TWI676668B - Curable composition containing quantum dots, color filter manufactured by the same, and image display device - Google Patents

Abstract

An object of the present invention is to provide a curable composition containing quantum dots, in which quantum dot particles are uniformly dispersed, and there are no problems such as a decrease in light efficiency and poor photosensitivity characteristics during the manufacturing process of a color filter, so that excellent color filters can be manufactured. Device. Another object of the present invention is to provide a color filter manufactured from such a curable composition containing a quantum dot and an image display device including the color filter.

Description

Curable composition containing quantum dots, color filter manufactured using the same, and image display device

The present invention relates to a curable composition containing quantum dots, a color filter manufactured using the same, and an image display device.

A color filter is a thin film film type optical component that can extract three colors of red, green, and blue from white light to form a fine pixel unit. The size of a pixel is about tens to hundreds of microns. This type of color filter has a black matrix layer formed by a predetermined pattern on a transparent substrate in order to shield the boundary portion between pixels, and a plurality of colors (typically red (R), green ( G) and blue (B) 3 primary colors) in which pixel portions arranged in a predetermined order are sequentially stacked. Generally, a color filter can be manufactured by coating three or more colors on a transparent substrate by a dyeing method, an electrodeposition method, a printing method, or a pigment dispersion method. Recently, pigments of a pigment-dispersed photosensitive resin are used. Decentralized methods have become mainstream.

One of the methods for implementing a color filter is a method of forming a colored film by repeating a series of processes including a colorant and an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, and a ring. The photosensitive resin composition of oxygen resin, solvent, and other additives is coated on a transparent substrate provided with a black matrix. After exposing the pattern in the form to be formed, the non-exposed parts are removed with a solvent and thermally cured. It is widely used in the manufacture of LCDs for mobile phones, notebook computers, monitors, televisions, etc. In recent years, the actual situation is that for a photosensitive resin composition for a color filter using a pigment dispersion method having various advantages, not only excellent pattern characteristics but also high color reproduction rate and High brightness and high contrast have further improved performance.

However, color reproduction is achieved by a light-transmitting filter irradiated from a light source. In the process, a part of the light is absorbed by the color filter, so the light efficiency is reduced. In addition, due to the characteristics of the pigment as a color filter, there is Fundamental limitations such as insufficient color reproduction.

In addition, Korean Patent Laid-Open Publication No. 10-2013-0000506 discloses a display device including a light source and a display panel into which light emitted from the light source is incident. The display panel includes a plurality of color conversion sections. The color conversion section includes A plurality of wavelength-converting particles that convert the wavelength of the light and a plurality of color filter particles that absorb light of a predetermined wavelength band in the light.

However, although the above-mentioned conventional technology is similar in terms of including quantum dots, the content of the photosensitive resin composition is not specifically described, and only a display device having high color reproduction rate and brightness is disclosed. Therefore, it is necessary to perform the photosensitive resin composition Additional development.

Prior art literature Patent literature

Patent Document 1: Korean Patent Publication No. 10-2013-0000506

An object of the present invention is to provide a curable composition containing quantum dots, which can uniformly disperse quantum dot particles, and does not have problems such as a decrease in light efficiency and poor photosensitivity characteristics in a color filter manufacturing process, and can produce excellent Color filter.

Another object of the present invention is to provide a color filter manufactured from such a curable composition containing quantum dots and an image display device including the same.

In order to achieve the above object, the curable composition containing a quantum dot according to an embodiment of the present invention includes a binder and a quantum dot, and the binder includes the following Chemical Formula 1, Chemical Formula 2 and More than one of the combinations.

基，R₃表示C1~C30伸烷基、C1~C30伸烷基氧基或C1~C30乙基氧基羰基胺基乙基，R₄表示含有不飽和雙鍵之基團。) (In the above Chemical Formula 1, R ₁ represents hydrogen or C1-C6 alkyl, and R ₂ represents oxygen, -NH- or

R ₃ represents a C1 to C30 alkylene group, C1 to C30 alkyleneoxy group, or C1 to C30 ethyloxycarbonylaminoethyl group, and R ₄ represents a group containing an unsaturated double bond. )

基，R₈表示C1~C30伸烷基、C1~C30伸烷基氧基或C1~C30乙基氧基羰基胺基乙基，R₉表示含有不飽和雙鍵之基團，X表示0<X<100之值。) (In the above Chemical Formula 2, R ₅ to R ₆ are each independently the same or different from each other, and represent hydrogen or a C 1 to C 6 alkyl group, and R ₇ represents oxygen, -NH- or

R ₈ represents C1 ~ C30 alkylene, C1 ~ C30 alkyleneoxy or C1 ~ C30 ethyloxycarbonylaminoethyl, R ₉ represents a group containing an unsaturated double bond, and X represents 0 < The value of X <100. )

As described above, the curable composition containing a quantum dot of the present invention contains an adhesive of a specific compound, and thus has the effect of providing a high-quality color filter excellent in color reproducibility and brightness characteristics.

In addition, the present invention is capable of providing a curable composition containing the quantum dots. The effect of the manufactured color filter and the image display device including the same.

The curable composition containing a quantum dot of the present invention includes a binder and a quantum dot, and the binder is characterized by the following Chemical Formula 1 or Chemical Formula 2.

In addition, the curable composition containing the quantum dots of the present invention can further contain an o-naphthoquinonediazide compound in the case of a positive structure in addition to the binder and the quantum dots described above. In this case, a monomer or oligomer having one or more ethylenically unsaturated groups can be further contained. If necessary, it may further contain other components, such as a crosslinking agent. In the case of the positive structure, the monomer, oligomer, or photopolymerization initiator may be further contained.

First, the curable composition containing the quantum dots of the present invention can include the adhesive of Chemical Formula 1, and the glass transition temperature can be -20 to 250 ° C. In this case, the adhesive is a copolymer having a polymerizable side chain.

In the above Chemical Formula 1, R ₁ represents hydrogen or a C1-C6 alkyl group. More preferably, R ₁ can be freely selected in consideration of film strength, elastic modulus, viscoelasticity, heat resistance, developability, glass transition temperature (Tg) of polymer, solubility, suitability for synthesis, and the like.

基。更佳地，R₂能夠考慮膜之強度、彈性模數、黏彈性、耐熱性、顯影性、合成適合性、聚合物之玻璃化轉變溫度(Tg)、溶解性等而自由選擇。 R ₂ represents oxygen, -NH- or

base. More preferably, R ₂ can be freely selected in consideration of film strength, elastic modulus, viscoelasticity, heat resistance, developability, synthetic suitability, glass transition temperature (Tg) of polymer, solubility, and the like.

R ₃ represents C1 to C30 alkylene, C1 to C30 alkyleneoxy, or C1 to C30 ethyloxycarbonylaminoethyl. R _{3 is} preferably C1 to C25 alkylene, C1 to C25 alkyleneoxy or C1 to C25 ethyloxycarbonylaminoethyl, more preferably C1 to C20 alkylene, C1 to C20 alkyl Ethoxy or C1 ~ C20 ethyloxycarbonylaminoethyl, particularly preferably methylene, ethylene, propyl, butyl, ethyloxy, diethyloxy, triethyl Ethyloxy, ethyloxycarbonylaminoethyl. These groups may have a substituent. At this time, as the substituent of the above R ₃ , a C1-C20 alkyl group is preferred, of which a C1-C15 alkyl group is more preferred, a C1-C10 alkyl group is even more preferred, and a C1-C7 alkyl group is particularly preferred . As said substituent, the methyl group, ethyl group, a branched or linear propyl group, a butyl group, a pentyl group, and a hexyl group are the most preferable, considering a raw material, a synthetic suitability, etc. Among them, the alcoholic hydroxyl group may reduce the glass transition temperature (Tg), so it is excluded from the preferable examples.

R ₄ represents a group containing an unsaturated double bond. Specifically, vinyloxy, allyloxy, (meth) acrylfluorenyloxy, 4-vinylphenyloxy, 4-vinylphenylmethyloxy, and vinyl are preferred. Ester groups, etc. Among these, R _{4 is more} preferably a vinyloxy group, an allyloxy group, a (meth) acrylfluorenyloxy group, a 4-vinylphenylmethyloxy group, or a vinyl ester group, and particularly preferably Allyloxy, (meth) acrylfluorenyloxy, 4-vinylphenylmethyloxy.

The glass transition temperature (Tg) of the adhesive of the present invention containing the structural unit represented by Chemical Formula 1 can be adjusted by using the molecular weight, molecular structure, hydrogen bonding interaction, etc. of the adhesive itself, and the glass of the adhesive used in combination can be considered The transition temperature (Tg), the affinity with the adhesive and other ingredients used in combination, and the overall viscoelasticity of the system are determined. In the case where the glass transition temperature (Tg) of the adhesive is too low, the heat resistance of the formed pattern is reduced, causing problems such as heat flow. In addition, problems such as an increase in adhesion of the coating film and a decrease in workability also occur. Therefore, it is not preferable to include an alcoholic hydroxyl group in the adhesive. In addition, since the hydrogen bonding interaction of the alcoholic hydroxyl group is weak, from this viewpoint, a large effect cannot be exhibited in many cases.

The glass transition temperature (Tg) of the adhesive of the present invention is preferably in the range of -20 to 250 ° C, more preferably in the range of -15 to 250 ° C, and particularly preferably in the range of -10 to 250 ° C. The adhesive of the present invention may be used in combination with other adhesives. In addition, adhesives other than the above will be described later.

The molecular weight of the adhesive of the present invention is a weight average molecular weight, preferably 500 to 10,000,000 Da (dalton: unit of molecular weight), more preferably 1,000 to 5,000,000 Da, and particularly preferably 2,000 to 5,000,000 Da.

The component (that is, a copolymerization component) constituting the adhesive of the present invention together with the structural unit represented by Chemical Formula 1 is not particularly limited as long as it can be copolymerized (at least 2 yuan).

Examples of the copolymerization component include Japanese Patent Laid-Open No. 59-44615, Japanese Patent Laid-Open No. 54-34327, Japanese Patent Laid-Open No. 58-12577, Japanese Patent Laid-Open No. 54-25957, and Japanese Patent Laid-Open No. 59-53836. , Their methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid (anhydride) copolymers described in the specification of Japanese Patent Application Laid-Open No. 59-71048, Partially esterified maleic acid copolymers, partially fluorinated maleic acid copolymers, monomers used in (meth) acrylic acid esters, (meth) acrylic acid amines, vinyl-based aromatic compounds Hydrocarbon rings, heteroaromatic rings with vinyl, maleic anhydride, itaconic acid esters, crotonic acid esters, (meth) acrylonitrile, (meth) crotononitrile, various styrenes , Various vinyl benzoates, various vinyl acetates, vinyl carbazoles, vinyl pyrrolidone and the like.

Among them, the above-mentioned copolymerization components are preferably (meth) acrylic acid, C1 to C25 (cyclo) alkyl (meth) acrylate, C1 to C25 (meth) acrylate having a bicyclic ring, and C1 to C25 aralkyl (Meth) acrylate, C1 ~ C25 aryl (meth) acrylate, (meth) acrylamide, C1 ~ C25 second or third (cyclo) alkyl (meth) acrylamide, C1 ~ C25 (meth) acrylamide with second or third bicyclic ring, C1 ~ C25 second or third aralkyl (meth) acrylamide, C1 ~ C25 second or third aryl (methyl) Acrylamide, C1 ~ C25 (meth) acrylfluorenyl morpholine, substituted or unsubstituted C1 ~ C25 aromatic hydrocarbon ring having vinyl group, having C1 ~ C25 heteroaromatic ring of substituted or unsubstituted vinyl, maleic anhydride, substituted or unsubstituted C1 ~ C25 (α-methyl-) styrene, vinylimidazole, ethylene Triazole, maleic anhydride, substituted or unsubstituted C1 ~ C25 partially esterified maleic acid copolymer, substituted or unsubstituted C1 ~ C25 partially esterified maleic acid , Methyl Jasmonate, itaconic acid, C1 ~ C25 itaconic acid (cyclo) alkyl ester, C1 ~ C25 itaconic acid ester with bicyclic ring, C1 ~ C25 itaconic acid aralkyl ester, C1 ~ C25 itaconate aryl ester, crotonic acid, C1 ~ C25 crotonic acid (cyclo) alkyl ester, C1 ~ C25 crotonic acid ester having bicyclic ring, C1 ~ C25 crotonic acid aralkyl ester, C1 ~ C25 crotonic acid aromatic Base esters, C1-C25 vinyl benzoates, C1-C25 vinyl acetates, (meth) acrylonitrile, (meth) crotononitrile, C1-C25 vinyl carbazole, vinyl pyrrolidone.

Among them, (meth) acrylic acid, C1 to C20 (cyclo) alkyl (meth) acrylate, C1 to C20 (meth) acrylate having bicyclic ring, C1 to C20 aralkyl (meth) acrylic acid Ester, C1 ~ C20 aryl (meth) acrylate, (meth) acrylamide, C1 ~ C20 second or third (cyclo) alkyl (meth) acrylamide, C1 ~ C20 with second or The third bicyclic (meth) acrylamide, C1 ~ C20 second or third aralkyl (meth) acrylamide, C1 ~ C20 second or third aryl (meth) acrylamide; C1 ~ C20 (meth) acrylfluorenylmorpholine, substituted or unsubstituted C1 ~ C20 aromatic hydrocarbon ring with vinyl group, substituted or unsubstituted C1 ~ C20 heteroaromatic ring with vinyl group, Maleic anhydride, substituted or unsubstituted C1-C20 partially esterified maleic acid copolymers, substituted or unsubstituted C1-C20 partially aminated maleic acid, substituted or Unsubstituted C1 ~ C20 (α-methyl-) styrene, methyl jasmonate, itaconic acid, C1 ~ C20 itaconic acid (cyclo) alkyl ester, C1 ~ C20 itaconic acid ester with bicyclic ring , C1 ~ C20 aryl itaconate, C1 ~ C20 aryl itaconate, crotonic acid, C1 ~ C20 croton Acid (cyclo) alkyl esters, C1 to C20 crotonic acid esters with bicyclic ring, C1 to C20 crotonic acid aralkyl esters, C1 to C20 crotonic acid aryl esters, C1 to C20 vinyl benzoate, C1 to C20 acetic acid Vinyl esters, C1-C20 vinyl carbazole, vinyl pyrrolidone; (meth) acrylonitrile, (meth) crotononitrile.

Among these, (meth) acrylic acid, meth (meth) acrylate, ethyl (meth) acrylate, linear or branched propyl (meth) acrylate, linear or Branched butyl (meth) acrylate, linear or branched pentyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, n-heptyl (methyl Acrylate), 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, diamond Alkyl (meth) acrylate, isobornyl (meth) acrylate, isobornane methyl (meth) acrylate, norbornene methyl (meth) acrylate; benzyl (meth) acrylate Esters, naphthylmethyl (meth) acrylate, anthracenemethyl (meth) acrylate, phenylethyl (meth) acrylate; phenyl (meth) acrylate, naphthyl (meth) acrylate Esters, (meth) acrylamide, (di) methyl (meth) acrylamide, (di) ethyl (meth) acrylamide, linear or branched (di) propyl (methyl) Acrylamide, linear or branched (Di) butyl (meth) acrylamide, linear or branched (di) pentyl (meth) acrylamide, (di) n-hexyl (meth) acrylamide, (di) cyclo Hexyl (meth) acrylamide, (di-) 2-ethylhexyl (meth) acrylamide; adamantyl (meth) acrylamide, n-adamantyl (meth) acrylamide; benzyl (Meth) acrylamide, naphthylethyl (meth) acrylamide, phenylethyl (meth) acrylamide; (di) phenyl (meth) acrylamide, naphthyl (methyl) Propyl) acrylamide, (meth) acrylfluorenylmorpholine, piperidinylacrylamide, pyrrolidinylacrylamide, (α-methyl) styrene, vinylpyridine, vinylimidazole, vinyltriamine Azole, maleic anhydride, methyl jasmonate; itaconic acid; crotonic acid, methyl crotonic acid ester, ethyl crotonic acid ester, linear or branched propyl crotonic acid ester, linear or branched Butylcrotonate, linear or branched pentylcrotonate, n-hexylcrotonate, cyclohexylcrotonate, n-heptylcrotonate, 2-ethylhexylcrotonate, n-octylcroton Acid ester, n-decyl crotonate, n-dodecyl bar Crotonate; adamantyl crotonate, isobornyl crotonate, isobornyl methyl crotonate, norbornene methyl crotonate; benzyl crotonate, naphthyl methyl crotonate, Anthracene crotonate, phenylethyl crotonate; phenyl crotonate, naphthyl crotonate, Vinyl benzoate, vinyl acetate, vinyl carbazole, vinyl pyrrolidone and the like.

The carboxyl group may be derived from a metal salt.

As the above substituents, C1 to C20 alkyl, C1 to C20 alkoxy, C1 to C20 aralkyl, C1 to C20 aryl, C1 to C20 fluorenyloxy, C1 to C20 fluorenyl, and C1 to C20 C20 alkoxycarbonyl, C1 ~ C20 arylcarbonyl, C1 ~ C20 dialkylamino, C1 ~ C20 alkylamino, halogen atom, cyano, furanyl, furfuryl, tetrahydrofuranyl, tetrahydrofurfuryl, Alkylthio, trimethylsilyl, trifluoromethyl, carboxyl, thienyl, morpholino, morpholinocarbonyl, and the like.

Among them, the above-mentioned substituents are more preferably C1 to C15 alkyl, C1 to C15 alkoxy, C1 to C15 aralkyl, C1 to C15 aryl, C1 to C15 fluorenyloxy, C1 to C15 fluorenyl, C1 ~ C15 alkoxycarbonyl, C1 ~ C15 arylcarbonyl, C1 ~ C15 dialkylamino, C1 ~ C15 alkylamine, halogen atom, cyano, furanyl, furfuryl, tetrahydrofuranyl, tetrahydrofuran Group, alkylthio, trimethylsilyl, trifluoromethyl, carboxyl, thienyl, morpholino, morpholinocarbonyl, and the like.

In addition, as the substituent, a methyl group, an ethyl group, a straight or branched propyl group, a straight or branched butyl group, a straight or branched pentyl group, n-hexyl group, cyclohexyl group, N-heptyl, 2-ethylhexyl, n-octyl, n-decyl, n-dodecyl, methyloxy, ethyloxy, straight or branched propyloxy, straight or branched Butyloxy, straight or branched pentyloxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, 2-ethylhexyloxy, n-octyloxy, n-decyl Oxy, n-dodecyloxy, benzyl, phenethyl, naphthylmethyl, naphthylethyl, phenyl, naphthyl, methylcarbonyloxy, ethylcarbonyloxy, straight or branched Chain propylcarbonyloxy, straight or branched butylcarbonyloxy, straight or branched pentylcarbonyloxy, n-hexylcarbonyloxy, cyclohexylcarbonyloxy, n-heptylcarbonyloxy , 2-ethylhexylcarbonyloxy, n-octylcarbonyloxy, n-decylcarbonyloxy, n-dodecylcarbonyloxy, methylcarbonyl (ethenyl), ethylcarbonyl, linear or branched The cyclopropylcarbonyl, straight or branched chains butylcarbonyl group, a straight-chain Or branched chain pentylcarbonyl, n-hexylcarbonyl, cyclohexylcarbonyl, n-heptylcarbonyl, 2-ethylhexylcarbonyl, n-octylcarbonyl, n-decylcarbonyl, n-dodecylcarbonyl, methyloxycarbonyl , Ethyloxycarbonyl, straight or branched propyloxycarbonyl, straight or branched butyloxycarbonyl, straight or branched pentyloxycarbonyl, n-hexyloxycarbonyl, ring Hexyloxycarbonyl, n-heptyloxycarbonyl, 2-ethylhexyloxycarbonyl, n-octyloxycarbonyl, n-decyloxycarbonyl, n-dodecyloxycarbonyl, benzamyl, naphthalene Carbonyl groups; (di) methylamino, (di) ethylamino, straight or branched (di) propylamino, straight or branched (di) butylamino, straight or Branched (di) pentylamino, (di) n-hexylamino, (di) cyclohexylamino, (di) n-heptylamino, (di) 2-ethylhexylamino; fluorine atom, Chlorine atom, bromine atom; cyano, furanyl, furfuryl, tetrahydrofuranyl, tetrahydrofurfuryl, alkylthio, trimethylsilyl, trifluoromethyl, carboxyl, thienyl, morpholinyl, Phosphono Carbonyl group and the like.

In addition, these substituents may be further substituted with the above-mentioned substituents. Among them, the alcoholic hydroxyl group may reduce the glass transition temperature (Tg), and is therefore excluded from the examples of preferred substituents.

In addition, (meth) acrylonitrile and (meth) crotononitrile can be exemplified as examples of particularly preferred copolymerization components (comonomers).

As the copolymerization component, as other hydrophilic monomers, phosphoric acid, phosphate esters, quaternary ammonium salts, ethoxyl chains, propyloxyl chains, sulfonic acids and their salts, and morpholinoethyl Monomers and the like are useful.

The sulfonic acid group and carboxylic acid group may be derived from a metal salt.

In the adhesive of the present invention, the type and number of the copolymerized monomers are not particularly limited, but preferably 1 to 12 species, more preferably 1 to 8 species, and particularly preferably 1 to 5 species.

Hereinafter, specific examples of the adhesive in the form of Chemical Formula 1 of the present invention are shown by Chemical Formulas 1-1 to 1-24, but the present invention is not limited thereto.

[Chemical Formula 1-1]

[Chemical Formula 1-6] Glass transition temperature (Tg) = 150 ° C

[Chemical Formula 1-11] Glass transition temperature (Tg) = 140 ° C

[Chemical Formula 1-16] Glass transition temperature (Tg) = 140 ° C

Next, the curable composition containing quantum dots of the present invention can include a binder of Chemical Formula 2, and the glass transition temperature can be -20 to 250 ° C.

By containing the compound represented by Chemical Formula 2, the curability at the time of light (ray) irradiation can be improved, and a pattern with a high degree of curing can be formed. Therefore, it is high-resolution, and it can exhibit excellent brightness characteristics by acting as a protective group on the surface of the quantum dots from the influence of free radicals generated in the POB process.

In Chemical Formula 2, R ₅ and R ₆ are each independently the same as or different from each other, and represent hydrogen or a C1-C6 alkyl group.

基。 R ₇ represents oxygen, -NH- or

base.

R ₈ represents C1-C30 alkylene, C1-C30 alkyleneoxy or C1-C30 ethyloxycarbonylaminoethyl.

Among the alkylene, alkyleneoxy, and ethyloxycarbonylaminoethyl groups represented by R ₈ described above, the groups C1 to C25 are preferred, and the groups C1 to C20 are more preferred. Methylene, ethylidene, propylidene, butylidene, ethylideneoxy, diethylideneoxy, triethylidyloxy, ethyloxycarbonylaminoethyl are preferred. These groups may have a substituent. As the substituent of the aforementioned R ₈ , a C1 to C20 alkyl group or an OH group is preferred. Among them, a C1 to C15 alkyl group or an OH group is more preferred, and a C1 to C10 alkyl group or an OH group is even more preferred. It is a C1-C7 alkyl group or an OH group. Among these, in consideration of raw materials, synthetic suitability, and the like, methyl, ethyl, branched or linear propyl, butyl, pentyl, hexyl, and OH groups are most preferable.

R ₉ represents a group containing an unsaturated double bond.

The above R ₉ represents a group containing an unsaturated double bond, and is preferably selected from the group consisting of vinyloxy, allyloxy, (meth) acrylfluorenyloxy, 4-vinylphenyloxy, 4- A group consisting of vinylphenylmethyloxy, styryl, vinylester, and vinylether. Of these, vinyloxy, allyloxy, (meth) acrylfluorenyloxy, 4-vinylphenylmethyloxy, and vinyl ester are more preferred, and allyloxy is particularly preferred Group, (meth) acrylfluorenyloxy, 4-vinylphenylmethyloxy.

The above-mentioned X represents a value of 0 <X <100. More preferably, X can consider the strength of the film, elastic modulus, viscoelasticity, heat resistance, suitability for synthesis, glass transition temperature (Tg) of the polymer, solubility, developability, suitability for synthesis, and developability of the film , The concentration of the developing solution, the strength of the interaction with the quantum dots and other components, and so on. Among them, X is preferably a value of 5 to 95, more preferably a value of 10 to 90, and particularly preferably a value of 15 to 85.

As the molecular weight of the compound represented by the above Chemical Formula 2, the weight average molecular weight is preferably 500 to 10,000,000 Da (Dalton: molecular weight unit), more preferably 100 to 5,000,000 Da, and particularly preferably 2,000 to 5,000,000 Da.

The above-mentioned adhesive is particularly preferably water-soluble or alkali-soluble. Here, alkali-soluble means It is soluble in an aqueous solution of the basic compound described below, or a mixture of any organic solvent that is miscible with water and an aqueous solution of the basic compound.

Hereinafter, specific examples of the compound represented by the aforementioned Chemical Formula 2 are given, but the present invention is not limited thereto.

The adhesive containing the compound represented by the above Chemical Formula 1 or Chemical Formula 2 is preferably 10 to 90% by mass, and more preferably 15 to 80% by mass, with respect to the total solid content (mass) of the curable composition containing the quantum dots.

If the content of the adhesive is lower than the above range, the effect of improving the degree of curing due to light (radiation) irradiation is insufficient, and heat resistance, resolution, residual film rate in the cured portion, and Effects such as developability are reduced. Moreover, if it exceeds the said range, content of other components will fall too much, and developability, colorability, etc. may be impaired.

The curable resin composition of the present invention contains photoluminescent quantum dot particles.

The so-called quantum dots are nanometer-sized semiconductor materials. Atoms forming molecules Nanoparticles are formed by the aggregation of small molecules such as clusters. When such nano-particles are particularly semiconductor-like, they are called quantum dots. When a quantum dot obtains energy from the outside and becomes an excited state, it will automatically release energy that matches the corresponding energy band gap.

The curable composition of the present invention contains such photoluminescent quantum dot particles, and a color filter manufactured therefrom can emit light (photoluminescence) by irradiation of light. In a conventional image display device including a color filter, white light passes through the color filter to express color. In the process, a part of the light is absorbed by the color filter, and thus the light efficiency is reduced. However, in the case where the color filter manufactured from the curable composition of the present invention is included, the color filter emits light by itself with the light of a light source, and thus can exhibit excellent light efficiency. In addition, since light having color is emitted, color reproducibility is excellent, and since light is emitted in all directions by photoluminescence, a viewing angle can also be improved.

The quantum dot particle of the present invention is not particularly limited as long as it is a quantum dot particle capable of emitting light by the stimulation of light, and can be selected from, for example, a group II-VI semiconductor compound; a group III-V semiconductor compound; and a group IV-VI semiconductor compound. ; Group IV elements or compounds containing them; and groups consisting of combinations thereof. It can be used individually or in mixture of 2 or more types. The group II-VI semiconductor compound can be selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, and mixtures thereof, and selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, and mixtures thereof, and the group consisting of three elements of C. , CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof; the above-mentioned group III-V semiconductor compounds can be selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures of two-element compounds selected from the group consisting of GaNP, GaAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and mixtures of three-element compounds selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP Four-element compounds of the group consisting of, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof; the above-mentioned group IV-VI semiconductor compounds can be selected from the group consisting of: selected from the group consisting of SnS, SnSe , SnTe, PbS, PbSe, PbTe, and mixtures of two-element compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof, and Four-element compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof; the above-mentioned Group IV elements or compounds containing them can be selected from the group consisting of: elemental compounds selected from the group consisting of Si, Ge, and mixtures thereof And a two-element compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

The quantum dot particles may have a homogeneous single structure, a dual structure such as a core-shell, a gradient structure, or a mixed structure thereof. In the core-shell dual structure, the substance forming each core and shell can be formed of the semiconductor compounds different from each other mentioned above. For example, the core can include one or more substances selected from the group consisting of CdSe, CdS, ZnS, ZnSe, CdTe, CdSeTe, CdZnS, PbSe, AgInZnS, and ZnO, but is not limited thereto. The shell can include one or more substances selected from the group consisting of CdSe, ZnSe, ZnS, ZnTe, CdTe, PbS, TiO, SrSe, and HgSe, but is not limited thereto. The coloring photosensitive resin composition generally used in the manufacture of color filters includes red, green, and blue colorants in order to express color. Similarly, photoluminescent quantum dot particles can also be divided into red quantum dot particles and green. Quantum dot particles and blue quantum dot particles. The quantum dot particles of the present invention may be red quantum dot particles, green quantum dot particles, or blue quantum dot particles.

Quantum dot particles can be processed by wet chemical process, organic Synthesis of metal chemical deposition process or molecular beam epitaxy process. The wet chemical process is a method of adding a precursor substance to an organic solvent to grow particles. When crystals grow, organic solvents are naturally located on the surface of the quantum dot crystals to act as dispersants, thereby regulating the growth of the crystals. Therefore, they are used in combination with metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MOCVD). Compared with vapor deposition methods such as MBE, molecular beam epitaxy), the growth of nano particles can be controlled by an easier and cheaper process.

The content of the quantum dot particles of the present invention is not particularly limited. For example, the total weight of the solid content of the photosensitive resin composition is preferably contained in an amount of 3 to 80% by weight, and more preferably 5 to 70% by weight. If the content of the quantum dot particles is lower than the above range, the luminous efficiency is very weak, and if it exceeds the above range, there is a problem that the content of other compositions is relatively insufficient and it is difficult to form a pixel pattern.

The curable composition containing a quantum dot of the present invention may further include another binder that can be used in combination with the compound represented by the above Chemical Formula 1 or Chemical Formula 2.

Other adhesives are not particularly limited as long as they are alkali-soluble, and they are preferably selected from the aspects of heat resistance, developability, and availability.

As the alkali-soluble binder, a linear organic polymer is preferable, that is, a substance that is soluble in an organic solvent and can be developed in a weak alkaline aqueous solution. As such a linear organic polymer, a polymer having a carboxylic acid in a side chain can be used, for example, Japanese Patent Laid-Open No. 59-44615, Japanese Patent No. 54-34327, Japanese Patent No. 58-12577, and Japanese Patent No. 59-44615. Methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, and butylenes described in Japanese Patent Application Publication No. 54-25957, Japanese Patent Application Publication No. 59-53836, and Japanese Patent Application Publication No. 59-71048. Diacid copolymers, partially esterified maleic acid copolymers, etc .; acidic cellulose derivatives with carboxylic acids in the side chains.

In addition, substances obtained by adding an anhydride to a polymer having a hydroxyl group, etc., polyhydroxystyrene resin, polysiloxane resin, poly (2-hydroxyethyl (meth) acrylate), Polyvinylpyrrolidone, polyethylene oxide, polyvinyl alcohol and the like are also useful.

Moreover, in the 1st aspect, the adhesive agent which consists of the structural unit represented by the said Chemical Formula 1 and the component (namely, a copolymerization component) which comprises the adhesive agent of this invention can be used effectively.

It is also possible to copolymerize a monomer having a hydrophilic property, and examples thereof include alkoxyalkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, and glycerol (meth) acrylate Esters, (meth) acrylamide, N-hydroxymethacrylamide, second or third alkylacrylamide, dialkylaminoalkyl (meth) acrylates, morpholine (meth) Acrylate, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, vinyltriazole, methyl (meth) acrylate, ethyl (meth) acrylate, branched chain or Linear propyl (meth) acrylate, branched or linear butyl (meth) acrylate, phenoxyhydroxypropyl (meth) acrylate, etc. Others contain tetrahydrofurfuryl, phosphoric acid, Phosphate esters, quaternary ammonium salts, ethyloxy chains, propyleneoxy chains, sulfonic acids and their salts, monomers such as morpholinoethyl, and the like.

In the first aspect, the glass transition temperature (Tg) of the substance containing the structural unit represented by Chemical Formula 1 is in a range of -20 to 250 ° C, and other adhesives used in combination with the adhesive of the present invention are within a desired range. When maintaining the system's viscoelasticity and glass transition temperature (Tg), it may contain alcoholic hydroxyl groups.

In addition, in the present invention, from the viewpoint of improving the crosslinking efficiency, it is possible to have a polymerizable group in the side chain and an allyl group, a (meth) acrylic group, an allyloxyalkyl group, or the like in the side chain. Polymers and the like are also useful. Examples of the polymer having a polymerizable group in a side chain include KS RESIST-106 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), CYCLOMER P series (manufactured by DAICEL Chemical Industry Co., Ltd.), and the like.

In addition, from the viewpoint of further improving the strength of the cured film, alcohol-soluble nylon, polyethers of 2,2-bis- (4-hydroxyphenyl) -propane, and epichlorohydrin are also useful.

Among these various kinds of adhesives, from the viewpoint of heat resistance, a polymer is preferable. Hydroxystyrene resin, polysiloxane resin, acrylic resin, acrylamide resin, acrylic / acrylamide copolymer resin, from the viewpoint of controlling the developability, acrylic resin and acrylamide are preferred Series resin, acrylic / acrylamide copolymer resin. Moreover, when using together with the adhesive agent of a 1st viewpoint, it is preferable to form an adhesive agent from the structural unit represented by Chemical formula 1, and the component (namely, a copolymerization component) which comprises a polymer compound.

The acrylic resin is preferably formed of a monomer selected from the group consisting of benzyl (meth) acrylate, (meth) acrylic acid, hydroxyethyl (meth) acrylate, (meth) acrylamide, and the like Copolymer, KS RESIST-106 (product of Osaka Organic Chemical Industry Co., Ltd.), CYCLOMER P series, etc.

In addition, alkali-soluble phenol resins are also useful. Examples of the alkali-soluble phenol resin include a novolac resin and a vinyl polymer.

Examples of the novolak resin include those obtained by condensing phenols and aldehydes in the presence of an acid catalyst. Examples of the phenols include phenol, cresol, ethylphenol, butylphenol, xylenol, phenylphenol, catechol, resorcinol, catechol, naphthol, and bisphenol A Wait. These phenols can be used alone or in combination of two or more. Examples of the aldehydes include formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, and benzaldehyde.

Specific examples of the novolac resin include a condensation product of m-cresol, p-cresol, or a mixture thereof with formalin. These novolak resins can be adjusted by a method such as separation to adjust the molecular weight distribution. In addition, a low molecular weight component having a phenolic hydroxyl group, such as bisphenol C or bisphenol A, may be mixed with the novolac resin.

As the weight average molecular weight (polystyrene equivalent value measured by GPC method) of the above-mentioned other adhesives, 500 to 10,000,000 Da (Dalton: molecular weight unit) is preferable, and 1,000 to 5,000,000 Da is more preferable, and particularly preferably 2,000 ~ 5,000,000Da.

In addition, the above-mentioned other adhesives are substances which can be used in combination with the adhesive of the present invention. When the adhesive of the present invention can fully exert its performance, it may be used. Do not use.

When the adhesive represented by Chemical Formula 1 or Chemical Formula 2 of the present invention is used in combination with other adhesives, the amount of the other adhesives used in the curable composition containing quantum dots of the present invention is relative to the composition. The total solid content is preferably 0 to 90% by mass, more preferably 0 to 80% by mass, and particularly preferably 0 to 70% by mass.

The curable composition containing a quantum dot of the present invention can further include a crosslinking agent so that a cured film can be obtained with higher sensitivity.

The crosslinking agent that can be used in the present invention is not particularly limited as long as it is a material that cures a film by a crosslinking reaction, and examples thereof include those selected from epoxy resins (a), methylol (b), and alkane. A melamine compound, a guanamine compound, a glycoluril compound, or a urea compound substituted with one or more substituents of oxymethyl and fluorenyloxymethyl, selected from methylol (c), alkoxymethyl, and fluorenyl A phenol compound, a naphthol compound, or a hydroxyanthracene compound substituted with one or more substituents of an oxymethyl group. Among these, a polyfunctional epoxy resin is preferable.

The cross-linking agent (a) may be any one having an epoxy group and having cross-linking properties. For example, it may be bisphenol A diglycidyl ether, ethylene glycol diglycidyl ether, butanediol diglycidyl ether , Hexylene glycol diglycidyl ether, dihydroxy biphenyl diglycidyl ether, diglycidyl phthalate, N, N-diglycidyl aniline and other low molecular compounds containing two members of glycidyl, the same In the method, three-membered glycidyl-containing low-molecular compounds represented by trimethylolpropane triglycidyl ether, trimethylol phenol triglycidyl ether, TrisP-PA triglycidyl ether, etc. Pentaerythritol tetraglycidyl ether, tetramethylol bisphenol A tetraglycidyl ether, and other low molecular compounds containing 4-membered glycidyl groups, such as diisopentaerythritol pentaglycidyl ether and diisopropyl Low-molecular-weight compounds containing multi-membered glycidyl groups, such as pentaerythritol hexaglycidyl ether, and polyglycidyl (meth) acrylate, 2,2-bis (hydroxymethyl) -1-butanol, 1,2 -Epoxy-4- (2-oxiranyl) cyclohexane adducts, etc. Oil-based polymer compound.

Methylol, alkoxymethyl, and fluorenyloxymethyl as the crosslinking agent (b) The number of substituents is 2 to 6 in the case of melamine compounds, 2 to 4 in the case of glycoluril compounds, guanamine compounds, and urea compounds, and 5 to 6 in the case of melamine compounds. In the case of a glycoluril compound, a guanamine compound, and a urea compound, 3 to 4 are preferred.

Hereinafter, the melamine compound, guanamine compound, glycoluril compound, and urea compound of the above-mentioned crosslinking agent (b) are generally referred to as (containing methylol, alkoxymethyl, or fluorenyloxy) the crosslinking agent (b). Methyl) compounds.

The above-mentioned methylol group-containing compound concerning the cross-linking agent (b) can be obtained by dissolving the alkoxymethyl-group-containing compound regarding the cross-linking agent (b) in an alcohol, hydrochloric acid, sulfuric acid, nitric acid, methanesulfonic acid, etc. It is obtained by heating in the presence of an acid catalyst. The above-mentioned fluorenyloxymethyl-containing compound for the crosslinking agent (b) can be obtained by mixing the hydroxymethyl-containing compound for the crosslinking agent (b) with fluorenyl chloride in the presence of a basic catalyst and stirring. get.

Hereinafter, specific examples of the compound having the above-mentioned substituents on the cross-linking agent (b) are exemplified.

Examples of the melamine compound include 1 to 5 methoxymethylated compounds of hexamethylolmelamine, hexamethoxymethylmelamine, and hydroxymethyl of hexamethylolmelamine or a mixture thereof, One to five of the hexamethyloxymelamine, hexamethyloxymethylmelamine, and hydroxymethyl of hexamethylolmelamine are methylated with a methyloxy group or a mixture thereof.

Examples of the guanamine compounds include methoxymethylated compounds in which one to three methylol groups of tetramethylolguanamine, tetramethoxymethylguanamine, and tetramethylolguanidine are methoxymethylated, or Mixtures thereof, tetramethoxyethylguanamine, tetramethyloxymethylguanamine, compounds in which 1 to 3 methylol groups of tetramethylolguanamine are methylated with methyloxy, or mixtures thereof, etc. .

Examples of the glycoluril compounds include methoxymethylated one to three of the methylol groups of tetramethylol glycoluril, tetramethoxymethyl glycoluril, and tetramethylol glycoluril. Compounds or mixtures thereof, one to three of the methylol groups of tetramethylol glycoluril are methylated with fluorenyloxy Compounds or mixtures thereof.

Examples of the urea compound include a tetramethylol urea, a tetramethoxymethyl urea, a methoxymethylated compound of one to three methylol groups of tetramethylol urea, or a mixture thereof, and Methoxyethylurea and the like.

These compounds concerning the crosslinking agent (b) may be used alone or in combination. The above-mentioned crosslinking agent (c) is a phenol compound, a naphthol compound or a hydroxyanthracene compound substituted with one or more groups selected from the group consisting of methylol, alkoxymethyl and fluorenyloxymethyl, and the above-mentioned crosslinking agent ( The case of b) is the same as a substance that suppresses intermixing with a photoresist that is overcoated by thermal crosslinking, and further enhances the film strength. Hereinafter, these compounds are generally referred to as a compound containing a methylol group, an alkoxymethyl group, or a fluorenyloxymethyl group with respect to the crosslinking agent (c).

As the number of hydroxymethyl, fluorenyloxymethyl, or alkoxymethyl groups contained in the above-mentioned crosslinking agent (c), at least two per molecule are required, from the viewpoint of thermal crosslinkability and storage stability It is preferably a compound in which all the 2 and 4 positions of the phenol compound as a skeleton are substituted. In addition, the naphthol compound and the hydroxyanthracene compound as the skeleton are also preferably compounds in which all ortho and para positions of the OH group are substituted. The 3- or 5-position of the phenol compound may be unsubstituted or may have a substituent. The naphthol compound may be unsubstituted or may have a substituent other than the ortho position of the OH group.

The above-mentioned methylol group-containing compound concerning the crosslinking agent (c) can be prepared by using a compound having a hydrogen atom at the 2- or 4-position of a phenolic OH group as a raw material, and It is obtained by reacting with formalin in the presence of basic catalysts such as ammonia and tetraalkylammonium hydroxide.

The alkoxymethyl-containing compound of the cross-linking agent (c) can be obtained by mixing the methylol-containing compound of the cross-linking agent (c) in an alcohol, hydrochloric acid, sulfuric acid, nitric acid, methanesulfonic acid, and the like. It is obtained by heating in the presence of an acid catalyst.

The above-mentioned fluorenyloxymethyl-containing compound regarding the cross-linking agent (c) can be obtained by The methylol group-containing compound of the crosslinking agent (c) is obtained by reacting with a fluorenyl chloride in the presence of a basic catalyst.

Examples of the skeleton compound in the cross-linking agent (c) include an unsubstituted phenol compound, a naphthol, and a hydroxyanthracene compound in ortho or para positions of the phenolic OH group. For example, phenol, cresol, Each isomer, bisphenols such as 2,3-xylenol, 2,5-xylenol, 3,4-xylenol, 3,5-xylenol, bisphenol A, 4,4'- Dihydroxybiphenyl, TrisPPA (manufactured by Honshu Chemical Industry Co., Ltd.), naphthol, dihydroxynaphthalene, 2,7-dihydroxyanthracene, and the like.

As specific examples of the cross-linking agent (c), as the phenol compound, for example, trimethylolphenol, tris (methoxymethyl) phenol, and trimethylolphenol may be used. 1 to 2 methylol groups of methoxymethylated compounds, trimethylol-3-cresol, tris (methoxymethyl) -3-cresol, and trimethylol-3-cresol Methoxymethylated compounds, dimethylol cresols such as 2,6-dimethylol-4-cresol, tetramethylolbisphenol A, tetramethoxymethylbisphenol A, tetramethylol 1 to 3 hydroxymethyl bismethylated compounds of hydroxymethyl bisphenol A, tetramethylol-4,4'-bishydroxybiphenyl, tetramethoxymethyl-4,4 ' -Dihydroxy biphenyl, TrisP-PA hexamethylol body, TrisP-PA hexamethoxymethyl body, TrisP-PA hexamethylol body 1-5 methylol groups via methoxymethyl Compounds, bishydroxymethylnaphthalene glycol, and the like.

Examples of the hydroxyanthracene compound include 1,6-dihydroxymethyl-2,7-dihydroxyanthracene, and examples of the fluorenyloxymethyl-containing compound include the above-mentioned hydroxymethyl-containing compound. Compounds in which one or all of the hydroxymethyl groups of the compound are methylated with fluorenyloxy, and the like.

As a preferable compound among these compounds, trimethylolphenol, bishydroxymethyl p-cresol, tetramethylol bisphenol A, TrisP-PA (manufactured by Honshu Chemical Industry Co., Ltd.) A phenol compound in which a compound or a methylol group thereof is substituted with an alkoxymethyl group and both a methylol group and an alkoxymethyl group.

These compounds concerning the crosslinking agent (c) may be used alone or in combination.

In the present invention, it is not necessary to necessarily contain the above-mentioned crosslinking agent. When contained, the total content of the crosslinking agents (a) to (c) in the curable composition containing quantum dots varies depending on the material. Similarly, the solid content (mass) of the curable composition is preferably 0 to 70% by weight, more preferably 0 to 50% by weight, and most preferably 0 to 30% by weight.

The curable composition containing a quantum dot of the present invention may further include a monomer or oligomer having one or more ethylenically unsaturated groups.

The monomer or oligomer having one or more ethylenically unsaturated groups is preferably a compound having one or more ethylenic double bonds capable of addition polymerization and having a boiling point of 100 ° C. or more under normal pressure. By containing the photopolymerization initiator and the like described later, the curable composition containing the quantum dots of the present invention can be constituted in a negative type, and from the viewpoint of further improving the curability, curing with positive quantum dots can be included. Contained in sexual composition.

Examples thereof include monofunctional acrylates such as polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and phenoxyethyl (meth) acrylate, and methacrylic acid. Esters; polyethylene glycol di (meth) acrylate, trimethylolethane tri (meth) acrylate, neopentyl glycol di (meth) acrylate, isopentaerythritol tri (meth) acrylic acid Ester, isopentaerythritol tetra (meth) acrylate, diisopentaerythritol penta (meth) acrylate, diisopentaerythritol hexa (meth) acrylate, hexanediol (meth) acrylate, Trimethylolpropane tris (propenyloxypropyl) ether, tris (propenyloxyethyl) isocyanurate, glycerol, trimethylolethane, etc. (Meth) acrylic acid esters after the addition of propane and polyfunctional alcohols, the aminomethyl esters described in Japanese Patent Publication No. 48-41708, Japanese Patent Publication No. 50-6034, and Japanese Patent Publication No. 51-37193 Ester acrylates, polyester acrylates described in JP 48-64183, JP 49-43191, and JP 52-30490, as epoxy resins Epoxy acrylates with (meth) acrylic acid and the product of polyfunctional acrylates, methacrylates and mixtures thereof. In addition, the materials introduced as photocurable monomers and oligomers in pages 300 to 308 of Japan Adv. Association Vol.20 and No.7 can be cited.

The curable composition containing a quantum dot of the present invention can further include a photopolymerization initiator.

The photopolymerization initiator may be contained together with the above monomers and the like when the dye-containing curable composition of the present invention is constituted in a negative form, and may be contained if necessary in the case of a positive form. The photopolymerization initiator is not particularly limited as long as it is a substance capable of polymerizing the monomer or oligomer, and it is preferably selected from the viewpoints of characteristics, initiation efficiency, absorption wavelength, availability, and cost.

As the photopolymerization initiator, for example, one or more active halogen compounds selected from the group consisting of a halogenated methyloxadiazole compound and a halogenated methyl sinetriazine compound, a 3-aryl-substituted coumarin compound, and a ketodimer , Benzophenone compounds, acetophenone compounds and their derivatives, cyclopentadiene-benzene-iron complexes and their salts, and oxime-based compounds.

As the active halogen compound of the halogenated methyloxadiazole compound, 2-halomethyl-5-vinyl-1,3,4-oxadiazole compounds described in Japanese Patent Publication No. 57-6096, 2 -Trichloromethyl-5-styryl-1,3,4-oxadiazole, 2-trichloromethyl-5- (p-cyanostyrene) -1,3,4-oxadiazole, 2-trichloromethyl-5- (p-methoxystyryl) -1,3,4-oxadiazole and the like.

As the active halogen compound of the halogenated methyl s-triazine-based compound, there are vinyl halogenated methyl s-triazine compounds described in Japanese Patent Publication No. 59-1281, and Japanese Unexamined Patent Publication No. 53-133428. 2- (naphthalene-1-yl) -4,6-dihalomethylmethanetriazine compounds and 4- (p-aminophenyl) -2,6-dihalomethylmethanetriazine compounds.

Specifically, there are 2,4-bis (trichloromethyl) -6-p-methoxystyryl mesazine, 2,6-bis (trichloromethyl) -4- (3,4- (Methyldioxyphenyl) -1,3,5-triazine, 2,6-bis (trichloromethyl) -4- (4-methoxyphenyl) -1,3,5-triazine , 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl-1,3-butadienyl) triazine, 2-trichloromethyl-4-amine 6-p-methoxystyryl mesazine, 2- (naphthalen-1-yl) -4,6-bis-trichloromethyl mesazine, 2- (4-methoxy-naphthalene-1 -Yl) -4,6-bis-trichloromethyl trimesazine, 2- (4-ethoxy-naphthalen-1-yl) -4,6-bis-trichloromethyl trimesazine, 2- (4-butoxy-naphthalen-1-yl) -4,6-bis-trichloromethylmethanetriazine, 2- [4- (2-methoxyethyl) -naphthalene-1-yl]- 4,6-bis-trichloromethyl trimesazine, 2- [4- (2-ethoxyethyl) -naphthalen-1-yl] -4,6-bis-trichloromethyl trimesazine, 2- [4- (2-butoxyethyl) -naphthalene-1-yl] -4,6-bis-tri Chloromethyl mesazine, 2- (2-methoxy-naphthalen-1-yl) -4,6-bis-trichloromethyl mesazine, 2- (6-methoxy-5-methyl -Naphthyl-2-yl) -4,6-bis-trichloromethyl mesazine, 2- (6-methoxynaphthalene-2-yl) -4,6-bis-trichloromethyl mesazine 2-, 5- (5-methoxy-naphthalen-1-yl) -4,6-bis-trichloromethyl-mizine, 2- (4,7-dimethoxy-naphthalen-1-yl)- 4,6-bis-trichloromethyl trimesazine, 2- (6-ethoxy-naphthalene-2-yl) -4,6-bis-trichloromethyl trimesazine, 2- (4,5 -Dimethoxy-naphthalen-1-yl) -4,6-bis-trichloromethyl-methanetriazine, 4- [p-N, N-bis (ethoxycarbonylmethyl) aminophenyl]- 2,6-bis (trichloromethyl) mesatriazine, 4- [o-methyl-p-N, N-bis (ethoxycarbonylmethyl) aminophenyl] -2,6-bis (trichloro (Methyl) trimesazine, 4- [p-N, N-bis (chloroethyl) aminophenyl] -2,6-bis (trichloromethyl) trimesazine, 4- [o-methyl-p- N, N-bis (chloroethyl) aminophenyl] -2,6-bis (trichloromethyl) mesatriazine, 4- (p-N-chloroethylaminophenyl) -2,6- Bis (trichloromethyl) mesatriazine, 4- (p-N-ethoxycarbonylmethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- [p.N, N-bis (phenyl) aminophenyl] -2,6-bis (trichloromethyl) triazine, 4- (p-N-chloroethyl Aminoaminophenyl) -2,6-bis (trichloromethyl) himetriazine, 4- [p-N- (p-methoxyphenyl) carbonylaminophenyl] -2,6-bis (tri Chloromethyl) mesatriazine, 4- [m-N, N-bis (ethoxycarbonylmethyl) aminophenyl] -2,6-bis (trichloromethyl) mesatriazine, 4- [m Bromo-p-N, N-bis (ethoxycarbonylmethyl) aminophenyl] -2,6-bis (trichloromethyl) mesatriazine, 4- [m-chloro-p-N, N-bis ( Ethoxycarbonylmethyl) aminophenyl] -2,6-bis (trichloromethyl) himetriazine, 4- [m-fluoro-p-N, N-bis (ethoxycarbonylmethyl) amino Phenyl] -2,6-bis (trichloromethyl) mesatriazine, 4- [o-bromo-p-N, N-bis (ethoxycarbonylmethyl) aminophenyl] -2,6-di (Trichloromethyl) mesatriazine, 4- [o-chloro-p-N, N-bis (ethoxycarbonylmethyl) aminophenyl] -2,6-bis (trichloromethyl) mesatriazine , 4- [o-Fluoro-p-N, N-bis (ethoxycarbonylmethyl) aminophenyl] -2,6-bis (trichloromethyl) himetriazine, 4- [o-bromo-p-N , N-bis (chloroethyl) aminophenyl] -2,6-bis (trichloromethyl) himetriazine, 4- [o-chloro-p-N, N-bis (chloroethyl) aminobenzene Yl] -2,6-bis (trichloromethyl) mesatriazine, 4- [o-fluoro-p-N, N-bis (chloroethyl) aminophenyl] -2,6-bis (trichloromethyl) Phenyl) himetriazine, 4- [m-bromo- N, N-bis (chloroethyl) aminophenyl] -2,6-bis (trichloromethyl) mesatriazine, 4- [m-chloro-p-N, N-bis (chloroethyl) amino Phenyl] -2,6-bis (trichloromethyl) mesatriazine, 4- [m-Fluoro-p-N-bis (chloroethyl) aminophenyl]- 2,6-bis (trichloromethyl) mesatriazine, 4- (m-bromo-p-N-ethoxycarbonylmethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine , 4- (m-Chloro-p-N-ethoxycarbonylmethylaminophenyl) -2,6-bis (trichloromethyl) s-triazine, 4- (m-fluoro-p-N-ethoxycarbonyl) (Methylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- (o-bromo-p-N-ethoxycarbonylmethylaminophenyl) -2,6-bis ( Trichloromethyl) mestriazine, 4- (o-chloro-p-N-ethoxycarbonylmethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- (o-fluoro -P-N-ethoxycarbonylmethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- (m-bromo-p-N-chloroethylaminophenyl) -2 , 6-bis (trichloromethyl) mesatriazine, 4- (m-chloro-p-N-chloroethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- ( M-fluoro-p-N-chloroethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- (o-bromo-p-N-chloroethylaminophenyl) -2, 6-bis (trichloromethyl) mesatriazine, 4- (o-chloro-p-N-chloroethylaminophenyl) -2,6-bis (trichloromethyl) mesatriazine, 4- (ortho Fluoro-p-N-chloroethylaminophenyl) -2,6-bis (trichloromethyl) himetriazine and the like.

In addition, TAZ series (for example, TAZ-107, TAZ-110, TAZ-104, TAZ-109, TAZ-140, TAZ-204, TAZ-113, TAZ) manufactured by Midori Chemical Co., Ltd. -123), T series made by PANCIM (for example, T-OMS, T-BMP, TR, TB), IRGACURE series made by Ciba Gage (for example, IRGACURE651, IRGACURE184, IRGACURE500, IRGACURE1000, IRGACURE149, IRGACURE819, IRGACURE261), Darocur series (e.g., Darocur1173), 4,4'-bis (diethylamino) -benzophenone, 2- (o-benzoylhydrazine) -1- [4- (phenylthio (Phenyl) phenyl] -1,2-octanedione, 2-benzyl-2-dimethylamino-4-morpholinobutyrylene, 2,2-dimethoxy-2-phenyl Acetophenone, 2- (o-chlorophenyl) -4,5-diphenylimidazolyl dimer, 2- (o-fluorophenyl) -4,5-diphenylimidazolyl dimer, 2- (O-methoxyphenyl) -4,5-diphenylimidazolyl dimer, 2- (p-methoxyphenyl) -4,5-diphenylimidazolyl dimer, 2- (p-methoxyphenyl) Dimethoxyphenyl) -4,5-diphenylimidazolyl dimer, 2- (2,4-dimethoxyphenyl) -4,5-diphenylimidazolyl dimer, 2 -(P-methylmercaptophenyl) -4,5-diphenylimidazolyl Dimer, benzoin isopropyl ether and the like.

Among these photopolymerization initiators, a sensitizer and a light stabilizer can be used in combination.

Specific examples thereof include benzoin, benzoin methyl ether, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, 9-anthone, 2-bromo -9-anthrone, 2-ethyl-9-anthrone, 9,10-anthraquinone, 2-ethyl-9,10-anthraquinone, 2-tert-butyl-9,10-anthraquinone, 2 , 6-dichloro-9,10-anthraquinone, xanthone, 2-methylxanthone, 2-methoxyxanthone, 2-ethoxyxanthone, Thioxanthone, 2,4-diethylthioxanthone, acridone, 10-butyl-2-chloroacridone, diphenylethylenedione, dibenzylideneacetone, (Dimethylamino) phenylstyryl ketone, p- (dimethylamino) phenyl-p-methylstyryl ketone, benzophenone, p- (dimethylamino) benzophenone (Or mignonone), p- (diethylamino) benzophenone, benzoxanthone, etc., benzothiazole-based compounds described in Japanese Patent Publication No. 51-48516, etc., TINUVIN1130, TINUVIN400, and the like.

In the curable composition containing a quantum dot of the present invention, other known initiators can be used in addition to the photopolymerization initiator.

Specifically, vicinal polyketaldonyl compounds disclosed in the specification of U.S. Patent No. 2,367,660, α-carbonyl compounds disclosed in the specification of U.S. Patent No. 2,367,661 and U.S. Patent No. 2,367,670, and U.S. Patent Acetoethers disclosed in Specification No. 2,448,828, α-hydrocarbon substituted aromatic compounds disclosed in Specification No. 2,722,512, and polynuclear quinone compounds disclosed in Specification No. 3,046,127 and U.S. Patent No. 2,951,758 The combination of triallyl imidazole dimer / p-aminophenyl ketone disclosed in U.S. Patent No. 3,549,367, and benzothiazole-based compound / trihalomethyl disclosed in Japanese Patent Publication No. 51-48516 Homotriazine-based compounds and the like.

The photopolymerization initiator is preferably 0.01 to 50% by weight, more preferably 1 to 30% by weight, and particularly preferably 1 to 20% with respect to the total weight of the solid component in the curable composition containing the quantum dots of the present invention. weight%. When the photopolymerization initiator is lower than the above range, it is difficult to perform polymerization. When the photopolymerization initiator exceeds the above range, although the polymerization rate becomes large, the molecular weight becomes low. The film strength sometimes becomes weak.

The curable composition containing a quantum dot of the present invention can further include a thermal polymerization inhibitor. Examples include hydroquinone, p-methoxyphenol, di-third-butyl-p-cresol, pyrogallol, third butylcatechol, benzoquinone, 4,4'-thiobis (3- Methyl-6-tert-butylphenol), 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2-mercaptobenzimidazole, and the like.

The curable composition containing a quantum dot of the present invention can further include a naphthoquinonediazide-based compound when the curable composition containing a quantum dot is formed in a positive type. Examples of the naphthoquinonediazide compound include o-naphthoquinonediazide-5-sulfonate or sulfonamide, or o-naphthoquinonediazide-4-sulfonate, or sulfonamide. These esters or amidines can be produced by a known method using, for example, the phenol compound described in Japanese Patent Application Laid-Open No. 2-84650 and Japanese Patent Application Laid-Open No. 3-49437 with the chemical formula 1.

The alkali-soluble phenol resin and the crosslinking agent are usually dissolved at a ratio of approximately 2 to 50% by weight and approximately 2 to 30% by weight with respect to the entire mass in the solvent. The naphthoquinonediazide-based compound and the dye are usually added at a ratio of about 2 to 30% by weight and about 2 to 50% by weight, respectively, with respect to a solution containing the alkali-soluble resin and the crosslinking agent. In addition, to the resist composition for a color filter, various additives, such as a smoothing agent for providing uniform coatability, can be further added in the above-mentioned technical fields.

The curable composition containing a quantum dot of the present invention can contain a solvent, and the solvent is not particularly limited. It is particularly preferable to select a solvent in consideration of the solubility, coatability, and safety of the quantum dot and the adhesive.

The above solvents are preferably esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, Ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, methoxyl Ethyl acetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc .; 3-oxypropionate methyl, 3-oxypropionate, etc. Acid alkyl esters, such as 3-methyl Methyloxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc .; methyl 2-oxypropionate, 2-oxo Alkyl 2-oxypropionates such as ethyl propionate, propyl 2-oxypropionate, such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, 2-methylpropionate Propyl oxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, 2-oxy-2-methyl Ethyl propionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc .; methyl pyruvate, ethyl pyruvate, propyl pyruvate , Methyl ethyl acetate, ethyl ethyl acetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, etc .; ethers, such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene dioxane Alcohol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether Ether, propylene glycol methyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, etc .; ketones, such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3- Heptanone and the like; aromatic hydrocarbons, such as toluene, xylene and the like.

Among them, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, and butyl acetate are more preferable. , Methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, propylene glycol methyl ether acetate, and the like.

The curable composition containing a quantum dot of the present invention can further contain various additives such as a filler, a polymer compound other than the above, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber, an anticoagulant, and the like.

Specific examples of the various additives mentioned above include fillers such as glass and alumina; polymers other than adhesive resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, and polyfluoroalkyl acrylate. Compounds; non-ionic, cationic, anionic surfactants; vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri (2-methoxyethoxy) silane, N- ( 2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyl Triethoxy Silane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxy Silane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. Adhesion promoter; 2,2-thiobis (4-methyl-6-tert-butylphenol), 2,6-di-tert-butylphenol and other antioxidants; 2- (3-tert-butylphenol) UV-absorbing agents such as methyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenone; and anticoagulants such as sodium polyacrylate.

In addition, in order to further improve the developability of the curable composition containing the dye of the present invention in order to promote the alkali solubility of the non-image portion, an organic carboxylic acid may be used for the composition, and a molecular weight of 1,000 or less is preferred. Addition of low molecular weight organic carboxylic acids.

Specific examples include aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, hexanoic acid, diethylacetic acid, heptanoic acid, and octanoic acid; oxalic acid, malonic acid, and the like Acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brasilic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid Aliphatic dicarboxylic acids such as acids, methylsuccinic acid, tetramethylsuccinic acid, citraconic acid; aliphatic tricarboxylic acids such as malonic acid, aconitic acid, and camphoric acid; benzoic acid, phenylacetic acid, cumic acid, Aromatic monocarboxylic acids such as dimethyl benzoic acid and milinic acid; phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimellitic acid, trimellitic acid, pyromellitic acid And other aromatic polycarboxylic acids; phenylacetic acid, hydrogenated atoric acid, hydrogenated cinnamic acid, picric acid, phenylsuccinic acid, atropic acid, cinnamic acid, methyl cinnamate, benzyl cinnamate, cinnamoacetic acid, Coumaric acid, umbellic acid and other carboxylic acids.

The present invention provides a color filter manufactured from the curable composition containing the quantum dot.

When the color filter of the present invention is applied to an image display device, it emits light by light from a light source of the display device, so that it can achieve excellent light efficiency. In addition, since colored light is emitted, color reproducibility is excellent, and light is emitted in all directions by photoluminescence, so that the viewing angle can also be improved.

The color filter includes a substrate and a pattern layer formed on the substrate.

As for the substrate, the color filter itself may be a substrate, or may be a portion where the color filter is located in a display device or the like, and is not particularly limited. The substrate may be a glass substrate, a silicon (Si) substrate, a silicon oxide (SiO _x ) substrate, or a polymer substrate, and the polymer substrate may be polyethersulfone (PES) or polycarbonate (PC). .

The pattern layer is a layer containing the curable composition containing the quantum dots of the present invention, and may be a layer formed by coating the curable composition containing the quantum dots and exposing, developing, and thermally curing in a predetermined pattern.

The pattern layer formed from the quantum dot-containing curable composition may include a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles. When light is irradiated, the red pattern layer emits red light, the green pattern layer emits green light, and the blue pattern layer emits blue light.

When applied to an image display device in this case, the light emitted from the light source is not particularly limited, and a light source that emits blue light may be used in terms of excellent color reproducibility.

According to another embodiment of the present invention, the pattern layer may include only two color pattern layers among a red pattern layer, a green pattern layer, and a blue pattern layer. In such a case, the pattern layer further includes a transparent pattern layer that does not contain quantum dot particles.

In the case where the pattern layer has only two colors, a light source that emits light having a wavelength of a remaining color that is not included can be used. For example, when a red pattern layer and a green pattern layer are included, a light source that emits blue light may be used. In such cases, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer directly transmits blue light to show blue.

The color filter including the substrate and the pattern layer may further include a spacer formed between each pattern, and may further include a black matrix. In addition, it may further include a protective film formed on an upper portion of the pattern layer of the color filter.

In addition, the present invention provides an image display device including the color filter.

The color filter of the present invention can be applied not only to a conventional liquid crystal display device, but also to It is applied to various image display devices such as electroluminescence display devices, plasma display devices, and field emission display devices.

The image display device of the present invention may include a color filter including a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles. In such cases, when applied to an image display device, the light emitted from the light source is not particularly limited. In view of excellent color reproducibility, a light source that emits blue light is preferably used.

According to another embodiment of the present invention, the image display device of the present invention may include a color filter including only two color pattern layers among a red pattern layer, a green pattern layer, and a blue pattern layer. In such a case, the color filter further includes a transparent pattern layer containing no quantum dot particles.

In the case where the pattern layer has only two colors, a light source that emits light having a wavelength of a remaining color that is not included can be used. For example, when a red pattern layer and a green pattern layer are included, a light source that emits blue light may be used. In such cases, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer directly transmits blue light to show blue.

The image display device of the present invention is excellent in light efficiency, exhibits high brightness, excellent color reproducibility, and has a wide viewing angle.

In the following, in order to help the understanding of the present invention, preferred embodiments are provided, but these embodiments are only examples of the present invention, and do not limit the scope of patent application. Those skilled in the art should be clear that Within the scope, various changes and modifications to the embodiments can be made, and such changes and modifications should also be included in the scope of patent application.

Manufacturing Example 1. Synthesis of Photoluminescence Green Quantum Dot Particles A with CdSe (Core) / ZnS (Shell) Structure

Add CdO (0.4mmol), zinc acetate (4mmol) and oleic acid (5.5mL) together with 1-octadecene (20mL) into the reactor and heat to 150 ° C Make it react. Thereafter, in order to remove the acetic acid generated by replacing oleic acid with zinc, the above reaction was placed under a vacuum of 100 mTorr for 20 minutes. Then, heat was applied at 310 ° C to obtain a transparent mixture. After maintaining the mixture at 310 ° C for 20 minutes, 0.4 mmol of Se powder and 2.3 mmol of S powder were dissolved in 3 mL of trioctylphosphine. The Se and S solutions were quickly injected into a reactor containing Cd (OA) ₂ and ZN (OA) ₂ solutions. After the thus-obtained mixture was allowed to grow at 310 ° C for 5 minutes, the growth was interrupted using an ice bath. Then, it was precipitated with ethanol, the quantum dots were separated by a centrifugal separator, and excess impurities were washed with chloroform and ethanol, so that the sum of the core particle diameter and shell thickness stabilized by oleic acid was 3 Quantum dot particle A with CdSe (core) / ZnS (shell) structure of ~ 5nm particles.

Production Example 2-1. Synthesis of Alkali-Soluble Resin (D-1)

182 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. The atmosphere in the flask was filled with nitrogen from the air, and the temperature was raised to 100 ° C. 68.8 g of methacrylic acid, 36.4 g of cyclohexyl methacrylate and 136 g of propylene glycol monomethyl ether acetate, a solution containing 3.2 g of tert-butylperoxy-2-ethylhexyl carbonate was added from a dropping funnel through 2 The flask was dropped into the flask for 1 hour, and further stirred at 100 ° C for 5 hours. Next, the atmosphere in the flask was replaced with nitrogen from air, 71 g of glycidyl methacrylate, 0.9 g of tris (dimethylaminomethyl) phenol, and 0.145 g of hydroquinone were put into the flask, and the reaction was continued at 110 ° C. In 6 hours, resin D-1 having an acid value of 100 mgKOH / g as a solid content was obtained. The polystyrene-equivalent weight average molecular weight measured by GPC was 17,000, and the molecular weight distribution (Mw / Mn) was 2.2. The glass transition temperature was measured with a differential scanning calorimeter, and it was 120 ° C.

Production Example 2-2. Synthesis of alkali-soluble resin (D-2)

182 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. The atmosphere in the flask was filled with nitrogen from the air, and the temperature was raised to 100 ° C. 68.8 g of acrylic acid, 44.0 g of monomethacrylate (FA-513M, manufactured by Hitachi Chemical Co., Ltd.) and propylene glycol monomethyl 136 g of ether acetate, and a solution containing 3.2 g of tert-butylperoxy-2-ethylhexyl carbonate was dropped into the flask from the dropping funnel over 2 hours, and further stirred at 100 ° C for 5 hours. Next, the atmosphere in the flask was replaced with nitrogen from air, 71 g of glycidyl methacrylate, 0.9 g of tris (dimethylaminomethyl) phenol, and 0.145 g of hydroquinone were put into the flask, and the reaction was continued at 110 ° C. In 6 hours, resin D-2 having an acid value of 110 mgKOH / g as a solid content was obtained. The polystyrene-equivalent weight average molecular weight measured by GPC was 15,300, and the molecular weight distribution (Mw / Mn) was 2.3. The glass transition temperature was measured with a differential scanning calorimeter, and it was 130 ° C.

Production Example 2-3. Synthesis of Alkali-Soluble Resin (D-3)

182 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. The atmosphere in the flask was filled with nitrogen from the air, and the temperature was raised to 100 ° C. 47.3 g of acrylic acid, 99.9 g of 1-propenyloxy-3-hydroxyadamantane (Audrich Co., Ltd.) and 300 g of propylene glycol monomethyl ether acetate, to which tertiary butyl peroxide-2- A solution of 3.2 g of ethylhexyl carbonate was dropped into the flask from the dropping funnel over 2 hours, and stirred at 100 ° C for 5 hours. Next, the atmosphere in the flask was replaced with nitrogen from air, and 35.5 g of glycidyl methacrylate, 0.9 g of tris (dimethylaminomethyl) phenol, and 0.145 g of hydroquinone were put into the flask, and the temperature was continued at 110 ° C. After 6 hours of reaction, resin D-3 having an acid value of 95 mgKOH / g as a solid content was obtained. The polystyrene-equivalent weight average molecular weight measured by GPC was 18,300, and the molecular weight distribution (Mw / Mn) was 2.3. The glass transition temperature was measured with a differential scanning calorimeter, and it was 160 ° C.

Production Example 2-4. Synthesis of alkali-soluble resin (D-4)

250 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 100 ° C, and then 25.8 g of acrylic acid, 50.4 g of 1-propenyloxy-3-hydroxyadamantane (Audrich Co., Ltd.), 56.7 g of allylbenzene, and 110 g of propylene glycol monomethyl ether acetate A solution of 3.6 g of diisobutyronitrile was dropped into the flask from the dropping funnel over 2 hours, and further stirred at 100 ° C for 5 hours to obtain the acid value of the solid component. 115 mgKOH / g of resin D-4. The polystyrene-equivalent weight average molecular weight measured by GPC was 19,000, and the molecular weight distribution (Mw / Mn) was 2.3. The glass transition temperature was measured with a differential scanning calorimeter, and it was 160 ° C.

Production Example 2-5. Synthesis of alkali-soluble resin (D-5)

250 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 100 ° C, and then 25.8 g of acrylic acid, 44.4 g of 1-propenyloxy-3-hydroxyadamantane (Aldrich Corporation), 44.8 g of allylbenzene, 10.0 g of methacrylic acid, and propylene glycol monomethyl ether acetic acid 110 g of ester, a solution to which 3.6 g of azobisisobutyronitrile was added was dropped into the flask from the dropping funnel over 2 hours, and further stirred at 100 ° C. for 5 hours to obtain a resin D- with a solid content of 115 mgKOH / g 5. The polystyrene-equivalent weight average molecular weight measured by GPC was 19,000, and the molecular weight distribution (Mw / Mn) was 2.2. The glass transition temperature was measured with a differential scanning calorimeter, and it was 135 ° C.

Production Example 2-6. Synthesis of alkali-soluble resin (D-6)

250 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 100 ° C, and then 25.8 g of acrylic acid, 18.8 g of 2-norbornene, 44.8 g of allylbenzene, 10.0 g of methacrylic acid and 110 g of propylene glycol monomethyl ether acetate, and a solution containing 3.6 g of azobisisobutyronitrile The mixture was dropped into the flask from the dropping funnel over 2 hours, and further stirred at 100 ° C. for 5 hours to obtain resin D-6 having a solid content acid value of 105 mgKOH / g. The polystyrene-equivalent weight average molecular weight measured by GPC was 16,300, and the molecular weight distribution (Mw / Mn) was 2.4. The glass transition temperature was measured with a differential scanning calorimeter, and it was 150 ° C.

Production Example 2-7. Synthesis of alkali-soluble resin (D-7)

180 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube, and the atmosphere in the flask was filled with air. After forming nitrogen, the temperature was raised to 80 ° C, and then 20.0 g of methacrylic acid, 55.2 g of n-butyl acrylate, 30 g of glycidyl methacrylate, and 71 g of propylene glycol monomethyl ether acetate were added. A solution of 3.2 g of butylperoxy-2-ethylhexyl carbonate was dropped into the flask from the dropping funnel over a period of 2 hours and stirred at 100 ° C for 5 hours. Next, the atmosphere in the flask was replaced with nitrogen from air, and 36.0 g of methacrylic acid, 0.9 g of tris (dimethylaminomethyl) phenol, and 0.145 g of hydroquinone were put into the flask, and reacted at 100 ° C. for 6 hours. After that, the temperature of the reaction solution was lowered to normal temperature, 4.5 parts of succinic anhydride was added, and the mixture was reacted at 80 ° C. for 6 hours to obtain resin D-7 having an acid value of 80 mgKOH / g as a solid content. The polystyrene equivalent weight average molecular weight measured by GPC was 15,200, and the molecular weight distribution (Mw / Mn) was 2.1. The glass transition temperature was measured with a differential scanning calorimeter, and it was -1.3 ° C.

Production Example 2-8. Synthesis of alkali-soluble resin (D-8)

180 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 80 ° C, and then charged into a flask. 20.0 g of methacrylic acid, 55.2 g of 2-ethylhexyl acrylate, 30 g of glycidyl methacrylate, and 71 g of propylene glycol monomethyl ether acetate, and a third butyl peroxy-2-ethylhexyl group will be added A solution of 3.2 g of carbonate was dropped into the flask from the dropping funnel over 2 hours and stirred at 100 ° C for 5 hours. Next, the atmosphere in the flask was replaced with nitrogen from the atmosphere, 36.0 g of methacrylic acid, 0.9 g of tris (dimethylaminomethyl) phenol, and 0.145 g of hydroquinone were put into the flask, and reacted at 100 ° C. for 6 hours. Thereafter, the temperature of the reaction solution was lowered to normal temperature, 4.5 parts of succinic anhydride was added, and the reaction was performed at 80 ° C. for 6 hours to obtain resin D-8 having an acid value of 45 mgKOH / g as a solid content. The polystyrene-equivalent weight average molecular weight measured by GPC was 7,500, and the molecular weight distribution (Mw / Mn) was 2.1. The glass transition temperature was measured with a differential scanning calorimeter, and it was -19.3 ° C.

Production Example 2-9. Synthesis of alkali-soluble resin (D-9)

182 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube, and the atmosphere in the flask was filled with air. After the formation of nitrogen, the temperature was raised to 100 ° C, and then 105.7 g of benzyl methacrylate, 17.2 g of methacrylic acid, 26.0 g of 2-hydroxyethyl methacrylic acid, and 136 g of propylene glycol monomethyl ether acetate were added. A solution of 3.6 g of azobisisobutyronitrile was dropped into the flask from the dropping funnel over 2 hours, and further stirred at 100 ° C. for 3 hours to obtain resin D-9 having an acid value of 60 mgKOH / g as a solid component. The polystyrene-equivalent weight average molecular weight measured by GPC was 18,000, and the molecular weight distribution (Mw / Mn) was 2.2. The glass transition temperature was measured with a differential scanning calorimeter, and it was 80 ° C.

Production Example 2-10. Synthesis of alkali-soluble resin (D-10)

To a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube, 182 g of propylene glycol monomethyl ether acetate was charged. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 100 ° C, and then benzyl was charged. 105.7 g of methacrylic acid esters, 34.4 g of methacrylic acid, and 136 g of propylene glycol monomethyl ether acetate, a solution containing 3.6 g of azobisisobutyronitrile was dropped from a dropping funnel into a flask over 2 hours, and the temperature was 100 ° C. After further stirring for 3 hours, a resin D-10 having an acid value of 130 mgKOH / g as a solid content was obtained. The polystyrene-equivalent weight average molecular weight measured by GPC was 17,000, and the molecular weight distribution (Mw / Mn) was 2.2. The glass transition temperature was measured with a differential scanning calorimeter, and it was 100 ° C.

Production Example 2-11. Synthesis of alkali-soluble resin (D-11)

182 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 100 ° C, and then charged to 76.8 g of butyl methacrylate, 17.2 g of methacrylic acid, 26.0 g of 2-hydroxyethyl methacrylic acid, and 136 g of propylene glycol monomethyl ether acetate, and a solution containing 3.6 g of azobisisobutyronitrile was added from a dropping funnel The flask was dropped into the flask over 2 hours, and further stirred at 100 ° C for 3 hours to obtain a resin D-11 having an acid value of 62 mgKOH / g as a solid content. The polystyrene equivalent weight average molecular weight measured by GPC was 15,500, and the molecular weight distribution (Mw / Mn) was 2.2. The glass transition temperature was measured with a differential scanning calorimeter, and it was -20 ° C.

Production Example 2-12. Synthesis of alkali-soluble resin (D-12)

100 g of propylene glycol monomethyl ether acetate was added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the atmosphere in the flask was filled with nitrogen from air, the temperature was raised to 80 ° C. -10.2 g of ethylhexyl acrylate, 0.7 g of 4-methylstyrene, 76 g of glycidyl methacrylate, 3 g of n-dodecyl mercaptan, and 100 g of propylene glycol monomethyl ether, with azodiisobutyl added A solution of 5 g of nitrile was dropped into the flask from the dropping funnel over 2 hours, and further stirred at 80 ° C for 4 hours. Next, the atmosphere in the flask was replaced with nitrogen from air, and 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol, and 10.4 g of acrylic acid were placed in the flask, and reacted at 100 ° C. for 6 hours. After that, the temperature of the reaction solution was lowered to normal temperature, and 2.7 g of succinic anhydride was charged and reacted at 80 ° C. for 6 hours to obtain resin D-12 having a solid content acid value of 16.45 mgKOH / g. The polystyrene-equivalent weight average molecular weight measured by GPC was 5450, and the molecular weight distribution (Mw / Mn) was 2.1. The glass transition temperature was measured with a differential scanning calorimeter, and it was -28.4 ° C.

Examples 1 to 8 and Comparative Examples 1 to 4: Production of a self-luminous photosensitive resin composition

As described in Tables 1 and 2 below, the components were mixed, and then diluted with propylene glycol monomethyl ether acetate so that the total solid content was 20% by weight, and then sufficiently stirred to obtain a self-luminous photosensitive resin composition.

Manufacturing Example of Color Filter (Glass Substrate)

A color filter was manufactured using the self-luminous photosensitive resin composition manufactured by the said Example 1-8 and the comparative examples 1-4. That is, each of the above self-luminous photosensitive resin compositions was applied to a glass substrate by a spin coating method, then placed on a hot plate, and maintained at a temperature of 100 ° C. for 3 minutes to form a thin film. Next, a test mask having a square transmission pattern of length × width 20 mm × 20 mm and a line / gap pattern of 1 μm to 100 μm was placed on the above film to The distance from the test mask was 100 μm, and the ultraviolet rays were irradiated.

At this time, the ultra-high pressure mercury lamp (trade name USH-250D) manufactured by USHIO Electric Co., Ltd. was used as the ultraviolet light source, and the light was irradiated with an exposure amount (365 nm) of 200 mJ / cm ² in the atmosphere, without using a special optical filter. . The ultraviolet-irradiated film was immersed in a KOH aqueous solution developing solution at pH 10.5 for 80 seconds to develop. The glass plate with the film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 150 ° C. for 10 minutes to produce a color filter pattern. The film thickness of the self-emitting colored pattern manufactured as described above was 3.0 μm.

Measurement of fine patterns

The size of a pattern obtained by masking a 100 μm line / gap pattern through a color filter formed with the above-mentioned self-emitting pixels was measured by an OM device (ECLIPSE LV100POL, manufactured by Nikon Corporation).

Fine pattern (△ μm) = (line / gap pattern mask size, 100μm)-(measured pixel pattern size)

If the value of the fine pattern is larger than 10 μm, it is difficult to realize fine pixels, and if it has a negative value, process defects may be caused.

Measurement of luminous intensity (Intensity)

For a pattern portion formed by a square pattern of 20 mm × 20 mm among the color filters in which the above-mentioned self-emitting pixels are formed, a 365 nm tube-shaped 4W UV irradiator (VL-4LC, VILBER LOURMAT) is used to measure the area where the light changes, The luminous intensity (Intensity) in the 550 nm region of Examples 1 to 8 and Comparative Examples 1 to 4 was measured with a spectrometer (manufactured by Ocean Optics). It can be judged that the higher the measured luminous intensity (Intensity), the more excellent self-luminescence characteristics are exhibited. The measurement results of luminous intensity (Intensity) are shown in Table 3 below. In addition, a hard bake was performed at 230 ° C for 60 minutes, and the luminous intensity (Intensity) before the hard bake and the luminous intensity (Intensity) after the hard bake were measured to confirm the level of maintaining the luminous efficiency. Expressed as the luminous intensity maintenance rate.

As shown in Table 3, by including the binders used in Examples 1 to 8 provided in the present invention, the luminous intensity and luminous intensity maintenance rate are increased, fine patterns can be made, and high-resolution color filters can be obtained. Excellent photosensitive resin composition of the device.

With reference to Comparative Examples 1 to 3 and Examples 1 to 8, in the case of using an adhesive having a double bond at the end, having cross-linking ability, and compatible with the quantum dot and the ligand on the surface of the quantum dot, the following effects can be confirmed: It acts as a protective group on the surface of the quantum dot, so it has excellent luminous intensity and small extinction amplitude in the process. In addition, referring to Comparative Example 4 and Examples 7 to 8, it was confirmed that even if the luminous intensity is high, a fine pattern with a high resolution cannot be formed when the glass transition temperature (Tg) is -20 ° C or lower, so it cannot be applied.

Claims (6)

A curable composition containing quantum dots, which comprises a binder and quantum dots, and the binder comprises one or more of the following Chemical Formula 1, Chemical Formula 2, and a combination thereof: In the chemical formula 1, R ₁ represents hydrogen or C1-C6 alkyl, and R ₂ represents oxygen, -NH- or R ₃ represents C1 ~ C30 alkylene, C1 ~ C30 alkyleneoxy or C1 ~ C30 ethyloxycarbonylaminoethyl, R ₄ represents a group containing an unsaturated double bond, In this Chemical Formula 2, each of R ₅ to R _{6 is} independently the same or different from each other, and represents hydrogen or a C1 to C6 alkyl group, and R ₇ represents oxygen, -NH- or R ₈ represents C1 ~ C30 alkylene, C1 ~ C30 alkyleneoxy or C1 ~ C30 ethyloxycarbonylaminoethyl, R ₉ represents a group containing an unsaturated double bond, and X represents 0 < The value of X <100; the glass transition temperature of this adhesive is -20 ~ 250 ℃. For example, the curable composition containing quantum dots according to claim 1, wherein 10 to 90% by weight of the adhesive and 3 to 80% by weight are included with respect to the total weight part of the solid content in the quantum dot-containing curable composition The quantum dot includes, as a remaining portion, a photopolymerization compound and a photopolymerization initiator. For example, the curable composition containing quantum dots according to claim 1, wherein the quantum dots are red quantum dots, green quantum dots, or blue quantum dots. The curable composition comprising a quantum dot according to claim 1, wherein the core of the quantum dot comprises a member selected from the group consisting of CdSe, CdS, ZnS, ZnSe, ZnTe, CdTe, CdSeTe, CdZnS, PbSe, AgInZnS, HgS, HgSe, HgTe, GaN , GaP, GaAs, InP, InAs, and ZnO are one or more substances, and the shell includes one or more substances selected from the group consisting of CdSe, ZnSe, ZnS, ZnTe, CdTe, PbS, TiO, SrSe, and HgSe. A color filter manufactured from a curable composition containing a quantum dot according to any one of claims 1 to 4. An image display device, comprising a color filter according to claim 5.