Hardening composition, hardened film manufactured using the composition, color filter including the hardened film, and display device including the color filter

Abstract

(A) A quantum dot and (B) a polymerizable compound, wherein the polymerizable compound contains a product of a thiol-ene reaction between a (meth)acrylate monomer and a thiol monomer, a curable composition, a cured film produced using the curable composition, a color filter including the cured film, and a display device including the color filter are provided.

Description

Technical Field

[0001] The present invention relates to a curable composition, a cured film produced using the composition, a color filter including the cured film, and a display device including the color filter.

Background Art

[0002] In the case of general quantum dots, the solvents dispersed due to the hydrophobic surface characteristics are limited. Therefore, it is a fact that it is difficult to introduce them into polar systems such as binders and curable monomers.

[0003] As an example, even in the case of a quantum dot ink composition that has been actively studied, at an initial stage, even a solvent used in a curable composition having relatively low polarity and high hydrophobicity was dispersed to a certain level. For this reason, it is difficult to include 20% by weight or more of quantum dots with respect to the total amount of the composition, and the light efficiency of the ink cannot be increased to a certain level or more. Even if quantum dots are forcibly added and dispersed to increase the light efficiency, it exceeds the viscosity range in which ink-jetting is possible, and the processability could not be satisfied.

[0004] In addition, a method of reducing the ink solid content by including 50% by weight or more of a solvent with respect to the total amount of the composition to achieve a viscosity range in which ink-jetting is possible has been used. Although this method also provides somewhat satisfactory results in terms of viscosity, it has problems such as nozzle drying due to the volatilization of the solvent during ink-jetting, nozzle clogging, and a decrease in the single film thickness over time after ink-jetting, and has the disadvantage that the thickness deviation after curing becomes severe and it is actually difficult to apply to the process.

[0005] Therefore, the solvent-free type of quantum dot ink that does not contain a solvent is the most preferable form for application in actual processes, and the technology of applying the current quantum dots themselves to a solvent-based composition has already been evaluated to have reached a certain limit.

[0006] As reported so far, in the case of the solvent-based composition that is most preferable for application in actual processes, quantum dots that have not been surface-modified such as ligand substitution are contained in a content of about 20% to 25% by weight based on the total amount of the solvent-based composition. Therefore, it is difficult to increase the light efficiency and absorption rate due to the viscosity limit. On the other hand, as another improvement direction, a method of reducing the quantum dot content and increasing the content of a light diffusing agent (scattering body) has also been tried, but this also cannot improve the problems of sedimentation and low light efficiency.

Summary of the Invention

Problems to be Solved by the Invention

[0007] One embodiment is for providing a curable composition containing quantum dots with excellent quantum dot barrier properties and excellent stability.

[0008] Another embodiment is for providing a cured film manufactured using the curable composition.

[0009] Still another embodiment is for providing a color filter including the cured film.

[0010] Still another embodiment is for providing a display device including the color filter.

Means for Solving the Problems

[0011] One embodiment provides a curable composition containing (A) quantum dots and (B) a polymerizable compound, wherein the polymerizable compound contains a product of a thiol-ene reaction between a (meth)acrylate monomer and a thiol monomer.

[0012] The thiol monomer may be a dithiol monomer.

[0013] The thiol monomer is represented by the following Chemical Formula 1.

[0014]

Chemical Formula

[0015] In Chemical Formula 1, L 1 is an ether linking group ( * -O- * ), a sulfide linking group ( * -S- * ), a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a combination thereof.

[0016] Chemical Formula 1 is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2.

[0017]

Chemical Formula

[0018] In Chemical Formula 1-1, L 2 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

[0019] JPEG2025519359000003.jpg29145

[0020] In Chemical Formula 1-2, L 3 and L 4 are each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, and n is an integer from 0 to 10.

[0021] The (meth)acrylate monomer can include a monomer represented by the following chemical formula 2, a monomer represented by the following chemical formula 3, or a mixture thereof.

[0022]

Chemical formula

[0023] In the above chemical formula 2 and chemical formula 3, R 1 ~R 4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. L 5 ~L 10 are each independently a single bond, an ether linking group ( * -O- * ), a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a divalent fluorene linking group, or a divalent bicyclic linking group.

[0024] The monomer represented by the above chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-4.

[0025]

Chemical formula

[0026] In the above chemical formulas 2-1 to 2-4, R 1 and R 2 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. L 11 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. L 12 and L 13 are each independently an ether linking group ( * -O-* ) or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

[0027] In the above Chemical Formula 3, R 3 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R 4 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and L 9 and L 10 are each independently an ether linking group ( * -O- * ) or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

[0028] The polymerizable compound can include at least one selected from the group consisting of a monomer represented by the following Chemical Formula 4 and a monomer represented by the following Chemical Formula 7.

[0029]

Chemical formula

[0030] In the above Chemical Formulas 4 to 7, Ac is a (meth) acrylate group, L a to L d are each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, R a is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, m is an integer from 0 to 10, p is an integer from 1 to 100, q is an integer from 0 to 5.

[0031] In addition to the product of the thiol-ene reaction between the (meth) acrylate monomer and the thiol monomer, the polymerizable compound can further include a monomer represented by the following Chemical Formula 8.

[0032]

Chem.

[0033] In the above chemical formula 8, R 5 and R 6 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, L 14 and L 16 are each independently a single bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, L 15 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or an ether linking group ( * -O- * ).

[0034] The monomer represented by the above chemical formula 8 can be contained in a content higher than that of the product of the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer.

[0035] The curable composition may have a viscosity of 500 cps to 1100 cps.

[0036] The curable composition may be a solvent-free curable composition.

[0037] The solvent-free curable composition can contain 5% to 60% by weight of the quantum dots and 40% to 95% by weight of the polymerizable compound based on the total amount of the solvent-free curable composition.

[0038] The curable composition can further contain a polymerization initiator, a light diffusing agent, a polymerization inhibitor, or a combination thereof.

[0039] The light diffusing agent can contain barium sulfate, calcium carbonate, titanium dioxide, zirconia, or a combination thereof.

[0040] The curable composition can further contain a solvent.

[0041] The curable composition can contain 1 wt% to 40 wt% of the quantum dots, 1 wt% to 20 wt% of the polymerizable compound, and 40 wt% to 80 wt% of the solvent, based on the total weight of the curable composition.

[0042] The curable composition can further contain malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a fluorine-based surfactant, or a combination thereof.

[0043] Another embodiment provides a cured film produced using the curable composition.

[0044] Still another embodiment provides a color filter including the cured film.

[0045] Still another embodiment provides a display device including the color filter.

[0046] Specific matters of other aspects of the present invention are included in the following detailed description.

Advantages of the Invention

[0047] By introducing a novel oligomer using a thiol-ene reaction, a quantum dot-containing curable composition with excellent dispersibility of quantum dots and high curing degree during UV curing can be provided, which can well form a matrix and has a low viscosity.

Modes for Carrying Out the Invention

[0048] Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example and the present invention is not limited thereby. The present invention is defined only by the scope of the following claims.

[0049] Unless otherwise specified in this specification, "alkyl group" means an alkyl group having 1 to 20 carbon atoms, "alkenyl group" means an alkenyl group having 2 to 20 carbon atoms, "cycloalkenyl group" means a cycloalkenyl group having 3 to 20 carbon atoms, "heterocycloalkenyl group" means a heterocycloalkenyl group having 3 to 20 carbon atoms, "aryl group" means an aryl group having 6 to 20 carbon atoms, "arylalkyl group" means an arylalkyl group having 6 to 20 carbon atoms, "alkylene group" means an alkylene group having 1 to 20 carbon atoms, "arylene group" means an arylene group having 6 to 20 carbon atoms, "alkylarylene group" means an alkylarylene group having 6 to 20 carbon atoms, "heteroarylene group" means a heteroarylene group having 3 to 20 carbon atoms, and "alkoxylene group" means an alkoxylene group having 1 to 20 carbon atoms.

[0050] Unless otherwise specified in this specification, "substituted" means that at least one hydrogen atom is substituted with a substituent such as a halogen atom (F, Cl, Br, I), a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, a nitro group, a cyano group, an amine group, an imino group, an azide group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkenyl group having 2 to 20 carbon atoms, a heterocycloalkynyl group having 2 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a combination thereof.

[0051] Also, unless otherwise specified in this specification, "hetero" means that at least one heteroatom among N, O, S, and P is contained at least once in the chemical formula.

[0052] Unless otherwise specifically mentioned in this specification, "(meth)acrylate" means that it can be both "acrylate" and "methacrylate", and "(meth)acrylic acid" means that it can be both "acrylic acid" and "methacrylic acid".

[0053] Unless otherwise specifically mentioned in this specification, "combination" means mixing or copolymerization.

[0054] Unless otherwise defined in the chemical formulas within this specification, if a chemical bond is not drawn at a position where a chemical bond must be drawn, it means that a hydrogen atom is bonded to that position.

[0055] Unless otherwise specifically mentioned in this specification, "*" means a part that is linked to the same or different atoms or chemical formulas.

[0056] The quantum dot-containing curable composition according to the present invention can disperse quantum dots at a level equal to or higher than that of existing polymerizable compounds and can form a matrix well by UV by introducing the product of the thiol-ene reaction between a (meth)acrylate monomer and a thiol monomer as a polymerizable compound. Furthermore, the curable composition according to one embodiment has a low viscosity, and there is no need to raise the temperature of the head during inkjetting, and there is no risk of issues such as nozzle clogging or poor landing at the head nozzle part due to temperature rise.

[0057] Hereinafter, each component constituting the curable composition according to one embodiment will be specifically described.

[0058] Quantum dots The quantum dots contained in the curable composition according to one embodiment can absorb light in the wavelength range of 360 nm to 780 nm, for example, in the wavelength range of 400 nm to 780 nm, and emit fluorescence at a wavelength range of 500 nm to 700 nm, for example, at 500 nm to 580 nm or emit fluorescence at 600 nm to 680 nm. That is, the quantum dots can have a maximum fluorescence emission wavelength (fluorescence λ em ) in the range of 500 nm to 680 nm.

[0059] The quantum dots can each independently have a full width at half maximum (FWHM) in the range of 20 nm to 100 nm, for example, 20 nm to 50 nm. When the quantum dots have a full width at half maximum within the above range, due to the high color purity, there is an effect of increasing the color reproducibility when used as a color material in a color filter.

[0060] The quantum dots can each independently be an organic substance, an inorganic substance, or a hybrid (mixture) of an organic substance and an inorganic substance.

[0061] The quantum dots can each independently be composed of a core and a shell covering the core, and the core and the shell can each independently have a structure such as a core, a core / shell, a core / first shell / second shell, an alloy, an alloy / shell, etc. composed of II-IV group, III-V group elements, etc., but are not limited thereto.

[0062] For example, the core can contain at least one or more substances selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, GaN, GaP, GaAs, InP, InAs, and alloys thereof, but is not necessarily limited thereto. The shell covering the core can contain at least one or more substances selected from the group consisting of CdSe, ZnSe, ZnS, ZnTe, CdTe, PbS, TiO, SrSe, HgSe, and alloys thereof, but is not necessarily limited thereto.

[0063] In one embodiment, recently, globally, there has been a significant increase in environmental concerns and regulations on toxic substances have been strengthened. Therefore, instead of a luminescent substance having a cadmium-based core, an environmentally friendly non-cadmium-based luminescent material (such as InP / ZnS, InP / ZeSe / ZnS, etc.) with a somewhat lower quantum yield is used, but it is not necessarily limited to these.

[0064] In the case of the quantum dots having the core / shell structure, the size (average particle diameter) of each of the entire quantum dots including the shell may be 1 nm to 15 nm, for example, 5 nm to 15 nm.

[0065] For example, each of the quantum dots can independently include red quantum dots, green quantum dots, or a combination thereof. Each of the red quantum dots can independently have an average particle diameter of 10 nm to 15 nm. Each of the green quantum dots can independently have an average particle diameter of 5 nm to 8 nm.

[0066] On the other hand, for the dispersion stability of the quantum dots, the solvent-free curable composition according to one embodiment further includes a dispersant and can also include quantum dots in the form of a quantum dot dispersion. The dispersant promotes the uniform dispersion of a light conversion substance such as quantum dots in the solvent-free curable composition, and all non-ionic, anionic, or cationic dispersants can be used. Specifically, polyalkylene glycol or its esters, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, carboxylates, alkylamide alkylene oxide adducts, alkylamines, etc. can be used, and these can be used alone or in a mixture of two or more. The dispersant can be used in an amount of 0.1 wt% to 100 wt%, for example, 10 wt% to 20 wt% based on the solid content of a light conversion substance such as quantum dots.

[0067] The quantum dots may be surface-modified with a conventional quantum dot surface-modifying substance (e.g., a thiol-based compound, etc.), or may not be surface-modified.

[0068] The quantum dots may be contained in an amount of 5% to 60% by weight, for example 10% to 60% by weight, for example 20% to 50% by weight, for example 30% to 50% by weight, based on the total amount of the solvent-free curable composition. When the quantum dots (e.g., a quantum dot dispersion) are contained within the above range, high light retention rate and light efficiency can be achieved even after curing.

[0069] For example, in the case of a curable composition containing a solvent according to an embodiment, the quantum dots are contained in an amount of 1% to 40% by weight, for example 3% to 30% by weight, based on the total amount of the curable composition. When the quantum dots are contained within the above range, it has excellent light conversion rate, does not inhibit the pattern characteristics and development characteristics, and can have excellent processability.

[0070] Polymerizable compound Regarding the quantum dot-containing curable compositions (inks) up to now, methods for specializing polymerizable compounds having good compatibility with quantum dots, such as thiol-based binders or monomers, have been developed, and some have been commercialized.

[0071] However, all of the thiol-based monomers developed so far only improve the dispersibility of quantum dots, but have a disadvantage in that the degree of curing during UV curing is low and it is disadvantageous for forming a matrix. Therefore, a technique for surface-modifying quantum dots to improve the dispersibility with the monomer has been developed, but there are cases where the dispersibility of quantum dots rather decreases even when the quantum dots are passivated with a surface-modifying substance, and the problems that the photocuring rate and the residual film rate are not improved still remain unsolved.

[0072] Therefore, the present inventors solved the above-described problems by using, as a polymerizable compound, an oligomer which is a product of a thiol-ene reaction between a (meth)acrylate monomer and a thiol monomer, which is different from existing monomers.

[0073] For example, the thiol monomer may be a dithiol monomer.

[0074] For example, the thiol monomer is represented by the following Chemical Formula 1.

[0075]

Chemical formula

[0076] In Chemical Formula 1, L 1 is an ether linking group ( * -O- * ), a sulfide linking group ( * -S- * ), a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a combination thereof.

[0077] For example, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2.

[0078]

Chemical formula

[0079] In Chemical Formula 1-1, L 2 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

[0080]

Chemical formula

[0081] In Chemical Formula 1-2, L 3 and L 4 are each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, n is an integer from 0 to 10.

[0082] For example, the (meth)acrylate monomer may include, but is not necessarily limited to, a monomer represented by the following Chemical Formula 2, a monomer represented by the following Chemical Formula 3, or a mixture thereof.

[0083]

Chemical formula

[0084] In the Chemical Formula 2 and Chemical Formula 3, R 1 ~R 4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, L 5 ~L 10 are each independently a single bond, an ether linking group ( * -O- * ), a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a divalent fluorene linking group, or a divalent bicyclic linking group.

[0085] The divalent bicyclic includes all of a fused bicyclic, a bridged bicyclic, and a spiro structure.

[0086] For example, the monomer represented by the Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-4, but is not necessarily limited thereto.

[0087] [ka]

[0088] In the above Chemical Formula 2-1 to Chemical Formula 2-4, R 1 and R 2 each independently represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, L 11 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, L 12 and L 13 each independently represents an ether linking group ( * -O- * ) or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

[0089] For example, in the above Chemical Formula 3, R 3 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, R 4 is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, L 9 and L 10 each independently represents an ether linking group ( * -O- * ) or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

[0090] For example, the polymerizable compound may include at least one selected from the group consisting of a monomer represented by the following Chemical Formula 4 to a monomer represented by the following Chemical Formula 7, but is not necessarily limited thereto.

[0091] [ka]

[0092] In the above Chemical Formula 4 to Chemical Formula 7, Ac is a (meth)acrylate group; L a ~L dEach is independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, R a is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, m is an integer from 0 to 10, p is an integer from 1 to 100, q is an integer from 0 to 5.

[0093] In the above chemical formula, Ac means a (meth)acrylate group and is represented by the following chemical formula Ac.

[0094]

Chemical formula

[0095] In the chemical formula Ac, R is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0096] The curable composition according to one embodiment does not use alone a polymerizable compound mainly used in conventional quantum dot-containing curable compositions such as pentaerythritol diacrylate, pentaerythritol triacrylate, dipentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol pentaacrylate, pentaerythritol hexaacrylate, bisphenol A diacrylate, trimethylolpropane triacrylate, novolak epoxy acrylate, etc. By using the product generated by the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer as a polymerizable compound (or a part of the polymerizable compound), a curable composition having a low viscosity, enhancing the dispersibility of quantum dots, forming a good matrix by UV, and having excellent stability can be provided.

[0097] For example, when the curable composition according to one embodiment is a solvent-free curable composition, the polymerizable compound is contained in an amount of 40% to 95% by weight, for example, 40% to 90% by weight, for example, 45% to 85% by weight, for example, 45% to 80% by weight, based on the total amount of the solvent-free curable composition. If the content of the polymerizable compound is within the above range, it is possible to produce a solvent-free curable composition having a viscosity that enables inkjetting, and the quantum dots in the produced solvent-free curable composition can have excellent dispersibility, and the optical properties can also be improved.

[0098] For example, the polymerizable compound can further contain a monomer represented by the following Chemical Formula 8 in addition to the product of the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer.

[0099]

Chemical formula

[0100] In Chemical Formula 8, R 5 and R 6 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, L 14 and L 16 are each independently a single bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, L 15 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or an ether linkage group ( * -O- * ).

[0101] For example, the monomer represented by Chemical Formula 8 can have a molecular weight of 170 g / mol to 1,000 g / mol. When the molecular weight of the monomer represented by Chemical Formula 8 is within the above range, it is advantageous for ink-jetting because it does not inhibit the optical properties of the quantum dots and does not increase the viscosity of the curable composition.

[0102] For example, the monomer represented by the chemical formula 8 is represented by the following chemical formula 8-1 or 8-2, but is not necessarily limited thereto.

[0103]

Chemical formula

[0104] For example, the monomer represented by the chemical formula 8 is contained in a content greater than that of the product of the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer. In this case, according to one embodiment, the curable composition can form a better matrix during UV curing.

[0105] For example, in addition to the product of the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer and the monomer represented by the chemical formula 8, the polymerizable compound may further include ethylene glycol diacrylate, triethylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, dipentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol pentaacrylate, pentaerythritol hexaacrylate, bisphenol A diacrylate, trimethylolpropane triacrylate, novolac epoxy acrylate, ethylene glycol dimethacrylate, triethylene glycol dimethacrylate, propylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, or a combination thereof.

[0106] Further, the curable composition according to one embodiment can further contain monomers generally used in conventional thermosetting or photocurable compositions together with the polymerizable compound. For example, the monomers can further contain oxetane compounds such as bis[1-ethyl(3-oxetanyl)]methyl ether.

[0107] For example, when the curable composition according to one embodiment contains a solvent, the polymerizable compound is contained in an amount of 1% by weight to 20% by weight, 1% by weight to 15% by weight, for example, 5% by weight to 15% by weight, based on the total amount of the curable composition. When the polymerizable compound is contained within the above range, the optical properties of the quantum dots can be improved.

[0108] Light diffusing agent The curable composition according to one embodiment can further contain a light diffusing agent.

[0109] For example, the light diffusing agent can contain barium sulfate (BaSO4), calcium carbonate (CaCO3), titanium dioxide (TiO2), zirconia (ZrO2), or a combination thereof.

[0110] The light diffusing agent reflects light that is not absorbed by the quantum dots described above, so that the reflected light can be absorbed by the quantum dots again. That is, the light diffusing agent can increase the amount of light absorbed by the quantum dots and increase the light conversion efficiency of the curable composition.

[0111] The light diffusing agent has an average particle size (D 50 ) that may be 150 nm to 250 nm, and specifically may be 180 nm to 230 nm. When the average particle size of the light diffusing agent is within the above range, it can have a more excellent light diffusing effect and increase the light conversion efficiency.

[0112] The light diffusing agent may be contained in an amount of 1% by weight to 20% by weight, for example 2% by weight to 15% by weight, for example 3% by weight to 10% by weight, based on the total amount of the curable composition. When the light diffusing agent is contained in an amount of less than 1% by weight based on the total amount of the curable composition, it is difficult to expect the effect of improving the light conversion efficiency by using the light diffusing agent, and when it is contained in an amount exceeding 20% by weight, there is a risk of problems such as precipitation of quantum dots.

[0113] Polymerization initiator The curable composition according to one embodiment may further contain a polymerization initiator, and for example, may contain a photoinitiator, a thermal polymerization initiator, or a combination thereof.

[0114] The photoinitiator is an initiator generally used in photosensitive resin compositions, and for example, acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, oxime-based compounds, aminoketone-based compounds, etc. can be used, but it is not necessarily limited thereto.

[0115] Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloroacetophenone, p-t-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and the like.

[0116] Examples of the benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.

[0117] Examples of the thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, and the like.

[0118] Examples of the benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.

[0119] Examples of the 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, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine, and the like.

[0120] Examples of the oxime-based compounds include O-acyl oxime-based compounds, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(O-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one, etc. Specific examples of the O-acyl oxime-based compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione-2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate, etc.

[0121] Examples of the amino ketone-based compounds include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 (2-Benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1), etc.

[0122] In addition to the above compounds, the photoinitiator may also use carbazole-based compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, biimidazole compounds, etc.

[0123] The photoinitiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light and becoming excited and then transferring its energy.

[0124] Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like.

[0125] Examples of the thermal polymerization initiator include peroxides, specifically, benzoyl peroxide, dibenzoyl peroxide, lauryl peroxide, dilauryl peroxide, di-tert-butyl peroxide, cyclohexane peroxide, methyl ethyl ketone peroxide, hydroperoxides (e.g., tert-butyl hydroperoxide, cumene hydroperoxide), dicyclohexyl peroxydicarbonate, 2,2-azobis(isobutyronitrile), t-butyl perbenzoate, and the like. 2,2'-azobis-2-methylpropionitrile and the like are also included, but are not necessarily limited thereto, and any that are widely known in the art can be used.

[0126] The polymerization initiator may be contained in an amount of 0.1% by weight to 5% by weight, for example, 1% by weight to 4% by weight, based on the total amount of the curable composition. When the polymerization initiator is contained within the above range, curing can occur sufficiently during exposure or heat curing to obtain excellent reliability, and a decrease in transmittance due to unreacted initiator can be prevented, thereby preventing a decrease in the optical properties of the quantum dots.

[0127] Binder resin The curable composition according to one embodiment may further contain a binder resin.

[0128] The binder resin may include an acrylic resin, a cardo resin, an epoxy resin, or a combination thereof.

[0129] The acrylic resin may be a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin containing one or more acrylic repeating units.

[0130] Specific examples of the acrylic binder resin include polybenzyl methacrylate, (meth)acrylic acid / benzyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene copolymer, (meth)acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc., but are not limited thereto, and these may be used alone or in combination of two or more.

[0131] The weight average molecular weight (Mw) of the acrylic resin may be 5,000 g / mol to 15,000 g / mol. When the weight average molecular weight of the acrylic resin is within the above range, it has excellent adhesion to the substrate, good physical and chemical properties, and appropriate viscosity.

[0132] The acid value of the acrylic resin may be 80 mgKOH / g to 130 mgKOH / g. When the acid value of the acrylic resin is within the above range, it has excellent resolution of the pixel pattern.

[0133] The caldo resin can be the one used in a normal curable resin (or photosensitive resin) composition. For example, the one presented in Korean Patent Publication No. 10-2018-0067243 can be used, but it is not limited thereto.

[0134] The cald-based resin can be produced by mixing two or more of, for example, fluorene-containing compounds such as 9,9-bis(4-oxiranylmethoxyphenyl)fluorene, benzene tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutane tetracarboxylic dianhydride, perylene tetracarboxylic dianhydride, tetrahydrofuran tetracarboxylic dianhydride, tetrahydrophthalic anhydride and other anhydride compounds, glycol compounds such as ethylene glycol, propylene glycol, polyethylene glycol, alcohol compounds such as methanol, ethanol, propanol, n-butanol, cyclohexanol, benzyl alcohol, solvent compounds such as propylene glycol methyl ethyl acetate, N-methylpyrrolidone, phosphorus compounds such as triphenylphosphine, and amine or ammonium salt compounds such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, benzyltriethylammonium chloride.

[0135] The weight average molecular weight of the cald-based resin may be 500 g / mol to 50,000 g / mol, for example, 1,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the cald-based resin is within the above range, pattern formation can be well performed without residue during the production of the cured film, there is no loss of film thickness during the development of the solvent-based curable composition, and a good pattern can be obtained.

[0136] When the binder resin is a cald-based resin, the curable composition containing the same, particularly the photosensitive resin composition, is excellent in developability, has good sensitivity during photocuring, and is excellent in fine pattern formability.

[0137] The epoxy resin is a monomer or oligomer polymerized by heat and can contain compounds having a carbon-carbon unsaturated bond and a carbon-carbon cyclic bond.

[0138] Examples of the epoxy resin include, but are not necessarily limited to, bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cycloaliphatic epoxy resin, and aliphatic polyglycidyl ether.

[0139] Examples of commercially available products of such compounds include YX4000, YX4000H, YL6121H, YL6640, YL6677 manufactured by Yuka Shell Epoxy Co., Ltd., which are bisphenol epoxy resins; EOCN (registered trademark)-102, EOCN (registered trademark)-103S, EOCN (registered trademark)-104S, EOCN (registered trademark)-1020, EOCN (registered trademark)-1025, EOCN (registered trademark)-1027 manufactured by Nippon Kayaku Co., Ltd., which are cresol novolak type epoxy resins; and Epicoat (registered trademark) 180S75 manufactured by Yuka Shell Epoxy Co., Ltd.; Epicoat (registered trademark) 1001, 1002, 1003, 1004, 1007, 1009, 1010, and 828 manufactured by Yuka Shell Epoxy Co., Ltd., which are bisphenol A type epoxy resins; Epicoat (registered trademark) 807 and 834 manufactured by Yuka Shell Epoxy Co., Ltd., which are bisphenol F type epoxy resins; Epicoat (registered trademark) 152, 154, 157H65 manufactured by Yuka Shell Epoxy Co., Ltd., and EPPN (registered trademark) 201, 202 manufactured by Nippon Kayaku Co., Ltd., which are phenol novolak type epoxy resins; and other cycloaliphatic epoxy resins such as CY175, CY177, and CY179 manufactured by CIBA-GEIGY A.G; ERL-4234, ERL-4299, ERL-4221, and ERL-4206 manufactured by U.C.C; Shodain 509 manufactured by Showa Denko K.K.; Araldite (registered trademark) CY-182, CY-192, and CY-184 manufactured by CIBA-GEIGY A.G; Epiron 200 and 400 manufactured by Dainippon Ink and Chemicals, Inc.; Epicoat (registered trademark) 871, 872, and EP1032H60 manufactured by Yuka Shell Epoxy Co., Ltd.; ED-5661 and ED-5662 manufactured by Celanese Coating Co., Ltd.; Epicoat (registered trademark) 190P and 191P manufactured by Yuka Shell Epoxy Co., Ltd., which are aliphatic polyglycidyl ethers; Epolite 100MF manufactured by Kyoeisha Yushi Kagaku Kogyo Co., Ltd.; Epiole TMP manufactured by NOF Corporation, etc.

[0140] For example, when the curable composition according to an embodiment is a solventless curable composition, the binder resin may be contained in an amount of 0.5% to 10% by weight, for example, 1% to 5% by weight based on the total amount of the curable composition. In this case, the heat resistance and chemical resistance of the solventless curable composition can be improved, and the storage stability of the composition can also be improved.

[0141] For example, when the curable composition according to an embodiment is a curable composition containing a solvent, the binder resin may be contained in an amount of 1% to 30% by weight, for example, 3% to 20% by weight based on the total amount of the curable composition. In this case, excellent pattern properties, heat resistance, and chemical resistance can be improved.

[0142] Other additives In order to improve the stability and dispersibility of the quantum dots, the curable composition according to an embodiment may further contain a polymerization inhibitor.

[0143] The polymerization inhibitor may include, but is not necessarily limited to, hydroquinone-based compounds, catechol-based compounds, or combinations thereof. By the curable composition according to an embodiment further containing the hydroquinone-based compound, the catechol-based compound, or a combination thereof, crosslinking at room temperature can be prevented during exposure after printing (coating) the curable composition.

[0144] For example, the hydroquinone-based compound, catechol-based compound, or a combination thereof may include hydroquinone, methylhydroquinone, methoxyhydroquinone, t-butylhydroquinone, 2,5-di-t-butylhydroquinone, 2,5-bis(1,1-dimethylbutyl)hydroquinone, 2,5-bis(1,1,3,3-tetramethylbutyl)hydroquinone, catechol, t-butylcatechol, 4-methoxyphenol, pyrogallol, 2,6-di-t-butyl-4-methylphenol, 2-naphthol, tris(N-hydroxy-N-nitrosophenylaminato-O,O’)aluminium, or a combination thereof, but is not necessarily limited thereto.

[0145] The hydroquinone-based compound, catechol-based compound, or a combination thereof can be used in the form of a dispersion, and the polymerization inhibitor in the form of the dispersion may be contained in an amount of 0.001% to 3% by weight, for example, 0.1% to 2% by weight, based on the total amount of the curable composition. When the polymerization inhibitor is contained within the above range, problems over time at room temperature can be solved, and at the same time, a decrease in sensitivity and a surface peeling phenomenon can be prevented.

[0146] Also, the curable composition according to one embodiment may further include malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a fluorosurfactant, or a combination thereof in order to improve heat resistance and reliability.

[0147] For example, the curable composition according to one embodiment may further include a silane coupling agent having a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, an epoxy group, etc. in order to improve adhesion to a substrate and the like.

[0148] Examples of the silane coupling agent include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-epoxycyclohexylethyltrimethoxysilane, etc., and these can be used alone or in admixture of two or more thereof.

[0149] The silane coupling agent may be contained in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the curable composition. When the silane coupling agent is contained within the above range, excellent adhesion, storage stability, etc. can be obtained.

[0150] In addition, the curable composition may further contain a surfactant, for example, a fluorosurfactant, as necessary for improving coating properties and preventing the generation of defects, that is, for improving leveling performance.

[0151] The fluorosurfactant can have a low weight average molecular weight of 4,000 g / mol to 10,000 g / mol, and specifically can have a weight average molecular weight of 6,000 g / mol to 10,000 g / mol. Further, the fluorosurfactant may have a surface tension of 18 mN / m to 23 mN / m (measured in a 0.1% propylene glycol monomethyl ether acetate (PGMEA) solution). When the weight average molecular weight and the surface tension of the fluorosurfactant are within the above ranges, the leveling performance can be further improved, bleeding during high speed coating can be prevented, the generation of bubbles is small, and the number of film defects is small, thus imparting excellent characteristics to slit coating, which is a high speed coating method.

[0152] Examples of the fluorosurfactant include BM-1000 (registered trademark), BM-1100, etc. manufactured by BM Chemie, Megafac (registered trademark) F 142D (registered trademark), F 172, F 173, F 183, etc. manufactured by Dainippon Ink and Chemicals, Inc., Fluorad FC-135, FC-170C, FC-430, FC-431, etc. manufactured by Sumitomo 3M Limited, Surflon (registered trademark) S-112 (registered trademark), S-113, S-131, S-141, S-145, etc. manufactured by Asahi Glass Co., Ltd., SH-28PA, -190, -193, SZ-6032, SF-8428, etc. manufactured by Toray Silicone Co., Ltd., and fluorosurfactants commercially available under the names of F-482, F-484, F-478, F-554, etc. manufactured by DIC Corporation can be used.

[0153] In addition, a curable composition according to an embodiment may also use a silicone surfactant together with the above-described fluorosurfactant. Specific examples of the silicone surfactant include TSF400, TSF401, TSF410, TSF4440, etc. manufactured by Toshiba Silicone Co., Ltd., but are not limited thereto.

[0154] The surfactant including the fluorosurfactant etc. may be contained in an amount of 0.01 to 5 parts by weight, for example, 0.1 to 2 parts by weight with respect to 100 parts by weight of the curable composition. When the surfactant is contained within the above range, the phenomenon of foreign matter generation in the sprayed composition is suppressed.

[0155] In addition, a curable composition according to an embodiment may further add a certain amount of other additives such as an antioxidant within a range that does not inhibit the physical properties.

[0156] Solvent On the other hand, a curable composition according to an embodiment may further contain a solvent.

[0157] Examples of the solvent include alcohols such as methanol and ethanol; glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, and propylene glycol methyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols 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 monomethyl ether acetate and propylene glycol propyl ether acetate; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactic acid alkyl esters such as methyl lactate and ethyl lactate; hydroxyacetic acid alkyl esters such as methyl hydroxyacetate, ethyl hydroxyacetate, and butyl hydroxyacetate; alkoxyalkyl acetates such as methoxymethyl acetate, methoxyethyl acetate, methoxybutyl acetate, ethoxymethyl acetate, and ethoxyethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, and propyl 2-hydroxypropionate; 2-methoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, and ethyl 2-ethoxypropionate,Alkyl 2-alkoxypropionates such as methyl 2-ethoxypropionate, alkyl 2-hydroxy-2-methylpropionates such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate, alkyl 2-alkoxy-2-methylpropionates such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate, esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate, and methyl 2-hydroxy-3-methylbutanoate, or keto acid esters such as ethyl pyruvate, and there are also compounds such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc., but not limited thereto.

[0158] For example, it is preferable to use glycol ethers such as ethylene glycol monoethyl ether and ethylene diglycol methyl ethyl ether, ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate, esters such as ethyl 2-hydroxypropionate, carbitols such as diethylene glycol monomethyl ether, propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate, alcohols such as ethanol, or combinations thereof.

[0159] For example, the solvent may be a polar solvent including propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, ethanol, ethylene glycol dimethyl ether, ethylene diglycol methyl ethyl ether, diethylene glycol dimethyl ether, 2-butoxyethanol, N-methylpyrrolidine, N-ethylpyrrolidine, propylene carbonate, γ-butyrolactone, or a combination thereof.

[0160] The solvent may be included in an amount of 40% to 80% by weight, for example, 45% to 80% by weight, based on the total amount of the curable composition. When the solvent is included within the above range, the solvent-based curable composition can exhibit excellent coating properties during spin coating and large-area coating using a slit due to having an appropriate viscosity.

[0161] Another embodiment provides the curable composition, for example, a cured film produced using the curable composition, a color filter including the cured film, and a display device including the color filter.

[0162] One of the methods for manufacturing the cured film includes a step (S1) of applying the curable composition onto a substrate by an inkjet spraying method to form a pattern, and a step (S2) of curing the pattern.

[0163] (S1) Step of forming a pattern The curable composition is preferably applied onto the substrate with a thickness of 0.5 to 20 μm by an inkjet dispersion method. In the inkjet spraying, a pattern can be formed by spraying only a single-color curable composition per nozzle and repeatedly spraying the curable composition according to the number of required colors, or a pattern can also be formed by spraying the curable compositions of the number of required colors simultaneously through each inkjet nozzle in order to reduce the process.

[0164] (S2) Step of curing By curing the remembered pattern, pixels can be obtained. At this time, as the curing method, all of the thermal curing process or the photo-curing process can be applied. In the thermal curing process, it is preferable to heat and cure at a temperature of 100 °C or higher, more preferably, it can be cured by heating at 100 °C to 300 °C, and even more preferably, it can be cured by heating at 160 °C to 250 °C. In the photo-curing process, actinic rays such as UV rays of 190 nm to 450 nm, for example, 200 nm to 500 nm are irradiated. As the light source used for irradiation, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, an argon gas laser, etc. can be used, and in some cases, X-rays, electron beams, etc. can also be used as actinic rays.

[0165] Still another of the methods for producing the cured film is to produce a cured film using a lithography method with the curable composition, and the production method is as follows.

[0166] (1) Coating and coating film formation stage The curable composition is applied on a substrate that has been subjected to predetermined pretreatment using a method such as spin coating, slit coating, roll coating, screen printing, or applicator method to a desired thickness, for example, a thickness of 2 μm to 10 μm, and then heated at a temperature of 70 °C to 90 °C for 1 minute to 10 minutes to remove the solvent to form a coating film.

[0167] (2) Exposure stage After passing a mask of a predetermined shape for pattern formation on the obtained coating film, actinic rays such as UV rays of 190 nm to 450 nm, for example, 200 nm to 500 nm are irradiated. As the light source used for irradiation, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, an argon gas laser, etc. can be used, and in some cases, X-rays, electron beams, etc. can also be used as actinic rays.

[0168] The exposure amount varies depending on the type, blending amount of each component of the curable composition, and the thickness of the dry film. For example, when using a high-pressure mercury lamp, 500 mJ / cm2 The following is (by a 365 nm sensor).

[0169] (3) Development stage Following the exposure stage, an alkaline aqueous solution is used as a developer to dissolve and remove unnecessary portions, leaving only the exposed portions to form an image pattern. That is, by developing with an alkaline developer, the unexposed portions are dissolved and an image color filter pattern is formed.

[0170] (4) Post-treatment stage Regarding the image pattern obtained by the development, in order to obtain a pattern excellent in terms of heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength, storage stability, etc., it can be reheated or irradiated with actinic rays to be cured.

[0171] Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are merely preferred embodiments of the present invention, and the present invention is not limited by the following examples.

Example

[0172] (Synthesis of polymerizable compound) [Synthesis Example 1: Synthesis of compound represented by chemical formula A]

[0173]

Chem.

[0174] After dissolving 546 g of ethoxylated bisphenyl fluorene diacrylate in 500 ml of THF, 2 g of triethylamine was added. Then, 45 g of 1,2-ethanedithiol was slowly added, and the temperature was raised to 60 °C to obtain the compound (Mw = 1148) represented by the chemical formula (A).

[0175] [Synthesis Example 2: Synthesis of compound represented by chemical formula B]

[0176] [Chemistry]

[0177] The compound (Mw = 887) represented by the chemical formula (B) was obtained in the same manner as in Synthesis Example 1, except that 304 g of tricyclodecane dimethanol diacrylate was used instead of ethoxylated bisphenyl fluorene diacrylate.

[0178] [Synthesis Example 3: Synthesis of the compound represented by chemical formula C]

[0179] [Chemistry]

[0180] The compound (Mw = 1937) represented by the chemical formula (C) was obtained in the same manner as in Synthesis Example 1, except that 468 g of ethoxylated bisphenol A diacrylate was used instead of ethoxylated bisphenyl fluorene diacrylate.

[0181] [Synthesis Example 4: Synthesis of the compound represented by chemical formula D]

[0182] [Chemistry]

[0183] The compound (Mw = 1102) represented by the chemical formula (D) was obtained in the same manner as in Synthesis Example 1, except that 226 g of 1,6 - hexanediol diacrylate was used instead of ethoxylated bisphenyl fluorene diacrylate.

[0184] (Production of the curable composition) Based on the following components, curable compositions according to Examples 1 to 6, Comparative Example 1, and Comparative Example 2 were produced.

[0185] (A) Quantum dots (A-1) Green quantum dots (InP / ZnSe / ZnS, manufactured by Hansol Chemical Co., Ltd.) (A-2) Red quantum dots (InP / ZnSe / ZnS, manufactured by Hansol Chemical Co., Ltd.)

[0186] (B) Polymerizable compound (B-1) Compound represented by the following Chemical Formula 8-2 (M200, manufactured by Ajinomoto Fine-Techno Co., Inc.)

[0187] [Chemical formula]

[0188] (B-2) Pentaerythritol hexamethacrylate (DPHA, manufactured by Nippon Kayaku Co., Ltd.) (B-3) Polymerizable compound of Synthesis Example 1 (B-4) Polymerizable compound of Synthesis Example 2 (B-5) Polymerizable compound of Synthesis Example 3 (B-6) Polymerizable compound of Synthesis Example 4 (B-7) Acrylic binder resin (SM-CRB-400H, manufactured by Sumitomo Chemical Co., Ltd.) (B-8) Polysilsesquioxane (manufactured by Arakawa Chemical Industries, Ltd., SQ506)

[0189] (C) Photoinitiator TPO-L (manufactured by Poly-Nitro Co., Ltd.)

[0190] (D) Light diffusing agent Titanium dioxide dispersion (rutile type TiO2; D50 (180 nm), solid content 50 wt%, manufactured by Iridos Co., Ltd.)

[0191] Examples 1 to 6, Comparative Example 1, and Comparative Example 2 Specifically, the quantum dots and the polymerizable compound were mixed and stirred for 12 hours. After adding a photoinitiator thereto, a light diffusing agent was then added.

[0192] The specific composition is shown in Table 1 below.

[0193] [Table 1]

[0194] Evaluation Using 2 mL of each of the curable compositions according to Examples 1 to 6, Comparative Example 1, and Comparative Example 2, spin coating was performed on a glass substrate at 1,500 rpm, and then the initial blue light conversion rate of the QD film formed by exposing with a nitrogen UV exposure apparatus at 5 J for 9 seconds was measured with a light efficiency measuring apparatus (QE-2100, manufactured by Otsuka Corporation). After baking the substrate on which the QD film was formed on a hotplate at 180 °C for 30 minutes in a nitrogen atmosphere, it was cooled at room temperature (23 °C) for 3 hours. Then, after measuring the blue light conversion rate again with a light efficiency measuring apparatus, the heat process retention rate (%) was calculated according to the following calculation formula. Heat process retention rate (%) = [Light conversion rate (after baking) / Initial light conversion rate] * 100

[0195] Also, the viscosity of the curable composition was measured at 25 °C using a viscometer (DV-II, RV-2 spindle, 23 rpm, manufactured by Brookfield). The results are shown in Table 2 below.

[0196] [Table 2]

[0197] From Table 2 above, it was confirmed that the curable compositions according to Examples 1 to 6 were superior in heat resistance reliability, with the decrease in the heat process retention rate suppressed even after the heat curing process, compared to the curable compositions according to Comparative Example 1 and Comparative Example 2. Also, since the viscosity was not too high, it was found that inkjetting could be smoothly performed even at room temperature.

[0198] The present invention is not limited to the above-described embodiments and can be implemented in various different forms. Those having ordinary knowledge in the technical field to which the present invention pertains can understand that it can be implemented in other specific forms without changing the technical idea and essential features of the present invention. Therefore, it must be understood that the above-described embodiments are illustrative in all respects and not restrictive.

Claims

1. (A) a quantum dot, and (B) a polymerizable compound, The polymerizable compound contains a product of a thiol-ene reaction between a (meth)acrylate monomer and a thiol monomer, and is a curable composition.

2. The curable composition according to claim 1, wherein the thiol monomer is a dithiol monomer.

3. The thiol monomer is represented by the following Chemical Formula 1, 【Chemical 1】 In the Chemical Formula 1, L １ is an ether linking group ( ＊ -O- ＊ ), a sulfide linking group ( ＊ -S- ＊ ), a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a combination thereof, and the curable composition according to claim 1.

4. The Chemical Formula 1 is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2, [Chemical Formula 2] In the Chemical Formula 1-1, L ２ is an alkylene group having 1 to 20 carbon atoms which may be substituted or unsubstituted, 【Chemical Formula 3】 In the Chemical Formula 1-2, L ３ and L ４ are each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, The curable composition according to claim 3, wherein n is an integer of 0 to 10.

5. The (meth)acrylate monomer contains a monomer represented by the following Chemical Formula 2, a monomer represented by the following Chemical Formula 3, or a mixture thereof, 【Chemical Formula 4】 In the Chemical Formula 2 and Chemical Formula 3, R １ to R ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, L ５ ~L １０ are each independently a single bond, an ether linking group ( ＊ -O- ＊ ), a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a divalent fluorene linking group, or a divalent bicyclic linking group, the curable composition according to claim 1.

6. The monomer represented by the Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-4, [Chemical Formula 5] In the Chemical Formulas 2-1 to 2-4, R １ and R ２ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, L １１ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, L １２ and L １３ are each independently an ether linking group ( ＊ -O- ＊ ), or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, the curable composition according to claim 5.

7. In the Chemical Formula 3, R ３ is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R ４ is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, L ９ and L １０ each independently represents an ether linking group ( ＊ -O- ＊ ), or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, the curable composition according to claim 5.

8. The polymerizable compound contains at least one selected from the group consisting of a monomer represented by the following Chemical Formula 4 to a monomer represented by the following Chemical Formula 7 [Chemical Formula 6] In the Chemical Formulas 4 to 7, Ac is a (meth)acrylate group, L ａ ~L ｄ are each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, R ａ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, m is an integer of 0 to 10, p is an integer of 1 to 100, q is an integer of 0 to 5, and the curable composition according to claim 1.

9. The polymerizable compound further contains a monomer represented by the following Chemical Formula 8 in addition to the product of the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer, 【Chemical Formula 6】 In the Chemical Formula 8, R ５ and R ６ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, L １４ and L １６ each independently represents a single bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, L １５ is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or an ether linking group ( ＊ -O- ＊ ), the curable composition according to claim 1.

10. The curable composition according to claim 9, wherein the monomer represented by the Chemical Formula 8 is contained in a content higher than that of the product of the thiol-ene reaction between the (meth)acrylate monomer and the thiol monomer.

11. The curable composition according to claim 1 has a viscosity of 500 cps to 1100 cps.

12. The curable composition according to claim 1 is a solvent-free curable composition.

13. The solvent-free curable composition is based on the total amount of the solvent-free curable composition, The quantum dot is contained in an amount of 5% by weight to 60% by weight, and The polymerizable compound is contained in an amount of 40% by weight to 95% by weight, and the solvent-free curable composition according to claim 12.

14. The curable composition according to claim 1, further comprising a polymerization initiator, a light diffusing agent, a polymerization inhibitor, or a combination thereof.

15. The curable composition according to claim 14, wherein the light diffusing agent comprises barium sulfate, calcium carbonate, titanium dioxide, zirconia, or a combination thereof.

16. The curable composition according to claim 1, further comprising a solvent.

17. The curable composition according to claim 16, wherein the curable composition contains 1 wt% to 40 wt% of the quantum dots, 1 wt% to 20 wt% of the polymerizable compound, and 40 wt% to 80 wt% of the solvent, based on the total weight of the curable composition.

18. The curable composition according to claim 1, further comprising malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a fluorine-based surfactant, or a combination thereof.

19. A cured film produced using the curable composition according to any one of claims 1 to 18.

20. A color filter comprising the cured film according to claim 19.

21. A display device comprising the color filter according to claim 20.

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