KR102204845B1 - Fluoropolyether modifided amine compounds, curable composition containing the same, and cured product thereof - Google Patents

Abstract

The present invention relates to a fluoropolyether-modified amine compound, a curable composition including the same and a cured product thereof. According to the present invention, the fluoropolyether-modified amine compound can realize low surface energy and a high oil contact angle upon the photocuring, and can provide a smooth touch feeling, when being applied to the surface of a touch panel display, or the like. In addition, the fluoropolyether-modified amine compound is capable of rapid curing with high sensitivity. Therefore, the fluoropolyether-modified amine compound allows inhibition of fingerprint staining or contaminant attachment and easy removal, when being applied to the surfaces of various flat panel displays, including touch panel displays, requiring high visibility, and can be used widely in various industrial fields to prevent damages and to impart a good touch feeling.

Description

Fluoropolyether modifided amine compounds, curable composition containing the same, and cured product thereof

The present invention relates to a fluoropolyether-modified amine compound, a curable composition comprising the same, and a cured product thereof.

As the use of the touch panel display is expanded in recent years, the operation method of the touch panel display, in addition to the conventional operation simply called a tap of touching a finger to a point of the panel, a flick operation to flip, a drag operation to drag, a pinch to pinch operation, etc. It has been extended to manipulations that have a great significance for the dynamic contact between the and screen. Accordingly, for the coating of a touch panel display, in addition to the conventional water repellency, oil repellency, anti-fingerprint properties, and fingerprint wiping properties, the touch when the finger is slipped has become very important. In addition, the coating of the touch panel display is difficult to attach fingerprint marks, and even if the fingerprint marks are attached, it should be easy to remove them.

In the case of a coating composition containing an acrylic compound having a fluoropolyether group, since the fluoropolyether structure is fixed on the surface of the coating layer by the reaction of the acrylic group, there is a limit to the smooth texture and improvement thereof when the finger is slipped. There was.

On the other hand, as a method of obtaining a better tactile feel in addition to the excellent antifouling performance described above, it was considered to dispose a fluoropolyether compound having no polymerizable group on the outermost surface of the coating layer. As the simplest method, a method of coating a non-functional fluoropolyether compound once on a substrate is mentioned. However, in an example in which such a non-functional fluoropolyether compound is blended into the coating composition as it is, in the case of a low-molecular fluoropolyether compound soluble in a general non-fluorinated coating composition, a sufficient smooth feel is not obtained, and smooth In the case of a fluoropolyether compound that is long enough to obtain a texture, it does not dissolve in the coating composition or is very poor in compatibility, and thus precipitation or turbidity occurs, and thus there is a problem that it cannot be uniformly coated. For this reason, in addition to the above-described antifouling performance, the development of a cured product that realizes a smooth touch, and a coating composition for realizing the same is a situation that is continuously required.

JP 4709271 B2 JP 4709272 B2 JP 4873666 B2

An object of the present invention is to provide a novel fluoropolyether-modified amine compound for forming a hard coat layer capable of satisfying excellent antifouling properties while implementing a smooth touch.

The present invention is a fluoropolyether-modified amine compound that is designed to introduce an amine group at one end or a linking group of a fluoropolymer containing a fluoropolyether group, induces a stable curing reaction and prevents deterioration of properties of the coating surface even after curing And a surface treatment agent comprising the same.

An object of the present invention is to provide a cured product and a curable composition for the same, which realizes excellent hardness and numerical stability through a rapid and stable curing reaction, and satisfies excellent antifouling properties required by a hard coat layer of a flat panel display.

In order to achieve the above object, the present invention provides a fluoropolyether-modified amine compound represented by the following Formula 1 or Formula 2.

[Formula 1]

[Formula 2]

[In Formulas 1 and 2,

Rf1 to Rf3 are monovalent fluoropolyether groups;

X ₁ to X ₃ are each independently a divalent substituent selected from an amide bond, an ether bond, a thioether bond, an ester bond, a carbamate bond and a ketone bond;

Y ₁ is C ₁ -C ₂₀ alkylene, and in the alkylene at least one non-adjacent -CH ₂ -is -O-, -S-, -C(=O)-, -NR-, or May be replaced by a combination, wherein R is hydrogen or C _1-7 alkyl;

Y ₂ and Y ₃ are different C ₁ -C ₂₀ alkylenes;

R ₁ to R ₂ are each independently hydrogen or C ₁ -C ₂₀ alkyl;

a is an integer selected from 1 to 10;

b is an integer selected from 0 to 10, and when a or b is an integer of 2 or more, the substituents of each repeating unit may be the same or different from each other.]

In the fluoropolyether-modified amine compound according to an embodiment of the present invention, Rf1 to Rf3 in Formula 1 or Formula 2 may be a fluoropolyether group represented by Formula 3, independently of each other.

[Chemical Formula 3]

Rf11-O-[Rf12-O] _m -[Rf13-O] _n -[CF ₂ ] _o -*

[In Chemical Formula 3,

Rf11 is fluorosubstituted C ₁ -C ₄ alkyl;

Rf12 And Rf13 is different from each other fluorosubstituted C ₁ -C ₄ alkylene;

m and o are each independently an integer selected from an integer of 0 to 10;

n is an integer selected from an integer of 1 to 10.]

In the fluoropolyether-modified amine compound according to an embodiment of the present invention, Y ₁ in Formula ₁ is C ₆ -C ₂₀ alkylene, and in the alkylene, at least one non-adjacent -CH ₂ -is -O-, -S-, -C(=O)-, -NR-, or a combination thereof, wherein R is hydrogen; Y ₂ and Y ₃ in Formula 2 may be C ₁ -C ₄ alkylene independently of each other.

The fluoropolyether-modified amine compound according to an embodiment of the present invention may be represented by Formula 4 below.

[Formula 4]

[In Chemical Formula 4,

Rf1 is a monovalent fluoropolyether group;

Y ₁ is C ₆ -C ₂₀ alkylene, and in the alkylene, at least one non-adjacent -CH ₂ -is -O-, -S-, -C(=O)-, -NR-, or May be replaced by a combination, wherein R is hydrogen.]

The fluoropolyether-modified amine compound according to an embodiment of the present invention may be represented by Formula 5 below.

[Chemical Formula 5]

[In Chemical Formula 5,

Rf2 and Rf3 are each independently a monovalent fluoropolyether group;

Y ₂ and Y ₃ are C ₁ -C ₄ alkylenes different from each other;

a is an integer selected from 1 to 8;

b is an integer selected from 0 to 8.]

In the fluoropolyether-modified amine compound according to an embodiment of the present invention, Y ₁ in Formula ₁ is C ₆ -C ₂₀ alkylene, -(C ₁ -C ₃ alkylene)-[O-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-[OC(=O)-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene )-[OC(=O)-O-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-S-[(C ₁ -C ₃ alkylene)] _p- Or -(C ₁ -C ₃ alkylene)-[NH-(C ₁ -C ₃ alkylene)] _p -, and p may be an integer selected from 1 to 6 independently of each other.

In the fluoropolyether-modified amine compound according to an embodiment of the present invention, Rf1 to Rf3 in Formula 1 or Formula 2 may be a perfluoropolyether group.

In addition, in the present invention, a surface treatment agent containing a fluoropolyether-modified amine compound is provided.

In addition, the present invention provides a photopolymerization composition comprising a fluoropolyether-modified amine compound, a photopolymerizable compound, a photoinitiator, and a solvent.

In addition, in the present invention, a cured product of the above-described photopolymerization composition is provided.

In addition, the cured product according to an embodiment of the present invention may be an optical film for preventing contamination or preventing reflection of a flat panel display.

The fluoropolyether-modified amine compound according to the present invention not only realizes low surface energy and high oil contact angle during photocuring, but also provides a smooth touch by being applied to surfaces such as touch panel displays. In addition, rapid curing is possible with excellent sensitivity.

The fluoropolyether-modified amine compound according to the present invention has the advantage of improving the adhesion between the substrate and the photopolymerization composition, and stable adhesion to the substrate without decomposition as well as damage to the film quality is possible even after curing. It has the advantage of being able to preserve it. In addition, it has an improved solubility as well as good compatibility with conventional solvents. Accordingly, it does not cause precipitation or turbidity in the photopolymerization composition, so that uniform coating is possible and long-term storage stability is excellent.

Accordingly, according to the present invention, it is applied to the surface of various flat panel displays including touch panel displays that require high visibility, so that adhesion of fingerprint marks or contaminants can be inhibited and easily removed, and damage prevention as well as Excellent touch feeling can be given. Accordingly, it is expected that it can be usefully used as a material for a surface treatment agent or a curable coating composition.

The fluoropolyether-modified amine compound according to the present invention, the curable composition including the same, and the cured product thereof are described in detail below, but unless otherwise defined in the technical and scientific terms used, the technical field to which the present invention belongs is generally A description of known functions and configurations that may unnecessarily obscure the subject matter of the present invention in the following description will have the meaning commonly understood by those skilled in the art.

As used herein, the term "fluoropolyether group" refers to a monovalent substituent in which at least one or more of the hydrogen atoms included in the polyether group is replaced with fluoro (F).

In addition, the term "perfluoropolyether group" in the present specification means a monovalent substituent in which all of the hydrogen atoms included in the polyether group are replaced with fluoro (F).

In addition, as used herein, a substituent including an alkyl other than "alkyl" refers to a monovalent substituent derived from a straight-chain or branched hydrocarbon.

In addition, the term "alkylene" in the present specification means a divalent substituent induced by the removal of one hydrogen from the alkyl group.

In addition, the term "amide bond" in the present specification means *-(C=O)NR ^a -*, and R ^a may be hydrogen or C ₁ -C ₇ alkyl.

In addition, the term "ether bond" in this specification means *-O-*.

In addition, the term "thioether bond" in the present specification means *-S-*.

In addition, the term "ester bond" in this specification means *-(C=O)O-*.

In addition, the term "carbamate bond" in the present specification means *-O-(C=O)NR ^a -*, and R ^a may be hydrogen or C ₁ -C ₇ alkyl.

In addition, the term "ketone bond" in the present specification means *-(C=O)-*.

In addition, the term "average molecular weight" in the present specification may mean a number average molecular weight or a weight average molecular weight. Specifically, when fluoro, such as a fluoropolyether-modified amine compound, was included, the number average molecular weight was confirmed as a value measured by ¹⁹ F-NMR. In addition, the unit of the average molecular weight is g/mol.

In addition, in the present specification, the expression "comprising" is an open-type substrate having a meaning equivalent to an expression such as "have", "include", "have" or "feature", and is not listed further. It does not exclude elements, materials or processes that are not.

In addition, the singular form used in the present specification may be intended to include the plural form unless otherwise indicated in the context.

In addition, units used in the present specification are based on weight (g), and as an example, the unit of% or ratio means weight% or weight ratio.

As mentioned in the background art, although the conventional acrylic compound having a fluoropolyether group can provide excellent antifouling properties, there is a limit to the smooth texture and improvement thereof.

In the course of research to solve such a problem, the present inventors confirmed that the limitation thereof can be overcome by introducing an amine group to one end or a linking group of a fluorine polymer containing a fluoropolyether group. Further, the fluoropolyether-modified amine compound having such structural characteristics can easily form a thin film having a uniform and smooth surface through rapid curing and provide a cured product having excellent hardness and numerical stability. Accordingly, the present inventors propose the present invention to provide a novel fluoropolyether-modified amine compound molecularly designed as described above and a use for useful application to a hard coat layer of various flat panel displays by utilizing it as an additive material.

Hereinafter, the present invention will be described in detail.

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

[Formula 1]

[Formula 2]

[In Formulas 1 and 2,

Rf1 to Rf3 are monovalent fluoropolyether groups;

X ₁ to X ₃ are each independently a divalent substituent selected from an amide bond, an ether bond, a thioether bond, an ester bond, a carbamate bond and a ketone bond;

Y ₁ is C ₁ -C ₂₀ alkylene, and in the alkylene at least one non-adjacent -CH ₂ -is -O-, -S-, -C(=O)-, -NR-, or May be replaced by a combination, wherein R is hydrogen or C _1-7 alkyl;

Y ₂ and Y ₃ are different C ₁ -C ₂₀ alkylenes;

R ₁ to R ₂ are each independently hydrogen or C ₁ -C ₂₀ alkyl;

a is an integer selected from 1 to 10;

b is an integer selected from 0 to 10, and when a or b is an integer of 2 or more, the substituents of each repeating unit may be the same or different from each other.]

With this structural feature, the fluoropolyether-modified amine compound according to the present invention can provide a molded article having a uniform appearance with a smooth texture, that is, a coating layer. In addition, the molded article has excellent antifouling properties such as water repellency, oil repellency, anti-fingerprint property, and fingerprint wiping property. In addition, in the case of the above-described fluoropolyether-modified amine compound, it is stabilized through 1,4-addition reaction with acrylate monomers, etc., effectively suppressing damage to the film quality even after photocuring, and retaining its functions for a long time as described above. I can.

On the other hand, when amine groups are introduced at both ends of a fluoropolymer containing a fluoropolyether group, the fluorine polymer tends to be placed inside the surface rather than on the surface of the substrate, showing a disadvantage in the expression of the desired antifouling properties. The persistence was also remarkably low.

The fluoropolyether-modified amine compound according to the present invention has excellent solubility in a common solvent used in the photopolymerization composition, and does not lose transparency upon curing.

For example, the conventional solvent is an aromatic hydrocarbon-based solvent such as benzene, toluene, xylene, ethylbenzene, and tetralin; aliphatic or alicyclic hydrocarbon-based solvents such as n-hexane, n-heptane, mineral spirit, and cyclohexane; Halogen-based solvents such as methyl chloride, methyl bromide, methyl iodide, methylene dichloride, chloroform, carbon tetrachloride, trichloroethylene, perchloroethylene, and ortho dichlorobenzene; Ester or ester ether solvents such as ethyl acetate, butyl acetate, methoxy butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate; Ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl cellosolve, ethyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, di-n-butyl ketone, and cyclohexanone; Alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, 2-ethyl hexyl alcohol, benzyl alcohol, and ethylene glycol; Amide solvents such as N,N-dimethyl formamide and N,N-dimethyl acetamide; Sulfoxide solvents such as dimethyl sulfoxide; Or a heterocyclic compound-based solvent such as N-methyl-2-pyrrolidone; It may be selected from acetone, 　 methyl ethyl 　 ketone, methyl isobutyl ketone, di-n-butyl ketone, and cyclohexanone may be selected from a ketone solvent.

For example, the fluoropolyether-modified amine compound of the present invention may satisfy the first solubility (25°C, based on the total weight) of the ketone solvent described above of 1% by weight or more, specifically 5% by weight. Above, more specifically, it may be to satisfy the range of 5 to 30% by weight.

For example, the fluoropolyether-modified amine compound of the present invention satisfies the same level as the first solubility in the second solubility (0°C, based on the total weight) in the ketone-based solvent described above.

In the fluoropolyether-modified amine compound according to an embodiment of the present invention, Rf1 to Rf3 in Formula 1 or Formula 2 may be a fluoropolyether group represented by Formula 3, independently of each other.

[Chemical Formula 3]

Rf11-O-[Rf12-O] _m -[Rf13-O] _n -[CF ₂ ] _o -*

[In Chemical Formula 3,

Rf11 is fluorosubstituted C ₁ -C ₄ alkyl;

Rf12 And Rf13 is different from each other fluorosubstituted C ₁ -C ₄ alkylene;

m and o are each independently an integer selected from an integer of 0 to 10;

n is an integer selected from an integer of 1 to 10.]

For example, when Rf1 to Rf3 in Formula 1 or Formula 2 includes two repeating units, CF ₃ O-[CF ₂ O] _m -[CF ₂ CF ₂ O] _n -CF ₂ -, independently of each other, CF ₃ O-[CF ₂ O] _m -[CF ₂ CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ O-[CF ₂ CF ₂ O] _m -[CF ₂ CF ₂ CF ₂ O] _n- CF ₂ -, CF ₃ CF ₂ O-[CF ₂ O] _m -[CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ O] _m -[CF ₂ CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ CF ₂ O] _m -[CF ₂ CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ O-[CF ₂ CF ₂ CF ₂ O ] _m -[CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ O-[CF ₂ CF ₂ CF ₂ O] _m -[CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ CF ₂ CF ₂ O] _m -[CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ CF ₂ CF ₂ O] _m -[CF ₂ O] _n -CF ₂ -, And CF ₃ CF ₂ O-[CF ₂ CF ₂ O] _m -[CF ₂ O] _n -CF ₂ -. At this time, the definitions of m and n follow Formula 3. In addition, a case in which at least one or more fluoros contained in the repeating unit is replaced by hydrogen may also be an aspect of the present invention, and a case where all fluoro is replaced by hydrogen is excluded.

For example, when Rf1 to Rf3 of Formula 1 or Formula 2 contains one repeating unit, CF ₃ O-[CF ₂ O] _n -CF ₂ -, CF ₃ O-[CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ O-[CF ₂ CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ O-[CF(CF ₃ )CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ CF ₂ O] _n -CF ₂ -, CF ₃ CF ₂ O-[CF ₂ CF ₂ CF ₂ O] _n- It may be selected from CF ₂ -, and CF ₃ CF ₂ O-[CF(CF ₃ )CF ₂ O] _n -CF ₂ -. At this time, the definition of n follows the formula (3). In addition, a case in which at least one or more fluoros contained in the repeating unit is replaced with hydrogen may also be an aspect of the present invention, and a case in which all fluoros are replaced with hydrogen is excluded.

The fluoropolyether-modified amine compound according to the present invention has a high solubility in the above-described solvent, and in terms of realizing superior surface smoothness or fingerprint wipeability, Y ₁ in Formula ₁ is an alkyl having 6 or more carbon atoms. One or more non-adjacent -CH ₂ -in the alkylene containing ene or may have a linking group substituted by -O-, -S-, -C(=O)-, -NR-, or a combination thereof. have.

For example, Y ₁ in Formula 1 may be C ₆ -C ₂₀ alkylene.

For example, Y ₁ in Formula 1 is C ₆ -C ₂₀ alkylene, and in the alkylene at least one non-adjacent -CH ₂ -is -O-, -S-, -C(=O)- , -NR- or a combination thereof may be substituted, and R may be hydrogen.

For example, Y ₁ in Formula 1 is C ₆ -C ₁₅ alkylene, -(C ₁ -C ₇ alkylene)-[O-(C ₁ -C ₇ alkylene)] _p -, -(C _1- C ₇ alkylene)-[OC(=O)-(C ₁ -C ₇ alkylene)] _p -, -(C ₁ -C ₇ alkylene)-[OC(=O)-O-(C _1- C ₇ alkylene)] _p -, -(C ₁ -C ₇ alkylene)-S-[(C ₁ -C ₇ alkylene)] _p -or -(C ₁ -C ₇ alkylene)-[NH- (C ₁ -C ₇ alkylene)] _p -, and p may be an integer selected from 1 to 6 independently of each other.

For example, Y ₁ in Formula 1 is C ₆ -C ₁₅ alkylene, -(C ₁ -C ₃ alkylene)-[O-(C ₁ -C ₃ alkylene)] _p -, -(C _1- C ₃ alkylene)-[OC(=O)-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-[OC(=O)-O-(C _1- C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-S-[(C ₁ -C ₃ alkylene)] _p -or -(C ₁ -C ₃ alkylene)-[NH- (C ₁ -C ₃ alkylene)] _p -, and p may be an integer selected from 1 to 6 independently of each other.

For example, Y ₂ and Y ₃ in Formula 2 may be C ₁ -C ₄ alkylene independently of each other.

For example, X ₁ to X ₃ in Formula 1 or Formula 2 may be divalent substituents independently selected from an amide bond and an ester bond.

In addition, the fluoropolyether-modified amine compound according to the present invention has the above-described linking group, thereby enhancing adhesion to the substrate and implementing a smooth touch. In addition, it is possible to form a cured product having a surface excellent in antifouling properties such as water repellency, oil repellency, anti-fingerprint property, fingerprint wiping property, and the like by rapid curing. In other words, by performing a function of protecting the adhesive surface with the substrate from external environments such as mechanical friction and chemical contact such as moisture, it is possible to implement a more stable adhesive force and to impart improved hardness.

Specifically, the fluoropolyether-modified amine compound according to an embodiment of the present invention may be represented by the following Chemical Formula 4 or Chemical Formula 5.

[Formula 4]

[In Chemical Formula 4,

Rf1 is a monovalent fluoropolyether group;

Y ₁ is C ₆ -C ₁₅ alkylene, and in the alkylene at least one non-adjacent -CH ₂ -is -O-, -S-, -C(=O)-, -NR-, or May be replaced by a combination, wherein R is hydrogen.]

[Chemical Formula 5]

[In Chemical Formula 5,

Rf2 and Rf3 are each independently a monovalent fluoropolyether group;

Y ₂ and Y ₃ are C ₁ -C ₄ alkylenes different from each other;

a is an integer selected from 1 to 8;

b is an integer selected from 0 to 8.]

For example, Y ₁ in Formula 4 is C ₆ -C ₇ alkylene, or -(C ₁ -C ₃ alkylene)-[O-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-[OC(=O)-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-[OC(=O)-O-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-S-[(C ₁ -C ₃ alkylene)] _p -or -(C ₁ -C ₃ alkylene)-[NH -(C ₁ -C ₃ alkylene)] _p -, and p may be an integer selected from 1 to 4 independently of each other.

For example, in Formula 5, Y ₂ and Y ₃ may be different C ₂ -C ₃ alkylenes.

In the fluoropolyether-modified amine compound according to an embodiment of the present invention, in terms of stably maintaining excellent antifouling properties for a long period of time, Rf1 to Rf3 in Formula 1 or Formula 2 may be perfluoropolyether groups. I can.

In addition, the fluoropolyether-modified amine compound according to the present invention may have an average molecular weight of 2,000 to 500,000.

Hereinafter, the use of the fluoropolyether-modified amine compound of the present invention will be described.

The use of one aspect of the present invention may be use as a surface treatment agent.

In addition, the use of another aspect of the present invention may be use as an additive in a photopolymerization composition. The fluoropolyether-modified amine compound according to the present invention serves as a surface treatment agent and a surface modifier in the photopolymerization composition. That is, the fluoropolyether-modified amine compound according to the present invention is used in various compositions, and according to the purpose, it is possible to provide excellent surface characteristics of smooth touch as well as antifouling properties such as water repellency, oil repellency, fingerprint resistance, fingerprint wipeability, etc. have. In addition, by appropriately controlling mechanical strength, refractive index, optical properties, etc., the surface properties of the substrate can be easily modified.

Specifically, the photopolymerization composition according to the present invention may include the above-described fluoropolyether-modified amine compound of the present invention, a photopolymerizable compound, a photoinitiator, and a solvent.

In the photopolymerization composition according to an embodiment of the present invention, the photopolymerizable compound may be used without limitation, such as a monofunctional polymerizable compound, a polyfunctional polymerizable compound, and one or two selected from polymerizable compounds described below. It is that it can be used in the form of the above mixture.

For example, the photopolymerizable compound may be an acrylate-based monomer, and non-limiting examples thereof include methyl (meth) acrylate, allyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, isodecyl (Meth)acrylate, 2-dodecylthioethyl (meth)acrylate, octyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth) )Acrylate, hydroxybutyl (meth)acrylate, isooctyl (meth)acrylate, isodexyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, tetrafurfuryl ( Monofunctional monomers such as meth)acrylate, phenoxyethyl (meth)acrylate, urethane (meth)acrylate, aminoethyl (meth)acrylate, and dimethylaminoethyl (meth)acrylate; 1,3-butanedioldi(meth)acrylate, 1,4-butanedioldi(meth)acrylate, 1,6-hexanedioldi(meth)acrylate, ethylene glycol di(meth)acrylate, bisphenol A-ethylene Glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (Meth)acrylate, neopentyl glycol di (meth) acrylate, dicyclopentanyl di (meth) acrylate, caprolactone-modified dicyclopentenyl di (meth) acrylate, ethylene oxide modified phosphate di (meth) acrylate, Bis(2-hydroxyethyl)isocyanurate di(meth)acrylate, di(acryloxyethyl)isocyanurate, allylated cyclohexyldi(meth)acrylate, dimethyloldicyclopentane diacrylate, ethylene Bifunctional monomers such as oxide-modified hexahydrophthalic acid diacrylate, tricyclodecanedimethanol acrylate, neopentyl glycol-modified trimethylolpropane diacrylate, and adamantane diacrylate; Trimethylolpropane tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, propionic acid-modified dipentaerythritol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, propylene oxide modified trimethylolpropane Trifunctionality such as tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, tris(acryloxyethyl)isocyanurate, and glycerol tri(meth)acrylate Monomer; Tetrafunctional monomers such as diglycerin tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, and ditrimethylolpropane tetra(meth)acrylate; 5-functional monomers, such as dipentaerythritol penta (meth)acrylate; And 6-functional monomers such as dipentaerythritol hexa(meth)acrylate, and the like, and it is more preferable to use a polyfunctional monomer in terms of more improved surface properties and excellent hardness.

For example, the photopolymerizable compound may be an epoxy-based monomer, and a non-limiting example thereof is an epoxy compound having three or more epoxy groups, a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a bisphenol S type epoxy compound, It may be one selected from a dicyclopentadiene type epoxy compound, an alicyclic epoxy compound, and a brominated epoxy compound.

As an example, the photopolymerizable compound may be an acrylic copolymer in which a (meth)acrylate monomer having an alkyl group having 1-12 carbon atoms and a polymerizable monomer having a crosslinkable functional group are copolymerized.

In the photopolymerization composition according to an embodiment of the present invention, the photoinitiator may be used without limitation as long as it is a known one, and as an example, a cationic photoinitiator that creates a cationic species or a Lewis acid, a photoinitiator that creates a radical, or a combination thereof Can be used.

For example, the photoinitiator may be selected from a benzoin derivative, acetophenone derivative, anthraquinone derivative, thioxanthone derivative, ketal derivative, benzophenone derivative, α-aminoacetophenone derivative, acylphosphine oxide derivative, and oxime ester derivative I can. Non-limiting examples thereof include benzoin derivatives such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Acetophenone derivatives such as acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, and 4-(1-t-butyldioxy-1-methylethyl)acetophenone; Anthraquinone derivatives such as 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, and 1-chloroanthraquinone; Thioxanthone derivatives such as 2,4-dimethyl thioxanthone, 2,4-diisopropyl thioxanthone, and 2-chloro thioxanthone; Ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; Benzophenones, such as benzophenone, 4-(1-t-butyldioxy-1-methylethyl)benzophenone, and 3,3',4,4'-tetrakis(t-butyldioxycarbonyl)benzophenone derivative; 2-Methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanone-1,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one , 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, and N,N-dimethylaminoacetophenone (commercial product Examples include α-aminoacetophenone derivatives such as Irugacure (registered trademark) 907, Irugacure 369, Irugacure 379, etc. manufactured by Chiba Specialty Chemicals (currently, Chiba Japan); 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (as a commercial product, BASF Acylphosphine oxide 　 derivatives such as Lucilin (registered trademark) TPO, manufactured by Chiba Specialty Chemicals, Irugacure 819, etc.); 2-(acetyloxyiminomethyl)thioxanthene-9-one, (1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2-(O-benzoyloxime)), (ethanone , 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, and 1-(O-acetyloxime)) may be selected from oxime ester derivatives.

In addition, the photoinitiator may be selected from onium salt derivatives, and the like, and a non-limiting example thereof is selected from diaryliodonium salt, triarylsulfonium salt, triaryl selenonium salt, tetraarylphosphonium salt, aryl diazonium salt, etc. It can be.

In the photopolymerization composition according to an embodiment of the present invention, the solvent is an aromatic hydrocarbon-based solvent such as benzene, toluene, xylene, ethylbenzene, and tetralin; aliphatic or alicyclic hydrocarbon-based solvents such as n-hexane, n-heptane, mineral spirit, and cyclohexane; Halogen-based solvents such as methyl chloride, methyl bromide, methyl iodide, methylene dichloride, chloroform, carbon tetrachloride, trichloroethylene, perchloroethylene, and ortho dichlorobenzene; Ester or ester ether solvents such as ethyl acetate, butyl acetate, methoxy butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate; Ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl cellosolve, ethyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, di-n-butyl ketone, and cyclohexanone; Alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, 2-ethyl hexyl alcohol, benzyl alcohol, and ethylene glycol; Amide solvents such as N,N-dimethyl formamide and N,N-dimethyl acetamide; Sulfoxide solvents such as dimethyl sulfoxide; And heterocyclic compound solvents such as N-methyl-2-pyrrolidone; It is that it can be used in the form of one or a mixture of two or more selected from and the like.

The curable composition according to an embodiment of the present invention includes 0.01 to 10% by weight of the fluoropolyether-modified amine compound of the present invention, 5 to 60% by weight of the photopolymerizable compound, 0.01 to 3% by weight of the photoinitiator and the balance based on the total weight. It may contain a solvent of. Specifically, the curable composition may include 0.1 to 5% by weight of a fluoropolyether-modified amine compound of the present invention, 15 to 60% by weight of a photopolymerizable compound, 0.1 to 2% by weight of a photoinitiator, and a residual amount of a solvent, and more Specifically, it may include 0.1 to 3% by weight of the fluoropolyether-modified amine compound of the present invention, 25 to 50% by weight of the photopolymerizable compound, 0.5 to 2% by weight of the photoinitiator, and the balance of the solvent.

In addition, the curable composition according to an embodiment of the present invention further contains additives such as inorganic binders, brighteners, wettability improving agents, pigments, deodorants, antifoaming agents, antioxidants, organic flame retardants, thickeners, plasticizers, etc., within the range not losing intrinsic properties. Of course, it can contain. In this case, the additives may be included independently of each other in an amount of 0.01 to 5 weight based on the total weight.

In addition, the present invention provides a cured product obtained from the above-described curable composition.

Specifically, the cured product according to the present invention is obtained by photocuring the curable composition, and may further perform a process such as drying or washing by heat treatment before and after the application of the curable composition.

For example, the cured product according to the present invention may be prepared in the form of a film by applying the above-described curable composition of the present invention on a substrate to form a coating layer, and then photocuring.

In this case, the photocuring may be performed through absorption of light energy such as electron beam, visible light, or ultraviolet energy.

For example, in the case of photocuring performed through the ultraviolet energy, a UV light source such as a UV-A region (320 to 400 nm), a UV-B region (280 to 320 nm), or a UV-C region (200 to 280 nm) Using a high-pressure mercury lamp, the exposure process can be performed for 1 to 5 minutes.

In this way, the cured product according to an embodiment of the present invention may be prepared in the form of a film as mentioned above. The film is provided on the surface of a touch panel display such as a variety of flat panel displays, so that the surface can be characterized with various types of physical properties.

For example, the film may be an optical film for improving surface characteristics of a flat panel display, that is, improving surface feel.

For example, the film may be an optical film for preventing contamination or anti-reflection of a flat panel display, but is not limited thereto.

For example, the film may include a cover glass for a display, a tempered glass, or a glass for a transporter; Alternatively, it may be provided on the surface of an optical member, sanitary product, glass tableware, or building material, but is not limited thereto.

As an example, it goes without saying that the film may be provided in various thicknesses depending on the purpose.

For example, the film according to the present invention has excellent surface smoothness and at the same time has excellent antifouling properties such as water repellency, oil repellency, anti-fingerprint and fingerprint wipeability.

For example, the film according to the present invention may have a water contact angle of 100 degrees or more, specifically 105 degrees or more, and more specifically 105 to 120 degrees.

For example, the film according to the present invention satisfies a rate of change of less than 5% even when measuring the water contact angle after 72 hours in an atmosphere in which a 5% NaCl aqueous solution is continuously sprayed in a salt sprayer maintained at 30°C. Specifically, the rate of change may be within 3%, more specifically within 1%.

Hereinafter, the present invention will be described in more detail through examples.

Prior to this, terms or words used in the specification and claims should not be construed as being limited to their usual or dictionary meanings, and the inventors appropriately explain the concept of terms in order to explain their own invention in the best way. Based on the principle that it can be defined, it should be interpreted as a meaning and concept consistent with the technical idea of the present invention.

Therefore, the configuration shown in the embodiments described in the present specification is only the most preferred embodiment of the present invention, and does not represent all the technical spirit of the present invention, at the time of the present application, these are various equivalents that can be replaced. It should be understood that there are water and variations.

(Assessment Methods)

1. Pencil hardness

Pencil hardness was measured under a load of 500g using a pencil hardness tester (hardness tester, manufacturer: Chungbuk Tech). According to ASTM 3363-74, a standard pencil (Mitshbishi) was changed to 6B to 9H while maintaining a 45° angle, and a scratch was applied to the surface of the cured product obtained in the following Examples and Comparative Examples to observe the change of the surface. Thereafter, each experimental value was measured 5 times and evaluated as an average value.

2. Water contact angle

When distilled water was placed in a size of 3 µl on the surface of the cured product obtained in the following Examples and Comparative Examples (SEO), the angle between the surface and the water droplets was measured. The numerical value measured by this method was evaluated as a water contact angle value.

In addition, using the same cured product, the water contact angle was re-measured after 72 hours in an atmosphere in which a 5% NaCl aqueous solution was continuously sprayed in a salt sprayer maintained at 30°C.

3. Erase characteristics

Using a Kimwipes®, kimberly-clark, a line by an oil pen (name pen, manufacturer Monami) attached to the surface of the cured product obtained in the following Examples and Comparative Examples was wiped with a small force, and its erasing characteristics were visually evaluated. I did. The criteria are as follows.

○: The handwriting can be completely wiped.

△: The handwriting remains blurred.

×: The handwriting cannot be polished.

4. Appearance

The surface of the cured product obtained in the following Examples and Comparative Examples was subjected to sensory evaluation. Specifically, five ordinary people were subjected to sensory evaluation of the degree of smoothness on a 5-point scale by touching the surface of each cured product with their fingers (lowest: 1 point, highest: 5 points).

(Example 1)

Step 1) 63.9 g of 1,6-diaminohexane was dissolved in 200 ml of 1,4-dioxane, stirred at room temperature (25° C.), and a solution of 20 g of diet butyl dicarbonate dissolved in 200 ml of 1,4-dioxane was slowly added. Then, the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solvent was removed and 300 ml of distilled water was added to remove insoluble by-products by filtration, and the aqueous layer was extracted twice with 200 ml of dimethyl chloride. The extracted organic layer was washed twice with water, residual starting material was removed and concentrated, and 18.5 g (93.3%) of (6-amino-hexyl)-carbamic acid tert-butyl ester was obtained.

¹ H-NMR: 4.7(bs, 1H), 3.15(q, 2H), 2.7(t, 2H), 1.3-1.6(m, 13H), 1.2(s,2H)

Step 2) 10 g of a perfluoropolyether compound (average molecular weight 2,000 with a methyl ester group at one end) was dissolved in 10 g of trifluorotoluene and 10 g of perfluoroethyl ether, and 2 g of (6-amino-hexyl)-carbamic acid tert -After the butyl ester was added, the mixture was stirred at 40 degrees for 6 hours. After completion of the reaction, the solvent was removed, and after washing with methanol, a gelled reaction intermediate was obtained. The reaction intermediate was dissolved in perfluoroethyl ether, and trifluoroacetic acid was added to remove the Boc group. Thereafter, the reaction mixture was washed with a triethylamine methanol solution to obtain 9.8 g of a transparent liquid compound A-1 (yield = 94%, average molecular weight: 2050, Pd: 2.1).

¹ H-NMR: 3.61(t, 2H), 2.7(m, 2H), 1.3-1.6(m, 4H), 1.2(s,2H)

(Example 2)

In Example 1, a perfluoropolyether compound (average molecular weight of 3,500 having a methyl ester group at one end) was used instead of a perfluoropolyether compound (average molecular weight of 2,000 with a methyl ester group at one end), and liquid compound A-2 Was obtained (yield = 92%, average molecular weight: 3600, Pd: 2.2).

¹ H-NMR: 3.62(t, 2H), 2.7(m, 2H), 1.3-1.6(m, 4H), 1.2(s,2H)

(Example 3)

Step 1) 60.6 g of 4,7,10-trioxy-1,13-tridecanediamine was dissolved in 200 ml of 1,4-dioxane, stirred at room temperature, and 10 g of ditert butyl dicarbonate was dissolved in 200 ml of 1,4-dioxane. After the solution was slowly added, the mixture was stirred at room temperature for 24 hours. After the reaction was completed, the solvent was removed, 300 ml of distilled water was added to remove insoluble by-products by filtration, and the aqueous layer was extracted twice with 200 ml of dimethyl chloride. The extracted organic layer was washed twice with water to remove residual starting material and concentrated, (3-2-[2-(3-amino-propoxy)-ethoxy]-ethoxy-propyl)-carbamic acid tert-butyl ester , 12.5g (85%) was obtained.

¹ H-NMR: 8.0(bs, 1H), 3.52(t, 8H), 3.3(m, 4H), 2.98(t, 2H), 2.66(m, 2H) 1.4-1.8(m, 13H)

Step 2) 10 g of perfluoropolyether (average molecular weight 2,000 with a methyl ester group at one end) was dissolved in 10 g of trifluorotoluene and 10 g of perfluoroethyl ether, and 3.2 g of (3-2-[2-(3-amino) was dissolved. -Propoxy)-ethoxy]-ethoxy-propyl)-carbamic acid tert-butyl ester was added, followed by stirring at 40 degrees for 6 hours. After completion of the reaction, the solvent was removed, and after washing with methanol, a gelled reaction intermediate was obtained. The reaction intermediate was dissolved in perfluoroethyl ether, and trifluoroacetic acid was added to remove the Boc group. The reaction mixture was washed with a triethylamine methanol solution to obtain 10.2 g of a transparent liquid compound B-1 (yield = 93%, average molecular weight: 2200, Pd: 2.0).

¹ H-NMR: 3.61(t, 2H), 3.52(t, 8H), 3.3 (m, 4H), 2.66(m, 2H) 1.6-1.8(m, 4H)

(Example 4)

In Example 3, using perfluoropolyether (average molecular weight of 3,500 having a methyl ester group at one end) instead of perfluoropolyether (average molecular weight of 2,000 with a methyl ester group at one end), 10 g of liquid compound B-2 It was obtained (yield = 95%, average molecular weight: 3700, Pd: 2.3).

¹ H-NMR: 3.63(t, 2H), 3.52(t, 8H), 3.3 (m, 4H), 2.66(m, 2H) 1.6-1.8(m, 4H)

(Example 5)

Step 1) 63.94 g of pentaethylenehexamine was dissolved in 100 ml of 1,4-dioxane, stirred at room temperature, and a solution in which 10 g of ditert butyl dicarbonate was dissolved in 100 ml of 1,4-dioxane was slowly added, followed by stirring at room temperature for 24 hours. . After completion of the reaction, the solvent was removed and 300 ml of distilled water was added to remove insoluble by-products by filtration, and the aqueous layer was extracted twice with 200 ml of dimethyl chloride. The extracted organic layer was washed twice with water to remove residual starting material and concentrated, [2-(2-{2-[2-(2-amino-ethylamino)-ethylamino]-ethylamino}-ethylamino)- Ethyl]-carbamic acid tert-butyl ester, 11.7 g (77%) was obtained.

¹ H-NMR: 3.1(t, 2H), 2.5-2.9(m, 18H), 1.4(s, 9H)

Step 2) Dissolve 10 g of perfluoropolyether (average molecular weight 2,000 with a methyl ester group at one end) in 10 g of trifluorotoluene and 10 g of perfluoroethyl ether, and 3.33 g [2-(2-{2-[2-( 2-Amino-ethylamino)-ethylamino]-ethylamino}-ethylamino)-ethyl]-carbamic acid tert-butyl ester was added, followed by stirring at 40°C for 6 hours. After completion of the reaction, the solvent was removed, and after washing with methanol, a gelled reaction intermediate was obtained. The reaction intermediate was dissolved in perfluoroethyl ether, and trifluoroacetic acid was added to remove the Boc group. The reaction mixture was washed with a triethylamine methanol solution to obtain 10.5 g of a transparent liquid compound C-1 (yield = 95%, average molecular weight: 2200, Pd: 2.1).

¹ H-NMR: 3.62(t, 2H), 2.5-2.9(m, 18H)

(Example 6)

In Example 5, 10.2 g of C-2 was obtained by using perfluoropolyether (average molecular weight 3,500 having a methyl ester group at one end) instead of perfluoropolyether (average molecular weight 3,500 having a methyl ester group at one end). I did. (Yield = 97%, average molecular weight: 3700, Pd: 2.4).

¹ H-NMR:: 3.63(t, 2H), 2.5-2.9(m, 18H)

(Production Example 1)

After dissolving 50 g of perfluorohexylethyl methacrylate, 50 g of isobornyl methacrylate, and 5 g of azobisisobutyronitrile (　AIBN) in 400 g of methyl ethyl ketone, the reactor temperature was raised to 80 degrees and stirred for 12 hours. A compound of the structure was obtained (average molecular weight: 12000 Pd:2.3).

(Examples 7 to 12 and Comparative Example 1)

A curable composition was prepared to include the components shown in Table 1 below, and photocured to prepare a cured product.

Specifically, after dissolving a photopolymerizable compound and a photoinitiator in a solvent, each of the Examples (fluoropolyether-modified amine compound) or the compound of Preparation Example was added and stirred for 24 hours to prepare a curable composition. Each curable composition was bar-coated on the PET film after removing this material with a 0.4um syringe filter, and the solvent was removed in an oven at 80°C for 30 minutes. The coated film from which the solvent was removed was exposed to light for 2 minutes using a high pressure mercury lamp (LZ-U101) to obtain a cured product.

Through the evaluation method, the surface characteristics of each cured product were confirmed, and the results are shown in Table 2 below.

As shown in Table 2, the cured product obtained from the curable composition containing the fluoropolyether-modified amine compound according to the present invention was very excellent in appearance characteristics in which the degree of smoothness was scaled by 5 points.

In addition, it was confirmed that the cured product according to the present invention has very excellent erasing properties against surface contaminants by an oil pen. In general, the source of surface contamination caused by oil pens, etc., requires wipe resistance because it must be wiped with a tissue or wet tissue containing an organic solvent such as ethanol or acetone. Accordingly, the cured product according to the present invention can provide both wipe resistance against the use of an organic solvent as well as an antifouling property capable of removing surface contaminants caused by oil pens without using an organic solvent, and at the same time providing surface smoothness. It has an advantage over the prior art. On the other hand, in the case of Comparative Example 1, a fluorine substituent may be introduced on the surface of the substrate, but it did not provide any advantage in erasing characteristics. In addition, when amine groups were introduced at both ends of the fluorine polymer, the erasing characteristics were significantly lower than those of the examples according to the present invention.

In addition, the cured product according to the present invention achieves an excellent water contact angle and maintains it stably. On the other hand, in the case of the comparative example, it was excellent only at the initial water contact angle.

In addition, as the cured product according to the present invention is rapidly photocured with high sensitivity, a smooth appearance can be realized. In other words, it has excellent numerical stability. Accordingly, it is stably attached to a large-area surface used in a flat panel display to provide a hard coat layer having excellent surface properties such as pollution prevention and reflection prevention. As mentioned above, the fluoropolyether-modified amine compound according to the present invention can implement a more improved sensitivity, realize superior surface characteristics compared to the compound of Preparation Example, and provide a transparent cured product that satisfies high pencil hardness. In addition, according to the present invention, it has an advantage in that the above-described effects can be implemented even with a small amount of use.

Although the embodiments of the present invention have been described in detail as described above, those of ordinary skill in the art to which the present invention pertains, without departing from the spirit and scope of the present invention as defined in the appended claims. The invention may be implemented by various modifications. Accordingly, changes to the embodiments of the present invention are also included within the scope of the present invention.

Claims (11)

Fluoropolyether-modified amine compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Rf1 is a monovalent fluoropolyether group;
X ₁ is a divalent substituent selected from an amide bond, an ether bond, a thioether bond, an ester bond, a carbamate bond and a ketone bond;
Y ₁ is -(C ₁ -C ₇ alkylene)-[O-(C ₁ -C ₇ alkylene)]p-, -(C ₁ -C ₇ alkylene)-[OC(=O)-(C ₁ -C ₇ alkylene)]p-, -(C ₁ -C ₇ alkylene)-[OC(=O)-O-(C ₁ -C ₇ alkylene)]p-, -(C ₁ -C ₇ alkylene)-S-[(C ₁ -C ₇ alkylene)]p- or -(C ₁ -C ₇ alkylene)-[NH-(C ₁ -C ₇ alkylene)]p-, wherein p is each independently an integer selected from 1 to 6;
R ₁ to R ₂ are each independently hydrogen or C ₁ -C ₂₀ alkyl. The method of claim 1,
Rf1 in Formula 1 is,
A fluoropolyether-modified amine compound, which is a fluoropolyether group represented by the following formula (3):
[Chemical Formula 3]
Rf11-O-[Rf12-O] _m -[Rf13-O] _n -[CF ₂ ] _o -*
In Chemical Formula 3,
Rf11 is fluorosubstituted C ₁ -C ₄ alkyl;
Rf12 And Rf13 is different from each other fluorosubstituted C ₁ -C ₄ alkylene;
m and o are each independently an integer selected from an integer of 0 to 10;
n is an integer selected from an integer of 1 to 10. delete The method of claim 1,
The fluoropolyether-modified amine compound,
The fluoropolyether-modified amine compound represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
Rf1 is a monovalent fluoropolyether group;
Y ₁ is -(C ₁ -C ₇ alkylene)-[O-(C ₁ -C ₇ alkylene)]p-, -(C ₁ -C ₇ alkylene)-[OC(=O)-(C ₁ -C ₇ alkylene)]p-, -(C ₁ -C ₇ alkylene)-[OC(=O)-O-(C ₁ -C ₇ alkylene)]p-, -(C ₁ -C ₇ alkylene)-S-[(C ₁ -C ₇ alkylene)]p- or -(C ₁ -C ₇ alkylene)-[NH-(C ₁ -C ₇ alkylene)]p-, wherein p is an integer selected from 1 to 6 independently of each other. delete The method of claim 1,
Y ₁ in Formula 1 is -(C ₁ -C ₃ alkylene)-[O-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-[OC(= O)-(C ₁ -C ₃ alkylene)] _p -, -(C ₁ -C ₃ alkylene)-[OC(=O)-O-(C ₁ -C ₃ alkylene)] _p -,- (C ₁ -C ₃ alkylene)-S-[(C ₁ -C ₃ alkylene)] _p -or -(C ₁ -C ₃ alkylene)-[NH-(C ₁ -C ₃ alkylene)] _p -, wherein p is an integer selected from 1 to 6 independently of each other, a fluoropolyether-modified amine compound. The method of claim 1,
Rf1 in Formula 1 is,
A fluoropolyether-modified amine compound which is a perfluoropolyether group. A surface treatment agent containing a fluoropolyether-modified amine compound represented by the following Formula 1-1:
[Formula 1-1]

In Formula 1-1,
Rf1 is a monovalent fluoropolyether group;
X ₁ is It is a divalent substituent selected from an amide bond, an ether bond, a thioether bond, an ester bond, a carbamate bond and a ketone bond;
Y ₁ is C ₁ -C ₂₀ alkylene, and in the alkylene at least one non-adjacent -CH2- is -O-, -S-, -C(=O)-, -NR-, or a combination thereof Wherein R is hydrogen or C ₁ -C ₇ alkyl;
R ₁ to R ₂ are each independently hydrogen or C ₁ -C ₂₀ alkyl. A curable composition comprising a fluoropolyether-modified amine compound represented by the following Formula 1-1, a photopolymerizable compound, a photoinitiator, and a solvent:
[Formula 1-1]

In Formula 1-1,
Rf1 is a monovalent fluoropolyether group;
X ₁ is It is a divalent substituent selected from an amide bond, an ether bond, a thioether bond, an ester bond, a carbamate bond and a ketone bond;
Y ₁ is C ₁ -C ₂₀ alkylene, and in the alkylene at least one non-adjacent -CH2- is -O-, -S-, -C(=O)-, -NR-, or a combination thereof Wherein R is hydrogen or C ₁ -C ₇ alkyl;
R ₁ to R ₂ are each independently hydrogen or C ₁ -C ₂₀ alkyl. A cured product of the curable composition according to claim 9. The method of claim 10,
The cured product,
A cured product that is an optical film for preventing contamination or reflection of a flat panel display.