Fluorine-containing urethane (meth)acrylate, curable composition, and antireflective film

Patent metadata

Field	Value
Publication number	US-10000657-B2
Application number	US-201414913672-A
Country	US
Kind code	B2
Filing date	Aug 19, 2014
Priority date	Aug 23, 2013
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

It is an object of the present invention to provide a urethane (meth)acrylate that enables formation of a cured layer having a low reflectance and excellent excoriation resistance, a curable composition produced by using the same, and an antireflective film. In particular, there is provided a fluorine-containing urethane (meth)acrylate represented by General Formula (I) and having a fluorine atom content ranging from 25 to 60 mass % (where R 1 and R 2 each represent a specific fluorinated alkyl group, R 3 and R 4 each represent a hydrogen atom or a methyl group, A represents a trivalent linking group represented by any of Structural Formulae (A1) to (A4), and X and Y each independently represent a divalent linking group represented by any of Structural Formulae (a) to (c)) [in Structural Formula (c), R5 represents an alkyl group having 1 to 6 carbon atoms].

First claim

The invention claimed is:

1. A fluorine-containing urethane (meth)acrylate represented by General Formula (I) and having a fluorine atom content ranging from 25 to 60 mass %

where R 1 and R 2 each independently represent a fluorinated alkyl group in which the number of carbon atoms to which fluorine atoms are directly bonded is from 2 to 6 or a fluorinated alkyl group which has a bond via an oxygen atom and in which the number of carbon atoms to which fluorine atoms are directly bonded is from 2 to 6 in total; R 3 and R 4 each represent a hydrogen atom or a methyl group; A represents a trivalent linking group represented by any of Structural Formulae (A1) to (A4); and X and Y each independently represent a divalent linking group represented by any of Structural Formulae (a) to (c)

in Structural Formula (c), R5 represents an alkyl group having 1 to 6 carbon atoms.

2. The fluorine-containing urethane (meth)acrylate according to claim 1 , wherein the fluorine atom content is from 35 to 60 mass %.

3. The fluorine-containing urethane (meth)acrylate according to claim 1 , wherein R 1 and R 2 are each a C n F 21 CH 2 group and n is an integer from 2 to 6, a C n F2 n+1 CH 2 CH 2 group and n is an integer from 2 to 6, or a C 3 F 7 OCF(CF 3 )CH 2 group.

4. The fluorine-containing urethane (meth)acrylate according to claim 1 , wherein R 1 and R 2 are each a C 6 F 13 CH 2 CH 2 group or a C 4 F 9 CH 2 CH 2 group, R 3 and R 4 are each a hydrogen atom, A is a linking group represented by Structural Formula (A2), and X and Y are each a linking group represented by Structural Formula (a).

5. A curable composition comprising the fluorine-containing urethane (meth)acrylate (I) according to claim 1 .

6. The curable composition according to claim 5 , further comprising a low-refractive-index agent (II).

7. The curable composition according to claim 6 , wherein the low-refractive-index agent (II) is fine hollow silica particles.

8. An antireflective film comprising a cured coating film of the curable composition according to claim 5 .

9. The antireflective film according to claim 8 , wherein the thickness of the cured coating film is from 50 to 300 nm.

Assignees

• Dainippon Ink & Chemicals

Inventors

• Suzuki Hideya

Classifications

• C09D133/16

  Homopolymers or copolymers of esters containing halogen atoms · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08F8/18

  Introducing halogen atoms or halogen-containing groups · CPC title

• C08F222/1065

  of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates · CPC title

• G02B1/111

  using layers comprising organic materials · CPC title