Polymeric composition, cured film thereof, and optical member and display device comprising same

Abstract

The present invention provides a polymerizable composition comprising: a fluorine-based photopolymeric first monomer in which one or two hydrogens of a terminal methyl group are substituted with fluorine, or none are substituted; a photopolymeric second monomer having a linking group containing a heteroatom between a photopolymeric functional group and a terminal perfluorocarbon; and a photoinitiator.

Description

Polymerizable composition, cured film thereof, and optical member and display device including the same

[0001] The present invention relates to a polymerizable composition, a cured film thereof, and an optical member and a display device comprising the same.

[0002] There is a growing need to improve light efficiency in OLEDs (Organic Light Emitting Diodes) and image sensors. Recently, research and development on refractive index-controlled optical films has been actively underway as a technology essential for improving OLED lifespan and increasing battery efficiency.

[0003] The theoretical lower limit of the low refractive index range controllable by organic compounds is known to be approximately 1.45. When hollow silica is mixed, the refractive index decreases, but due to compatibility issues with organic compounds, problems such as reduced transmittance, haze, and adhesion between the upper and lower films occur. Furthermore, the increased viscosity of the composition leads to problems such as reduced inkjet processability, resulting in many technical limitations.

[0004] Fluoropolymer acrylic resins are suitable for producing low-refractive index coating solutions because they have high transmittance and a refractive index of 1.42 or less. However, fluoropolymer acrylic resins have low compatibility with organic compounds, which causes haze during photopolymerization and leads to problems in inkjet processes such as coating properties, chemical resistance, and ejection properties, so the development of technology to solve these issues is required.

[0005] The present invention aims to provide a polymerizable composition having excellent optical properties such as low refractive index, high transmittance, and haze, as well as excellent inkjet ejection characteristics and chemical resistance, a cured film thereof, and an optical member and a display device including the same.

[0006] The above tasks and additional tasks are described in detail below.

[0007] In order to solve the aforementioned problem,

[0008] In one embodiment, the present invention provides a polymerizable composition comprising a fluorine-based photopolymerizable first monomer in which one or two hydrogens of a terminal methyl group are substituted with fluorine or none are substituted, and a photopolymerizable second monomer having a linker containing a heteroatom between a photopolymerizable functional group and a terminal perfluorocarbon.

[0009] In addition, the present invention provides, in one embodiment, a cured film comprising a cured product of the polymerizable composition.

[0010] In addition, the present invention provides an optical member comprising the hardened film in one embodiment.

[0011] In addition, the present invention provides, in one embodiment, a display device comprising a cured film in which the polymerizable composition is cured.

[0012] A polymerizable composition according to one embodiment of the present invention provides a polymerizable composition, a cured film, an optical member, and a display device having excellent optical properties such as low refractive index, high transmittance, and haze, as well as excellent inkjet ejection properties and chemical resistance.

[0013] The above effects and additional effects are described in detail below.

[0014] Before describing the present invention in detail below, it should be understood that the terms used in this specification are intended only to describe specific embodiments and are not intended to limit the scope of the invention, which is defined solely by the appended claims. Unless otherwise stated, all technical and scientific terms used in this specification have the same meaning as generally understood by those skilled in the art.

[0015] Throughout this specification and claims, unless otherwise noted, the terms "comprise," "comprising," and "comprising" mean including the mentioned article, step, or group of articles and steps, and are not used to mean excluding any other article, step, or group of articles or groups of steps.

[0016] Throughout this specification and claims, the term “aryl” means comprising an aromatic hydrocarbon ring group having C5-50, e.g., phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perylenyl, crisenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocrisenyl, anthracenyl, stilbenyl, pyrenyl, etc., and “heteroaryl” means an aromatic ring having C2-50 comprising at least one heteroatom, e.g., pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, It may mean including heterocyclic rings formed from acrridinyl, phenanthrolinyl, thienyl, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acrridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzofuran ring, thiazole ring, thiadiazole ring, benzothiophene ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, etc. Additionally, the term "arylene" means that a hydrogen in the above aryl group is replaced by a direct bond to become a divalent substituent, and specific examples are not limited to cases where the above-described aryl structure becomes a divalent substituent. Likewise, the term "heteroarylene" means that a hydrogen in the above heteroaryl group is replaced by a direct bond to become a divalent substituent, and specific examples are not limited to cases where the above-described heteroaryl structure becomes a divalent substituent.

[0017] Also, in the chemical formula, Ar x(where x is an integer) means, unless specifically defined, a substituted or unsubstituted C6–C50 aryl group, or a substituted or unsubstituted C2–C50 heteroaryl group, and L x (where x is an integer) means a directly bonded, substituted, or unsubstituted C6–C50 arylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, unless specifically defined, and R x (where x is an integer) means, unless specifically defined, hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2-C50 heteroaryl group.

[0018] Throughout this specification and claims, the term “substituted or unsubstituted” refers to a deuterium, halogen, amino group, cyano group, nitrile group, nitro group, nitroso group, sulfamoyl group, isothiocyanate group, thiocyanate group, carboxyl group, carbonyl group, or a C1–C30 alkyl group, a C1–C30 alkylsulfinyl group, a C1–C30 alkylsulfonyl group, a C1–C30 alkylsulfanyl group, a C1–C12 fluoroalkyl group, a C2–C30 alkenyl group, a C1–C30 alkoxy group, a C1–C12 N-alkylamino group, a C2–C20 N,N-dialkylamino group, a substituted or unsubstituted C1–C30 sulfide group, a C1–C6 N-alkylsulfamoyl group, a C2–C12 N,N-dialkylsulfamoyl group, It may mean that it is substituted or not substituted with one or more groups selected from the group consisting of C0-C30 silyl groups, C3-C20 cycloalkyl groups, C3-C20 heterocycloalkyl groups, C6-C50 aryl groups, and C3-C50 heteroaryl groups. Additionally, throughout this specification, the same symbols may have the same meaning unless specifically stated otherwise.

[0019] Meanwhile, matters described in the specification using the above-defined terms such as "aryl," "heteroaryl," "arylene," "heteroarylene," and "substitution" are deemed to include the examples listed above and their combinations; accordingly, the above-mentioned terms may be replaced by the examples listed above or subsequently modified.

[0020] In addition, when ranges such as "C2 to C50" or "0 to 7" are described in this specification, they may be reduced to various ranges within the described ranges even without special description, and are deemed to be described in this specification. For example, C2 to C50 is deemed to describe various reduced ranges such as C5 to C50, C6 to C30, C6 to C20, C6 to C15, C6 to C10, and C12 to C30, in addition to C2 to C50. Accordingly, the description of numerical ranges in this specification may be reduced and corrected later.

[0021] Meanwhile, various embodiments of the present invention may be combined with any other embodiments unless explicitly stated otherwise. Hereinafter, embodiments of the present invention and the effects thereof will be described.

[0022] A polymerizable composition according to one embodiment of the present invention comprises a fluorine-based photopolymerizable first monomer in which one or two hydrogens of a terminal methyl group are substituted with fluorine or none are substituted, and a photopolymerizable second monomer having a linker containing a heteroatom between a photopolymerizable functional group and a terminal perfluorocarbon.

[0023] The first monomer above has hydrogen present in the terminal methyl groups, which are not entirely substituted with fluorine, thereby increasing the compatibility of the composition and suppressing swelling, and the second monomer has a linker containing heteroatoms, which can lower viscosity, reduce volatility, and increase the surface tension of the composition. Accordingly, a polymerizable composition with excellent optical properties such as low refractive index, high transmittance, and haze, as well as excellent inkjet ejection characteristics and chemical resistance, can be realized.

[0024] Fluorine-based photopolymerizable first monomer

[0025] The fluorine-based photopolymerizable first monomer according to one embodiment of the present invention may include a compound represented by the following chemical formula 1.

[0026] <Chemical Formula 1>

[0027] B-X1-A-CH n F 3-n

[0028] In the above chemical formula 1,

[0029] B is a photopolymerizable functional group, and

[0030] X1 is a directly bonded, substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C3-C50 cycloalkylene group, a substituted or unsubstituted C1-C50 heterocycloalkylene group, a substituted or unsubstituted C3-C50 cycloalkenylene group, a substituted or unsubstituted C2-C50 heterocycloalkenylene group, or a substituted or unsubstituted C2-C50 heteroarylene group, or a combination thereof, and the -CH2- present in X1 may be replaced with -O-, -S-, -CO-, -C(OR4)R4-, -NR4-, -C(=NR4)-, -Si(R4)2-, or -P(R4)2-, and

[0031] R4 is each independently hydrogen, deuterium, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted C0-C30 amine group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C0-C30 silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C2-C30 heterocycloalkenyl group, substituted or unsubstituted C3-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group, and

[0032] A is a C1–C20 linear, branched, or cyclic alkylene group in which one or more fluorine atoms are bonded to each carbon atom, and

[0033] n is an integer from 1 to 3.

[0034] According to one embodiment of the present invention, in the above formula 1,

[0035] X1 may specifically be a directly bonded, substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C0-C30 silyl group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted C3-C30 cycloalkenylene group, a substituted or unsubstituted C2-C30 heterocycloalkenylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof.

[0036] More specifically, it may be a substituted or unsubstituted C1-C30 alkylene group, an unsubstituted C1-C30 alkylene group, an unsubstituted C1-C10 alkylene group, or an unsubstituted C1-C5 alkylene group. For example, it may be methylene or ethylene. Within the above range, the compatibility of the composition may be further increased, swelling may be further suppressed, and inkjet ejection characteristics and chemical resistance may be better.

[0037] According to one embodiment of the present invention, in the above formula 1,

[0038] A may be a linear, branched, or cyclic C1 to C20 alkylene group in which one or more fluorine atoms are bonded per carbon atom. Specifically, it may be a linear, branched, or cyclic C5 to C20, C5 to C15, or C5 to C14 alkylene group in which one or more fluorine atoms are bonded per carbon atom. It may be a linear alkylene group. More specifically, the alkylene group listed above may be a linear alkylene group. Additionally, the alkylene group listed above may have two fluorine atoms bonded per carbon atom. Volatility and ejectability may be affected depending on the chain length. Within the above range, the compatibility of the composition may be further increased, swelling may be further suppressed, optical properties such as low refractive index, high transmittance, and haze may be superior, and inkjet ejection characteristics and chemical resistance may be superior.

[0039] According to one embodiment of the present invention, in the above formula 1,

[0040] n can specifically be 1. Or n can specifically be 2. Or n can specifically be 3. When n is 3, swelling inhibition characteristics may be excellent, but the manufacturing cost may increase. Considering swelling inhibition characteristics and manufacturing cost, n can be 1.

[0041] According to one embodiment of the present invention, in the above formula 1,

[0042] B can specifically be an acryloyloxy group, a methacryloyloxy group, or a vinyl group, and more specifically, an acryloyloxy group or a methacryloyloxy group having a C1 to C3 alkyl group. This can improve polymerization reactivity and conversion rate.

[0043]

[0044] According to one embodiment of the present invention, the first monomer may comprise a compound represented by any one of the following chemical structural formulas A-1 to A-8.

[0045]

[0046] In the above chemical structural formula,

[0047] R is a C1–C20 linear, branched, or cyclic alkylene group, and

[0048] a is an integer from 0 to 5, and specifically can be an integer from 1 to 2,

[0049] b is an integer from 1 to 20, and specifically, may be an integer from 5 to 14.

[0050] According to one embodiment of the present invention, the first monomer may be included in an amount of 10 to 90 parts by weight per 100 parts by weight of the total monomer. Specifically, it may be included in an amount of 50 to 80 parts by weight.

[0051] Photopolymerizable second monomer

[0052] The photopolymerizable second monomer having a linker containing a heteroatom between the photopolymerizable functional group and the terminal perfluorocarbon according to one embodiment of the present invention may include a compound represented by the following chemical formula 2.

[0053] <Chemical Formula 2>

[0054] B-X2-A-CH m F 3-m

[0055] In the above chemical formula 2,

[0056] B is a photopolymerizable functional group, and

[0057] X2 is a substituted or unsubstituted C1–C50 alkylene group, a substituted or unsubstituted C2–C50 alkenylene group, a substituted or unsubstituted C0–C50 silyl group, a substituted or unsubstituted C3–C50 cycloalkylene group, a substituted or unsubstituted C1–C50 heterocycloalkylene group, a substituted or unsubstituted C3–C50 cycloalkenylene group, a substituted or unsubstituted C2–C50 heterocycloalkenylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, or a combination thereof, wherein the -CH2- present in X2 may be replaced with -O-, -S-, -CO-, -C(OR4)R4-, -NR4-, -C(=NR4)-, -Si(R4)2-, or -P(R4)2-, and one or more -CH2- may be -O-, -NR4-, or It is replaced with -S-,

[0058] R4 is each independently hydrogen, deuterium, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted C0-C30 amine group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C0-C30 silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C2-C30 heterocycloalkenyl group, substituted or unsubstituted C3-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group, and

[0059] A is a C1–C20 linear, branched, or cyclic alkylene group in which one or more fluorine atoms are bonded to each carbon atom, and

[0060] m is an integer from 0 to 3.

[0061] According to one embodiment of the present invention, in the above formula 2,

[0062] X2 may specifically be a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C0-C30 silyl group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted C3-C30 cycloalkenylene group, a substituted or unsubstituted C2-C30 heterocycloalkenylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof, and one or more -CH2- present in X2 are replaced with -O-, -NR4- or -S-, specifically -O-.

[0063] More specifically, X2 may be a C1 to C30 alkylene group in which one or more -CH2- groups are replaced by -O-. More specifically, it may be a structure having ethylene oxide (-CH2-CH2-O-) or propylene oxide (CH2-CHCH3-O-) repeating units in the range of 1 to 10. More specifically, it may be a structure having units in the range of 1 to 3. Through this, viscosity can be lowered, volatility can be reduced, and the surface tension of the composition can be increased, and a polymerizable composition with excellent inkjet ejection characteristics can be realized.

[0064] According to one embodiment of the present invention, in the above formula 2,

[0065] A may be a linear, branched, or cyclic C1 to C20 alkylene group in which one or more fluorine atoms are bonded per carbon atom. Specifically, it may be a linear, branched, or cyclic C5 to C20, C5 to C15, or C5 to C14 alkylene group in which one or more fluorine atoms are bonded per carbon atom. More specifically, the alkylene group listed above may be a linear alkylene group. Additionally, the alkylene group listed above may have two fluorine atoms bonded per carbon atom. Within the above range, the compatibility of the composition may be further increased, swelling may be further suppressed, optical properties such as low refractive index, high transmittance, and haze may be superior, and inkjet ejection characteristics and chemical resistance may be superior.

[0066] According to one embodiment of the present invention, in the above formula 2,

[0067] m can be specifically 0. Or n can be specifically 1. Or n can be specifically 2. Or n can be specifically 3. When n is 3, swelling inhibition characteristics may be excellent, but the manufacturing cost may increase. Considering swelling inhibition characteristics and manufacturing cost, n can be 1.

[0068] According to one embodiment of the present invention, in the above formula 2,

[0069] B can specifically be an acryloyloxy group, a methacryloyloxy group, or a vinyl group, and more specifically, an acryloyloxy group or a methacryloyloxy group having a C1 to C3 alkyl group. This can improve polymerization reactivity and conversion rate.

[0070] According to one embodiment of the present invention, the second monomer may comprise a compound represented by any one of the following chemical structural formulas B-1 to B-8.

[0071]

[0072] In the above chemical structural formula,

[0073] R is a C1–C20 linear, branched, or cyclic alkylene group, and

[0074] a is an integer from 0 to 5, and

[0075] b is an integer from 1 to 20, and specifically can be an integer from 5 to 14, and

[0076] c is an integer from 1 to 10.

[0077] According to one embodiment of the present invention, the second monomer may be included in an amount of 10 to 90 parts by weight per 100 parts by weight of the total monomer. Specifically, it may be included in an amount of 15 to 45 parts by weight.

[0078] In addition, the weight ratio of the first monomer and the second monomer may be 99:1 to 5:5, specifically 9:1 to 5:5, and more specifically 8:2 to 5:5. If the content of the second monomer is greater than that of the first monomer, the refractive index characteristics may deteriorate.

[0079] Polyfunctional photopolymerizable tert-monomer

[0080] A polymerizable composition according to one embodiment of the present invention may further include a polyfunctional photopolymerizable third monomer selected from one or more of a polyfunctional photopolymerizable monomer in which some or all of the hydrogen is substituted with fluorine and a polyfunctional photopolymerizable monomer in which fluorine is not present.

[0081] By curing using a third monomer, mechanical properties such as chemical resistance, film durability, and modulus can be improved. In particular, by including a polyfunctional photopolymerizable monomer in which some or all of the hydrogen is substituted with fluorine as a component, optical properties such as low refractive index, high transmittance, and haze can be simultaneously improved.

[0082] Meanwhile, by including a fluorine-free multifunctional photopolymerizable monomer as a component, excellent inkjet ejection characteristics and chemical resistance can be achieved simultaneously.

[0083] The above third monomer may be selected from one or more compounds represented by the following chemical formulas 3-1 and 3-2.

[0084] <Chemical Formula 3-1>

[0085] (B)p-L1-Y1- L1-(B)q

[0086] <Chemical Formula 3-2>

[0087] (B)p-L2-Y2- L2-(B)q

[0088] In the above chemical formulas 3-1 and 3-2,

[0089] B is a photopolymerizable functional group, and

[0090] L1 and L2 are each independently a directly bonded, substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C3-C50 cycloalkylene group, a substituted or unsubstituted C1-C50 heterocycloalkylene group, a substituted or unsubstituted C3-C50 cycloalkenylene group, a substituted or unsubstituted C2-C50 heterocycloalkenylene group, or a substituted or unsubstituted C2-C50 heteroarylene group, or a combination thereof, and the -CH2- present in L1 and L2 may be replaced with -O-, -S-, -CO-, -C(OR4)R4-, -NR4-, -C(=NR4)-, -Si(R4)2-, or -P(R4)2-.

[0091] R4 is each independently hydrogen, deuterium, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted C0-C30 amine group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C0-C30 silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C2-C30 heterocycloalkenyl group, substituted or unsubstituted C3-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group, and

[0092] Y1 is a C1–C50 linear, branched, or cyclic alkylene group having one or more fluorine substituents, and

[0093] Y2 is a C1–C50 linear, branched, or cyclic alkylene group without fluorine substituents, and

[0094] p and q are each independently integers from 0 to 5, and p+q is an integer from 2 to 10.

[0095] According to one embodiment of the present invention, in Formula 3-1 and Formula 3-2,

[0096] B can specifically be an acryloyloxy group, a methacryloyloxy group, or a vinyl group, and more specifically, an acryloyloxy group or a methacryloyloxy group having a C1 to C3 alkyl group. This can improve polymerization reactivity and conversion rate.

[0097] According to one embodiment of the present invention, in Formula 3-1 and Formula 3-2,

[0098] Specifically, p and q may each be independently integers from 0 to 3 and p+q may be an integer from 2 to 6; more specifically, p and q may each be independently integers from 1 to 2 and p+q may be an integer from 2 to 4; and more specifically, p and q may be 1. By having an appropriate number of photopolymerizable functional groups, the conversion rate and coating properties can be improved.

[0099] According to one embodiment of the present invention, in Formula 3-1 and Formula 3-2,

[0100] L1 and L2 may each independently be a directly bonded, substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C0-C30 silyl group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C1-C30 heterocycloalkylene group, a substituted or unsubstituted C3-C30 cycloalkenylene group, a substituted or unsubstituted C2-C30 heterocycloalkenylene group, or a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof. By optimizing the molecular length of the monomer, mechanical properties such as chemical resistance, coating durability, and modulus can be improved.

[0101] According to one embodiment of the present invention, in the above formula 3-1,

[0102] Y1 may specifically be a linear, branched, or cyclic C1-C30 alkylene group having one or more fluorine substituents, and specifically may be a linear, branched, or cyclic C1-C20, C5-C20, C5-C15, or C5-C14 alkylene group in which one or more fluorine atoms are bonded per carbon atom. More specifically, the alkylene group listed above may be a linear alkylene group. Additionally, the alkylene group listed above may have two fluorine atoms bonded per carbon atom. Within the above range, optical properties such as low refractive index, high transmittance, and haze may be superior, and inkjet ejection characteristics and chemical resistance may be superior.

[0103] According to one embodiment of the present invention, in the above formula 3-2,

[0104] Y2 may be a linear, branched, or cyclic C1 to C30 alkylene group without fluorine substituents, and specifically may be an unsubstituted linear, branched, or cyclic C1 to C20, C5 to C20, C5 to C15, or C5 to C14 alkylene group. More specifically, the alkylene groups listed above may be linear alkylene groups. Within the above range, optical properties such as high transmittance and haze may be superior, and inkjet ejection characteristics and chemical resistance may be superior.

[0105] According to one embodiment of the present invention,

[0106] The above third monomer comprises a compound represented by the above chemical formula 3-1, and

[0107] The above chemical formula 3-1 is ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, butanediol di(meth)acrylate, pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, isostearyl acrylate, lauryl acrylate, 1,6-hexanediol ethoxylate di(meth)acrylate, Dipentaerythritol hexaacrylate, kayarad DPCA-20, kayarad DPCA-30, kayarad DPCA-60, kayarad DPCA-120, and kayarad One or more of dpea-12 can be selected.

[0108] According to one embodiment of the present invention,

[0109] The above third monomer comprises a compound represented by the above chemical formula 3-2, and

[0110] The above chemical formula 3-2 may be selected from one or more of 1H,1H,5H,5H-perfluoro-1,5-pentanediol di(meth)acrylate, 1H,1H,6H,6H-perfluoro-1,6-hexanediol di(meth)acrylate, 1H,1H,8H,8H-perfluoro-1,8-octanediol di(meth)acrylate, 1H,1H,9H,9H-perfluoro-1,9-nonanediol di(meth)acrylate, 1H,1H,10H,10H-perfluoro-1,10-decanediol di(meth)acrylate, and 1H,1H,10H,10H-hexadecafluoro-1,10-decanediol di(meth)acrylate.

[0111] According to one embodiment of the present invention, the third monomer may be included in an amount of 1 to 10 parts by weight per 100 parts by weight of the total monomer. Specifically, it may be included in an amount of 1 to 5 parts by weight.

[0112] Photopolymerization Initiator

[0113] According to one embodiment of the present invention, a photopolymerization initiator may be included. The photopolymerization initiator may include at least one of a phosphine oxide-based compound, an acetophenone-based compound, an acylphosphine oxide-based compound, (E)-2-(acetoxyimino)-1-(9,9-diethyl-9H-fluorene-2-yl)butanone, [1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazoyl-3-yl]-1-(O-acetyloxime), an oxime-based compound, and an oxime ester-based compound. Specifically, the photopolymerization initiator may include at least a phosphine oxide-based compound. When using the aforementioned types of photopolymerization initiators, stable photocuring of the polymerizable composition can be induced, thereby improving the optical properties of the cured product of the polymerizable composition. As the above photopolymerization initiator, for example, phosphine oxide-based compounds such as Darocure TPO, Omnirad TPO, or Irgacure TPO (Jiuri), acetophenone-based compounds such as Irgacure 369 and Irgacure 907, oxime-based compounds such as OXE-01, and oxime ester-based compounds such as OXE-04 may be used.

[0114] According to one embodiment of the present invention, with respect to 100 parts by weight of a monomer mixture comprising the first high-flexibility monomer, the second high-flexibility monomer, and the high-hardness monomer, the content of the photopolymerization initiator may be 1 part by weight or more and 20 parts by weight or less, 1 part by weight or more and 10 parts by weight or less, 5 parts by weight or more and 15 parts by weight or less, 5 parts by weight or more and 10 parts by weight or less, 10 parts by weight or more and 20 parts by weight or less, 10 parts by weight or more and 15 parts by weight or less, or 15 parts by weight or more and 20 parts by weight or less. By controlling the content of the photopolymerization initiator to the aforementioned range, the polymerization reaction of the first high-flexibility monomer, the second high-flexibility monomer, and the high-hardness monomer included in the polymerizable composition can be carried out effectively and stably.

[0115] According to one embodiment of the present invention, the photopolymerization initiator may include one or more photopolymerization initiators. Specifically, the photopolymerization initiator may include a first photopolymerization initiator and a second photopolymerization initiator. The photopolymerization initiator may include a phosphine oxide-based compound. Additionally, the second photopolymerization initiator may include at least one of an acetophenone-based compound, an acylphosphine oxide-based compound, (E)-2-(acetoxyimino)-1-(9,9-diethyl-9H-fluorene-2-yl)butanone, [1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazoyl-3-yl]-1-(O-acetyloxime), an oxime-based compound, and an oxime ester-based compound. By using a mixture of the first photopolymerization initiator and the second photopolymerization initiator, stable photocuring of the polymerizable composition can be induced.

[0116] Other ingredients

[0117] In addition to the components described above, the polymerizable composition according to one embodiment of the present invention may optionally include, but is not limited to, solvents, antioxidants, UV absorbers, thermal polymerization inhibitors, leveling agents, surfactants, lubricants, etc.

[0118] According to one embodiment of the present invention, the viscosity of the polymerizable composition may be 5 cP or more and 30 cP or less. The viscosity of the polymerizable composition may be measured at 25°C. The polymerizable composition having a viscosity satisfying the aforementioned range may be easy to use in an inkjet.

[0119] As another embodiment, the present invention provides a cured film comprising a cured product of the aforementioned polymerizable composition, wherein the refractive index of the cured film may be 1.41 or less. Specifically, the cured film may have a refractive index of 1.41 or less when measured at a wavelength of 550 nm. Since the cured film exhibits low low-refractive index characteristics with a refractive index of 1.41 or less, it is possible to realize an optical member and a display device with excellent optical properties.

[0120] One embodiment of the present invention provides an optical member comprising the hardened film.

[0121] According to one embodiment of the present invention, the optical member can realize excellent optical properties, such as increased light efficiency, by including the cured film. In addition, the optical member can have excellent durability by having excellent chemical resistance even under high temperature and high humidity conditions.

[0122] According to one embodiment of the present invention, the optical member may include a substrate; and the cured film provided on the substrate. Additionally, the cured film may be formed by photocuring after the polymerizable composition is applied onto the substrate by an inkjet process. In this case, a well-known substrate, such as bare glass, may be used as the substrate.

[0123] Additionally, the optical member may be manufactured by applying the polymerizable composition onto the substrate using a Mayer bar, a coating applicator, or inkjet equipment, and then performing photocuring by exposure using, for example, an LED lamp or a metal halide lamp in an air atmosphere. At this time, the polymerizable composition may be applied in a single film form and then photocured to form an optical member in the form of a general optical film, but if necessary, it may also be applied using the inkjet equipment to form a specific pattern and then photocured. In this case, the optical member may take the form of a pattern film in which a cured film patterned in the form of, for example, a prism structure or a lens structure is formed on the substrate.

[0124] Hereinafter, the present invention will be described in detail with reference to examples to specifically explain the invention. However, the embodiments according to the present invention may be modified in various different forms, and the scope of the present invention is not to be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present invention to those with average knowledge in the art.

[0125] Fluorine-based photopolymerizable first monomer

[0126] The following compounds were prepared as fluorine-based photopolymerizable first monomers.

[0127]

[0128] Photopolymerizable second monomer

[0129] The following compounds were prepared as photopolymerizable second monomers.

[0130]

[0131] Fluorine-based 3-1 monomer

[0132] The following compounds were prepared as fluorine-based 3-1 monomers.

[0133]

[0134] Non-fluorinated 3-2 monomer

[0135] The following compounds were prepared as non-fluorinated third-second monomers.

[0136]

[0137] Photoinitiator

[0138] Omnirad TPO was prepared as a photoinitiator.

[0139] Examples 1 to 39 and Comparative Examples 1 to 23

[0140] Preparation of polymerizable compositions

[0141] Compounds were prepared with the components and contents of Table 5 below, and monomer mixtures were prepared by mixing the monomers. Subsequently, other components of Table 5 were added and mixed to prepare a polymerizable composition. The contents of Table 5 below refer to parts by weight.

[0142] Preparation of hardened film

[0143] Using an inkjet device (UniJet, OmniJet), the polymerizable composition for inkjet prepared above was applied onto a bare glass substrate to form a single film with a thickness of 10 μm.

[0144] Subsequently, using a 385nm LED curing machine, 2.2J / cm² 2 A cured film (thickness: 10 μm) containing a cured product of a polymerizable composition for inkjet was prepared by irradiating a single film with UV light. Meanwhile, for the refractive index measurement, a cured film with a thickness of 2 μm prepared using spin coating was used.

[0145] Classification 1st Monomer 2nd Monomer 3-1 Monomer 3-2 Monomer Light Initiator Type Content Type Content Type Content Type Content Example 1 150 150----3 Example 2 160 140----3 Example 3 170 130----3 Example 4 180 120----5 Example 5 190 110----5 Example 6 199 11----5 Example 7 189 111----5 Example 8 140 160----5 Example 9 110 190----5 Example 10 140 160----5 Example 1 1150 250----5 Example 1 2260 140----5 Example 1 3560 140----5 Example 14 660140----5 Example 157 60140----5 Example 168 60140----5 Example 17 160240----5 Example 18 148.5 148.513--1.5 Example 19 158.2 138.813--1.5 Example 20 167.9 129.113--1.5 Example 21 177.6 119.413--1.5 Example 22 187.3 19.713--1.5 Example 23 138.8 158.213--1.5 Example 24 158.2 133.823--1.5 Example 25 166.5 128.5--151.5 Example 26 166.5 128.5- -251.5 Example 27266.5128.515--1.5 Example 28566.5128.515--1.5 Example 29166.5128.514111.5 Example 3015014514111.5 Example 3116013514111.5 Example 32266.5128.51 4111.5 Example 33566.5128.514111.5 Example 34166.5228.514111.5 Example 35166.5228.524111.5 Example 36166.5228.524211.5 Example 37175115--1,2 each 51.5 Example 3818515 15251.5 Example 39 185 1915211.5 Comparative Example 1 100------5 Comparative Example 2 1 100----5 Comparative Example 3 360 140----5 Comparative Example 4 460 140----5 Comparative Example 5 160 340----5 Comparative Example 6 260 340----5 Comparative Example 7 360 340----5 Comparative Example 8 590--110--1.5 Comparative Example 9 360 135 15--1.5 Comparative Example 10 360 235 15--1.5 Comparative Example 1 1360 135--151.5 Comparative Example 12 360 135--251.5 Comparative Example 1 3460 135 15--1.5 Comparative Example 1 4460 235 15--1.5 Comparative Example 15460135--151.5 Comparative Example 1646035--251.5 Comparative Example 17---1901101.5 Comparative Example 1836013415111.5 Comparative Example 1936023415111.5 Comparative Example 2036033415111.5 Comparative Example 2146013415111.5 Comparative Example 2246023415111.5 Comparative Example 2346033415111.5.

[0146] Experimental Example

[0147] The following experiments were conducted on the polymerizable compositions and cured films prepared in Examples 1 to 39 and the polymerizable compositions and cured films prepared in Comparative Examples 1 to 23, and the results are listed in Table 6 below.

[0148] 1) Surface tension

[0149] For each of the polymerizable compositions of the above examples and comparative examples, the surface tension at a temperature of 25°C was measured using a surface tension meter (equipment name: K20, KRUSS) with the Du Nouy Ring or Wilhelmy Plate method.

[0150] verdict

[0151] ○: When the surface tension value of the polymerizable composition is 23 to 40 mN / m

[0152] △: When the surface tension value of the photopolymerizable composition is 20 to 23 mN / m

[0153] X: When the surface tension value of the polymerizable composition falls outside the above range

[0154] 2) Viscosity (Absolute Viscosity)

[0155] For each polymerizable composition or monomer of the above examples and comparative examples, the viscosity was measured at a temperature of 25°C using a viscometer (product name: BrookField viscometer).

[0156] verdict

[0157] ○: When the viscosity value is 5 to 30 cP

[0158] X: When the viscosity value falls outside the above range

[0159] 3) Refractive index

[0160] The refractive index (wavelength of 550 nm) of a 2 μm thick cured film formed by applying the above photopolymerization composition onto a silicon wafer and irradiating it with UV light was measured using an ellipsometer.

[0161] verdict

[0162] ○ : When the single-film refractive index measurement is less than 1.40

[0163] △ : When the single-film refractive index measurement is 1.40 or higher and less than 1.41

[0164] X: When the single-layer refractive index measurement is 1.41 or higher

[0165] 4) Transmittance

[0166] The average transmittance of the formed monolayer was measured at wavelengths of 380–780 nm using a UV-vis spectrometer (equipment name: Cary4000, Agilent).

[0167] verdict

[0168] ○: When the average transmittance value is 95% or higher

[0169] X: When the average transmittance value is less than 95%

[0170] 5) Volatility

[0171] 10g of the polymerizable composition was placed in an aluminum cup, and for each composition, the weight change was measured after waiting for 24 hours in an oven set to a temperature of 25℃ and 30℃, and the volatility was calculated using the following formula.

[0172]

[0173] verdict

[0174] ○: When volatility is within 1%

[0175] △: When volatility is 1 to 5%

[0176] X: When volatility is 5% or higher

[0177] 6) Chemical resistance

[0178] The HA-6 component contained in KM1800i SHC-C was immersed in the polymerizable composition of the above examples and comparative examples and left at 25°C for 8 weeks to measure the weight change, and the degree of swelling was calculated using the following formula.

[0179]

[0180] verdict

[0181] ○: When the weight change is less than 20%

[0182] X: When the weight change is 20% or more

[0183] 7) Inkjet Discharge Characteristics

[0184] When the polymerizable compositions of the above examples and comparative examples were ejected using an Inkjet device (OmniJet Series, Unijet) equipped with a Head (Product Name: KM1800i SHC-C, Konica Minolta) that ejects droplets quantified at 4 pico liters, it was checked whether non-ejected nozzles, meandering, or droplet clumping occurred for 1,776 nozzles compared to the initial ejection when the device was left idle for 20 hours at head temperatures of 25℃ and 30℃.

[0185] <Initial Discharge>

[0186]

[0187] Discharge after 20 hours of non-operation standby>

[0188] - Normal discharge

[0189]

[0190] - Mitochu

[0191]

[0192] - Meandering discharge and droplet clumping

[0193]

[0194] verdict

[0195] ◎ : No non-dispensing nozzles, meandering discharge, or droplet clumping when dispensing after 20 hours of standby.

[0196] ○ : When discharging after a 20-hour standby, non-discharging nozzles, meandering discharge, or droplet clumping may occur; however, normal discharge is possible after performing 1 to 10 high-speed discharges for 3 seconds each.

[0197] △ : When discharging after a 20-hour non-operation standby, undischarged nozzles, meandering discharge, or droplet clumping may occur; normal discharging is possible after purging.

[0198] X: When discharging after a 20-hour non-operation standby, non-discharging nozzles, meandering discharge, or droplet clumping occur, and since there is no improvement even after purging, it is impossible.

[0199] 8) Degree of hardening

[0200] After coating the polymerizable compositions of the above examples and comparative examples onto a glass substrate, a thin film with a thickness of 20 μm was formed by exposure at 1.5 J / cm2 in a nitrogen atmosphere, and the spectrum was measured using a Fourier transform infrared spectrometer (FT-IR, Vertex-70V). The conversion rate before and after UV exposure was calculated using the following formula by comparing it with the composition spectrum.

[0201]

[0202] ○ : Conversion rate 95% or higher

[0203] △ : Conversion rate 90% or higher

[0204] X : Conversion rate less than 90%

[0205] 9) Coating properties

[0206] The photopolymerizable compositions of the above examples and comparative examples were checked to see if they formed a surface using an inkjet device.

[0207] verdict

[0208] ◎ : Surfaces can be formed within 20㎛ thickness

[0209] ○ : Surface formation possible at a thickness of 20㎛ or more

[0210] X: Surface not formed

[0211] Examples Surface tension Viscosity Refractive index Transmittance Volatility Chemical resistance Inkjet dispensingCharacteristics Curability Coating Properties 25℃ 30℃ 25℃ 30℃ Example 1 ◎OOOOOO◎◎△◎ Example 2 ◎OOOOOO◎◎△◎ Example 3 ◎OOOOOO◎◎△◎ Example 4 ◎OOOOOO◎◎△◎ Example 5 ◎OOOOOO◎◎△O Example 6 OOOOOOO◎◎△O Example 7 ◎OOOOOO◎◎△O Example 8 ◎O△OOOO◎◎△◎ Example 9 ◎O△OOOO◎◎△◎ Example 10 ◎O△OOOO◎◎△◎ Example 11 ◎O△OOOO◎◎△◎ Example 12 ◎OOOOXO◎O△◎ Example 13 ◎OOOXXOO△△◎ Example 14 ◎OOOOOO◎◎△◎ Example 15 ◎OOOOOO◎ ◎△◎Example 16◎OOOOOO◎◎△O Example 17◎O△OOOO◎◎O◎Example 18◎OOOOOO◎◎O◎Example 19◎OOOOOO◎◎O◎Example 20◎OOOOOO◎◎O◎Example 21◎OOOOOO◎◎O◎Example 22◎OOOOOO◎◎OO Example 23◎O△OOOO◎◎O◎Example 24◎OOOOOOOOO◎Example 25◎OOOOOO◎◎O◎Example 26◎OOOOOO◎◎O◎Example 27◎OOOO△O◎OO◎Example 28◎OOO△XOO△O◎Example 29◎OOOOOO◎◎O◎Example 30◎OOOOOO◎◎O◎Example 31◎ OOOOOO◎◎O◎Example 32◎OOOO△O◎OO◎Example 33◎OOO△XOO△O◎Example 34◎O△OOOO◎◎O◎Example 35◎O△OOOO◎◎O◎Example 36◎O△OOOO◎◎O◎Example 37◎O△OOOO◎◎OOExample 38◎OOOOOO◎◎OOExample 39◎OOOOOO◎◎OOComparative Example 1XOOOXXOXXXXComparative Example 2◎OXOOOO△△△◎Comparative Example 3XOOOXXXXX△◎Comparative Example 4XOOOO△XXX△◎Comparative Example 5XOOOXXOXX△◎Comparative Example 6XOOOXXOXX△◎Comparative Example 7XOOOXXXXX△◎Comparative Example 8O OOOXXOXXO◎Comparison Example 9OOOOXXXXXO◎Comparison Example 10OX△OXXXXXO◎Comparison Example 11OOOOXXXXXO◎Comparison Example 12OOOOXXXXXO◎Comparison Example 13OOOOOOXOOO◎Comparison Example 14OX△OOOXOOO◎Comparison Example 15OOOOOOXOOO◎Comparison Example 16OOOOOOXOOO◎Comparison Example 17OXXOOOOOOO◎Comparison Example 18OOOOXXXXXO◎Comparison Example 19OO△OXXXXXO◎Comparison Example 20OOOOXXXXXO◎Comparison Example 21OOOOOOXOOO◎Comparison Example 22OO△OOOXOOO◎Comparison Example 23OOOOXXXXXO◎

[0212] As can be seen from the results in Table 6 above,

[0213] It can be confirmed that the polymerizable composition according to one embodiment of the present invention exhibits superior surface tension, viscosity, refractive index, transmittance, low volatility, chemical resistance, inkjet ejection characteristics, degree of curing, and coating properties compared to the polymerizable composition of the comparative example. Furthermore, it has been confirmed that the polymerizable composition according to one embodiment of the present invention can be excellently applied to polymerizable compositions for low refractive index applications.

[0214] In particular, the cases of Examples 17 to 20, 24, 25, 28 to 30, 37, and 38 had the best overall characteristics.

[0215] When comparing the embodiments and comparative examples of the present invention,

[0216] In the case of Comparative Example 1, it was confirmed that surface tension, volatility, and inkjet ejection characteristics were reduced because it did not contain the second monomer, and

[0217] In the case of Comparative Examples 5 to 7, it was confirmed that the surface tension, volatility, and inkjet ejection characteristics were reduced because the second monomer did not have an ethyleneoxy structure.

[0218] In the case of Comparative Examples 10 and 14, it was confirmed that the low refractive index characteristics deteriorated somewhat due to the presence of three ethyleneoxy structures in the second monomer.

[0219] In the case of Comparative Examples 2 and 17, it was confirmed that the low refractive index characteristics deteriorated because the first monomer was not contained, and

[0220] In the case of Comparative Examples 4, 7, 9 to 16, and 18 to 23, it was confirmed that the chemical resistance was reduced because the terminals of the first monomer were all substituted with fluorine.

[0221] Furthermore, a person skilled in the art will be able to fully understand the effects of the present invention from the experimental results of the above examples and comparative examples and Table 6.

Claims

1. A fluorine-based photopolymerizable first monomer in which one or two hydrogens of the terminal methyl group are substituted with fluorine or are not substituted at all; and A photopolymerizable second monomer having a linker containing a heteroatom between the photopolymerizable functional group and the terminal perfluorocarbon; Polymerizable composition containing a photoinitiator.

2. In Paragraph 1, The above first monomer is a polymerizable composition represented by the following chemical formula 1: <Chemical Formula 1> B-X1-A-CH n F 3-n In the above chemical formula 1, B is a photopolymerizable functional group, and X1 is a directly bonded, substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C3-C50 cycloalkylene group, a substituted or unsubstituted C1-C50 heterocycloalkylene group, a substituted or unsubstituted C3-C50 cycloalkenylene group, a substituted or unsubstituted C2-C50 heterocycloalkenylene group, or a combination thereof, and the -CH2- present in X1 may be replaced with -O-, -S-, -CO-, -C(OR4)R4-, -NR4-, -C(=NR4)-, -Si(R4)2-, or -P(R4)2-, and R4 is each independently hydrogen, deuterium, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted C0-C30 amine group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C0-C30 silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C2-C30 heterocycloalkenyl group, substituted or unsubstituted C3-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group, and A is a C1–C20 linear, branched, or cyclic alkylene group in which one or more fluorine atoms are bonded to each carbon atom, and n is an integer from 1 to 3.

3. In Paragraph 2, A polymerizable composition in which n is 1.

4. In Paragraph 2, A polymerizable composition in which the above A is a linear, branched, or cyclic C5 to C20 alkylene group in which one or more fluorine atoms are bonded per carbon atom.

5. In Paragraph 2, The above first monomer is a polymerizable composition represented by any one of the following chemical structural formulas A-1 to A-6: In the above chemical structural formula, R is a C1–C20 linear, branched, or cyclic alkylene group, and a is an integer from 0 to 5, and b is an integer from 1 to 20.

6. In Paragraph 1, The above second monomer is a polymerizable composition represented by the following chemical formula 2: <Chemical Formula 2> B-X2-A-CH m F 3-m In the above chemical formula 2, B is a photopolymerizable functional group, and X2 is a substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C3-C50 cycloalkylene group, a substituted or unsubstituted C1-C50 heterocycloalkylene group, a substituted or unsubstituted C3-C50 cycloalkenylene group, a substituted or unsubstituted C2-C50 heterocycloalkenylene group, or a combination thereof, wherein -CH2- present in X2 may be replaced with -O-, -S-, -CO-, -C(OR4)R4-, -NR4-, -C(=NR4)-, -Si(R4)2-, or -P(R4)2-, and one or more -CH2- are replaced with -O-, -NR4-, or -S-, and R4 is each independently hydrogen, deuterium, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted C0-C30 amine group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C0-C30 silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C2-C30 heterocycloalkenyl group, substituted or unsubstituted C3-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group, and A is a C1–C20 linear, branched, or cyclic alkylene group in which one or more fluorine atoms are bonded to each carbon atom, and m is an integer from 0 to 3.

7. In Paragraph 6, The above second monomer is a polymerizable composition represented by any one of the following chemical structural formulas B-1 to B-8: In the above chemical structural formula, R is a C1–C20 linear, branched, or cyclic alkylene group, and a is an integer from 0 to 5, and b is an integer from 1 to 20, and c is an integer from 1 to 10.

8. In Paragraph 1, A polymerizable composition in which the weight ratio of the first monomer to the second monomer is 8:2 to 5:

5.

9. In Paragraph 1, A polymerizable composition further comprising a polyfunctional photopolymerizable third monomer selected from one or more of a polyfunctional photopolymerizable monomer in which some or all of the hydrogen is substituted with fluorine and a polyfunctional photopolymerizable monomer in which fluorine is not present.

10. In Paragraph 9, The above third monomer is a polymerizable composition selected from one or more compounds represented by the following chemical formulas 3-1 and 3-2. <Chemical Formula 3-1> (B)p-L1-Y1-L1-(B)q <Chemical Formula 3-2> (B)p-L2-Y2-L2-(B)q In the above chemical formulas 3-1 and 3-2, B is a photopolymerizable functional group, and L1 and L2 are each independently a directly bonded, substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C0-C50 silyl group, a substituted or unsubstituted C3-C50 cycloalkylene group, a substituted or unsubstituted C1-C50 heterocycloalkylene group, a substituted or unsubstituted C3-C50 cycloalkenylene group, a substituted or unsubstituted C2-C50 heterocycloalkenylene group, or a substituted or unsubstituted C2-C50 heteroarylene group, or a combination thereof, and the -CH2- present in L1 and L2 may be replaced with -O-, -S-, -CO-, -C(OR4)R4-, -NR4-, -C(=NR4)-, -Si(R4)2-, or -P(R4)2-, and R4 is each independently hydrogen, deuterium, halogen, nitrile group, nitro group, hydroxyl group, thiol group, substituted or unsubstituted C0-C30 amine group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C1-C30 sulfide group, substituted or unsubstituted C0-C30 silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C30 heterocycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C2-C30 heterocycloalkenyl group, substituted or unsubstituted C3-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group, and Y1 is a C1–C50 linear, branched, or cyclic alkylene group having one or more fluorine substituents, and Y2 is a C1–C50 linear, branched, or cyclic alkylene group without fluorine substituents, and p and q are each independently integers from 0 to 5, and p+q is an integer from 2 to 10.

11. In Paragraph 10, The above third monomer comprises a compound represented by the above chemical formula 3-1, and The compound represented by the above chemical formula 3-1 is ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, butanediol di(meth)acrylate, pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, isostearyl acrylate, lauryl acrylate, 1,6-hexanediol ethoxylate di(meth)acrylate, Dipentaerythritol hexaacrylate, kayarad dpca-20, kayarad dpca-30, kayarad dpca-60, kayarad dpca-120 and A polymerizable composition selected from one or more of kayarad dpea-12.

12. In Paragraph 10, The above third monomer comprises a compound represented by the above chemical formula 3-2, and The compound represented by the above chemical formula 3-2 is a polymerizable composition selected from one or more of 1H,1H,5H,5H-perfluoro-1,5-pentanediol di(meth)acrylate, 1H,1H,6H,6H-perfluoro-1,6-hexanediol di(meth)acrylate, 1H,1H,8H,8H-perfluoro-1,8-octanediol di(meth)acrylate, 1H,1H,9H,9H-perfluoro-1,9-nonanediol di(meth)acrylate, 1H,1H,10H,10H-perfluoro-1,10-decanediol di(meth)acrylate, and 1H,1H,10H,10H-hexadecafluoro-1,10-decanediol di(meth)acrylate.

13. In Paragraph 9, The first monomer is included in an amount of 10 to 90 parts by weight per 100 parts by weight of the total monomer, and The second monomer is included in an amount of 10 to 90 parts by weight per 100 parts by weight of the total monomer, and A polymerizable composition comprising 1 to 10 parts by weight of the third monomer per 100 parts by weight of the total monomer.

14. A display device comprising a cured film formed by curing the polymerizable composition of claim 1.

15. In Paragraph 14, A display device in which the refractive index of the above-mentioned hardened film is 1.41 or less.

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