JP2019532918A - Novel compound, core-shell dye, photosensitive resin composition containing the same, and color filter - Google Patents

Abstract

A compound represented by a specific chemical formula, a core containing the compound; and a core-shell dye containing a shell surrounding the core; a photosensitive resin composition containing the compound; and a color produced using the photosensitive resin composition A filter is provided.

Description

  The present description relates to a novel compound, a core-shell dye, a photosensitive resin composition containing the same, and a color filter produced using the same.

  A liquid crystal display device, one of the display devices, has advantages such as light weight, thinness, low price, low power consumption, and excellent integrated circuit connectivity, and is suitable for notebook computers, monitors and TV images. Its range of use is expanding. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, an active circuit unit including a liquid crystal layer, a thin film transistor, and a storage capacitor layer, and an ITO pixel electrode. And an upper substrate. The color filter includes a black matrix layer formed in a pattern defined on a transparent substrate to shield a boundary between pixels, and a plurality of colors, usually red (R), to form each pixel. The pixel portion in which the three primary colors of green (G) and blue (B) are arranged in a predetermined order is sequentially stacked.

  The pigment dispersion method, which is one of the methods for realizing a color filter, coats a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix and exposes a pattern in a form to be formed. After that, the colored thin film is formed by repeating a series of processes in which the non-exposed portion is removed with a solvent and thermally cured. The colored photosensitive resin composition used for the production of a color filter by the pigment dispersion method is generally composed of an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method is actively applied to manufacture LCDs for mobile phones, notebook computers, monitors, TVs and the like. However, recently, not only excellent pattern characteristics but also improved performance is demanded in photosensitive resin compositions for color filters using a pigment dispersion method having various advantages. In particular, high luminance and high contrast ratio characteristics are urgently required along with a high color reproduction rate.

  An image sensor refers to a video imaging device component that generates video using a mobile phone camera, a DSC (digital still camera), and the like. Depending on the manufacturing process and application method, the image sensor is largely divided into a solid coupled device (CCD) image. The sensor is divided into a complementary metal oxide semiconductor (CMOS) image sensor. A color image sensor used for a solid-state image sensor or a complementary metal oxide semiconductor is a color filter having a filter segment of an additive color mixture of red (green) and blue (blue) on a light receiving element. In general, color separation is performed by providing (color filters). Recently, the pattern size of a color filter mounted on such a color image sensor is 2 μm or less, which is 1/100 to 1/200 times that of an existing LCD color filter pattern. Accordingly, an increase in resolution and a decrease in residue are important items that influence the performance of the device.

  In a color filter manufactured with a pigment-type photosensitive resin composition, there is a limit of luminance and light / dark ratio due to pigment particle size. In the case of a color image sensor for an image sensor, a smaller dispersed particle size is required for forming a fine pattern. In order to meet these demands, a dye that does not form particles instead of pigments is introduced to produce a photosensitive resin composition suitable for the dye, thereby achieving a color filter with improved brightness and contrast ratio. There was an attempt to do. However, in the case of dyes, there is a concern about a decrease in luminance due to inferior durability such as pigment contrast, light resistance and heat resistance.

  One embodiment provides a novel compound with excellent brightness and contrast ratio.

  Another embodiment provides a core-shell dye comprising the novel compound.

  Yet another embodiment provides a photosensitive resin composition comprising the novel compound or core-shell dye.

  Yet another embodiment provides a color filter manufactured using the photosensitive resin composition.

  One embodiment provides a compound represented by Formula 1 below.

In Formula 1,
L ¹ and L ² are each independently a substituted or unsubstituted C1-C20 alkylene group,
R ¹ and R ² are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C6-C20 aryl group,
R ³ and R ⁴ are each independently a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted C6-C20 aryl group.

R ¹ and R ² are each independently represented by the following chemical formula 2 or chemical formula 3.

In Formula 2 and Formula 3,
A is a C3-C20 cycloalkane ring or a benzene ring,
L ³ is a substituted or unsubstituted C1-C10 alkylene group,
R ⁵ is a hydrogen atom or a substituted or unsubstituted C1~C10 alkyl group.

In Formula 1, R ³ and R ⁴ may each independently be a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group substituted or unsubstituted with a C1-C10 alkyl group.

  The compound represented by the chemical formula 1 is represented by any one selected from the group consisting of compounds represented by the following chemical formula 1-1 to chemical formula 1-8.

Another embodiment provides a core-shell dye comprising a core comprising the compound represented by Formula 1; and a shell surrounding the core.
The shell is represented by the following chemical formula 4 or chemical formula 5.

In Formula 4 and Formula 5,
L ^{a to} L ^d are each independently a single bond or a substituted or unsubstituted C ^{1 to} C 10 alkylene group.

The L ^{a to} L ^d may be each independently a substituted or unsubstituted C ^{1 to} C 10 alkylene group.

  The shell is represented by the following chemical formula 4-1 or chemical formula 5-1.

  The cage width of the shell may be 6.5 to 7.5 inches.

  The core may have a length of 1 nm to 3 nm.

  The core may have a maximum absorption peak at a wavelength of 530 nm to 680 nm.

  The core-shell dye is represented by any one selected from the group consisting of compounds represented by the following chemical formulas 6 to 21.

  The core-shell dye may include the core and the shell in a molar ratio of 1: 1.

  The core-shell dye may be a green dye.

  Yet another embodiment provides a photosensitive resin composition comprising the compound or core-shell dye.

  The photosensitive resin composition may further include a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

  The photosensitive resin composition may further include a pigment.

  The photosensitive resin composition is 0.5% to 10% by weight of the compound or core-shell dye based on the total amount of the photosensitive resin composition; 0.1% to 30% by weight of the binder resin; And 0.1% to 30% by weight of the photopolymerizable monomer; 0.1% to 5% by weight of the photopolymerization initiator; and the remaining amount of the solvent.

  The photosensitive resin composition includes malonic acid, 3-amino-1,2-propanediol, a silane coupling agent containing a vinyl group or (meth) acryloxy group, a leveling agent, a surfactant, and a radical polymerization initiator. Or a combination thereof.

  Yet another embodiment provides a color filter manufactured using the photosensitive resin composition.

  Other specific matters of the embodiment of the present invention are included in the following detailed description.

  By using the compound or core-shell dye according to one embodiment, a color filter excellent in luminance and contrast ratio can be realized.

It is a figure which shows the cage width (cage width) of the shell represented by Chemical formula 5-1.

  Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereby, and the present invention is defined only by the scope of the claims to be described later.

  In the present specification, unless otherwise specified, “substituted” means that at least one hydrogen atom in a compound is a halogen atom (F, Cl, Br, I), a hydroxy group, a C1-C20 alkoxy group, a nitro group. Group, cyano group, amine group, imino group, azido group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, ether group, carboxyl group or salt thereof, sulfonic acid group or salt thereof , Phosphoric acid or a salt thereof, C1-C20 alkyl group, C2-C20 alkenyl group, C2-C20 alkynyl group, C6-C30 aryl group, C3-C20 cycloalkyl group, C3-C20 cycloalkenyl group, C3-C20 cycloalkynyl Group, C2-C20 heterocycloalkyl group, C2-C20 heterocycloalkenyl group, C ~C20 heterocycloalkynyl group, or means that are substituted with these combinations of substituents.

  In the present specification, unless otherwise specified, the “heterocycloalkyl group”, “heterocycloalkenyl group”, “heterocycloalkynyl group”, and “heterocycloalkylene group” are cycloalkyl, cycloalkenyl, By cycloalkynyl and cycloalkylene ring compounds are meant at least one N, O, S, or P heteroatom.

In the present specification, unless otherwise specified, “(meth) acrylate” means that both “acrylate” and “methacrylate” are possible.
In the present specification, unless otherwise specified, “combination” means mixing or copolymerization.

Unless otherwise defined in the chemical formulas in this specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded at the position.
In the present specification, unless otherwise specified, “*” means a moiety linked to the same or different atom or chemical formula.

  The compound according to one embodiment is represented by the following chemical formula 1.

In Formula 1,
L ¹ and L ² are each independently a substituted or unsubstituted C1-C20 alkylene group,
R ¹ and R ² are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C6-C20 aryl group,
R ³ and R ⁴ are each independently a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted C6-C20 aryl group.

  The compound represented by Chemical Formula 1 is a compound having excellent green spectral characteristics and a high molar extinction coefficient, and can be used as a green dye. However, due to the inferior durability of the pigment, the luminance may be lowered during the baking process after the color resist is manufactured. The compound which concerns on one Embodiment can improve durability by having a substituent containing a urethane coupling group, and can thereby implement | achieve a color filter of a high brightness | luminance and a high contrast ratio.

In Formula 1, R ¹ and R ² are each independently represented by the following Formula 2 or 3.

In Formula 2 and Formula 3,
A is a C3-C20 cycloalkane ring or a benzene ring,
L ³ is a substituted or unsubstituted C1-C10 alkylene group,
R ⁵ is a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl group.

For example, each of R ¹ and R ² independently represents a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted acrylate group. It may be an alkyl group. For example, the C3-C10 cycloalkyl group may be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or the like, but is not necessarily limited thereto.

In Formula 1, R ³ and R ⁴ may each independently be a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group substituted or unsubstituted with a C1-C10 alkyl group.

  When the compound represented by Chemical Formula 1 is used in the photosensitive resin composition (for example, as a dye), the solubility in a solvent described later may be 5 or more, for example, 5 to 10. The solubility is obtained by the amount (g) of the dye (compound) dissolved in 100 g of the solvent. When the solubility of the compound (eg, dye) is within the above range, compatibility with other components in the photosensitive resin composition, that is, a binder resin, a photopolymerizable monomer, and a photopolymerization initiator described later. In addition, the coloring power can be secured, and the precipitation of the dye can be prevented.

  The compound represented by Formula 1 can have excellent heat resistance. That is, at the time of measurement with a thermogravimetric analyzer (TGA), the thermal decomposition temperature may be 200 ° C. or higher, for example, 200 ° C. to 300 ° C.

  The compound represented by the chemical formula 1 has three resonance structures as shown in the following scheme. In this specification, for the sake of convenience, the compound represented by the chemical formula 1 is shown only in one resonance structure. Only. That is, the compound represented by the chemical formula 1 is represented by any one of the three resonance structures.

  The compound represented by the chemical formula 1 is represented by any one selected from the group consisting of compounds represented by the following chemical formula 1-1 to chemical formula 1-8.

  The core-shell dye according to another embodiment may have a structure including a core and a shell surrounding the core. The core includes the compound represented by Formula 1. Specifically, the shell may be a macrocyclic compound, and the coating layer may be formed while the shell surrounds the compound represented by Formula 1.

  In one embodiment, the shell corresponding to the macrocyclic compound has a structure surrounding the compound represented by the chemical formula 1, that is, a structure in which the compound represented by the chemical formula 1 exists in the macrocycle. As a result, the durability of the core-shell dye can be improved, whereby a color filter with a high luminance and a high contrast ratio can be realized.

  The length of the compound represented by Formula 1 included in or constituting the core may be 1 nm to 3 nm, for example, 1.5 nm to 2 nm. When the compound represented by Formula 1 has a length within the above range, a core-shell dye having a core and a shell structure surrounding the core can be easily formed. In other words, when the compound represented by Chemical Formula 1 has a length within the above range, the shell of the macrocyclic compound is obtained in a structure surrounding the compound represented by Chemical Formula 1. When other compounds not corresponding to the length of the above range are used, it is difficult to expect improvement in durability due to the difficulty of forming a structure in which the shell surrounds the core compound.

  The compound represented by the chemical formula 1 contained in or constituting the core may have a maximum absorption peak at a wavelength of 530 nm to 680 nm. A photosensitive resin composition for a color filter having a high luminance and a high light-to-dark ratio is obtained by using, for example, a green-dye, a core-shell dye using the compound represented by Chemical Formula 1 having the spectral characteristics as a core. Obtainable.

  The shell surrounding the core containing the compound represented by Formula 1 is represented by Formula 4 or 5 below.

In Formula 4 and Formula 5,
L ^{a to} L ^d are each independently a single bond or a substituted or unsubstituted C ^{1 to} C 10 alkylene group.

In Chemical Formula 2 or Chemical Formula 3, L ^{a to} L ^d may each independently be a substituted or unsubstituted C ^{1 to} C 10 alkylene group. In this case, the solubility is excellent, and the shell easily forms a structure surrounding the core containing the compound represented by Formula 1.

  For example, the core-shell dye according to one embodiment includes an oxygen atom of the compound represented by Formula 1 and a hydrogen atom bonded to a nitrogen atom of the shell represented by Formula 4 or Formula 5. Non-covalent bonds, that is, hydrogen bonds can be included.

  The shell is represented by, for example, the following chemical formula 4-1 or chemical formula 5-1.

  The cage width of the shell may be 6.5 to 7.5 inches, and the shell volume may be 10 to 16 inches. In the present application, the cage width is the internal distance of the shell, for example, two different methylene groups linked to each other in the shell represented by the chemical formula 4-1 or the chemical formula 5-1. It means the distance between phenylene groups (see FIG. 1). When the shell has a cage width within the above range, a core-shell dye having a structure surrounding a core containing the compound represented by the chemical formula 1 can be obtained, whereby the core-shell dye is converted into a photosensitive resin. When added to the composition, a color filter having excellent durability and high luminance can be realized.

The core-shell dye may include a core including the compound represented by Formula 1 and the shell in a molar ratio of 1: 1. When the core and the shell are present in the molar ratio, a coating layer (shell) surrounding the core containing the compound represented by Formula 1 is successfully formed.
For example, the core-shell dye is represented by any one selected from the group consisting of compounds represented by the following chemical formulas 6 to 21, but is not necessarily limited thereto.

  The core-shell dye may be used alone as a green dye, or may be used as a mixture with a toning dye.

  Examples of the toning dye include triarylmethane dyes, anthraquinone dyes, benzylidene dyes, cyanine dyes, phthalocyanine dyes, azaporphyrin dyes, indigo dyes, and xanthene dyes.

  The core-shell dye may also be used in admixture with a pigment.

  As the pigment, a red pigment, a green pigment, a blue pigment, a yellow pigment, a black pigment, and the like can be used.

  Examples of the red pigment include C.I. I. Red pigment 254, C.I. I. Red pigment 255, C.I. I. Red pigment 264, C.I. I. Red pigment 270, C.I. I. Red pigment 272, C.I. I. Red pigment 177, C.I. I. Examples thereof include red pigment 89. Examples of the green pigment include C.I. I. Green pigment 36, C.I. I. Green pigment 7, C.I. I. Examples thereof include green pigment 58. Examples of the blue pigment include C.I. I. Blue pigment 15: 6, C.I. I. Blue pigment 15, C.I. I. Blue pigment 15: 1, C.I. I. Blue pigment 15: 2, C.I. I. Blue pigment 15: 3, C.I. I. Blue pigment 15: 4, C.I. I. Blue pigment 15: 5, C.I. I. Examples include copper phthalocyanine pigments such as blue pigment 16. Examples of the yellow pigment include C.I. I. Isoindoline pigments such as yellow pigment 139; I. Quinophthalone pigments such as yellow pigment 138; I. And nickel complex pigments such as yellow pigment 150. Examples of the black pigment include aniline black, perylene black, titanium black, and carbon black. These pigments can be used alone or in admixture of two or more, and are not limited to these examples.

  The pigment is contained in the photosensitive resin composition for a color filter in the form of a dispersion. Such a pigment dispersion may comprise the pigment and a solvent, a dispersant, a dispersion resin, and the like.

  As the solvent, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like can be used. Among these, propylene glycol methyl ether is preferable. Acetate can be used.

  The dispersant aids in uniformly dispersing the pigment in the dispersion and can be used with nonionic, anionic, or cationic dispersants. Specifically, polyalkylene glycol or ester thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, carboxylate, alkylamide alkylene Oxide adducts, alkylamines and the like can be used, and these can be used alone or in admixture of two or more.

  As the dispersion resin, an acrylic resin containing a carboxy group can be used, which not only improves the stability of the pigment dispersion but also improves the patternability of the pixels.

  When the core-shell dye and the pigment are mixed and used, they can be mixed and used at a weight ratio of 1: 9 to 9: 1, specifically, a weight ratio of 3: 7 to 7: 3. . When mixing in the weight ratio range, it is possible to have a high luminance and light / dark ratio while maintaining color characteristics.

  According to another embodiment, a photosensitive resin composition including the compound represented by Formula 1 or the core-shell dye is provided.

  The photosensitive resin composition includes (A) a colorant (the compound represented by the chemical formula 1 or the core-shell dye), (B) a binder resin, (C) a photopolymerizable monomer, and (D) light. A polymerization initiator and (E) a solvent can be included.

  Hereinafter, each component will be specifically described.

(A) Colorant The colorant may include the compound represented by the chemical formula 1 and / or the core-shell dye, and the compound represented by the chemical formula 1 and / or the core-shell dye may be included. As described above.

  The colorant may further contain a pigment in addition to the compound represented by Formula 1 and / or the core-shell dye, and the pigment has been described above.

  The compound represented by Chemical Formula 1 and / or the core-shell dye is 0.5 wt% to 10 wt%, for example, 0.5 wt% to the total amount of the photosensitive resin composition for color filters. 5% by weight is included. When the core-shell dye is used within the above range, a high luminance and light / dark ratio can be developed at a desired color coordinate.

(B) Binder resin The binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and one or more acrylic repeating units. It may be a resin.

  The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxy groups. Specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid. An acid or a combination thereof can be mentioned.

  The first ethylenically unsaturated monomer is included in an amount of 5% by weight to 50% by weight, for example, 10% by weight to 40% by weight with respect to the total amount of the alkali-soluble resin.

  The second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, α-methylstyrene, vinyl toluene, vinyl benzyl methyl ether; methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate , 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, and the like; 2-aminoethyl ( Unsaturated carboxylic acid aminoalkyl ester compounds such as meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; glycidyl (meth) acrylate and the like Unsaturated carboxylic acid glycidyl ester compounds; vinyl cyanide compounds such as (meth) acrylonitrile; unsaturated amide compounds such as (meth) acrylamide; and the like can be used alone or in admixture of two or more. .

  Specific examples of the binder resin include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / Although a styrene / 2-hydroxyethyl methacrylate copolymer etc. are mentioned, it is not limited to these, These can also be used individually or in mixture of 2 or more types.

The binder resin has a weight average molecular weight of 3,000 g / mol to 150,000 g / mol, such as 5,000 g / mol to 50,000 g / mol, such as 20,000 g / mol to 30,000 g / mol. May be. When the weight average molecular weight of the binder resin is in the above range, the adhesiveness with the substrate is excellent, the physical and chemical properties are good, and the viscosity is appropriate.
The acid value of the binder resin may be 15 mgKOH / g to 60 mgKOH / g, for example, 20 mgKOH / g to 50 mgKOH / g. When the acid value of the binder resin is within the above range, excellent pixel resolution can be obtained.

  The binder resin is included in an amount of 0.1 wt% to 30 wt%, for example, 5 wt% to 20 wt% with respect to the total amount of the photosensitive resin composition. When the binder resin is included in the above range, at the time of producing a color filter, it is excellent in developability, crosslinkability is improved, and excellent surface smoothness can be obtained.

(C) Photopolymerizable monomer As the photopolymerizable monomer, a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond can be used.

  The photopolymerizable monomer has a pattern excellent in heat resistance, light resistance and chemical resistance by having the ethylenically unsaturated double bond and causing sufficient polymerization at the time of exposure in the pattern forming step. Can be formed.

  Specific examples of the photopolymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di ( (Meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) Acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate Dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) Examples include acryloyloxyethyl phosphate and novolac epoxy (meth) acrylate.

An example of a commercial product of the photopolymerizable monomer is as follows. Examples of the monofunctional ester of (meth) acrylic acid include Aronix M-101 ^R , M-111 ^R , M-114 ^{R and the} like from Toa Synthetic Chemical Industry Co., Ltd .; Nippon Kayaku Co., Ltd. KAYARAD TC-110S ^R , TC-120S ^R, etc .; V-158 ^R , V-2311 ^R, etc. of Osaka Organic Chemical Industry Co., Ltd. Examples of the bifunctional ester of (meth) acrylic acid include Aronix M-210 ^R , M-240 ^R , M-6200 ^R, etc. manufactured by Toa Synthetic Chemical Industry Co., Ltd .; Nippon Kayaku Co., Ltd. of KAYARAD HDDA ^R, the HX-220 ^R, the R-604 ^R, and the like; manufactured by Osaka Organic Chemical Industry Co. of ^{V-260 R, V-312} R, and the like V-335HP ^R. Examples of said trifunctional ester of (meth) acrylic acid, Toagosei Chemical Industry Co. of Aronix M-309 ^R, the M-400 ^R, the M-405 ^R, the M-450 ^R, the M -7100 ^R , M-8030 ^R , M-8060 ^R, etc .; Nippon Kayaku Co., Ltd. KAYARAD TMPTA ^R , DPCA-20 ^R , -30 ^R , -60 ^R , -120 ^R, etc. ; Osaka organic Kayaku Kogyo Co. of V-295 ^R, the same -300 ^R, the same -360 ^R, same -GPT ^R, same -3PA ^R, such as the -400 ^R, and the like. These products can be used alone or in combination of two or more.

  The photopolymerizable monomer may be used after being treated with an acid anhydride in order to impart better developability.

  The photopolymerizable monomer is included in an amount of 0.1 wt% to 30 wt%, for example, 5 wt% to 20 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included in the above range, the pattern characteristics and developability are excellent during the production of a color filter.

(D) Photopolymerization initiator As the photopolymerization initiator, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, an oxime compound, or the like can be used.

  Examples of the acetophenone compounds include 2,2′-diethoxyacetophenone, 2,2′-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt -Butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl- And 2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.

Examples of the benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis. (Diethylamino) benzophenone, 4,4′-dimethylaminobenzophenone, 4,4′-dichlorobenzophenone, 3,3′-dimethyl-2-methoxybenzophenone and the like.
Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, and the like.

  Examples of the benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and pendyl dimethyl ketal.

  Examples of the triazine compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) -s-triazine, and 2- (3 ′, 4′-dimethoxystyryl). -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-biphenyl 4,6-bis (trichloromethyl) -s-triazine Bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-me Xylnaphtho-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2-4-trichloromethyl (piperonyl) -6-triazine, 2-4-trichloromethyl (4′-methoxystyryl) -6 Examples include triazine.

  Examples of the oxime compounds include 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (o-acetyloxime) -1- [9- And ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone.

  As the photopolymerization initiator, a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, and the like can be used in addition to the compound.

  The photopolymerization initiator is included in an amount of 0.1 wt% to 5 wt%, for example, 1 wt% to 3 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is included in the above range, photopolymerization occurs sufficiently during exposure in the pattern forming process for producing the color filter, and the sensitivity is excellent and the transmittance is improved.

(E) Solvent The solvent is not particularly limited. Specifically, for example, alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran ; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, propylene glycol methyl ether; cellosolv acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, diethyl cellosolve acetate; methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether , Diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ether Carbitols such as tilether and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; methyl ethyl ketone, cyclohexanone, 4-hydroxy- Ketones such as 4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, 2-heptanone; saturated fats such as ethyl acetate, n-butyl acetate, and isobutyl acetate Monocarboxylic acid alkyl esters; lactic acid alkyl esters such as methyl lactate and ethyl lactate; methyl hydroxyacetate, ethyl hydroxyacetate Hydroxyacetic acid alkyl esters such as butyl hydroxyacetate; Acetic acid alkoxyalkyl esters such as methoxymethyl acetate, methoxyethyl acetate, methoxybutyl acetate, ethoxymethyl acetate, ethoxyethyl acetate; Methyl 3-hydroxypropionate, Ethyl 3-hydroxy 3-hydroxypropionic acid alkyl esters such as propionate; 3-alkoxy such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate Propionic acid alkyl esters; 2-hydrides such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate Xylpropionic acid alkyl esters; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate; methyl 2-hydroxy-2-methylpropionic acid alkyl esters such as 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; methyl 2-methoxy-2-methylpropionate, ethyl 2-alkoxy-2-methylpropionic acid alkyl esters such as 2-ethoxy-2-methylpropionate; 2-hydroxyethylpropionate, 2-hydroxy-2-methylethylpropionate, hydroxyethyl acetate, methyl 2-hydroxy Esters such as -3-methylbutanoate; or compounds of ketonic esters such as ethyl pyruvate, and also N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methyl Acetamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid There are ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc., which are used alone or in combination of two or more. Door can be.

  Considering miscibility and reactivity in the solvent, glycol ethers such as ethylene glycol monoethyl ether; ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; 2-hydroxyethyl pro Esters such as pionate; diethylene glycols such as diethylene glycol monomethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

  The solvent is contained as a balance with respect to the total amount of the photosensitive resin composition, specifically, 20 wt% to 90 wt%. When a solvent is contained in the said range, it is excellent in the applicability | paintability of the photosensitive resin composition, and the outstanding flatness can be maintained with the film | membrane of thickness 3 micrometers or more.

(F) Other Additives The photosensitive resin composition is malonic acid for preventing spots and spots, improving leveling performance, and preventing generation of undeveloped residues at the time of application; 3 -Amino-1,2-propanediol; Silane coupling agent containing a vinyl group or (meth) acryloxy group; Leveling agent; Fluorine surfactant; Radical polymerization initiator and the like may further be included.

  In addition, the photosensitive resin composition may further include an additive such as an epoxy compound in order to improve adhesion to the substrate.

  Examples of the epoxy compound include a phenol novolac epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

  The content of the additive can be easily adjusted according to desired physical properties.

  Yet another embodiment provides a color filter manufactured using the photosensitive resin composition described above. The manufacturing method of the color filter is as follows.

Spin coating, slitting the photosensitive resin composition for color filter described above on a glass substrate on which nothing is applied, or on a glass substrate in which SiN _{x of the} protective film is applied to a thickness of 500 to 1500 mm. Using a suitable method such as coating, the coating is applied to a thickness of 3.1 μm to 3.4 μm. After coating, light is irradiated so as to form a pattern necessary for the color filter. When the coating layer is treated with an alkali developer after irradiation with light, the unirradiated portion of the coating layer is dissolved, and a pattern necessary for the color filter is formed. By repeating this process according to the number of necessary R, G, and B colors, a color filter having a desired pattern can be obtained.

  In the above process, the image pattern obtained by development is reheated or cured by irradiation with actinic radiation to further improve crack resistance, solvent resistance, and the like.

Hereinafter, preferred embodiments of the present invention will be described. However, the following embodiment is only a preferred embodiment of the present invention, and the present invention is not limited to the following embodiment.
(Production of monomolecular compounds)
(Synthesis Example 1: Synthesis of Intermediate A-1)

2,4-Dimethyldiphenylamine (10 mol), 1-Bromo-2- (methoxymethyoxy) ethane (20 mol) and sodium hydride (20 mol) were placed in N, N-dimethylformamide, heated to 80 ° C. and stirred for 24 hours. did. Ethyl acetate was added to this solution and washed twice with water to extract the organic layer. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain Intermediate A-1.
(Synthesis Example 2: Synthesis of Intermediate A-2)

Intermediate A-1 (60 mmol), 3,4-dihydroxy-3-cyclobutene-1,2-dione (30 mmol) were placed in toluene (200 mL) and butanol (200 mL), and the water produced by refluxing was added to Dean. -Removed with a stark distillation apparatus. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain the intermediate A-2.
(Synthesis Example 3: Synthesis of Intermediate A-3)

Intermediate A-2 (5 mmol) was dissolved in 600 mL of a chloroform solvent, and then Isophthalyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL of chloroform and added dropwise at room temperature for 5 hours. After 12 hours, the residue was distilled under reduced pressure and separated by column chromatography to obtain Intermediate A-3.
(Synthesis Example 4: Synthesis of Intermediate A-4)

Intermediate A-2 (5 mmol) is dissolved in 600 mL of chloroform solvent, and then triethylamine (50 mmol) is added. 2,6-pyridined carbon dichloride (20 mmol) and p-xylylene diamine (20 mmol) were dissolved in 60 mL of chloroform and simultaneously dropped at room temperature for 5 hours. After 12 hours, the residue was distilled under reduced pressure and separated by column chromatography to obtain Intermediate A-4.
(Synthesis Example 5: Synthesis of Intermediate B-1)

Intermediate A-3 (5 mmol) and 10% HCl were placed in 200 mL of ethanol: dichloromethane (2: 8) and stirred at 40 ° C. for 24 hours. After stirring, the reaction product was distilled under reduced pressure and purified by column chromatography to obtain the intermediate B-1.
(Synthesis Example 6: Synthesis of Intermediate B-2)

The intermediate B-2 was obtained by synthesizing in the same manner as in Synthesis Example 5 except that the intermediate A-4 was used instead of the intermediate A-3.
(Synthesis Example 7: Synthesis of core-shell dye represented by Chemical Formula 6)

A THF solution (100 mL) to which Intermediate B-1 (5 mmol), cyclohexyl isocynate (8 mmol), and dibutyltin dilaurate catalyst amount were added was stirred for 6 hours under a nitrogen atmosphere. After stirring, the reaction product was distilled under reduced pressure and purified by column chromatography to obtain Chemical Formula 6.
Maldi-tof MS: 1342.65 m / z
(Synthesis Example 8: Synthesis of Core-Shell Dye Represented by Chemical Formula 7)
A compound represented by Chemical Formula 8 was obtained by synthesis in the same manner as in Synthesis Example 7 except that B-2 was used instead of Intermediate B-1.
Maldi-tof MS: 1344.64 m / z
(Synthesis Example 9: Synthesis of core-shell dye represented by Chemical Formula 8)
A compound represented by the chemical formula 8 was obtained by synthesis in the same manner as in Synthesis Example 7 except that 2-Isocyanatoethyl acrylate was used instead of Cyclohexyl isocynate.
Maldi-tof MS: 1375.56 m / z
(Synthesis Example 10: Synthesis of Core-Shell Dye Represented by Chemical Formula 9)
A compound represented by the chemical formula 9 was obtained by synthesis in the same manner as in Synthesis Example 9 except that B-2 was used instead of the intermediate B-1.
Maldi-tof MS: 1378.53 m / z
(Synthesis Example 11: Synthesis of Core-Shell Dye Represented by Chemical Formula 10)
A compound represented by the chemical formula 10 was obtained by synthesis in the same manner as in Synthesis Example 7 except that Methacryloyloxyethyl isocynate was used instead of Cyclohexyl isocynate.
Maldi-tof MS: 1402.60 m / z
Synthesis Example 12 Synthesis of Core-Shell Dye Represented by Chemical Formula 11
A compound represented by the chemical formula 11 was obtained by synthesis in the same manner as in Synthesis Example 11 except that B-2 was used instead of the intermediate B-1.
Maldi-tof MS: 1405.59 m / z
Synthesis Example 13 Synthesis of Core-Shell Dye Represented by Chemical Formula 12
A compound represented by the chemical formula 12 was obtained by synthesis in the same manner as in Synthesis Example 7 except that phenyl isocynate was used instead of cyclohexyl isocynate.
Maldi-tof MS: 1330.55 m / z
Synthesis Example 14 Synthesis of Core-Shell Dye Represented by Chemical Formula 13
The compound represented by Chemical Formula 13 was obtained by synthesizing in the same manner as in Synthesis Example 13 except that B-2 was used instead of Intermediate B-1.
Maldi-tof MS: 1332.54 m / z
(Synthesis Example 15: Synthesis of Intermediate C-1)

2- (Ethylanilino) ethanol (10 mol), Chloromethyl methyl ether (15 mol), and triethylamine (15 mol) were put in dichloromethane and stirred for 24 hours. This solution was distilled under reduced pressure and separated by column chromatography to obtain Intermediate C-1.
(Synthesis Example 16: Synthesis of Intermediate C-2)

Synthesis was performed in the same manner as in Synthesis Example 2 except that Intermediate C-1 was used instead of Intermediate A-1, and Intermediate C-2 was obtained.
(Synthesis Example 17: Synthesis of Intermediate C-3)

  The intermediate C-3 was obtained by synthesis in the same manner as in Synthesis Example 3 except that the intermediate C-2 was used instead of the intermediate A-2.

  (Synthesis Example 18: Synthesis of Intermediate C-4)

The intermediate C-4 was obtained by synthesizing in the same manner as in Synthesis Example 4 except that the intermediate C-2 was used instead of the intermediate A-2.
(Synthesis Example 19: Synthesis of Intermediate D-1)

The intermediate D-1 was obtained by synthesizing in the same manner as in Synthesis Example 5 except that the intermediate C-3 was used instead of the intermediate A-3.
(Synthesis Example 20: Synthesis of Intermediate D-2)

The intermediate D-2 was obtained by synthesis in the same manner as in Synthesis Example 6 except that the intermediate C-4 was used instead of the intermediate A-4.
(Synthesis Example 21: Synthesis of Core-Shell Dye Represented by Chemical Formula 14)

The compound represented by Chemical Formula 14 was obtained by synthesizing in the same manner as in Synthesis Example 7 except that Intermediate D-1 was used instead of Intermediate B-1.
Maldi-tof MS: 1190.58 m / z
Synthesis Example 22 Synthesis of Core-Shell Dye Represented by Chemical Formula 15
The compound represented by Chemical Formula 15 was obtained by synthesis in the same manner as in Synthesis Example 21 except that Intermediate D-2 was used instead of Intermediate D-1.
Maldi-tof MS: 1193.42 m / z
Synthesis Example 23 Synthesis of Core-Shell Dye Represented by Chemical Formula 16
A compound represented by Chemical Formula 16 was obtained by synthesis in the same manner as in Synthesis Example 21, except that 2-Isocyanatoethyl acrylate was used instead of Cyclohexyl isocynate.
Maldi-tof MS: 1222.50 m / z
Synthesis Example 24 Synthesis of Core-Shell Dye Represented by Chemical Formula 17
The compound represented by Chemical Formula 17 was obtained by synthesis in the same manner as in Synthesis Example 23 except that Intermediate D-2 was used instead of Intermediate D-1.
Maldi-tof MS: 1224.49 m / z
(Synthesis Example 25: Synthesis of Core-Shell Dye Represented by Chemical Formula 18)
A compound represented by Formula 18 was obtained by synthesis in the same manner as in Synthesis Example 21 except that Methacryloyloxyethyl isocynate was used instead of Cyclohexylisocynate.
Maldi-tof MS: 1251.40 m / z
(Synthesis Example 26: Synthesis of Core-Shell Dye Represented by Chemical Formula 19)
The compound represented by Chemical Formula 19 was obtained by synthesis in the same manner as in Synthesis Example 25 except that Intermediate D-2 was used instead of Intermediate D-1.
Maldi-tof MS: 1252.52 m / z
Synthesis Example 27 Synthesis of Core-Shell Dye Represented by Chemical Formula 20
A compound represented by the chemical formula 20 was obtained by synthesis in the same manner as in Synthesis Example 21 except that Phenyl isocynate was used instead of Cyclohexyl isocynate.
Maldi-tof MS: 1178.49 m / z
Synthesis Example 28 Synthesis of Core-Shell Dye Represented by Chemical Formula 21
The compound represented by Chemical Formula 21 was obtained by synthesis in the same manner as in Synthesis Example 27 except that Intermediate D-2 was used instead of Intermediate D-1.
Maldi-tof MS: 1180.48 m / z
(Synthesis Example 29: Synthesis of core-shell dye)
After adding 398 mg of squaric acid and 2.23 g of 2- (3- (dibutylamino) phenoxy) ethyl acrylate to a 100 mL 3-neck flask, add 40 mL of n-butanol and 20 mL of toluene, and heat to reflux at 120 ° C. for 5 hours. did. Water generated during the reaction was removed using a Dean-Stark trap set to promote the reaction. After completion of the reaction, the reaction mixture was cooled, extracted with methylene chloride, and subjected to column chromatography to produce a compound represented by the following chemical formula X in a yield of 60%. Thereafter, 0.72 g (1 mmol) of the compound represented by the chemical formula X and 2.02 g of triacetyl beta-cyclodextrin represented by the following chemical formula Y (triacetyl β-cyclodextrin, TCI, CAS # 23739-88-0). (1 mmol) was dissolved in 50 ml of dichloromethane, and after stirring at room temperature for about 12 hours, the solvent was completely removed and dried under reduced pressure to obtain about 2.7 g of a core-shell dye in a solid state. The core-shell dye was obtained as a structure in which the compound represented by the chemical formula X was surrounded by the compound represented by the chemical formula Y.

Synthesis Example 30 Synthesis of Compound Represented by Chemical Formula Z

After adding 398 mg of squaric acid and 2.23 g of 2- (3- (methyl (phenyl) amino) propylamino) ethyl acrylate to a 100 mL 3-necked flask, 40 mL of n-butanol and 20 mL of toluene were added, and 120 ° C. And heated at reflux for 5 hours. Water generated during the reaction was removed using a Dean-Stark trap set to promote the reaction. After completion of the reaction, the reaction mixture was cooled, extracted with methylene chloride, and subjected to column chromatography to synthesize the compound represented by the chemical formula Z in a yield of 60%.
Maldi-tof MS: 514.26 m / z
(Production of photosensitive resin composition)
The specification of the component used for manufacture of the photosensitive resin composition is as follows.

(A) Dye (A-1) Core-shell dye prepared in Synthesis Example 7 (indicated by chemical formula 6)
(A-2) Core-shell dye produced in Synthesis Example 8 (indicated by chemical formula 7)
(A-3) Core-shell dye produced in Synthesis Example 9 (indicated by chemical formula 8)
(A-4) Core-shell dye produced in Synthesis Example 10 (indicated by chemical formula 9)
(A-5) Core-shell dye produced in Synthesis Example 11 (indicated by chemical formula 10)
(A-6) Core-shell dye produced in Synthesis Example 12 (indicated by chemical formula 11)
(A-7) Core-shell dye produced in Synthesis Example 13 (indicated by chemical formula 12)
(A-8) Core-shell dye produced in Synthesis Example 14 (indicated by chemical formula 13)
(A-9) Core-shell dye produced in Synthesis Example 21 (indicated by chemical formula 14)
(A-10) Core-shell dye produced in Synthesis Example 22 (indicated by chemical formula 15)
(A-11) Core-shell dye produced in Synthesis Example 23 (indicated by chemical formula 16)
(A-12) Core-shell dye prepared in Synthesis Example 24 (indicated by chemical formula 17)
(A-13) Core-shell dye prepared in Synthesis Example 25 (indicated by chemical formula 18)
(A-14) Core-shell dye prepared in Synthesis Example 26 (indicated by chemical formula 19)
(A-15) Core-shell dye prepared in Synthesis Example 27 (indicated by chemical formula 20)
(A-16) Core-shell dye produced in Synthesis Example 28 (indicated by chemical formula 21)
(A-17) Core-shell dye produced in Synthesis Example 29 (A-18) Monomolecular dye produced in Synthesis Example 30 (indicated by chemical formula Z)
(A ′) Pigment dispersion (A′-1) C.I. I. Green pigment 7
(A′-2) C.I. I. Green pigment 36
(B) Methacrylic acid / benzyl methacrylate copolymer having a binder resin weight average molecular weight of 22,000 g / mol (mixing weight ratio: 15 wt% / 85 wt%)
(C) Photopolymerizable monomer dipentaerythritol hexaacrylate (D) Photopolymerization initiator (D-1) 1,2-octanedione (D-2) 2-dimethylamino-2- (4-methyl-benzyl) ) -1- (4-Morpholin-4-yl-phenyl) -butan-1-one (E) Solvent (E-1) Cyclohexanone (E-2) Propylene glycol methyl ether acetate Examples 1 to 16 and comparison Example 1 to Comparative Example 4
Each component was mixed with the composition of following Table 1-Table 3, and the photosensitive resin composition was manufactured. Specifically, after dissolving the photopolymerization initiator in the solvent, stirring at room temperature for 2 hours, adding a dye (or pigment dispersion) and stirring for 30 minutes, the binder resin and the photopolymerizable monomer The body was added and stirred at room temperature for 2 hours. The solution was filtered three times to remove impurities to produce a photosensitive resin composition.

(Evaluation)
Evaluation 1: Durability evaluation The photosensitive resin compositions produced in Examples 1 to 16 and Comparative Examples 1 to 4 were applied to a thickness of 1 μm to 3 μm on a degreased and washed 1 mm thick glass substrate. And dried on a hot plate at 90 ° C. for 2 minutes to obtain a coating film. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a dominant wavelength of 365 nm, dried in an oven at 200 ° C. for 20 minutes, and then changed in color coordinates using a spectrophotometer (MCPD3000, Otsuka electronic). The durability was confirmed by measuring the value, and the results are shown in Table 4 below.

Good durability evaluation criteria: Color coordinate change value is 0.005 or less Defective: Color coordinate change value exceeds 0.005

  From Table 4 above, in the case of Examples 1 to 16 including the core-shell dye according to one embodiment, the durability was compared with the cases of Comparative Examples 1 to 4 not including the core-shell dye. It can be seen that has increased.

Evaluation 2: Brightness and light / dark ratio evaluation Photosensitive resin compositions produced in Examples 1 to 16 and Comparative Examples 1 to 4 in a thickness of 1 to 3 μm on a degreased and washed 1 mm thick glass substrate. Was applied and dried on a hot plate at 90 ° C. for 2 minutes to obtain a coating film. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a dominant wavelength of 365 nm, and then dried for 5 minutes in a 200 ° C. hot-air circulating drying furnace. The pixel layer was measured for luminance and contrast ratio using a spectrophotometer (MCPD3000, Otsuka electronic), and the results are shown in Table 5 below.

  From Table 5 above, in the case of Examples 1 to 16 including the core-shell dye according to one embodiment, the brightness is higher than that in Comparative Examples 1 to 4 not including the core-shell dye. It can be confirmed that a high contrast ratio can be obtained.

  The present invention is not limited to the above-described embodiments, and can be manufactured in various forms different from each other. Those having ordinary knowledge in the technical field to which the present invention pertains It will be understood that other specific forms may be implemented without changing essential features. Therefore, it should be understood that the embodiments described above are illustrative in all aspects and are not limiting.

Claims (20)

Compound represented by the following chemical formula 1:
In Formula 1,
L ¹ and L ² are each independently a substituted or unsubstituted C1-C20 alkylene group,
R ¹ and R ² are each independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C6-C20 aryl group,
R ³ and R ⁴ are each independently a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted C6-C20 aryl group. The compound according to claim 1, wherein R ¹ and R ² are each independently represented by the following chemical formula 2 or chemical formula 3:
In Formula 2 and Formula 3,
A is a C3-C20 cycloalkane ring or a benzene ring,
L ³ is a substituted or unsubstituted C1-C10 alkylene group,
R ⁵ is a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl group. The compound according to claim 1, wherein R ³ and R ⁴ are each independently a substituted or unsubstituted C1-C10 alkyl group, or a C6-C20 aryl group substituted or unsubstituted with a C1-C10 alkyl group. . 2. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one selected from the group consisting of compounds represented by the following chemical formulas 1-1 to 1-8.
A core-shell dye comprising a core comprising the compound of claim 1; and a shell surrounding the core. The core-shell dye according to claim 5, wherein the shell is represented by the following chemical formula 4 or chemical formula 5.
(In Formula 4 and Formula 5,
L ^{a to} L ^d are each independently a single bond or a substituted or unsubstituted C1-C10 alkylene group) The core-shell dye according to claim 5, wherein each of L ^{a to} L ^d is independently a substituted or unsubstituted C ^{1 to} C 10 alkylene group. The core-shell dye according to claim 5, wherein the shell is represented by the following chemical formula 4-1 or chemical formula 5-1.
  9. The core-shell dye of claim 8, wherein the shell has a cage width of 6.5 to 7.5 inches.   The core-shell dye according to claim 5, wherein the core has a length of 1 nm to 3 nm.   6. The core-shell dye according to claim 5, wherein the core has a maximum absorption peak at a wavelength of 530 nm to 680 nm. The core-shell dye according to claim 5, wherein the core-shell dye is represented by any one selected from the group consisting of compounds represented by the following chemical formulas 6 to 21.
  6. The core-shell dye of claim 5, wherein the core-shell dye comprises the core and the shell in a 1: 1 molar ratio.   6. The core-shell dye according to claim 5, wherein the core-shell dye is a green dye.   The photosensitive resin composition containing the compound of any one of Claims 1-4, or the core-shell dye of any one of Claims 5-14.   The said photosensitive resin composition is a photosensitive resin composition of Claim 15 which further contains binder resin, a photopolymerizable monomer, a photoinitiator, and a solvent.   The photosensitive resin composition according to claim 16, further comprising a pigment. The photosensitive resin composition is based on the total amount of the photosensitive resin composition.
0.5% to 10% by weight of the compound or core-shell dye;
0.1% to 30% by weight of the binder resin;
0.1% to 30% by weight of the photopolymerizable monomer;
The photosensitive resin composition according to claim 16, comprising 0.1 to 5% by weight of the photopolymerization initiator; and the remaining amount of the solvent.   The photosensitive resin composition includes malonic acid, 3-amino-1,2-propanediol, a silane coupling agent containing a vinyl group or (meth) acryloxy group, a leveling agent, a surfactant, and a radical polymerization initiator. The photosensitive resin composition of Claim 16 which further contains these, or these combination.   A color filter produced using the photosensitive resin composition according to claim 15.