CN117813311A

CN117813311A - Surface treating agent

Info

Publication number: CN117813311A
Application number: CN202280056054.2A
Authority: CN
Inventors: 半田晋也; 野村孝史; 松井元志; G·托尔蒂西耶; 高田昌和; 中野希望; 大向吉景; 高野真也
Original assignee: Daikin Industries Ltd
Current assignee: Daikin Industries Ltd
Priority date: 2021-08-10
Filing date: 2022-08-09
Publication date: 2024-04-02

Abstract

The present invention provides a siloxane-containing silane compound represented by the following formula (1) or (2) (wherein each symbol is as described in the specification). R is R ^S1 _α ‑X ^A ‑R ^H _β (1)，R ^H _γ ‑X ^A ‑R ^S2 ‑X ^A ‑R ^H _γ (2)。

Description

Surface treating agent

Technical Field

The present invention relates to a surface treatment agent.

Background

It is known that certain kinds of silane compounds can provide excellent water and oil repellency when used for surface treatment of a substrate (patent document 1).

Prior art literature

Patent literature

Patent document 1: japanese patent laid-open No. 2019-44179

Disclosure of Invention

Technical problem to be solved by the invention

The silane compound described in patent document 1 can provide a surface-treated layer excellent in fingerprint wiping properties, but a surface-treated layer having a higher function is still demanded.

The purpose of the present invention is to provide a surface treatment agent capable of forming a surface treatment layer excellent in fingerprint wiping properties.

Technical means for solving the technical problems

The present invention includes the following means.

[1] A siloxane-containing silane compound represented by the following formula (1) or (2).

R ^S1 _α -X ^A -R ^H _β (1)

R ^H _γ -X ^A -R ^S2 -X ^A -R ^H _γ (2)

[ in the above-mentioned, a method for producing a semiconductor device,

R ^S1 each occurrence is independently R ¹ -R ^S -R ² _q -；

R ^S2 is-O _p -R ^S -R ² _q -；

R ^S Each independently at each occurrence is a 2-valent linear organosiloxane group;

R ¹ is a hydrocarbon group;

R ² is-SiR ³ ₂ －；

R ³ Each independently at each occurrence is a hydrocarbyl group;

p is 0 or 1;

q is each independently 0 or 1;

R ^H each occurrence is independently a 1-valent group comprising a Si atom to which a hydroxyl group, a hydrolyzable group, or a 1-valent organic group is bonded;

r is as described above ^H More than 2 Si atoms bonded with hydroxyl or hydrolytic groups;

X ^A each independently is a single bond or a 2-10 valent organic group;

alpha is an integer of 1 to 9;

beta is an integer of 1 to 9;

gamma is an integer of 1 to 9. ]

[2] The siloxane-containing silane compound according to the above [1], wherein,

R ^S is- (SiR) ³ ₂ －O) _a －，

R ³ Each independently at each occurrence is a hydrocarbyl group,

a is 2 to 1500.

[3]As described above [1]]Or [2]]The siloxane-containing silane compound, wherein R ³ Each occurrence of which is independently C which may be substituted by a halogen atom _1－6 Alkyl or aryl.

[4]As described above in the above [1]]～[3]The siloxane-containing silane compound according to any one of, wherein R ³ Each occurrence is independently methyl or phenyl.

[5] The siloxane-containing silane compound according to any one of [1] to [4], wherein a is 10 to 500.

[6]As described above [1]]～[5]The siloxane-containing silane compound according to any one of, wherein R ^H Is a group represented by the following formula (S1), (S2), (S3) or (S4).

-SiR ^a1 _k1 R ^b1 ₁₁ R ^c1 _m1 (S2)

-CR ^d1 _k2 R ^e1 ₁₂ ^Rf1 _m2 (S3)

-NR ^g1 R ^h1 (S4)

[ in the above-mentioned, a method for producing a semiconductor device,

R ¹¹ each of which is independently a hydroxyl group or a hydrolyzable group at each occurrence;

R ¹² at each occurrence is independentlyThe standing place is a 1-valent organic group;

n1 is defined in each (SiR ¹¹ _n1 R ¹² _3－n1 ) Each of the units is independently an integer of 0 to 3;

X ¹¹ each independently at each occurrence is a single bond or a 2-valent organic group;

R ¹³ each occurrence of which is independently a hydrogen atom or a 1-valent organic group;

t is independently an integer of 2 or more for each occurrence;

R ¹⁴ each occurrence of which is independently a hydrogen atom, a halogen atom or-X ¹¹ －SiR ¹¹ _n1 R ¹² _3－n1 ；

R ¹⁵ Each occurrence of which is independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkyleneoxy group having 1 to 6 carbon atoms;

R ^a1 each occurrence is independently-Z ¹ －SiR ²¹ _p1 R ²² _q1 R ²³ _r1 ；

Z ¹ Each independently at each occurrence a 2-valent organic group;

R ²¹ each occurrence is independently-Z ^1′ －SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ；

R ²² Each of which is independently a hydroxyl group or a hydrolyzable group at each occurrence;

R ²³ each independently at each occurrence is a 1-valent organic group;

p1 is independently at each occurrence an integer from 0 to 3;

q1 is independently at each occurrence an integer from 0 to 3;

r1 is independently at each occurrence an integer from 0 to 3;

Z ^1′ each independently at each occurrence a 2-valent organic group;

R ^21′ At each occurrence ofAre each independently-Z ^1″ －SiR ^22″ _q1″ R ^23″ _r1″ ；

R ^22′ Each of which is independently a hydroxyl group or a hydrolyzable group at each occurrence;

R ^23′ each independently at each occurrence is a 1-valent organic group;

p1' is independently at each occurrence an integer from 0 to 3;

q1' is independently at each occurrence an integer from 0 to 3;

r1' is independently at each occurrence an integer from 0 to 3;

Z ^1″ each independently at each occurrence a 2-valent organic group;

R ^22″ each of which is independently a hydroxyl group or a hydrolyzable group at each occurrence;

R ^23″ each independently at each occurrence is a 1-valent organic group;

q1 "is independently at each occurrence an integer from 0 to 3;

r1' is independently at each occurrence an integer from 0 to 3;

R ^b1 each of which is independently a hydroxyl group or a hydrolyzable group at each occurrence;

R ^c1 each independently at each occurrence is a 1-valent organic group;

k1 is independently at each occurrence an integer from 0 to 3;

l1 is independently at each occurrence an integer from 0 to 3;

m1 is independently at each occurrence an integer from 0 to 3;

R ^d1 each occurrence is independently-Z ² －CR ³¹ _p2 R ³² _q2 R ³³ _r2 ；

Z ² Each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group;

R ³¹ Each occurrence is independently-Z ^2′ －CR ^32′ _q2′ R ^33′ _r2′ ；

R ³² Each occurrence is independently-Z ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 ；

R ³³ Each occurrence of which is independently a hydrogen atom, a hydroxyl group, or a 1-valent organic group;

p2 is independently at each occurrence an integer from 0 to 3;

q2 is independently at each occurrence an integer from 0 to 3;

r2 is independently at each occurrence an integer from 0 to 3;

Z ^2′ each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group;

R ^32′ each occurrence is independently-Z ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 ；

R ^33′ Each occurrence of which is independently a hydrogen atom, a hydroxyl group, or a 1-valent organic group;

q2' is independently at each occurrence an integer from 0 to 3;

r2' is independently at each occurrence an integer from 0 to 3;

Z ³ each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group;

R ³⁴ each of which is independently a hydroxyl group or a hydrolyzable group at each occurrence;

R ³⁵ each independently at each occurrence is a 1-valent organic group;

n2 is independently at each occurrence an integer from 0 to 3;

R ^e1 each occurrence is independently-Z ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 ；

R ^f1 Each occurrence of which is independently a hydrogen atom, a hydroxyl group, or a 1-valent organic group;

k2 is independently at each occurrence an integer from 0 to 3;

l2 is independently at each occurrence an integer from 0 to 3;

m2 is independently at each occurrence an integer from 0 to 3;

R ^g1 and R is ^h1 Each occurrence is 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 Each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group;

wherein at least 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded are present in the formulas (S1), (S2), (S3) and (S4). ]

[7] The siloxane-containing silane compound according to the above [6], wherein the group represented by the above formula (S1) is a group represented by the following formula (S1-b).

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

[8]As described above [6]]The siloxane-containing silane compound, wherein R ^H Each occurrence is independently a group represented by the formula (S2), (S3) or (S4).

[9]As described above [6]]The siloxane-containing silane compound, wherein R ^H Each occurrence of which is independently a group represented by the formula (S2) or (S3).

[10]As described above [6]]The siloxane-containing silane compound, wherein R ^H Each occurrence is independently a group represented by the formula (S3) or (S4).

[11]As described above [6]]The siloxane-containing silane compound, wherein，R ^H Each occurrence of which is independently a group represented by the formula (S3).

[12] The siloxane-containing silane compound according to any one of the above [1] to [11], wherein α, β and γ are 1.

[13]As described above [1]]～[12]The siloxane-containing silane compound according to any one of, wherein X ^A Is a single bond or of the formula: - (R) ⁵¹ ) _p5 －(X ⁵¹ ) _q5 -the shown 2-valent organic group.

[ in the above-mentioned, a method for producing a semiconductor device,

R ⁵¹ is a single bond, - (CH) ₂ ) _s5 Either ortho-, meta-or para-phenylene,

s5 is an integer of 1 to 20,

X ⁵¹ is- (X) ⁵² ) _l5 －，

X ⁵² Each occurrence is independently selected from the group consisting of-O-, -S-, O-phenylene m-phenylene or p-phenylene, -CO-, -C (O) O-, -CONR ⁵⁴ －、－O－CONR ⁵⁴ －、－NR ⁵⁴ -and- (CH) ₂ ) _n5 The group in (c) is a group,

R ⁵⁴ each independently at each occurrence a hydrogen atom or a 1-valent organic group,

n5 is independently an integer of 1 to 20 for each occurrence,

l5 is an integer of 1 to 10,

p5 is either 0 or 1 and,

q5 is either 0 or 1 and,

here, at least one of p5 and q5 is 1, and the order in which the repeating units p5 or q5 are present and bracketed is arbitrary. ]

[14]As described above [1]]～[12]The siloxane-containing silane compound according to any one of, wherein X ^A Are each independently a single bond, C _1－20 Alkylene, - (CH) ₂ ) _s5 －X ⁵³ －、－X ⁵³ －(CH ₂ ) _t5 -or- (CH) ₂ ) _s5 －X ⁵³ －(CH ₂ ) _t5 -shownA 2-valent organic group.

[ in the above-mentioned, a method for producing a semiconductor device,

X ⁵³ is a single bond, -O-, -CO-, -CONR ⁵⁴ －、－O－CONR ⁵⁴ －、－O－(CH ₂ ) _u5 －CONR ⁵⁴ -or-O- (CH) ₂ ) _u5 －CO－，

R ⁵⁴ Each occurrence of which is independently a hydrogen atom, phenyl group, C _1－6 Alkyl (preferably methyl) or a group containing an oxyalkylene group having 1 to 10 carbon atoms,

s5 is an integer of 1 to 20,

t5 is an integer of 1 to 20,

u5 is an integer of 1 to 20. ]

[15]As described above [1 ]]～[12]The siloxane-containing silane compound according to any one of, wherein X ^A Each independently is- (CH) ₂ ) _s5 －O－(CH ₂ ) _t5 －、－(CH ₂ ) _s5 －CONR ⁵⁴ －(CH ₂ ) _t5 －、－(CH ₂ ) _s5 －O－(CH ₂ ) _u5 -CO-or- (CH) ₂ ) _s5 －O－(CH ₂ ) _u5 －CONR ⁵⁴ －(CH ₂ ) _t5 -the shown 2-valent organic group.

[ in the above-mentioned, a method for producing a semiconductor device,

s5 is an integer of 1 to 20,

t5 is an integer of 1 to 20,

u5 is an integer of 1 to 20. ]

[16]As described above [1 ]]～[11]The siloxane-containing silane compound according to any one of, wherein X ^A Each independently is a 3 to 10 valent organic group.

[17]As described above [1 ]]～[11]The siloxane-containing silane compound according to any one of, wherein X ^A Each independently represents a group represented by the following formula.

[ wherein X is ^a Each independently is a single bond or a 2-valent organic group.]

[18]As described above [17 ]]The siloxane-containing silane compound, wherein X ^a Each independently is of the formula: - (CX) ¹²¹ X ¹²² ) _x1 －(X ^a1 ) _y1 －(CX ¹²³ X ¹²⁴ ) _z1 -the group shown.

[ in the above-mentioned, a method for producing a semiconductor device,

X ¹²¹ ～X ¹²⁴ H, OH OR-OSi (OR) ¹²¹ ) ₃ (wherein R is ¹²¹ Independently alkyl groups having 1 to 4 carbon atoms),

X ^a1 is-C (=O) NH-, -NHC (=O) -, -O-, -C (=O) O-, -OC (=O) O-, -NHC (=O) NH-, -NR ¹²² －、－C(＝O)－NR ¹²² －、－NR ¹²² -C (=o) -or S,

R ¹²² is C _1－6 Is used for the formation of a hydrocarbon chain,

x1 is an integer of 0 to 10,

y1 is either 0 or 1 and,

z1 is an integer of 1 to 10. ]

[19] A composition comprising the siloxane-containing silane compound according to any one of [1] to [18 ].

[20] A composition comprising at least one compound selected from the group consisting of the siloxane-containing silane compounds according to any one of [1] to [18] and a condensate obtained by condensing at least a part of the siloxane-containing silane compounds.

[21]As described above [19]Or [20]]The composition of any one of claims, further comprising a compound selected from R ⁷¹ OR ⁷² 、R ⁷³ _n8 C ₆ H _6－n8 、R ⁷⁴ R ⁷⁵ R ⁷⁶ Si－(O－SiR ⁷⁷ R ⁷⁸ ) _m8 －R ⁷⁹ Sum (OSiR) ⁷⁷ R ⁷⁸ ) _m9 Solvents in the compounds shown.

[ in the above-mentioned, a method for producing a semiconductor device,

R ⁷¹ ～R ⁷⁹ each independently represents a monovalent organic group having 1 to 10 carbon atoms,

m8 is an integer of 1 to 6,

m9 is an integer of 3 to 8,

n8 is an integer of 0 to 6. ]

[22]As described above [21]]The composition comprises the solvent R ⁷⁴ R ⁷⁵ R ⁷⁶ Si－(O－SiR ⁷⁷ R ⁷⁸ ) _m8 －R ⁷⁹ 。

[23] The composition according to the above [21] or [22], wherein the solvent is hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane or decamethylcyclopentasiloxane.

[24] The composition according to any one of the above [19] to [23], which is a surface treatment agent.

[25] The composition as described in the above [19] or [24], which is used for vacuum evaporation.

[26] The composition as described in [19] or [24] above, which is used for wet coverage.

[27] A pellet comprising the composition of any one of [19] to [25 ].

[28] An article, comprising: a substrate, and a layer formed on the substrate from the siloxane-containing silane compound according to any one of [1] to [18] or the composition according to any one of [19] to [26 ].

[29] The article according to item [28] above, which is an optical component.

[30] The article according to [28] above, which is a display.

[31] A compound represented by the following formula (1-a) or (2-a).

R ^S1 -X ^B (1-a)

X ^B -R ^S2 -X ^B (2-a)

[ in the above-mentioned, a method for producing a semiconductor device,

R ^S1 each occurrence is independently R ¹ －R ^S －R ² _q －；

R ^S2 is-O _p －R ^S －R ² _q －；

R ¹ is a hydrocarbon group;

R ² is-SiR ³ ₂ －；

R ³ Each independently at each occurrence is a hydrocarbyl group;

p is 0 or 1;

q is each independently 0 or 1;

X ^B each independently is- (CH) ₂ ) _s6 －X ⁵³ －X ⁵⁴ 、－X ⁵³ －(CH ₂ ) _t6 －X ⁵⁴ Or- (CH) ₂ ) _s6 －X ⁵³ －(CH ₂ ) _t6 －X ⁵⁴ 。

(in the formula (I),

X ⁵³ is-O-, -CO-, -CONR ⁷⁴ －、－O－CONR ⁷⁴ －、－O－(CH ₂ ) _u6 －CONR ⁷⁴ -or-O- (CH) ₂ ) _u6 -CO-, a single bond,

X ⁵⁴ is R ⁷⁵ 、－NR ⁷⁵ ₂ 、－SiR ⁷⁵ ₂ R ⁷⁶ 、－SiR ⁷⁵ ₃ 、－CR ⁷⁵ ₂ R ⁷⁵ 、－CR ⁷⁵ ₃ 、－SiCl ₂ R ⁷⁶ 、－SiCl ₃ Or (b)

R ⁷⁵ is-CH=CH ₂ or-CH ₂ －CH＝CH ₂ ，

R ⁷⁶ Is an organic group having a valence of 1,

R ⁷⁴ at each occurrenceAre each independently a hydrogen atom, a phenyl group, or a C _1－6 Alkyl or a group containing an oxyalkylene group having 1 to 10 carbon atoms,

s6 is an integer of 1 to 20,

t6 is an integer of 1 to 20,

u6 is an integer of 1 to 20. ) ]

[32]As described above [31]The compound, wherein X ⁵³ is-CONR ⁷⁴ －。

[33]As described above [31]The compound, wherein X ⁵⁴ is-Si (CH) ₂ CH＝CH ₂ ) ₃ or-SiCl ₃ 。

[34]As described above [31]The compound, wherein X ⁵⁴ Is that

[35]As described above [31]Said compound wherein, -X ⁵³ －X ⁵⁴ is-CON (CH) ₂ CH＝CH ₂ ) ₂ 、－CONHCH ₂ C(CH ₂ CH＝CH ₂ ) ₃ 。

Effects of the invention

According to the present invention, there is provided a surface treatment agent capable of forming a surface treatment layer excellent in fingerprint wiping performance.

Detailed Description

As used in this specification, "1 valent organic group" refers to a carbon-containing 1 valent group. The 1-valent organic group is not particularly limited, and may be a hydrocarbon group or a derivative thereof. The derivative of the hydrocarbon group means a group having 1 or more than 1 of N, O, S, si, amide group, sulfonyl group, siloxane group, carbonyl group, carbonyloxy group, etc. at the end of the hydrocarbon group or in the molecular chain. In the case of being merely referred to as an "organic group", 1-valent organic group is meant. The term "2 to 10 valent organic group" means a carbon-containing 2 to 10 valent group. The 2-to 10-valent organic group is not particularly limited, and examples thereof include 2-to 10-valent groups having 1 to 9 hydrogen atoms further separated from the organic group. For example, the 2-valent organic group is not particularly limited, and a 2-valent group having 1 hydrogen atom further separated from the organic group may be exemplified.

As used herein, "hydrocarbon group" is a group containing carbon and hydrogen, and refers to a group that has been separated from a hydrocarbon by 1 hydrogen atom. The hydrocarbon group is not particularly limited, and examples thereof include C which may be substituted with 1 or more substituents _1－20 Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The "aliphatic hydrocarbon group" may be any of linear, branched, and cyclic, or may be any of saturated or unsaturated. In addition, the hydrocarbon group may contain 1 or more ring structures.

In the case of use in the present specification, the substituent for the "hydrocarbon group" is not particularly limited, and examples thereof include C selected from halogen atoms and optionally substituted with 1 or more halogen atoms _1－6 Alkyl, C _2－6 Alkenyl, C _2－6 Alkynyl, C _3－10 Cycloalkyl, C _3－10 Unsaturated cycloalkyl, 5-10 membered heterocyclic group, 5-10 membered unsaturated heterocyclic group, C _6－10 Aryl and 1 or more than 1 group in 5-10 membered heteroaryl.

As used herein, "hydrolyzable group" refers to a group capable of undergoing a hydrolysis reaction, that is, a group that can be detached from the main skeleton of a compound by a hydrolysis reaction. Examples of the hydrolyzable group include-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO, halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), and the like.

The compound of the present invention is a siloxane-containing silane compound represented by the following formula (1) or (2).

R ^S1 _α -X ^A -R ^H _β (1)

R ^H _γ -X ^A -R ^S2 -X ^A -R ^H _γ (2)

[ in the above-mentioned, a method for producing a semiconductor device,

R ^S1 each occurrence is independently R ¹ －R ^S －R ² _q －；

R ^S2 is-O _p －R ^S －R ² _q －；

R ¹ is a hydrocarbon group;

R ² is-SiR ³ ₂ －；

R ³ Each independently at each occurrence is a hydrocarbyl group;

p is 0 or 1;

q is each independently 0 or 1;

X ^A each independently is a single bond or a 2-10 valent organic group;

alpha is an integer of 1 to 9;

beta is an integer of 1 to 9;

gamma is an integer of 1 to 9. ]

R is as described above ^S Each occurrence is independently a 2-valent linear organosiloxane group. Here, the 2-valent linear organosiloxane group means the main skeleton of the siloxane (-SiR) ₂ －O－SiR ₂ (-) is a linear organosiloxane group, and the R group bonded to the Si atom may be linear or branched.

In a preferred mode, R ^S Is of the formula: - (SiR) ³ ₂ －O) _a -the group shown.

[ in the above-mentioned, a method for producing a semiconductor device,

R ³ each independently at each occurrence is a hydrocarbyl group,

a is 2 to 1500.]

R is as described above ³ Each occurrence is independently a hydrocarbyl group. The hydrocarbon group may have a substituent.

R ³ Each occurrence is independently preferably an unsubstituted hydrocarbon group or a hydrocarbon group substituted with a halogen atom. The halogen atom is preferably a fluorine atom.

R ³ Each occurrence is independently preferably C which may be substituted by a halogen atom _1－6 Alkyl or aryl, more preferably C _1－6 Alkyl or aryl.

The above C _1－6 The alkyl group may be linear or branched, and is preferably linear. C (C) _1－6 Alkyl is preferably C _1－3 Alkyl groups, more preferably methyl groups.

The aryl group is preferably phenyl.

In one embodiment, R ³ Each occurrence is independently C _1－6 Alkyl, preferably C _1－3 Alkyl groups, more preferably methyl groups.

In another mode, R ³ Is phenyl.

In another mode, R ³ Each occurrence is independently methyl or phenyl, preferably methyl.

The a is 2 to 1500.a is preferably 5 or more, more preferably 10 or more, still more preferably 15 or more, and may be, for example, 30 or more or 50 or more. a is preferably 1000 or less, more preferably 500 or less, still more preferably 200 or less, still more preferably 150 or less, and may be, for example, 100 or less or 80 or less.

a is preferably 5 to 1000, more preferably 10 to 500, still more preferably 15 to 200, still more preferably 15 to 150.

R is as described above ¹ Is hydrocarbon radical, meaning is as defined above for R ³ The same applies.

R ¹ Preferably C which may be substituted by halogen atoms _1－6 Alkyl or aryl, more preferably C _1－6 Alkyl or aryl.

In one embodiment, R ¹ Is C _1－6 Alkyl, preferably C _1－3 Alkyl, more preferably methyl.

In another mode, R ¹ Is phenyl.

In another mode, R ¹ Methyl or phenyl, preferably methyl.

The above p is independently 0 or 1 at each occurrence. In one embodiment, p is 0. In another embodiment, p is 1.

Each occurrence of q is independently 0 or 1. In one embodiment, q is 0. In another embodiment, q is 1.

In one embodiment, p is 0 and q is 1.

R is as described above ^H Each occurrence of which is independently a 1-valent group comprising a Si atom to which a hydroxyl group, a hydrolyzable group or a 1-valent organic group is bonded, at R ^H There are more than 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.

In a preferred mode, R ^H Is a group represented by the following formula (S1), (S2), (S3) or (S4).

-SiR ^a1 _k1 R ^b1 ₁₁ R ^c1 _m1 (S2)

-CR ^d1 _k2 R ^e1 ₁₂ R ^f1 _m2 (S3)

-NR ^g1 R ^h1 (S4)

[ in the above-mentioned, a method for producing a semiconductor device,

R ¹² Each independently at each occurrence is a 1-valent organic group;

R ¹³ each occurrence of which is independently a hydrogen atom or a 1-valent organic group；

t is independently an integer of 2 or more for each occurrence;

R ^a1 each occurrence is independently-Z ¹ －SiR ²¹ _p1 R ²² _q1 R ²³ r ₁ ；

Z ¹ Each independently at each occurrence a 2-valent organic group;

R ²³ each independently at each occurrence is a 1-valent organic group;

p1 is independently at each occurrence an integer from 0 to 3;

q1 is independently at each occurrence an integer from 0 to 3;

r1 is independently at each occurrence an integer from 0 to 3;

Z ^1′ each independently at each occurrence a 2-valent organic group;

R ^21′ each occurrence is independently-Z ^1″ －SiR ^22″ _q1″ R ^23″ _r1″ ；

R ^23′ Each independently at each occurrence is a 1-valent organic group;

p1' is independently at each occurrence an integer from 0 to 3;

q1' is independently at each occurrence an integer from 0 to 3;

r1' is independently at each occurrence an integer from 0 to 3;

Z ^1″ each independently at each occurrence a 2-valent organic group;

R ^23″ each independently at each occurrence is a 1-valent organic group;

q1 "is independently at each occurrence an integer from 0 to 3;

r1' is independently at each occurrence an integer from 0 to 3;

R ^c1 each independently at each occurrence is a 1-valent organic group;

k1 is independently at each occurrence an integer from 0 to 3;

l1 is independently at each occurrence an integer from 0 to 3;

m1 is independently at each occurrence an integer from 0 to 3;

p2 is independently at each occurrence an integer from 0 to 3;

q2 is independently at each occurrence an integer from 0 to 3;

r2 is independently at each occurrence an integer from 0 to 3;

q2' is independently at each occurrence an integer from 0 to 3;

r2' is independently at each occurrence an integer from 0 to 3;

R ³⁵ each independently at each occurrence is a 1-valent organic group;

n2 is independently at each occurrence an integer from 0 to 3;

k2 is independently at each occurrence an integer from 0 to 3;

l2 is independently at each occurrence an integer from 0 to 3;

m2 is independently at each occurrence an integer from 0 to 3.

In the above formula, R ¹¹ Each occurrence is independently a hydroxyl group or a hydrolyzable group.

R ¹¹ Preferably independently at each occurrence a hydrolyzable group.

R ¹¹ Preferably independently at each occurrence-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO or halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), more preferably-OR ^h (i.e., alkoxy). As R ^h Examples of the method include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc.; substituted alkyl groups such as chloromethyl. Of these, alkyl groups are preferable, unsubstituted alkyl groups are particularly preferable, and methyl or ethyl groups are more preferable. In one embodiment R ^h Methyl, in another mode R ^h Is ethyl.

In the above formula, R ¹² Each occurrence is independently a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

At R ¹² In which the 1-valent organic group is preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl groups are more preferably methyl groups.

In the above formula, n1 is defined in each (SiR ¹¹ _n1 R ¹² _3－n1 ) Each unit is independently an integer of 0 to 3. Wherein at least 2 (SiR) wherein n1 is 1 to 3 are present in the formula (S1) ¹¹ _n1 R ¹² _3－n1 ) A unit. In other words, in the formula (S1), there are at least 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded.

n1 is defined in each (SiR ¹¹ _n1 R ¹² _3－n1 ) The units are each independently preferably an integer of 1 to 3, more preferably 2 to 3, and still more preferably 3.

In the above formula, X ¹¹ Each occurrence is independently a single bond or a 2-valent organic group. The 2-valent organic group is preferably-R ²⁸ －O _x －R ²⁹ - (wherein R is ²⁸ And R is ²⁹ Each occurrence is independently a single bond or C _1－20 Alkylene, x is 0 or 1). The C is _1－20 The alkylene group may be linear or branched, and is preferably linear. The C is _1－20 Alkylene is preferably C _1－10 Alkylene, more preferably C _1－6 Alkylene, further preferably C _1－3 An alkylene group.

In one embodiment, X ¹¹ Each occurrence is independently-C _1－6 alkylene-O-C _1－6 alkylene-or-O-C _1－6 Alkylene-.

In a preferred mode, X ¹¹ C independently at each occurrence is a single bond or a straight chain _1－6 Alkylene, preferably C, singly or in linear form _1－3 Alkylene, more preferably C, singly or in straight chain _1－2 Alkylene, further preferably straight chain C _1－2 An alkylene group.

In the above formula, R ¹³ Each occurrence of which is independently a hydrogen atom or a 1-valent organic group. The 1-valent organic group is preferably C _1－20 An alkyl group.

In a preferred mode, R ¹³ Each occurrence of which is independently a hydrogen atom or a straight chain C _1－6 Alkyl radicals, preferably hydrogen atoms or straight-chain C _1－3 Alkyl groups are preferably hydrogen atoms or methyl groups.

In the above formula, R ¹⁵ Each occurrence of which is independently a single bond, an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkylene group having 1 to 6 carbon atomsAn oxy group.

In one embodiment, R ¹⁵ Each occurrence of which is independently an oxygen atom, an alkylene group having 1 to 6 carbon atoms or an alkyleneoxy group having 1 to 6 carbon atoms.

In a preferred mode, R ¹⁵ Is a single bond.

In the above formula, t is an integer of 2 or more independently for each occurrence.

In a preferred embodiment, t is each occurrence independently an integer from 2 to 10, preferably an integer from 2 to 6.

In the above formula, R ¹⁴ Each occurrence of which is 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 mode, R ¹⁴ Is a hydrogen atom.

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

[ formula, R ¹¹ 、R ¹² 、R ¹³ 、X ¹¹ And n1 has the same meaning as described in the above formula (S1);

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, at each occurrence;

the order of presence of the repeating units denoted by t1 and t2 and bracketed in the formula is arbitrary. ]

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

[ formula, R ¹¹ 、R ¹² 、R ¹³ 、X ¹¹ Containing n1 and tThe meaning is the same as that described in the above formula (S1).]

In the above formula, R ^a1 Each occurrence is independently-Z ¹ －SiR ²¹ _p1 R ²² _q1 R ²³ _r1 。

The above Z ¹ Each occurrence of which is independently an oxygen atom or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ¹ Right side of the structure of (1) and (SiR) ²¹ _p1 R ²² _q1 R ²³ _r1 ) And (5) combining.

In a preferred mode, Z ¹ Is a 2-valent organic group.

In a preferred mode, Z ¹ Not including with Z ¹ The bonded Si atoms form siloxane bonds. Preferably in the formula (S2) (Si-Z ¹ -Si) contains no siloxane bonds.

The above Z ¹ Preferably C _1－6 Alkylene, - (CH) ₂ ) _z1 －O－(CH ₂ ) _z2 - (wherein z1 is an integer of 0 to 6, for example an integer of 1 to 6, and z2 is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z3 -phenylene- (CH) ₂ ) _z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6), and z4 is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ¹ Is C _1－6 Alkylene or- (CH) ₂ ) _z3 -phenylene- (CH) ₂ ) _z4 -, preferably-phenylene- (CH) ₂ ) _z4 －。

In another preferred embodiment, Z is as defined above ¹ Is C _1－3 An alkylene group. In one embodiment Z ¹ Can be-CH ₂ CH ₂ CH ₂ -. In another mode Z ¹ Can be-CH ₂ CH ₂ －。

R is as described above ²¹ Each occurrence is independently-Z ^1′ －SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ 。

The above Z ^1′ Each occurrence of which is independently an oxygen atom or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ^1′ Right side of the structure of (1) and (SiR) ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ) And (5) combining.

In a preferred mode, Z ^1′ Is a 2-valent organic group.

In a preferred mode, Z ^1′ Not including with Z ^1′ The bonded Si atoms form siloxane bonds. Preferably in the formula (S2) (Si-Z ^1′ -Si) contains no siloxane bonds.

The above Z ^1′ Preferably C _1－6 Alkylene, - (CH) ₂ ) _z1′ －O－(CH ₂ ) _z2′ - (wherein z1 'is an integer of 0 to 6, for example an integer of 1 to 6, and z2' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z3′ -phenylene- (CH) ₂ ) _z4′ - (wherein z3 'is an integer of 0 to 6, for example, an integer of 1 to 6), and z4' is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ^1′ Is C _1－6 Alkylene or- (CH) ₂ ) _z3′ -phenylene- (CH) ₂ ) _z4′ -, preferably-phenylene- (CH) ₂ ) _z4′ －。

In another preferred embodiment, Z is as defined above ^1′ Is C _1－3 An alkylene group. In one embodiment Z ^1′ Can be-CH ₂ CH ₂ CH ₂ -. In another mode Z ^1′ Can be-CH ₂ CH ₂ －。

R is as described above ^21′ Each occurrence is independently-Z ^1″ －SiR ^22″ _q1″ R ^23″ _r1″ 。

The above Z ^1″ Each occurrence of which is independently an oxygen atom or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ^1″ Right side of the structure of (1) and (SiR) ^22″ _q1″ R ^23″ _r1″ ) And (5) combining.

In a preferred mode, Z ^1″ Is a 2-valent organic group.

In a preferred mode, Z ^1″ Not including with Z ^1″ The bonded Si atoms form siloxane bonds. Preferably in the formula (S2) (Si-Z ^1″ -Si) contains no siloxane bonds.

The above Z ^1″ Preferably C _1－6 Alkylene, - (CH) ₂ ) _z1″ －O－(CH ₂ ) _z2″ - (wherein z1 'is an integer of 0 to 6, for example an integer of 1 to 6, and z 2' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z3″ -phenylene- (CH) ₂ ) _z4″ - (wherein z3 "is an integer of 0 to 6, for example, an integer of 1 to 6), and z 4" is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ^1″ Is C _1－6 Alkylene or- (CH) ₂ ) _z3″ -phenylene- (CH) ₂ ) _z4″ -, preferably-phenylene- (CH) ₂ ) _z4″ -. At Z ^1″ When such a group is used, the light resistance, particularly ultraviolet resistance, can be further improved.

In another preferred modeThe above Z ^1″ Is C _1－3 An alkylene group. In one embodiment, Z ^1″ Can be-CH ₂ CH ₂ CH ₂ -. In another mode, Z ^1″ Can be-CH ₂ CH ₂ －。

R is as described above ^22″ Each occurrence is independently a hydroxyl group or a hydrolyzable group.

R is as described above ^22″ Preferably independently at each occurrence a hydrolyzable group.

R is as described above ^22″ Preferably independently at each occurrence-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO or halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), more preferably-OR ^h (i.e., alkoxy). As R ^h Examples of the method include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc.; substituted alkyl groups such as chloromethyl. Of these, alkyl groups are preferable, unsubstituted alkyl groups are particularly preferable, and methyl or ethyl groups are more preferable. In one embodiment R ^h Methyl, in another mode R ^h Is ethyl.

R is as described above ^23″ Each occurrence is independently a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

The above R ^23″ In which the 1-valent organic group is preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl groups are more preferably methyl groups.

Each occurrence of q1 "is independently an integer of 0 to 3, and each occurrence of r 1" is independently an integer of 0 to 3. Wherein the sum of q1 'and r 1' is within (SiR ^22″ _q1″ R ^23″ _r1″ ) The number of the units is 3.

The above q 1' is represented by the formula (SiR) ^22″ _q1″ R ^23″ _r1″ ) The units are each independently preferably an integer of 1 to 3, more preferably 2 to 3, furtherPreferably 3.

R is as described above ^22′ Each occurrence is independently a hydroxyl group or a hydrolyzable group.

R ^22′ Preferably independently at each occurrence a hydrolyzable group.

R ^22′ Preferably independently at each occurrence-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO or halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), more preferably-OR ^h (i.e., alkoxy). As R ^h Examples of the method include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc.; substituted alkyl groups such as chloromethyl. Of these, alkyl groups are preferable, unsubstituted alkyl groups are particularly preferable, and methyl or ethyl groups are more preferable. In one embodiment R ^h Methyl, in another mode R ^h Is ethyl.

R is as described above ^23′ Each occurrence is independently a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

At R ^23′ In which the 1-valent organic group is preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl groups are more preferably methyl groups.

The above-mentioned p1' is independently an integer of 0 to 3 at each occurrence, q1' is independently an integer of 0 to 3 at each occurrence, and r1' is independently an integer of 0 to 3 at each occurrence. Wherein the sum of p ', q1' and r1' is within (SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ) The number of the units is 3.

In one embodiment, p1' is 0.

In one embodiment, p1' is defined at each (SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ) Each of the units may be independently an integer of 1 to 3, an integer of 2 to 3, or 3. In a preferred embodiment, p1' is 3.

In one embodiment, q1' is defined in each (SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ) Each unit is independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

In one embodiment, p1 'is 0 and q1' is present at each (SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ) Each unit is independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

R is as described above ²² Each occurrence is independently a hydroxyl group or a hydrolyzable group.

R ²² Preferably independently at each occurrence a hydrolyzable group.

R ²² Preferably independently at each occurrence-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO or halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), more preferably-OR ^h (i.e., alkoxy). As R ^h Examples of the method include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc.; substituted alkyl groups such as chloromethyl. Of these, alkyl groups are preferable, unsubstituted alkyl groups are particularly preferable, and methyl or ethyl groups are more preferable. In one embodiment R ^h Methyl, in another mode R ^h Is ethyl.

R is as described above ²³ Each occurrence is independently a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

At R ²³ In which the 1-valent organic group is preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl groups are more preferably methyl groups.

P1 is an integer of 0 to 3 independently at each occurrence, q1 is an integer of 0 to 3 independently at each occurrence, and r1 is an integer of 0 to 3 independently at each occurrence. Wherein p1, qThe sum of 1 and r1 is in (SiR ²¹ _p1 R ²² _q1 R ²³ _r1 ) The number of the units is 3.

In one embodiment, p1 is 0.

In one embodiment, p1 is found in each (SiR ²¹ _p1 R ²² _q1 R ²³ _r1 ) The units are each independently an integer of 1 to 3, an integer of 2 to 3, or 3. In a preferred embodiment, p1 is 3.

In one embodiment, q1 is defined in each (SiR ²¹ _p1 R ²² _q1 R ²³ _r1 ) Each unit is independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

In one embodiment, p1 is 0 and q1 is found in each (SiR ²¹ _p1 R ²² _q1 R ²³ _r1 ) Each unit is independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

In the above formula, R ^b1 Each occurrence is independently a hydroxyl group or a hydrolyzable group.

R is as described above ^b1 Preferably independently at each occurrence a hydrolyzable group.

R is as described above ^b1 Preferably independently at each occurrence-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO or halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), more preferably-OR ^h (i.e., alkoxy). As R ^h Examples of the method include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc.; substituted alkyl groups such as chloromethyl. Of these, alkyl groups are preferable, unsubstituted alkyl groups are particularly preferable, and methyl or ethyl groups are more preferable. In one embodiment R ^h Methyl, in another mode R ^h Is ethyl.

In the above formula, R ^c1 Each occurrence is independently a 1-valent organic group. The 1-valent organic group is a group other than the above-mentioned hydrolyzable group A 1-valent organic group other than a group.

The above R ^c1 In which the 1-valent organic group is preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl groups are more preferably methyl groups.

Each occurrence of k1 is an integer of 0 to 3, each occurrence of l1 is an integer of 0 to 3, each occurrence of m1 is an integer of 0 to 3. Wherein the sum of k1, l1 and m1 is within (SiR ^a1 _k1 R ^b1 _l1 R ^c1 _m1 ) The number of the units is 3.

In one embodiment, k1 is defined in each (SiR ^a1 _k1 R ^b1 _l1 R ^c1 _m1 ) Each unit is independently an integer of 1 to 3, preferably 2 or 3, more preferably 3. In a preferred embodiment, k1 is 3.

In the formula (S2), at least 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded are present.

In a preferred embodiment, at least 2 Si atoms to which hydroxyl groups or hydrolyzable groups are bonded are present in the terminal portion of formula (S2).

In a preferred embodiment, the group of formula (S2) has the formula-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). Z is Z ¹ 、Z ^1′ 、Z ^1″ 、R ²² 、R ²³ 、R ^22′ 、R ^23′ 、R ^22″ And R is ^23″ Is as defined above.

In a preferred embodiment, R is present in formula (S2) ^21′ In the case of (a), at least 1, preferably all, R ^21′ Wherein q1' is an integer of 1 to 3, preferably 2 or 3, more preferably 3.

In a preferred embodiment, R is present in formula (S2) ²¹ In the case of (a), at least 1, preferably all, R ²¹ Wherein p1 'is 0 and q1' is an integer of 1 to 3, preferably 2 or 3, more preferably 3.

In a preferred embodiment, R is present in formula (S2) ^a1 In the case of (a), at least 1, preferably all, R ^a1 Wherein p1 is 0, q1 is an integer of 1 to 3, preferably 2 or 3, more preferably 3.

In a preferred embodiment, in formula (S2), k1 is 2 or 3, preferably 3, p1 is 0, and q1 is 2 or 3, preferably 3.

R ^d1 Each occurrence is independently-Z ² －CR ³¹ _p2 R ³² _q2 R ³³ _r2 。

Z ² Each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ² Right side of the structure of (C) and (CR) ³¹ _p2 R ³² _q2 R ³³ _r2 ) And (5) combining.

In a preferred mode, Z ² Is a 2-valent organic group.

In a preferred mode, Z ² Does not contain siloxane bonds.

The above Z ² Preferably C _1－6 Alkylene, - (CH) ₂ ) _z5 －O－(CH ₂ ) _z6 - (wherein z5 is an integer of 0 to 6, for example an integer of 1 to 6, and z6 is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z7 -phenylene- (CH) ₂ ) _z8 - (wherein z7 is an integer of 0 to 6, for example, an integer of 1 to 6), and z8 is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ² Is C _1－6 Alkylene or- (CH) ₂ ) _z7 -phenylene- (CH) ₂ ) _z8 -, preferably-phenylene- (CH) ₂ ) _z8 －。Z ² When such a group is used, the light resistance, particularly ultraviolet resistance, can be further improved.

In another preferred embodiment, Z is as defined above ² Is C _1－3 An alkylene group. In one embodiment, Z ² Can be-CH ₂ CH ₂ CH ₂ -. In another mode, Z ² Can be-CH ₂ CH ₂ －。

R ³¹ Each occurrence is independently-Z ^2′ －CR ^32′ _q2′ R ^33′ _r2′ 。

Z ^2′ Each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ^2′ Right side of the structure of (C) and (CR) ^32′ _q2′ R ^33′ _r2′ ) And (5) combining.

In a preferred mode, Z ^2′ Does not contain siloxane bonds.

The above Z ^2′ Preferably C _1－6 Alkylene, - (CH) ₂ ) _z5′ －O－(CH ₂ ) _z6′ - (wherein z5 'is an integer of 0 to 6, for example an integer of 1 to 6, and z6' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z7′ -phenylene- (CH) ₂ ) _z8′ - (wherein z7 'is an integer of 0 to 6, for example, an integer of 1 to 6), and z8' is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ^2′ Is C _1－6 Alkylene or- (CH) ₂ ) _z7′ -phenylene- (CH) ₂ ) _z8′ -, preferably-phenylene- (CH) ₂ ) _z8′ －。Z ^2′ When such a group is used, the light resistance, particularly ultraviolet resistance, can be further improved.

In another preferred embodiment, Z is as defined above ^2′ Is C _1－3 An alkylene group. In one embodiment, Z ^2′ Can be-CH ₂ CH ₂ CH ₂ -. In another mode, Z ^2′ Can be-CH ₂ CH ₂ －。

R is as described above ^32′ Each occurrence is independently-Z ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 。

The above Z ³ Each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ³ Right side of the structure of (1) and (SiR) ³⁴ _n2 R ³⁵ _3－n2 ) And (5) combining.

In one embodiment, Z ³ Is an oxygen atom.

In one embodiment, Z ³ Is a 2-valent organic group.

In a preferred mode, Z ³ Does not contain siloxane bonds.

The above Z ³ Preferably C _1－6 Alkylene, - (CH) ₂ ) _z5″ －O－(CH ₂ ) _z6″ - (wherein z5 'is an integer of 0 to 6, for example an integer of 1 to 6, and z 6' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z7″ -phenylene- (CH) ₂ ) _z8″ - (wherein z7 "is an integer of 0 to 6, for example, an integer of 1 to 6), and z 8" is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ³ Is C _1－6 Alkylene or- (CH) ₂ ) _z7″ -phenylene- (CH) ₂ ) _z8″ -, preferably-phenylene- (CH) ₂ ) _z8″ －。Z ³ When such a group is used, the light resistance, particularly ultraviolet resistance, can be further improved.

In another preferred embodiment, Z is as defined above ³ Is C _1－3 An alkylene group. In one embodiment, Z ³ Can be-CH ₂ CH ₂ CH ₂ -. In another mode, Z ³ Can be-CH ₂ CH ₂ －。

R is as described above ³⁴ Each occurrence is independently a hydroxyl group or a hydrolyzable group.

R ³⁴ Preferably independently at each occurrence a hydrolyzable group.

R ³⁴ Preferably independently at each occurrence-OR ^h 、－OCOR ^h 、－O－N＝CR ^h ₂ 、－NR ^h ₂ 、－NHR ^h -NCO or halogen (in these formulae, R ^h Represents substituted or unsubstituted C _1－4 Alkyl), more preferably-OR ^h (i.e., alkoxy). As R ^h Examples of the method include: unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc.; substituted alkyl groups such as chloromethyl. Of these, alkyl groups are preferable, unsubstituted alkyl groups are particularly preferable, and methyl or ethyl groups are more preferable. In one embodiment R ^h Methyl, in another mode R ^h Is ethyl.

R is as described above ³⁵ Each occurrence is independently a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

The above R ³⁵ In which the 1-valent organic group is preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl groups are more preferably methyl groups.

In the above formula, n2 is represented by the formula (SiR ³⁴ _n2 R ³⁵ _3－n2 ) Each unit is independently an integer of 0 to 3. Wherein at least 2 terminal portions of formula (S3) are presentn2 is 1 to 3 (SiR ³⁴ _n2 R ³⁵ _3－n2 ) A unit. In other words, at least 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded are present in the terminal portion of the formula (S3).

n2 is found in each (SiR ³⁴ _n2 R ³⁵ _3－n2 ) Each unit is independently an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3.

R is as described above ^33′ Each occurrence of which is independently a hydrogen atom, a hydroxyl group, or a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

The above R ^33′ In which the 1-valent organic group is preferably C _1－20 Alkyl or- (C) _s H _2s ) _t1 －(O－C _s H _2s ) _t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl is particularly preferably methyl.

In one embodiment, R ^33′ Is hydroxyl.

In another mode, R ^33′ Is a 1-valent organic group, preferably C _1－20 Alkyl, more preferably C _1－6 An alkyl group.

Each occurrence of q2 'is independently an integer of 0 to 3, and each occurrence of r2' is independently an integer of 0 to 3. Wherein the sum of q2 'and r2' is within (CR ^32′ _q2′ R ^33′ _r2′ ) The number of the units is 3.

q2' is shown at each (CR ^32′ _q2′ R ^33′ _r2′ ) Each unit is independently an integer of preferably 1 to 3, more preferably 2 to 3, and even more preferably 3.

R ³² Each occurrence is independently-Z ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 . The Z is ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 The meaning of R is as defined above for R ^32′ The description is the same.

R is as described above ³³ Each occurrence of which is independently a hydrogen atom, a hydroxyl group, or a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

The above R ³³ In which the 1-valent organic group is preferably C _1－20 Alkyl or- (C) _s H _2s ) _t1 －(O－C _s H _2s ) _t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl is particularly preferably methyl.

In one embodiment, R ³³ Is hydroxyl.

In another mode, R ³³ Is a 1-valent organic group, preferably C _1－20 Alkyl, more preferably C _1－6 An alkyl group.

P2 is an integer of 0 to 3 independently for each occurrence, q2 is an integer of 0 to 3 independently for each occurrence, and r2 is an integer of 0 to 3 independently for each occurrence. Wherein the sum of p2, q2 and r2 is in (CR ³¹ _p2 R ³² _q2 R ³³ _r2 ) The number of the units is 3.

In one embodiment, p2 is 0.

In one embodiment, p2 is present at each (CR ³¹ _p2 R ³² _q2 R ³³ _r2 ) The units are each independently an integer of 1 to 3, an integer of 2 to 3, or 3. In a preferred embodiment, p2 is 3.

In one embodiment, q2 is found in each (CR ³¹ _p2 R ³² _q2 R ³³ _r2 ) Each unit is independently an integer of 1 to 3, preferably an integer of 2 to 3, more preferably 3.

In one embodiment, p2 is 0 and q2 is present in each (CR ³¹ _p2 R ³² _q2 R ³³ _r2 ) Each unit is independently an integer of 1 to 3, preferably an integer of 2 to 3, and more preferably 3.

R is as described above ^e1 Each occurrence is independently-Z ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 . The Z is ³ －SiR ³⁴ _n2 R ³⁵ _3－n2 The meaning of R is as defined above for R ^32′ The description is the same.

R is as described above ^f1 Each occurrence of which is independently a hydrogen atom, a hydroxyl group, or a 1-valent organic group. The 1-valent organic group is a 1-valent organic group other than the above-described hydrolyzable group.

The above R ^f1 In which the 1-valent organic group is preferably C _1－20 Alkyl or- (C) _s H _2s ) _t1 －(O－C _s H _2s ) _t2 (wherein s is an integer of 1 to 6, preferably an integer of 2 to 4, t1 is 1 or 0, preferably 0, t2 is an integer of 1 to 20, preferably an integer of 2 to 10, more preferably an integer of 2 to 6), more preferably C _1－20 Alkyl, more preferably C _1－6 Alkyl is particularly preferably methyl.

In one embodiment, R ^f1 Is hydroxyl.

In another mode, R ^f1 Is a 1-valent organic group, preferably C _1－20 Alkyl, more preferably C _1－6 An alkyl group.

Each occurrence of k2 is an integer of 0 to 3, each occurrence of l2 is an integer of 0 to 3, each occurrence of m2 is an integer of 0 to 3. Wherein the sum of k2, l2 and m2 is in (CR ^d1 _k2 R ^e1 _l2 R ^f1 _m2 ) The number of the units is 3.

In one embodiment, n2 is 1 to 3, preferably 2 or 3, more preferably 3 (SiR ³⁴ _n2 R ³⁵ _3－n2 ) The units are present in more than 2, for example from 2 to 27, preferably from 2 to 9, more preferably from 2 to 6, even more preferably from 2 to 3, particularly preferably 3, terminal portions of the formula (S3).

In a preferred embodiment, R is present in formula (S3) ^32′ In the case of at least 1, preferably all R ^32′ In (2), n2 is an integer of 1 to 3, preferably 2 or 3, more preferably 3.

In a preferred embodiment, R is present in formula (S3) ³² In the case of at least 1, preferably all R ³² In (2), n2 is an integer of 1 to 3, preferably 2 or 3, more preferably 3.

In a preferred embodiment, R is present in formula (S3) ^e1 In the case of at least 1, preferably all R ^a1 In (2), n2 is an integer of 1 to 3, preferably 2 or 3, more preferably 3.

In a preferred embodiment, in formula (S3), k2 is 0, l2 is 2 or 3, preferably 3, and n2 is 2 or 3, preferably 3.

R is as described above ^g1 And R is ^h1 Each occurrence is 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 . Here, R is 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.

In a preferred mode, R ^g1 And R is ^h1 Each independently is-Z ⁴ －SiR ¹¹ _n1 R ¹² _3－n1 。

The above Z ⁴ Each occurrence of which is independently a single bond, an oxygen atom, or a 2-valent organic group. Wherein, hereinafter, Z is referred to as ⁴ Right side of the structure of (1) and (SiR) ¹¹ _n1 R ¹² _3－n1 ) And (5) combining.

In one embodiment, Z ⁴ Is an oxygen atom.

In one embodiment, Z ⁴ Is a 2-valent organic group.

In a preferred mode, Z ⁴ Does not contain siloxane bonds.

The above Z ⁴ Preferably C _1－6 Alkylene, - (CH) ₂ ) _z5″ －O－(CH ₂ ) _z6″ - (wherein z5 'is an integer of 0 to 6, for example an integer of 1 to 6, and z 6' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z7″ -phenylene- (CH) ₂ ) _z8″ - (wherein z7 "is an integer of 0 to 6, for example, an integer of 1 to 6), and z 8" is an integer of 0 to 6, for example, an integer of 1 to 6). The C is _1－6 The alkylene group may be linear or branched, and is preferably linear. These groups may be selected, for example, from fluorine atoms, C _1－6 Alkyl, C _2－6 Alkenyl and C _2－6 1 or more substituents in the alkynyl group are substituted, but preferably unsubstituted.

In a preferred mode, Z ⁴ Is C _1－6 Alkylene or- (CH) ₂ ) _z7″ -phenylene- (CH) ₂ ) _z8″ -, preferably-phenylene- (CH) ₂ ) _z8″ －。Z ³ When these groups are used, the light resistance, particularly ultraviolet resistance, is further improved.

In another preferred embodiment, Z is as defined above ⁴ Is C _1－3 An alkylene group. In one embodiment, Z ⁴ Can be-CH ₂ CH ₂ CH ₂ -. In another mode, Z ⁴ Can be-CH ₂ CH ₂ －。

In a preferred embodiment, formulae (S1), (S2), (S3) and (S4) do not contain siloxane bonds.

In one embodiment, R ^H Is a group represented by the formula (S2), (S3) or (S4).

In one embodiment, R ^H Is a group represented by the formula (S2) or (S3).

In one embodiment, R ^H Is a group represented by the formula (S3) or (S4).

In one embodiment, R ^H Is a group represented by the formula (S1). In a preferred embodiment, the formula (S1) is a group represented by the formula (S1-b). In a preferred mode, R in the formula ¹³ Is hydrogenAtomic, X ¹¹ Is a single bond or-R ²⁸ －O _x －R ²⁹ - (wherein R is ²⁸ And R is ²⁹ Each occurrence is independently a single bond or C _1－20 Alkylene, x is 0 or 1), n1 is 1 to 3, preferably 2 to 3, more preferably 3.

In one embodiment, R ^H Is a group represented by the formula (S2). 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－(CH ₂ ) _z2 - (wherein z1 is an integer of 0 to 6, for example an integer of 1 to 6, and z2 is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z3 -phenylene- (CH) ₂ ) _z4 - (wherein z3 is an integer of 0 to 6, for example, an integer of 1 to 6, and z4 is an integer of 0 to 6, for example, an integer of 1 to 6), preferably C _1－6 Alkylene, q1 is 1 to 3, preferably 2 to 3, more preferably 3.

In one embodiment, R ^H Is a group represented by the formula (S3). 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 of 0 to 6, for example an integer of 1 to 6, and z 6' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z7″ -phenylene- (CH) ₂ ) _z8″ - (wherein z7 'is an integer of 0 to 6, for example an integer of 1 to 6, and z 8' is an integer of 0 to 6, for example an integer of 1 to 6), preferably C _1－6 Alkylene, n2 is 1 to 3, preferably 2 to 3, more preferably 3.

In one embodiment, R ^H Is a group represented by the formula (S4). In a preferred mode, R ^g1 And R is ^h1 is-Z ⁴ －SiR ¹¹ _n1 R ¹² _3－n1 ，Z ⁴ Is C _1－6 Alkylene, - (CH) ₂ ) _z5″ －O－(CH ₂ ) _z6″ - (wherein z5 'is an integer of 0 to 6, for example an integer of 1 to 6, and z 6' is an integer of 0 to 6, for example an integer of 1 to 6) or- (CH) ₂ ) _z7″ -phenylene- (CH) ₂ ) _z8″ - (wherein z7 'is an integer of 0 to 6, for example an integer of 1 to 6, and z 8' is an integer of 0 to 6, for example an integer of 1 to 6), preferably C _1－6 Alkylene, n1 is 1 to 3, preferably 2 to 3, more preferably 3.

X ^A Can be understood as a silicone part (R) ^S1 Or R is ^S2 ) And a site (R) providing binding energy to the substrate ^H ) And a connecting part for connecting. Thus, as long as the compounds represented by the formulas (1) and (2) can exist stably, the X ^A The compound may be a single bond or an arbitrary group.

In the above formula (1), α is an integer of 1 to 9, and β is an integer of 1 to 9. These alpha and beta can be determined according to X ^A And the valence of (c) varies. The sum of alpha and beta is equal to X ^A Valence of (2). For example at X ^A In the case of a 10-valent organic group, the sum of α and β is 10, and for example, α may be 9 and β may be 1, α may be 5 and β may be 5, or α may be 1 and β may be 9. In addition, at X ^A In the case of a 2-valent organic group, α and β are 1.

In the above formula (2), γ is an integer of 1 to 9. Gamma may be according to X ^A And the valence of (c) varies. That is, gamma is X ^A A value obtained by subtracting 1 from the valence of (2).

X ^A Each independently is a single bond or a 2 to 10 valent organic group.

Above X ^A The 2-10 valent organic group in (2) is preferably a 2-8 valent organic group. In one embodiment, the 2-10 valent organic group is preferably a 2-4 valent organic group, more preferably a 2 valent organic group. In another embodiment, the 2-10 valent organic group is preferably a 3-8 valent organic group, and more preferably a 3-6 valent organic group.

In one embodiment, X ^A Is a single bond or a 2-valent organic group, and alpha, beta and gamma are 1.

In one embodiment, X ^A 3-6 valence organic groups, alpha is 1, beta is 2-5, and gamma is 2-5.

In one embodiment, X ^A Is a 3-valent organic group, alpha is 1, and beta is 2.

At X ^A In the case of a single bond or a 2-valent organic group, the formulas (1) and (2) are represented by the following formulas (1 ') and (2').

R ^S1 -X ^A -R ^H (1’)

R ^H -X ^A -R ^S2 -X ^A -R ^H (2’)

In one embodiment, X ^A Is a single bond.

In another mode, X ^A Is a 2-valent organic group.

In one embodiment, X is ^A For example, a single bond or the following formula may be cited: - (R) ⁵¹ ) _p5 －(X ⁵¹ ) _q5 -the shown 2-valent organic group.

[ in the above-mentioned, a method for producing a semiconductor device,

R ⁵¹ is a single bond, - (CH) ₂ ) _s5 -or ortho-, meta-or para-phenylene, preferably- (CH) ₂ ) _s5 －，

s5 is an integer of 1 to 20, preferably an integer of 1 to 15, more preferably an integer of 1 to 10, still more preferably an integer of 1 to 6, for example an integer of 1 to 3, or an integer of 1 to 20, preferably an integer of 4 to 15, more preferably an integer of 7 to 13,

X ⁵¹ is- (X) ⁵² ) _l5 －，

X ⁵² Each occurrence is independently selected from the group consisting of-O-, -S-, O-phenylene m-phenylene or p-phenylene, -CO-, -C (O) O-, -CONR ⁵⁴ －、－O－CONR ⁵⁴ －、－NR ⁵⁴ -and- (CH) ₂ ) _n5 A group which is a radical of the formula,

R ⁵⁴ each occurrence of which is independently a hydrogen atom orA 1-valent organic group, preferably a hydrogen atom, phenyl group, C _1－6 Alkyl (preferably methyl) or a group containing an oxyalkylene group having 1 to 10 carbon atoms,

n5 is independently an integer of 1 to 20, preferably an integer of 1 to 15, more preferably an integer of 1 to 10, still more preferably an integer of 1 to 6, for example an integer of 1 to 3,

l5 is an integer of 1 to 10, preferably an integer of 1 to 5, more preferably an integer of 1 to 3,

p5 is either 0 or 1 and,

q5 is either 0 or 1 and,

Here, X is ^A (typically X) ^A Hydrogen atom of (C) may be selected from fluorine atoms, C _1－3 Alkyl and C _1－3 1 or more substituents in the fluoroalkyl group. In a preferred mode, X ^A Are not substituted with these groups. Wherein X is ^A Left side of (C) and R ^S1 Or R is ^S2 And (5) combining.

The above-mentioned group containing an oxyalkylene group having 1 to 10 carbon atoms is a group containing-O-C _1－10 The radical of an alkylene radical, e.g. -R ⁵⁵ －(－O－C _1－10 An alkylene group _n －R ⁵⁶ (wherein R is ⁵⁵ Is a single bond or a divalent organic group, preferably C _1－6 Alkylene, n is an arbitrary integer, preferably an integer from 2 to 10, R ⁵⁶ Is a hydrogen atom or a 1-valent organic group, preferably C _1－6 Alkyl). The alkylene group may be linear or branched.

In a preferred embodiment, X is as defined above ^A Each independently is- (R) ⁵¹ ) _p5 －(X ⁵¹ ) _q5 －R ⁵² －。R ⁵² Is a single bond, - (CH) ₂ ) _t5 -or ortho-, meta-or para-phenylene, preferably- (CH) ₂ ) _t5 -. t5 is an integer of 1 to 20, preferably an integer of 2 to 6, more preferably an integer of 2 to 3. Here, R is ⁵² (typically R) ⁵² Hydrogen atom of (C) may be selected from fluorine atoms, C _1－3 Alkyl and C _1－3 1 or more substituents in the fluoroalkyl group. In a preferred mode, R ⁵⁶ Are not substituted with these groups.

Preferably X is as defined above ^A Can be respectively and independently:

a single bond,

C _1－20 Alkylene group,

－R ⁵¹ －X ⁵³ －R ⁵² -, or

[ formula, R ⁵¹ And R is ⁵² Is as defined above,

X ⁵³ The method comprises the following steps:

a single bond,

－O－、

－S－、

－CO－、

－C(O)O－、

－CONR ⁵⁴ －、

－O－CONR ⁵⁴ －、

－O－(CH ₂ ) _u5 －CONR ⁵⁴ －、

－O－(CH ₂ ) _u5 -CO-, or

－CONR ⁵⁴ －(CH ₂ ) _u5 －N(R ⁵⁴ )－。

(wherein R is ⁵⁴ Is as defined above,

u5 is an integer of 1 to 20, preferably an integer of 2 to 6, more preferably an integer of 2 to 3. ) ].

More preferably X as described above ^A Each independently is:

a single bond,

C _1－20 Alkylene group,

－(CH ₂ ) _s5 －X ⁵³ －、

－X ⁵³ －(CH ₂ ) _t5 -, or

－(CH ₂ ) _s5 －X ⁵³ －(CH ₂ ) _t5 －。

[ wherein X is ⁵³ S5 and t5 are as defined above.]

In a preferred embodiment, X is as defined above ^A Can be respectively and independently:

a single bond,

C _1－20 Alkylene group,

－(CH ₂ ) _s5 －X ⁵³ －、

－X ⁵³ －(CH ₂ ) _t5 -or

－(CH ₂ ) _s5 －X ⁵³ －(CH ₂ ) _t5 －。

[ in the above-mentioned, a method for producing a semiconductor device,

X ⁵³ is a single bond, -O-, -CO-, -CONR ⁵⁴ －、－O－CONR ⁵⁴ －、－O－(CH ₂ ) _u5 －CONR ⁵⁴ -, or-O- (CH) ₂ ) _u5 －CO－，

s5, t5 and u5 are as defined above. ]

－(CH ₂ ) _s5 －O－(CH ₂ ) _t5 －、

－(CH ₂ ) _s5 －CONR ⁵⁴ －(CH ₂ ) _t5 －、

－(CH ₂ ) _s5 －O－(CH ₂ ) _u5 -CO-, or

－(CH ₂ ) _s5 －O－(CH ₂ ) _u5 －CONR ⁵⁴ －(CH ₂ ) _t5 －。

[ in the above-mentioned, a method for producing a semiconductor device,

s5, t5 and u5 are as defined above. ]

Above X ^A Can be independently selected from fluorine atoms, C _1－3 Alkyl and C _1－3 Fluoroalkyl (preferably C) _1－3 Perfluoroalkyl) is substituted with 1 or more substituents. In one embodiment, X ^A Is unsubstituted.

Wherein X is as described above ^A Left side and R of the formulae (I) ^S1 Or R is ^S2 Combine, right side and R ^H And (5) combining.

In another mode, X ^A Can be 3-10 valence organic groups respectively and independently.

In yet another embodiment, X is ^A Examples of (a) include groups represented by the following formula.

[ wherein X is ^a Is a single bond or a 2-valent organic group.]

Above X ^a Is a single bond or a divalent linking group directly bonded to the isocyanurate ring. As X ^a Preferably a single bond, an alkylene group, or a divalent group containing at least 1 bond selected from the group consisting of 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 containing at least 1 bond selected from the group consisting of an ether bond, an ester bond, an amide bond, and a thioether bond.

As X ^a More preferred is the following formula: - (CX) ¹²¹ X ¹²² ) _x1 －(X ^a1 ) _y1 －(CX ¹²³ X ¹²⁴ ) _z1 -the group shown.

(wherein X is ¹²¹ ～X ¹²⁴ H, OH OR-OSi (OR) ¹²¹ ) ₃ (wherein 3R' s ¹²¹ Independently alkyl groups having 1 to 4 carbon atoms),

above X ^a1 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 (left side of each bond with CX ¹²¹ X ¹²² Binding),

R ¹²² is C _1－6 Hydrocarbon chain of (C) is preferred _1－6 An alkyl group, a hydroxyl group,

x1 is an integer of 0 to 10, y1 is 0 or 1, and z1 is an integer of 1 to 10. )

As the above X ^a1 preferably-O-or-C (=O) O-.

As the above X ^a The following formula is particularly preferred: - (CH) ₂ ) _m12 －O－(CH ₂ ) _m13 - (wherein m12 is an integer of 1 to 10, and m13 is an integer of 1 to 10), and- (CH) ₂ ) _m15 －O－CH ₂ CH(OH)－(CH ₂ ) _m16 - (wherein m15 is an integer of 1 to 10, and m16 is an integer of 1 to 10), and- (CH) ₂ ) _m18 - (in which m18 is an integer of 1 to 10) or- (CH) ₂ ) _m20 －O－CH ₂ CH(OSi(OCH ₃ ) ₃ )－(CH ₂ ) _m21 - (wherein m20 is an integer of 1 to 10, and m21 is an integer of 1 to 10).

As the above X ^a The method is not particularly limited, and may be-CH ₂ －、－C ₂ H ₄ －、－C ₃ H ₆ －、－C ₄ H ₈ －、－C ₄ H ₈ －O－CH ₂ －、－CO－O－CH ₂ －CH(OH)－CH ₂ －、－S－、－NR ¹²¹ －、－(CH ₂ ) _m22 －C(＝O)－O－(CH ₂ ) _m23 －、－(CH ₂ ) _m22 －O－C(＝O)－(CH ₂ ) _m23 －、－(CH ₂ ) _m22 －C(＝O)－NR ¹²¹ －(CH ₂ ) _m23 －、－(CH ₂ ) _m22 －NR ¹²¹ －C(＝O)－(CH ₂ ) _m23 －CH ₂ OCH ₂ CH(OSi(OCH ₃ ) ₃ )CH ₂ - (wherein R) ¹²¹ Is C _1－6 Hydrocarbon chain, m22 is an integer of 1 to 10, and m23 is an integer of 1 to 10), and the like.

Above X ^a Is bonded to the isocyanurate ring.

In one embodiment, the siloxane-containing silane compound of the present invention is a siloxane-containing silane compound represented by formula (1).

In one embodiment, the siloxane-containing silane compound of the present invention is a siloxane-containing silane compound represented by formula (2).

The siloxane-containing silane compound represented by the above formula (1) or (2) may have a concentration of 5X 10 ² ～1×10 ⁵ The number average molecular weight of (2) is not particularly limited. The siloxane-containing silane compound represented by the above formula (1) or (2) preferably has a number average molecular weight of 1,000 to 30,000, more preferably 1,500 to 10,000, from the viewpoint of wear durability. Wherein the "number average molecular weight" is determined by ¹ H-NMR measured values.

The above-mentioned siloxane-based silane compound can be obtained, for example, by reacting a compound having an organosiloxane group with a compound having a hydrolyzable silane group.

For example, let the following formula: r is R ⁶¹ -COOH [ wherein R is ⁶¹ Is a group containing an organosiloxane group]The compounds shown are of the formula: NH (NH) ₂ －R ⁶² [ wherein R is ⁶² Is an allyl-containing group]The compounds shown react to give the following formula: r is R ⁶¹ －CONH－R ⁶³ －R ⁶⁴ _n [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶³ Is an (n+1) -valent linking group, R ⁶⁴ Is allyl group]. Next, the allyl compound obtained is reacted with HSiR ⁶⁵ _m R ⁶⁶ _3－m [ formula, R ⁶⁵ Each occurrence of which is independently a hydroxyl group or a hydrolyzable group, R ⁶⁶ Each occurrence is independently a 1-valent organic group, and m is 1 to 3]The compound shown in formula (1) can be obtained by reacting the compound shown in formula (1).

As a further method, R is used according to the following scheme ⁶¹ -COOH to give an oxadiazole compound,by using this as a starting material, a compound represented by formula (1) can be obtained. For example, in the case where R has an allyl group at the terminal, the reaction with HSiR is carried out as described above ⁶⁵ _m R ⁶⁶ _3－m The reaction can give a compound represented by the formula (1).

[ in the above-mentioned, a method for producing a semiconductor device,

R ⁶¹ is a group containing an organosiloxane group,

R is an alkyl or aryl group which may contain a functional group at the end,

the above functional group is a carboxylic acid derivative (e.g., allyl, ester, amide, carboxylic acid, acid anhydride, acid chloride, nitrile), amine, epoxide, benzene ring, alcohol, or unsaturated bond of an ester or the like. ]

As a further method, the following formula is used: r is R ⁶¹ －CW _m X _3－m [ formula, R ⁶¹ Is an organosiloxane-containing group, X is a hydrolyzable group, W is independently 1-valent organic group for each occurrence, and m is 1 to 3]The compounds shown are of the formula: M-R ⁶² [ wherein M is a metal-containing group, e.g., li, halogen-Mg, zn, R ⁶² Is an allyl-containing group]The compounds shown react to give the following formula: r is R ⁶¹ －CW _m (－R ⁶³ －R ⁶⁴ ) _3－m [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶³ Is a 2-valent group, R ⁶⁴ Is allyl, W is independently 1-valent organic group at each occurrence, and m is 1-3]. Next, the allyl compound obtained is reacted with HSiR ⁶⁵ _m R ⁶⁶ _3－m [ formula, R ⁶⁵ Each occurrence of which is independently a hydroxyl group or a hydrolyzable group, R ⁶⁶ Each occurrence is independently a 1-valent organic group, and m is 1 to 3]The compound shown in formula (1) can be obtained by reacting the compound shown in formula (1).

As a further method, the following formula is used: r is R ⁶¹ －COR ⁶⁷ [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶⁷ Is OH, or a halogen element, NR ₂ Hydrolyzable groups such as-OCOR 'and alkoxy, R is independently a hydrogen atom or an alkyl group, and R' is a hydrogen atom or an alkyl group]The compound and M-R ⁶² [ wherein M is a metal-containing group such as Li, halogen-Mg or Zn, R ⁶² Is an allyl-containing group]The compounds shown react to give the following formula: r is R ⁶¹ －C(OH)(－R ⁶³ －R ⁶⁴ ) ₂ [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶³ Is a 2-valent group, R ⁶⁴ Is allyl group]The compounds shown. The resulting compound was reacted with the following formula: L-R ⁶² [ wherein L is an elimination group, R ⁶² Is an allyl-containing group]The compounds shown react to give R ⁶¹ －C(－O－R ⁶³ －R ⁶⁴ )(－R ⁶³ －R ⁶⁴ ) ₂ [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶³ Is a 2-valent group, R ⁶⁴ Is allyl group]The compounds shown. Next, the allyl compound obtained is reacted with HSiR ⁶⁵ _m R ⁶⁶ _3－m [ formula, R ⁶⁵ Each occurrence of which is independently a hydroxyl group or a hydrolyzable group, R ⁶⁶ Each occurrence is independently a 1-valent organic group, and m is 1 to 3]The compound shown in formula (1) can be obtained by reacting the compound shown in formula (1).

As a further method, the following formula is used: r is R ⁶¹ －CH＝CH ₂ [ formula, R ⁶¹ Is a group containing an organosiloxane group ]The compounds shown are of the formula: H-SiX ₃ [ wherein X is a hydrolyzable group]The reaction gives the following formula: r is R ⁶¹ －CH ₂ CH ₂ SiX ₃ The compounds shown. Next, the resulting compound is reacted with M-R ⁶² [ wherein M is a metal-containing group, such as Li, halogen-Mg, or Zn, R ⁶² Is an allyl-containing group]The compounds shown react to give the following formula: r is R ⁶¹ －CH ₂ CH ₂ Si(－R ⁶³ －R ⁶⁴ ) ₃ [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶³ Is a 2-valent group, R ⁶⁴ Is allyl group]. Then allyl compound is obtained. Next, the allyl compound obtained is reacted with HSiR ⁶⁵ _m R ⁶⁶ _3－m [ formula, R ⁶⁵ Each occurrence of which is independently a hydroxyl group or a hydrolyzable group, R ⁶⁶ Each occurrence is independently a 1-valent organic group, and m is 1 to 3]The compound shown in formula (1) can be obtained by reacting the compound shown in formula (1).

In the above reaction, R ⁶¹ －CH＝CH ₂ The compound represented by the formula (1) of the present invention can be obtained by reacting the compound with an oxidizing agent to obtain an epoxy compound.

Further let R ⁶¹ －CH＝CH ₂ With thiol compounds shown by HSR to obtain R ⁶¹ －CH ₂ －CH ₂ -SR or R ⁶¹ －CH(SR)－CH ₃ The sulfur-containing compound shown in the formula (1) of the present invention can be obtained by using the sulfur-containing compound. Here, R is an arbitrary group.

Further according to the scheme below, R ⁶¹ －CH＝CH ₂ The compound represented by the formula (1) of the present invention can be obtained by reacting a diene with the compound to form a cyclic compound and using the cyclic compound.

[ wherein R is each independently a hydrocarbon, a hydrogen atom or an oxygen atom, a nitrogen atom, or-COR'. R' is any group. ]

Further according to the scheme below, R ⁶¹ －CH＝CH ₂ With diborane, borane dimethyl sulfide complex and 9-borabicyclo [3, 1 ]]The compound represented by the formula (1) of the present invention can be obtained by reacting a boron reagent such as nonane, and then converting the resulting borane derivative into an alcohol compound, and using the alcohol compound.

[ wherein R is each independently a hydrogen atom or a hydrocarbon group. ]

As a further method, the following formula is used: r is R ⁶¹ －SiW ² -H [ formula, R ⁶¹ W is independently 1-valent organic radical in each occurrence]The compounds shown are of the formula: h ₂ C＝CH－R ⁶⁷ [R ⁶⁷ Is a group containing functional groups such as amide, carboxylic acid, anhydride, acyl chloride, nitrile, amine, epoxide, benzene ring, alcohol and the like]The reaction can give the following formula: r is R ⁶¹ －SiX ₂ －CH ₂ CH ₂ －R ⁶⁷ The compounds shown. The compound represented by the formula (1) can be obtained by using the above reaction as a starting material.

As a further method, the following formula is used: r is R ⁶¹ －CH ₂ NR ⁶⁸ H [ formula, R ⁶¹ Is an organosiloxane group-containing group, R ⁶⁸ Is an arbitrary group]The compounds shown are of the formula: HOCO-R ⁶⁹ [ formula, R ⁶⁹ Is a double bond-containing group]The compounds shown react to give the following formula: r is R ⁶¹ －CH ₂ NR ⁶⁸ CO－R ⁶⁹ . The compound is used as a raw material for R ⁶⁹ The double bond contained therein undergoes the hydrosilylation reaction described above, whereby the compound represented by formula (1) can be obtained.

As an additional method. The following formula is used: r is R ⁶¹ －CH ₂ NH ₂ [ formula, R ⁶¹ Is a group containing an organosiloxane group]The compound and R are shown ⁷⁰ -COOH [ in the formula, R ⁷⁰ Is a group containing double bond, amide, carboxylic acid, anhydride, acyl chloride, nitrile, amine, epoxide, benzene ring, alcohol, etc. functional group]The compounds shown react to give R ⁶¹ －CH ₂ NHCO－R ⁷⁰ The compound represented by the formula (1) can be obtained by using the compound as a starting material.

As another method, a compound represented by the formula (1) can be obtained by using a compound obtained by reacting an epoxy compound with a compound represented by the following scheme as a raw material.

/>

[ in the above-mentioned, a method for producing a semiconductor device,

R ⁶¹ is a group containing an organosiloxane group,

R ¹ is a hydrogen atom or an alkyl group,

R ² is a hydrogen atom or an alkyl group,

r is a hydrocarbon group whose terminal may contain a functional group,

The above functional group is a carboxylic acid derivative (for example, ester, amide, carboxylic acid, acid anhydride, acid chloride, nitrile), amine, epoxide, benzene ring, alcohol, or unsaturated bond of ester or the like. ]

As a further method, R is caused according to the following scheme ⁶¹ －CH ₂ X is reacted with isocyanuric acid in the presence of an appropriate base (sodium hydride, sodium carbonate, potassium t-butoxide, hexamethyldisilazane metal salt, etc.), whereby a substituted isocyanurate compound can be obtained. Here, X is an erasable functional group, and examples thereof include chloride, bromide, iodide, p-toluenesulfonate, trifluoromethanesulfonate, and carboxylate.

The hydrosilylation described above is preferably carried out using a transition metal catalyst. The transition metal catalyst is preferably a group 8 to 10 transition metal catalyst, and among them, a platinum catalyst, a ruthenium catalyst, a rhodium catalyst, and the like are exemplified. Among them, a platinum catalyst is preferable. Examples of the platinum catalyst include Pt/divinyl tetramethyl disiloxane complex, pt/tetramethyl tetravinyl cyclotetrasiloxane complex, chloroplatinic acid, and platinum oxide. Among them, either one of Pt/divinyl tetramethyl disiloxane complex and Pt/tetramethyl tetravinyl cyclotetrasiloxane complex is preferable.

The amount of the transition metal catalyst used is preferably 0.1 to 1,000ppm, particularly preferably 1 to 100ppm, based on the mass ratio of the compound having a double bond to be reacted. By setting the amount to be used as described above, the reaction proceeds moderately, and coloration due to the catalyst can be suppressed.

In a preferred embodiment, the above-mentioned catalyst, in particular a platinum catalyst, is used in combination with a nitrogen-containing compound or a sulfur-containing compound. These compounds may be used in an amount of 1 kind or 2 or more kinds.

Examples of the nitrogen-containing compound include aliphatic amine compounds, triethylamine, aromatic amine compounds (aniline, pyridine, etc.), phosphoramides (hexamethylphosphoramide, etc.), amide compounds (N, N-diethylacetamide, N-diethylformamide, N-dimethylacetamide, N-methylformamide, N-dimethylformamide, etc.), urea compounds (tetramethylurea, etc.), cyclic amide compounds (N-methylpyrrolidone, etc.), and the like. Among the nitrogen-containing compounds, those having a high donor number, which will be described later, are also preferable, and aliphatic amine compounds, aromatic amine compounds, phosphoramides, and urea compounds are preferable. In addition, when the basicity of the nitrogen-containing compound is high, side reactions such as hydrolysis or condensation reaction of the hydrolyzable group are likely to occur, and therefore, a compound having low basicity or neutrality is preferable. From such a viewpoint, aromatic amine compounds, phosphoramides, and urea compounds are preferable.

Examples of the sulfur-containing compound include sulfoxide compounds (tetramethylene sulfoxide, dimethyl sulfoxide, and the like).

The above-mentioned compound is preferably 1 or more of an aromatic amine compound and a sulfoxide compound, and particularly preferably 1 or more of tetramethylene sulfoxide or dimethyl sulfoxide.

The number of donors of the above-mentioned nitrogen-containing compound and sulfur-containing compound is large. The number of donors is one of the parameters of the solvent and is an indicator of electron (pair) donating property. When a compound having a large number of donors is used in combination with the transition metal catalyst, the coordination of the compound and the transition metal in the transition metal catalyst can be controlled because the coordination of the compound having a double bond and the transition metal can be considered. As a result, a composition having a specific composition can be obtained.

Here, the donor number is the nitrogen-containing compound or the sulfur-containing compound and SbCl ₅ The amount of heat at the time of forming the 1:1 adduct, the number of donors of each compound, the method of calculating the number of donors, and the like are disclosed in, for example, the following references (1) and (2), and the like. (1) Pure (Pure)&Appl.Chem.，Vol.41，No.3，pp.291－326，1975。(2)Pure&Appl.Chem.，Vol.58，No.8，pp.1153－1161，1986。

The amount of the nitrogen-containing compound or the sulfur-containing compound to be used is preferably 0.001 to 1,000 parts by mass, particularly preferably 0.01 to 10 parts by mass, based on 100 parts by mass of the compound having a double bond. The mass ratio of the amount of the transition metal catalyst to the amount of the nitrogen-containing compound or the sulfur-containing compound (nitrogen-containing compound or sulfur-containing compound: transition metal catalyst) is preferably 10:1 to 10,000:1, and particularly preferably 20:1 to 1,000:1.

The present invention provides an intermediate of a compound represented by the above formula (1) or (2).

The present invention provides a compound represented by the following formula (1-a) or (2-a).

R ^S1 -X ^B (1-a)

X ^B -R ^S2 -X ^B (2-a)

[ in the above-mentioned, a method for producing a semiconductor device,

R ^S1 each occurrence is independently R ¹ －R ^S －R ² _q －；

R ^S2 is-O _p －R ^S －R ² _q －；

R ¹ is a hydrocarbon group;

R ² is-SiR ³ ₂ －；

R ³ Each independently at each occurrence is a hydrocarbyl group;

p is 0 or 1;

q is each independently 0 or 1;

X ^B each independently is- (CH) ₂ ) _s6 －X ⁵³ －X ⁵⁴ 、－X ⁵³ －(CH ₂ ) _t6 －X ⁵⁴ Or- (CH) ₂ ) _s6 －X ⁵³ －(CH ₂ ) _t6 －X ⁵⁴ . (wherein X is ⁵³ is-O-, -CO-, -CONR ⁷⁴ －、－O－CONR ⁷⁴ －、－O－(CH ₂ ) _u6 －CONR ⁷⁴ -or-O- (CH) ₂ ) _u6 -CO-, a single bond,

R ⁷⁵ is-CH=CH ₂ or-CH ₂ －CH＝CH ₂ ，

R ⁷⁶ Is an organic group having a valence of 1,

R ⁷⁴ each occurrence of which is independently a hydrogen atom, phenyl group, C _1－6 An alkyl group or a group containing an oxyalkylene group having 1 to 10 carbon atoms,

s6 is an integer of 1 to 20,

t6 is an integer of 1 to 20,

u6 is an integer of 1 to 20. ) ]

R in the formulae (1-a) and (2-a) ^S1 And R is ^S2 Meaning of (A) and R in the formulae (1) and (2) ^S1 And R is ^S2 The same applies.

X ⁵³ Is a single bond, -O-, -CO-, -CONR ⁷⁴ －、－O－CONR ⁷⁴ －、－O－(CH ₂ ) _u6 －CONR ⁷⁴ -or-O- (CH) ₂ ) _u6 -CO-, preferably-O-, -CO-, -CONR ⁷⁴ －、－O－CONR ⁷⁴ －、－O－(CH ₂ ) _u6 －CONR ⁷⁴ -or-O- (CH) ₂ ) _u6 -CO-, more preferably CONR ⁷⁴ －。

R ⁷⁴ Each occurrence of which is independently a hydrogen atom, phenyl group, C _1－6 Alkyl or a group containing an oxyalkylene group having 1 to 10 carbon atoms, preferably a hydrogen atom or C _1－6 An alkyl group or a group containing an oxyalkylene group having 1 to 10 carbon atoms.

The group containing an oxyalkylene group having 1 to 10 carbon atoms is a group containing-O-C _1－10 Alkylene-radicals, e.g. -R ⁵⁵ －(－O－C _1－10 An alkylene group _n －R ⁵⁶ (wherein R is ⁵⁵ Is a single bond or a 2-valent organic group, preferably C _1－6 Alkylene, n is an arbitrary integer, preferably an integer from 2 to 10, R ⁵⁶ Is a hydrogen atom or a 1-valent organic group, preferably C _1－6 Alkyl). The alkylene group may be linear or branched.

In one embodiment, R ⁷⁴ Is a hydrogen atom.

In another mode, R ⁷⁴ Is a group containing an oxyalkylene group having 1 to 10 carbon atoms.

X ⁵⁴ Is R ⁷⁵ 、－NR ⁷⁵ ₂ 、－SiR ⁷⁵ ₂ R ⁷⁶ 、－SiR ⁷⁵ ₃ 、－CR ⁷⁵ ₂ R ⁷⁵ 、－CR ⁷⁵ ₃ 、－SiCl ₂ R ⁷⁶ 、－SiCl ₃ Or (b)preferably-NR ⁷⁵ ₂ 、－SiR ⁷⁵ ₂ R ⁷⁶ 、－SiR ⁷⁵ ₃ 、－CR ⁷⁵ ₂ R ⁷⁵ 、－CR ⁷⁵ ₃ Or->

In one embodiment, X ⁵⁴ Is R ⁷⁵ 、－NR ⁷⁵ ₂ 、－SiR ⁷⁵ ₂ R ⁷⁶ 、－SiR ⁷⁵ ₃ 、－CR ⁷⁵ ₂ R ⁷⁵ or-CR ⁷⁵ ₃ preferably-SiR ⁷⁵ ₃ or-CR ⁷⁵ ₃ More preferably-SiR ⁷⁵ ₃ 。

In another mode, X ⁵⁴ Is that

R ⁷⁵ is-CH=CH ₂ or-CH ₂ －CH＝CH ₂ preferably-CH ₂ －CH＝CH ₂ 。

R ⁷⁶ Is a 1-valent organic group, preferably C _1－6 Alkylene groups and groups containing an oxyalkylene group having 1 to 10 carbon atoms. The meaning of the group containing an oxyalkylene group having 1 to 10 carbon atoms is as above.

In a preferred manner, -X ⁵³ －X ⁵⁴ is-CON (CH) ₂ CH＝CH ₂ ) ₂ 、－CONHCH ₂ C(CH ₂ CH＝CH ₂ ) ₃ 。

At X ⁵⁴ is-SiR ⁷⁵ ₂ R ⁷⁶ or-CR ⁷⁵ ₂ R ⁷⁵ In this case, the 2-valent linear organosiloxane group is preferably- (SiR) in which a is 2 or more, preferably 3 or more ³ ₂ －O) _a －。

The composition of the present invention will be described below.

The composition of the present invention contains at least 1 kind of the siloxane-containing silane compound represented by the formula (1) or (2).

In one embodiment, the composition of the present invention comprises a compound represented by the formula (1).

In another embodiment, the composition of the present invention comprises a compound represented by the formula (2).

In another embodiment, the composition of the present invention comprises a compound represented by the formula (1) and a compound represented by the formula (2).

In the composition of the present invention, the compound represented by the formula (2) is preferably 0.1 mol% or more and 35 mol% or less relative to the total of the compound represented by the formula (1) and the compound represented by the formula (2). The lower limit of the content of the compound represented by the formula (2) may be preferably 0.1 mol%, more preferably 0.2 mol%, further preferably 0.5 mol%, further more preferably 1 mol%, particularly preferably 2 mol%, and particularly preferably 5 mol%, with respect to the total of the compound represented by the formula (1) and the compound represented by the formula (2). The upper limit of the content of the compound represented by the formula (2) may be preferably 35 mol%, more preferably 30 mol%, still more preferably 20 mol%, still more preferably 15 mol% or 10 mol% with respect to the total of the compound represented by the formula (1) and the compound represented by the formula (2). The compound represented by the formula (2) is preferably 0.1 to 30 mol%, more preferably 0.1 to 20 mol%, still more preferably 0.2 to 10 mol%, still more preferably 0.5 to 10 mol%, particularly preferably 1 to 10 mol%, for example 2 to 10 mol%, or 5 to 10 mol%, based on the total of the compound represented by the formula (1) and the compound represented by the formula (2).

In one embodiment, the content of the compound represented by the formula (1) or (2) may be preferably 0.1 to 50.0% by mass, more preferably 1.0 to 30.0% by mass, still more preferably 5.0 to 25.0% by mass, and particularly preferably 10.0 to 20.0% by mass, relative to the total composition.

In another embodiment, the content of the compound represented by the formula (1) or (2) may be preferably 0.001 to 30% by mass, more preferably 0.01 to 10% by mass, still more preferably 0.05 to 5% by mass, and particularly preferably 0.05 to 2% by mass, relative to the total composition.

In one embodiment, the composition of the present invention contains at least 1 of a siloxane-containing silane compound and a compound composed of a condensate obtained by condensing at least a part of the siloxane-containing silane compound.

In one embodiment, the composition of the present invention may contain a compound selected from R ⁷¹ OR ⁷² 、R ⁷³ _n8 C ₆ H _6－n8 、R ⁷⁴ R ⁷⁵ R ⁷⁶ Si－(O－SiR ⁷⁷ R ⁷⁸ ) _m8 －R ⁷⁹ Sum (OSiR) ⁷⁷ R ⁷⁸ ) _m9 Solvents in the compounds shown.

[ in the above-mentioned, a method for producing a semiconductor device,

m8 is an integer of 1 to 6,

m9 is an integer of 3 to 8,

n8 is an integer of 0 to 6. ]

The monovalent organic group having 1 to 10 carbon atoms may be linear or branched, or may have a cyclic structure.

In one embodiment, the monovalent organic group having 1 to 10 carbon atoms may contain an oxygen atom, a nitrogen atom or a halogen atom.

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

In a preferred embodiment, the monovalent organic group having 1 to 10 carbon atoms is a hydrocarbon group which may be substituted with halogen, preferably a hydrocarbon group which is not substituted with halogen.

In one embodiment, the hydrocarbon group is a straight chain.

In another embodiment, the hydrocarbon group is branched.

In another embodiment, the hydrocarbon group includes a cyclic structure.

In one embodiment, the solvent is R ⁷¹ OR ⁷² 。

R ⁷¹ And R is ⁷² Can be each independently preferably a hydrocarbon group having 1 to 8 carbon atoms, more preferably C _1－6 Alkyl or C of (2) _5－8 Cycloalkyl groups of (a).

In one embodiment, the solvent is R ⁷³ _n8 C ₆ H _6－n8 。

C ₆ H _6－n8 Is an n 8-valent benzene ring. Namely, R ⁷³ _n8 C ₆ H _6－n8 To be n 8R ⁷³ Substituted benzenes.

R ⁷³ C which may be each independently halogen or may be substituted by halogen _1－6 Is a hydrocarbon group.

n8 is preferably an integer of 1 to 3.

In one embodiment, the solvent is R ⁷⁴ R ⁷⁵ R ⁷⁶ Si－(O－SiR ⁷⁷ R ⁷⁸ ) _m8 －R ⁷⁹ 。

In one embodiment, the solvent is (OSiR ⁷⁷ R ⁷⁸ ) _m9 。(OSiR ⁷⁷ R ⁷⁸ ) _m9 For a plurality of OSiRs ⁷⁷ R ⁷⁸ The units are bonded to form cyclic siloxanes.

R ⁷⁴ ～R ⁷⁹ Each independently is a hydrogen atom or C _1－6 Alkyl of (C) is preferred _1－6 More preferably C _1－3 More preferably methyl.

m8 is preferably an integer of 1 to 6, more preferably an integer of 1 to 5, and still more preferably 1 to 2.

m9 is preferably an integer of 3 to 6, more preferably an integer of 3 to 5.

In a preferred embodiment, the solvent may be hexamethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethyltetrasiloxane, octaethylcyclotetrasiloxane, decamethylpentasiloxane.

The composition of the present invention is preferably a surface treatment agent.

The surface treatment agent of the present invention may contain a solvent, a (non-reactive) organosilicon compound (hereinafter referred to as "silicone oil") which can be understood as silicone oil, an amine compound, alcohols, a catalyst, a surfactant, a polymerization inhibitor, a sensitizer, and the like.

Examples of the solvent include: aliphatic hydrocarbons such as hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; esters such as methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl 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, methylaminoketone, and 2-heptanone; glycol ethers such as ethyl 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, isopropanol, n-butanol, isobutanol, t-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, t-pentanol, and the like; glycols such as ethylene glycol and propylene glycol; cyclic ethers such as tetrahydrofuran, tetrahydropyran, and dioxane; amides such as N, N-dimethylformamide, N-dimethylacetamide, and N-methylpyrrolidone; ether alcohols such as methyl cellosolve, isopropyl cellosolve, butyl cellosolve, diethylene glycol monomethyl ether, and the like; diethylene glycol monoethyl ether acetate; ethers such as cyclopentyl methyl ether; hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane Silicones, etc.; 1, 2-trichloro-1, 2-trifluoroethane, 1, 2-dichloro-1, 2-tetrafluoroethane, dimethyl sulfoxide 1, 1-dichloro-1, 2, 3-pentafluoropropane (HCFC 225), ZEORORA H, 1, 3-bis (trifluoromethyl) benzene, HFE7100, HFE7200, HFE7300, CF ₃ CH ₂ OH、CF ₃ CF ₂ CH ₂ OH、(CF ₃ ) ₂ And fluorous solvents such as CHOH. Or a mixed solvent of 2 or more of them.

The fluorine-containing oil is not particularly limited, and examples thereof include compounds represented by the following general formula (3).

R ^1a －(SiR ^3a ₂ －O) _a1 －SiR ^3a ₂ －R ^1a ···(3)

[ in the above-mentioned, a method for producing a semiconductor device,

R ^1a each independently at each occurrence is a hydrogen atom or a hydrocarbyl group,

R ^3a each independently at each occurrence is a hydrogen atom or a hydrocarbyl group,

a1 is 2 to 3000.]

R is as described above ^3a Each occurrence of which is independently a hydrogen atom or a hydrocarbyl group. The hydrocarbyl group may be substituted.

R ^3a Each occurrence is independently preferably an unsubstituted hydrocarbon group or a hydrocarbon group substituted with a halogen atom. The halogen atom is preferably a fluorine atom.

R ^3a Each occurrence is independently preferably C which may be substituted by a halogen atom _1－6 Alkyl or aryl, more preferably C _1－6 Alkyl or aryl.

The aryl group is preferably phenyl.

In one embodiment, R ^3a Each occurrence is independently C _1－6 Alkyl, preferably C _1－3 Alkyl groups, more preferably methyl groups.

In another mode, R ^3a Is phenyl.

In another mode, R ^3a Methyl or phenyl, preferably methyl.

R is as described above ^1a Each occurrence of which is independently a hydrogen atom or a hydrocarbon group, and the meaning of which is as defined above for R ^3a The same applies.

R ^1a Each occurrence is independently preferably C which may be substituted by a halogen atom _1－6 Alkyl or aryl, more preferably C _1－6 Alkyl or aryl.

In one embodiment, R ^1a Each occurrence is independently C _1－6 Alkyl, preferably C _1－3 Alkyl groups, more preferably methyl groups.

In another mode, R ^1a Is phenyl.

In another mode, R ^1a Methyl or phenyl, preferably methyl.

The a1 is 2 to 1500. a1 is preferably 5 or more, more preferably 10 or more, still more preferably 15 or more, and may be, for example, 30 or more or 50 or more. a1 is preferably 1000 or less, more preferably 500 or less, still more preferably 200 or less, still more preferably 150 or less, and may be, for example, 100 or less or 80 or less.

a1 is preferably 5 to 1000, more preferably 10 to 500, still more preferably 15 to 200, still more preferably 15 to 150.

The silicone oil may have an average molecular weight of 500 to 100000, preferably 1000 to 10000. The molecular weight of the silicone oil can be determined using GPC.

As the silicone oil, for example, - (SiR) ^3a ₂ －O) _a1 -a 1 is a linear or cyclic silicone oil of 30 or less. The linear silicone oil may be so-called ordinary silicone oil or modified silicone oil. Examples of the general silicone oil include dimethyl silicone oil, methyl phenyl silicone oil, and methyl hydrogen silicone oil. Examples of the modified silicone oil include 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, and the like. Annular shapeExamples of the silicone oil include cyclic dimethylsiloxane oil and the like.

The silicone oil may be contained in an amount of, for example, 0 to 50% by mass, preferably 0.001 to 30% by mass, and more preferably 0.1 to 5% by mass, relative to the surface treatment agent of the present invention.

In the surface treating agent of the present invention, the silicone oil may contain, for example, 0 to 300 parts by mass, preferably 50 to 200 parts by mass, based on 100 parts by mass of the total of the silicone-containing silane compounds of the present invention (the sum of the silicone oils is 2 or more, the same applies hereinafter).

The silicone oil contributes to improving the surface slidability of the surface-treated layer.

Examples of the alcohols include alcohols having 1 to 6 carbon atoms which may be substituted with 1 or more fluorine atoms, such as methanol, ethanol, isopropanol, t-butanol, and CF ₃ 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, and the compatibility of the holosiloxane-containing silane compound with the solvent can be improved.

Examples of the catalyst include acids (e.g., acetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc.), bases (e.g., sodium hydroxide, potassium hydroxide, ammonia, triethylamine, diethylamine, etc.), transition metals (e.g., ti, ni, sn, zr, al, B, si, ta, nb, mo, W, cr, hf, V, etc.), sulfur-containing compounds having an unshared electron pair in the molecular structure, and nitrogen-containing compounds (e.g., sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphoramide compounds, amide compounds, and urea compounds).

Examples of the aliphatic amine compound include diethylamine and triethylamine. Examples of the aromatic amine compound include aniline and pyridine.

In a preferred embodiment, the transition metal is contained as a transition metal compound represented by M-R (wherein M is a transition metal atom and R is a hydrolyzable group). The transition metal compound is a compound in which a transition metal and a hydrolyzable group are bonded to each other, whereby the surface treatment layer can be more effectively made to contain a transition metal atom, and the friction durability and chemical resistance of the surface treatment layer can be further improved.

The hydrolyzable group is a group that can undergo a hydrolysis reaction, that is, a group that can be detached from a transition metal atom by a hydrolysis reaction, similarly to the hydrolyzable group of the siloxane-containing silane compound. Examples of the hydrolyzable group include-OR ^m 、－OCOR ^m 、－O－N＝CR ^m ₂ 、－NR ^m ₂ 、－NHR ^m -NCO, halogen (in these formulae, R ^m Represents substituted or unsubstituted C _1－4 Alkyl), and the like.

In a preferred embodiment, the hydrolyzable group is-OR ^m Preferably methoxy or ethoxy. By using an alkoxy group as a hydrolyzable group, the surface-treated layer can be more effectively made to contain a transition metal atom, and the friction durability and chemical resistance of the surface-treated layer can be further improved.

In one embodiment, the hydrolyzable group may be the same as that contained in the siloxane-containing silane compound. By making the hydrolyzable groups in the siloxane-containing silane compound and the transition metal compound the same groups, the influence thereof can be reduced even in the case where the hydrolyzable groups are exchanged with each other.

In another embodiment, the hydrolyzable group may be different from the hydrolyzable group contained in the siloxane-containing silane compound. The reactivity of hydrolysis can be controlled by making the hydrolyzable groups in the siloxane-containing silane compound and the transition metal compound different groups.

In one embodiment, the hydrolyzable group and the hydrolyzable group contained in the siloxane-containing silane compound may be exchanged with each other in the surface treating agent.

In a preferred embodiment, the transition metal compound is Ta (OR ^m ) ₅ Preferably Ta (OCH) ₂ CH ₃ ) ₅ 。

The catalyst may be contained in an amount of, for example, 0.0002 mass% or more relative to the entire surface treatment agent. The catalyst is preferably contained in an amount of 0.02 mass% or more, more preferably 0.04 mass% or more, based on the entire surface treatment agent. The catalyst may be contained in an amount of, for example, 10 mass% or less, particularly 1 mass% or less, relative to the entire surface treatment agent. The surface treatment agent of the present invention contains the catalyst at the above concentration, thereby contributing to the formation of a surface treatment layer having better durability.

The content of the catalyst is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, and particularly preferably 0 to 1% by mass, based on the siloxane-containing silane compound of the present invention.

The catalyst promotes hydrolysis and dehydration condensation of the siloxane-containing silane compound of the present invention, and promotes formation of a layer formed from the surface treating agent of the present invention.

Examples of the other component include tetraethoxysilane, methyltrimethoxysilane, 3-aminopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, and methyltriacetoxysilane, in addition to the above components.

The surface treatment agent of the present invention may contain, in addition to the above-mentioned components, a trace amount of, for example, pt, rh, ru, 1, 3-divinyl tetramethyl disiloxane, triphenylphosphine, naCl, KCl, condensates of silane, and the like as impurities.

The surface treatment agent of the present invention can provide a surface having a surface free energy of 18 to 35mN/m calculated from the contact angle between water and n-hexadecane when the substrate is treated.

The surface free energy is preferably 20mN/m or more, more preferably 22mN/m or more, still more preferably 24mN/m or more, preferably 33mN/m or less, more preferably 30mN/m or less, still more preferably 28mN/m or less, still more preferably 26mN/m or less.

The surface free energy was measured by a contact angle meter using water and n-hexadecane, contact angles (θ1 and θ2) of the substrate surface were measured, and then the values of the contact angles and the values of the surface free energy of water and n-hexadecane were substituted into the following equation, and the obtained simultaneous equations of 2 equations were solved to obtain γsd and γsp. Then, the sum of γsd and γsp is the surface free energy γs of the substrate surface.

{(1+cosθ)·γL}/2＝(γSd·γLd) ^1/2 +(γSp·γLp) ^1/2

[ in the above-mentioned, a method for producing a semiconductor device,

γl is the surface free energy of the liquid, γld and γlp are the dispersion term and the polar term, respectively, γl=γld+γlp. ]

Surface free energy γl=72.8 mN/m of water

The surface free energy dispersion term γld=21.8 mN/m of water

Polar term γlp=51.0 mN/m of the surface free energy of water

Surface free energy γl=27.6 mN/m of n-hexadecane

Surface free energy dispersion term γld=27.6 mN/m for n-hexadecane

Surface free energy polar term γlp=0 mN/m for n-hexadecane

In one embodiment, the surface treatment agent of the present invention is used in a dry coating method, preferably vacuum evaporation.

In one embodiment, the surface treatment agent of the present invention is used in a wet coverage method, preferably dip coating.

The surface treatment agent of the present invention can be impregnated into a porous material, for example, a porous ceramic material, a metal fiber, or a product obtained by fixing steel wool in a cotton-like state, and then formed into a pellet. The pellets can be used for vacuum evaporation, for example.

The object of the present invention will be described below.

The article of the present invention comprises a substrate, and a layer (surface-treated layer) formed of the surface-treating agent of the present invention on the surface of the substrate.

The substrate that can be used in the present invention may be composed of, for example, glass, resin (natural or synthetic resin, for example, may be a usual plastic material), metal, ceramic, semiconductor (silicon, germanium, etc.), fiber (fabric, nonwoven fabric, etc.), fur, leather, wood, ceramic, stone, etc., building elements, etc., sanitary articles, any appropriate material.

For exampleIn the case where the article to be manufactured is an optical member, the material constituting the surface of the base material may be a material for an optical member, such as glass or transparent plastic. In addition, in the case where the article to be manufactured is an optical member, some layers (or films) such as a hard coat layer or an antireflection layer or the like may be formed on the surface (outermost layer) of the substrate. The antireflection layer may use any of a single antireflection layer and a multilayer antireflection layer. Examples of the inorganic substance that can be used for 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 、HfO ₂ 、Si ₃ N ₄ 、CeO ₂ 、MgO、Y ₂ O ₃ 、SnO ₂ 、MgF ₂ 、WO ₃ Etc. These inorganic substances may be used alone or in combination of 2 or more of these (for example, in the form of a mixture). In the case of using a multilayer antireflection layer, it is preferable that SiO is used as the outermost layer thereof ₂ And/or SiO. In the case where the object to be manufactured is an optical glass member for a touch panel, a part of the surface of the base material (glass) may have a transparent electrode, and for example, a thin film of Indium Tin Oxide (ITO) or indium zinc oxide or the like is used. The substrate may have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomized film layer, a hard coat film layer, a polarizing film, a retardation film, a liquid crystal display module, and the like according to specific specifications thereof, and the like.

The shape of the substrate is not particularly limited, and may be, for example, a plate, a film, or other forms. The surface area of the substrate on which the surface treatment layer is to be formed may be at least a part of the surface of the substrate, and may be appropriately determined according to the purpose of the article to be manufactured, specific specifications, and the like.

In one embodiment, the substrate may be composed of a material having hydroxyl groups at least in a surface portion thereof. Examples of such a material include glass, and metals (particularly, base metals), ceramics, semiconductors, and the like, each of which has a natural oxide film or a thermal oxide film formed on the surface thereof. Alternatively, in the case where the hydroxyl group is insufficient although it is present, or in the case where the hydroxyl group is not present originally, as in the case of a resin or the like, the hydroxyl group may be introduced or increased on the surface of the substrate by performing some pretreatment on the substrate. Examples of the pretreatment include plasma treatment (for example, corona discharge) and ion beam irradiation. The plasma treatment is also suitable for introducing hydroxyl groups into the surface of a substrate, increasing hydroxyl groups, and cleaning the surface of the substrate (removing foreign matter, etc.). Further, as another example of the pretreatment, there may be mentioned: an interfacial adsorbent having a carbon-carbon unsaturated bond is formed on the surface of a substrate in the form of a monolayer by LB method (Langmuir-Blodgett method) or chemisorption method, and then the unsaturated bond is broken in an atmosphere containing oxygen, nitrogen, or the like.

In another embodiment, at least a surface portion of the substrate may be composed of a material containing an organosilicon compound having 1 or more other reactive groups, for example, si—h groups, or an alkoxysilane.

In a preferred embodiment, the substrate is glass. The glass is preferably a sapphire glass, a soda lime glass, an alkali aluminosilicate glass, a borosilicate glass, an alkali-free glass, a crystal glass, or a quartz glass, and particularly preferably a chemically strengthened soda lime glass, a chemically strengthened alkali aluminosilicate glass, or a chemically bonded borosilicate glass.

The article of the present invention can be produced by forming the layer of the surface treatment agent of the present invention on the surface of the base material, and if necessary, post-treating the layer.

The formation of the layer of the surface treatment agent of the present invention can be performed by applying the surface treatment agent to the surface of the substrate so as to cover the surface. The coating method is not particularly limited, and for example, a wet coating method and a dry coating method can be used.

Examples of the wet coating method include dip coating, spin coating, flow coating, spray coating, roll coating, gravure coating, wiping, knife coating, die coating, ink jet, casting, langmuir-Blodgett (Langmuir-Blodgett) method, and the like.

Examples of the dry coating method include vapor deposition (usually vacuum vapor deposition), sputtering, CVD, and the like. Specific examples of the vapor deposition method (typically, vacuum vapor deposition method) include resistance heating, electron beam, high-frequency heating using microwaves or the like, ion beam, and the like. Specific examples of the CVD method include plasma CVD, optical CVD, thermal CVD, and the like.

In addition, the coating may be performed by an atmospheric pressure plasma method.

When the wet coverage method is used, the surface treatment agent of the present invention can be applied to the surface of a substrate after dilution with a solvent. 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, mineral spirits; aromatic hydrocarbons such as benzene, toluene, xylene, naphthalene, and solvent naphtha; esters such as methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl 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, methylaminoketone, and 2-heptanone; glycol ethers such as ethyl 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, isopropanol, n-butanol, isobutanol, t-butanol, sec-butanol, 3-pentanol, octanol, 3-methyl-3-methoxybutanol, t-pentanol, and the like; glycols such as ethylene glycol and propylene glycol; cyclic ring of tetrahydrofuran, tetrahydropyran, dioxane, etc Ethers; amides such as N, N-dimethylformamide, N-dimethylacetamide, and N-methylpyrrolidone; ether alcohols such as methyl cellosolve, isopropyl cellosolve, butyl cellosolve, diethylene glycol monomethyl ether, and the like; 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 (for example, ASAHIKLIN (registered trademark) AC-6000 manufactured by asahi corporation), 1,2, 3, 4-heptafluorocyclopentane (for example, ZEORORA (registered trademark) H manufactured by japanese ray Weng Zhushi); hydrofluoroethers (HFEs) (e.g. perfluoropropyl methyl ether (C) ₃ F ₇ OCH ₃ ) (for example, novec (trademark) 7000 manufactured by Sumitomo 3M Co., ltd.), perfluorobutyl methyl ether (C) ₄ F ₉ OCH ₃ ) (for example, novec (trademark) 7100 manufactured by Sumitomo 3M Co., ltd.), perfluorobutyl ethyl ether (C) ₄ F ₉ OC ₂ H ₅ ) (for example, novec (trademark) 7200 manufactured by Sumitomo 3M Co., ltd.), perfluorohexyl methyl ether (C) ₂ F ₅ CF(OCH ₃ )C ₃ F ₇ ) Alkyl perfluoroalkyl ethers (perfluoroalkyl and alkyl groups may be linear or branched), such as Novec (trademark) 7300 produced by Sumitomo 3M Co., ltd., or CF ₃ CH ₂ OCF ₂ CHF ₂ Ether alcohols such as (for example, ASAHIKLIN (registered trademark) AE-3000 manufactured by Asahi Kabushiki Kaisha)), and cyclopentylmethyl ether; and siloxanes such as hexamethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethyltetrasiloxane, octaethylcyclotetrasiloxane, and decamethylcyclopentasiloxane. These solvents may be used alone or in the form of a mixture of 2 or more. Among them, preferred is a hydrofluoroether, and particularly preferred is a perfluorobutyl methyl ether (C ₄ F ₉ OCH ₃ ) And/or perfluorobutyl ethyl ether (C) ₄ F ₉ OC ₂ H ₅ ) Silicones, even more preferably hexamethyldisiloxane, octamethyltrisiloxane, hexamethylcyclotrisiloxane, octamethyltetrasiloxane or decamethylcyclopentasiloxane.

When the dry coating method is used, the surface treatment agent of the present invention may be used directly in the dry coating method or may be diluted with the above solvent and then used in the dry coating method.

The layer formation of the surface treatment agent is preferably carried out in such a manner that the surface treatment agent of the present invention and a catalyst for hydrolysis and dehydration condensation coexist in the layer. For simplicity, in the case of using the wet coating method, the catalyst may be added to the diluted solution of the surface treatment agent of the present invention after the surface treatment agent of the present invention is diluted with a solvent, that is, before the surface treatment agent is applied to the surface of a substrate. When the dry coating method is used, the surface treatment agent of the present invention to which a catalyst is added may be directly subjected to vapor deposition (usually vacuum vapor deposition), or may be subjected to vapor deposition (usually vacuum vapor deposition) using a particulate material in which a metal porous body such as iron or copper is impregnated with the surface treatment agent of the present invention to which a catalyst is added.

The catalyst may be any suitable acid or base, a transition metal (for example, ti, ni, sn, zr, al, B), a sulfur-containing compound having an unshared electron pair in the molecular structure, a nitrogen-containing compound (for example, a sulfoxide compound, an aliphatic amine compound, an aromatic amine compound, a phosphoramide compound, an amide compound, or a urea compound), or the like. 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, and the like can be used. Examples of the base catalyst include organic amines such as amine, sodium hydroxide, potassium hydroxide, triethylamine, and diethylamine. Examples of the transition metal, aliphatic amine compound and aromatic amine compound include the same ones as described above.

The surface treatment layer included in the article of the present invention has both high wear durability. The surface treatment layer has, in addition to high abrasion durability, water repellency, oil repellency, stain resistance (for example, to prevent adhesion of dirt such as fingerprints), water repellency (to prevent water from penetrating into electronic parts, etc.), surface slidability (or lubricity, wiping-off property of dirt such as fingerprints, and excellent touch feeling to fingers), chemical resistance, etc., depending on the composition of the surface treatment agent used, and can be suitably used as a functional film.

The invention therefore also relates to an optical material having an outermost layer with the surface treatment layer described above.

As the optical material, various optical materials are preferably exemplified in addition to the optical materials related to a display or the like which will be exemplified later, for example: a display such as a cathode ray tube (CRT, for example, a computer display), a liquid crystal display, a plasma display, an organic EL display, an inorganic thin film EL dot matrix display, a rear projection display, a fluorescent display tube (VFD), a field emission display (FED, field Emission Display), or a protective plate for these displays, or a material having an antireflection film treatment applied to the surface thereof.

The article of the present invention may be an optical member, but is not particularly limited. Examples of the optical member may be listed as follows: lenses such as glasses; front protection plates, antireflection plates, polarizing plates, antiglare plates for displays such as PDP, LCD, etc.; touch panels for devices such as mobile phones and portable information terminals; disc surfaces of optical discs such as Blu-ray discs, DVD discs, and CD-R, MO; an optical fiber; a display surface of a timepiece, and the like.

In addition, the article of the present invention may also be a medical device or a medical material. The article having the layer obtained by the present invention may be an automobile interior or exterior part. Examples of the exterior member include the following: vehicle window, lamp shade, car outside camera cover. Examples of the interior components include the following: instrument panel covers, navigation system touch screens, and decorative interior components.

The thickness of the above layer is not particularly limited. In the case of the optical member, the thickness of the layer is preferably in the range of 1 to 50nm, 1 to 30nm, preferably 1 to 15nm, from the viewpoints of optical performance, abrasion durability and stain resistance.

The compounds, compositions and articles of the present invention are described in detail above, but the compounds, compositions and articles of the present invention are not limited to the above examples.

Examples

Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to the following examples.

Synthesis example 1

R-COOH (10 g), 2-diallyl-4-penten-1-amine (1.71 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.98 g), triethylamine (1.44 mL), 4-dimethylaminopyridine (84 mg) and dichloromethane (30 mL) were mixed and stirred at room temperature overnight. Diluting the mixture with methylene chloride, washing with hydrochloric acid and water, concentrating under reduced pressure to obtain R-CONH-CH ₂ C(CH ₂ CH＝CH ₂ ) ₃ (8.88g)。

R is (CH) ₃ ) ₃ Si－(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₁₀ -. The average value of the number n of repeating units was 19.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.20-0.25(m),1.45-1.59(m,2H),1.20-1.48(m,14H),1.53-1.65(m,2H),2.03(d,2H,7.6Hz),2.16(t,2H,7.6Hz),3.20(d,2H,6.4Hz),5.05-5.14(m,6H),5.51-5.60(m,1H),5.80-5.93(m,3H)。

¹³ C NMR(CDCl ₃ ,133MHz)δ[ppm]：0.2,1.0,1.8,18.3,23.2,29.3,29.4,29.6,30.3,33.5,37.1,40.0,40.1,45.0,118.1,134.2,172.9。

Example 1

R-CONH-CH obtained in Synthesis example 1 ₂ C(CH ₂ CH＝CH ₂ ) ₃ (2g) Toluene (10 mL), a xylene solution of the Karstedt (Karstedt) catalyst (2%, 0.29 mL), aniline (46 mg), and trimethoxysilane (1.43 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CONH-CH ₂ C{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ (2.21g)。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.2-0.21(m),0.41-0.65(m,8H),1.10-1.50(m,26H),1.55-1.65(m,2H),2.14(t,2H,7.2Hz),3.09(d,2H,6.0Hz),3.45-3.62(m,27H),5.67-5.75(m,1H)。

¹³ C NMR(CDCl ₃ ,133MHz)δ[ppm]：0.1,1.0,1.7,9.5,16.1,18.2,23.2,26.0,29.4,29.4,29.6,30.2,33.4,37.0,38.1,39.1,43.6,50.4,173.0。

Synthesis example 2

R-COOH (10 g), diallylamine (2.01 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.98 g), 4-dimethylaminopyridine (84 mg) and dichloromethane (30 mL) were mixed and stirred overnight at room temperature. Diluted with methylene chloride, washed with hydrochloric acid and water, and concentrated under reduced pressure to give R-CON (CH) ₂ CH＝CH ₂ ) ₂ (9.00g)。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.25-0.30(m),1.45-1.59(m,2H),1.20-1.40(m,14H),1.55-1.68(m,2H),2.30(t,2H,7.2Hz),3.86(d,2H,5.2Hz),3.98(d,2H,6.0Hz),5.05-5.23(m,4H),5.68-5.84(m,2H)。

¹³ C NMR(CDCl ₃ ,133MHz)δ[ppm]：0.2,1.0,1.8,18.3,23.2,25.4,29.4,29.5,29.6,33.1,33.5,47.8,49.1,116.5,117.0,133.0,133.5,173.2。

Example 2

R-CON (CH) ₂ CH＝CH ₂ ) ₂ (2g) Toluene (10 mL), a xylene solution of a Kanster catalyst (2%, 0.20 mL), aniline (32 mg) and trimethoxysilane (1.00 mL) were mixed, stirred overnight at room temperature, and concentrated under reduced pressure to give R-CON { CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₂ (2.23g)。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.20-0.31(m),0.42-0.65(m,6H),1.10-1.40(m,14H),1.63-1.71(m,6H),2.26(t,2H,7.2Hz),3.19(t,2H,7.6Hz),3.27(t,2H,7.6Hz),3.45-3.65(m,18H)。

¹³ C NMR(CDCl ₃ ,133MHz)δ[ppm]：0.2,1.0,1.7,6.3,6.4,18.2,20.8,22.3,23.2,25.6,29.4,29.5,29.6,33.2,33.4,48.2,50.2,50.48,50.53,172.8。

Synthesis example 3

R- (COOH) ₂ (10 g, manufactured by Xinyue chemical Co., ltd., X-22-162C), 2-diallyl-4-pentene-1-amine (1.05 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.2 g), 4-dimethylaminopyridine (52 mg) and methylene chloride (33 mL) were mixed and stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with hydrochloric acid and water, and concentrated under reduced pressure to give R- (CONH-CH) ₂ C(CH ₂ CH＝CH ₂ ) ₃ ) ₂ (7.3 g). Wherein R is-CH ₂ CH ₂ －(OSi(CH ₃ ) ₂ ) _n －CH ₂ CH ₂ -, the average value of the number n of repeating units was 31.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.20-0.30(m),0.81-0.85(m,4H),2.03(d,12H),2.17-2.22(m,4H),3.19(d,4H),5.07-5.15(m,12H),5.63(2H,brt),5.83-5.90(m,6H)。

Example 3

R- (CONH-CH) obtained in Synthesis example 3 ₂ C(CH ₂ CH＝CH ₂ ) ₃ ) ₂ (2g) Toluene (9.5 mL), a xylene solution of the Kadset catalyst (2%, 0.19 mL), aniline (0.03 mL), and trimethoxysilane (0.92 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CONH-CH ₂ C{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ (2g) A. The invention relates to a method for producing a fibre-reinforced plastic composite Wherein R is-CH ₂ CH ₂ －(OSi(CH ₃ ) ₂ ) _n －CH ₂ CH ₂ -, the average value of the number n of repeating units was 31.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.20-0.30(m),0.57-0.70(m,12H),0.81-0.87(m,4H),1.17-1.37(m,12H),1.27-139(m,12H),2.13-2.23(m,4H),3.09(d,4H),3.54-3.65(m,54H),5.88(2H,brt)。

Synthesis example 4

R-CH ₂ OH (201 g, xinyue chemical Co., ltd., X-22-170 DX), acetone (400 mL), and saturated aqueous sodium bicarbonate (100 mL) were mixed and cooled to 0℃with ice water. To the mixture was added potassium bromide (1.02 g) and TEMPO (0.210 g) with stirring at 0 ℃. After stirring for 10 minutes, trichloroisocyanuric acid (19.9 g) was added. Gradually warm to room temperature and stir overnight. Isopropyl alcohol (200 mL) was added to the mixture, and the volatile components were concentrated under reduced pressure. To the concentrated solution was added water (300 mL), extracted with methylene chloride, and after drying, the solvent was distilled off under reduced pressure, whereby R-COOH (180 g) was obtained.

R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ －(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -. The average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.11-0.27(m),0.52-0.58(m,4H),0.89(t,J＝7.1Hz,3H),1.28-1.33(m,4H),1.66-1.70(m,2H),3.54(t,J＝6.9Hz,2H),4.11(s,2H)。

Synthesis example 5

R-COOH (10 g), 2-diallyl-4-penten-1-amine (1.71 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.98 g), 4-dimethylaminopyridine (84 mg) and methylene chloride (30 mL) obtained in synthesis example 4 were mixed and stirred at room temperature overnight. Diluting the mixture with methylene chloride, washing with hydrochloric acid and water, concentrating under reduced pressure to obtain R-CONH-CH ₂ C(CH ₂ CH＝CH ₂ ) ₃ (8.88 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ －(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.10-0.30(m),0.52-0.59(m,4H),0.88(t,J＝6.9Hz,3H),1.26-1.33(m,4H),1.61-1.69(m,2H),2.05(d,J＝7.3Hz,6H),3.22(d,J＝6.4Hz,2H),3.47(t,J＝6.6Hz,2H),3.93(s,2H),5.08-5.13(m,6H),5.82-5.92(m,3H),6.75(brs,1H)。

Example 4

R-CONH-CH obtained in Synthesis example 5 ₂ C(CH ₂ CH＝CH ₂ ) ₃ (5g) Toluene (5 mL), a xylene solution of the Kadset catalyst (2%, 0.24 mL), aniline (38 mg), and trimethoxysilane (1.19 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CONH-CH ₂ C{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ (4.8 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.13-0.32(m),0.54-0.63(m,10H),0.90(t,J＝7.1Hz,3H),1.23-1.37(m,16H),1.62-1.69(m,2H),3.17(d,J＝5.9Hz,2H),3.47-3.50(m,2H),3.56-3.63(m,27H),3.94(s,2H),6.54(brs,1H)。

Example 5

R-CONH-CH obtained in Synthesis example 5 ₂ C(CH ₂ CH＝CH ₂ ) ₃ (1g) Toluene (5 mL), xylene solution of Kadster catalyst (2%, 94. Mu.L), (CH) ₃ COO) ₃ SiCH ₃ (3.6 mg) and trichlorosilane (0.25 mL) were mixed. After stirring the mixture at 60℃for 4 hours, it was concentrated under reduced pressure to give R-CONH-CH ₂ C{CH ₂ CH ₂ CH ₂ SiCl ₃ } ₃ (0.9 g). R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.14-0.33(m),0.57-0.64(m,4H),0.96(t,J＝6.9Hz,3H),1.24-1.42(m,16H),1.48-1.58(m,6H),1.68-1.72(m,2H),3.22(d,J＝6.4Hz,2H),3.50(t,J＝7.1Hz,2H),4.05(s,2H),6.68(brs,1H)。

Synthesis example 6

Let R-ch=ch ₂ (5 g, gelest, MCR-V21), toluene (5 g), trichlorosilane (0.31 g), and a xylene solution of the Kadster catalyst (2%, 32. Mu.L) were mixed and stirred at 60℃for 4 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, and then dissolved in tetrahydrofuran (5 g), and allyl magnesium chloride (1.0 mol/L, 4.4 mL) was added under ice-cooling. After gradually warming to room temperature and stirring for 17 hours, a saturated aqueous sodium chloride solution was added. The insoluble material was filtered through a celite pad, and the filtrate was extracted with dichloromethane. Removing solvent by reduced pressure distillation to obtain R-CH ₂ CH ₂ Si(CH ₂ CH＝CH ₂ ) ₃ (4.7 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.07(s),0.42-0.62(4H,m),0.89(3H,t),1.26-1.35(4H,m),1.60(6H,d),4.84-5.17(6H,m),5.80(3H,tdd)。

Example 6

R-CH obtained in Synthesis example 6 ₂ CH ₂ Si(CH ₂ CH＝CH ₂ ) ₃ (2.5 g), toluene (2.5 mL), a xylene solution of the Kadset catalyst (2%, 0.10 mL), aniline (16 mg), and trimethoxysilane (0.52 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CH ₂ CH ₂ Si(CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ ) ₃ (2.5 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.08(s),0.41-0.74(12H,m),0.89(3H,t),1.23-1.33(4H,m),1.42-1.63(6H,m),3.57(27H,s)。

Synthesis example 7

Let R-ch=ch ₂ (5 g, gelest, MCR-V25), toluene (5 g), trichlorosilane (0.27 g), and a xylene solution of the Kadster catalyst (2%, 76. Mu.L) were mixed and stirred at 60℃for 4 hours. After leaving to cool to room temperature, the solvent was distilled off under reduced pressure, and then dissolved in tetrahydrofuran (5 g), and allyl magnesium chloride (1.0 mol/L, 2.2 mL) was added under ice-cooling. After gradually warming to room temperature and stirring for 17 hours, a saturated aqueous sodium chloride solution was added. The insoluble material was filtered through a celite pad, and the filtrate was extracted with dichloromethane. Removing solvent by reduced pressure distillation to obtain R-CH ₂ CH ₂ Si(CH ₂ CH＝CH ₂ ) ₃ (4.2 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n -, the average value of the number n of repeating units was 200.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.09(s),0.40-0.62(4H,m),0.90(3H,t),1.20-1.32(4H,m),1.62(6H,d),4.85-5.15(6H,m),5.82(3H,tdd)。

Example 7

R-CH obtained in Synthesis example 7 ₂ CH ₂ Si(CH ₂ CH＝CH ₂ ) ₃ (3.6 g), toluene (4 mL), a xylene solution of the Kadster catalyst (2%, 54. Mu.L), aniline (9 mg), and trimethoxysilane (0.27 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CH ₂ CH ₂ Si(CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ ) ₃ (3.3 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n -, the average value of the number n of repeating units was 200.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.08(s),0.39-0.73(12H,m),0.85(3H,t),1.21-1.32(4H,m),1.420-1.65(6H,m),3.55(27H,s)。

Synthesis example 8

R (-ch=ch) ₂ ) ₂ (5 g, gelest, DMS-V21), toluene (10 g), trichlorosilane (1.48 g), and a xylene solution of the Kadster catalyst (2%, 0.41 mL) were mixed and stirred at 60℃for 4 hours. After leaving to cool to room temperature, the solvent was distilled off under reduced pressure, and then dissolved in tetrahydrofuran (10 g), and allyl magnesium chloride (1.0 mol/L, 12.1 mL) was added under ice-cooling. After gradually warming to room temperature and stirring for 17 hours, a saturated aqueous sodium chloride solution was added. The insoluble material was filtered through a celite pad, and the filtrate was extracted with dichloromethane. The solvent was distilled off under reduced pressure to give R < CH > ₂ CH ₂ Si{CH ₂ CH＝CH ₂ } ₃ ] ₂ (4.4 g). Wherein R is-Si (CH) ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n -the average value of the number n of repeating units is 52.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.08(s),0.38-0.63(4H,m),1.65(6H,d),4.81-5.13(6H,m),5.80(3H,tdd)。

Example 8

R- [ CH ] obtained in Synthesis example 8 ₂ CH ₂ Si{CH ₂ CH＝CH ₂ } ₃ ] ₂ (3g) Toluene (6 mL), a xylene solution of the Kadset catalyst (2%, 0.25 mL), aniline (41 mg), and trimethoxysilane (1.25 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R- [ CH ] ₂ CH ₂ Si{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ ] ₂ (2.7 g). Wherein R is-Si (CH) ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n -the average value of the number n of repeating units is 52.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.10(s),0.33-0.75(16H,m),1.45-1.68(12H,m),3.52(27H,s)。

Synthesis example 9

2, 2-diallyl-4-penten-1-amine (2 g), triethylene glycol 2-bromoethyl methyl ether (8.9 g), 1, 8-diazabicyclo [5.4.0 ]7-undecene (5.0 g) was dissolved in cyclopentyl methyl ether (6 mL) and stirred at 80℃for 6 hours. After cooling to room temperatureWashing with sodium bicarbonate aqueous solution and water, concentrating under reduced pressure to obtain PG-NHCH ₂ C(CH ₂ CH＝CH ₂ ) ₃ (2.9 g). Wherein PG is CH ₃ (OCH ₂ CH ₂ ) ₄ －。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：2.05(d,J＝7.3Hz,6H),2.41-2.47(m,2H),2.76-2.81(m,2H),3.37(s,3H),3.59-3.65(m,14H),5.00-5.10(m,6H),5.77-5.88(m,3H)。

Synthesis example 10

R-COOH (3 g) and PG-NHCH obtained in Synthesis example 4 were subjected to a reaction ₂ C(CH ₂ CH＝CH ₂ ) ₃ (0.34 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (0.18 g), 4-dimethylaminopyridine (7.8 mg) and methylene chloride (3 mL) were mixed and stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with hydrochloric acid and water, and concentrated under reduced pressure to give R-CON (PG) -CH ₂ C(CH ₂ CH＝CH ₂ ) ₃ (2.5 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ －(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -, PG is CH ₃ (OCH ₂ CH ₂ ) ₄ -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.12-0.31(m),0.50-0.58(m,4H),0.89(t,J＝6.9Hz,3H),1.24-1.34(m,4H),1.60-1.67(m,2H),2.02(d,J＝7.3Hz,6H),3.25(s,2H),3.37(s,3H),3.49(t,J＝6.6Hz,2H),3.56-3.65(m,16H),3.98(s,2H),5.05-5.16(m,6H),5.80-5.94(m,3H)。

Example 9

R-CON (PG) -CH obtained in Synthesis example 10 ₂ C(CH ₂ CH＝CH ₂ ) ₃ (1.7 g), toluene (4 mL), a xylene solution of the Kadster catalyst (2%, 0.078 mL), aniline (12 mg), and trimethoxysilane (0.39 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CON (PG) -CH ₂ C{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ (1.5 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ (OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -, PG is CH ₃ (OCH ₂ CH ₂ ) ₄ -, the average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.11-0.31(m),0.52-0.64(m,10H),0.93(t,J＝7.1Hz,3H),1.22-1.36(m,16H),1.64-1.68(m,2H),3.15(s,2H),3.35(s,3H),3.46-3.49(m,2H),3.55-3.68(m,43H),3.95(s,2H)。

Synthesis example 11

1, 3-diallyl-isocyanuric acid (3.0 g) was dissolved in dimethylacetamide (14 mL). Potassium carbonate (1.5 g) was added thereto, and the mixture was heated with stirring. Addition of R-OSO dissolved in dimethylacetamide ₂ CF ₃ (6.0 g), further heating and stirring were continued. By passing through ¹ The end point of the reaction was confirmed by H-NMR, and the reaction mixture was washed with pure water and concentrated under reduced pressure to give the following compound. Wherein R-OSO ₂ CF ₃ (6.0 g) was converted by terminal alcohol (X-22-170 DX) of Xinyue chemical Co. R is CH ₃ (CH ₂ ) ₃ －(Si(CH ₃ )O) _n －Si(CH ₃ ) ₂ －(CH ₂ ) ₃ －O－(CH ₂ ) ₂ -. The average value of the number n of repeating units was 78.

Example 10

The compound (5 g) obtained in synthesis example 11, toluene (30 mL), a xylene solution of a cassiterite catalyst (2%, 0.17 mL), aniline (29 mg) and trimethoxysilane (0.9 mL) were mixed, stirred at room temperature overnight, and then concentrated under reduced pressure, thereby obtaining the following compound. The average value of the number n of repeating units was 78.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.33-0.36(m),0.4-0.6(m,4H),0.85-0.92(m,7H),1.26-1.32(m,4H),1.54-1.64(m,2H),1.71-1.79(m,4H),3.42(t,2H,6.8Hz),3.54-3.60(m,18H)3.64(d,2H,6.0Hz),3.85(d,4H,7.2Hz),4.09(d,2H,6.0Hz)。

Synthesis example 12

R- (ch=ch) ₂ ) ₂ (5g) Toluene (10 g), trichlorosilane (0.65 g), and a xylene solution of a Kadster catalyst (2%, 0.18 mL) were mixed and stirred at 60℃for 4 hours. After leaving to cool to room temperature, the solvent was distilled off under reduced pressure, and then dissolved in tetrahydrofuran (10 g), and allyl magnesium chloride (1.0 mol/L, 5.3 mL) was added under ice-cooling. After gradually warming to room temperature and stirring for 17 hours, a saturated aqueous sodium chloride solution was added. The insoluble material was filtered through a celite pad, and the filtrate was extracted with dichloromethane. The solvent was distilled off under reduced pressure to give R- (CH) ₂ CH ₂ Si(CH ₂ CH＝CH ₂ ) ₃ ) ₂ (4.4 g). Wherein R is-SiPh ₂ (OSiPh ₂ ) _m －(OSi(CH ₃ ) ₂ ) _n The average values of the repeating unit numbers m and n were 26 and 87, respectively.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.18-0.16(m),0.38-0.63(4H,m),1.65(6H,d),4.81-5.13(6H,m),5.80(3H,tdd),7.12-7.48(m),7.50-7.74(m)。

Example 11

R- (CH) obtained in Synthesis example 12 ₂ CH ₂ Si(CH ₂ CH＝CH ₂ ) ₃ ) ₂ (3g) Toluene (6 mL), a xylene solution of the Kadset catalyst (2%, 0.11 mL), aniline (18 mg), and trimethoxysilane (0.55 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R- [ CH ] ₂ CH ₂ Si{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ ] ₂ (2.8 g). Wherein R is-SiPh ₂ (OSiPh ₂ ) _m －(OSi(CH ₃ ) ₂ ) _n The average values of the repeating unit numbers m and n were 26 and 87, respectively.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.10(s),0.31-0.77(m,32H),1.43-1.70(m,12H),3.50-3.61(s,54H)。

Synthesis example 13

R-COOH (2.11 g), diallylamine (18 mL), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (0.14 g), 4-dimethylaminopyridine (6 mg) and methylene chloride (4.0 g) obtained in Synthesis example 4 were mixed and stirred overnight at room temperature. Diluted with methylene chloride, washed with hydrochloric acid and water, and concentrated under reduced pressure to give R-CON (CH) ₂ CH＝CH ₂ ) ₂ (1.88 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ －(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -. The average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：0.04-0.09(m),0.51-0.56(m),0.86-0.90(t),1.25-1.35(m),1.60-1.67(m),3.45-3.49(t),3.91-3.99(dd),4.14(s),5.12-5.21(m),5.70-5.81(m)。

Example 12

R-CON (CH) obtained in Synthesis example 13 ₂ CH＝CH ₂ ) ₂ (1.7 g), toluene (1.7 g), a xylene solution of a Kanster catalyst (2%, 0.20 mL), pyridine (10 mg) and trimethoxysilane (0.32 mL) were mixed, stirred at room temperature overnight, and concentrated under reduced pressure to give R-CON { CH } ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₂ (1.97 g). Wherein R is CH ₃ CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ －(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₃ －OCH ₂ -. The average value of the number n of repeating units was 57.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.08-0.08(m),0.51-0.55(m),0.86-0.88(t),1.25-1.32(m),1.60-1.66(m),3.56-3.64(m)。

Synthesis example 14

Methyl 10-undecenoate (5.02 g), toluene (1.7 g), a xylene solution of a Kadster catalyst (2%, 0.3 mL) and pyridine (0.1 mL) were added, and after cooling to 5℃or below using an ice bath, 1, 3-pentamethyldisiloxane (20 mL) was added and stirred at 60℃for 3 hours. After that, trimethoxysilane (0.32 mL) was mixed, stirred at room temperature overnight, and concentrated under reduced pressure to give (CH) ₃ ) ₃ SiO(CH ₃ ) ₂ Si(CH ₂ ) ₁₀ COOMe(8.62g)。

Synthesis example 15

R-COOMe (3.0 g), toluene (8.7 mL), 1,5, 7-triazabicyclo [4.4.0 were added separately]After dec-5-en (0.140 g), 2-diallyl-4-penten-1-amine (0.75 g), stirring was carried out at 75℃for 24 hours. Diluting the mixture with toluene, washing with hydrochloric acid and water, concentrating under reduced pressure to obtain R-CONH-CH ₂ C(CH ₂ CH＝CH ₂ ) ₃ (2.74g)。

R is (CH) ₃ ) ₃ Si－OSi(CH ₃ ) ₂ －(CH ₂ ) ₁₀ －。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.01-0.04(m),0.45-0.49(m),1.23-1.26(m),1.56-1.64(m),2.05(s),2.15-2.19(t),3.22(s),3.82-3.85(m),5.05-5.16(m),5.75-5.84(m),6.24(s)。

Example 13

R-CONH-CH obtained in Synthesis example 14 ₂ C(CH ₂ CH＝CH ₂ ) ₃ (2.07 g), toluene (2 g), a xylene solution of a Kadster catalyst (2%, 0.2 mL), pyridine (0.1 mL), and trimethoxysilane (0.5 mL) were mixed. The mixture was stirred at room temperature overnight and concentrated under reduced pressure to give R-CONH-CH ₂ C{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ (2.53g)。

R is (CH) ₃ ) ₃ Si－OSi(CH ₃ ) ₂ －(CH ₂ ) ₁₀ －。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.14-0.05(m),0.46-0.50(t),0.54-0.63(m),1.25-1.27(m),1.57-1.66(m),2.12-2.16(t),3.17(s),3.56(s),6.54(s)。

Comparative example 1

The following compounds were synthesized according to the method described in Japanese patent application laid-open No. 2019-44179. CH (CH) ₃ O(CH ₂ CH ₂ O) _n－ ₁ CH ₂ C(O)NHCH ₂ C{CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ } ₃ The average value of the number n of repeating units was 22.

Synthesis example 16

R-COOH (5 g), allylamine (0.59 g), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (0.99 g), 4-dimethylaminopyridine (42 mg) and methylene chloride (15 mL) were mixed and stirred overnight at room temperature. Diluted with methylene chloride, washed with hydrochloric acid and water, and concentrated under reduced pressure to give R-CONH-CH ₂ CH＝CH ₂ (3.82g)。

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.20-0.30(m),0.48-0.56(m,2H),1.18-1.37(m,14H),1.58-1.69(m,2H),2.19(t,2H,7.6Hz),3.87-3.90(m,2H),5.11-5.20(m,2H),5.49(brs,1H),5.77-5.89(m,1H)。

Comparative example 2

R-CONH-CH ₂ CH＝CH ₂ (2g) Toluene (5 mL), a xylene solution of a Kadset catalyst (2%, 0.10 mL), aniline (16 mg) and trimethoxysilane (0.5 mL) were mixed, stirred overnight at room temperature, and concentrated under reduced pressure to give R-CON-CH ₂ CH ₂ CH ₂ Si(OCH ₃ ) ₃ (2.11g)。

Comparative example 3

According to the method described in Japanese patent application laid-open No. 2014-84405, the above is usedThe reaction mixture (CH) obtained in Synthesis example 13 ₃ ) ₃ Si－(OSi(CH ₃ ) ₂ ) _n －(CH ₂ ) ₁₀ －CONH－CH ₂ CH＝CH ₂ (average value of the number n of repeating units was 19), the following compounds were synthesized.

¹ H NMR(CDCl ₃ ,400MHz)δ[ppm]：-0.20-0.30(m),0.38-0.68(m,16H),1.20-1.38(m,14H),1.46-1.68(m,4H),2.10-2.23(m,2H),3.18-3.26(m,1H),3.44-3.65(m,19H)。

< formation of surface treatment layer >

[ spin coating treatment ]

The compounds of examples 1 to 5 and 10 and comparative example 1 were diluted into 1.5wt% isopropyl alcohol solutions, respectively, to obtain surface treatment agents 1 to 7. For the surface treatment agents 1 to 7, UV/O was performed on a 50mm×50mm glass substrate for 10 minutes ₃ After treatment and dry cleaning, spin coating was performed at 3000rpm for 30 seconds. Thereafter, heat treatment was performed at 100 ℃ for 2 hours using an oven, thereby obtaining a surface-treated layer.

< evaluation >

[ measurement of contact Angle ]

For measuring the contact angle, a full-automatic contact angle meter DropMaster700 (manufactured by Kyowa Kagaku Co., ltd.) was used at 25 ℃. Specifically, the static contact angle was measured by horizontally standing a substrate having a surface treatment layer to be measured, dropping water onto the surface of the substrate using a microinjector, and taking a still image 1 second after dropping the solution using a video microscope. The static contact angle was measured at 5 different points of the surface treatment layer of the substrate, and the calculated average value was used. The contact angle of oleic acid was measured 4 seconds after the liquid was applied at a liquid level of 2. Mu.L.

TABLE 1

Compounds of formula (I)	Water contact angle (degree)	Contact angle of oleic acid (degree)
			Example 1	99.1	50.9
Example 2	101.2	54.9
			Example 3	97.2	45.5
Example 4	104.9	51.5
			Example 5	97.4	47.0
Example 10	104.0	52.0
			Comparative example 1	37.8	20.0

< formation of surface treatment layer >

The compounds of examples 1,3, 4, 6 to 13 and comparative examples 2 to 3 were diluted to 20wt% of a 1, 3-bis (trifluoromethyl) benzene solution, respectively, to obtain surface treatment agents 5 to 9. The surface treatment agents 8 to 18 prepared above were vacuum-deposited on chemically strengthened glass (Gorilla glass, manufactured by Corning Co., ltd., thickness: 0.7 mm).

Specifically, 0.1g of the surface treatment agent was filled in a molybdenum boat in a vacuum deposition apparatus, and the vacuum deposition apparatus was evacuated to a pressure of 3.0X10 ^-3 Pa or below. Thereafter, a silicon dioxide film was formed by vapor deposition of silicon dioxide having a thickness of 7nm by electron beam vapor deposition, and then a surface treatment layer was formed by heating the boat by resistance heating.

< evaluation >

[ evaluation of abrasion resistance ]

The evaluation test for the ink removability was performed on the evaluation sample after the abrasion resistance test, and the fingerprint removability was evaluated on the same evaluation basis. The better the fingerprint removability after the rubbing test, the smaller the performance degradation due to rubbing and the better the rubbing resistance.

(initial evaluation)

As an initial evaluation (number of rubs 0 times), after the surface treatment layer was formed, the static contact angle of water was measured after wiping off the excessive components on the surface.

(evaluation after abrasion resistance test)

The surface-treated layer was formed by using a friction tester (manufactured by hoku corporation) and was reciprocated 3000 times (or 6000 times) under the following conditions.

Friction piece: BEMCOT M-3II (product name, manufactured by Asahi Kasei Co., ltd.)

Distance of movement (single pass): 60mm

Speed of movement: 8,400 mm/min

Load: 100g/3cm ²

[ evaluation of ink removability ]

After the formation of the surface treatment layer, the excessive components on the surface were wiped off as an evaluation sample. The evaluation was performed after the number of rubs was 0 times, 3000 times, and 6000 times. After a line was drawn on the surface layer of the evaluation sample with an oily felt-tip pen (extremely thick black mark pen, product name, ZEBRA co., ltd. Production), becot M-3II was used as a friction member at a moving speed: 70rpm, load: 100g/3cm ² After the friction was performed 50 times under the conditions of (a) and (b) the adhesion state of the oily ink (line) was visually observed, and the ink removability (initial ink removability) was evaluated according to the following criteria.

Excellent (excellent): the removal rate of the oily ink is more than 90%.

O (good): the removal rate of the oily ink is more than 60% and less than 90%.

Delta (cocoa): the removal rate of the oily ink is more than 30% and less than 60%.

X (inferior): the removal rate of the oily ink is less than 30%.

TABLE 2

Preparation of the treatment agent solution

The compounds of examples 1 and 4 were diluted to 10wt% with the solvent (S) shown in Table 3 to obtain surface treatment agents 1 to 13.

< test of compatibility >)

The surface treatments 1 to 13 thus prepared were allowed to stand in a laboratory at 23 to 27℃for 10 minutes, and the state of the surface treatments was visually observed and evaluated according to the following criteria.

((good): a transparent solution which is uniformly mixed.

X (inferior): non-uniform, and separated into two phases.

< test of storage stability >

The surface treatments 1 to 13 prepared above were allowed to stand at 23 to 27℃for 7 days under light shielding, and then the state of the surface treatments was visually observed and evaluated according to the following criteria.

Excellent (excellent): the solution was homogeneous, free from turbidity and free from formation of solid components.

((good): no solid component was formed in the liquid medicine, but the solid component was visible on the liquid surface.

Delta (cocoa): the liquid medicine was confirmed to have fluidity while having a solid content therein.

X (inferior): gelation occurs and there is no fluidity.

TABLE 3

	Compounds of formula (I)	Solvent (S)	Compatibility with each other	Storage stability
					Surface treating agent 1	Example 1	Isopropyl alcohol	○	×
Surface treating agent 2	Example 1	Ethanol	○	×
					Surface treating agent 3	Example 1	Dimethylacetamide	○	△
Surface treating agent 4	Example 1	Butyl acetate	○	△
					Surface treating agent 5	Example 1	Cyclopentyl methyl ether	○	◎
Surface treating agent 6	Example 1	1, 3-bis (trifluoromethyl) benzene	○	○
					Surface treating agent 7	Example 1	Novec7200	×	—
Surface treating agent 8	Example 1	Novec7300	×	—
					Surface treating agent 9	Example 1	Octamethyltrisiloxane	○	◎
Surface treating agent 10	Example 1	Hexamethyldisiloxane	○	◎
					Surface treating agent 11	Example 4	1, 3-bis (trifluoromethyl) benzene	○	○
Surface treating agent 12	Example 4	Octamethyltrisiloxane	○	◎
					Surface treating agent 13	Example 4	Hexamethyldisiloxane	○	◎

< fingerprint erasability evaluation >)

After forming a surface treatment layer by using the surface treatment agents 5, 6 and 11 to 13 according to the method described in the above < formation of surface treatment layer >, the excessive components on the surface of the substrate were wiped off to prepare an evaluation sample. Sebum was attached to the evaluation sample with a force of 27N. Next, as for fingerprint marks on the surface layer of the evaluation sample, BEMCOT M-3II was attached to a 1kg cylindrical weight, and the fingerprint adhesion state after wiping off the surface layer fingerprint was measured by a haze meter 10 times in one direction under the following conditions. The results are shown in table 4 below.

Cleaning cloth: BEMCOT M-3II (product name, manufactured by Asahi Kasei Co., ltd.)

Distance of movement (single pass): 60mm

Speed of movement: 8,400 mm/min

Load: 1000g/3cm ²

Excellent (excellent): almost no fingerprint mark was seen.

((good): the fingerprint is slightly visible.

Delta (cocoa): the fingerprint is clearly visible although it is pale.

X (inferior): clearly visible.

< haze measurement >)

The haze value of the above-mentioned evaluation sample subjected to fingerprint wiping evaluation was measured by using a haze meter (NDH-7000, manufactured by Nippon Denshoku Co., ltd.). The results are shown in table 4 below.

TABLE 4

Industrial applicability

The surface treatment agent of the present invention can be suitably used in various applications.

Claims

1. A siloxane-containing silane compound represented by the following formula (1) or (2), characterized by,

R ^S1 _α -X ^A -R ^H _β (1)

R ^H _γ -X ^A -R ^S2 -X ^A -R ^H _γ (2)

in the method, in the process of the invention,

R ^S1 each occurrence is independently R ¹ -R ^S -R ² _q -；

R ^S2 is-O _p -R ^S -R ² _q -；

R ¹ is a hydrocarbon group;

R ² is-SiR ³ ₂ -；

R ³ Each independently at each occurrence is a hydrocarbyl group;

p is 0 or 1;

q is each independently 0 or 1;

the R is ^H More than 2 Si atoms bonded with hydroxyl or hydrolytic groups;

X ^A each independently is a single bond or a 2-10 valent organic group;

alpha is an integer of 1 to 9;

beta is an integer of 1 to 9;

gamma is an integer of 1 to 9.

2. The siloxane-containing silane compound according to claim 1,

R ^S is- (SiR) ³ ₂ -O) _a -，

R ³ Each independently at each occurrence is a hydrocarbyl group,

a is 2 to 1500.

3. The siloxane-containing silane compound according to claim 1 or 2,

R ³ each occurrence of which is independently C which may be substituted by a halogen atom _1-6 Alkyl or aryl.

4. A siloxane-containing silane compound according to claim 1 to 3,

R ³ each occurrence is independently methyl or phenyl.

5. The siloxane-containing silane compound according to claim 1 to 4,

a is 10 to 500.

6. The siloxane-containing silane compound according to claim 1 to 5,

R ^H is a group represented by the following formula (S1), (S2), (S3) or (S4),

-SiR ^a1 _k1 R ^b1 ₁₁ R ^c1 _m1 (S2)

-CR ^d1 _k2 R ^e1 ₁₂ R ^f1 _m2 (S3)

-NR ^g1 R ^h1 (S4)

in the method, in the process of the invention,

R ¹² each independently at each occurrence is a 1-valent organic group;

n1 is defined in each (SiR ¹¹ _n1 R ¹² _3-n1 ) Each of the units is independently an integer of 0 to 3;

t is independently an integer of 2 or more for each occurrence;

R ¹⁴ at each timeAt the occurrence of each is independently a hydrogen atom, a halogen atom or-X ¹¹ -SiR ¹¹ _n1 R ¹² _3-n1 ；

R ^a1 each occurrence is independently-Z ¹ -SiR ²¹ _p1 R ²² _q1 R ²³ _r1 ；

Z ¹ Each independently at each occurrence a 2-valent organic group;

R ²¹ each occurrence is independently-Z ^1′ -SiR ^21′ _p1′ R ^22′ _q1′ R ^23′ _r1′ ；

R ²³ each independently at each occurrence is a 1-valent organic group;

p1 is independently at each occurrence an integer from 0 to 3;

q1 is independently at each occurrence an integer from 0 to 3;

r1 is independently at each occurrence an integer from 0 to 3;

Z ^1′ each independently at each occurrence a 2-valent organic group;

R ^21′ each occurrence is independently-Z ^1″ -SiR ^22″ _q1″ R ^23″ _r1″ ；

R ^23′ each independently at each occurrence is a 1-valent organic group;

p1' is independently at each occurrence an integer from 0 to 3;

q1' is independently at each occurrence an integer from 0 to 3;

r1' is independently at each occurrence an integer from 0 to 3;

Z ^1″ each independently at each occurrence a 2-valent organic group;

R ^23″ each independently at each occurrence is a 1-valent organic group;

q1 "is independently at each occurrence an integer from 0 to 3;

r1' is independently at each occurrence an integer from 0 to 3;

R ^c1 each independently at each occurrence is a 1-valent organic group;

k1 is independently at each occurrence an integer from 0 to 3;

11 is independently an integer from 0 to 3 for each occurrence;

m1 is independently at each occurrence an integer from 0 to 3;

R ^d1 each occurrence is independently-Z ² -CR ³¹ _p2 R ³² _q2 R ³³ _r2 ；

R ³¹ each occurrence is independently-Z ^2′ -CR ^32′ _q2′ R ^33′ _r2′ ；

R ³² Each occurrence is independently-Z ³ -SiR ³⁴ _n2 R ³⁵ _3-n2 ；

p2 is independently at each occurrence an integer from 0 to 3;

q2 is independently at each occurrence an integer from 0 to 3;

r2 is independently at each occurrence an integer from 0 to 3;

R ^32′ each occurrence is independently-Z ³ -SiR ³⁴ _n2 R ³⁵ _3-n2 ；

q2' is independently at each occurrence an integer from 0 to 3;

r2' is independently at each occurrence an integer from 0 to 3;

R ³⁵ each independently at each occurrence is a 1-valent organic group;

n2 is independently at each occurrence an integer from 0 to 3;

R ^e1 each occurrence is independently-Z ³ -SiR ³⁴ _n2 R ³⁵ _3-n2 ；

k2 is independently at each occurrence an integer from 0 to 3;

12 is independently an integer from 0 to 3 for each occurrence;

m2 is independently at each occurrence an integer from 0 to 3;

R ^g1 and R is ^h1 Each occurrence is independently-Z ⁴ -SiR ¹¹ _n1 R ¹² _3-n1 、-Z ⁴ -SiR ^a1 _k1 R ^b1 ₁₁ R ^c1 _m1 or-Z ⁴ -CR ^d1 _k2 R ^e1 ₁₂ R ^f1 _m2 ；

Z ⁴ Each occurrence of which is independently a single bond, an oxygen atom or a 2-valent organic groupA bolus;

wherein at least 2 Si atoms to which a hydroxyl group or a hydrolyzable group is bonded are present in the formulas (S1), (S2), (S3) and (S4).

7. The siloxane-containing silane compound according to claim 6,

the group represented by the formula (S1) is a group represented by the following formula (S1-b),

wherein R is ¹¹ 、R ¹² 、R ¹³ 、X ¹¹ The meanings of n1 and t are the same as those described in the formula (S1).

8. The siloxane-containing silane compound according to claim 6,

R ^H Each occurrence is independently a group represented by the formula (S2), (S3) or (S4).

9. The siloxane-containing silane compound according to claim 6,

R ^H each occurrence of which is independently a group represented by the formula (S2) or (S3).

10. The siloxane-containing silane compound according to claim 6,

R ^H each occurrence is independently a group represented by the formula (S3) or (S4).

11. The siloxane-containing silane compound according to claim 6,

R ^H each occurrence of which is independently a group represented by the formula (S3).

12. The siloxane-containing silane compound according to any one of claim 1 to 11,

alpha, beta and gamma are 1.

13. The siloxane-containing silane compound according to any one of claim 1 to 12,

X ^A is a single bond or of the formula: - (R) ⁵¹ ) _p5 -(X ⁵¹ ) _q5 The illustrated 2-valent organic groups,

in the method, in the process of the invention,

s5 is an integer of 1 to 20,

X ⁵¹ is- (X) ⁵² ) ₁₅ -，

X ⁵² Each occurrence is independently selected from the group consisting of-O-, -S-, O-phenylene m-phenylene or p-phenylene, -CO-, -C (O) O-, -CONR ⁵⁴ -、-O-CONR ⁵⁴ -、-NR ⁵⁴ -and- (CH) ₂ ) _n5 The group in (c) is a group,

n5 is independently an integer of 1 to 20 for each occurrence,

15 is an integer of 1 to 10,

p5 is either 0 or 1 and,

q5 is either 0 or 1 and,

here, at least one of p5 and q5 is 1, and the order in which the repeating units p5 or q5 are present and bracketed is arbitrary.

14. The siloxane-containing silane compound according to any one of claim 1 to 12,

X ^A are each independently a single bond, C _1-20 Alkylene, - (CH) ₂ ) _s5 -X ⁵³ -、-X ⁵³ -(CH ₂ ) _t5 -or- (CH) ₂ ) _s5 -X ⁵³ -(CH ₂ ) _t5 The illustrated 2-valent organic groups,

in the method, in the process of the invention,

X ⁵³ is a single bond, -O-, -CO-, -CONR ⁵⁴ -、-O-CONR ⁵⁴ -、-O-(CH ₂ ) _u5 -CONR ⁵⁴ -or-O- (CH) ₂ ) _u5 -CO-，

R ⁵⁴ Each occurrence of which is independently a hydrogen atom, phenyl group, C _1-6 Alkyl or a group containing an oxyalkylene group having 1 to 10 carbon atoms,

s5 is an integer of 1 to 20,

t5 is an integer of 1 to 20,

u5 is an integer of 1 to 20.

15. The siloxane-containing silane compound according to any one of claim 1 to 12,

X ^A each independently is- (CH) ₂ ) _s5 -O-(CH ₂ ) _t5 -、-(CH ₂ ) _s5 -CONR ⁵⁴ -(CH ₂ ) _t5 -、-(CH ₂ ) _s5 -O-(CH ₂ ) _u5 -CO-or- (CH) ₂ ) _s5 -O-(CH ₂ ) _u5 -CONR ⁵⁴ -(CH ₂ ) _t5 The illustrated 2-valent organic groups,

in the method, in the process of the invention,

s5 is an integer of 1 to 20,

t5 is an integer of 1 to 20,

u5 is an integer of 1 to 20.

16. The siloxane-containing silane compound according to any one of claim 1 to 11,

X ^A each independently is a 3 to 10 valent organic group.

17. The siloxane-containing silane compound according to any one of claim 1 to 11,

X ^A each independently is a group represented by the following formula,

wherein X is ^a Each independently is a single bond or a 2-valent organic group.

18. The siloxane-containing silane compound according to claim 17,

xa are each independently of the other the following formula: - (CX) ¹²¹ X ¹²² ) _x1 -(X ^a1 ) _y1 -(CX ¹²³ X ¹²⁴ ) _z1 The group indicated is chosen from the group indicated,

in the method, in the process of the invention,

X ¹²¹ ～X ¹²⁴ h, OH OR-OSi (OR) ¹²¹ ) ₃ OSi (OR) ¹²¹ ) ₃ Wherein R is ¹²¹ Each independently represents an alkyl group having 1 to 4 carbon atoms,

X ^a1 is-C (=O) NH-, -NHC (=O) -, -O-, -C (=O) O-, -OC (=O) O-, -NHC (=O) NH-, -NR ¹²² -、-C(＝O)-NR ¹²² -、-NR ¹²² -C (=o) -or S,

R ¹²² is C _1-6 Is used for the formation of a hydrocarbon chain,

x1 is an integer of 0 to 10,

y1 is either 0 or 1 and,

z1 is an integer of 1 to 10.

19. A composition comprising, as a main ingredient,

a siloxane-containing silane compound according to any one of claims 1 to 18.

20. A composition comprising, as a main ingredient,

at least one compound comprising the siloxane-containing silane compound according to any one of claims 1 to 18 and a condensate obtained by condensing at least a part of the siloxane-containing silane compound.

21. The composition of claim 19 or 20,

and further comprises R selected from ⁷¹ OR ⁷² 、R ⁷³ _n8 C ₆ H _6-n8 、R ⁷⁴ R ⁷⁵ R ⁷⁶ Si-(O-SiR ⁷⁷ R ⁷⁸ ) _m8 -R ⁷⁹ Sum (OSiR) ⁷⁷ R ⁷⁸ ) _m9 The solvent in the compounds shown is chosen to be,

in the method, in the process of the invention,

m8 is an integer of 1 to 6,

m9 is an integer of 3 to 8,

n8 is an integer of 0 to 6.

22. The composition of claim 21, wherein the composition comprises,

the solvent is R ⁷⁴ R ⁷⁵ R ⁷⁶ Si-(O-SiR ⁷⁷ R ⁷⁸ ) _m8 -R ⁷⁹ 。

23. The composition of claim 21 or 22,

the solvent is hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octamethylcyclotetrasiloxane or decamethylcyclopentasiloxane.

24. The composition according to any one of claim 19 to 23,

the composition is a surface treatment agent.

25. The composition according to any one of claim 19 to 24,

the composition is used for vacuum evaporation.

26. The composition according to any one of claim 19 to 24,

the composition is used for wet coverage.

27. A granule, which is characterized in that,

a composition according to any one of claims 19 to 26.

28. An article, comprising:

A substrate; and

a layer formed from the siloxane-containing silane compound of any one of claims 1 to 18 or the composition of any one of claims 24 to 26 on the substrate.

29. The article of claim 28, wherein the article comprises,

the article is an optical component.

30. The article of claim 28, wherein the article comprises,

the article is a display.

31. A compound represented by the following formula (1-a) or (2-a), characterized in that,

R ^S1 -X ^B (1-a)

X ^B -R ^S2 -X ^B (2-a)

in the formula (1-a) or (2-a),

R ^S1 each occurrence is independently R ¹ -R ^S -R ² _q -；

R ^S2 is-O _p -R ^S -R ² _q -；

R ¹ is a hydrocarbon group;

R ² is-SiR ³ ₂ -；

R ³ Each independently at each occurrence is a hydrocarbyl group;

p is 0 or 1;

q is each independently 0 or 1;

X ^B each independently is- (CH) ₂ ) _s6 -X ⁵³ -X ⁵⁴ 、-X ⁵³ -(CH ₂ ) _t6 -X ⁵⁴ Or- (CH) ₂ ) _s6 -X ⁵³ -(CH ₂ ) _t6 -X ⁵⁴ ，

Wherein X is ⁵³ is-O-, -CO-, -CONR ⁷⁴ -、-O-CONR ⁷⁴ -、-O-(CH ₂ ) _u6 -CONR ⁷⁴ -or-O- (CH) ₂ ) _u6 -CO-, a single bond,

X ⁵⁴ is R ⁷⁵ 、-NR ⁷⁵ ₂ 、-SiR ⁷⁵ ₂ R ⁷⁶ 、-SiR ⁷⁵ ₃ 、-CR ⁷⁵ ₂ R ⁷⁵ 、-CR ⁷⁵ ₃ 、-SiCl ₂ R ⁷⁶ 、-SiCl ₃ Or (b)

R ⁷⁵ is-CH=CH ₂ or-CH ₂ -CH＝CH ₂ ，

R ⁷⁶ Is an organic group having a valence of 1,

R ⁷⁴ each occurrence of which is independently a hydrogen atom, phenyl group, C _1-6 Alkyl or a group containing an oxyalkylene group having 1 to 10 carbon atoms,

s6 is an integer of 1 to 20,

t6 is an integer of 1 to 20,

u6 is an integer of 1 to 20.

32. A compound according to claim 31 wherein,

X ⁵³ is-CONR ⁷⁴ -。

33. A compound according to claim 31 wherein,

X ⁵⁴ is-Si (CH) ₂ CH＝CH ₂ ) ₃ or-SiCl ₃ 。

34. A compound according to claim 31 wherein,

X ⁵⁴ is that

35. A compound according to claim 31 wherein,

-X ⁵³ -X ⁵⁴ is-CON (CH) ₂ CH＝CH ₂ ) ₂ 、-CONHCH ₂ C(CH ₂ CH＝CH ₂ ) ₃ 。