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KR-102963336-B1 - Silane compound including fluorine containing (poly)ether group, composition including the same, film formed from the composition, display device, and article

KR102963336B1KR 102963336 B1KR102963336 B1KR 102963336B1KR-102963336-B1

Abstract

A composition comprising a silane compound having a fluorine-containing (poly)ether group represented by the following chemical formula 1, a film formed therefrom, a laminate, a display device, an article, and a method for manufacturing a laminate are provided. <Chemical Formula 1> Rf-(L 1 ) p1 -Q1-(L 2 ) p2 -Si(R 1 )(R 2 )-(L 3 ) p3 -Si(R 3 )(R 4 )(R 5 ) In Chemical Formula 1, Rf represents a fluorine-containing (poly)ether group, and Q1, L1 to L5 , R1 to R5 , R9 to R13 , and p1 to p5 are as defined in the detailed description.

Inventors

  • 김하나
  • 박병하
  • 주경식
  • 홍성훈

Assignees

  • 삼성전자주식회사

Dates

Publication Date
20260508
Application Date
20190821

Claims (20)

  1. It is a silane compound having a fluorine-containing (poly)ether group, and the silane compound is a compound represented by the following chemical formula, or (C1) CF 3 O(CF 2 CF 2 O) n (CF 2 O) m -(CH 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 O(CF 2 CF 2 O) n (CF 2 O) m -(CF 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2- Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 O(CF 2 CF 2 O) n (CF 2 O) m -(CH 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 O(CF 2 CF 2 O) n (CF 2 O) m -(CF 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(CH 3 ),CF 3 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CH 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CF 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CH 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(CH 3 ), CF 3 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CF 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 Si(OCH 3 )(OCH 3 )(CH 3 ),CF 3 CF 2 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CH 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CF 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(OCH 3 ), CF 3 CF 2 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CH 2 ) 2 -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )-CH 2 -Si(OCH 3 )(OCH 3 )(CH 3 ), or CF 3 CF 2 CF 2 O(CF 2 CF 2 O) n (CF 2 O) m -(CF 2 ) 2 A silane compound having a fluorine-containing (poly ) ether group, wherein -C(=O)NH-(CH 2 ) 2 -NH-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )CH 2 Si(OCH 3 )(OCH 3 )(CH 3 ), and n and m are independently integers from 1 to 100.
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  7. In paragraph 1, A silane compound having a fluorine-containing (poly)ether group, wherein the weight-average molecular weight of the fluorine-containing (poly)ether group is 1,000 g/mol to 10,000 g/mol.
  8. A composition comprising a silane compound having a fluorine-containing (poly)ether group according to claim 1 or 7.
  9. In paragraph 8, A composition comprising a compound represented by the following chemical formula 3 further included in the above composition: <Chemical Formula 3> AL 6 -Si(R 5 )(R 6 )(R 7 ) In the above chemical formula 3, L6 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof, and R 5 to R 7 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and A is a halogen, a thiol group, an isocyanate group, or an amino group ( -NH₂ ), and At least one of R 5 to R 7 is a substituted or unsubstituted C1 to C20 alkoxy group, halogen atom, or hydroxyl group.
  10. In Paragraph 9, A composition in which the molar ratio of a silane compound having a fluorine-containing (poly)ether and a compound of Formula 3 in the above composition is 1:0.003 to 1:3.
  11. In Paragraph 9, The compound of Formula 3 is H 2 N-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )(OCH 3 ), H 2 N-(CH 2 ) 3 -Si(OCH 2 CH 3 )(OCH 2 CH 3 )(OCH 2 CH 3 ), H 2 N-(CH 2 ) 3 -Si(OCH 3 )(OCH 3 )(CH 3 ) or H 2 N-(CH 2 ) 3 -Si(OCH 2 CH 3 )(OCH 2 CH 3 )(CH 2 CH 3 ).
  12. In paragraph 8, A composition comprising a compound represented by the following chemical formula 2 further included in the above composition: <Chemical Formula 2> H 2 N-(L 2 ) p2 -Si(R 1 )(R 2 )-(L 3 ) p3 -Si(R 3 )(R 4 )(R 5 ) In the above chemical formula 2, L2 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, -( CH2 )m-NH-( CH2 )n-(m and n are independently integers from 1 to 10), or a combination thereof, and L3 is each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and p2 and p3 are each independently integers from 1 to 10, and R1 to R5 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and At least one of R1 to R5 is a substituted or unsubstituted C1 to C20 alkoxy group, halogen atom, or hydroxyl group, and Or one or more of R3 to R5 may be -( L4 ) p4 -Si( R9 )( R10 )( R11 ), or -( L4 ) p4 -Si( R12 )( R13 )-( L5 ) p5 -Si( R9 )( R10 )( R11 ), and the remainder R3 to R5 are substituted or unsubstituted C1 to C20 alkoxy groups, halogen atoms, or hydroxyl groups. R 9 to R 13 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, provided that at least one of R 9 to R 13 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group. L 4 and L 5 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and p4 and p5 are each independently integers from 1 to 10.
  13. In Paragraph 12, A composition in which the molar ratio of a silane compound having a fluorine-containing (poly)ether and a compound of Formula 2 in the above composition is a weight ratio of 1:0.5 to 1:3.
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  19. A film comprising a hydrolysis and condensation polymer of a silane compound having a fluorine-containing (poly)ether group according to claim 1 or 7.
  20. In Paragraph 19, A film comprising a compound represented by the following chemical formula 2, a compound represented by the following chemical formula 3, or a combination thereof. <Chemical Formula 2> H 2 N-(L 2 ) p2 -Si(R 1 )(R 2 )-(L 3 ) p3 -Si(R 3 )(R 4 )(R 5 ) In the above chemical formula 2, L2 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, -( CH2 )m-NH-( CH2 )n-(m and n are independently integers from 1 to 10), or a combination thereof, and L3 is each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and p2 and p3 are each independently integers from 1 to 10, and R1 to R5 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, provided that at least one of R1 to R5 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group. Or one or more of R3 to R5 may be -( L4 ) p4 -Si( R9 )( R10 )( R11 ), or -( L4 ) p4 -Si( R12 )( R13 )-( L5 ) p5 -Si( R9 )( R10 )( R11 ), and the remainder R3 to R5 are substituted or unsubstituted C1 to C20 alkoxy groups, halogen atoms, or hydroxyl groups. R 9 to R 13 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, provided that at least one of R 9 to R 13 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group. L4 and L5 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and p4 and p5 are each independently integers from 1 to 10, and <Chemical Formula 3> AL 6 -Si(R 5 )(R 6 )(R 7 ) In the above chemical formula 3, L6 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof, and R 5 to R 7 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and A is a halogen, a thiol group, an isocyanate group, or an amino group ( -NH₂ ), and At least one of R 5 to R 7 is a substituted or unsubstituted C1 to C20 alkoxy group, halogen atom, or hydroxyl group.

Description

Silane compound having a fluorine-containing (poly)ether group, composition including the same, film formed from the same, display device, and article The invention relates to a silane compound having a fluorine-containing (poly)ether group, a composition containing the same, a film, a laminate, a display device, and an article formed therefrom. Portable electronic devices such as smartphones or tablet PCs may have functional layers with various functions applied to them. In particular, as touch screen panels that recognize contact positions using fingers or tools have become common recently, functional layers may be applied to the surface of display panels to improve the slipperiness and touch sensitivity of the touch screen panel surface. However, these functional layers have poor durability and can be easily lost or destroyed by frequent contact, which can degrade their function, so improvements are required. FIG. 1 is a drawing for explaining the effects of coating a composition according to one embodiment onto a substrate. FIG. 2 is a cross-sectional view of a display device according to one embodiment. FIG. 3 is a cross-sectional view of a display device according to another embodiment. Hereinafter, a silane compound having a fluorine-containing (poly)ether group according to one embodiment, a composition including the same, a film formed therefrom, a laminate, a display device, an article, and a method for manufacturing a laminate will be described in more detail. A silane compound having a fluorine-containing (poly)ether group represented by the following chemical formula 1 is provided. <Chemical Formula 1> Rf-(L 1 ) p1 -Q1-(L 2 ) p2 -Si(R 1 )(R 2 )-(L 3 ) p3 -Si(R 3 )(R 4 )(R 5 ) In Chemical Formula 1, Rf represents a fluorine-containing (poly)ether group, and Q1 is -O-, -C(=O)O-, -OC(=O)O-, -NR a C(=O)O-, -C(=O)NR b- , -OC(=O)NR c S(=O)O-, or -CH 2 (C 6 H 4 )C(=O)-, and R a to R c are independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. L1 and L3 are independently substituted or unsubstituted C1 to C20 alkylene groups, substituted or unsubstituted C1 to C20 oxyalkylene groups, or a combination thereof, and L2 is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, -( CH2 )m-NH-( CH2 )n-(m and n are independently integers from 1 to 10), or a combination thereof, and p1 to p3 are independently integers from 1 to 10, and R1 to R5 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and At least one of R1 to R5 is a substituted or unsubstituted C1 to C20 alkoxy group, halogen atom, or hydroxyl group, and or one or more of R3 to R5 are -( L4 ) p4 -Si( R9 )( R10 )( R11 ), or -( L4 ) p4 -Si( R12 )( R13 )-( L5 ) p5 -Si( R9 )( R10 )( R11 ), and the remainder R3 to R5 are substituted or unsubstituted C1 to C20 alkoxy groups, halogen atoms, or hydroxyl groups. R11 to R13 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, a hydroxyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, provided that R3 to R5 are all -( L4 ) p4 -Si( R9 )( R10 )( R11 ), or -( L4 ) p4 -Si( R12 )( R13 )-( L5 ) p5 -Si( R9 )( R10 )( R11 ), at least one of R11 to R13 is a substituted or unsubstituted C1 to C20 alkoxy group, a halogen atom, or a hydroxyl group. L 4 and L 5 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 oxyalkylene group, or a combination thereof, and p4 and p5 are each independently integers from 1 to 10. In the definition of Rf, the fluorine-containing (poly)ether group represents a fluorine-containing ether group or a fluorine-containing polyether group. According to another aspect, a composition containing a silane compound having the fluorine-containing (poly)ether group described above is provided. A composition containing a fluorine-containing silane compound is used as a surface coating material. When a surface coating film is formed on the upper surface of a display using such a composition, wear occurs over time, resulting in reduced durability. Accordingly, in order to solve the aforementioned problems, the inventors have completed an invention that improves wear resistance and durability by increasing the bonding between silane compounds containing fluorine-containing (poly)ether groups while maintaining high slip properties, using a composition containing a silane compound containing a fluorine-containing (poly)ether group of Formula 1. Compared to conventional fluorine-containing silane compounds, the fluorine-containing (poly)ether group-con