Curable composition, cured layer using the curable composition, and display device

Abstract

Provided are a curable composition, a cured layer manufactured using the curable composition, and a display device including the cured layer, the curable composition comprising: (A) quantum dots; (B) a silicon compound obtained by reacting a compound represented by Chemical Formula 1 with a compound represented by Chemical Formula 2; and (C) a polymerizable monomer.

Description

Technical Field

[0001] This disclosure relates to a curable composition, a curable layer using the curable composition, and a display device including the curable layer. Background Technology

[0002] In the case of general quantum dots, the solvents in which quantum dots can be dispersed are limited due to their hydrophobic surface properties, and therefore it is difficult to introduce them into polar systems (such as adhesives or curable monomers).

[0003] For example, even in the case of quantum dot ink compositions that are being actively researched, the polarity is relatively low in the initial steps, and quantum dot ink compositions can be dispersed in solvents used in curable compositions with high hydrophobicity. Therefore, since it is difficult to include 20% by weight or more of quantum dots in the total composition, it is impossible to increase the light efficiency of the ink beyond a certain level. Even if additional quantum dots are added and dispersed to increase light efficiency, the viscosity will exceed the range suitable for inkjet printing, and therefore the processability may be unsatisfactory.

[0004] To achieve a viscosity range suitable for inkjet printing, one approach is to reduce the ink solids content by dissolving 50% by weight or more of a solvent based on the total composition. This method also provides somewhat satisfactory results in terms of viscosity. However, while this may be considered a satisfactory result in terms of viscosity, issues such as nozzle drying and clogging due to solvent evaporation during inkjet printing, as well as a decrease in monolayer thickness over time after inkjet printing, can worsen, and it is difficult to control thickness deviations after curing. Therefore, it is difficult to apply this method to practical processes.

[0005] Therefore, solvent-free quantum dot inks, which do not contain solvents, are the most preferable form for practical applications. Current technology for applying quantum dots themselves to solvent-based compositions is currently limited to some extent. Summary of the Invention

[0006] Technical challenges

[0007] One embodiment provides a curable composition with excellent refractive index, optical properties and lightfastness.

[0008] Another embodiment provides a cured layer manufactured using the said curable composition.

[0009] Another embodiment provides a display device including the cured layer.

[0010] Problem Solving Methods

[0011] One embodiment provides a curable composition comprising: (A) quantum dots; (B) a silicon compound obtained by reacting a compound represented by chemical formula 1 with a compound represented by chemical formula 2; and (C) a polymerizable monomer.

[0012] [Chemical Formula 1]

[0013]

[0014] [Chemical Formula 2]

[0015]

[0016] In chemical formula 1 and chemical formula 2,

[0017] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0018] R 2 R 4 R 7 and R 8 Each is independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.

[0019] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0020] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group, and

[0021] L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0022] Silicon compounds may include structural units represented by chemical formula 1-1 and structural units represented by chemical formula 2-1.

[0023] [Chemical Formula 1-1]

[0024]

[0025] [Chemical Formula 2-1]

[0026]

[0027] In chemical formulas 1-1 and 2-1,

[0028] R 1It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0029] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0030] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group, and

[0031] L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0032] Silicon compounds can be compounds obtained by further reacting compounds represented by chemical formula 3, in addition to those represented by chemical formula 1 and those represented by chemical formula 2.

[0033] [Chemical Formula 3]

[0034]

[0035] In chemical formula 3,

[0036] R 9 To R 12 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group.

[0037] Silicon compounds may include structural units represented by chemical formula 1-1, structural units represented by chemical formula 2-1, and structural units represented by chemical formula 3-1.

[0038] [Chemical Formula 1-1]

[0039]

[0040] [Chemical Formula 2-1]

[0041]

[0042] [Chemical Formula 3-1]

[0043]

[0044] In chemical formulas 1-1 to 3-1

[0045] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0046] R 3It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0047] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0048] R 9 and R 11 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group, and

[0049] L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0050] Silicon compounds may include structural units represented by chemical formula 4.

[0051] [Chemical Formula 4]

[0052]

[0053] In chemical formula 4,

[0054] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0055] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0056] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0057] L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group.

[0058] n and m are each an independent integer greater than or equal to 1, with the constraint that n ≥ m.

[0059] Silicon compounds may include structural units represented by chemical formula 5.

[0060] [Chemical Formula 5]

[0061]

[0062] In chemical formula 5,

[0063] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0064] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0065] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0066] R 9 and R 11 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group.

[0067] L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group, and

[0068] n, m, and q are each an independent integer greater than or equal to 1, with the constraints that n ≥ m and n > q.

[0069] Silicon compounds may have a weight average molecular weight of 500 g / mol to 1,500 g / mol. Polymerizable monomers may include compounds with a refractive index greater than or equal to 1.60.

[0070] The curable component may also include a dispersant.

[0071] Dispersants may include barium sulfate, calcium carbonate, titanium dioxide, zirconium oxide, or combinations thereof.

[0072] Quantum dots can be quantum dots that absorb light at 360 nm to 780 nm and emit fluorescence at 500 nm to 700 nm.

[0073] The curable composition comprises, by weight, 5% to 60% (A) quantum dots; 10% to 30% (B) silicon compounds; and 30% to 80% (C) polymerizable monomers.

[0074] The curable component may further include: polymerization inhibitor; malonic acid; 3-amino-1,2-propanediol; silane coupling agent; leveling agent; fluorinated surfactant; or combinations thereof.

[0075] Another embodiment provides a curing layer manufactured using the curable composition.

[0076] Another embodiment provides a display device including the cured layer.

[0077] Other embodiments of the present invention are included in the following detailed description.

[0078] The effects of the invention

[0079] It can provide a curable composition with excellent refractive index, optical properties and lightfastness. Detailed Implementation

[0080] Embodiments of the invention are described in detail below. However, these embodiments are exemplary, and the invention is not limited thereto, and is defined by the scope of the claims.

[0081] Unless otherwise defined, “alkyl” as used herein refers to C1 to C20 alkyl, “alkenyl” as refers to C2 to C20 alkenyl, “cycloalkenyl” as refers to C3 to C20 cycloalkenyl, “heterocyclic alkenyl” as refers to C3 to C20 heterocyclic alkenyl, “aryl” as refers to C6 to C20 aryl, “arylalkyl” as refers to C6 to C20 arylalkyl, “alkylene” as refers to C1 to C20 alkylene, “arylene” as refers to C6 to C20 arylene, “alkylarylene” as refers to C6 to C20 alkylarylene, “heteroarylene” as refers to C3 to C20 heteroarylene, and “alkoxide” as refers to C1 to C20 alkoxide.

[0082] Unless otherwise specifically defined, “substituted” as used herein means that at least one hydrogen atom is replaced by a substituent selected from the following: halogen atom (F, Cl, Br or I), hydroxyl, C1 to C20 alkoxy, nitro, cyano, amino, imino, azido, amido, hydrazine, hydrazone, carbonyl, carbamoyl, thiol, ester, ether, carboxyl or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C20 aryl, C3 to C20 cycloalkyl, C3 to C20 cycloalkenyl, C3 to C20 cycloalkynyl, C2 to C20 heterocyclic alkyl, C2 to C20 heterocyclic alkenyl, C2 to C20 heterocyclic alkynyl, C3 to C20 heterocyclic aryl, or combinations thereof.

[0083] Unless otherwise defined, “heterogeneous” as used herein refers to a chemical formula containing at least one heteroatom of N, O, S and P.

[0084] Unless otherwise defined, “(meth)acrylate” as used herein refers to both “acrylate” and “methacrylate”, and “(meth)acrylic acid” refers to both “acrylic acid” and “methacrylic acid”.

[0085] Unless otherwise defined, the term “combination” as used herein refers to a mixture or copolymer.

[0086] In this specification, unless otherwise defined, hydrogen bonds are located at the positions indicated in the chemical formula when chemical bonds are not drawn where they should be.

[0087] Additionally, unless otherwise defined in this specification, " "" refers to a point connected to the same or different atoms or chemical formulas.

[0088] The curable composition according to the embodiments comprises: (A) quantum dots; (B) a silicon compound obtained by reacting a compound represented by chemical formula 1 with a compound represented by chemical formula 2; and (C) a polymerizable monomer.

[0089] [Chemical Formula 1]

[0090]

[0091] [Chemical Formula 2]

[0092]

[0093] In chemical formula 1 and chemical formula 2,

[0094] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0095] R 2 R 4 R 7 and R 8 Each is independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.

[0096] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0097] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group, and

[0098] L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0099] The embodiments provide a curable composition for displays, and more specifically, a color filter composition containing quantum dots, which has recently become a new technological trend in the display field. By introducing a silicon compound obtained by reacting a compound represented by Chemical Formula 1 with a compound represented by Chemical Formula 2, the curable composition can possess high refractive index, excellent optical properties, and lightfastness.

[0100] The technology for curable compositions containing quantum dots is a previously unknown and emerging concept, and there has been almost no prior research on the relationship and processability between quantum dots and curable compositions. There has been a long-standing need for curable compositions containing quantum dots that can maintain high refractive index, high optical properties, and lightfastness over long periods of time, but this problem has not yet been effectively solved.

[0101] In this invention, in order to simultaneously improve the refractive index, optical properties and lightfastness of ink compositions containing sub-dots, a silicon compound obtained by reacting a compound represented by chemical formula 1 with a compound represented by chemical formula 2 is introduced. More specifically, by mixing the silicon compound with a polymerizable monomer containing a compound with a refractive index greater than or equal to 1.60, the degradation of refractive index, optical properties and lightfastness can be minimized even when inkjet processes are performed for a long time.

[0102] Each component will be explained in detail below.

[0103] (A) Quantum dots

[0104] Quantum dots absorb light in the wavelength range of 360 nm to 780 nm, for example, 400 nm to 780 nm, and emit fluorescence in the wavelength range of 500 nm to 700 nm, for example, 500 nm to 580 nm, or in the wavelength range of 600 nm to 680 nm. That is, quantum dots exhibit the maximum fluorescence emission wavelength (fluorescence λ) in the 500 nm to 680 nm range. em ).

[0105] Quantum dots can each independently have a full width at half maximum (FWHM) of 20 to 100 nanometers, for example, 20 to 50 nanometers. When quantum dots have a full width at half maximum (FWHM) within this range, color reproducibility is increased due to high color purity when used as color materials in color filters.

[0106] Quantum dots can be organic materials, inorganic materials, or mixtures of organic and inorganic materials, each independently.

[0107] Quantum dots can each be independently composed of a core and a shell surrounding the core, and the core and shell can each independently have a core, core / shell, core / first shell / second shell, alloy, alloy / shell, etc., structured as belonging to groups II-IV, III-V, etc., but are not limited to these.

[0108] For example, the core may contain at least one material selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, GaN, GaP, GaAs, InP, InAs, and alloys thereof, but is not limited thereto. The shell surrounding the core may contain at least one material selected from CdSe, ZnSe, ZnS, ZnTe, CdTe, PbS, TiO, SrSe, HgSe, and alloys thereof, but is not limited thereto.

[0109] In this embodiment, due to the recent significant increase in global environmental concerns and the strengthening of constraints on toxic materials, cadmium-free luminescent materials (InP / ZnS) with slightly lower quantum efficiency (quantum yield) but no environmental harm are used to replace luminescent materials with cadmium-based cores, but this is not necessarily the only option.

[0110] The structure of quantum dots is not particularly restricted, but in the case of core / shell structured quantum dots, the size (average particle size) of each quantum dot, including the shell, can be 1 nanometer to 15 nanometers, for example, 5 nanometers to 15 nanometers.

[0111] For example, quantum dots can independently include red quantum dots, green quantum dots, or combinations thereof. Red quantum dots can independently have an average particle size of 10 nanometers to 15 nanometers. Green quantum dots can independently have an average particle size of 5 nanometers to 8 nanometers.

[0112] On the other hand, to achieve dispersion stability of quantum dots, the curable composition according to the embodiments may further include a dispersant. The dispersant contributes to the uniform dispersion of light conversion materials, such as quantum dots, in the curable composition and may include nonionic, anionic, or cationic dispersants. Specifically, the dispersant may be a polyalkylene glycol or its ester, polyoxyolefin, polyol ester epoxide addition product, alcohol epoxide addition product, sulfonate, sulfonate, carboxylic acid ester, carboxylate, alkylamide epoxide addition product, alkylamine, etc., and may be used alone or in mixtures of two or more. The amount of dispersant used may be from 0.1% to 100% by weight, for example, from 10% to 20% by weight, based on the solids content of the light conversion material (e.g., quantum dots).

[0113] For example, quantum dots can be surface-modified using ligands with polar groups (e.g., ligands with high affinity for polymerizable compounds). In the case of surface-modified quantum dots as described above, it is very easy to prepare high-concentration or highly concentrated quantum dot dispersions (improved dispersibility of quantum dots in polymerizable compounds), which can have a significant impact on improving light efficiency and is particularly desirable in the implementation of solvent-free curable compositions.

[0114] For example, ligands with polar groups can have structures that have a high affinity for the chemical structure of polymerizable compounds.

[0115] For example, a ligand with a polar group can be represented by any of the compounds represented by chemical formulas A to Q, but is not necessarily limited to these.

[0116] [Chemical Formula A]

[0117]

[0118] [Chemical Formula B]

[0119]

[0120] [Chemical formula C]

[0121]

[0122] [Chemical formula D]

[0123]

[0124] In chemical formula D, m1 is an integer from 0 to 10.

[0125] [Chemical Formula E]

[0126]

[0127] [Chemical formula F]

[0128]

[0129] [Chemical formula G]

[0130]

[0131] [Chemical formula H]

[0132]

[0133] [Chemical Formula I]

[0134]

[0135] [Chemical Formula J]

[0136]

[0137] [Chemical formula K]

[0138]

[0139] [Chemical formula L]

[0140]

[0141] [Chemical formula M]

[0142]

[0143] [Chemical formula N]

[0144]

[0145] [Chemical formula O]

[0146]

[0147] [Chemical formula P]

[0148]

[0149] [Chemical Formula Q]

[0150]

[0151] Quantum dots may be included in amounts ranging from 5% to 60% by weight, for example, from 10% to 60% by weight, or for example, from 20% to 50% by weight, based on the total amount of the curable composition according to the embodiments. When quantum dots are included within the above range, excellent light conversion efficiency is achieved without compromising patterning and development properties, thus resulting in excellent processability.

[0152] (B) Silicon compounds

[0153] Silicon compounds may include structural units represented by chemical formula 1-1 and structural units represented by chemical formula 2-1.

[0154] [Chemical Formula 1-1]

[0155]

[0156] [Chemical Formula 2-1]

[0157]

[0158] In chemical formulas 1-1 and 2-1,

[0159] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0160] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0161] R 5 and R 6Each is independently a substituted or unsubstituted C6 to C20 aryl group, and

[0162] L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0163] For example, silicon compounds may include structural units represented by chemical formula 4.

[0164] [Chemical Formula 4]

[0165]

[0166] In chemical formula 4,

[0167] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0168] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0169] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0170] L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group, and

[0171] n and m are each an independent integer greater than or equal to 1, with the constraint that n ≥ m.

[0172] For example, a silicon compound can be a compound obtained by further reacting a compound represented by chemical formula 3, in addition to the compounds represented by chemical formula 1 and the compounds represented by chemical formula 2.

[0173] [Chemical Formula 3]

[0174]

[0175] In chemical formula 3,

[0176] R 9 To R 12 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group.

[0177] If a silicon compound is obtained by reacting not only the compound represented by chemical formula 1 with the compound represented by chemical formula 2, but also the compound represented by chemical formula 3, then the silicon compound has a higher refractive index and can have better light efficiency and light resistance reliability compared to a compound obtained by reacting only the compound represented by chemical formula 1 with the compound represented by chemical formula 2.

[0178] For example, silicon compounds may include structural units represented by chemical formula 1-1, structural units represented by chemical formula 2-1, and structural units represented by chemical formula 3-1.

[0179] [Chemical Formula 1-1]

[0180]

[0181] [Chemical Formula 2-1]

[0182]

[0183] [Chemical Formula 3-1]

[0184]

[0185] In chemical formulas 1-1 to 3-1

[0186] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0187] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0188] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0189] R 9 and R 11 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group, and

[0190] L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0191] For example, silicon compounds may include structural units represented by chemical formula 5.

[0192] [Chemical Formula 5]

[0193]

[0194] In chemical formula 5,

[0195] R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group.

[0196] R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.

[0197] R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0198] R 9 and R 11 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group.

[0199] L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group, and

[0200] n, m, and q are each an independent integer greater than or equal to 1, with the constraints that n ≥ m and n > q.

[0201] For example, in chemical formula 5, n = m. In this case, compared to the case where n > m, it can be excellent in terms of optical properties and lightfastness.

[0202] For example, the silicon compound may have a weight average molecular weight of 500 g / mol to 1,500 g / mol, such as 550 g / mol to 1,400 g / mol. In this case, when the weight average molecular weight of the silicon compound is within the above range, patterning can be easily formed without residues when the curable composition is coated and cured, there is no loss of film thickness during development, and good patterning can be obtained.

[0203] The silicon compound may be included in an amount of 10% to 30% by weight, for example, 10% to 25% by weight, based on the total amount of the curable components. When the silicon compound is included within the above range, excellent sensitivity, developability, resolution, and linearity of the pattern can be obtained.

[0204] (C) Polymerizable monomers

[0205] The polymerizable monomer may be a monofunctional or polyfunctional ester of (meth)acrylic acid containing at least one olefinically unsaturated double bond.

[0206] The polymerizable monomers have olefinic unsaturated double bonds, and therefore can be fully polymerized during exposure in the patterning process to form patterns with excellent heat resistance, light resistance and chemical resistance.

[0207] Specific examples of polymerizable monomers include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate. (Meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy (meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tri(meth)acryloyloxyethyl phosphate, phenolic varnish epoxy (meth)acrylate, etc.

[0208] Examples of commercially available polymerizable monomers are as follows. Monofunctional (meth)acrylates may include: Aronix M-101 ® M-111 ® M-114 ® (Toagosei Chemistry Industry Co., Ltd.); KAYARAD TC-110S ® TC-120S ® (Nippon Kayaku Co., Ltd.); V-158 ® and V-2311 ® (Osaka Organic Chemical Ind., Ltd.) etc. Examples of bifunctional (meth)acrylates may include: Yarrow M-210 ® M-240 ® M-6200 ® (Dong-A Synthetic Chemical Co., Ltd.), Kayalade HDDA ® HX-220 ® R-604 ® (Nippon Kayaku Co., Ltd.), V-260 ® V-312 ® V-335 HP ® (Osaka Organic Chemicals Co., Ltd.), etc. Examples of trifunctional (meth)acrylates may include: Yronis M-309. ® M-400 ®M-405 ® M-450 ® M-7100 ® M-8030 ® M-8060 ® (Dong-A Synthetic Chemical Co., Ltd.), Kayara TMPTA ® DPCA-20 ® DPCA-30 ® DPCA-60 ® DPCA-120 ® (Nippon Kayaku Co., Ltd.), V-295 ® V-300 ® V-360 ® V-GPT ® V-3PA ® V-400 ® (Osaka Yuki Kayaku Kogyo Co. Ltd.) etc. These can be used alone or as a mixture of two or more.

[0209] For example, the curable composition containing quantum dots according to the embodiments includes a polymerizable compound with a high refractive index, thereby increasing the refractive index of the composition and simultaneously achieving excellent optical properties. For example, the compound with a high refractive index may be a compound with a refractive index greater than or equal to 1.60.

[0210] Anhydrides can be used to treat polymerizable monomers to improve their developability.

[0211] The polymerizable monomer may be included in amounts ranging from 30% to 95% by weight, for example, 40% to 90% by weight, or for example, 45% to 85% by weight, based on the total amount of the curable component. When the polymerizable monomer is included within the above range, the pattern is fully cured during exposure during the patterning process, thereby achieving excellent reliability, and the heat resistance, light resistance, chemical resistance, resolution, and adhesion of the pattern are also improved.

[0212] (D) Polymerization initiator

[0213] The polymerization initiator can be an initiator commonly used in curable components, and may include, for example, acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, oxime-based compounds, etc.

[0214] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylacetophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinylprop-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-but-1-one, etc.

[0215] Examples of benzophenone compounds include benzoyl benzoate, benzoyl benzoate, benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, benzoyl acrylate, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

[0216] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, etc.

[0217] Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, etc.

[0218] Examples of triazine compounds include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(p-tolyl)-4,6-bis(trichloromethyl)- s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphthol-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthol-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, etc.

[0219] Examples of oxime compounds include O-acyloxime compounds, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethyl ketone, O-ethoxycarbonyl-α-oxyamino-1-phenylprop-1-one, etc. Specific examples of O-acyl oxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-but-1-one, 1-(4-phenylthiophenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylthiophenyl)-octane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylthiophenyl)-octane-1-one-oxime-O-acetate, and 1-(4-phenylthiophenyl)-but-1-one-oxime-O-acetate.

[0220] In addition to the compounds mentioned above, polymerization initiators may also include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, biimidazole compounds, etc.

[0221] Polymerization initiators can be used with photosensitizers that can induce a chemical reaction by absorbing light, become excited, and subsequently transfer their energy.

[0222] Examples of photosensitizers include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, and dipentaerythritol tetra-3-mercaptopropionate.

[0223] The polymerization initiator may be included in an amount from 0.01% to 5% by weight, for example, from 0.1% to 1% by weight, based on the total amount of the curable component. If the polymerization initiator is included within the above range, sufficient curing occurs during exposure in the patterning process to obtain excellent reliability, and the heat resistance, light resistance, chemical resistance, resolution, and adhesion of the pattern are improved, and transmittance degradation due to unreacted initiator can be prevented.

[0224] (E) Dispersant

[0225] The curable composition according to the embodiments may further include a dispersant.

[0226] For example, dispersants may include barium sulfate (BaSO4), calcium carbonate (CaCO3), titanium dioxide (TiO2), zirconium oxide (ZrO2), or combinations thereof.

[0227] The diffusing agent can reflect light that has not been absorbed by the light conversion material and allow the light conversion material to reabsorb the reflected light. That is, the diffusing agent can increase the amount of light absorbed by the light conversion material, thereby increasing the light conversion efficiency of the curable composition.

[0228] The dispersant may have an average particle size (D) of 150 nm to 250 nm, and more specifically 180 nm to 230 nm. 50 If the average particle size of the diffusing agent is within the aforementioned range, it can achieve better light diffusion and improve light conversion efficiency.

[0229] The diffuser may be included in an amount of 0.5% to 10% by weight, for example, 0.5% to 8% by weight, based on the total amount of the curable component. Specifically, this refers to the solid content of the diffuser. If the diffuser is included in an amount of less than 0.5% by weight based on the total amount of the curable component, it is difficult to expect an improvement in light conversion efficiency due to the use of the diffuser. If the diffuser is included in an amount of more than 10% by weight, the pattern characteristics of the color filter may be degraded, and the light conversion efficiency may also be degraded.

[0230] (F) Other additives

[0231] The curable composition according to the embodiments may further include thiol-based additives to improve the stability and dispersibility of quantum dots.

[0232] Thiol-based additives can be substituted on the shell surface of quantum dots to improve the dispersion stability of quantum dots in solvents, thereby stabilizing the quantum dots.

[0233] Thiol-based additives may have 2 to 10, for example 2 to 4 thiol groups (-SH) at the terminal end, depending on their structure.

[0234] For example, thiol-based additives may include at least two functional groups represented by chemical formula 8 at the end.

[0235] [Chemical Formula 8]

[0236]

[0237] In chemical formula 8,

[0238] L 31 and L 41 Each of them is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0239] For example, thiol additives can be represented by chemical formula 8-1.

[0240] [Chemical Formula 8-1]

[0241]

[0242] In chemical formula 8-1,

[0243] L 31 and L 41 Each of them is independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heteroarylene group, and

[0244] u1 and u2 are each an independent integer of 0 or 1.

[0245] For example, in chemical formula 8 and chemical formula 8-1, L 31 and L 41 Each can be a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

[0246] Specific examples of thiol-based additives may include pentaerythritol tetrakis(3-mercaptopropionate) represented by chemical formula 8a, trimethylolpropane tris(3-mercaptopropionate) represented by chemical formula 8b, pentaerythritol tetrakis(mercaptoacetate) represented by chemical formula 8c, trimethylolpropane tris(2-mercaptoacetate) represented by chemical formula 8d, diol di-3-mercaptopropionate represented by chemical formula 8e, and combinations thereof.

[0247] [Chemical Formula 8a]

[0248]

[0249] [Chemical Formula 8b]

[0250]

[0251] [Chemical formula 8c]

[0252]

[0253] [Chemical formula 8d]

[0254]

[0255] [Chemical formula 8e]

[0256]

[0257] The amount of thiol-based additives may be 1% to 10% by weight, for example, 1% to 5% by weight, based on the total amount of the curable components. When thiol-based additives are included within the above range, the stability of light conversion materials such as quantum dots can be improved, and the thiol groups in the components react with the acrylic groups of the resin or monomer to form covalent bonds, thereby improving the heat resistance of light conversion materials such as quantum dots.

[0258] To improve the stability and dispersibility of quantum dots, the curable composition according to the embodiments may further include a polymerization inhibitor.

[0259] Polymerization inhibitors may include, but are not limited to, hydroquinone compounds, catechol compounds, or combinations thereof. If the curable composition according to the embodiments further comprises hydroquinone compounds, catechol compounds, or combinations thereof, room temperature crosslinking during exposure can be prevented after coating the curable composition.

[0260] For example, hydroquinone compounds, catechol compounds, or combinations thereof may be hydroquinone, methylhydroquinone, methoxyhydroquinone, tributylhydroquinone, 2,5-di-tert-butylhydroquinone, 2,5-bis(1,1-dimethylbutyl)hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)hydroquinone, catechol, tributylcatechol, 4-methoxycatechol, gallnutol, 2,6-di-tert-butyl-4-methylphenol, 2-naphthol, tris(N-hydroxy-N-nitrosophenylamino-O,O')aluminum, or combinations thereof, but are not necessarily limited to these.

[0261] Hydroquinone compounds, catechol compounds, or combinations thereof may be used in the form of dispersions. The polymerization inhibitor, in dispersion form, may be included in amounts from 0.001% to 3% by weight, for example, from 0.1% to 2% by weight, based on the total amount of the curable composition. When the polymerization inhibitor is included within this range, aging problems at room temperature can be resolved, while simultaneously preventing sensitivity degradation and surface delamination.

[0262] Additionally, the curable composition according to the embodiments may further include: malonic acid; 3-amino-1,2-propanediol; silane coupling agent; leveling agent; fluorinated surfactant; or combinations thereof, to improve heat resistance and reliability.

[0263] For example, the curable composition according to the embodiments may further include a silane-based coupling agent having reactive substituents such as vinyl, carboxyl, methacryloyloxy, isocyanate, epoxy, etc., to improve adhesion to the substrate.

[0264] Examples of silane-based coupling agents include trimethoxysilylbenzoic acid, γ-methacrylate oxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanate propyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-epoxycyclohexylethyltrimethoxysilane, etc., and these coupling agents can be used alone or in mixtures of two or more.

[0265] Based on 100 parts by weight of curable composition, a silane-based coupling agent can be used in amounts from 0.01 parts by weight to 10 parts by weight. When a silane-based coupling agent is included within this range, the close contact properties, storage capacity, etc., are improved.

[0266] In addition, the curable composition may also include surfactants (such as fluorinated surfactants) as needed to improve coating properties and suppress spot formation, i.e., improve leveling performance.

[0267] Fluorinated surfactants can have a low weight-average molecular weight of 4,000 g / mol to 10,000 g / mol, and more specifically 6,000 g / mol to 10,000 g / mol. Additionally, fluorinated surfactants can have a surface tension of 18 mN / m to 23 mN / m (measured in a 0.1% solution of polyethylene glycol monomethyl ether acetate (PGMEA)). When fluorinated surfactants have a weight-average molecular weight and surface tension within the aforementioned range, leveling performance can be further improved, and when applied as a high-speed slit coating, they provide excellent properties because they can reduce film defects by preventing spot formation and suppressing vapor generation during high-speed coating.

[0268] An example of a fluorinated surfactant is BM-1000. ® and BM-1100 ® (BM Chemie Inc.); MEGAFACE F 142D ® F 172 ® F 173 ®and F 183 ® (Dainippon Ink Kagaku Kogyo Co., Ltd.); FULORAD FC-135 ® Florard FC-170C ® Florard FC-430 ® and Florard FC-431 ® (Sumitomo 3M Co., Ltd.); SURFLON S-112 ® S-113, Shafulong ® S-131, Shafulong ® S-141, Shafulon ® and Shafulong S-145 ® (ASAHI Glass Co., Ltd.); and SH-28PA ® SH-190®, SH-193 ® SZ-6032 ® and SF-8428 ® Examples include Toray Silicone Co., Ltd. and DIC Co., Ltd.'s F-482, F-484, F-478, and F-554.

[0269] In addition to fluorinated surfactants, the curable composition according to the embodiments may include silicone surfactants. Specific examples of silicone surfactants include, but are not limited to, TSF400, TSF401, TSF410, and TSF4440 from Toshiba Silicone Co., Ltd.

[0270] Based on 100 parts by weight of the curable composition, a surfactant may be included in an amount of 0.01 parts by weight to 5 parts by weight, for example, 0.1 parts by weight to 2 parts by weight. If a surfactant is included within this range, less foreign matter will be generated in the sprayed composition.

[0271] In addition, unless it would degrade the properties, the curable composition according to the embodiments may contain other additives, such as antioxidants, stabilizers, etc., in a predetermined amount.

[0272] (G) Solvent

[0273] The curable composition according to the embodiments may be a solvent-free curable composition that does not contain solvents.

[0274] Additionally, the curable composition according to the embodiments may be a solvent-based curable composition containing a solvent. In this case, the solvent may be a material that is compatible with, but does not react with, quantum dots, adhesive resins, polymerizable monomers, polymerization initiators, and other additives described later.

[0275] Examples of solvents compatible with quantum dots, adhesive resins, polymerizable monomers, polymerization initiators, and other additives may include: alcohols, such as methanol and ethanol; ethers, such as dichloroethyl ether, n-butyl ether, diisopentyl ether, methyl phenyl ether, and tetrahydrofuran; ethylene glycol ethers, such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellolytic acetates, such as methyl cellolytic acetate, ethyl cellolytic acetate, and diethyl cellolytic acetate; carbitol, such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates, such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons. Examples of ketones include toluene and xylene; ketones include methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone and methyl-n-pentanone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters include ethyl acetate, n-butyl acetate and isobutyl acetate; lactates include methyl lactate and ethyl lactate; alkoxyacetic esters include methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; alkyl alkoxyacetic esters include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate and ethyl ethoxyacetate; alkyl 3-oxypropionic acid esters include methyl 3-oxypropionic acid and ethyl 3-oxypropionic acid; alkyl 3-alkoxypropionic acid esters... Examples include methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate; alkyl 2-oxypropionates, such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; alkyl 2-alkoxypropionates, such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionates, such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid, such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; esters. Examples include ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate, and methyl 2-hydroxy-3-methylbutyrate; keto esters, such as ethyl pyruvate, and high-boiling solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformaniline, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

[0276] Considering compatibility and reactivity, the following can be used: ethylene glycol ethers, such as ethylene glycol monoethyl ether; ethylene glycol alkyl ether acetates, such as ethyl cellosolve acetate; esters, such as ethyl 2-hydroxypropionate; carbitol, such as diethylene glycol monomethyl ether; propylene glycol alkyl ether acetates, such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate.

[0277] The solvent may be included in the total amount of the solvent-based curable composition, for example, from 5% to 80% by weight, or from 20% to 75% by weight (balance amount). When the solvent is included within the above range, the curable composition has a suitable viscosity, and therefore has excellent processability for manufacturing color filters.

[0278] Another embodiment provides a cured layer produced using the above-described curable composition and a display device including the cured layer.

[0279] One of the methods for producing a cured layer may include: applying the curable composition onto a substrate using an inkjet printing method to form a pattern (S1); and curing the pattern (S2).

[0280] (S1) Forming a pattern

[0281] It is desirable to coat curable components onto a substrate in the range of 0.5 micrometers to 20 micrometers using an inkjet printing method. The inkjet printing method can form patterns by having each nozzle spray a single color and thus repeating the spraying an equal number of times as desired, but the patterns can also be formed by having each inkjet nozzle simultaneously spray the desired number of colors, thus reducing the processing steps.

[0282] (S2) Curing

[0283] The obtained pattern is cured to obtain pixels. In this document, the curing method can be either thermosetting or photocuring. Thermosetting can be performed at a temperature greater than or equal to 100°C, preferably in the range of 100°C to 300°C, and more preferably in the range of 160°C to 250°C. Photocuring may involve irradiation with photochemical rays, such as ultraviolet (UV) rays of 190 nm to 450 nm, or 200 nm to 500 nm. Irradiation is performed using light sources such as mercury lamps, metal halide lamps, or argon lasers with low, high, or ultra-high pressure. X-rays, electron beams, etc., may also be used as needed.

[0284] Other methods for producing a cured layer may include using the aforementioned curable components to produce a cured layer via the following photolithography method.

[0285] (1) Coating and film formation

[0286] A curable composition is coated onto a pre-treated substrate to a desired thickness, such as between 2 and 10 micrometers, using methods such as spin coating, slot coating, roller coating, screen printing, or a coater. The coated substrate is then heated at 70°C to 90°C for 1 to 10 minutes to remove the solvent and form a film.

[0287] (2) Exposure

[0288] After placing a mask of a predetermined shape, the resulting film is irradiated with photochemical rays, such as UV rays of 190 nm to 450 nm or 200 nm to 500 nm, to form the desired pattern. Irradiation is performed using light sources such as mercury lamps, metal halide lamps, or argon lasers with low, high, or ultra-high pressure. X-rays, electron beams, etc., may also be used as needed.

[0289] When using a high-pressure mercury lamp, the exposure process uses a light dose of, for example, 500 mJ / cm² or less (using a 365 nm sensor). However, the light dose can vary depending on the type of each component of the curable composition, their combination ratio, and the dry film thickness.

[0290] (3) Development

[0291] After the exposure process, an alkaline aqueous solution is used to develop the exposed film by dissolving and removing the excess areas other than the exposed parts, thereby forming an image pattern. In other words, when an alkaline developing solution is used, the unexposed areas are dissolved, forming an image color filter pattern.

[0292] (4) Post-processing

[0293] The developed image pattern can be heated again or irradiated with photochemical rays to cure it, so as to achieve excellent qualities in terms of heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength, and storage stability.

[0294] Methods of implementing the present invention

[0295] The invention is described in more detail below with reference to examples. However, these examples should not be construed in any way as limiting the scope of the invention.

[0296] (Preparation of silicon compounds)

[0297] Synthesis example 1

[0298] In a round flask, 86.76 g of methanol was placed, and 14.82 g of vinyltrimethoxysilane, 7.61 g of tetramethyl orthosilicate, and 6.49 g of diphenylsilanediol were added and dissolved. Then, 57.84 g of 1% HCl aqueous solution was added, and the reaction was carried out for 5 hours by heating to 70 °C. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. When the reaction was complete, the product was cooled to room temperature (23 °C), purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to obtain a silicon compound represented by formula A (weight average molecular weight: 767 g / mol).

[0299] [Chemical Formula A]

[0300]

[0301] Synthesis example 2

[0302] 112 g of methanol was placed in a round flask, and 23.43 g of 3-(trimethoxysilyl)propyl acrylate, 7.61 g of tetramethyl orthosilicate, and 6.49 g of diphenylsilanediol were added and dissolved in the solution. 75.1 g of 1% HCl aqueous solution was added, and the reaction was carried out at 70 °C for 5 hours. Subsequently, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. When the reaction was complete, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by chemical formula B (weight average molecular weight: 800 g / mol).

[0303] [Chemical Formula B]

[0304]

[0305] Synthesis example 3

[0306] 132 g of methanol was placed in a round flask, and 14.82 g of vinyltrimethoxysilane, 7.61 g of tetramethyl orthosilicate, and 21.63 g of diphenylsilanediol were added and dissolved. Then, 88.11 g of 1% HCl aqueous solution was added, and the reaction was carried out at 70 °C for 5 hours. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. Upon completion of the reaction, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by formula C (weight average molecular weight: 1,301 g / mol).

[0307] [Chemical formula C]

[0308]

[0309] Synthesis example 4

[0310] 158 g of methanol was placed in a round flask, and 23.43 g of 3-(trimethoxysilyl)propyl acrylate, 7.61 g of tetramethyl orthosilicate, and 21.6 g of diphenylsilanediol were added and dissolved. Then, 105.3 g of 1% HCl aqueous solution was added, and the reaction was carried out at 70 °C for 5 hours. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. Upon completion of the reaction, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by formula D (weight average molecular weight: 1,131 g / mol).

[0311] [Chemical formula D]

[0312]

[0313] Synthesis example 5

[0314] 60 g of methanol was placed in a round flask, and 13.22 g of dimethoxymethylvinylsilane and 6.49 g of diphenylsilanediol were added and dissolved. Then, 39.42 g of 1% HCl aqueous solution was added, and the reaction was carried out for 5 hours by heating to 70 °C. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. When the reaction was complete, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by chemical formula E (weight average molecular weight: 581 g / mol).

[0315] [Chemical Formula E]

[0316]

[0317] Synthesis example 6

[0318] 85 g of methanol was placed in a round flask, and 21.83 g of 3-[dimethoxy(methyl)silyl]propyl acrylate and 6.49 g of diphenylsilanediol were added and dissolved therein. Then, 56.6 g of 1% HCl aqueous solution was added, and the reaction was carried out at 70 °C for 5 hours. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. When the reaction was complete, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by chemical formula F (weight average molecular weight: 921 g / mol).

[0319] [Chemical formula F]

[0320]

[0321] Synthesis Example 7

[0322] 105 g of methanol was placed in a round flask, and 13.22 g of dimethoxymethylvinylsilane and 21.63 g of diphenylsilanediol were added and dissolved. Then, 69.69 g of 1% HCl aqueous solution was added, and the reaction was carried out at 70 °C for 5 hours. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. When the reaction was complete, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by the chemical formula G (weight average molecular weight: 752 g / mol).

[0323] [Chemical formula G]

[0324]

[0325] Synthesis example 8

[0326] 130 g of methanol was placed in a round flask, and 21.83 g of 3-[dimethoxy(methyl)silyl]propyl acrylate and 21.63 g of diphenylsilanediol were added and dissolved. Then, 86.9 g of 1% HCl aqueous solution was added, and the reaction was carried out at 70 °C for 5 hours. Next, 0.9 g of trimethylsilanol was added, and the reaction was carried out for 7 hours. When the reaction was complete, the product was cooled to room temperature, purified using excess dichloromethane and distilled water, and concentrated under reduced pressure to synthesize the silicon compound represented by the chemical formula H (weight average molecular weight: 1,052 g / mol).

[0327] [Chemical formula H]

[0328]

[0329] Preparation of surface-modified quantum dot dispersions

[0330] Preparation Example 1

[0331] After placing a magnetic rod in a three-necked round-bottom flask, a green quantum dot dispersion solution (InP / ZnSe / ZnS, Hansol Chemical; quantum dot solid content 23 wt%) was added. Subsequently, a compound (ligand) represented by the chemical formula Q was added, and the mixture was stirred at 80 °C under a nitrogen atmosphere. When the reaction was complete, the quantum dot reaction solution was cooled to room temperature (23 °C) and then added to cyclohexane to capture the precipitate. The precipitate was separated from the cyclohexane by centrifugation and then thoroughly dried in a vacuum oven for 24 hours, thereby obtaining surface-modified quantum dots.

[0332] The surface-modified green quantum dots were stirred together with a polymerizable compound for 12 hours to obtain a surface-modified quantum dot dispersion (QD solids content: 23% by weight).

[0333] ( Synthesis of the compound represented by chemical formula Q: 100 g of PH-4 (Hannong Chemicals Inc.) was placed in a two-necked round-bottom flask and then completely dissolved in 300 mL of THF. Then, 15.4 g of NaOH and 100 mL of water were added at 0 °C, and the solution was completely dissolved until a clear solution was obtained. A solution prepared by dissolving 73 g of p-toluenesulfonyl chloride in 100 mL of THF was slowly injected into the solution at 0 °C. The injection was carried out for 1 hour, and the resulting mixture was then stirred at room temperature for 12 hours. When the reaction was complete, excess dichloromethane was added, and the mixture was stirred. A saturated solution of NaHCO3 was added for extraction, titration, and water removal. After solvent removal, the residue was dried in a drying oven for 24 hours. 50 g of the dried product was added to a two-necked round-bottom flask and stirred thoroughly with 300 mL of ethanol. Subsequently, 27 g of thiourea was added and dispersed, and then refluxed at 80 °C for 12 hours. Next, an aqueous solution prepared by dissolving 4.4 g of NaOH in 20 mL of water was added, and the mixture was stirred for another 5 hours. Excess dichloromethane was added, followed by stirring and the addition of an aqueous hydrochloric acid solution. Extraction, titration, water removal, and solvent removal were then performed sequentially. Finally, the mixture was dried in a vacuum oven for 24 hours to obtain the compound represented by the chemical formula Q.

[0334] [Chemical Formula Q]

[0335]

[0336] (Preparation of curable components)

[0337] Examples 1 to 9 and Comparative Examples 1 to 6

[0338] Curable compositions of Examples 1 to 9 and Comparative Examples 1 to 6 were prepared using the following components, such that each composition is shown in Tables 1 and 2.

[0339] Specifically, a quantum dot dispersion was weighed and then diluted by mixing the quantum dot dispersion with polymerizable monomers, and each of the silicon compounds was added thereto, followed by stirring for 5 minutes. Subsequently, a photoinitiator was added, followed by a light diffusing agent. The corresponding composition was then stirred for 1 hour, thereby preparing a curable composition.

[0340] (A) Quantum dots

[0341] Surface-modified green quantum dot dispersion prepared by self-preparation Example 1

[0342] (B) Silicon compounds

[0343] (B-1) Silicon compound according to Synthesis Example 1

[0344] (B-2) Silicon compound according to Synthesis Example 2

[0345] (B-3) Silicon compound according to Synthesis Example 3

[0346] (B-4) Silicon compound according to Synthesis Example 4

[0347] (B-5) Silicon compound according to Synthesis Example 5

[0348] (B-6) Silicon compound according to Synthesis Example 6

[0349] (B-7) Silicon compound according to Synthesis Example 7

[0350] (B-8) Silicon compound according to Synthesis Example 8

[0351] (B-9) Dimethoxymethylvinylsilane

[0352] (B-10) 3-(trimethoxysilyl)propyl acrylate

[0353] (B-11) diphenylsilanediol

[0354] (B-12) Tetramethyl orthosilicate

[0355] (C) Polymerizable monomers

[0356] (C-1) HD-002 (Manufacturer: Hannover Chemical Company (Refractive Index: 1.456))

[0357] (C-2) BPF-022 (Manufacturer: Hannover Chemical Company) (Refractive index: 1.60)

[0358] (D) Polymerization initiator

[0359] TPO-L (Polynetron Co., Ltd.)

[0360] (E) Dispersant

[0361] Titanium dioxide (TiO2 solid content 20% by weight, average particle size 200 nm, Iridos Co., Ltd.)

[0362] (Table 1)

[0363] (Unit: weight %)

[0364]

[0365] (Table 2)

[0366] (Unit: weight %)

[0367]

[0368] Evaluate

[0369] (1) Refractive index

[0370] (1) The refractive index of each of the curable compositions according to Examples 1 to 9 and Comparative Examples 1 to 6 was measured at 22°C using a refractometer (R4, METTLER TOLEDO), and the results are shown in Tables 3 and 4.

[0371] (2) Optical properties and light resistance reliability

[0372] Each of the curable compositions of Examples 1 to 9 and Comparative Examples 1 to 6 was formed to a size of 20 mm. A 20 mm single-film sample was used, and the light efficiency was measured using an integrating sphere device (QE-2100, Otsuka Electronics Co., Ltd.) and the luminance as a function of time was measured using an in-line luminance meter (M7000, McScience Co., Ltd.). The results are shown in Tables 3 and 4.

[0373] (Table 3)

[0374]

[0375] (Table 4)

[0376]

[0377] As shown in Tables 3 and 4, the curable compositions according to the embodiments exhibit superior refractive index, light efficiency, and lightfastness reliability compared to the curable compositions of the comparative examples. (In Comparative Examples 3 and 6, light efficiency and lightfastness reliability could not be evaluated due to shape and appearance defects in the single-film samples.)

[0378] Although the invention has been described in conjunction with exemplary embodiments now considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements contained within the spirit and scope of the appended claims. Therefore, the above embodiments should be understood as exemplary and not as limiting the invention in any way.

Claims

1. A curable composition comprising: (A) Quantum dots; (B) Silicon compounds, obtained by reacting a compound represented by Formula 1 with a compound represented by Formula 2; and (C) Polymerizable monomers: [Chemical Formula 1] [Chemical Formula 2] in, In chemical formula 1 and chemical formula 2, R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group. R 2 R 4 R 7 and R 8 Each is independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group. R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group. R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group, and L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

2. The curable composition according to claim 1, wherein The silicon compound comprises structural units represented by chemical formula 1-1 and structural units represented by chemical formula 2-1: [Chemical Formula 1-1] [Chemical Formula 2-1] in, In chemical formulas 1-1 and 2-1, R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group. R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group. R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group, and L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

3. The curable composition according to claim 1, wherein... The silicon compound is obtained by further reacting a compound represented by chemical formula 3, in addition to the compound represented by chemical formula 1 and the compound represented by chemical formula 2. [Chemical Formula 3] in, In chemical formula 3, R 9 To R 12 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group.

4. The curable composition according to claim 3, wherein The silicon compound comprises structural units represented by chemical formula 1-1, structural units represented by chemical formula 2-1, and structural units represented by chemical formula 3-1: [Chemical Formula 1-1] [Chemical Formula 2-1] [Chemical Formula 3-1] in, In chemical formulas 1-1 to 3-1 R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group. R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group. R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group. R 9 and R 11 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group, and L 1 It is a single bond or a substituted or unsubstituted C1 to C20 alkylene group.

5. The curable composition according to claim 2, wherein... The silicon compound comprises structural units represented by chemical formula 4: [Chemical Formula 4] in, In chemical formula 4, R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group. R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group. R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group. L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group, and n and m are each an independent integer greater than or equal to 1, with the constraint that n ≥ m.

6. The curable composition according to claim 4, wherein The silicon compound comprises structural units represented by chemical formula 5: [Chemical Formula 5] in, In chemical formula 5, R 1 It is a substituted or unsubstituted vinyl group or a substituted or unsubstituted (meth)acrylate group. R 3 It is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group. R 5 and R 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group. R 9 and R 11 Each is independently a substituted or unsubstituted C1 to C20 alkoxy group. L 1 It is a single-bonded or substituted or unsubstituted C1 to C20 alkylene group, and n, m, and q are each an independent integer greater than or equal to 1, with the constraints that n ≥ m and n > q.

7. The curable composition according to claim 1, wherein... The silicon compound has a weight-average molecular weight of 500 g / mol to 1,500 g / mol.

8. The curable composition according to claim 1, wherein The polymerizable monomers include compounds with a refractive index greater than or equal to 1.

60.

9. The curable composition according to claim 1, wherein The curable component also includes a dispersant.

10. The curable composition according to claim 9, wherein The dispersant includes barium sulfate, calcium carbonate, titanium dioxide, zirconium oxide, or a combination thereof.

11. The curable composition according to claim 1, wherein The quantum dots are quantum dots that absorb light at a range of 360 nm to 780 nm and emit fluorescence at a range of 500 nm to 700 nm.

12. The curable composition according to claim 1, wherein The curable composition comprises, in total quantity, the curable composition including: 5% to 60% by weight of the quantum dots; 10% to 30% by weight of the silicon compound; and 30% to 80% by weight of the polymerizable monomer.

13. The curable composition according to claim 1, wherein the curable composition further comprises: a polymerization inhibitor; malonic acid; 3-amino-1,2-propanediol; a silane coupling agent; a leveling agent; a fluorinated surfactant; or a combination thereof.

14. A cured layer, produced using a curable composition according to any one of claims 1 to 13.

15. A display device comprising the cured layer according to claim 14.

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