, and in another embodiment, d1 is an integer from 0 to 3.

[0250] In one embodiment, e1 is 1 or 2, a1 is 0 or 1, b1 is an integer from 0 to 200, c1 is an integer from 0 to 200, and d1 is an integer from 0 to 10. The order of existence of each repeating unit in which the labeling symbols a1, b1, c1, and d1 are enclosed in parentheses is arbitrary.

[0251] In one embodiment, e1 is 1 or 2, a1 is 0 or 1, b1 is an integer from 0 to 6, c1 is an integer from 0 to 30, and d1 is an integer from 0 to 3. The order of existence of each repeating unit with the reference signs a1, b1, c1, and d1 enclosed in parentheses is arbitrary.

[0252] In one embodiment, X B is -(CFH) b1 -(CH 2 ) c1 -(O) d1 - as shown in the group.

[0253] The meanings of b1, c1, and d1 are the same as above. The order of existence of each repeating unit with the reference signs b1, c1, and d1 enclosed in parentheses is arbitrary.

[0254] Preferably, the meanings of b1 and c1 are the same as above, and d1 is an integer from 0 to 10; more preferably, b1 is an integer from 0 to 6, c1 is an integer from 0 to 30, and d1 is an integer from 0 to 3.

[0255] In one embodiment, X B is -(CR A1 e1 H 2－e1 ) a1 -(CH 2 ) c1 - as shown in the group. R A1 , e1, a1, and c1 have the same meanings as above.

[0256] In one embodiment, X B is -(CH 2 ) c1 - as shown in the group. The meaning of c1 is the same as above. Preferably, c1 is an integer from 0 to 30. In one embodiment, c1 is an integer from 1 to 9. In one embodiment, c1 is an integer from 10 to 25.

[0257] In one embodiment, X B is -(CR A1 e1 H 2－e1 ) a1 -O-(CH 2 ) c1 - as shown in the group.

[0258] R A1 , e1, a1, and c1 have the same meanings as above.

[0259] In one embodiment, X B is -O-(CH 2 ) c1 - as shown in the group.

[0260] The meaning of c1 is the same as above. Preferably, c1 is an integer from 0 to 30.

[0261] In one embodiment, X B is -(CR A1 e1 H 2－e1 ) a1 -(CH 2 ) c1 -O- as shown by the group.

[0262] R A1 , e1, a1 and c1 have the same meanings as above.

[0263] In one embodiment, X B is -(CH 2 ) c1 -O- as shown by the group.

[0264] The meaning of c1 is the same as above. In one embodiment, c1 is an integer from 0 to 30; in one embodiment, c1 is an integer from 0 to 10.

[0265] In one embodiment, X B is -(CH 2 ) c10 -O-(CH 2 ) c10 - as shown by the group. c10 are each independently an integer from 0 to 200. Among them, the total number of carbon atoms in the above X B is an integer from 0 to 200. For example, c10 are each independently an integer from 0 to 30.

[0266] In one embodiment, X B is a divalent polysiloxane-containing group, including a structure in which two silicons are bonded through oxygen (-Si-O-Si-). X B is preferably -R k31 -(CH 2 ) g1 -SiR s 2 O(-SiR s 2 O-) n11 SiR s 2 -R k32 -, more preferably -(CH 2 ) g1 -SiR s 2 O(-SiR s 2 O-) n11 SiR s 2 -(CH2 ) g1 - the group shown.

[0267] R k31 is a single bond or C 1－200 alkylene, for example, a single bond.

[0268] R k32 is a single bond or C 1－200 alkylene, for example, C 1－10 alkylene.

[0269] Among them, the number of carbon atoms contained in R k31 and the number of carbon atoms contained in R k32 add up to 0 to 200.

[0270] g1 are each independently an integer from 0 to 30. g1 is, for example, an integer from 1 to 30, specifically an integer from 1 to 10, and more specifically an integer from 1 to 3. In one embodiment, g1 is 0.

[0271] R s are each independently a hydrogen atom, a hydroxyl group, or a hydrocarbon group;

[0272] n11 is an integer from 1 to 1500.

[0273] As the above-mentioned hydrocarbon group, for example, C 1－3 alkyl can be cited.

[0274] Specifically, as -SiR s 2 O(-SiR s 2 O-) n11 SiR s 2 -, polydimethylsiloxanyl, polydiethylsiloxanyl, etc. can be cited.

[0275] In one embodiment, X B is the group shown as -(CH 2 ) c11 -(O(CH 2 ) c12 ) c13 -.

[0276] c11 is an integer from 0 to 200, c12 is an integer from 0 to 200, and c13 is an integer from 0 to 200. Among them, the number of carbon atoms contained in the above X B is an integer from 0 to 200. For example, c12 and c13 are each an integer of 1 or more.

[0277] For example, c11 is an integer from 1 to 4, c12 is an integer from 1 to 10, and c13 is an integer from 1 to 150.

[0278] In one embodiment, the above X B contains an integer number of carbon atoms from 1 to 150.

[0279] In one embodiment, c11 is an integer from 0 to 20, c12 is an integer from 1 to 6, c13 is an integer from 0 to 150, preferably c13 is an integer from 1 to 50, and the above X B contains an integer number of carbon atoms from 1 to 150.

[0280] In one embodiment, c11 is an integer from 1 to 30, c12 is an integer from 1 to 3, c13 is an integer from 2 to 150, for example, an integer from 2 to 50.

[0281] In one embodiment, A 1 γ11 A 2 γ12 C− is HCF 2 −.

[0282] In one embodiment, the fluorine atom-containing silane compound does not contain a -CF 3 group and a -CF 2 - group.

[0283] In one embodiment, the fluorine atom-containing silane compound contains only Rf 1 containing fluorine atoms.

[0284] α1 is an integer from 1 to 9, and α2 is an integer from 1 to 9. These α1 and α2 can vary corresponding to the A valence of X. The sum of α1 and α2 is equal to the A valence of X. For example, when X A is a 10-valent organic group, the sum of α1 and α2 is 10. For example, α1 can be 9 and α2 can be 1, α1 can be 5 and α2 can be 5, or α1 can be 1 and α2 can be 9. Additionally, when X A is a 2-valent organic group, α1 and α2 are 1.

[0285] X A is a single bond, an oxygen atom, or a 2- to 10-valent organic group. Among them, the left side of X A is bonded to Rf 1 and the right side is bonded to R Si .

[0286] The above X A can be understood as a linking group that connects the Rf 1 portion to the portion (R Si portion) that provides the binding ability to the substrate. Therefore, as long as the compound represented by formula (1) can stably exist, this X AIt can be a single bond, an oxygen atom, or any organic group.

[0287] The above X A can each independently be substituted with one or more substituents selected from a fluorine atom, a C 1－3 alkyl group, and a C 1－3 fluoroalkyl group (preferably a C 1－3 perfluoroalkyl group). In one embodiment, X A is unsubstituted.

[0288] The above X A The 2- to 10-valent organic group is preferably a 2- to 8-valent organic group. In one embodiment, the 2- to 10-valent organic group is preferably a 2- to 4-valent organic group, more preferably a 2-valent organic group. In another embodiment, the 2- to 10-valent organic group is preferably a 3- to 8-valent organic group, more preferably a 3- to 6-valent organic group.

[0289] In one embodiment, X A is a single bond.

[0290] In one embodiment, X A is an oxygen atom.

[0291] In one embodiment, X A is a 2- to 10-valent organic group.

[0292] In one embodiment, X A is a single bond or a 2-valent organic group, and α1 and α2 are 1.

[0293] In one embodiment, the above X A is a 2-valent organic group, and α1 and α2 are 1.

[0294] In one embodiment, X A is a 3- to 6-valent organic group, α1 is 1, and α2 is 2 to 5.

[0295] In one embodiment, X A is a 3-valent organic group, α1 is 1, and α2 is 2.

[0296] In one embodiment, X A is a 3-valent organic group, α1 is 2, and α2 is 1.

[0297] In one embodiment, the above X A is represented by a single bond, -(X 52 ) l5 -, or formula (X A1 ):

[0298] is represented.

[0299] The above X52 are each independently selected from -O-, -S-, ortho-phenylene, meta-phenylene or para-phenylene, -CO-, -C(O)O-, -OC(O)-, -CONR 53 -, -NR 53 CO-, -O-CONR 53 -, -NR 53 CO-O-, -NR 53 CONR 53 -, -NR 53 -, and -(CH 2 ) n5 - groups.

[0300] The above R 53 are each independently a hydrogen atom or a monovalent organic group, preferably a hydrogen atom, a phenyl group, a C 1－6 alkyl group (preferably a methyl group) or a group of an oxyalkylene having 1 to 10 carbon atoms.

[0301] The above n5 are each independently an integer from 1 to 200. n5 is, for example, an integer from 1 to 30, specifically an integer from 1 to 20, more specifically an integer from 1 to 15, an integer from 1 to 10, an integer from 1 to 6, for example an integer from 1 to 3. In one embodiment, n5 is an integer from 10 to 200, for example an integer from 10 to 30. In one embodiment, n5 is an integer from 1 to 9.

[0302] The above l5 is an integer from 1 to 10, preferably an integer from 1 to 5, more preferably an integer from 1 to 3.

[0303] The group of the oxyalkylene having 1 to 10 carbon atoms is a group containing -O-C 1－10 alkylene-, for example, -R 55 -( -O-C 1－10 alkylene) n -R 56 (wherein, R 55 is a single bond or a divalent organic group, preferably a C 1﹣6 alkylene, n is an arbitrary integer, preferably an integer from 2 to 10, and R 56 is a hydrogen atom or a monovalent organic group, preferably a C 1﹣6 alkyl group). The above alkylene may be linear or branched.

[0304] The above X a is a single bond or a divalent linking group directly bonded to the isocyanuric acid ring. As X a, preferably a single bond, an alkylene group, or a divalent group containing at least one bond selected from an ether bond, an ester bond, an amide bond, and a thioether bond, more preferably a single bond, an alkylene group having 1 to 10 carbon atoms, or a divalent hydrocarbon group having 1 to 10 carbon atoms and containing at least one bond selected from an ether bond, an ester bond, an amide bond, and a thioether bond. The above X a is bonded to the isocyanuric acid ring on the left side.

[0305] One to two groups having X a are bonded to the Rf 1 group, and one to two groups having X a are bonded to the R Si group. Among them, the total number of groups having X a is 3. In one embodiment, one of the groups having X a is bonded to the Rf 1 group, and two of the groups having X a are bonded to the R Si group. In one embodiment, two of the groups having X a are bonded to the Rf 1 group, and one of the groups having X a is bonded to the R Si group.

[0306] As the above X a , it is more preferably a group represented by the following formula: -(CX 121 X 122 ) x1 -(X a11 ) y1 -(CX 123 X 124 ) z1 -.

[0307] [In the formula,

[0308] X 121 to X 124 are each independently H, OH, or -OSi(OR 121 ) 3 (in the formula, the three Rs 121 are each independently an alkyl group having 1 to 4 carbon atoms),

[0309] X a11 is -C(=O)NH-, -NHC(=O)-, -O-, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -NHC(=O)NH-, -NR 122 -, -C(=O)-NR 122 -, -NR 122 -C(=O)- or S (the left side of each bond is with CX 121 X122 bonding)

[0310] R 122 is a hydrocarbon chain of C 1－6 , preferably a C 1－6 alkyl group

[0311] x1 is an integer from 0 to 10, y1 is 0 or 1, and z1 is an integer from 1 to 10.]

[0312] In another embodiment, R122 is a hydrogen atom.

[0313] As the above X a11 , preferably -O-, -C(=O)O-, or -C(=O)NH-.

[0314] As the above X a , preferably a group represented by the following formula:

[0315] -(CH 2 ) m12 -O-(CH 2 ) m13 -(wherein, m12 is an integer from 1 to 10, and m13 is an integer from 1 to 10),

[0316] -(CH 2 ) m15 -O-CH 2 CH(OH)-(CH 2 ) m16 -(wherein, m15 is an integer from 1 to 10, and m16 is an integer from 1 to 10),

[0317] -(CH 2 ) m18 -(wherein, m18 is an integer from 1 to 10), or

[0318] -(CH 2 ) m20 -O-CH 2 CH(OSi(OCH 3 ) 3 )-(CH 2 ) m21 -(wherein, m20 is an integer from 1 to 10, and m21 is an integer from 1 to 10).

[0319] As the above X a , there is no particular limitation, and examples include -CH 2 -, -C 2 H 4 -, -C 3 H 6 -, -C 4 H 8 -C4 H 8 -O-CH 2 -、-CO-O-CH 2 -CH(OH)-CH 2 -、-S-、-NR 53 -、-(CH 2 ) m22 -C(=O)-O-(CH 2 ) m23 -、-(CH 2 ) m22 -O-C(=O)-(CH 2 ) m23 -、-(CH 2 ) m22 -C(=O)-NR 53 -(CH 2 ) m23 -、-(CH 2 ) m22 -NR 53 -C(=O)-(CH 2 ) m23 -CH 2 OCH 2 CH(OSi(OCH 3 ) 3 )CH 2 -(wherein the meaning of R 53 is the same as above, preferably a hydrogen atom or a C 1－6 hydrocarbon chain (such as a C 1－6 alkyl group, specifically a methyl group), m22 is an integer from 1 to 10, and m23 is an integer from 1 to 10), etc.)

[0320] When the above X A is a single bond, an oxygen atom or a divalent organic group, formula (1) is represented by the following formula (1').

[0321] Rf 1 -X A -R Si …(1')

[0322] The above X A is preferably a single bond or a divalent organic group.

[0323] In one embodiment, the above X A is independently represented by -(X 52 ) l5 -R 52 -. The above R 52 is a single bond, -(CH 2 ) t5 - or ortho-phenylene, meta-phenylene or para-phenylene, preferably -(CH2 ) t5 -. The above t5 is an integer from 1 to 20, preferably an integer from 2 to 6, more preferably an integer from 2 to 3. Here, R 52 (typically a hydrogen atom of R 52 ) can be substituted by one or more substituents selected from a fluorine atom, a C 1－3 alkyl group, and a C 1－3 fluoroalkyl group. In a preferred embodiment, R 52 is not substituted by these groups.

[0324] For example, as the above X A , the following can be listed independently of each other:

[0325] a single bond,

[0326] -CONR 53 -(CH 2 ) n5 -,

[0327] -(CH 2 ) n5 -CONR 53 -(CH 2 ) n5 -,

[0328] -(CH 2 ) n5 -CONR 53 -,

[0329] -(CH 2 ) n5 -,

[0330] -OC(=O)-(CH 2 ) n5 -,

[0331] -(CH 2 ) n5 -OC(=O)-(CH 2 ) n5 -,

[0332] -C(=O)O-(CH 2 ) n5 -,

[0333] -(CH 2 ) n5 -C(=O)O-(CH 2 ) n5 -,

[0334] -C(=O)-(CH 2 ) n5 -,

[0335] -(CH 2 ) n5 -C(=O)-(CH 2 ) n5 -. R 53 The meanings of n5 are the same as above respectively.

[0336] In one embodiment, as the above X A , the following can be listed independently:

[0337] A single bond,

[0338] -CONR 53 -(CH 2 ) n5 -、

[0339] -OC(=O)-(CH 2 ) n5 -、

[0340] -C(=O)-(CH 2 ) n5 -.

[0341] In one embodiment, the above X 52 are independently selected from -S-, ortho-phenylene, meta-phenylene or para-phenylene, -CO-, -C(O)O-, -OC(O)-, -CONR 53 -, -O-CONR 53 -, -NR 53 CO-, -O-CONR 53 -, -NR 53 CO-O- and -NR 53 - groups.

[0342] In one embodiment, the above X 52 is -(CH 2 ) n5 -CONR 53 -.

[0343] In one embodiment, the above X A can be the groups represented by the following formula.

[0344]

[0345] R Si is a monovalent group containing a Si atom bonded to a hydroxyl group or a hydrolyzable group.

[0346] R Si is preferably a group represented by formula (S1), (S2), (S3), (S4) or (S5).

[0347]

[0348] -SiR 11 n1 R 12 3-n1 (S2)

[0349] -SiR a1 k1 R b1 l1 R c1 m1 (S3)

[0350] -CR d1 k2 R e1 l2 R f1 m2 (S4)

[0351] -NR g1 k3 R h1 13 (S5)

[0352] R 11 are each independently a hydroxyl group or a hydrolyzable group.

[0353] R 11 Preferably, they are each independently a hydrolyzable group.

[0354] R 12 are each independently a monovalent organic group. However, R 12 does not include a hydrolyzable group.

[0355] In R 12 the monovalent organic group is preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group, and even more preferably a methyl group.

[0356] n1 is each independently an integer of 0 to 3 in each (SiR 11 n1 R 12 3－n1 ) unit. Among them, in formula (S1), there are at least 2 (SiR 11 n1 R 12 3－n1 ) units in which n1 is 1 to 3. In other words, in formula (S1), there are at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group.

[0357] n1 in each (SiR 11 n1 R12 3－n1 In the unit, it is preferably an integer of 1 to 3, more preferably 2 to 3, and further preferably 3, independently of each other.

[0358] In the above formula, X 11 is independently a single bond or a divalent organic group. The divalent organic group is preferably -R 28 -O x -R 29 -(wherein, R 28 and R 29 are independently a single bond or C 1－20 alkylene, and x is 0 or 1). The C 1－20 alkylene can be linear or branched, preferably linear. The C 1－20 alkylene is preferably C 1－10 alkylene, more preferably C 1－6 alkylene, and further preferably C 1－3 alkylene.

[0359] In one embodiment, X 11 is independently -C 1－6 alkylene -O-C 1－6 alkylene - or -O-C 1－6 alkylene -.

[0360] In a preferred embodiment, X 11 is independently a single bond or a linear C 1－6 alkylene, preferably a single bond or a linear C 1－3 alkylene, more preferably a single bond or a linear C 1－2 alkylene, and further preferably a linear C 1－2 alkylene.

[0361] R 13 is independently a hydrogen atom or a monovalent organic group. The monovalent organic group is preferably C 1－20 alkyl.

[0362] In a preferred embodiment, R 13 is independently a hydrogen atom or a linear C 1－6 alkyl, preferably a hydrogen atom or a linear C 1－3 alkyl, and more preferably a hydrogen atom or a methyl group.

[0363] R 15 is independently a single bond, an oxygen atom, C 1－6 alkylene or C 1－6 alkoxy.

[0364] In one embodiment, R 15 is independently an oxygen atom, C 1－6Alkylene or C 1－6 Alkoxy.

[0365] In a preferred embodiment, R 15 is a single bond.

[0366] t are each independently an integer of 2 or more.

[0367] In a preferred embodiment, t are each independently an integer of 2 to 10, preferably an integer of 2 to 6.

[0368] R 14 are each independently a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3－n1 . The halogen atom is preferably an iodine atom, a chlorine atom or a fluorine atom, more preferably a fluorine atom. In a preferred embodiment, R 14 is a hydrogen atom.

[0369] In one embodiment, formula (S1) is the following formula (S1-a).

[0370]

[0371] [In the formula,

[0372] R 11 , R 12 , R 13 , X 11 and the meanings of n1 are the same as those described in formula (S1) above;

[0373] t1 and t2 are each independently an integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 2 to 10, for example an integer of 1 to 5 or an integer of 2 to 5;

[0374] The order of existence of each repeating unit marked with t1 and t2 and enclosed in parentheses is arbitrary in the formula. ]

[0375] In a preferred embodiment, formula (S1) is the following formula (S1-b).

[0376]

[0377] [In the formula, R 11 , R 12 , R 13 , X 11 , n1 and t have the same meanings as those described in formula (S1) above. ]

[0378] In a preferred embodiment, in formula (S2), -SiR 11 n1 R12 3－n1 The Si atoms do not form siloxane bonds.

[0379] In one embodiment, there are at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group in formula (S2).

[0380] R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 .

[0381] The above-mentioned Z 1 are each independently an oxygen atom or a divalent organic group. Among them, the following is denoted as Z 1 The right side of the structure is bonded to the (SiR 21 p1 R 22 q1 R 23 r1 ) bond.

[0382] In a preferred embodiment, Z 1 is a divalent organic group.

[0383] In a preferred embodiment, Z 1 does not include the case where a siloxane bond is formed with the Si atom to which Z 1 is bonded. Preferably, in formula (S3), (Si-Z 1 -Si) does not contain a siloxane bond.

[0384] The above-mentioned Z 1 is preferably C 1－6 alkylene, -(CH 2 ) z1 -O-(CH 2 ) z2 -(wherein, z1 is an integer from 0 to 6, such as an integer from 1 to 6, and z2 is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z3 -phenylene-(CH 2 ) z4 -(wherein, z3 is an integer from 0 to 6, such as an integer from 1 to 6, and z4 is an integer from 0 to 6, such as an integer from 1 to 6). This C 1－6 alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups can be selected from, for example, a fluorine atom, C 1－6 alkyl, C 2－6 alkenyl and C 2－6One or more substituents in the alkynyl group are substituted, but unsubstituted is preferred.

[0385] In a preferred embodiment, Z 1 is C 1－6 alkylene or -(CH 2 ) z3 -phenylene-(CH 2 ) z4 -, preferably -phenylene-(CH 2 ) z4 -.

[0386] In another preferred embodiment, the above Z 1 is C 1－3 alkylene. In one embodiment, Z 1 can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 1 can be -CH 2 CH 2 -.

[0387] R 21 are each independently -Z 1' -SiR 21' p1' R 22' q1' R 23' r1' .

[0388] The above Z 1' are each independently an oxygen atom or a divalent organic group. Hereinafter, the right side of the structure of the following Z 1' is bonded to (SiR 21' p1' R 22' q1' R 23' r1' ).

[0389] In a preferred embodiment, Z 1' is a divalent organic group.

[0390] In a preferred embodiment, Z 1' does not include the case where a siloxane bond is formed with the Si atom to which Z 1' is bonded. Preferably, in formula (S3), (Si-Z 1' -Si) does not contain a siloxane bond.

[0391] The above Z 1' is preferably C 1－6 alkylene, -(CH 2 ) z1' -O-(CH2 ) z2' -(wherein, z1' is an integer from 0 to 6, for example, an integer from 1 to 6, and z2' is an integer from 0 to 6, for example, an integer from 1 to 6) or -(CH 2 ) z3' -phenylene-(CH 2 ) z4' -(wherein, z3' is an integer from 0 to 6, for example, an integer from 1 to 6, and z4' is an integer from 0 to 6, for example, an integer from 1 to 6). The C 1－6 alkylene group can be linear or branched, preferably linear. These groups can be substituted by one or more substituents selected from, for example, a fluorine atom, C 1－6 alkyl, C 2－6 alkenyl, and C 2－6 alkynyl, but is preferably unsubstituted.

[0392] In a preferred embodiment, Z 1' is C 1－6 alkylene or -(CH 2 ) z3' -phenylene-(CH 2 ) z4' -, preferably -phenylene-(CH 2 ) z4' -.

[0393] In another preferred embodiment, the above Z 1' is C 1－3 alkylene. In one embodiment, Z 1' can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 1' can be -CH 2 CH 2 -.

[0394] R 21' are each independently -Z 1” -SiR 22” q1” R 23” r1” .

[0395] Z 1” are each independently an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 1” is bonded to (SiR 22” q1” R 23” r1” ).

[0396] In a preferred embodiment, Z 1”is a divalent organic group.

[0397] In a preferred embodiment, Z 1” does not include a case where a siloxane bond is formed with the Si atom to which Z 1” is bonded. Preferably, in formula (S3), (Si-Z 1” -Si) does not contain a siloxane bond.

[0398] Z 1” is preferably C 1－6 alkylene, -(CH 2 ) z1” -O-(CH 2 ) z2” -(wherein, z1” is an integer from 0 to 6, such as an integer from 1 to 6, and z2” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z3” -phenylene-(CH 2 ) z4” -(wherein, z3” is an integer from 0 to 6, such as an integer from 1 to 6, and z4” is an integer from 0 to 6, such as an integer from 1 to 6). This C 1－6 alkylene can be straight-chain or branched-chain, and is preferably straight-chain. These groups are substituted with one or more substituents selected from, for example, a fluorine atom, C 1－6 alkyl, C 2－6 alkenyl, and C 2－6 alkynyl, but is preferably unsubstituted.

[0399] In a preferred embodiment, Z 1” is C 1－6 alkylene or -(CH 2 ) z3” -phenylene-(CH 2 ) z4” -, preferably -phenylene-(CH 2 ) z4” -. When Z 1” is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0400] In another preferred embodiment, the above Z 1” is C 1－3 alkylene. In one embodiment, Z 1” can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 1” can be -CH 2 CH 2 -.

[0401] R 22”Each is independently a hydroxyl group or a hydrolyzable group.

[0402] R 22” Preferably, each is independently a hydrolyzable group.

[0403] R 23” Each is independently a monovalent organic group. The monovalent organic group is a monovalent organic group other than the above-mentioned hydrolyzable groups.

[0404] In R 23” the monovalent organic group is preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group, and still more preferably a methyl group.

[0405] q1” are each independently an integer from 0 to 3, and r1” are each independently an integer from 0 to 3. Among them, the sum of q1” and r1” is 3 in the (SiR 22” q1” R 23” r1” ) unit.

[0406] q1” is preferably an integer from 1 to 3, more preferably 2 to 3, and still more preferably 3, independently in each (SiR 22” q1” R 23” r1” ) unit.

[0407] R 22' Each is independently a hydroxyl group or a hydrolyzable group.

[0408] R 22' Preferably, each is independently a hydrolyzable group.

[0409] R 23' Each is independently a monovalent organic group. The monovalent organic group is a monovalent organic group other than the above-mentioned hydrolyzable groups.

[0410] In R 23' the monovalent organic group is preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group, and still more preferably a methyl group.

[0411] The above p1' are each independently an integer from 0 to 3, q1' are each independently an integer from 0 to 3, and r1' are each independently an integer from 0 to 3. Among them, the sum of p', q1' and r1' is 3 in the (SiR 21' p1' R 22' q1' R 23' r1' ) unit.

[0412] In one mode, p1' is 0.

[0413] In one mode, p1' is an integer from 1 to 3, an integer from 2 to 3, or 3, respectively and independently in each (SiR 21' p1' R 22' q1' R 23' r1' ) unit. In a preferred mode, p1' is 3.

[0414] In one mode, q1' is an integer from 1 to 3, preferably an integer from 2 to 3, more preferably 3, respectively and independently in each (SiR 21' p1' R 22' q1' R 23' r1' ) unit.

[0415] In one mode, p1' is 0 and q1' is an integer from 1 to 3, preferably an integer from 2 to 3, further preferably 3, respectively and independently in each (SiR 21' p1' R 22' q1' R 23' r1' ) unit.

[0416] R 22 are each independently a hydroxyl group or a hydrolyzable group.

[0417] R 22 Preferably, they are each independently a hydrolyzable group.

[0418] R 23 are each independently a monovalent organic group. The monovalent organic group is a monovalent organic group other than the above-mentioned hydrolyzable group.

[0419] In R 23 the monovalent organic group is preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group, and even more preferably a methyl group.

[0420] p1 is each independently an integer from 0 to 3, q1 is each independently an integer from 0 to 3, and r1 is each independently an integer from 0 to 3. Among them, the sum of p1, q1, and r1 is 3 in the (SiR 21 p1 R 22 q1 R 23 r1 ) unit.

[0421] In one mode, p1 is 0.

[0422] In one mode, p1 can be independently an integer from 1 to 3, an integer from 2 to 3, or 3 in each (SiR 21 p1 R 22 q1 R 23 r1 ) unit. In a preferred mode, p1 is 3.

[0423] In one mode, q1 can be independently an integer from 1 to 3, preferably an integer from 2 to 3, more preferably 3 in each (SiR 21 p1 R 22 q1 R 23 r1 ) unit.

[0424] In one mode, p1 is 0, and q1 can be independently an integer from 1 to 3, preferably an integer from 2 to 3, further preferably 3 in each (SiR 21 p1 R 22 q1 R 23 r1 ) unit.

[0425] R b1 are independently a hydroxyl group or a hydrolyzable group.

[0426] R b1 Preferably, they are independently hydrolyzable groups.

[0427] R c1 are independently monovalent organic groups. The monovalent organic groups are monovalent organic groups other than the above-mentioned hydrolyzable groups.

[0428] In R c1 , the monovalent organic group is preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group, and further preferably a methyl group.

[0429] k1 are independently integers from 0 to 3, l1 are independently integers from 0 to 3, and m1 are independently integers from 0 to 3. Among them, the sum of k1, l1, and m1 is 3 in the (SiR a1 k1 R b1 l1 R c1 m1 ) unit.

[0430] In one mode, k1 in each (SiR a1k1 R b1 l1 R c1 m1 ) units are each independently an integer of 1 to 3, preferably 2 or 3, and more preferably 3. In a preferred embodiment, k1 is 3.

[0431] In formula (S3), there are at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.

[0432] In a preferred embodiment, at least two Si atoms to which a hydroxyl group or a hydrolyzable group is bonded exist at the terminal portion of formula (S3).

[0433] In a preferred embodiment, the group represented by formula (S3) has -Z 1 -SiR 22 q1 R 23 r1 (wherein, q1 is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1 is an integer of 0 to 2), -Z 1' -SiR 22' q1' R 23' r1' (wherein, q1' is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1' is an integer of 0 to 2) or -Z 1” -SiR 22” q1” R 23” r1” (wherein, q1" is an integer of 1 to 3, preferably 2 or 3, more preferably 3, and r1" is an integer of 0 to 2). 1 , Z 1' , Z 1” , R 22 , R 23 , R 22' , R 23' , R 22” and R 23” Same meaning as above.

[0434] In a preferred embodiment, in formula (S3) there is R 21' In the case of at least one, preferably all, R 21' In the above, q1" is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0435] In a preferred embodiment, in formula (S3) there is R 21 In the case of at least one, preferably all, R 21 In the formula (a), p1′ is 0, and q1′ is an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

[0436] In a preferred embodiment, when there is R in formula (S3) a1 in at least one, preferably all, of the R a1 p1 is 0, q1 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0437] In a preferred embodiment, in formula (S3), k1 is 2 or 3, preferably 3, p1 is 0, and q1 is 2 or 3, preferably 3.

[0438] R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 .

[0439] Z 2 are each independently a single bond, an oxygen atom or a divalent organic group. Herein, the right side of the structure denoted as Z 2 is bonded to (CR 31 p2 R 32 q2 R 33 r2 ).

[0440] In a preferred embodiment, Z 2 is a divalent organic group.

[0441] In a preferred embodiment, Z 2 does not contain a siloxane bond.

[0442] Z 2 is preferably C 1－6 alkylene, -(CH 2 ) z5 -O-(CH 2 ) z6 -(wherein, z5 is an integer from 0 to 6, such as an integer from 1 to 6, and z6 is an integer from 0 to 6, such as an integer from 1 to 6), or -(CH 2 ) z7 -phenylene-(CH 2 ) z8 -(wherein, z7 is an integer from 0 to 6, such as an integer from 1 to 6, and z8 is an integer from 0 to 6, such as an integer from 1 to 6). This C 1－6 alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups can be selected from, for example, a fluorine atom, C 1－6 alkyl, C 2－6 alkenyl and C 2－6substituted by one or more substituents in the alkynyl group, but preferably unsubstituted.

[0443] In a preferred embodiment, Z 2 is C 1－6 alkylene or -(CH 2 ) z7 -phenylene-(CH 2 ) z8 -, preferably -phenylene-(CH 2 ) z8 -. In the case where Z 2 is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0444] In another preferred embodiment, the above Z 2 is C 1－3 alkylene. In one embodiment, Z 2 can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 2 can be -CH 2 CH 2 -.

[0445] R 31 are each independently -Z 2' -CR 32' q2' R 33' r2' .

[0446] Z 2' are each independently a single bond, an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 2' is bonded to (CR 32' q2' R 33' r2' ).

[0447] In a preferred embodiment, Z 2' does not contain a siloxane bond.

[0448] Z 2' is preferably C 1－6 alkylene, -(CH 2 ) z5' -O-(CH 2 ) z6' -(wherein, z5' is an integer from 0 to 6, such as an integer from 1 to 6, and z6' is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z7' -phenylene-(CH 2 )z8' -(wherein, z7' is an integer from 0 to 6, for example, an integer from 1 to 6, and z8' is an integer from 0 to 6, for example, an integer from 1 to 6). Such C 1－6 The alkylene group can be straight-chain or branched-chain, preferably straight-chain. These groups can be substituted by one or more substituents selected from, for example, a fluorine atom, C 1－6 alkyl group, C 2－6 alkenyl group, and C 2－6 alkynyl group, but is preferably unsubstituted.

[0449] In a preferred embodiment, Z 2' is C 1－6 alkylene group or -(CH 2 ) z7' -phenylene-(CH 2 ) z8' -, preferably -phenylene-(CH 2 ) z8' -. When Z 2' is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0450] In another preferred embodiment, the above Z 2' is C 1－3 alkylene group. In one embodiment, Z 2' can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 2' can be -CH 2 CH 2 -.

[0451] R 32' are each independently -Z 3 -SiR 34 n2 R 35 3－n2 .

[0452] Z 3 are each independently a single bond, an oxygen atom, or a divalent organic group. Among them, the right side of the structure denoted as Z 3 is bonded to (SiR 34 n2 R 35 3－n2 ).

[0453] In one embodiment, Z 3 is an oxygen atom.

[0454] In one embodiment, Z 3 is a divalent organic group.

[0455] In a preferred embodiment, Z 3 does not contain a siloxane bond.

[0456] Z 3 is preferably C 1－6 alkylene, -(CH 2 ) z5” -O-(CH 2 ) z6” -(wherein, z5” is an integer from 0 to 6, such as an integer from 1 to 6, and z6” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z7” -phenylene-(CH 2 ) z8” -(wherein, z7” is an integer from 0 to 6, such as an integer from 1 to 6, and z8” is an integer from 0 to 6, such as an integer from 1 to 6). The C 1－6 alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups can be substituted with one or more substituents selected from, for example, a fluorine atom, C 1－6 alkyl, C 2－6 alkenyl, and C 2－6 alkynyl, but is preferably unsubstituted.

[0457] In a preferred embodiment, Z 3 is C 1－6 alkylene or -(CH 2 ) z7” -phenylene-(CH 2 ) z8” -, preferably -phenylene-(CH 2 ) z8” -. When Z 3 is such a group, the light tolerance, especially the ultraviolet tolerance, can be further improved.

[0458] In another preferred embodiment, the above Z 3 is C 1－3 alkylene. In one embodiment, Z 3 can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 3 can be -CH 2 CH 2 -.

[0459] R 34 are each independently a hydroxyl group or a hydrolyzable group.

[0460] R 34 are preferably each independently a hydrolyzable group.

[0461] R 35 is independently a monovalent organic group. The monovalent organic group is a monovalent organic group other than the above hydrolyzable groups.

[0462] In R 35 the monovalent organic group is preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group, and even more preferably a methyl group.

[0463] In the above formula, n2 is independently an integer from 0 to 3 in each (SiR 34 n2 R 35 3－n2 ) unit. Among them, there are at least 2 (SiR 34 n2 R 35 3－n2 ) units in which n2 is 1 to 3 at the terminal part of the formula (S4). In other words, there are at least 2 Si atoms bonded to a hydroxyl group or a hydrolyzable group at the terminal part of the formula (S4).

[0464] n2 is independently preferably an integer from 1 to 3, more preferably 2 to 3, and even more preferably 3 in each (SiR 34 n2 R 35 3－n2 ) unit.

[0465] The above R 33' are independently a hydrogen atom, a hydroxyl group or a monovalent organic group. The monovalent organic group is a monovalent organic group other than the above hydrolyzable groups.

[0466] In the above R 33' the monovalent organic group is preferably a C 1－20 alkyl group or -(C s H 2s ) t1 -(O-C s H 2s ) t2 (wherein s is an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer from 1 to 20, preferably an integer from 2 to 10, and more preferably an integer from 2 to 6), more preferably a C 1－20 alkyl group, and even more preferably a C 1－6 alkyl group, and particularly preferably a methyl group.

[0467] In one embodiment, R 33' is a hydroxyl group.

[0468] In another embodiment, R 33' is a monovalent organic group, preferably a C1－20 alkyl, more preferably C 1－6 alkyl.

[0469] Each of the above q2' is independently an integer from 0 to 3, and each of the above r2' is independently an integer from 0 to 3. Among them, the sum of q2' and r2' is 3 in the (CR 32' q2' R 33' r2' ) unit.

[0470] q2' is preferably an integer from 1 to 3, more preferably 2 to 3, and further preferably 3, independently in each (CR 32' q2' R 33' r2' ) unit.

[0471] R 32 is independently -Z 3 -SiR 34 n2 R 35 3－n2 . The meaning of this -Z 3 -SiR 34 n2 R 35 3－n2 is the same as that described in the above R 32' .

[0472] R 33 is independently a hydrogen atom, a hydroxyl group or a monovalent organic group. This monovalent organic group is a monovalent organic group other than the above hydrolyzable groups.

[0473] In R 33 , the monovalent organic group is preferably C 1－20 alkyl or -(C s H 2s ) t1 -(O-C s H 2s ) t2 -H (wherein s are independently integers from 1 to 6, preferably integers from 2 to 4, t1 is 1 or 0, preferably 0, and t2 is an integer from 1 to 20, preferably an integer from 2 to 10, more preferably an integer from 2 to 6), more preferably C 1－20 alkyl, further preferably C 1－6 alkyl, particularly preferably methyl.

[0474] In one embodiment, R 33 is a hydroxyl group.

[0475] In another embodiment, R 33 is a monovalent organic group, preferably C1－20 alkyl, more preferably C 1－6 alkyl.

[0476] p2 are each independently an integer from 0 to 3, q2 are each independently an integer from 0 to 3, and r2 are each independently an integer from 0 to 3. Among them, the sum of p2, q2, and r2 is 3 in the (CR 31 p2 R 32 q2 R 33 r2 ) unit.

[0477] In one embodiment, p2 is 0.

[0478] In one embodiment, p2 is each independently an integer from 1 to 3, an integer from 2 to 3, or 3 in each (CR 31 p2 R 32 q2 R 33 r2 ) unit. In a preferred embodiment, p2 is 3.

[0479] In one embodiment, q2 is each independently an integer from 1 to 3, preferably an integer from 2 to 3, more preferably 3 in each (CR 31 p2 R 32 q2 R 33 r2 ) unit.

[0480] In one embodiment, p2 is 0, and q2 is each independently an integer from 1 to 3, preferably an integer from 2 to 3, further preferably 3 in each (CR 31 p2 R 32 q2 R 33 r2 ) unit.

[0481] The above R e1 are each independently -Z 3 -SiR 34 n2 R 35 3－n2 . The meaning of this -Z 3 -SiR 34 n2 R 35 3－n2 is the same as that described in the above R 32' .

[0482] The above R f1Each is independently a hydrogen atom, a hydroxyl group, or a monovalent organic group. The monovalent organic group is a monovalent organic group other than the above hydrolyzable groups.

[0483] In the above R f1 Among them, the monovalent organic group is preferably a C 1－20 alkyl group or -(C s H 2s ) t1 -(O-C s H 2s ) t2 -H (wherein s are each independently an integer from 1 to 6, preferably an integer from 2 to 4, t1 is 1 or 0, preferably 0, and t2 is an integer from 1 to 20, preferably an integer from 2 to 10, more preferably an integer from 2 to 6), more preferably a C 1－20 alkyl group, still more preferably a C 1－6 alkyl group, particularly preferably a methyl group.

[0484] In one embodiment, R f1 is a hydroxyl group.

[0485] In another embodiment, R f1 is a monovalent organic group, preferably a C 1－20 alkyl group, more preferably a C 1－6 alkyl group.

[0486] The above k2s are each independently an integer from 0 to 3, the l2s are each independently an integer from 0 to 3, and the m2s are each independently an integer from 0 to 3. Among them, the sum of k2, l2, and m2 is 3 in the (CR d1 k2 R e1 l2 R f1 m2 ) unit.

[0487] In one embodiment, n2 is 1 to 3, preferably 2 or 3, more preferably 3, and two or more, for example, 2 to 27, preferably 2 to 9, more preferably 2 to 6, still more preferably 2 to 3, particularly preferably 3, of the (SiR 34 n2 R 35 3－n2 ) units are present at each terminal portion of the formula (S4).

[0488] In a preferred embodiment, when R 32' is present in the formula (S4), in at least one, preferably all, of the R 32' , n2 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0489] In a preferred embodiment, when R 32In the case of at least 1, preferably all R 32 In 32 , n2 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0490] In a preferred embodiment, when there is R in formula (S4) e1 In the case of at least 1, preferably all R a1 In a1 , n2 is an integer from 1 to 3, preferably 2 or 3, more preferably 3.

[0491] In a preferred embodiment, in formula (S4), k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.

[0492] The above R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3－n1 、-Z 4 -SiR a1 k1 R b1 l1 R c1 m1 、-Z 4 -CR d1 k2 R e1 l2 R f1 m2 。Among them, the meanings of R 11 、R 12 、R a1 、R b2 、R c1 、R d1 、R e1 、R f1 、n1, k1, l1, m1, k2, l2 and m2 are as defined above.

[0493] In a preferred embodiment, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3－n1 。

[0494] The above Z 4 are each independently a single bond, an oxygen atom or a divalent organic group. Among them, the right side of the structure denoted as Z 4 is bonded to (SiR 11 n1 R 123－n1 ) Bonding.

[0495] In one embodiment, Z 4 is an oxygen atom.

[0496] In one embodiment, Z 4 is a divalent organic group.

[0497] In a preferred embodiment, Z 4 does not contain a siloxane bond.

[0498] The above Z 4 is preferably C 1－6 alkylene, -(CH 2 ) z5” O-(CH 2 ) z6” -(wherein, z5” is an integer from 0 to 6, such as an integer from 1 to 6, and z6” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z7” -phenylene-(CH 2 ) z8” -(wherein, z7” is an integer from 0 to 6, such as an integer from 1 to 6, and z8” is an integer from 0 to 6, such as an integer from 1 to 6). The C 1－6 alkylene can be straight-chain or branched-chain, preferably straight-chain. These groups may be substituted with one or more substituents selected from, for example, a fluorine atom, C 1－6 alkyl, C 2－6 alkenyl, and C 2－6 alkynyl, but are preferably unsubstituted.

[0499] In a preferred embodiment, Z 4 is C 1－6 alkylene or -(CH 2 ) z7” -phenylene-(CH 2 ) z8” -, preferably -phenylene-(CH 2 ) z8” -. In the case where Z 4 is such a group, the light resistance, especially the ultraviolet resistance, can be further improved.

[0500] In another preferred embodiment, the above Z 4 is C 1－3 alkylene. In one embodiment, Z 4 can be -CH 2 CH 2 CH 2 -. In another embodiment, Z 4 can be -CH 2 CH2 -。

[0501] In a preferred embodiment, the formulas (S1), (S2), (S3), (S4) and (S5) do not contain a siloxane bond.

[0502] In one embodiment, R Si is a group represented by formula (S3), (S4) or (S5).

[0503] In one embodiment, R Si is a group represented by formula (S3) or (S4).

[0504] In one embodiment, R Si is a group represented by formula (S4) or (S5).

[0505] In one embodiment, R Si is a group represented by formula (S1). In a preferred embodiment, formula (S1) is a group represented by formula (S1-b). In a preferred embodiment, in the formula, R 13 is a hydrogen atom, X 11 is a single bond or -R 28 -O x -R 29 -(wherein, R 28 and R 29 are each independently a single bond or C 1－20 alkylene, x is 0 or 1), and n1 is 1 to 3, preferably 2 to 3, more preferably 3.

[0506] In one embodiment, R Si is a group represented by formula (S2). In a preferred embodiment, formula (S2) is -SiR 11 2 R 12 or -SiR 11 3 .

[0507] In one embodiment, R Si is a group represented by formula (S3). In a preferred embodiment, formula (S3) is -SiR a1 2 R c1 or -SiR a1 3 , R a1 is -Z 1 -SiR 22 q1 R 23 r1 , Z 1 is C 1－6 alkylene, -(CH 2 ) z1 -O-(CH2 ) z2 -(wherein, z1 is an integer from 0 to 6, such as an integer from 1 to 6, and z2 is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z3 -phenylene-(CH 2 ) z4 -(wherein, z3 is an integer from 0 to 6, such as an integer from 1 to 6, and z4 is an integer from 0 to 6, such as an integer from 1 to 6), preferably C 1－6 alkylene, and q1 is from 1 to 3, preferably from 2 to 3, and more preferably 3.

[0508] In one embodiment, R Si is a group represented by formula (S4). In a preferred embodiment, formula (S4) is -CR e1 2 R f1 or -CR e1 3 , R e1 is -Z 3 -SiR 34 n2 R 35 3－n2 , Z 3 is C 1－6 alkylene, -(CH 2 ) z5” O-(CH 2 ) z6” -(wherein, z5” is an integer from 0 to 6, such as an integer from 1 to 6, and z6” is an integer from 0 to 6, such as an integer from 1 to 6) or -(CH 2 ) z7” -phenylene-(CH 2 ) z8” -(wherein, z7” is an integer from 0 to 6, such as an integer from 1 to 6, and z8” is an integer from 0 to 6, such as an integer from 1 to 6), preferably C 1－6 alkylene, and n2 is from 1 to 3, preferably from 2 to 3, and more preferably 3.

[0509] In one embodiment, R Si is a group represented by formula (S5). In a preferred embodiment, R g1 and R h1 are -Z 4 -SiR 11 n1 R 12 3－n1 , Z 4 is C 1－6 alkylene, -(CH 2 ) z5” -O-(CH2 ) z6” -(wherein, z5” is an integer of 0 to 6, such as an integer of 1 to 6, and z6” is an integer of 0 to 6, such as an integer of 1 to 6) or -(CH 2 ) z7” -phenylene-(CH 2 ) z8” -(wherein, z7” is an integer of 0 to 6, such as an integer of 1 to 6, and z8” is an integer of 0 to 6, such as an integer of 1 to 6), preferably C 1－6 alkylene, and n1 is 1 to 3, preferably 2 to 3, more preferably 3.

[0510] The fluorine atom-containing silane compound represented by the above formula (1) may have a number-average molecular weight of 1×10 2 to 1×10 5 , but there is no particular limitation. From the viewpoint of frictional durability, it is preferred that the fluorine atom-containing silane compound represented by the above formula (1) has a number-average molecular weight of preferably 100 to 30,000, more preferably 100 to 10,000. Among them, the “number-average molecular weight” is a value measured by 1 H-NMR.

[0511] As the fluorine atom-containing silane compound represented by the formula (1), for example, compounds having the following structures can be cited.

[0512]

[0513] A 1 γ11 A 2 γ12 C-R k61 -R Si (T6)

[0514] A 1 γ11 A 2 γ12 C-R k71 -O-R k72 -R Si (T7)

[0515] A 1 、A 2 、γ11, γ12 have the same meanings as above. Preferably A 1 γ11 A 2 γ12 C- is HF 2 C-.

[0516] R 53 is a hydrogen atom or a monovalent organic group. For example, a hydrogen atom, a methyl group, etc. can be cited.

[0517] R Si has the same meaning as above.

[0518] In formula (T1), A 1 γ11 A 2 γ12 C-R k11 - is equivalent to Rf 1 、-C(=O)NR 53 -R k12 - is equivalent to X A .

[0519] R k11 is a single bond or C 1－9 alkylene, for example, a single bond.

[0520] R k12 is a single bond or C 1－30 alkylene, for example, C 1－10 alkylene.

[0521] In formula (T2), A 1 γ11 A 2 γ12 C-R k21 - is equivalent to Rf 1 -、-C(=O)NR 53 -R k22 - is equivalent to -X A -.

[0522] R k21 is a single bond or C 10－200 alkylene, for example, C 10－30 alkylene.

[0523] R k22 is a single bond or C 1－200 alkylene, for example, C 1－10 alkylene.

[0524] In formula (T3), A 1 γ11 A 2 γ12 C-[(CH 2 ) g1 -SiR s 2 O-(SiR s 2 O) n11 -SiR s 2 -(CH 2 ) g1 - is equivalent to Rf 1 -、-C(=O)NR53 -R k33 - is equivalent to -X A -.

[0525] g1 is independently an integer from 0 to 30 respectively.

[0526] R k33 is a single bond or C 1－200 alkylene, for example C 1－10 alkylene.

[0527] Among them, the total number of carbon atoms and g1 is 0 to 200.

[0528] R s , the meaning of n11 is the same as above.

[0529] In formula (T4), A 1 γ11 A 2 γ12 C-(R k41 ) k41 -(OR k42 ) k42 - is equivalent to Rf 1 , -C(=O)NR 53 -R k43 - is equivalent to X A .

[0530] R k41 and R k42 are a single bond or alkylene.

[0531] k41 is 0 or 1.

[0532] k42 is an integer from 0 to 150.

[0533] Among them, -(R k41 ) k41 -(OR k42 ) k42 - contains an integer number of carbon atoms from 1 to 150.

[0534] R k43 is a single bond or C 1－20 alkylene, for example C 1－10 alkylene.

[0535] R k41 is a single bond or C 1－20 alkylene, such as methylene, ethylene, k41 is 1, R k42 is C 1－6 alkylene, such as ethylene, k42 is an integer from 1 to 50.

[0536] In formula (T5), A 1γ11 A 2 γ12 C−R k51 − equivalent to Rf 1 、−OC(=O)NR 53 −R k52 − equivalent to X A 。

[0537] R k51 is a single bond or C 1－200 alkylene, for example, is a single bond or C 1－10 alkylene.

[0538] R k52 is a single bond or C 1－200 alkylene, for example, is C 10－30 alkylene.

[0539] In formula (T6), A 1 γ11 A 2 γ12 C−R k61 − equivalent to Rf 1 。

[0540] R k61 is C 1－200 alkylene, for example, is C 1－30 alkylene.

[0541] In formula (T7), A 1 γ11 A 2 γ12 C−R k71 −O−R k72 − equivalent to Rf 1 。

[0542] R k71 and R k72 are each independently a single bond or C 1－200 alkylene. Among them, R k71 and R k72 have a total number of carbon atoms of an integer from 0 to 200. For example, R k71 and R k72 are each independently a single bond or C 1－30 alkylene.

[0543] As a specific example of the fluorine atom-containing silane compound represented by formula (1), compounds having the following structures can be cited, for example.

[0544]

[0545] As another specific example of the fluorine atom-containing silane compound represented by the formula (1), for example, compounds having the following structures can be cited. In the following formulas, n is preferably 1 or more, more preferably 4 or more, and particularly preferably 8 or more. Also, n is preferably 50 or less, more preferably 40 or less, and particularly preferably 30 or less. Further, n is preferably from 1 to 50, more preferably from 4 to 40, and particularly preferably from 8 to 30.

[0546]

[0547] As other specific examples of the fluorine atom-containing silane compound represented by the formula (1), for example, compounds having the following structures can be cited. In the following formulas, n is preferably 1 or more, more preferably 4 or more, and particularly preferably 8 or more. Also, n is preferably 50 or less, more preferably 40 or less, and particularly preferably 30 or less. Further, n is preferably from 1 to 50, more preferably from 4 to 40, and particularly preferably from 8 to 30.

[0548]

[0549] As other specific examples of the fluorine atom-containing silane compound represented by the formula (1), for example, compounds having the following structures can be cited. In the following formulas, n is preferably 0 or more, more preferably 3 or more, and particularly preferably 8 or more. Also, n is preferably 50 or less, more preferably 40 or less, and particularly preferably 30 or less. Further, n is preferably from 0 to 50, more preferably from 3 to 40, and particularly preferably from 8 to 30.

[0550]

[0551] [Manufacturing method]

[0552] The manufacturing method of the fluorine atom-containing silane compound of the present invention will be described below. However, the manufacturing method of the fluorine atom-containing silane compound of the present invention is not limited to the following method. Further, as A 1 γ11 A 2 γ12 C - sometimes uses HF 2 C - or H 2 FC -, but is not particularly limited to this structure.

[0553] As a group containing A 1 γ11 A 2 γ12 C -, for example, a group containing HF 2 C -(difluoromethyl) or H 2 FC -(monofluoromethyl), the manufacturing method of which is to use a compound having HF 2 C - or H2 Method for Deriving Compounds of FC− and Method for Fluorinating and Introducing Functional Groups

[0554] (Manufacturing Method 1)

[0555] This manufacturing method includes the following steps.

[0556] Step (I): Using compound (11): A 1 γ11 A 2 γ12 C−R j11 −NH 2 As a raw material, mix it with isocyanate compound (12): O═C═N−R j12 −R Si to produce a fluorine atom-containing silane compound (13).

[0557]

[0558] R j11 is a single bond or an alkylene group, for example, is C 1－30 alkylene group, specifically methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, icosylene.

[0559] As compound (11), specifically, difluoromethylamine, difluoroethylamine, difluoropropylamine, monofluoromethylamine, monofluoroethylamine, monofluoropropylamine, etc. can be cited.

[0560] R j12 is a single bond or an alkylene group, for example, is an alkylene group, specifically C 1－30 alkylene group.

[0561] As isocyanate compound (12), specifically, 3-(trimethylsilyl)propyl isocyanate, etc. can be cited.

[0562] R Si has the same meaning as above. For example, R Si is represented by formula (S2).

[0563] The above reaction can be carried out in a solvent. The above solvent is preferably a substance that can dissolve compound (11) to compound (13). The above solvent can be used alone or in combination of two or more.

[0564] The above solvent is, for example, a non-fluorinated solvent or a fluorinated solvent.

[0565] As non-fluorine solvents, for example, sulfur atom-containing solvents, amide solvents, ester solvents, ketone solvents, ether solvents, halogen-containing solvents, and hydrocarbon solvents can be cited.

[0566] As sulfur atom-containing solvents, dimethyl sulfoxide, sulfolane, dimethyl sulfide, carbon disulfide, etc. can be cited.

[0567] As amide solvents, N-methylpyrrolidone, N,N-dimethylformamide, dimethylacetamide, hexamethylphosphoric triamide, etc. can be cited.

[0568] As ester solvents, methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, etc. can be cited.

[0569] As ketone solvents, acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methylamino ketone, 2-heptanone, etc. can be cited.

[0570] As ether solvents, diethyl ether, tetrahydrofuran, cyclopentyl methyl ether, ethylene glycol, monoglyme, diglyme, etc. can be cited.

[0571] As halogen-containing solvents, dichloromethane, chloroform, etc. can be cited.

[0572] As hydrocarbon solvents, pentane, hexane, heptane, benzene, toluene, etc. can be cited.

[0573] Fluorine solvents are solvents containing one or more fluorine atoms. As fluorine solvents, for example, compounds in which at least one hydrogen atom of hydrocarbons such as hydrofluorocarbons, hydrochlorofluorocarbons, and perfluorocarbons is replaced by a fluorine atom; hydrofluoroethers, etc. Here, hydrocarbons refer to compounds containing only carbon atoms and hydrogen atoms.

[0574] As hydrofluorocarbons, for example, bis(trifluoromethyl)benzene, specifically 1,3-bis(trifluoromethyl)benzene (m-XHF), 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane, C 6 F 13 CH 2 CH 3 (for example, ASAHIKLIN (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (for example, ZEORORA (registered trademark) H manufactured by Nippon Zeon Co., Ltd.), etc.

[0575] As the hydrochlorofluorocarbons, for example, HCFC-225 (e.g., ASAHIKLIN AK-225 manufactured by AGC Inc.), HFO-1233zd(Z) (e.g., CELEFIN 1233Z manufactured by Central Glass Co., Ltd.) etc. can be cited.

[0576] As the perfluorocarbons, for example, perfluorohexane, perfluoromethylcyclohexane, perfluoro-1,3-dimethylcyclohexane, perfluorobenzene etc. can be cited.

[0577] As the hydrofluoroethers, for example, perfluoropropyl methyl ether (C 3 F 7 OCH 3 )(e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C 4 F 9 OCH 3 )(e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C 4 F 9 OC 2 H 5 )(e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C 2 F 5 CF(OCH 3 )C 3 F 7 )(e.g., Novec (trademark) 7300 manufactured by Sumitomo 3M Limited) etc. of alkyl perfluoroalkyl ethers (the perfluoroalkyl and alkyl can be linear or branched); CF 3 CH 2 OCF 2 CHF 2 (e.g., ASAHIKLIN (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.) etc.

[0578] Among the solvents listed above, the fluorine-based solvents are preferably m-XHF, HFE7100, HFE7200, HFE7300, AC-6000, perfluorohexane and perfluorobenzene.

[0579] The solvent is preferably at least one selected from diethyl ether, tetrahydrofuran, cyclopentyl methyl ether, ethylene glycol, dichloromethane, chloroform, benzene, toluene and 1,3-bis(trifluoromethyl)benzene, and more preferably at least one selected from dichloromethane, chloroform, toluene and 1,3-bis(trifluoromethyl)benzene.

[0580] The above reaction temperature is not particularly limited. For example, the reaction temperature can be 0 to 100 °C, 0 to 50 °C, 0 to 30 °C.

[0581] (Production method 2)

[0582] In this production method, an amide compound containing an olefin (-CH=CH 2 ) is produced by reacting an amine compound containing an olefin with a compound containing a carbonyl group (-C(=O)-), and the fluorine atom-containing silane compound of the present invention can be synthesized from the amide compound containing an olefin. For example, by reacting an amide compound having an olefin at the terminal with the following formula: HSiR j27 m3 R j28 3－m3 shown compound, a fluorine atom-containing silane compound can be obtained.

[0583] [In the formula,

[0584] R j27 are each independently a hydroxyl group or a hydrolyzable group,

[0585] R j28 are each independently a monovalent organic group,

[0586] m3 is 1 to 3.]

[0587] The above monovalent organic group does not include a hydrolyzable group.

[0588] The amine compound containing an olefin is a compound having H 2 N- and -CH=CH 2 , for example, H 2 N(CH 2 ) x31 Q((CH 2 ) x32 CH=CH 2 ) x33 R x3 x34 (wherein, x31 and x32 are each an integer from 0 to 6, x33 is an integer of 1 or more, x34 is an integer of 0 or more, the sum of x33 and x34 is the valence of Q - 1, Q is N, Si or C, and R x3 is a hydrogen atom, a hydroxyl group or a monovalent organic group).

[0589] As the amine compound containing an olefin, for example, allylamine, diallylamine, 2-allylpent-4-en-1-amine (H 2 NCH 2 CH(CH 2 CH=CH 2 ) 2 ), 2,2-diallylpent-4-en-1-amine (H 2 N-CH 2 C(CH2 CH=CH 2 ) 3 ) etc.

[0590] The carbonyl-containing compound is a compound containing A 1 γ11 A 2 γ12 a C− and a C(=O) group. As the carbonyl-containing compound, compounds obtained by the following synthesis methods 1, 3 to 6 or the compound represented by formula (21) can be mentioned.

[0591]

[0592] In formula (21), R j13 is a single bond or an alkylene group, for example, a single bond; R j14 is a hydroxyl group, a fluorine atom, a chlorine atom or -O-lower alkyl (i.e., an alkoxy group), for example, a hydrogen atom, a methoxy group, an ethoxy group, specifically a hydrogen atom or a methoxy group.

[0593] As the compound of formula (21), specifically, difluoroacetic acid, methyl difluoroacetate, ethyl difluoroacetate, monofluoroacetic acid, methyl monofluoroacetate, ethyl monofluoroacetate, etc. can be mentioned.

[0594] When the carbonyl-containing compound has an acyl chloride (C(=O)Cl), an olefin-containing amide compound can be obtained by reacting with a trialkylamine. As the trialkylamine, for example, triethylamine etc. can be mentioned.

[0595] When the carbonyl-containing compound has a carboxylic acid, an olefin-containing amide compound can be obtained by reacting with a condensing agent.

[0596] As a condensing agent, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl), N,N'-dicyclohexylcarbodiimide (DCC), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate (HBTU), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide tetrafluoroborate (TATU), 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU), O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium hexafluorophosphate (HOTU), 1H-benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP), 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), tripyrrolidinophosphonium bromide hexafluorophosphate (PyBroP), diphenylphosphoryl azide (DPPA), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium hydrochloride (DMT-MM), 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) are preferably used, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole are more preferably used. In addition, 4-dimethylaminopyridine (DMAP) etc. can be added as a catalyst.

[0597] When the carbonyl-containing compound has an ester, an olefin-containing amide compound can be obtained by carrying out the reaction in the presence of a base.

[0598] As the base, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 1,2,4-triazole, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), sodium methoxide, sodium tert-butoxide are preferably used, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene is more preferably used.

[0599] The above reaction temperature is not particularly limited. For example, the reaction temperature can be 0 to 150 °C, 0 to 100 °C, 0 to 50 °C.

[0600] The solvent can be the same substance as that used in Production Method 1. Preferred are acetonitrile, dichloromethane, chloroform, toluene, diethyl ether, and tetrahydrofuran. Additionally, the reaction can also be carried out under solvent-free conditions.

[0601] (Production Method 3)

[0602] In this production method, an olefin group-containing compound is used as a raw material to produce a fluorine atom-containing silane compound.

[0603] The olefin group-containing compound has A 1 γ11 A 2 γ12 C- and an olefin group (-CH=CH 2 ). Compounds obtained by the following Synthesis Methods 2 to 6 can be cited as the olefin group-containing compound.

[0604] For example, a compound of the formula: A 1 γ11 A 2 γ12 C-R j22 -R Si (R j22 is a divalent organic group and is equivalent to -R j21 -CH 2 CH 2 -, and the meaning of R Si is the same as above) can be produced by the following method.

[0605] This method includes:

[0606] Reacting HSiM 3 (M is independently a halogen atom or a C 1－6 alkoxy group) with an olefin group, and then reacting the resulting compound with a compound represented by the formula: Hal-J-CH=CH 2 (in the formula, J represents Mg, Cu, Pd, or Zn, and Hal represents a halogen atom), and, if necessary, a compound represented by the formula: R c1 h' L (in the formula, the meaning of R c1 is the same as above, L represents a group capable of bonding to R c1 , and h' is an integer from 1 to 3) to obtain the following compound:

[0607] A 1 γ11 A 2 γ12 C-R j21 -CH 2 CH 2 -SiR c1 m1 (CH=CH2 ) k’

[0608] (-R j21 -CH 2 CH 2 - is equivalent to X B , for example, -R j21 -CH 2 CH 2 - is an alkylene group, for example, C 1－30 alkylene group, specifically C 10－25 alkylene group, the meaning of m1 is the same as above, the sum of m1 and k' is 3); and

[0609] reacting the above compound with HSiM 3 (wherein, M is independently a halogen atom or C 1－6 alkoxy group), according to need, a compound of the formula: R 23 i' L' (wherein, the meaning of R 23 is the same as above, L' represents a group capable of bonding to R 23 , and i' is an integer from 1 to 3) and, according to need, a compound of the formula: R 24 j' L'' (wherein, the meaning of R 24 is the same as above, L'' represents a group capable of bonding to R 24 , and j' is an integer from 1 to 3) is shown in the step of the reaction of the compound.

[0610] Moreover, the above description can also be applied to other olefin group-containing compounds.

[0611] (Manufacturing method 4)

[0612] In this manufacturing method, a fluorine atom-containing silane compound is manufactured by reacting an amine-containing silane compound with a carbonyl group-containing compound.

[0613] The carbonyl group-containing compound is a compound containing A 1 γ11 A 2 γ12 C- and C(=O). As the carbonyl group-containing compound, compounds obtained by the following synthesis methods 1, 3 to 6 or the compound represented by the formula (21) can be cited.

[0614]

[0615] For example, A 1 γ11 A 2 γ12 C- is HF 2 C-. R j13 and Rj14 It has the same meaning as above.

[0616] The amine-containing silane compound has an H 2 N-group and an R Si -group. As the amine-containing silane compound, for example, H 2 N-R j23 -R Si can be cited. Specifically, aminopropyltrimethoxysilane can be cited. The above R j23 is an alkylene group, for example, a C 1－4 alkylene group, specifically a methylene group, an ethylene group, a propylene group; the meaning of the above R Si is the same as above. For example, R Si is represented by the formula (S2).

[0617] The fluorine atom-containing silane compound is, for example, A 1 γ11 A 2 γ12 C-R j24 -C(=O)NHR j23 -R Si . The above A 1 γ11 A 2 γ 12 C-R j24 -corresponds to Rf 1 -. R j24 is an alkylene group, for example, a C 1－4 alkylene group, specifically a methylene group, an ethylene group, a propylene group.

[0618] The reaction temperature is preferably 0°C to 150°C, more preferably 20°C to 100°C.

[0619] The solvent can be the same substance as in Production Method 1, and toluene, dichloromethane, chloroform, methanol, and ethanol are preferably used.

[0620] (Production Method 5)

[0621] In this production method, a fluorine atom-containing silane compound is produced by reacting an olefin group-containing compound.

[0622] Specifically, by reacting an olefin group-containing compound with the following formula: HSiR j25 m3 R j26 3－m3 [wherein, R j25 are each independently a hydroxyl group or a hydrolyzable group, R j26 are each independently a monovalent organic group, and m3 is 1 to 3] shown compound, a fluorine atom-containing silane compound can be obtained.

[0623] Moreover, the above description can also be applied to other olefin group-containing compounds.

[0624] The olefin group-containing compound has A 1 γ11 A 2 γ12 a compound having a C− and an olefin group. As the olefin group-containing compound, compounds obtained by the following synthesis methods 2 to 6 can be cited.

[0625] The reaction temperature is preferably from -20°C to 150°C, more preferably from 0°C to 100°C.

[0626] As the solvent, the same substances as those in Production Method 1 can be used, and toluene, dichloromethane, chloroform, methanol, ethanol, diethyl ether, cyclopentyl methyl ether can be preferably used.

[0627] (Production Method 1)

[0628] In this method, a compound (31) having a group containing A 1 γ11 A 2 γ12 C− and a hydroxyl group: A 1 γ11 A 2 γ 12 C−R j33 −OH is used as a raw material to synthesize a carbonyl group-containing compound.

[0629] The group containing A 1 γ11 A 2 γ12 C−, for example, contains HF 2 C−.

[0630] R j33 is an alkylene group, for example, is C 1－30 alkylene group.

[0631] Specific examples of the compound (31) include difluoroethanol, difluoropropanol, difluorobutanol, monofluoroethanol, monofluoropropanol, monofluorobutanol, etc.

[0632] According to a conventional method, the hydroxyl group of the compound (31) is converted to -OTf (Tf is trifluoromethylsulfonyl), whereby the compound (32): A 1 γ11 A 2 γ12 C−R j33 −OTf can be obtained.

[0633] This method includes the following step (I').

[0634] (I'): Mix the above compound (32) with a compound (33) having a reactive group to obtain a carbonyl-containing compound (34).

[0635]

[0636] Here, examples of the reactive group include a hydroxyl group, a carboxyl group, Cl, F, and an ester group obtained by esterifying a carboxyl group.

[0637] Specific examples of the compound (33) having a reactive group include compounds having a hydroxyl group at the end such as tert-butyl 9-hydroxy-4,7-dioxanonanoate, tert-butyl 12-hydroxy-4,7,10-trioxadodecanoate, tert-butyl 1-hydroxy-3,6,9,12-tetraoxapentadecane-15-carboxylate; compounds having a carboxyl group at the end such as 10-hydroxydecanoic acid, 11-hydroxyundecanoic acid, 12-hydroxydodecanoic acid, 13-hydroxytridecanoic acid, 14-hydroxytetradecanoic acid, 15-hydroxypentadecanoic acid, 16-hydroxyhexadecanoic acid, 17-hydroxyheptadecanoic acid, 18-hydroxyoctadecanoic acid, 19-hydroxynonadecanoic acid, 20-hydroxyicosanoic acid, 21-hydroxyheneicosanoic acid, 22-hydroxydocosanoic acid, 23-hydroxytricosanoic acid, 24-hydroxytricosaic acid, 25-hydroxypentacosanoic acid, 30-hydroxytriacontanoic acid, and their methyl esters, acyl chlorides, etc.

[0638] R j31 is a divalent organic group, for example, a group having a polyether group or an alkylene group, specifically, -(R j35 O) n -R j36 - group or C 1－30 alkylene group.

[0639] The above R j35 is C 1－3 alkylene group, for example, ethylene group, and the above R j36 is C 1－3 alkylene group, for example, ethylene group.

[0640] The above n is an integer of 2 to 150, for example, an integer of 2 to 50.

[0641] R j32 is a lower alkyl group, for example, methyl group, ethyl group, propyl group, butyl group, tert-butyl group, specifically, methyl group, tert-butyl group.

[0642] The above reaction temperature is not particularly limited. For example, the reaction can be carried out at a reaction temperature of -80 to 200 °C, for example, -50 to 100 °C, specifically, -20 to 50 °C.

[0643] The same substances as those in Production Method 1 can be used as the solvent.

[0644] (Synthesis Method 2)

[0645] In this method, a compound (31) having a group containing A 1 γ11 A 2 γ12 C- and a hydroxyl group: A 1 γ11 A 2 γ 12 C-R j33 -OH is used as a raw material to synthesize an olefin-containing compound. The meanings of the respective symbols are the same as above.

[0646] According to a conventional method, the hydroxyl group of the compound (31) is converted to -OTf (Tf is trifluoromethylsulfonyl) to produce the compound (32): A 1 γ11 A 2 γ12 C-R j33 -OTf.

[0647] This method includes the following step (I').

[0648] (I'): The above-mentioned compound (32) is mixed with a compound (35) having a reactive group: HO-R j31 -CH=CH 2 to obtain an olefin-containing compound (36).

[0649]

[0650] R j33 and R j31 have the same meanings as above.

[0651] The significance of the reaction temperature and the solvent is the same as in Manufacturing Method 2.

[0652] (Synthesis Method 3)

[0653] In this method, a compound (41) in which a group containing A 1 γ11 A 2 γ12 C- is bonded to a trialkylsilyl group: A 1 γ11 A 2 γ12 C-SiR j40 3 is used as a raw material. A group containing A 1 γ11 A 2 γ12 C- for example contains HF 2 C-.

[0654] R j40 are each independently a lower alkyl group, such as C 1－3 alkyl group.

[0655] As the compound (41), for example, difluoromethyltrimethylsilane etc. can be cited.

[0656] React the compound (41) with the compound (42) having a leaving group: X-R j41 -Z in the presence of a metal catalyst to obtain A 1 γ11 A 2 γ12 C-R j41 -Z.

[0657] R j41 is an alkylene group, such as C 1－30 alkylene group, specifically C 10－25 alkylene group.

[0658] Z is a reactive group. For example, Z is -C(=O)OR j42 (R j42 such as a hydrogen atom, a methyl group) or -CH=CH 2 . That is, through the above reaction, a carbonyl group-containing compound (43) or an olefin-containing compound (43') at the terminal is synthesized.

[0659] X is Cl, Br, I, OTs (where Ts is p-toluenesulfonyl), OMs (where Ms is methanesulfonyl), and preferably Br, I.

[0660] The above metal catalyst is at least 1 kind selected from Pd, Cu, Ni, Pt and Ag, and preferably at least 1 kind selected from Pd and Cu. This metal catalyst can be a metal element, a metal salt, or a coordination compound having a ligand.

[0661] In one mode, a metal element is used as the metal catalyst.

[0662] In one mode, a metal salt is used as the metal catalyst. Preferably, it is copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(I) iodide, copper(II) iodide, silver(I) chloride, silver(I) bromide, silver(I) iodide, and more preferably copper(I) chloride, copper(I) bromide, copper(I) iodide.

[0663] In one mode, a coordination compound having a ligand is used as the metal catalyst. This ligand is preferably a ligand containing a phosphorus atom, a ligand containing an olefin group, or a ligand containing a nitrogen atom.

[0664] As the above ligand, for example, triphenylphosphine (i.e., PPh3 ) tris(tert-butyl)phosphine (i.e., P(t-Bu) 3 ) tri(n-butyl)phosphine (i.e., P(n-Bu) 3 ) tri(o-tolyl)phosphine (i.e., P(o-Tol) 3 ), (C 6 F 5 ) 3 P (i.e., Tpfpp), (C 6 F 5 ) 2 PCH 2 CH 2 P(C 5 F 5 ) 2 )(i.e., Dfppe), 1,2-bis(diphenylphosphino)ethane (i.e., dppe), 1,3-bis(diphenylphosphino)propane (i.e., dppp), 1,1'-bis(diphenylphosphino)ferrocene (i.e., dppf), (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (i.e., (S)-BINAP), 1,5-cyclooctadiene (i.e., COD), bipyridine (i.e., bpy), phenanthroline (i.e., phen) or a salt thereof.

[0665] As the above metal catalyst, for example, Pd metal, Pd(dba) 2 , Pd(dba) 3 , Cu metal, copper(I) chloride, copper(I) bromide, copper(I) iodide, etc. are exemplified. Preferably, the above metal catalyst is Pd(dba) 2 , Pd(dba) 3 or copper(I) iodide. Herein, "dba" means dibenzylideneacetone.

[0666] Relative to 1 mole of the compound (42) having a leaving group, the metal catalyst may contain, for example, 0.01 mole or more, 0.1 mole or more, 0.2 mole or more, 0.5 mole or more, 1 mole or more, 2 moles or more, 3 moles or more. Relative to 1 mole of the above compound (42), the metal catalyst may contain, for example, 10 moles or less, 8 moles or less. Relative to 1 mole of the above compound (42), the metal catalyst may contain 0.01 to 10 moles, 0.05 to 10 moles, 1 to 10 moles, 2 to 10 moles or 3 to 8 moles.

[0667] In one embodiment, when the metal catalyst is copper(I) iodide, relative to the compound (42), the metal catalyst may contain 0.1 to 10 moles or 0.5 to 2 moles.

[0668] In one embodiment, when the metal catalyst is Pd(dba) 2In the case of , the metal catalyst may be contained in an amount of 0.01 to 1 mol or 0.05 to 0.5 mol relative to compound (42).

[0669] The metal catalyst may be a catalyst that introduces a ligand into a precursor of the metal catalyst during the reaction. Examples of the precursor of the metal catalyst include substances having at least one selected from Pd, Pt, Cu, Ag, Zn and Mg. Examples of the ligand include triphenylphosphine, tri-tert-butylphosphine, tri-n-butylphosphine, tri-o-tolylphosphine, (C 6 F 5 ) 3 P、(C 6 F 5 ) 2 PCH 2 CH 2 P(C 5 F 5 ) 2 ), 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,1'-bis(diphenylphosphino)ferrocene, (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,5-cyclooctadiene, bipyridine, phenanthroline, etc.

[0670] The reaction temperature is not particularly limited and may be, for example, 0 to 200°C, 0 to 150°C, or 20 to 100°C.

[0671] The solvent that can be used is the same as that in Production Method 1. Preferably, dimethyl sulfoxide, sulfolane, N-methylpyrrolidone, N,N-dimethylformamide, or dimethylacetamide is used.

[0672] (Synthesis Method 4)

[0673] In this method, a 1 γ11 A 2 γ12 A compound (51) in which a C- group is bonded to a trialkylsilyl group is used as a raw material. 1 γ11 A 2 γ12 C - for example BrF 2 C-. Examples of the above-mentioned compound include bromofluoromethyltrimethylsilane (BrF 2 C-TMS).

[0674] By reacting the compound (51) with a nucleophile (52) having a heteroatom: Nu—H (wherein Nu is a nucleophile, for example, R j50 O-、R j50 S-、R j502 N-; R j50 are each independently C 1－3 alkyl) reacts in the presence of a base to be derivatized into a compound having a carbonyl group at the terminal (carbonyl-containing compound) or a compound having an olefin at the terminal (olefin group-containing compound).

[0675] Examples of the base include organic amines such as ammonia, sodium hydroxide, potassium hydroxide, triethylamine, and diethylamine. The base can be used in the form of an aqueous solution dissolved in water. As the base, sodium hydroxide and potassium hydroxide are preferably used.

[0676] The above reaction temperature is not particularly limited. For example, the reaction temperature can be -20 to 100 °C, -10 to 80 °C, or -10 to 50 °C.

[0677] The same substances as those in Production Method 1 can be used as the solvent. The solvent is preferably acetonitrile, dichloromethane, chloroform, toluene, diethyl ether, tetrahydrofuran, dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, or dimethylacetamide.

[0678] (Synthesis Method 5)

[0679] In this method, a compound having a formyl group is fluorinated to form HF 2 C-, to synthesize the formula: HCF 2 -R j60 -A j61 .

[0680] [In the formula:

[0681] The above R j60 is a divalent organic group, for example, C 1－20 alkylene;

[0682] The above A j61 is -COOH, -COOR j62 , -COCl, -CH=CH 2 ;

[0683] The above R j62 is a lower alkyl group, for example, C 1－3 alkyl.]

[0684] Through the above reaction, a carbonyl group-containing compound or an olefin group-containing compound can be synthesized.

[0685] Examples of the compound having a formyl group include H(C=O)-R j60 -A j61 .

[0686] Examples of the above-mentioned fluorinating agents include sulfur trifluoride diethylamine (DAST), bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor (registered trademark)), morpholine sulfur trifluoride (MOST), 2,2-difluoro-1,3-dimethylimidazolidine (DFI), 2-chloro-N,N-diethyl-1,1,2-trifluoroethylamine (Yarovenko reagent), N,N-diethyl-α,α-difluoro-3-methylbenzylamine (DFMBA), (diethylamino)difluorosulfonium tetrafluoroborate (XtalFluor-E (registered trademark)), difluoro-4-morpholinylsulfonium tetrafluoroborate (XtalFluor-M (registered trademark)), and the like.

[0687] In one embodiment, DAST is preferably used as the fluorinating agent. By using DAST, the difluoromethylation reaction of the formyl group can be selectively carried out.

[0688] In one embodiment, Deoxofluor or MOST is preferably used as the fluorinating agent. By using Deoxofluor or MOST, the difluoromethylation reaction under heating conditions can be carried out.

[0689] The above reaction temperature is not particularly limited. For example, the reaction temperature can be -20 to 200 °C, -10 to 150 °C, or 0 to 10 °C.

[0690] The same substances as those in Production Method 1 can be used as the solvent. The solvent is preferably acetonitrile, dichloromethane, chloroform, toluene, diethyl ether, or tetrahydrofuran. Moreover, the reaction can be carried out under solvent-free conditions.

[0691] (Synthesis Method 6)

[0692] In this method, an H 2 FC-group or -CFH-group is synthesized by fluorinating a hydroxyl group using a fluorinating agent. For example, by reacting HO-R j60 -A j61 H 2 CF-R j60 -A j61 is synthesized, and by reacting R'-CH(OH)-R j60 -A j61 R'-CFH-R j60 -A j61 is synthesized.

[0693] The above R j60 is a divalent organic group, for example, an alkylene group such as C 1－20 .

[0694] The above A j61 is -COOH, -COOR j62, -COCl, -CH=CH 2 .

[0695] The above R j62 is a lower alkyl group, for example, a C 1－3 alkyl group.

[0696] Through the above reaction, a carbonyl group-containing compound or an olefin group-containing compound can be synthesized.

[0697] As the above fluorinating agent, sulfur tetrafluoride (SF 4 ), N,N-diethylaminosulfur trifluoride (DAST), bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor (registered trademark)), morpholinosulfur trifluoride (MOST), 2,2-difluoro-1,3-dimethylimidazolidine (DFI), 2-chloro-N,N-diethyl-1,1,2-trifluoroethanamine (FAR, Yarovenko reagent), (diethylamino)difluorosulfonium tetrafluoroborate (XtalFluor-E (registered trademark)), difluoro-4-morpholinylsulfonium tetrafluoroborate (XtalFluor-M (registered trademark)), hexafluoropropylene diethylamine, triethylamine trihydrofluoride, triethylamine pentahydrofluoride, iodine pentafluoride pyridinium-hydrogen fluoride coordination compound, N,N'-difluoro-2,2'-bipyridinium bis(tetrafluoroborate), 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (FLUOLEAD(TM)), 2-chloro-1,3-bis(2,6-diisopropylphenyl)-1H-chloroimidazole (PhenoFluor(TM)), etc. can be cited.

[0698] In one embodiment, as the fluorinating agent, triethylamine trihydrofluoride, triethylamine pentahydrofluoride, or iodine pentafluoride pyridinium-hydrogen fluoride coordination compound is preferably used. By using a coordination compound, hydrogen fluoride can be easily handled.

[0699] In one embodiment, DAST is used as the fluorinating agent. By using DAST, the reaction can be carried out at a lower temperature.

[0700] In one embodiment, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (FLUOLEAD(TM)) is preferably used as the fluorinating agent. By using 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (FLUOLEAD(TM)), the operation in air becomes easy.

[0701] The above reaction temperature is not particularly limited. For example, the reaction temperature can be -20 to 200 °C, -10 to 150 °C, or 0 to 10 °C.

[0702] The solvent can be the same substance as that used in Production Method 1. Preferred are acetonitrile, dichloromethane, chloroform, toluene, diethyl ether, and tetrahydrofuran. Also, the reaction can be carried out under solvent-free conditions.

[0703] Moreover, a compound having a monofluoromethyl group or a difluoromethyl group at the terminal can also be produced from a fluoroolefin compound.

[0704] Examples of the fluoroolefin compound include vinyl fluoride, 1,1-difluoroethylene, 1,2-difluoroethylene, trifluoroethylene, 2,3,3-trifluoro-1-propene, 2,3,4,4-tetrafluoro-1-propene, and the like. By carrying out a radical reaction of polymerizing the above-described fluoroolefin compound or adding an alcohol or the like to the fluoroolefin compound, a compound having a monofluoromethyl group or a difluoromethyl group can be obtained.

[0705] [Intermediate]

[0706] The intermediate produced when manufacturing a fluorine atom-containing silane compound will be described.

[0707] Formula (2a):

[0708]

[0709] Rf 1' are each independently A 11 γ11 A 12 γ12 C− or a cyclic structure containing CF≡. The meanings of the respective symbols are the same as above.

[0710] X B2 is a single bond, an oxygen atom, or a divalent organic group, preferably (CH 2 ) c21 (CH 2 ) c22 −O−(CH 2 ) c23 or a divalent polysiloxane group-containing group.

[0711] c21, c22, and c23 are each independently an integer of 0 to 200. Among them, the sum of c22 and c23 is an integer of 0 to 200.

[0712] Rf 1' −X B2 − is equivalent to Rf 1 .

[0713] R 91 is a hydroxyl group, −F, −Cl, or −O−C 1－3 alkyl (specifically, methoxy, ethoxy). In one embodiment, R 91 is a hydroxyl group. In one embodiment, R91 is -F. In one embodiment, R 91 is -Cl. In one embodiment, R 91 is -O-lower alkyl.

[0714] -C(=O)- is included in X A .

[0715] In formula (2a), for example, X B2 is a single bond and R 91 is a hydrogen atom. In another example, X B2 is a divalent organic group and R 91 is a hydrogen atom.

[0716] Formula (2b):

[0717] Rf 1’ -X B3 -X A3 -CH=CH 2 …(2b)

[0718] Rf 1' has the same meaning as above.

[0719] X B3 is (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group.

[0720] c11, c12 and c13 are each independently an integer from 0 to 200; wherein the sum of c12 and c13 is an integer from 0 to 200.

[0721] Rf 1' -X B3 - is equivalent to Rf 1 .

[0722] X A3 are each independently a single bond or C(=O)NR 53 -(CH 2 ) c14 .

[0723] R 53 is a hydrogen atom or a monovalent organic group. In one embodiment, R 53 is a hydrogen atom. X A3 is included in X A .

[0724] c14 is an integer from 0 to 30.

[0725] In one embodiment, -X A3 -CH 2CH 2 - is X A .

[0726] Formula (2c):

[0727] Rf 1’ -X B4 -X A4 -Si(X A5 -CH=CH 2 ) δ3 R 95 3-δ3 …(2c)

[0728] Formula (2c) is a precursor of a compound containing the group shown in Formula (S2) or (S3).

[0729] Rf 1' has the same meaning as above.

[0730] X B4 is (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group.

[0731] c11, c12 and c13 are each independently an integer from 0 to 200. Among them, the sum of c12 and c13 is an integer from 0 to 200.

[0732] Rf 1' -X B4 - is equivalent to Rf 1 .

[0733] X A4 are each independently a single bond or C(=O)NR 53 -(CH 2 ) c15 . R 53 has the same meaning as above. c15 is an integer from 0 to 30. X A4 is equivalent to X A .

[0734] X A5 are each independently a single bond or a divalent organic group. -X A5 -CH 2 CH 2 - is equivalent to -Z 1 .

[0735] R 95 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group. In one embodiment, R 95Each is independently a hydroxyl group or a monovalent organic group. However, the monovalent organic group does not include -X A5 -CH=CH 2 . R 95 Is equivalent to R b1 Or R c1 .

[0736] δ3 is an integer from 1 to 3 and is equivalent to k1.

[0737] Formula (2d):

[0738] Rf 1’ -X B4 -X A4 -C(X A6 -CH=CH 2 ) δ4 R 96 3-δ4 …(2d)

[0739] Formula (2d) is a precursor of a compound containing the group shown in formula (S4).

[0740] Rf 1' Has the same meaning as above.

[0741] X B4 Is (CH 2 ) c11 、(CH 2 ) c12 -O-(CH 2 ) c13 Or a divalent polysiloxane-containing group.

[0742] c11, c12 and c13 are each independently an integer from 0 to 200.

[0743] Rf 1' -X B4 -Is equivalent to Rf 1 .

[0744] X A4 Has the same meaning as above. X A4 Is equivalent to X A .

[0745] X A6 Are each independently a single bond, an oxygen atom or a divalent organic group. -X A6 -CH 2 CH 2 -Is equivalent to Z 3 . R e1 Based on -X A5 -CH 2 CH 2 -Formed.

[0746] R 96 is independently a hydrogen atom, a hydroxyl group or a monovalent organic group, provided that the monovalent organic group does not include -X A6 -CH=CH 2 . R 96 is equivalent to R f1 .

[0747] δ4 is an integer from 1 to 3 and is equivalent to l2.

[0748] Formula (2e):

[0749] Rf 1’ -X B4 -X A4 -NR 97 2 …(2e)

[0750] Rf 1' has the same meaning as above.

[0751] X B4 is (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group.

[0752] c11, c12 and c13 are independently integers from 0 to 200.

[0753] Rf 1' -X B4 - is equivalent to Rf 1 .

[0754] X A4 has the same meaning as above. X A4 is equivalent to X A .

[0755] R 97 is independently represented by -R 92 -CH=CH 2 or -R 94 -Q A1 (R 92 -CH=CH 2 ) δ31 R 93 δ32 means.

[0756] R 92 is a single bond, an oxygen atom or a divalent organic group. The -R 92 -CH=CH 2 from R 92-CH 2 CH 2 -For example, Z corresponding to formula (S3) 1 or Z of formula (S4) 2 or Z 3 .

[0757] R 94 is a single bond, an oxygen atom or a divalent organic group;

[0758] Q A1 are each independently N, Si or C;

[0759] R 93 is a hydrogen atom, a hydroxyl group or a monovalent organic group;

[0760] δ31 and δ32 are each independently an integer of 1 or more;

[0761] The sum of δ31 and δ32 is the valence number of Q A1 -1.

[0762] Formula (2f):

[0763] Rf 1’ -X B5 -X A7 -NR 53 -R 98 …(2f)

[0764] Rf 1' has the same meaning as above.

[0765] X B5 is represented by (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group.

[0766] c11, c12 and c13 are each independently an integer from 0 to 200.

[0767] Rf 1' -X B5 -corresponds to Rf 1 .

[0768] X A7 is a single bond or C(=O).

[0769] R 98 is composed of -R 92 -CH=CH 2 or -R 94 -Q A1 (R 92-CH=CH 2 ) δ31 R 93 δ32 represents.

[0770] R 92 is a single bond, an oxygen atom or a divalent organic group.

[0771] R 94 is a single bond, an oxygen atom or a divalent organic group.

[0772] Q A1 are each independently N, Si or C.

[0773] R 93 is a hydrogen atom, a hydroxyl group or a monovalent organic group.

[0774] δ31 and δ32 are each independently an integer of 1 or more.

[0775] The sum of δ31 and δ32 is Q A1 's valence number - 1.

[0776] In one embodiment, X A7 -NR 53 corresponds to X A . R 53 has the same meaning as above.

[0777] In one embodiment, R 98 is represented by -R 92 -CH=CH 2 A7 . At this time, X-NR 53 -R 98 corresponds to X A .

[0778] In one embodiment, R 98 is represented by -R 94 -Q A1 (R 92 -CH=CH 2 ) δ31 R 93 δ32 A7 . At this time, X-NR 53 -R 94 corresponds to X A .

[0779] Formula (2g):

[0780]

[0781] R A31 is represented by -Rf 1 where Rf1 The meaning is the same as above.

[0782] R A32 from -X A31 -CH=CH 2 or -X A33 -Q A2 (X A32 -CH=CH 2 ) δ41 R 36 δ42 represents;

[0783] R A33 from -Rf 1 、-X A31 -CH=CH 2 or -X A33 -Q A2 (X A32 -CH=CH 2 ) δ41 R 36 δ42 represents.

[0784] X A31 、X A32 and X A33 are each independently a single bond, an oxygen atom or a divalent organic group.

[0785] Q A2 are each independently N, Si or C.

[0786] The group having at least one of X A31 -CH 2 CH 2 and X A33 bonded to the isocyanuric acid ring is equivalent to X in formula (1) A . X A32 -CH 2 CH 2 When Q A2 is Si, it is equivalent to Z in formula (S3) 1 、When Q A2 is C, it is equivalent to Z in formula (S4) 3 、When Q A2 is N, it is equivalent to Z in formula (S5) 4 .

[0787] R 36 is a hydrogen atom, a hydroxyl group or a monovalent organic group.

[0788] δ41 and δ42 are each independently an integer of 1 or more. The sum of δ41 and δ42 is the valence number of Q A2 -1.

[0789] [Surface treatment agent]

[0790] The surface treatment agent of the present invention will be described below.

[0791] The surface treatment agent of the present invention contains at least one fluorine atom-containing silane compound represented by the formula (1).

[0792] The surface treatment agent of the present invention may also contain a condensate of a fluorine atom-containing silane compound.

[0793] In one embodiment, the surface treatment agent of the present invention contains at least one of a fluorine atom-containing silane compound and a compound composed of a condensate formed by condensation of at least a part of the fluorine atom-containing silane compound.

[0794] The surface treatment agent of the present invention may contain a solvent, an organosilicon compound (hereinafter referred to as "silicone oil") that can be understood as silicone oil (non-reactive), an amine compound, an alcohol, a catalyst, a surfactant, a polymerization inhibitor, a sensitizer, etc.

[0795] In one embodiment, the surface treatment agent of the present invention contains a compound represented by R 90 -OH.

[0796] R 90 is a monovalent organic group, preferably a C 1－20 alkyl group or a C 3－20 alkylene group, and these groups may be substituted by one or more substituents. Examples of the substituent include a hydroxyl group, -OR 901 (wherein R 901 is a C 1－10 alkyl group, preferably a C 1－3 alkyl group, such as a methyl group).

[0797] In one embodiment, the surface treatment agent of the present invention may contain a solvent selected from R 81 OR 82 , R 83 n8 C 6 H 6－n8 , R 84 R 85 R 86 Si-(O-SiR 87 R 88 ) m8 -R 89 and (OSiR 87 R 88 ) m9 shown compounds.

[0798] [In the formula,

[0799] R 81 ~R89 Each is independently a monovalent organic group having 1 to 10 carbon atoms,

[0800] m8 is an integer from 1 to 6,

[0801] m9 is an integer from 3 to 8,

[0802] n8 is an integer from 0 to 6.

[0803] The above monovalent organic group having 1 to 10 carbon atoms can be straight-chain, branched-chain, or can contain a cyclic structure.

[0804] In one embodiment, the above monovalent organic group having 1 to 10 carbon atoms can contain an oxygen atom, a nitrogen atom, or a halogen atom.

[0805] In another embodiment, the above monovalent organic group having 1 to 10 carbon atoms does not contain a halogen atom.

[0806] In a preferred embodiment, the above monovalent organic group having 1 to 10 carbon atoms is a hydrocarbon group that can be substituted by a halogen, preferably a hydrocarbon group not substituted by a halogen.

[0807] In one embodiment, the above hydrocarbon group is straight-chain.

[0808] In another embodiment, the above hydrocarbon group is branched-chain.

[0809] In another embodiment, the above hydrocarbon group contains a cyclic structure.

[0810] In one embodiment, the above solvent is R 81 OR 82 .

[0811] R 81 and R 82 are each independently preferably a hydrocarbon group having 1 to 8 carbon atoms, more preferably an alkyl group of C 1－6 or a cycloalkyl group of C 5－8 .

[0812] In one embodiment, the above solvent is R 83 n8 C 6 H 6－n8 .

[0813] C 6 H 6－n8 is an n8-valent benzene ring. That is, R 83 n8 C 6 H 6－n8 is a benzene substituted by n8 R 83 .

[0814] R 83Each independently is a halogen or an alkyl group of C that can be substituted by a halogen 1－6 alkyl group.

[0815] n8 is preferably an integer from 1 to 3.

[0816] In one embodiment, the above solvent is R 84 R 85 R 86 Si-(O-SiR 87 R 88 ) m8 -R 89 .

[0817] In one embodiment, the above solvent is (OSiR 87 R 88 ) m9 . (OSiR 87 R 88 ) m9 is a cyclic siloxane formed by cyclic bonding of multiple OSiR 87 R 88 units.

[0818] R 84 ~R 89 are each independently a hydrogen atom or an alkyl group of C 1－6 , preferably an alkyl group of C 1－6 , more preferably an alkyl group of C 1－3 , and even more preferably a methyl group.

[0819] m8 is preferably an integer from 1 to 6, more preferably an integer from 1 to 5, and even more preferably 1 to 2.

[0820] m9 is preferably an integer from 3 to 6, more preferably an integer from 3 to 5.

[0821] In one embodiment, the above solvent is hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, or decamethylcyclopentasiloxane.

[0822] In one mode, examples of the above solvent include: aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and petroleum spirit; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; esters such as methyl acetate, ethyl acetate, n-propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, and 2-heptanone; glycol ethers such as ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, and ethylene glycol monoalkyl ether; alcohols such as methanol, ethanol, isopropyl alcohol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, and tert-amyl alcohol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran, tetrahydropyran, and dioxane; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether alcohols such as methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, and diethylene glycol monomethyl ether; diethylene glycol monoethyl ether acetate; ethers such as cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, and decamethylcyclopentasiloxane; fluorinated solvents such as 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, dimethyl sulfoxide, 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225), ZEORORAH, 1,3-bis(trifluoromethyl)benzene, HFE7100, HFE7200, HFE7300, CF 3 CH 2 OH, CF 3 CF 2 CH 2 OH, (CF 3 ) 2 CHOH, and other fluorinated solvents. Alternatively, a mixed solvent of two or more of them can be mentioned.

[0823] The silicone oil is not particularly limited, and examples thereof include compounds represented by the following general formula (3).

[0824] R 1a -(SiR 3a 2 -O) f1-SiR 3a 2 -R 1a ···(3)

[0825] [In the formula:

[0826] R 1a are each independently a hydrogen atom or a hydrocarbon group,

[0827] R 3a are each independently a hydrogen atom or a hydrocarbon group,

[0828] f1 is from 2 to 3000.]

[0829] The above R 3a are each independently a hydrogen atom or a hydrocarbon group. The hydrocarbon group may be substituted.

[0830] R 3a are each independently preferably an unsubstituted hydrocarbon group or a hydrocarbon group substituted with a halogen atom. The halogen atom is preferably a fluorine atom.

[0831] R 3a are each independently preferably a C 1－6 alkyl group or an aryl group that may be substituted with a halogen atom, more preferably a C 1－6 alkyl group or an aryl group.

[0832] The above C 1－6 alkyl group may be straight-chain or branched-chain, preferably straight-chain. The C 1－6 alkyl group is preferably a C 1－3 alkyl group, more preferably methyl.

[0833] The above aryl group is preferably phenyl.

[0834] In one embodiment, R 3a are each independently a C 1－6 alkyl group, preferably a C 1－3 alkyl group, more preferably methyl.

[0835] In another embodiment, R 3a is phenyl.

[0836] In another embodiment, R 3a is methyl or phenyl, preferably methyl.

[0837] The above R 1a are each independently a hydrogen atom or a hydrocarbon group, having the same meaning as the above R 3a above.

[0838] R 1a are each independently preferably a C 1－6 alkyl group or an aryl group that may be substituted with a halogen atom, more preferably a C 1－6 alkyl group or an aryl group.

[0839] In one embodiment, R 1a is independently C 1－6 alkyl, preferably C 1－3 alkyl, more preferably methyl.

[0840] In another embodiment, R 1a is phenyl.

[0841] In another embodiment, R 1a is methyl or phenyl, preferably methyl.

[0842] The above f1 is from 2 to 1500. f1 is preferably 5 or more, more preferably 10 or more, further preferably 15 or more, and for example can be 30 or more or 50 or more. f1 is preferably 1000 or less, more preferably 500 or less, further preferably 200 or less, further more preferably 150 or less, and for example can be 100 or less or 80 or less.

[0843] f1 is preferably from 5 to 1000, more preferably from 10 to 500, further preferably from 15 to 200, and further more preferably from 15 to 150.

[0844] As another silicone oil, the compound shown in the following (3b) can be cited.

[0845] R 1a -R S12 -R 3a ···(3b)

[0846] [In the formula:

[0847] R 1a is independently a hydrocarbon group,

[0848] R 3a is independently a hydrocarbon group,

[0849] R S12 is -R S1 -SiR 2 2 -,

[0850] R S1 is independently a group represented by the following formula:

[0851]

[0852] (In the formula:

[0853] R 3 is independently C 1－12 alkylene, -R 6 -O-R 6 -, -R8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -or-R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -

[0854] R 4 C 1－12 Alkylene, -R 6 -O-R 6 -, -R 8 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 7 -R 8 -, -R 8 -R 7 -R 9 -R 6 -R 9 -R 7 -R 8 -or-R 9 -R 6 -R 9 -R 7 -R 9 -R 6 -R 9 -

[0855] R 6 C 1－6 Alkylene,

[0856] R 7 are each independently a phenylene group or a naphthylene group which may be substituted,

[0857] R 8 are independently a single bond or C 1－6 Alkylene,

[0858] R 9Each is independently a single bond or an oxygen atom,

[0859] R 5 Each is independently a hydrocarbon group,

[0860] x2 is an integer from 0 to 200,

[0861] y2 is an integer from 0 to 200,

[0862] z2 is an integer from 0 to 200,

[0863] y2 + z2 is 1 or more,

[0864] The order of existence of each repeating unit labeled with x2, y2, or z2 and enclosed in parentheses is arbitrary in the formula.)

[0865] R 2 Each is independently a hydrocarbon group.

[0866] The above silicone oil may have an average molecular weight of 500 to 100,000, preferably 1,000 to 10,000. The molecular weight of the silicone oil can be measured using GPC.

[0867] As the above silicone oil, for example, a linear or cyclic silicone oil with f1 of 30 or less represented by -(SiR 3a 2 -O) f1 - can be used. The linear silicone oil can be a so-called ordinary silicone oil and a modified silicone oil. As the ordinary silicone oil, dimethyl silicone oil, methylphenyl silicone oil, and methylhydrogen silicone oil can be cited. As the modified silicone oil, silicone oils obtained by modifying ordinary silicone oils with alkyl groups, aralkyl groups, polyethers, higher fatty acid esters, fluoroalkyl groups, amino groups, epoxy groups, carboxyl groups, alcohols, etc. can be cited. As the cyclic silicone oil, cyclic dimethylsiloxane oil, etc. can be cited.

[0868] Relative to the surface treatment agent of the present invention, the above silicone oil may contain, for example, 0 to 50% by mass, preferably 0.001 to 30% by mass, more preferably 0.1 to 5% by mass.

[0869] In one embodiment, in the composition of the present invention, the silicone oil contains, for example, 0 to 300 parts by mass, preferably 0 to 100 parts by mass, more preferably 0 to 50 parts by mass, and further preferably 0 to 10 parts by mass relative to a total of 100 parts by mass of the compounds of the present invention (when there are two or more, their total, the same below).

[0870] The silicone oil helps to improve the surface smoothness of the surface treatment layer.

[0871] As the above alcohols, for example, alcohols having 1 to 6 carbon atoms that can be substituted with one or more fluorine atoms can be cited. For example, methanol, ethanol, isopropanol, tert-butanol, CF3 CH 2 OH, CF 3 CF 2 CH 2 OH, (CF 3 ) 2 CHOH. By adding these alcohols to the surface treatment agent, the stability of the surface treatment agent can be improved.

[0872] As the above-mentioned catalyst, acids (such as acetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc.), bases (such as sodium hydroxide, potassium hydroxide, ammonia, triethylamine, diethylamine, etc.), transition metals (such as Ti, Ni, Sn, Zr, Al, B, Si, Ta, Nb, Mo, W, Cr, Hf, V, etc.), sulfur-containing compounds or nitrogen-containing compounds having unshared electron pairs in the molecular structure (such as sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphoric acid amide compounds, amide compounds, urea compounds), etc. can be cited.

[0873] As the above-mentioned aliphatic amine compound, for example, diethylamine, triethylamine, etc. can be cited. As the above-mentioned aromatic amine compound, for example, aniline, pyridine, etc. can be cited.

[0874] In a preferred embodiment, the above-mentioned transition metal is contained in the form of a transition metal compound represented by M-R (wherein M is a transition metal atom and R is a hydrolyzable group). By making the transition metal compound a compound formed by combining a transition metal with a hydrolyzable group, the surface treatment layer can contain transition metal atoms more efficiently, and the friction durability and chemical resistance of the surface treatment layer can be further improved.

[0875] The above-mentioned hydrolyzable group refers to a group that can undergo a hydrolysis reaction in the same way as the hydrolyzable group involved in the above-mentioned fluorine atom-containing silane compound, that is, a group that can be detached from the transition metal atom through a hydrolysis reaction. As examples of the hydrolyzable group, -OR m , -OCOR m , -O-N=CR m 2 , -NR m 2 , -NHR m , -NCO, halogen (in these formulas, R m represents a substituted or unsubstituted C 1－4 alkyl), etc. can be cited.

[0876] In a preferred embodiment, the above-mentioned hydrolyzable group is -OR m, preferably a methoxy group or an ethoxy group. By using an alkoxy group as the hydrolyzable group, it is possible to more efficiently incorporate transition metal atoms into the surface treatment layer, and further improve the friction durability and chemical resistance of the surface treatment layer.

[0877] In one embodiment, the hydrolyzable group may be the same as the hydrolyzable group contained in the fluorine atom-containing silane compound. By making the hydrolyzable groups in the fluorine atom-containing silane compound and the transition metal compound the same group, even when such hydrolyzable groups are exchanged with each other, the influence can be reduced.

[0878] In another embodiment, the hydrolyzable group may also be different from the hydrolyzable group contained in the fluorine atom-containing silane compound. By making the hydrolyzable groups in the fluorine atom-containing silane compound and the transition metal compound different, the reactivity of hydrolysis can be controlled.

[0879] In one embodiment, the hydrolyzable group and the hydrolyzable group contained in the fluorine atom-containing silane compound may be mutually replaceable in the surface treatment agent.

[0880] In a preferred embodiment, the transition metal compound is Ta(OR m ) 5 , and may preferably be Ta(OCH 2 CH 3 ) 5 .

[0881] Relative to the entire surface treatment agent, the above catalyst may contain, for example, 0.0002% by mass or more. Relative to the entire surface treatment agent, the above catalyst preferably contains 0.02% by mass or more, more preferably contains 0.04% by mass or more. Relative to the entire surface treatment agent, the above catalyst may contain, for example, 10% by mass or less, particularly 1% by mass or less. The surface treatment agent of the present invention, by containing the above catalyst at the above concentration, helps to form a surface treatment layer with better durability.

[0882] The content of the above catalyst relative to the fluorine atom-containing silane compound of the present invention is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, and particularly preferably 0 to 1% by mass.

[0883] The catalyst promotes the hydrolysis and dehydration condensation of the fluorine atom-containing silane compound of the present invention, and promotes the formation of the layer formed by the surface treatment agent of the present invention.

[0884] As other components, in addition to the above components, for example, tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, methyltriacetoxysilane, etc. can also be cited.

[0885] In the surface treatment agent of the present invention, in addition to the above components, as impurities, for example, trace amounts of Pt, Rh, Ru, 1,3-divinyltetramethyldisiloxane, triphenylphosphine, NaCl, KCl, condensates of silanes, etc. may be contained.

[0886] In one embodiment, the surface treatment agent of the present invention is used for the dry coating method, and preferably for vacuum evaporation.

[0887] In one embodiment, the surface treatment agent of the present invention is used for the wet coating method, and preferably for dip coating.

[0888] The surface treatment agent of the present invention can be impregnated into a porous material, such as a porous ceramic material, or a material in which metal fibers, such as steel wool, are fixed in a cotton-like form, to form pellets. These pellets can be used, for example, for vacuum evaporation.

[0889] [Article]

[0890] Hereinafter, the article of the present invention will be described.

[0891] The article of the present invention includes a substrate and a layer (surface treatment layer) formed on the surface of the substrate by the surface treatment agent of the present invention.

[0892] The substrate that can be used in the present invention can be composed of, for example, glass, resin (natural or synthetic resin, such as ordinary plastic materials), metal, ceramic, semiconductor (such as silicon, germanium), fiber (fabric, non-woven fabric, etc.), fur, leather, wood, ceramics, stone, etc., building materials, sanitary products, and any suitable material.

[0893] For example, when the article to be manufactured is an optical component, the material constituting the surface of the substrate can be a material for optical components, such as glass or transparent plastic. In addition, when the article to be manufactured is an optical component, a certain layer (or film), such as a hard coat or an antireflection layer, can also be formed on the surface (outermost layer) of the substrate. The antireflection layer can be any of a single-layer antireflection layer and a multilayer antireflection layer. Examples of inorganic substances that can be used as the antireflection layer include SiO 2 , SiO, ZrO 2 , TiO 2 , TiO, Ti 2 O 3 , Ti 2 O 5 , Al 2 O 3 , Ta 2 O 5 , Ta 3 O 5 , Nb 2 O 5 , HfO2 , Si 3 N 4 , CeO 2 , MgO, Y 2 O 3 , SnO 2 , MgF 2 , WO 3 , etc. These inorganic substances can be used alone, or two or more of them can be combined (for example, to form a mixture) and used. In the case of forming a multi-layer antireflection layer, it is preferable to use SiO 2 and / or SiO on its outermost layer. In the case where the article to be manufactured is an optical glass component for a touch panel, a transparent electrode may be provided on a part of the surface of the substrate (glass), for example, a thin film of indium tin oxide (ITO) or indium zinc oxide, etc. is used. In addition, in the substrate, according to its specific specifications, etc., there may also be an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), a fogging film layer, a hard coating film layer, a polarizing film, a retardation film, and a liquid crystal display module, etc.

[0894] The shape of the above-mentioned substrate is not particularly limited, and it can be, for example, plate-shaped, film-shaped, or other forms. In addition, the surface area of the substrate on which the surface treatment layer is to be formed only needs to be at least a part of the substrate surface, and it can be appropriately determined according to the use and specific specifications of the article to be manufactured, etc.

[0895] In one mode, as such a substrate, it can be a substrate at least a part of the surface of which is formed of a material that originally has hydroxyl groups. As such a material, glass can be cited, and metals (especially base metals), ceramics, semiconductors, etc. that can form a natural oxide film or a thermal oxide film on the surface can also be cited. Or, like resins, etc., in the case where there are hydroxyl groups but they are not sufficient, or in the case where there are no hydroxyl groups originally, by performing a certain pretreatment on the substrate, hydroxyl groups can be introduced onto the surface of the substrate or the hydroxyl groups can be increased. As an example of such a pretreatment, plasma treatment (such as corona discharge) or ion beam irradiation can be cited. Plasma treatment can also be suitably used in order to be able to introduce hydroxyl groups onto the substrate surface or increase the hydroxyl groups and purify the substrate surface (remove foreign substances, etc.). In addition, as other examples of such a pretreatment, the following methods can be cited: using the LB method (Langmuir-Blodgett method) or chemical adsorption method, etc., a surface adsorbent having a carbon-carbon unsaturated bond group is pre-formed in the form of a monomolecular film on the substrate surface, and then, in an atmosphere containing oxygen and nitrogen, etc., the unsaturated bond is broken.

[0896] In another mode, as such a substrate, it can also be a substrate at least a part of the surface of which is formed of an organosilicon compound having one or more other reactive groups, such as an Si-H group, or a material containing an alkoxysilane.

[0897] In a preferred embodiment, the above-mentioned substrate is glass. As such glass, sapphire glass, soda-lime glass, alkali aluminosilicate glass, borosilicate glass, alkali-free glass, crystal glass, and quartz glass are preferred, and chemically strengthened soda-lime glass, chemically strengthened alkali aluminosilicate glass, and chemically bonded borosilicate glass are particularly preferred.

[0898] In one embodiment, the article of the present invention may have a silicon oxide-containing intermediate layer between the glass and the surface treatment layer. By providing such an intermediate layer, the adhesion between the glass and the surface treatment layer is improved, and the durability is improved.

[0899] In a preferred embodiment, the above-mentioned intermediate layer may contain an alkali metal in addition to silicon oxide.

[0900] Examples of the above-mentioned alkali metal include lithium, sodium, potassium, etc. The above-mentioned alkali metal is preferably sodium.

[0901] The thickness of the intermediate layer is not particularly limited, and is preferably 1 to 200 nm, particularly preferably 1 to 20 nm. By making the thickness of the intermediate layer above the lower limit value of the above range, the effect of improving the adhesiveness by using the intermediate layer is better.

[0902] The concentration of alkali metal atoms in the intermediate layer can be measured using various surface analysis devices, such as TOF-SIMS, XPS (X-ray photoelectron spectroscopy), XRF (fluorescent X-ray analysis), etc.

[0903] The ratio of alkali metal atoms to all atoms in the entire intermediate layer can be obtained by depth analysis of XPS using ion sputtering, and is performed by alternately repeating the measurement using XPS and surface etching using ion sputtering with an ion gun built into the XPS apparatus.

[0904] In the intermediate layer, regarding the average value of the alkali metal concentration in the region within 1 nm from the surface in contact with the surface treatment layer, after obtaining the distribution curve of the alkali metal atom concentration in the depth direction by depth analysis of TOF-SIMS (time-of-flight secondary ion mass spectrometry) using ion sputtering, the average value of the alkali metal atom concentration on the distribution curve is calculated and obtained. The depth analysis of TOF-SIMS using ion sputtering is performed by alternately repeating the measurement using TOF-SIMS and surface etching using ion sputtering with an ion gun built into the TOF-SIMS apparatus.

[0905] By forming a layer of the surface treatment agent of the present invention on the surface of the above-mentioned substrate and then performing post-treatment on the layer as needed, a layer is formed from the surface treatment agent of the present invention, whereby the article of the present invention can be manufactured.

[0906] The formation of the layer of the surface treatment agent of the present invention can be carried out by applying the above surface treatment agent to the surface of the substrate in a manner that covers the surface of the substrate. The covering method is not particularly limited. For example, a wet covering method and a dry covering method can be used.

[0907] Examples of the wet covering method include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating, wipe coating, squeegee coat method, die coating, inkjet, casting method, Langmuir-Blodgett method, and similar methods.

[0908] Examples of the dry covering method include vapor deposition (usually vacuum vapor deposition), sputtering, CVD, and similar methods. Specific examples of the vapor deposition method (usually the vacuum vapor deposition method) include resistance heating, electron beam, high-frequency heating using microwaves, ion beam, and similar methods. Specific examples of the CVD method include plasma-CVD, optical CVD, thermal CVD, and similar methods.

[0909] In addition, covering using an atmospheric pressure plasma method can also be used.

[0910] In the case of using the wet covering method, the surface treatment agent of the present invention can be diluted with a solvent and applied to the surface of the substrate. From the viewpoints of the stability of the composition of the present invention and the volatility of the solvent, the following solvents are preferably used: aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and petroleum spirit; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; esters such as methyl acetate, ethyl acetate, n-propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methyl amino ketone, and 2-heptanone; glycol ethers such as ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, and ethylene glycol monoalkyl ether; alcohols such as methanol, ethanol, isopropyl alcohol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, and tert-amyl alcohol; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran, tetrahydropyran, and dioxane; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether alcohols such as methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, and diethylene glycol monomethyl ether; diethylene glycol monoethyl ether acetate; polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C 6 F 13 CH 2 CH 3 (e.g., ASAHIKLIN (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., ZEORORA (registered trademark) H manufactured by Nippon Zeon Co., Ltd.); hydrofluoroethers (HFE) (e.g., perfluoropropyl methyl ether (C 3 F 7 OCH 3 )(e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C 4 F 9 OCH 3 )(e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C 4 F 9 OC 2 H 5)(e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C 2 F 5 CF(OCH 3 )C 3 F 7 )(e.g., Novec (trademark) 7300 manufactured by Sumitomo 3M Limited), etc. alkyl perfluoroalkyl ethers (the perfluoroalkyl group and the alkyl group may be straight-chain or branched-chain), or CF 3 CH 2 OCF 2 CHF 2 (e.g., ASAHIKLIN (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.), ether alcohols such as cyclopentyl methyl ether; siloxanes such as hexamethyldisiloxane, hexaethyldisiloxane, octamethytrisiloxane, octamethylcyclotetrasiloxane, octamethylcyclopentasiloxane, etc. These solvents can be used alone or in the form of a mixture of two or more kinds.

[0911] In one mode, as the solvent when using the wet coating method, for example, a compound represented by R 90 -OH can be used.

[0912] R 90 is a monovalent organic group, preferably a C 1－20 alkyl group or a C 3－20 alkylene group, and these groups may be substituted with one or more substituents. As the substituents, for example, hydroxyl group, -OR 901 (wherein R 901 is a C 1－10 alkyl group, preferably a C 1－3 alkyl group, for example, a methyl group) can be cited.

[0913] In the case of using the dry coating method, the surface treatment agent of the present invention can be directly applied to the dry coating method, or can also be applied to the dry coating method after being diluted with the above-mentioned solvent.

[0914] The formation of the layer of the surface treatment agent is preferably carried out in such a manner that the surface treatment agent of the present invention coexists with a catalyst for hydrolysis and dehydration condensation in the layer. In short, in the case of using the wet coating method, after diluting the surface treatment agent of the present invention with a solvent, before applying it to the surface of the substrate, a catalyst can be added to the diluted solution of the surface treatment agent of the present invention. In the case of using the dry coating method, the surface treatment agent of the present invention after adding the catalyst can be directly subjected to evaporation coating (usually vacuum evaporation coating) treatment, or the surface treatment agent of the present invention after adding the catalyst can be infiltrated into a metal porous body such as iron or copper to obtain a granular material, and the obtained granular material can be used for evaporation coating (usually vacuum evaporation coating) treatment.

[0915] The catalyst can be any suitable acid or base, transition metal (such as Ti, Ni, Sn, Zr, Al, B, etc.), sulfur-containing compound or nitrogen-containing compound having unshared electron pairs in the molecular structure (such as sulfoxide compound, aliphatic amine compound, aromatic amine compound, phosphoric acid amide compound, amide compound, urea compound), etc. As the acid catalyst, for example, acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. can be used. In addition, as the base catalyst, for example, ammonia, sodium hydroxide, potassium hydroxide, organic amines such as triethylamine, diethylamine, etc. can be used. The same substances as those described above can be cited for the transition metal, aliphatic amine compound and aromatic amine compound.

[0916] The surface treatment layer included in the article of the present invention has high friction durability on both sides. In addition, in addition to high friction durability, the above surface treatment layer can also have water repellency, oil repellency, antifouling property (such as preventing attachment of stains such as fingerprints), waterproof property (preventing water from infiltrating into electronic components, etc.), surface smoothness (or lubricity, such as wipeability of stains such as fingerprints, excellent finger touch), chemical resistance, etc., depending on the composition of the surface treatment agent used, and is suitable for use as a functional film.

[0917] Therefore, the present invention also relates to an optical material having the above surface treatment layer on the outermost layer.

[0918] As the optical material, in addition to the optical materials related to displays as exemplified below, a variety of optical materials are preferably cited, such as: cathode ray tubes (CRTs, such as computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin film EL dot matrix displays, rear projection displays, fluorescent display tubes (VFDs), field emission displays (FEDs, Field Emission Display), etc. displays or protection plates of these displays, or materials having an antireflection film treatment on their surfaces.

[0919] The article of the present invention is not particularly limited and can be an optical component. Examples of the optical component can be cited as follows: lenses for glasses, etc.; front protection plates, antireflection plates, polarizing plates, antiglare plates of displays such as PDPs, LCDs, etc.; touch panel sheets of devices such as mobile phones, portable information terminals, etc.; disk surfaces of Blu-ray (registered trademark) discs, DVD discs, CD-Rs, MOs, etc.; optical fibers; display surfaces of watches, etc.

[0920] In addition, the article of the present invention can also be a medical device or medical material. In addition, an article having a layer obtained by the present invention can also be an interior and exterior automotive material. Examples of exterior materials include the following: windows, lamp covers, and exterior camera covers for vehicles. Examples of interior materials include the following: instrument panel covers, navigation system touch panels, and decorative interior materials.

[0921] The thickness of the above layer is not particularly limited. In the case of an optical component, from the viewpoints of optical performance, friction durability (abrasion resistance), and antifouling property, it is preferable that the thickness of the above layer is in the range of 1 to 50 nm, 1 to 30 nm, and preferably 1 to 15 nm.

[0922] The embodiments have been described above, but it should be understood that various changes can be made to the mode and details as long as the gist and scope of the claimed scope are not deviated from.

[0923] Examples

[0924] The following is a specific description by way of examples, but the present invention is not limited to these examples.

[0925] (Synthesis Example 1)

[0926] Methyl 9-formylnonanoate (400 mg, 2 mmol) and dichloromethane (20 mL) were mixed, and after cooling with an ice bath, diethylaminosulfur trifluoride (DAST) (570 μL, 3.9 mmol) was slowly added dropwise. After stirring in the ice bath for 2 hours, water was slowly added dropwise, and the mixture was naturally warmed to room temperature. Thereafter, it was washed with water, saturated brine, and dried over magnesium sulfate, followed by concentration under reduced pressure to obtain a compound (1) in the form of a colorless liquid.

[0927] Compound (1)

[0928]

[0929] 1 H NMR (CDCl 3 , 400 MHz) δ 5.79 (tt, J = 56.7, 4.4 Hz, 1H), 3.67 (s, 3H), 2.31 (t, J = 7.6 Hz, 2H), 1.80 - 1.74 (m, 2H), 1.65 - 1.59 (m, 2H), 1.48 - 1.40 (2H), 1.35 - 1.28 (m, 8H) ppm.

[0930] 19 F NMR (CDCl 3 , 375 MHz) δ -115.6 (td, J = 56.7, 18.0 Hz, 2F) ppm.

[0931] (Synthesis Example 2)

[0932] The compound (1) (400 mg, 1.8 mmol) obtained in Synthesis Example 1, allylamine (1.6 mL), and 1,5,7-triazabicyclo[4.4.0]dec-5-ene dichloromethane (320 mg) were mixed, stirred at 50 °C for 2 hours, and then cooled to room temperature. Thereafter, it was diluted with chloroform, washed with hydrochloric acid and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 0.35 g of the compound (2) in the form of a colorless solid.

[0933] Thereafter, purification was carried out using a silica gel column chromatography (eluent: toluene → chloroform → ethyl acetate).

[0934] Compound (2)

[0935]

[0936] 1 H NMR(CDCl 3 , 400 MHz) δ 5.88 - 5.78 (m, 1H), 5.78 (tt, J = 57.0, 4.8 Hz, 1H), 5.52 (brs, 1H), 5.20 - 5.15 (m, 1H), 5.15 - 5.11 (m, 1H), 3.88 (t, J = 5.2 Hz, 2H), 2.19 (t, J = 8.0 Hz, 2H), 1.87 - 1.60 (m, 4H), 1.45 - 1.39 (m, 2H), 1.38 - 1.25 (m, 8H) ppm.

[0937] 19 F NMR(CDCl3, 375 MHz) δ -115.6 (td, J = 57.0, 15.0 Hz, 2F) ppm. (Synthesis Example 3)

[0938] 0.39 g of the compound (2) obtained in Synthesis Example 2, 8.4 mL of toluene, 0.0840 g of pyridine, and 0.5 mL of a xylene solution of a Pt coordination compound containing 2% of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane were added respectively, and then 0.64 mL of trimethoxysilane was added, and the mixture was stirred overnight at room temperature. Thereafter, purification was carried out to obtain 0.70 g of the following compound (3).

[0939] Compound (3)

[0940]

[0941] 1 H NMR(CDCl 3, 400 MHz) δ [ppm]: -0.018 - 0.149 (m), 0.621 - 0.662 (m), 1.245 - 1.299 (m), 1.391 - 1.464 (m), 1.575 - 1.670 (m), 1.730 - 1.869 (m), 2.119 - 2.158 (t), 3.230 - 3.262 (m), 3.528 - 3.613 (m), 5.625 - 5.933 (tt)

[0942] (Synthesis Example 4)

[0943] The compound (1) (0.5 g) obtained in Synthesis Example 1, diallylamine (0.6 g), and 1,5,7 - triazabicyclo[4.4.0]dec - 5 - ene dichloromethane (0.3 g) were mixed, stirred at 80 °C overnight, and then cooled to room temperature. Thereafter, it was diluted with toluene, washed with hydrochloric acid, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 530 mg of the following compound (4) in the form of a yellow liquid.

[0944] Compound (4)

[0945]

[0946] 1 H NMR (CDCl 3 , 400 MHz) δ 5.79 (tt, J = 59.6, 4.4 Hz, 1H), 5.81 - 5.71 (m, 2H), 5.22 - 5.09 (m, 4H), 3.99 (d, J = 6.0 Hz, 2H), 3.87 (d, J = 4.8 Hz, 2H), 2.30 (t, J = 8.0 Hz, 2H), 1.88 - 1.74 (m, 2H), 1.68 - 1.59 (m, 2H), 1.48 - 1.39 (2H), 1.38 - 1.28 (m, 8H) ppm.

[0947] 19 F NMR (CDCl 3 , 375 MHz) δ -115.6 (td, J = 59.6, 18.0 Hz, 2F) ppm. (Synthesis Example 5)

[0948] After adding 0.52 g of the compound (4) obtained in Synthesis Example 4, 9.0 mL of toluene, 0.0603 g of pyridine, and 0.5 mL of a xylene solution of a Pt coordination compound containing 2% of 1,3 - divinyl - 1,1,3,3 - tetramethyldisiloxane, 1.4 mL of trimethoxysilane was added, and the mixture was stirred at room temperature overnight. Thereafter, it was purified to obtain 0.71 g of the following compound (5) having a trimethoxysilyl group at the terminal.

[0949] Compound (5)

[0950]

[0951] 1 H NMR (CDCl 3 , 400 MHz) δ [ppm]: 0.011 - 0.203 (m), 0.493 - 0.635 (m), 1.208 - 1.851 (m), 2.251 - 2.396 (m), 3.145 - 3.301 (m), 3.471 - 3.660 (m), 5.618 - 5.926 (tt)

[0952] (Synthesis Example 6)

[0953] 0.5 g of Compound (1) obtained in Synthesis Example 1, 1.1 g of 2,2 - bis(1 - propenyl)-4 - pentenylamine, and 0.3 g of 1,5,7 - triazabicyclo[4.4.0]dec - 5 - ene dichloromethane were mixed, stirred at 50 °C overnight, and then cooled to room temperature. Thereafter, it was diluted with toluene, washed with hydrochloric acid, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 680 mg of the following Compound (6) in the form of a yellow liquid.

[0954] Compound (6)

[0955]

[0956] 1 H NMR (CDCl 3 , 400 MHz) δ 5.94 - 5.63 (m, 4H), 5.52 (t, J = 6.4 Hz, 1H), 5.21 - 5.07 (m, 6H), 3.20 (d, J = 6.4 Hz, 2H), 2.33 (t, J = 7.6 Hz, 2H), 2.03 (d, J = 7.6 Hz, 6H), 1.88 - 1.73 (m, 2H), 1.66 - 1.54 (m, 2H), 1.48 - 1.38 (2H), 1.38 - 1.28 (m, 8H) ppm.

[0957] 19 F NMR (CDCl 3 , 375 MHz) δ - 115.6 (td, J = 56.3, 17.6 Hz, 2F) ppm. (Synthesis Example 7)

[0958] After adding 0.69 g of the compound (6) obtained in Synthesis Example 6, 9.7 mL of toluene, 0.0703 g of pyridine, and 0.5 mL of a xylene solution containing 2% of a Pt coordination compound of 1,3 - divinyl - 1,1,3,3 - tetramethyldisiloxane, 2.4 mL of trimethoxysilane was added, and the mixture was stirred overnight at room temperature. Thereafter, purification was carried out to obtain 1.30 g of the following compound (7) having a trimethoxysilyl group at the terminal.

[0959] Compound (7)

[0960]

[0961] 1 H NMR(CDCl 3 , 400 MHz) δ [ppm]: 0.025 - 0.154 (m), 0.537 - 0.654 (m), 1.168 - 1.459 (m), 2.269 - 2.361 (m), 3.551 - 3.656 (m), 3.471 - 3.660 (m), 5.636 - 5.944 (tt)

[0962] (Synthesis Example 8)

[0963] 10 - Undecenal (4 g, 24 mmol) and dichloromethane (200 mL) were mixed, cooled in an ice bath, and diethylaminosulfur trifluoride (DAST) (7 mL, 48 mmol) was slowly added dropwise. After stirring in the ice bath for 2 hours, water was slowly added dropwise, and the mixture was naturally warmed to room temperature. Thereafter, it was washed with water, saturated brine, and dried over magnesium sulfate, followed by concentration under reduced pressure to obtain 4.3 g of the following compound (8) in the form of a colorless oily substance.

[0964] Compound (8)

[0965]

[0966] 1 H NMR(CDCl 3 , 400 MHz) δ 5.86 - 5.79 (m, 1H), 5.79 (tt, J = 57.0, 4.4 Hz, 1H), 5.03 - 4.96 (m, 1H), 4.95 - 4.91 (m, 1H), 2.07 - 2.01 (m, 2H), 1.88 - 1.74 (m, 2H), 1.48 - 1.30 (12H) ppm.

[0967] 19 F NMR(CDCl 3 , 375 MHz) δ - 115.3 (td, J = 57, 18 Hz, 2F) ppm.

[0968] (Synthesis Example 9)

[0969] After separately adding 0.95 g of the compound (8) obtained in Synthesis Example 8, 25 mL of toluene, 0.2 mL of pyridine, and 1.5 mL of a xylene solution of a Pt coordination compound containing 2% of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 2.0 mL of trimethoxysilane was added, and the mixture was stirred overnight at room temperature. Thereafter, purification was carried out to obtain 2.07 g of the following compound (9) having a trimethoxysilyl group at the terminal.

[0970] Compound (9)

[0971]

[0972] 1 H NMR(CDCl 3 , 400 MHz) δ [ppm]: -0.014 - 0.131 (m), 0.615 - 0.656 (m), 1.212 - 1.465 (m), 1.730 - 1.869 (m), 3.534 - 3.634 (m), 5.624 - 5.933 (tt)

[0973] (Synthesis Example 10)

[0974] 18-Bromo-1-octadecene (5 g), Pd 2 (dba) 3 (0.69 g), dppf (0.86 g), copper(I) iodide (2.87 g), cesium fluoride (9.09 g), difluoromethyltrimethylsilane (7.49 g), and dimethylformamide (50 mL) were added to a flask and stirred at 60 °C for 6 hours. Toluene and silica gel were added to the reaction solution, and after filtration, the filtrate was washed successively with an aqueous ammonium chloride solution and water. The liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane) to obtain 1.88 g of compound (10) in the form of a colorless liquid.

[0975] Compound (10)

[0976]

[0977] 1 H-NMR (400 MHz, chloroform-D) δ [ppm]: 1.26 - 1.46 (m, 28H), 1.72 - 1.88 (m, 2H), 2.01 - 2.09 (m, 2H), 4.91 - 5.01 (m, 2H), 5.63 - 5.94 (m, 2H)

[0978] 19F-NMR (376 MHz, chloroform-D) δ [ppm]: -115.6 (dt, 2F, J = 56.8, 17.7 Hz)

[0979] (Synthesis Example 11)

[0980] Into a flask were added the compound (10) (0.88 g) obtained in Synthesis Example 10, Karstedt catalyst (0.19 g, xylene solution containing 2% platinum), trimethoxysilane (1.07 g), pyridine (0.03 g), and toluene (5 mL). After stirring at room temperature for 4 hours, the mixture was concentrated under reduced pressure to obtain 1.20 g of the compound (11) as a yellow liquid.

[0981] Compound (11)

[0982]

[0983] 1 H-NMR (400 MHz, chloroform-D) δ [ppm]: 0.62 - 0.66 (m, 2H), 1.25 - 1.47 (m, 34H), 1.74 - 1.88 (m, 2H), 3.54 - 3.62 (m, 11H), 5.79 (tt, 1H, J = 56.9, 4.6 Hz)

[0984] 19 F-NMR (376 MHz, chloroform-D) δ [ppm]: -115.6 (dt, 2F, J = 56.8, 17.7 Hz)

[0985] (Synthesis Example 12)

[0986] Into a flask were added the compound (10) (0.93 g) obtained in Synthesis Example 10, trichlorosilane (2.50 g), triacetoxymethylsilane (0.03 g), Karstedt catalyst (0.60 g, xylene solution containing 2% platinum), and toluene (20 mL). The mixture was stirred at 60 °C for 2 hours. After concentrating the reaction solution under reduced pressure, tetrahydrofuran (10 mL) was added. While cooling to 5 °C or below, allylmagnesium chloride (23 mL, 0.8 mol / L tetrahydrofuran solution) was added dropwise, and the mixture was stirred at room temperature for 12 hours. Toluene and aqueous hydrochloric acid solution were added to the reaction solution and stirred. After standing, the aqueous layer was removed. The remaining organic layer was washed with water and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane) to obtain 1.25 g of the compound (12) as a colorless liquid.

[0987] Compound (12)

[0988]

[0989] 1 H-NMR (400 MHz, chloroform-D) δ [ppm]: 0.52 - 0.59 (m, 2H), 0.83 - 0.95 (m, 2H), 1.26 - 1.29 (m, 30H), 1.57 - 1.61 (m, 6H), 1.71 - 1.92 (m, 2H), 4.84 - 4.90 (m, 6H), 5.63 - 5.94 (m, 4H)

[0990] 19 F-NMR (376 MHz, chloroform-D) δ [ppm]: -115.6 (dt, 2F, J = 56.8, 17.7 Hz)

[0991] (Synthesis Example 13)

[0992] Add the compound (12) (1.25 g) obtained in Synthesis Example 12, Karstedt's catalyst (0.05 g, containing 20% platinum), trimethoxysilane (3.02 g), pyridine (0.09 g), and toluene (15 mL) to a flask. After stirring at room temperature for 4 hours, concentrate under reduced pressure to obtain 1.52 g of compound (13) in the form of a yellow liquid.

[0993] Compound (13)

[0994]

[0995] 1 H-NMR (400 MHz, chloroform-D) δ [ppm]: 0.39 - 0.50 (m, 2H), 0.54 - 0.62 (m, 6H), 0.65 - 0.72 (m, 6H), 1.25 - 1.46 (m, 38H), 1.74 - 1.88 (m, 2H), 3.51 - 3.63 (m, 27H), 5.78 (tt, 1H, J = 56.9, 4.6 Hz)

[0996] 19 F-NMR (376 MHz, chloroform-D) δ [ppm]: -115.6 (dt, 2F, J = 56.8, 17.7 Hz)

[0997] (Synthesis Example 14)

[0998] Add 22-docosenoic acid (0.5 g), thionyl chloride (1.5 mL), and N,N-dimethylformamide (1 drop) to a flask, and stir at 60 °C for 4 hours. After concentrating the reaction mixture under reduced pressure, add chloroform (1 mL) and 2,2-difluoroethanol (1 mL), and dropwise add pyridine (0.17 g) while cooling to below 5 °C. Then, warm the mixture to room temperature and stir for 12 hours. Add chloroform and aqueous hydrochloric acid to the reaction mixture, stir, let it stand, and remove the aqueous phase. Wash the remaining organic phase with water, dry it over anhydrous sodium sulfate, and concentrate it under reduced pressure to obtain 0.50 g of compound (14) as a pale yellow solid.

[0999] Compound (14)

[1000]

[1001] 1 H-NMR (400 MHz, chloroform-D) δ [ppm]: 1.25 - 1.37 (m, 36H), 2.01 - 2.22 (m, 2H), 2.33 - 2.39 (m, 2H), 4.27 (td, 2H, J = 13.7, 4.1 Hz), 4.91 - 5.02 (m, 2H), 5.76 - 6.08 (m, 2H)

[1002] 19 F-NMR (376 MHz, chloroform-D) δ [ppm]: -125.5 (dt, 2F, J = 53.8, 15.0 Hz)

[1003] (Synthesis Example 15)

[1004] Add the compound (14) (0.88 g) obtained in Synthesis Example 14, Karstedt's catalyst (0.19 g, xylene solution containing 2% platinum), trimethoxysilane (1.07 g), pyridine (0.03 g), and toluene (5 mL) to a flask. Stir at room temperature for 4 hours, then concentrate under reduced pressure to obtain 1.20 g of compound (15) as a yellow liquid.

[1005] Compound (15)

[1006]

[1007] 1 H-NMR (400 MHz, chloroform-D) δ [ppm]: 0.62 - 0.66 (m, 2H), 1.25 - 1.47 (m, 34H), 1.74 - 1.88 (m, 2H), 3.54 - 3.62 (m, 11H), 5.79 (tt, 1H, J = 56.9, 4.6 Hz)

[1008] 19F-NMR (376 MHz, chloroform-D) δ [ppm]: -115.6 (dt, 2F, J = 56.8, 17.7 Hz)

[1009] (Synthesis Example 16)

[1010] Stearoyl chloride (5 g), allylamine (2.5 mL), and dichloromethane (15 mL) were mixed and stirred overnight at room temperature. It was diluted with dichloromethane, washed with hydrochloric acid and water, and then concentrated under reduced pressure to obtain compound (16): C 17 H 35 -CONH-CH 2 CH=CH 2 (5.0 g).

[1011] Compound (16)

[1012] 1 H NMR (CDCl 3 , 400 MHz) δ [ppm]: 0.85 - 0.88 (m, 3H), 1.23 - 27 (m, 28H), 1.60 - 1.70 (m, 2H), 2.15 - 2.22 (m, 2H), 3.85 - 3.89 (m, 2H), 5.01 - 5.15 (m, 2H), 5.78 - 5.86 (m, 1H).

[1013] The above C 17 H 35 -CONH-CH 2 CH=CH 2 (5 g), toluene (70 mL), a xylene solution of Karstedt's catalyst (2%, 3.5 mL), aniline (0.5 g), and trimethoxysilane (5.9 mL) were mixed, stirred overnight at room temperature, and then concentrated under reduced pressure to obtain compound B: C 17 H 35 -CONH-CH 2 CH 2 CH 2 Si(OCH 3 ) 3 (6.3 g).

[1014] Compound B

[1015] 1 H NMR (CDCl 3 , 400 MHz) δ [ppm]: 0.53 - 0.65 (m, 2H) 0.85 - 0.91 (m, 3H), 1.24 - 27 (m, 28H), 1.60 - 1.648 (m, 4H), 2.12 - 2.24 (m, 2H), 3.21 - 3.26 (m, 2H) 3.56 - 3.60 (m, 9H)

[1016] (Synthesis Example 17)

[1017] Mix R-COOH (7.2 g), allylamine (0.4 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.36 g), 4-dimethylaminopyridine (60 mg) and dichloromethane (30 mL), and stir overnight at room temperature. Dilute with dichloromethane, wash with hydrochloric acid and water, and then concentrate under reduced pressure to obtain compound (17): R-CONHCH 2 CH=CH 2 (7.0 g). Among them, R- is (CH 3 ) 3 Si-(OSi(CH 3 ) 2 ) n -(CH 2 ) 10 -. The average value of the number of repeating units n is 19.

[1018] Compound (17)

[1019] 1 H NMR (CDCl 3 , 400 MHz) δ [ppm]: -0.01 - 0.30 (m), 0.49 - 0.53 (m, 2H), 1.20 - 1.40 (m, 14H), 1.55 - 1.68 (m, 2H), 2.13 - 2.35 (m, 2H) 3.86 - 3.89 (m, 2H), 5.05 - 5.23 (m, 2H), 5.68 - 5.84 (m, 1H).

[1020] Mix the above R-CONHCH 2 CH=CH 2 (5 g), toluene (20 mL), a xylene solution of Karstedt's catalyst (2%, 0.7 mL), aniline (0.12 g) and trimethoxysilane (1.20 mL), stir overnight at room temperature, and then concentrate under reduced pressure to obtain compound C: R-CONH-CH 2 CH 2 CH 2 Si(OCH 3 ) 3 (4.7 g). Among them, R is (CH 3 ) 3 Si-(OSi(CH 3 ) 2 ) n -(CH 2 ) 10 -. The average value of the number of repeating units n is 19.

[1021] Compound C

[1022] 1 H NMR(CDCl 3 , 400 MHz) δ [ppm]: -0.01 - 0.30 (m), 0.509 - 0.55 (m, 2H), 1.23 - 1.44 (m, 14H), 1.49 - 1.60 (m, 4H), 2.13 - 2.35 (m, 2H), 3.17 - 3.25 (m, 2H), 3.55 - 59 (m, 9H).

[1023] (Synthesis Example 18)

[1024]

[1025] Dissolve methyl 16 - formylhexadecanoate (5.7 g, 20 mmol) synthesized according to The Journal of Organic Chemistry 2019, 84, 8019 - 8026 in dichloromethane (120 mL). After cooling the reaction vessel to 0 °C with an ice bath, slowly add DAST (diethylaminosulfur trifluoride) (3.8 mL, 90%, 26 mmol) to this solution. Stir at 0 °C for 1 hour and then add water to terminate the reaction. Transfer the contents to a separatory funnel, dilute and extract with chloroform, and dry with anhydrous magnesium sulfate. Then purify by silica gel column chromatography to obtain the compound (18) in the form of a colorless oily substance (2.9 g, 48%).

[1026] Compound (18)

[1027]

[1028] 1 H NMR (400 MHz, CDCl 3 ) δ [ppm]: 5.78 (tt, J = 4.8, 49.1 Hz, 1H), 3.67 (s, 3H), 2.23 (t, J = 7.0 Hz, 2H), 1.88 - 1.72 (m, 2H), 1.70 - 1.54 (m, 2H), 1.49 - 1.37 (m, 2H), 1.38 - 1.22 (brs, 20H).

[1029] 19 F NMR (375 MHz, CDCl 3 ) δ [ppm]: -115.6 (td, J = 18.0, 49.1 Hz, 2F). (Synthesis Example 19)

[1030]

[1031] The compound (18) (900 mg, 2.9 mmol) obtained in Synthesis Example 18, allylamine (allylNH 2 )(500 mg, 8.8 mmol), and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) (400 mg, 2.9 mmol) were mixed, and the reaction vessel was heated and stirred at 50 °C for 14 hours. After cooling, the volatile components were removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound (19) in the form of a colorless solid (950 mg, 100%).

[1032] Compound (19)

[1033]

[1034] 1 H NMR (400 MHz, CDCl 3 ) δ [ppm]: 5.95 - 5.61 (m, 2H), 5.44 (s, 1H), 5.23 - 5.08 (m, 2H), 3.90 - 3.85 (m, 2H), 2.19 (t, J = 7.8 Hz, 2H), 1.88 - 1.72 (m, 2H), 1.70 - 1.60 (m, 2H), 1.49 - 1.39 (m, 2H), 1.38 - 1.22 (brs, 20H).

[1035] 19 F NMR (375 MHz, CDCl 3 ) δ [ppm]: -115.6 (td, J = 37.3, 19.9 Hz, 2F).

[1036] (Synthesis Example 20)

[1037] 0.703 g of the compound (19) CF 2 H(CH 2 ) 14 CONHCH 2 CH=CH 2 was added respectively, 10.6 mL of toluene, 0.0843 g of pyridine, 0.5 mL of a xylene solution of a Pt coordination compound containing 2% of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, and then 0.81 mL of trimethoxysilane was added, and the mixture was stirred at room temperature overnight. After that, purification was carried out to obtain 1.13 g of the following compound (20) CF 2 H(CH 2 ) 14 CONHCH 2 CH 2 CH 2 Si(OCH3 ) 3 。

[1038] Compound (20)

[1039]

[1040] 1 H NMR (CDCl 3 , 400 MHz) δ [ppm]: 0.232 - 0.407 (m), 0.689 - 0.731 (m), 1.249 - 1.726 (m), 2.086 - 2.474 (m), 3.555 - 3.675 (m), 5.448 - 5.754 (tt) (Synthesis Example 21)

[1041]

[1042] The compound (18) (900 mg, 2.9 mmol) obtained in Synthesis Example 18, diallylamine (allyl 2 NH, 630 mg, 6.5 mmol) and 1,5,7 - triazabicyclo[4.4.0]dec - 5 - ene (400 mg, 2.9 mmol) were mixed, and the reaction vessel was heated and stirred at 50 °C for 14 hours. After cooling, the volatile components were removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound (21) in the form of an orange liquid (460 mg, 43%).

[1043] Compound (21)

[1044]

[1045] 1 H NMR (400 MHz, CDCl 3 ) δ [ppm]: 5.95 - 5.63 (m, 3H), 5.27 - 5.07 (m, 4H), 3.99 (d, J = 5.9 Hz, 2H), 3.87 (d, J = 5.0 Hz, 2H), 2.30 (t, J = 7.8 Hz, 2H), 1.89 - 1.74 (m, 2H), 1.66 - 1.53 (m, 2H), 1.48 - 1.40 (m, 2H), 1.27, (d, J = 11.4 Hz, 20H).

[1046] 19 F NMR (375 MHz, CDCl 3 ) δ [ppm]: -115.62 (td, J = 38.0, 18.9 Hz, 2F).

[1047] (Synthesis Example 22)

[1048] 0.46 g of the compound (21)CF obtained in Synthesis Example 21 was added separately 2 H(CH 2 ) 14 CON(CH 2 CH=CH 2 ) 2 , 6.2 mL of toluene, 0.0489 g of pyridine, and 0.28 mL of a xylene solution of a Pt coordination compound containing 2% of 1,3 - divinyl - 1,1,3,3 - tetramethyldisiloxane were added. Then, 1.4 mL of trimethoxysilane was added, and the mixture was stirred at room temperature overnight. After that, purification was carried out to obtain 0.96 g of the following compound (22)CF having a trimethoxysilyl group at the terminal 2 H(CH 2 ) 14 CON(CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ) 2 .

[1049] Compound (22)

[1050]

[1051] 1 H NMR(CDCl 3 , 400 MHz) δ [ppm]: 0.217 - 0.282 (m), 0.599 - 0.784 (m), 1.268 - 1.379 (m), 1.677 - 1.800 (m), 2.078 - 2.669 (m), 3.379 - 3.418 (m), 3.536 - 3.616 (m), 5.468 - 5.766 (tt)

[1052] (Synthesis Example 23)

[1053]

[1054] The compound (18) (750 mg, 2.4 mmol) obtained in Synthesis Example 18, 2,2 - diallyl - 4 - penten - 1 - amine (800 mg, 4.8 mmol), and 1,5,7 - triazabicyclo[4.4.0]dec - 5 - ene (400 mg, 2.9 mmol) were mixed, and the reaction vessel was heated and stirred at 50 °C for 14 hours. After cooling, the volatile components were removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound (23) in the form of an orange liquid (460 mg, 43%).

[1055] Compound (23)

[1056]

[1057] 1 H NMR (400 MHz, CDCl 3 ) δ [ppm]: 5.95 - 5.62 (m, 4H), 5.51 (s, 1H), 5.15 - 5.05 (m, 6H), 3.20 (d, J = 6.4 Hz, 2H), 2.16 (d, J = 7.5 Hz, 2H), 2.03 (d, J = 7.3 Hz, 6H), 1.90 - 1.71 (m, 2H), 1.66 - 1.57 (m, 2H), 1.48 - 1.40 (m, 2H), 1.30 - 1.18 (m, 20H)

[1058] 19 F NMR (375 MHz, CDCl 3 ) δ [ppm]: -115.6 (td, J = 37.3, 18.9 Hz, 2F). (Synthesis Example 24)

[1059] 0.66 g of the compound (23) CF 2 H(CH 2 ) 14 CONHCH 2 C(CH 2 CH=CH 2 ) 3 obtained in Synthesis Example 23, 7.5 mL of toluene, 0.0558 g of pyridine, and 0.4 mL of a xylene solution of a Pt coordination compound containing 2% of 1,3 - divinyl - 1,1,3,3 - tetramethyldisiloxane were added respectively. Then, 1.2 mL of trimethoxysilane was added, and the mixture was stirred at room temperature overnight. After that, purification was carried out to obtain 0.97 g of the following compound (24) CF 2 H(CH 2 ) 14 CONHCH 2 C(CH 2 CH 2 CH 2 Si(OCH 3 ) 3 ) 3 .

[1060] Compound (24)

[1061]

[1062] 1 H NMR (CDCl 3, 400 MHz) δ [ppm]: 0.225 - 0.382 (m), 0.739 - 0.800 (m), 1.271 - 1.791 (m), 2.132 - 2.502 (m), 3.286 - 3.337 (m), 3.545 - 3.701 (m), 5.493 - 5.801 (tt)

[1063] (Comparative Example)

[1064] The following compounds (A) to (C) were used.

[1065] · Compound (A): KBM-3183E manufactured by Shin-Etsu Chemical Co., Ltd.

[1066] · Compound (B): Compound B

[1067] · Compound (C): Compound C

[1068] <Formation of Formed Body 1 (Including Na Intermediate Layer Forming Material)>

[1069] 2.2 g of sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Corporation) was dissolved in 24 g of distilled water to obtain an 8.4 mass% sodium hydroxide aqueous solution. 24 g of this 8.4 mass% sodium hydroxide aqueous solution was mixed with 20 g of MS gel (M.S.GEL D-100-60A (manufactured by AGC Si-Tech Co., Ltd.)) so that the sodium hydroxide aqueous solution was absorbed into the MS gel. The MS gel absorbed with the sodium hydroxide aqueous solution was dried at 25°C for 8 hours and then formed using a tablet molding machine (4 MPa, 1 minute) and fired at 1000°C for 1 hour to obtain Formed Body 1 (pellets).

[1070] <Formation of Surface Treatment Layer>

[1071] A surface treatment agent was synthesized by combining a solvent and a compound as shown in Table 1 below. The compound concentration was set to 20 wt%. In the following table, EtOH represents ethanol and HMDSO represents hexamethyldisiloxane.

[1072] [Table 1]

[1073] Example / Comparative Example Number Solvent Compound Number Example 1 EtOH 5 Example 2 EtOH 7 Example 3 EtOH 9 Example 4 EtOH 11 Example 5 EtOH 13 Example 11 EtOH 20 Example 12 EtOH 22 Example 13 EtOH 24 Comparative Example 1 EtOH A Comparative Example 2 EtOH B Comparative Example 3 HMDSO C

[1074] The surface treatment agent was vacuum-evaporated onto chemically strengthened glass (manufactured by Corning, Gorilla Glass, thickness 0.7 mm). Specifically, 0.1 g of the surface treatment agent was filled in a molybdenum boat in the vacuum evaporation apparatus, and the inside of the vacuum evaporation apparatus was evacuated to a pressure of 3.0×10 ﹣3Below Pa. After that, a 7-nm-thick silicon dioxide film is formed, and then the boat is heated by resistance heating to form a surface treatment layer. After that, a heat treatment is carried out in an oven at 150 °C for 30 minutes to obtain the surface treatment layer.

[1075] The solvent and the compound are combined as shown in Table 2 below to synthesize a surface treatment agent. The compound concentration is set at 20 wt%.

[1076] [Table 2]

[1077] Example / Comparative Example Number Solvent Compound Number Example 6 EtOH 5 Example 7 EtOH 7 Example 8 EtOH 9 Example 9 EtOH 11 Example 10 EtOH 13 Example 14 EtOH 20 Example 15 EtOH 22 Example 16 EtOH 24 Comparative Example 4 EtOH A Comparative Example 5 EtOH B Comparative Example 6 HMDSO C

[1078] The surface treatment agent is vacuum-evaporated onto chemically strengthened glass (manufactured by Corning Inc., Gorilla Glass, thickness 0.7 mm). Specifically, 0.1 g of the surface treatment agent is filled in a molybdenum boat in a vacuum evaporation apparatus, and the inside of the vacuum evaporation apparatus is evacuated to a pressure of 3.0×10 ﹣3 Pa below. After that, vapor deposition is carried out by electron beam evaporation using the molding body 1 to form a 7-nm-thick sodium-containing silicon dioxide film, and then the boat is heated by resistance heating to form a surface treatment layer. After that, a heat treatment is carried out in an oven at 150 °C for 30 minutes to obtain the surface treatment layer.

[1079] <Evaluation>

[1080] [Fingerprint removability evaluation]

[1081] For the surface treatment layer formed above, the fingerprint adhesion and fingerprint removability are evaluated according to the following steps.

[1082] The indexes for fingerprint adhesion and fingerprint removability are haze (%). The lower the haze, the more difficult it is to visually recognize the fingerprint. Among them, the haze is measured using a haze meter NDH7000SP manufactured by Nippon Denshoku Industries Co., Ltd. The substrate is set in such a way that the area of the artificial fingerprint printing completely falls within the measurement area (Φ20 mm), and the average value measured 3 times is adopted.

[1083] (Initial evaluation)

[1084] After the surface treatment layer is formed, the excess components on the surface are wiped off with ethanol, and then the haze is measured. It is denoted as Ti.

[1085] (Fingerprint adhesion evaluation)

[1086] An artificial fingerprint solution is printed on the surface treatment layer after the initial evaluation, and the haze of the printed part is measured. It is denoted as T0, and T0 - Ti is used as the fingerprint adhesion.

[1087] Among them, the composition and printing conditions of the artificial fingerprint solution are as described below.

[1088] (Preparation method of artificial fingerprint liquid)

[1089] The preparation of the artificial fingerprint liquid is carried out as described below with reference to Japanese Patent Laid-Open No. 2006-120317.

[1090] Mix 1.6 g of Kanto soil (JIS test powder 1 (11 types), Japan Powder Industry Technology Association) and 32 g of methoxypropanol (manufactured by Tokyo Chemical Industry Co., Ltd.). Then add 4 g of glyceryl trioleate (manufactured by Tokyo Chemical Industry Co., Ltd.) and stir.

[1091] (Manufacturing method of artificial fingerprint sheet)

[1092] Perform UV cleaning on a glass plate (manufactured by Corning, Gorilla Glass, thickness 0.7 mm) for 10 minutes. Spin-coat 1.1 mL of the above-prepared artificial fingerprint liquid (5000 rpm, 10 seconds) on the glass plate. Then, heat the glass at 60 °C for 3 minutes using a drying oven.

[1093] (Printing conditions)

[1094] Stamp: Silicone rubber (pressing surface Φ16 mm)

[1095] Press the stamp on the above-prepared artificial fingerprint sheet with a load of 5 kgw for 10 seconds to transfer the artificial fingerprint. Then press the stamp with the transferred artificial fingerprint on the sample for evaluating wipe-off property with a load of 5 kgw for 10 seconds to attach the artificial fingerprint liquid.

[1096] (Fingerprint wipe-off property test method)

[1097] Use a friction testing machine (manufactured by Iwamoto Seisakusho Co., Ltd.) to perform 10 wiping operations on the formed surface treatment layer under the following conditions. Then, measure the haze of the printed part. Denote it as T10, and use T10 - Ti as the fingerprint wipe-off property.

[1098] · Wiping operation:

[1099] Friction part: Bemcot M-3II (product name, manufactured by Asahi Kasei Corporation)

[1100] Moving distance (one-way): 60 mm

[1101] Moving speed: 8400 mm / minute

[1102] Load: 1000 g / 3 cm 2

[1103] The judgment criteria for evaluating fingerprint adhesion and fingerprint wipe-off property are as follows.

[1104] (Evaluation of fingerprint adhesion)

[1105] The value of T0−Ti is as follows.

[1106] Less than 5: 〇 (excellent)

[1107] 5 or more and less than 10: △ (good)

[1108] 10 or more: × (fair)

[1109] (Fingerprint removability evaluation)

[1110] The value of T10−Ti is as follows.

[1111] Less than 1: 〇 (excellent)

[1112] 1 or more and less than 2.5: △ (good)

[1113] 2.5 or more: × (fair)

[1114] [Wear resistance evaluation]

[1115] (Wear resistance test method)

[1116] After forming the surface treatment layer, wipe off the excess components on the surface, and then bring the formed surface treatment layer into contact with the following friction member. Apply a load of 5 N thereto, and reciprocate the friction member at a speed of 40 mm / second in the state where the load is applied. Measure the static contact angle (°) of water when the number of friction times is 100 times.

[1117] The contact angle is measured using a fully automatic contact angle meter DropMaster700 (manufactured by Kyowa Interface Science Co., Ltd.) in an environment of 25°C. Specifically, the substrate having the surface treatment layer to be measured is horizontally stationary, 2 μL of water is dropped onto its surface from a micro syringe, and a still image 1 second after the dropping is taken with a video microscope, thereby measuring the static contact angle. The static contact angle is measured at five different locations on the surface treatment layer of the substrate, and the average value calculated is adopted.

[1118] ·Measurement criteria

[1119] 80° or more: ◎ (excellent)

[1120] 65° or more and less than 80°: 〇 (good)

[1121] 50° or more and less than 65°: △ (fair)

[1122] Less than 50°: × (poor)

[1123] ·Friction member

[1124] Use a product in which the surface of the following silicone rubber processed product is covered with a cotton sheet impregnated with artificial sweat having the following composition as the friction member.

[1125] Silicone rubber processed product:

[1126] Process the silicone rubber stopper SR-51 manufactured by TIGERS POLYMER into a cylindrical shape with a diameter of 1 cm and a thickness of 1 cm.

[1127] Composition of artificial sweat:

[1128] Disodium hydrogen phosphate anhydrous: 2 g

[1129] Sodium chloride: 20 g

[1130] 85% Lactic acid: 2 g

[1131] Histidine hydrochloride: 5 g

[1132] Distilled water: 1 Kg

[1133] The results of the fingerprint adhesion, fingerprint wiping, and abrasion resistance evaluations are shown in Tables 3 and 4 below.

[1134] [Table 3]

[1135] Example / Comparative Example Number Evaluation before wiping T0 - Ti Evaluation after wiping T10 - Ti Evaluation after abrasion resistance test Example 1 △ △ △ Example 2 ○ ○ △ Example 3 ○ ○ △ Example 4 △ △ ○ Example 5 ○ ○ ○ Example 11 ○ ○ △ Example 12 ○ ○ △ Example 13 ○ ○ ○ Comparative Example 1 × × ○ Comparative Example 2 × × ○ Comparative Example 3 △ △ ×

[1136] [Table 4]

[1137] Example / Comparative Example Number Evaluation before wiping T0 - Ti Evaluation after wiping T10 - Ti Evaluation after abrasion resistance test Example 6 △ △ △ Example 7 ○ ○ ○ Example 8 ○ ○ ○ Example 9 △ △ ◎ Example 10 ○ ○ ◎ Example 14 ○ ○ ○ Example 15 ○ ○ ◎ Example 16 ○ ○ ◎ Comparative Example 4 × × ○ Comparative Example 5 × × ◎ Comparative Example 6 △ △ ×

[1138] Industrial applicability

[1139] The compounds of the present invention can be applied to a variety of uses.

Claims

1. A fluorine atom-containing silane compound represented by the following formula (1), characterized in that, (Rf 1 ) α1 -X A -(R Si ) α2 …(1) in the formula: Rf 1 each independently has at least one group selected from monovalent organic groups having A 1 γ11 A 2 γ12 a monovalent organic group of C−, and a monovalent organic group including a cyclic structure containing CF≡ A 1 is a fluorine atom; A 2 are each independently a hydrogen atom, a chlorine atom or a bromine atom; γ11 are each independently 1 or 2; γ12 are each independently 1 or 2; the sum of γ11 and γ12 is 3; X A are each independently a single bond, an oxygen atom or an organic group having a valence of 2 to 10; R Si is a monovalent group containing a Si atom bonded to a hydroxyl group or a hydrolyzable group; α1 is an integer from 1 to 9; and α2 is an integer from 1 to 9.

2. The fluorine atom-containing silane compound according to claim 1, characterized in that, Rf 1 is A 1 γ11 A 2 γ12 C−X B - the group shown in the formula: A 1 is a fluorine atom; A 2 are each independently a hydrogen atom, a chlorine atom or a bromine atom; γ11 are each independently 1 or 2; γ12 are each independently 1 or 2; the sum of γ11 and γ12 is 3; X B is a single bond, a divalent polysiloxane-containing group or -(CR A1 e1 H 2－e1 ) a1 -(CFH) b1 -(CH 2 ) c1 -(O) d1 - the group shown in the formula, R A1 is a monovalent organic group having A 1 γ11 A 2 γ12 C−; e1 is 1 or 2; a1 is an integer from 0 to 200; b1 is an integer from 0 to 200; c1 is an integer from 0 to 200; d1 is an integer from 0 to 200; and the order of existence of each repeating unit enclosed in parentheses with the symbols a1, b1, c1, and d1 is arbitrary.

3. The fluorine atom-containing silane compound according to claim 2, characterized in that, X B is -(CR A1 e1 H 2－e1 ) a1 -(CFH) b1 -(CH 2 ) c1 -(O) d1 - the group shown in the formula: R A1 is a monovalent organic group having A 1 γ11 A 2 γ12 C−; A 1 and A 2 The meanings of γ11, γ12, e1, a1, b1, c1 and d1 are the same as those in claim 2; the order of existence of each repeating unit enclosed in parentheses with the symbols a1, b1, c1, and d1 is arbitrary.

4. The fluorine atom-containing silane compound according to claim 2, characterized in that, X B is -(CFH) b1 -(CH 2 ) c1 -(O) d1 - the group shown in the formula: b1 and c1 have the same meanings as in claim 2; d1 is an integer from 0 to 10; and the order of existence of each repeating unit enclosed in parentheses with the symbols b1, c1, and d1 is arbitrary.

5. The fluorine atom-containing silane compound according to claim 2, characterized in that, X B is a group represented by -(CH 2 ) c1 - as shown in the formula, c1 is an integer from 0 to 30.

6. The fluorine atom-containing silane compound according to claim 2, characterized in that, X B is a group represented by -O-(CH 2 ) c1 - as shown in the formula, c1 is an integer from 0 to 30.

7. The fluorine atom-containing silane compound according to claim 2, characterized in that, X B is -(CH 2 ) g1 -SiR s 2 O(-SiR s 2 O-) n11 SiR s 2 -(CH 2 ) g1 - the group shown in the formula: R s are each independently a hydrogen atom, a hydroxyl group or a hydrocarbon group, n11 is an integer from 1 to 1500, g1 are each independently integers from 0 to 30.

8. The fluorine atom-containing silane compound according to any one of claims 1 to 7, characterized in that, A 1 γ11 A 2 γ12 C is HCF 2 -.

9. The fluorine atom-containing silane compound according to any one of claims 1 to 8, characterized in that, X A is a single bond, -(X 52 ) l5 - or the formula (X A1 ): The groups shown in the formula: X 52 Each independently is a group selected from -O-, -S-, o-phenylene, m-phenylene or p-phenylene, -CO-, -C(O)O-, -OC(O)-, -CONR 53 -, -NR 53 CO-, -O-CONR 53 -, -NR 53 CO-O-, -NR 53 CONR 53 -, -NR 53 -, - and -(CH 2 ) n5 -; R 53 Each is independently a hydrogen atom or a monovalent organic group; n5 are each independently integers from 1 to 30; l5 is an integer from 1 to 10; X a Each is independently a single bond or a divalent linking group.

10. The fluorine atom-containing silane compound according to any one of claims 1 to 9, characterized in that, R Si is a group represented by the following formula (S1), (S2), (S3), (S4) or (S5): -SiR 11 n1 R 12 3-n1 (S2) -SiR a1 k1 R b1 11 R c1 m1 (S3) -CR d1 k2 R e1 12 R f1 m2 (S4) -NR g1 k3 R h1 13 (S5) in the formula: R 11 are each independently a hydroxyl group or a hydrolyzable group; R 12 are each independently a monovalent organic group; n1 is independently an integer from 0 to 3 in each (SiR 11 n1 R 12 3-n1 ) cell; X 11 are each independently a single bond or a divalent organic group; R 13 are each independently a hydrogen atom or a monovalent organic group; t are each independently integers of 2 or more; R 14 Each independently is a hydrogen atom, a halogen atom or -X 11 -SiR 11 n1 R 12 3-n1 ; R 15 are each independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms; R a1 are each independently -Z 1 -SiR 21 p1 R 22 q1 R 23 r1 ; Z 1 each independently represents a divalent organic group; R 21 are each independently -Z 1′ -SiR 11′ p1′ R 22′ q1′ R 23′ r1′ ; R 22 are each independently a hydroxyl group or a hydrolyzable group; R 23 are each independently a monovalent organic group; p1 are each independently integers from 0 to 3; q1 are each independently integers from 0 to 3; r1 are each independently integers from 0 to 3; Z 1' each independently represents a divalent organic group; R 21' are each independently -Z 1” -SiR 22” q1” R 23” r1” ; R 22' are each independently a hydroxyl group or a hydrolyzable group; R 23' are each independently a monovalent organic group; p1' are each independently integers from 0 to 3; q1' are each independently integers from 0 to 3; r1' are each independently integers from 0 to 3; Z 1” are each independently a divalent organic group; R 22” are each independently a hydroxyl group or a hydrolyzable group; R 23” are each independently a monovalent organic group; q1” are each independently integers from 0 to 3; r1” are each independently integers from 0 to 3; R b1 are each independently a hydroxyl group or a hydrolyzable group; R c1 are each independently a monovalent organic group; k1 are each independently integers from 0 to 3; l1 are each independently integers from 0 to 3; m1 are each independently integers from 0 to 3; R d1 are each independently -Z 2 -CR 31 p2 R 32 q2 R 33 r2 ; Z 2 are each independently a single bond, an oxygen atom or a divalent organic group; R 31 are each independently -Z 2' -CR 32' q2' R 33' r2' ; R 32 are each independently -Z 3 -SiR 34 n2 R 35 3－n2 ; R 33 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group; p2 are each independently integers from 0 to 3; q2 are each independently integers from 0 to 3; r2 are each independently integers from 0 to 3; Z 2' are each independently a single bond, an oxygen atom or a divalent organic group; R 32' each independently being -Z 3 -SiR 34 n2 R 35 3－n2 ; R 33' are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group; q2' are each independently integers from 0 to 3; r2' are each independently integers from 0 to 3; Z 3 are each independently a single bond, an oxygen atom or a divalent organic group; R 34 are each independently a hydroxyl group or a hydrolyzable group; R 35 are each independently a monovalent organic group; n2 are each independently integers from 0 to 3; R e1 are each independently -Z 3 -SiR 34 n2 R 35 3－n2 ; R f1 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group; k2 are each independently integers from 0 to 3; l2 is independently an integer from 0 to 3; m2 is independently an integer from 0 to 3, R g1 and R h1 are each independently -Z 4 -SiR 11 n1 R 12 3－n1 、-Z 4 -SiR a1 k1 R b1 l1 R c1 m1 or -Z 4 -CR d1 k2 R e1 l2 R f1 m2 ; Z 4 are each independently a single bond, an oxygen atom or a divalent organic group; k3 is 1 or 2; l3 is 0 or 1; Among them, in formula (S1), (S2), (S3), (S4) or (S5), there are at least 2 Si atoms bonded with hydroxyl groups or hydrolyzable groups.

11. A surface treatment agent, characterized in that, it contains the fluorine atom-containing silane compound described in any one of claims 1 to 10.

12. The surface treatment agent according to claim 11, characterized in that, it further contains a condensate of the fluorine atom-containing silane compound described in any one of claims 1 to 10.

13. The surface treatment agent according to claim 11 or 12, characterized in that, It also contains an alcohol represented by R 90 -OH, wherein R 90 is a monovalent organic group.

14. The surface treatment agent according to any one of claims 11 to 13, characterized in that, it is used for vacuum evaporation coating.

15. The surface treatment agent according to any one of claims 11 to 13, characterized in that, it is used for wet covering.

16. A pellet, characterized in that, it contains the surface treatment agent described in any one of claims 11 to 15.

17. An article, characterized in that, it includes a substrate and a layer formed on the substrate by the fluorine atom-containing silane compound described in any one of claims 1 to 10.

18. The article according to claim 17, characterized in that, it includes an intermediate layer containing silicon oxide between the substrate and the layer.

19. The article according to claim 18, characterized in that, the intermediate layer contains alkali metal atoms.

20. The article according to claim 19, characterized in that, at least a part of the alkali metal atoms is sodium.

21. The article according to any one of claims 17 to 20, characterized in that, it is an optical component.

22. The article according to claim 21, characterized in that, it is a display.

23. Compounds represented by the following formulas (2a) to (2g), characterized in that, Rf 1’ -X B3 -X A3 -CH=CH 2 …(2b) Rf 1’ -X B4 -X A4 -Si(X A5 -CH=CH 2 ) δ3 R 95 3-δ3 …(2c) Rf 1’ -X B4 -X A4 -C(X A6 -CH=CH 2 ) δ4 R 96 3-δ4 …(2d) Rf 1’ -X B4 -X A4 -NR 97 2 …(2e) Rf 1' -X B5 -X A7 -NR 53 -R 98 …(2f) in the formula: Rf 1′ - Each independently is A 11 γ11 A 12 γ12 C - or a cyclic structure containing CF≡; A 11 is a fluorine atom; A 12 are each independently a hydrogen atom, a chlorine atom or a bromine atom; γ11 are independently 0 or 1; γ12 are independently 1 or 2; the sum of γ11 and γ12 is 3; -R 91 is hydroxy, -F, -Cl or -O-C 1-3 alkyl; X B2 is (CH 2 ) c21 , (CH 2 ) c22 -O-(CH 2 ) c23 or a divalent polysiloxane-containing group; c21, c22 and c23 are independently integers from 0 to 200; Among them, the sum of c22 and c23 is an integer from 0 to 200; Rf 1′ -X B2 - is Rf 1 -; Rf 1 - Each independently has at least one group selected from a monovalent organic group having A 1 γ11 A 2 γ12 C- and a monovalent organic group including a cyclic structure containing CF≡ X B3 is (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group; c11, c12 and c13 are independently integers from 0 to 200; Among them, the sum of c12 and c13 is an integer from 0 to 200; X A3 each independently is a single bond or C(=O)NR 53 -(CH 2 ) c14 ; R 53 is a hydrogen atom or a monovalent organic group; c14 is an integer from 0 to 30; X B4 are each independently (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group; c11, c12 and c13 are independently integers from 0 to 200; Among them, the sum of c12 and c13 is an integer from 0 to 200; Rf 1' -X B4 - equivalent to Rf 1 -; Rf 1 - Each independently has at least one group selected from a monovalent organic group having A 1 γ11 A 2 γ12 C- and a monovalent organic group including a cyclic structure containing CF≡ X A4 each independently is a single bond or C(=O)NR 53 -(CH 2 ) c15 ; c15 is an integer from 0 to 30; X A5 are each independently a single bond or a divalent organic group; R 95 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group; δ3 is an integer from 1 to 3; X A6 are each independently a single bond, an oxygen atom or a divalent organic group; R 96 are each independently a hydrogen atom, a hydroxyl group or a monovalent organic group; δ4 is an integer from 1 to 3; -R 97 are each independently represented by -R 92 -CH=CH 2 or -R 94 -Q A1 (R 92 -CH=CH 2 ) δ31 R 93 δ32 means; R 92 is a single bond, an oxygen atom or a divalent organic group; R 94 is a single bond, an oxygen atom or a divalent organic group; Q A1 are each independently N, Si, or C; R 93 is a hydrogen atom, a hydroxyl group or a monovalent organic group; δ31 and δ32 are independently integers of 1 or more; The sum of δ31 and δ32 is Q A1 valence number of -1; X B5 represented by (CH 2 ) c11 , (CH 2 ) c12 -O-(CH 2 ) c13 or a divalent polysiloxane-containing group; c11, c12 and c13 are independently integers from 0 to 200; Among them, the sum of c12 and c13 is an integer from 0 to 200; X A7 is a single bond or C(=O); -R 98 represented by -R 92 -CH=CH 2 or -R 94 -Q A1 (R 92 -CH=CH 2 ) δ31 R 93 δ32 means; -R A31 represented by -Rf 1 ; Rf 1 - Each independently has at least one group selected from monovalent organic groups having A 1 γ11 A 2 γ12 C- and monovalent organic groups including a cyclic structure containing CF≡ -R A32 consisting of -X A31 -CH=CH 2 or -X A33 -Q A2 (X A32 -CH=CH 2 ) δ41 R 36 δ42 denote; -R A33 represented by -Rf 1 , -X A31 -CH=CH 2 or -X A33 -Q A2 (X A32 -CH=CH 2 ) δ41 R 36 δ42 denote; X A31 、 X A32 and X A33 are each independently a single bond, an oxygen atom or a divalent organic group; Q A2 are independently N, Si or C respectively; R 36 is a hydrogen atom, a hydroxyl group or a monovalent organic group; δ41 and δ42 are independently integers of 1 or more; The sum of δ41 and δ42 is Q A2 valence number of - 1

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