KR102059022B1 - Novel compound, core-shell dye, photosensitive resin composition including the same, and color filter - Google Patents

Abstract

(상기 화학식 1에서, 각 치환기는 명세서에 정의된 바와 같다.)To a compound represented by the formula (1), a core comprising the same; And a core-shell dye comprising a shell surrounding the core, a photosensitive resin composition comprising the same, and a color filter manufactured using the photosensitive resin composition.
[Formula 1]

(In Formula 1, each substituent is as defined in the specification.)

Description

Novel compounds, core-shell dyes, photosensitive resin compositions and color filters comprising the same {NOVEL COMPOUND, CORE-SHELL DYE, PHOTOSENSITIVE RESIN COMPOSITION INCLUDING THE SAME, AND COLOR FILTER}

The present disclosure relates to a novel compound, a core-shell dye, a photosensitive resin composition comprising the same, and a color filter prepared using the same.

The liquid crystal display device, which is one of the display devices, has advantages such as light weight, thinness, low cost, low power consumption, and excellent bonding with an integrated circuit, and thus its use range is expanding for notebook computers, monitors, and TV images. The 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 consisting of a liquid crystal layer, a thin film transistor, and a capacitor capacitor layer, and an upper substrate on which an ITO pixel electrode is formed. The color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate for shielding boundaries between pixels, and a plurality of colors for forming each pixel, typically red (R), green (G), and blue (B). ) Has a structure in which the pixel portions arranged in the predetermined order in the three primary colors are stacked one by one.

The pigment dispersion method, which is a method of implementing a color filter, coats a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix, exposes a pattern of a shape to be formed, and then removes a non-exposed portion with a solvent. It is a method in which a colored thin film is formed by repeating a series of processes of thermosetting. The coloring photosensitive resin composition used for manufacturing the color filter by the pigment dispersion method generally consists of alkali-soluble resin, a photopolymerizable monomer, a photoinitiator, an epoxy resin, a solvent, other additives, etc. The pigment dispersion method is actively applied to manufacture LCDs of mobile phones, notebook computers, monitors, TVs and the like. However, in recent years, in the photosensitive resin composition for color filters using the pigment dispersion method which has various advantages, not only the outstanding pattern property but also the further improved performance are calculated | required. In particular, high luminance and high contrast ratios, along with high color reproduction, are urgently required.

An image sensor refers to a component of an image capturing device that generates an image from a mobile phone camera or a digital still camera (DSC). The image sensor is largely complementary to a solid-state charge coupled device (CCD) image sensor according to its manufacturing process and application method. It may be classified as a complementary metal oxide semiconductor (CMOS) image sensor. The color image pickup device used in the solid state image pickup device or the complementary metal oxide semiconductor includes a color filter including a filter segment of an additive mixed primary color of red, green, and blue on the light receiving device. It is common to install color filters separately and to separate the colors. Recently, the pattern size of the color filter mounted on the color image pickup device has a size of 2 μm or less, which is 1/100 to 1/200 times of the conventional color filter pattern for LCD. Accordingly, the increase in resolution and the reduction of residues are important factors that determine the performance of the device.

In the color filter made of the pigment-type photosensitive resin composition, there are limitations of brightness and contrast ratio resulting from the pigment particle size. In addition, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet these demands, there is an attempt to implement a color filter having improved brightness and contrast ratio by preparing a photosensitive resin composition suitable for dyes by introducing a dye that does not form particles instead of a pigment. However, in the case of dyes, the degradation of luminance due to the deterioration of durability, such as light and heat resistance compared to the pigment is concerned.

One embodiment is to provide a new compound having excellent brightness and contrast ratio.

Another embodiment is to provide a core-shell dye comprising the novel compound.

Another embodiment is to provide a photosensitive resin composition comprising the novel compound or core-shell dye.

Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.

One embodiment provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

R ¹ and R ² are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl group, provided that R ¹ and R ² Each independently include a functional group and a chiral carbon represented by the following Chemical Formula 1-1,

R ³ and R ⁴ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

[Formula 1-1]

In Chemical Formula 1-1,

R ⁶ is a substituted or unsubstituted C1 to C20 alkyl group.

R ¹ and R ² may be each independently represented by the following Chemical Formula 2-1 or the following Chemical Formula 2-2.

[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,

L ¹ is a single bond, a substituted or unsubstituted C1 to C10 alkylene group, or a substituted or unsubstituted C3 to C10 cycloalkylene group,

L ² is a substituted or unsubstituted C1 to C10 alkylene group or a substituted or unsubstituted C3 to C10 cycloalkylene group,

R ⁵ and R ⁶ are each independently a substituted or unsubstituted C1 to C20 alkyl group.

R ⁶ may be a C1 to C20 alkyl group substituted with a C1 to C10 alkyl group or a C6 to C20 aryl group.

R ⁶ may be represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

R ⁷ and R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group.

R ³ and R ⁴ may be each independently a C6 to C20 aryl group unsubstituted or substituted with a C1 to C10 alkyl group.

The compound represented by Chemical Formula 1 may be represented by any one of the compounds represented by the following Chemical Formulas 4 to 10.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

Another embodiment includes a core comprising a compound represented by Formula 1; And it provides a core-shell dye comprising a shell surrounding the core.

The cell may be represented by the following Formula 11 or Formula 12.

[Formula 11]

[Formula 12]

In Chemical Formulas 11 and 12,

L ^a to L ^d are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

L ^a to L ^d may be each independently a substituted or unsubstituted C1 to C10 alkylene group.

The cell may be represented by the following Formula 11-1 or Formula 12-1.

[Formula 11-1]

[Formula 12-1]

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

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

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

The core-shell dye may be represented by any one selected from the group consisting of compounds represented by the following Chemical Formulas 13 to 26.

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

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.

Another embodiment provides a photosensitive resin composition comprising the compound or the 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 may include 0.5 wt% to 10 wt% of the compound or core-shell dye, based on the total amount of the photosensitive resin composition; 0.1 wt% to 30 wt% of the binder resin; 0.1 wt% to 30 wt% of the photopolymerizable monomer; 0.1 wt% to 5 wt% of the photopolymerization initiator; And the balance of the solvent.

The photosensitive resin composition may further include a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof, including malonic acid, 3-amino-1,2-propanediol, a vinyl group, or a (meth) acryloxy group. It may include.

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

Other specific details of embodiments of the present invention are included in the following detailed description.

By using the compound or the core-shell dye according to one embodiment, it is possible to implement a color filter having excellent brightness and contrast ratio.

1 is a view showing the cage width (cage width) of the shell represented by the formula (11-1).

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

Unless stated otherwise in the specification, at least one hydrogen atom in the compound is a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, already Nogi group, azido group, amidino group, hydrazino group, hydrazono group, carbonyl group, carbamyl group, thiol group, ester group, ether group, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof , C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C6 to C30 aryl group, C3 to C20 cycloalkyl group, C3 to C20 cycloalkenyl group, C3 to C20 cycloalkynyl group, C2 to C20 heterocycloalkyl group A C2 to C20 heterocycloalkenyl group, a C2 to C20 heterocycloalkynyl group, or a combination thereof.

Unless otherwise specified in the specification, "heterocycloalkyl group", "heterocycloalkenyl group", "heterocycloalkynyl group" and "heterocycloalkylene group" are each cycloalkyl, cycloalkenyl, cycloalkynyl and cycloalkyl. It means that at least one hetero atom of N, O, S or P is present in the ring compound of the len.

Unless stated otherwise in the present specification, "(meth) acrylate" means that both "acrylate" and "methacrylate" are possible.

Unless otherwise defined herein, “combination” means mixed or copolymerized. In addition, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means block copolymer to random copolymerization.

Unless otherwise defined in the chemical formulas herein, 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.

Also, unless otherwise defined herein, "*" means chiral carbon. The chiral carbon means a central carbon in which all four functional groups around the carbon are different, and the compound having the chiral carbon does not overlap each other in the actual image and the mirror image.

In addition, unless otherwise defined herein, the compound comprising the chiral carbon may be an R-type optical isomer, an S-configuration optical isomer, a racemic mixture thereof, and It includes any one selected from the group consisting of a combination of these.

Also, unless otherwise defined herein, "**" refers to a moiety linked to the same or different atoms or formulas.

Compound according to one embodiment is represented by the formula (1).

[Formula 1]

In Chemical Formula 1,

R ¹ and R ² are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl group, provided that R ¹ and R ² Each independently include a functional group and a chiral carbon represented by the following Chemical Formula 1-1,

R ³ and R ⁴ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

[Formula 1-1]

In Chemical Formula 1-1,

R ⁶ is a substituted or unsubstituted C1 to C20 alkyl group.

The compound represented by Chemical Formula 1 may be used as a green dye as a compound having excellent green spectral characteristics and a high molar extinction coefficient. However, after the color resist is manufactured with an inferior durability compared to the pigment, a decrease in luminance may occur during the baking process. The compound according to one embodiment may improve durability by any one of the substituents connected to the nitrogen atom necessarily include the functional group and chiral carbon represented by Formula 1-1, and thus have a high brightness and high contrast ratio color. You can implement filters.

In Formula 1, R ¹ and R ² may be each independently represented by the following Formula 2-1 or the following Formula 2-2.

[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,

L ¹ is a single bond, a substituted or unsubstituted C1 to C10 alkylene group, or a substituted or unsubstituted C3 to C10 cycloalkylene group,

L ² is a substituted or unsubstituted C1 to C10 alkylene group or a substituted or unsubstituted C3 to C10 cycloalkylene group,

R ⁵ and R ⁶ are each independently a substituted or unsubstituted C1 to C20 alkyl group.

In Formulas 2-1 and 2-2, R ⁶ may be a C1 to C20 alkyl group substituted with a C1 to C10 alkyl group or a C6 to C20 aryl group.

In Formulas 2-1 and 2-2, L ¹ may be a single bond, a substituted or unsubstituted C1 to C10 alkylene group, and L ² may be an unsubstituted C3 to C10 cycloalkylene group.

For example, R ⁶ may be represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

R ⁷ and R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group.

When R ⁶ is represented by Chemical Formula 3, the compound according to the embodiment includes an alkoxy group including a branched alkyl group as a substituent, and thus includes a branched non-branched alkyl group (unsubstituted alkyl group). The luminance and contrast ratio can be further improved than in the case of having an alkoxy group as a substituent.

R ³ and R ⁴ may be each independently a C6 to C20 aryl group unsubstituted or substituted with a C1 to C10 alkyl group.

For example, R ³ and R ⁴ may be each independently represented by the following Formula A, but are not necessarily limited thereto.

[Formula A]

In Formula A,

R ⁹ is a substituted or unsubstituted C1 to C10 alkyl group,

n is an integer of 1-5.

For example, in Formula A, n may be an integer of 1 or 2.

For example, in Formula A, R ⁹ may be present at ortho and / or para positions.

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

The compound represented by Chemical Formula 1 may have excellent heat resistance. That is, the pyrolysis temperature when measured by a thermogravimetric analyzer (TGA) may be 200 ° C or more, for example, 200 ° C to 300 ° C.

The compound represented by Chemical Formula 1 has three resonance structures, as shown in the following scheme, but for the sake of convenience, the compound represented by Chemical Formula 1 may be represented by only one resonance structure. That is, the compound represented by Chemical Formula 1 may be represented by any one of the three resonance structures.

[scheme]

The compound represented by Chemical Formula 1 may be represented by any one selected from the group consisting of compounds represented by the following Chemical Formulas 4 to 10.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

Core-shell dye according to another embodiment may have a structure consisting of a core and a shell surrounding the core. The core includes a compound represented by Chemical Formula 1. Specifically, the shell may be a macrocyclic compound, the shell may form a coating layer surrounding the compound represented by the formula (1).

In one embodiment, the shell corresponding to the macrocyclic compound has a structure surrounding the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1 exists inside the macrocyclic ring, It is possible to improve the durability of the core-shell dye, thereby realizing a high brightness and high contrast color filter.

The length of the compound included in the core or represented by Formula 1 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 range, it is possible to easily form a core-shell dye having a structure of a core and a shell surrounding the compound. In other words, as the compound represented by Chemical Formula 1 has a length within the range, the macrocyclic compound shell may be obtained in a structure surrounding the compound represented by Chemical Formula 1. In the case of using other compounds that do not correspond to the length of the above range, it is difficult to expect the improvement of durability due to the difficulty of forming a structure surrounding the compound serving as the core.

The compound represented by Formula 1 included in the core or constituting the core may have a maximum absorption peak at a wavelength of 530 nm to 680 nm. By using the core-shell dye using the compound represented by the said Formula (1) which has the said spectral characteristic as a core as a green dye, for example, the photosensitive resin composition for color filters which has high brightness and high contrast ratio can be obtained.

The shell surrounding the core including the compound represented by Formula 1 may be represented by the following Formula 11 or Formula 12.

[Formula 11]

[Formula 12]

In Chemical Formulas 11 and 12,

L ^a to L ^d are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.

In Formula 11 or Formula 12, L ^a to L ^d may be each independently a substituted or unsubstituted C1 to C10 alkylene group. In this case, it is excellent in solubility and it is easy to form the structure which a shell encloses the core containing the compound represented by the said Formula (1).

For example, a core-shell dye according to one embodiment is a non-covalent bond, that is, a hydrogen bond between an oxygen atom of a compound represented by Formula 1 and a nitrogen atom of a shell represented by Formula 11 or Formula 12 It may include.

The shell may be represented by, for example, the formula 11-1 or 12-1.

[Formula 11-1]

[Formula 12-1]

The cage width of the shell may be 6.5 kPa to 7.5 kPa, and the volume of the shell may be 10 kPa to 16 kPa. As used herein, the cage width refers to a shell internal distance, such as a distance between two different phenylene groups in which a methylene group is connected to both sides in a shell represented by Formula 11-1 or Formula 12-1. (See Figure 1). When the shell has a cage width within the above range, it is possible to obtain a core-shell dye having a structure surrounding the core comprising the compound represented by Formula 1, thereby adding the core-shell dye to the photosensitive resin composition In this case, it is possible to implement a color filter having excellent durability and high brightness.

The core-shell dye may include a core including the compound represented by Chemical 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 including the compound represented by Formula 1 may be well formed.

For example, the core-shell dye may be represented by any one selected from the group consisting of compounds represented by the following Chemical Formulas 13 to 26, but is not necessarily limited thereto.

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

The core-shell dye may be used alone as a green dye, or may be used in combination with a color dye.

Examples of the dye include triaryl methane dyes, anthraquinone dyes, benzylidene dyes, cyanine dyes, phthalocyanine dyes, azapopyrine dyes, indigo dyes, and xanthene dyes.

The core-shell dyes may also be used in admixture with pigments.

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

Examples of the red pigment include C.I. Red pigment 254, C.I. Red pigment 255, C.I. Red pigment 264, C.I. Red pigment 270, C.I. Red pigment 272, C.I. Red pigment 177, C.I. Red pigment 89; and the like. Examples of the green pigment include C.I. Green pigment 36, C.I. Green pigment 7, C.I. Green pigment 58; and the like. Examples of the blue pigment include C.I. Blue pigment 15: 6, C.I. Blue pigment 15, C.I. Blue pigment 15: 1, C.I. Blue pigment 15: 2, C.I. Blue pigment 15: 3, C.I. Blue pigment 15: 4, C.I. Blue pigment 15: 5, C.I. Copper phthalocyanine pigments such as blue pigment 16 and the like. Examples of the yellow pigment include C.I. Isoindolin pigments such as yellow pigment 139 and the like, C.I. Quinophthalone pigments such as yellow pigment 138 and the like, C.I. Nickel complex pigments such as yellow pigment 150 and the like. Examples of the black pigment include aniline black, perylene black, titanium black, carbon black and the like. The pigments may be used alone or by mixing two or more thereof, but are not limited to these examples.

The pigment may be included in the photosensitive resin composition for color filters in the form of a dispersion. Such pigment dispersion may be composed of the pigment and a solvent, a dispersant, a dispersion resin and the like.

The solvent may be ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like, and among these, propylene glycol methyl ether acetate may be used. Can be.

The dispersant helps to uniformly disperse the pigment in the dispersion, and can be used for both nonionic, anionic or cationic dispersants. Specifically, polyalkylene glycol or ester thereof, polyoxy alkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salt, alkyl amide alkylene oxide addition Water, alkyl amine, etc. can be used, These can be used individually or in mixture of 2 or more types.

The dispersion resin may use an acrylic resin including a carboxyl group, which may not only improve the stability of the pigment dispersion but also improve the pattern of the pixel.

When the core-shell dye and the pigment are used in combination, the core-shell dye and the pigment may be used in a weight ratio of 1: 9 to 9: 1, specifically, in a weight ratio of 3: 7 to 7: 3. have. When mixed in the weight ratio range, it may have a high luminance and contrast ratio while maintaining color characteristics.

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

The photosensitive resin composition includes (A) a colorant (compound represented by Formula 1 or the core-shell dye), (B) binder resin, (C) photopolymerizable monomer, (D) photopolymerization initiator, and (E) solvent. can do.

Each component is demonstrated concretely below.

(A) colorant

The colorant may include the compound represented by Formula 1 and / or the core-shell dye, and the compound represented by Formula 1 and / or the core-shell dye has been described above.

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

The compound represented by Formula 1 and / or the core-shell dye may be included in an amount of 0.5 wt% to 10 wt%, such as 0.5 wt% to 5 wt%, based on the total amount of the photosensitive resin composition. When the core-shell dye is used in the above range, it is possible to express a high brightness and contrast ratio in the desired color coordinates.

(B) binder resin

The binder resin is a first ethylenically unsaturated monomer 　 And a copolymer of a second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin including one or more acrylic repeating units.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxyl groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, and combinations thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, such as 10 wt% to 40 wt%, based on the total amount of the alkali-soluble resin.

The second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, vinylbenzylmethyl ether, etc .; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds, such as vinyl acetate and a vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; Vinyl cyanide compounds such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These etc. can be mentioned, These can be used individually or in mixture of 2 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 And methacrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc. are mentioned, It is not limited to these, These can also be used individually or in combination of 2 or more types.

The weight average molecular weight of the binder resin may be 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. When the weight average molecular weight of binder resin is the said range, it is excellent in adhesiveness with a board | substrate, physical and chemical properties are good, and viscosity is appropriate.

The acid value of the binder resin may be 15 mgKOH / g ~ 60 mgKOH / g, such as 20 mgKOH / g ~ 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 based on the total amount of the photosensitive resin composition. 0.1 wt% to 30 wt%, such as 5 wt% to 20 wt%. In the case where the binder resin is included in the above range, the developability and the crosslinkability of the color filter may be improved to obtain excellent surface smoothness.

(C) Photopolymerizable  Monomer

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

Since the photopolymerizable monomer has the ethylenically unsaturated double bond, the photopolymerizable monomer may form a pattern having excellent heat resistance, light resistance, and chemical resistance by causing sufficient polymerization during exposure in the pattern forming process.

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 There may be mentioned furnace methyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolak epoxy (meth) acrylate, and the like.

Examples of commercially available products of the photopolymerizable monomer are as follows. Examples of the monofunctional ester of (meth) acrylic acid include Aronix M-101 ^® , M-111 ^® , M-114 ^®, and the like manufactured by Toagosei Kagaku Kogyo Co., Ltd .; Nihon Kayaku Co., Ltd. KAYARAD TC-110S ^® , TC-120S ^®, etc .; The V-158 ^® and V-2311 ^{® of} Osaka Yuki Chemical Co., Ltd. are mentioned. Examples of the difunctional ester of the (meth) acrylic acid include, but are not limited to, Aronix M-210 ^® , M-240 ^® , M-6200 ^®, etc. manufactured by Toagosei Chemical Industries, Ltd .; Nihon Kayaku Co., Ltd. KAYARAD HDDA ^® , HX-220 ^® , R-604 ^®, etc .; And V-260 ^® , V-312 ^® and V-335 HP ^{® from} Osaka Yuki Kagaku Kogyo Co., Ltd. Examples of the trifunctional ester of (meth) acrylic acid include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-450 ^{® from} Toagosei Kagaku Kogyo Co., Ltd. -7100 ^® , M-8030 ^® , M-8060 ^®, etc .; Nihon Kayaku Co., Ltd., KAYARAD TMPTA ^® , DPCA-20 ^® , East-30 ^® , East-60 ^® , East-120 ^®, etc .; Osaka yukki Kayaku high (primary)社of V-295 ^®, copper ^® -300, -360 ^® copper, copper -GPT ^®, copper -3PA ^®, and the like copper -400 ^®. The above products can be used alone or in combination of two or more.

The photopolymerizable monomer may be used by treating with an acid anhydride in order to impart better developability.

The photopolymerizable monomer may be included in an amount of 0.1 wt% to 30 wt%, such as 5 wt% to 20 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included in the above range, it is excellent in pattern characteristics and developability when manufacturing a color filter.

(D) Photopolymerization Initiator

The photopolymerization initiator may be an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, an oxime compound, or the like.

Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt-butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethyl amino) 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-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal and the like.

Examples of the triazine-based 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- (naphtho1-yl) -4,6 -Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2-4-tri chloromethyl (Piperonyl) -6-triazine, 2-4-trichloromethyl (4'-methoxystyryl) -6-triazine, etc. are mentioned.

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

In addition to the compound, the photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, or the like.

The photopolymerization initiator may be included in an amount of 0.1 wt% to 5 wt%, such as 1 wt% to 3 wt%, based on 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 manufacturing a color filter, thereby providing excellent sensitivity and improving transmittance.

(E) solvent

The solvent is not particularly limited, and specific examples thereof include 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, and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butylkenone, methyl-n-amyl ketone and 2-heptanone ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Hydroxyacetic acid alkyl esters such as methyl hydroxyacetate, ethyl hydroxyacetate and butyl hydroxyacetate; Acetate alkoxyalkyl esters, such as methoxymethyl acetate, methoxyethyl acetate, methoxybutyl acetate, ethoxymethyl acetate, ethoxyethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, and propyl 2-hydroxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-hydroxy-2-methylpropionic acid alkyl esters such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate and methyl 2-hydroxy-3-methylbutanoate; Or ketone acid esters such as ethyl pyruvate, and N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid Ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, and the like, and these may be used alone or in combination of two or more thereof.

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; Esters such as 2-hydroxyethyl propionate; Diethylene glycols such as diethylene glycol monomethyl ether; Propylene glycol alkylether acetates such as propylene glycol monomethylether acetate and propylene glycol propylether acetate can be used.

The solvent may be included in the remainder relative to the total amount of the photosensitive resin composition, and specifically, may be included in an amount of 20 wt% to 90 wt%. When a solvent is contained in the said range, the applicability | paintability of the photosensitive resin composition is excellent and it can maintain the flatness outstanding in the film | membrane of thickness 3micrometer or more.

(F) other additives

The photosensitive resin composition may be used to prevent stains or spots upon application, to improve leveling performance, and to prevent generation of residues due to undeveloped malonic acid; 3-amino-1,2-propanediol; Silane coupling agent containing a vinyl group or a (meth) acryloxy group; Leveling agents; Fluorine-based surfactants; Additives, such as a radical polymerization initiator, may be further included.

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

As an example of the said epoxy compound, a phenol novolak epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol-A epoxy compound, an alicyclic epoxy compound, or a combination thereof is mentioned.

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

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

Using a suitable method such as spin coating or slit coating, the photosensitive resin composition for color filters described above is applied onto a glass substrate on which nothing is applied or on a glass substrate on which a protective film of SiN _x is applied at a thickness of 500 kPa to 1500 kPa. Each is applied in a thickness of 3.1 μm to 3.4 μm. After application, light is irradiated to form a pattern required for the color filter. After irradiating the light, the coating layer is treated with an alkaline developer, so that the unilluminated portion of the coating layer is dissolved and a pattern necessary for the color filter is formed. By repeating this process in accordance with the required number of R, G, and B colors, a color filter having a desired pattern can be obtained.

Further, in the above process, crack resistance, solvent resistance, and the like can be further improved by heating the image pattern obtained by development again or curing by active ray irradiation or the like.

Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only preferred embodiments of the present invention, and the present invention is not limited to the following examples.

( Single molecule  Compound preparation)

( Synthesis Example  1: synthesis of intermediate A)

Aniline (10 mol), 4-bromotoluene (10 mol), Pd ₂ (dba) ₃ (0.1 mol), Xphos (0.1 mol) was added to toluene and heated to 100 ℃ and stirred for 24 hours. Ethyl acetate was added to the solution, washed twice with water, and the organic layer was extracted. The extracted organic layer was distilled under reduced pressure and purified by column chromatography to obtain intermediate A.

( Synthesis Example  2: synthesis of intermediate B-1)

2,4-dimethyldiphenylamine (10 mol), 1,2-epoxyhexane (12 mol) and sodium hydride (12 mol) were added to N, N-dimethylformamide and heated to 90 ° C. and stirred for 24 hours. . Ethyl acetate was added to the solution, washed twice with water, and the organic layer was extracted. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain intermediate B-1.

( Synthesis Example  3: synthesis of intermediate B-2)

Intermediate B-2 was obtained by the same method as Synthesis Example 2, except that 1,2-butyleneoxide was used instead of 1,2-epoxyhexane.

( Synthesis Example  4: synthesis of intermediate B-3)

Intermediate B-3 was obtained by the same method as Synthesis Example 2, except that Intermediate A was used instead of 2,4-dimethyldiphenylamine.

( Synthesis Example  5: synthesis of intermediate B-4)

Intermediate B-4 was obtained by the same method as Synthesis Example 2, except that 1,2-epoxycyclohexane was used instead of 1,2-epoxyhexane.

( Synthesis Example  6: synthesis of intermediate C-1)

Intermediate B-1 (10 mmol), iodomethane (15 mmol) and sodium hydride (15 mmol) were added to N, N-dimethylformamide and stirred at room temperature for 24 hours. Ethyl acetate was added to the solution, washed twice with water, and the organic layer was extracted. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain intermediate C-1.

( Synthesis Example  7: synthesis of intermediate C-2)

Intermediate C-2 was obtained by the same method as Synthesis Example 6, except that 2-iodopropane was used instead of iodomethane.

( Synthesis Example  8: synthesis of intermediate C-3)

Intermediate C-3 was obtained by the same method as Synthesis Example 6, except that Intermediate B-2 was used instead of Intermediate B-1.

( Synthesis Example  9: synthesis of intermediate C-4)

Intermediate C-4 was obtained by the same method as Synthesis Example 8, except that iodomethane was used instead of iodomethane.

( Synthesis Example  10: synthesis of intermediate C-5)

Intermediate C-5 was obtained by the same method as Synthesis Example 8, except that 2-iodopropane was used instead of iodomethane.

( Synthesis Example  11: synthesis of intermediate C-6)

Intermediate C-6 was obtained by the same method as Synthesis Example 6, except that Intermediate B-3 was used instead of Intermediate B-1.

( Synthesis Example  12: synthesis of intermediate C-7)

Intermediate C-7 was obtained by the same method as Synthesis Example 6, except that Intermediate B-4 was used instead of Intermediate B-1.

( Synthesis Example  13: synthesis of a compound represented by formula (4)

Formed by refluxing Intermediate C-1 (60 mmol), 3,4-dihydroxy-3-cyclobutyne-1,2-dione (30 mmol) in toluene (200 mL) and butanol (200 mL) The water is removed with a Dean-stark distillation unit. After stirring for 12 hours, the green reactant was distilled under reduced pressure and purified by column chromatography to obtain a compound represented by Chemical Formula 4.

( Synthesis Example  14: synthesis of the compound represented by formula 5)

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate C-2 was used instead of Intermediate C-1 to obtain a compound represented by Formula 5.

( Synthesis Example  15: synthesis of the compound represented by formula (6)

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate C-3 was used instead of Intermediate C-1 to obtain a compound represented by Chemical Formula 6.

( Synthesis Example  16: synthesis of a compound represented by formula (7))

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate C-4 was used instead of Intermediate C-1 to obtain a compound represented by Formula 7.

( Synthesis Example  17: synthesis of the compound represented by formula (8)

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate C-5 was used instead of Intermediate C-1 to obtain a compound represented by Formula 8.

( Synthesis Example  18: Synthesis of Compound Represented by Formula 9)

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate C-6 was used instead of Intermediate C-1, to obtain a compound represented by Formula 9.

( Synthesis Example  19: Synthesis of Compound Represented by Formula 10)

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate C-7 was used instead of Intermediate C-1, to obtain a compound represented by Formula 10.

( Synthesis Example  20: synthesis of the core-shell dye represented by Formula 13)

After dissolving the compound represented by Chemical Formula 4 (5 mmol) in 600 mL chloroform solvent, Isophthaloyl chloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 mL chloroform, and simultaneously added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by Formula 13.

Maldi-tof MS: 1232.64m / z

( Synthesis Example  21: Synthesis of core-shell dye represented by Formula 14)

After dissolving the compound represented by the formula (5 mmol) in 600mL chloroform solvent, triethylamine (50mmol) was added thereto. 2,6-pyridinedicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) are dissolved in 60 mL chloroform and added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a compound represented by Formula 14.

Maldi-tof MS: 1234.63m / z

( Synthesis Example  22: synthesis of the core-shell dye represented by Formula 15)

A compound represented by Chemical Formula 15 was obtained by synthesizing in the same manner as in Synthesis Example 20, except that the compound represented by Chemical Formula 5 was used instead of the compound represented by Chemical Formula 4.

Maldi-tof MS: 1288.70m / z

( Synthesis Example  23: synthesis of the core-shell dye represented by Formula 16)

Except for using the compound represented by the formula (5) instead of the compound represented by the formula (4) was synthesized in the same manner as in Synthesis Example 21 to obtain a compound represented by the formula (16).

Maldi-tof MS: 1290.69m / z

( Synthesis Example  24: synthesis of the core-shell dye represented by Formula 17)

Except for using the compound represented by the formula (6) instead of the compound represented by the formula (4) was synthesized in the same manner as in Synthesis Example 20 to obtain a compound represented by the formula (17).

Maldi-tof MS: 1176.57m / z

( Synthesis Example  25: synthesis of the core-shell dye represented by Formula 18)

Except for using the compound represented by the formula (6) instead of the compound represented by the formula (4) was synthesized in the same manner as in Synthesis Example 21 to obtain a compound represented by the formula (18).

Maldi-tof MS: 1178.56 m / z

( Synthesis Example  26: synthesis of the core-shell dye represented by Formula 19)

Synthesis was carried out in the same manner as in Synthesis Example 20, except that the compound represented by the formula (7) was used instead of the compound represented by the formula (4) to obtain a compound represented by the formula (19).

Maldi-tof MS: 1204.60m / z

( Synthesis Example  27: synthesis of the core-shell dye represented by Formula 20)

Except for using the compound represented by the formula (7) instead of the compound represented by the formula (4) was synthesized in the same manner as in Synthesis Example 21 to obtain a compound represented by the formula (20).

Maldi-tof MS: 1206.59 m / z

( Synthesis Example  28: synthesis of the core-shell dye represented by Formula 21)

A compound represented by Chemical Formula 21 was obtained by synthesizing in the same manner as Synthesis Example 20, except that the compound represented by Chemical Formula 8 was used instead of the compound represented by Chemical Formula 4.

Maldi-tof MS: 1232.64m / z

( Synthesis Example  29: synthesis of the core-shell dye represented by Formula 22)

A compound represented by Chemical Formula 22 was obtained by synthesizing in the same manner as in Synthesis Example 21, except that the compound represented by Chemical Formula 8 was used instead of the compound represented by Chemical Formula 4.

Maldi-tof MS: 1234.63m / z

( Synthesis Example  30: synthesis of the core-shell dye represented by Formula 23)

A compound represented by Chemical Formula 23 was obtained by synthesizing in the same manner as in Synthesis Example 20, except that the compound represented by Chemical Formula 9 was used instead of the compound represented by Chemical Formula 4.

Maldi-tof MS: 1204.60m / z

( Synthesis Example  31: synthesis of the core-shell dye represented by Formula 24)

A compound represented by Chemical Formula 24 was obtained by synthesizing in the same manner as in Synthesis Example 21, except that the compound represented by Chemical formula 9 was used instead of the compound represented by Chemical Formula 4.

Maldi-tof MS: 1206.59 m / z

( Synthesis Example  32: synthesis of the core-shell dye represented by Formula 25)

Except for using the compound represented by the formula (10) instead of the compound represented by the formula (4) was synthesized in the same manner as in Synthesis Example 20 to obtain a compound represented by the formula (25).

Maldi-tof MS: 1228.60m / z

( Synthesis Example  33: Synthesis of core-shell dye represented by Formula 26)

A compound represented by Chemical Formula 26 was obtained by synthesizing in the same manner as in Synthesis Example 21, except that the compound represented by Chemical Formula 10 was used instead of the compound represented by Chemical Formula 4.

Maldi-tof MS: 1230.59m / z

( Comparative Synthesis Example  1: synthesis of a compound represented by formula (X)

[Formula X]

Synthesis was carried out in the same manner as in Synthesis Example 13, except that Intermediate B-3 was used instead of Intermediate C-1 to obtain a compound represented by Formula (X).

Maldi-tof MS: 672.39m / z

( Comparative Synthesis Example  2: synthesis of a compound represented by formula Y)

[Formula Y]

Into a 100 mL three-neck flask, 398 mg of squaraine acid and 2.23 g of 2- (3- (methyl (phenyl) amino) propylamino) ethyl acrylate were added, followed by 40 mL of n-butanol and 20 mL of toluene. Heated to reflux. The Dean-Stark trap set was used to remove the water generated during the reaction and to promote the reaction. After the completion of the reaction, the mixture was cooled, extracted with methylene chloride, and then subjected to column chromatography to synthesize the compound represented by Chemical Formula Y in 60% yield.

Maldi-tof MS: 514.26 m / z

(Comparative Synthesis Example 3: core-shell composite of dye)

Into a 100 mL 3-neck flask, 398 mg of squariaic acid and 2.23 g of 2- (3- (dibutylamino) phenoxy) ethyl acrylate were added, followed by 40 mL of n-butanol and 20 mL of toluene. It was. The Dean-Stark trap set was used to remove the water generated during the reaction and to promote the reaction. After the reaction was completed, the mixture was cooled, extracted with methylene chloride, and then subjected to column chromatography to obtain a compound represented by Chemical Formula Z-1 in 60% yield. Thereafter, 0.72 g (1 mmol) of the compound represented by Chemical Formula Z-1 and triacetyl beta-cyclodextrin represented by Chemical Formula Z-2 (triacetyl β-cyclodextrin, TCI Corporation, CAS # 23739-88) -0) 2.02 g (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 the core-shell dye in a solid state. The core-shell dye was obtained in a structure in which the compound represented by Chemical Formula Z-1 is surrounded by the compound represented by Chemical Formula Z-2.

[Formula Z-1]

[Formula Z-2]

(Photosensitive resin composition production)

The specification of the component used for manufacture of the photosensitive resin composition is as follows.

(A) dye

(A-1) Monomolecular Dye Prepared in Synthesis Example 13

(A-2) Monomolecular Dye Prepared in Synthesis Example 14 (Formula 5)

(A-3) Single molecule dye prepared in Synthesis Example 15 (expressed in Chemical Formula 6)

(A-4) Monomolecular Dye Prepared in Synthesis Example 16 (Formula 7)

(A-5) Monomolecular Dye Prepared in Synthesis Example 17

(A-6) Monomolecular Dye Prepared in Synthesis Example 18

(A-7) Monomolecular Dye Prepared in Synthesis Example 19

(A-8) Core-shell Dye Prepared in Synthesis Example 20 (Formula 13)

(A-9) Core-shell Dye Prepared in Synthesis Example 21 (Formula 14)

(A-10) Core-shell Dye Prepared in Synthesis Example 22 (Formula 15)

(A-11) Core-shell Dye Prepared in Synthesis Example 23 (Formula 16)

(A-12) Core-Shell Dye Prepared in Synthesis Example 24

(A-13) Core-shell Dye Prepared in Synthesis Example 25 (Formula 18)

(A-14) Core-Shell Dye Prepared in Synthesis Example 26 (Formula 19)

(A-15) Core-shell Dye Prepared in Synthesis Example 27 (Formula 20)

(A-16) Core-Shell Dye Prepared in Synthesis Example 28 (Formula 21)

(A-17) Core-shell dye prepared in Synthesis Example 29 represented by Formula 22

(A-18) Core-shell dye prepared in Synthesis Example 30 (expressed in Formula 23)

(A-19) Core-shell dye prepared in Synthesis Example 31 (expressed in Chemical Formula 24)

(A-20) Core-shell dye prepared in Synthesis Example 32 (expressed by Chemical Formula 25)

(A-21) Core-shell dye prepared in Synthesis Example 33 (expressed as Formula 26)

(A-22) Monomolecular Dye Prepared in Comparative Synthesis Example 1 (Formula X)

(A-23) Monomolecular Dye Prepared in Comparative Synthesis Example 2 (Formula Y)

(A-24) Core-shell Dye Prepared in Comparative Synthesis Example 3

(A ') Pigment Dispersion

(A'-1) C.I. Green Pigment 7

(A'-2) C.I. Green Pigment58

(B) binder resin

Methacrylic acid / benzyl methacrylate copolymer having a weight average molecular weight of 22,000 g / mol (mixed weight ratio 15wt% / 85wt%)

(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

Example  1 to Example  21 and Comparative example  One Comparative Example  5

Each component was mixed with the composition of Tables 1 to 3 to prepare a photosensitive resin composition. Specifically, after dissolving the photopolymerization initiator in a solvent, the mixture is stirred at room temperature for 2 hours, then added with a dye (or pigment dispersion) and stirred for 30 minutes, and then the binder resin and the photopolymerizable monomer are added thereto at room temperature for 2 hours. Stirred. The solution was filtered three times to remove impurities to prepare a photosensitive resin composition.

(Unit: weight%) Example One 2 3 4 5 6 7 8 9 (A) dye A-1 2 - - - - - - - - A-2 - 2 - - - - - - - A-3 - - 2 - - - - - - A-4 - - - 2 - - - - - A-5 - - - - 2 - - - - A-6 - - - - - 2 - - - A-7 - - - - - - 2 - - A-8 - - - - - - - 2 - A-9 - - - - - - - - 2 (A ') pigment dispersion A'-1 - - - - - - - - - A'-2 - - - - - - - - - (B) binder resin 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 (C) photopolymerizable monomer 8 8 8 8 8 8 8 8 8 (D) photoinitiator D-1 One One One One One One One One One D-2 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 (E) solvent E-1 40 40 40 40 40 40 40 40 40 E-2 45 45 45 45 45 45 45 45 45 Total 100 100 100 100 100 100 100 100 100

(Unit: weight%) Example 10 11 12 13 14 15 16 17 18 (A) dye A-10 2 - - - - - - - - A-11 - 2 - - - - - - - A-12 - - 2 - - - - - - A-13 - - - 2 - - - - - A-14 - - - - 2 - - - - A-15 - - - - - 2 - - - A-16 - - - - - - 2 - - A-17 - - - - - - - 2 - A-18 - - - - - - - - 2 (A ') pigment dispersion A'-1 - - - - - - - - - A'-2 - - - - - - - - - (B) binder resin 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 (C) photopolymerizable monomer 8 8 8 8 8 8 8 8 8 (D) photoinitiator D-1 One One One One One One One One One D-2 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 (E) solvent E-1 40 40 40 40 40 40 40 40 40 E-2 45 45 45 45 45 45 45 45 45 Total 100 100 100 100 100 100 100 100 100

(Unit: weight%) Example Comparative example 19 20 21 One 2 3 4 5 (A) dye A-19 2 - - - - - - - A-20 - 2 - - - - - - A-21 - - 2 - - - - - A-22 - - - 2 - - - - A-23 - - - - 2 - - - A-24 - - - - - 2 - - (A ') pigment dispersion A'-1 - - - - - - 2 - A'-2 - - - - - - - 2 (B) binder resin 3.5 3.5 3.5 3.5 3.5 3.5 3.5 3.5 (C) photopolymerizable monomer 8 8 8 8 8 8 8 8 (D) photoinitiator D-1 One One One One One One One One D-2 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 (E) solvent E-1 40 40 40 40 40 40 40 40 E-2 45 45 45 45 45 45 45 45 Total 100 100 100 100 100 100 100 100

(evaluation)

Evaluation 1: Durability Rating

The photosensitive resin composition prepared in Examples 1 to 21 and Comparative Examples 1 to 5 was coated on a glass substrate having a thickness of 1 mm degreased and washed, and then, on a hot plate at 90 ° C., Drying for minutes gave a coating. Subsequently, the coating film was exposed to light using a high pressure mercury lamp having a dominant wavelength of 365 nm, dried in an oven at 200 ° C. for 20 minutes, and the change in color coordinates was measured using a spectrophotometer (MCPD3000, Otsuka electronic). The durability was confirmed, and the results are shown in Table 4 below.

Durability Evaluation Criteria

Good: color coordinate change is 0.005 or less

Poor: Change in color coordinates exceeds 0.005

durability Example 1 Bad Example 2 Bad Example 3 Bad Example 4 Bad Example 5 Bad Example 6 Bad Example 7 Bad Example 8 Good Example 9 Good Example 10 Good Example 11 Good Example 12 Good Example 13 Good Example 14 Good Example 15 Good Example 16 Good Example 17 Good Example 18 Good Example 19 Good Example 20 Good Example 21 Good Comparative Example 1 Bad Comparative Example 2 Bad Comparative Example 3 Bad Comparative Example 4 Good Comparative Example 5 Good

From Table 4, in the case of Examples 8 to 21 comprising a core-shell dye according to one embodiment, a composition comprising a single molecule dye according to the embodiment (Examples 1 to 7), A composition comprising a monomolecular dye different from the monomolecular dye according to one embodiment (Comparative Example 1, Comparative Example 2), a composition comprising a core-shell dye different from the core-shell dye according to one embodiment (Comparative Example 3 In comparison with the composition (Comparative Example 4, Comparative Example 5) containing a) and a pigment, it can be confirmed that the durability is increased.

Evaluation 2: Luminance and Contrast Rating

The photosensitive resin composition prepared in Examples 1 to 21 and Comparative Examples 1 to 5 was applied on a glass substrate having a thickness of 1 mm degreased and washed, and then, on a hot plate at 90 ° C., Drying for minutes gave a coating. Subsequently, the coating film was exposed to light using a high pressure mercury lamp having a dominant wavelength of 365 nm, and then dried in a hot air circulation drying furnace at 200 ° C. for 5 minutes. The pixel layer was measured for brightness and contrast ratio using a spectrophotometer (MCPD3000, Otsuka electronic Co., Ltd.), and the results are shown in Table 5 below.

Luminance Contrast Ratio Example 1 65.5 14500 Example 2 65.7 14800 Example 3 65.5 14600 Example 4 65.3 14400 Example 5 65.8 14900 Example 6 65.3 14300 Example 7 65.5 14500 Example 8 67.5 14700 Example 9 67.6 14600 Example 10 67.9 15100 Example 11 67.8 15000 Example 12 67.3 14600 Example 13 67.2 14700 Example 14 67.5 14400 Example 15 67.4 14800 Example 16 67.8 15200 Example 17 67.9 15100 Example 18 67.6 14500 Example 19 67.5 14600 Example 20 67.4 14400 Example 21 67.3 14700 Comparative Example 1 64.3 13200 Comparative Example 2 64.5 13400 Comparative Example 3 64.2 13100 Comparative Example 4 62.1 12200 Comparative Example 5 63.5 12500

From Table 5, in Examples 1 to 21 containing a single molecule dye or a core-shell dye according to an embodiment, Comparative Examples 1 to Comparative Example not containing the single molecule dye or core-shell dye Compared with the case 5, it can be confirmed that high brightness and high contrast ratio can be obtained. In addition, when the compound according to the embodiment includes an alkoxy group substituted with a branched alkyl group as a functional group, it can also be seen that the brightness and contrast ratio is more excellent than otherwise.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

Claims (21)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
R ¹ and R ² are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl group, provided that R ¹ and R ² Each independently include a functional group and a chiral carbon represented by the following Chemical Formula 1-1,
R ³ and R ⁴ are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
[Formula 1-1]

In Chemical Formula 1-1,
R ⁶ is a substituted or unsubstituted C1 to C20 alkyl group.
The method of claim 1,
R ¹ and R ² are each independently a compound represented by Formula 2-1 or Formula 2-2:
[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,
L ¹ is a single bond, a substituted or unsubstituted C1 to C10 alkylene group or a substituted or unsubstituted C3 to C10 cycloalkylene group,
L ² is a substituted or unsubstituted C1 to C10 alkylene group or a substituted or unsubstituted C3 to C10 cycloalkylene group,
R ⁵ and R ⁶ are each independently a substituted or unsubstituted C1 to C20 alkyl group.
The method of claim 2,
R ⁶ is a C1 to C20 alkyl group substituted with a C1 to C10 alkyl group or a C6 to C20 aryl group.
The method of claim 3,
R ⁶ is a compound represented by Formula 3 below:
[Formula 3]

In Chemical Formula 3,
R ⁷ and R ⁸ are each independently a substituted or unsubstituted C1 to C10 alkyl group.
The method of claim 1,
R ³ and R ⁴ are each independently a C6 to C20 aryl group unsubstituted or substituted with a C1 to C10 alkyl group.
The method of claim 1,
The compound represented by Chemical Formula 1 is a compound represented by any one of the compounds represented by the following Chemical Formulas 4 to 10.
[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

A core comprising the compound of claim 1; And
A shell surrounding the core
Core-shell dye comprising a.
The method of claim 7, wherein
The cell is a core-shell dye represented by the following formula (11) or formula (12).
[Formula 11]

[Formula 12]

(In Formula 11 and Formula 12,
L ^a to L ^d are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group)
The method of claim 8,
Wherein L ^a to L ^d are each independently a substituted or unsubstituted C1 to C10 alkylene group.
The method of claim 8,
The cell is a core-shell dye represented by the following formula 11-1 or 12-1.
[Formula 11-1]

[Formula 12-1]

The method of claim 7, wherein
Said cell having a cage width of 6.5 kPa to 7.5 kPa.
The method of claim 7, wherein
The core-shell dye having a length of 1 nm to 3 nm.
The method of claim 7, wherein
The core having a maximum absorption peak at a wavelength of 530 nm to 680 nm.
The method of claim 7, wherein
The core-shell dye is a core-shell dye represented by any one selected from the group consisting of compounds represented by the following Chemical Formulas 13 to 26.
[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

The method of claim 7, wherein
Wherein said core-shell dye comprises said core and said shell in a molar ratio of 1: 1.
The method of claim 7, wherein
The core-shell dye is a green dye.
The photosensitive resin composition containing the compound of any one of Claims 1-6, or the core-shell dye of any one of Claims 7-16.
The method of claim 15,
The photosensitive resin composition further comprises a binder resin, a photopolymerizable monomer, a photopolymerization initiator and a solvent.
delete The method of claim 18,
The photosensitive resin composition may further include a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof, including malonic acid, 3-amino-1,2-propanediol, a vinyl group, or a (meth) acryloxy group. Photosensitive resin composition containing.
A color filter manufactured using the photosensitive resin composition of claim 17.

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