TW201912648A - Novel compounds, photosensitive resin compositions including the same, and color filters - Google Patents

Abstract

Disclosed are a compound represented by Chemical Formula 1, and a photosensitive resin composition including the same, and a color filter manufactured using the photosensitive resin composition. In Chemical Formula 1, each substituent was the same as defined in the specification. The compound of present disclosure has excellent green spectral characteristics, a high molar extinction coefficient and excellent solubility in an organic solvent.

Description

Novel compound, photosensitive resin composition including the same, and color filter

The present disclosure relates to a novel compound and a photosensitive resin composition and a color filter including the same.

A color filter manufactured by using a pigment-type photosensitive resin composition has limitations in brightness and contrast ratio due to pigment particle size. In addition, a color imaging device for an image sensor requires a smaller dispersed particle diameter to form a fine pattern. In response to this demand, there have been continuous attempts to provide color filters with improved color characteristics (such as brightness and contrast ratio) by preparing photosensitive resin compositions that contain dyes that do not form particles instead of pigment.

Therefore, there is a need to study a compound that produces a compound suitable as a dye for a photosensitive resin composition.

An embodiment provides a novel compound.

Another embodiment provides a photosensitive resin composition including the compound.

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

An embodiment of the present invention provides a compound represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R ¹ to R ^{16 are} independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 To C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, at least two of the restrictions R ¹ to R ¹⁶ are represented by Chemical Formula 2, [Chemical Formula 2] Among them, in Chemical Formula 2, R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.

Chemical formula 2 can be represented by chemical formula 3: [Chemical formula 3] In Chemical Formula 3, R ¹⁷ produces a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁸ produces a substituted or unsubstituted C1 to C20 alkoxy group.

R ¹⁷ can produce tert-butyl group.

At least one of R ¹ to R ¹⁶ generates a substituted or unsubstituted C1 to C20 alkoxy group.

At least one of R ¹ to R ⁴ may be represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and R ¹³ to R ¹⁶ At least one may be represented by Chemical Formula 2.

At least one of R ¹ to R ⁴ may generate a substituted or unsubstituted C1 to C20 alkoxy group, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2 is represented, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2.

R ¹ to R ⁴ may generate a halogen atom, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2 means.

R ¹ to R ⁸ may generate a halogen atom, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2.

R ¹ to R ⁴ may generate a halogen atom, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, R ⁹ to R ¹² may generate a halogen atom, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2.

The compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 4 to Chemical Formula 11: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] .

The compound may be a green dye.

The green dye may have a maximum transmittance in a wavelength range of 445 nm to about 560 nm.

Another embodiment provides a photosensitive resin composition including the compound.

The compound may be contained in an amount of 1 to 10% by weight based on the total amount of the photosensitive resin composition.

The photosensitive resin composition may further include an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

The photosensitive resin composition may further include a pigment.

The pigment may include a yellow pigment, a green pigment, or a combination thereof.

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

Other embodiments of the invention are contained in the following detailed description.

The compound according to an embodiment has excellent green spectral characteristics, a high molar extinction coefficient, and excellent solubility in an organic solvent, and thus can be used as a green color for color filters. The dye during the photosensitive resin composition, and therefore, the color filter including the dye can have excellent brightness and excellent contrast ratio.

Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and the present invention is defined by the scope of the patent application.

In this specification, when a specific definition is not otherwise provided, "substituted" refers to replacing at least one hydrogen of a functional group by at least one substituent selected from the group consisting of: halogen (F, Br, Cl, or I), hydroxyl , Nitro, cyano, amine (NH ₂ , NH (R ²⁰⁰ ) or N (R ²⁰¹ ) (R ²⁰² ), where R ²⁰⁰ , R ²⁰¹ and R ^{202 are the} same or different, and are independent C1 to C10 alkyl ), Formamyl, hydrazine, fluorenyl, carboxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted Alicyclic organic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

In this specification, when a specific definition is not otherwise provided, "alkyl" means C1 to C20 alkyl, and specifically C1 to C15 alkyl, and "cycloalkyl" means C3 to C20 cycloalkyl, And specifically C3 to C18 cycloalkyl, "alkoxy" means C1 to C20 alkoxy, and specifically C1 to C18 alkoxy, and "aryl" means C6 to C20 aryl, And specifically C6 to C18 aryl, "alkenyl" refers to C2 to C20 alkenyl, and specifically C2 to C18 alkenyl, "alkylene" refers to C1 to C20 alkylene, and specifically It is C1 to C18 alkylene, and "arylene" refers to C6 to C20 alkylene, and specifically C6 to C16 alkylene.

In this specification, when a specific definition is not otherwise provided, "(meth) acrylate" refers to both "acrylate" and "methacrylate", and "(Meth) acrylic acid" means "acrylic acid" and "methacrylic acid".

In this specification, when a definition is not otherwise provided, "combination" means mixing or copolymerizing. In addition, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means block copolymer to random copolymer.

In this specification, when a definition is not otherwise provided, when a chemical bond is not drawn, hydrogen is bonded at a position presumably given.

In this specification, when a specific definition is not otherwise provided, "*" indicates a point connecting the same or different atom or chemical formula.

An embodiment provides a compound represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R ¹ to R ^{16 are} independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 To C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, at least two of the restrictions R ¹ to R ¹⁶ are represented by Chemical Formula 2, [Chemical Formula 2] In Chemical Formula 2, R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.

For example, when R ¹⁷ and R ¹⁸ are both alkyl or alkoxy, it may be difficult to achieve a green pixel for a color filter.

The compound represented by Chemical Formula 1 has excellent green spectral characteristics and a high Moire extinction coefficient. In addition, the compound represented by Chemical Formula 1 must contain at least two substituents represented by Chemical Formula 2 and thus can exhibit excellent solubility in an organic solvent and also excellent brightness and excellent pairing when applied to a color filter. ratio.

For example, when the compound represented by the above Chemical Formula 1 contains only one substituent represented by the Chemical Formula 2, the solubility, the brightness, and the contrast ratio in an organic solvent are greatly deteriorated and therefore, it can be used as a photosensitive resin for a color filter. Coloring agent in composition.

Chemical formula 2 can be represented by chemical formula 3: [Chemical formula 3] In Chemical Formula 3, R ¹⁷ produces a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁸ produces a substituted or unsubstituted C1 to C20 alkoxy group.

The substituent represented by Chemical Formula 3 has one alkyl group and one alkoxy group, the one alkyl group exists at the ortho position, and the one alkoxy group exists at the para position, and thus the brightness and contrast ratio can be further improved. . For example, when one alkyl group is present at the para position and one alkoxy group is present at the ortho position, it may be difficult to achieve a green pixel for a color filter.

For example, R ¹⁷ can produce tert-butyl. Compared with when R ¹⁷ is a branched alkyl group, such as t-butyl and the like, when R ¹⁷ is a linear alkyl group, such as methyl, ethyl, n-butyl, etc. ratio.

At least one of R ¹ to R ¹⁶ may be a substituted or unsubstituted C1 to C20 alkoxy group. For example, in Chemical Formula 1, compared to "when two of R ¹ to R ¹⁶ are represented by Chemical Formula 2 and the other substituents are halogen atoms", "two of R ¹ to R ¹⁶ are simultaneously As represented by Chemical Formula 2, when at least one of R ¹ to R ¹⁶ is an alkoxy group, sufficient solubility can be obtained.

Further, in Chemical Formula 1, when "at least four of R ¹ to R ¹⁶ are represented by Chemical Formula 2 (for example, at least one of R ¹ to R ⁴ may be represented by Chemical Formula 2 and at least one of R ⁵ to R ⁸ One may be represented by Chemical Formula 2, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2) ", the compound may have optimal solubility.

At least one of R ¹ to R ⁴ may be represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and R ¹³ to R At least one of ¹⁶ may be represented by Chemical Formula 2. For example, at least one of R ² and R ³ may be represented by Chemical Formula 2, at least one of R ⁶ and R ⁷ may be represented by Chemical Formula 2, and at least one of R ¹⁰ and R ¹¹ may be represented by Chemical Formula 2, and At least one of R ¹⁴ and R ¹⁵ may be represented by Chemical Formula 2.

At least one of R ¹ to R ⁴ may be a substituted or unsubstituted C1 to C20 alkoxy group, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² may Is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2. For example, at least one of R ² and R ³ may be a substituted or unsubstituted C1 to C20 alkoxy group, at least one of R ⁶ and R ⁷ may be represented by Chemical Formula 2, and R ¹⁰ and R ¹¹ At least one of may be represented by Chemical Formula 2, and at least one of R ¹⁴ and R ¹⁵ may be represented by Chemical Formula 2.

All of R ¹ to R ⁴ may be a halogen atom, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ One can be represented by Chemical Formula 2. For example, R ¹ to R ⁴ may each be a halogen atom, at least one of R ⁶ and R ⁷ may be represented by Chemical Formula 2, at least one of R ¹⁰ and R ¹¹ may be represented by Chemical Formula 2, and R ¹³ to R ¹⁶ may be a halogen atom.

All of R ¹ to R ⁸ may be a halogen atom, at least one of R ⁹ to R ¹² may be represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2. For example, R ¹ to R ⁸ may each be a halogen atom, at least one of R ¹⁰ and R ¹¹ may be a substituted or unsubstituted C1 to C20 alkoxy group, and at least one of R ¹⁴ and R ¹⁵ It can be represented by Chemical Formula 2.

All of R ¹ to R ⁴ may be a halogen atom, at least one of R ⁵ to R ⁸ may be represented by Chemical Formula 2, R ⁹ to R ¹² may be a halogen atom, and at least one of R ¹³ to R ¹⁶ may be represented by Chemical Formula 2 Means. For example, R ¹ to R ⁴ may be a halogen atom, at least one of R ⁶ and R ⁷ may be represented by Chemical Formula 2, R ⁹ to R ¹² may be a halogen atom, and at least one of R ¹⁴ and R ¹⁵ may be It is represented by Chemical formula 2.

For example, the compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 4 to Chemical Formula 11, but is not limited thereto: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] .

The compound according to an embodiment contains at least two substituents represented by Chemical Formula 2 and thus can achieve clearer colors in a smaller amount, and therefore, when used as a colorant, it can be manufactured with excellent color characteristics such as excellent brightness, Excellent contrast ratio, etc.). For example, the compound may be a colorant, such as a dye, such as a green dye, such as a dye having a maximum transmittance in a wavelength range of 445 nm to 560 nm.

In general, dyes are the most expensive of the components used in color filters. As a result, expensive dyes may need more to achieve the desired effects, such as high brightness, high contrast, etc., and therefore increase unit production costs. However, when the compound according to an embodiment is used as a dye in a color filter, the compound can achieve excellent color characteristics such as high brightness, high contrast, and the like, and reduce unit cost of production, even in a small amount use.

According to another embodiment, a photosensitive resin composition including the compound according to the embodiment is provided.

For example, the photosensitive resin composition may include the compound according to the embodiment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

The compound according to an embodiment functions as a colorant (for example, a dye, such as a green dye) in the photosensitive resin composition and can achieve excellent color characteristics.

The compound according to an embodiment may be included in an amount of 1 to 10% by weight, for example, 3 to 7% by weight based on the total amount of the photosensitive resin composition. When the compound according to an embodiment is included in the range, color reproducibility and contrast ratio are improved.

The photosensitive resin composition may further include a pigment, such as a yellow pigment, a green pigment, or a combination thereof.

The yellow pigment may include C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, and the like in the color index, and may be used alone or as a mixture of two or more.

The green pigment may include C.I. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment Green 59, and the like in the color index, and may be used alone or as a mixture of two or more.

The pigment may be contained in the photosensitive resin composition as a pigment dispersion.

The pigment dispersion liquid may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.

Based on the total amount of the pigment dispersion, it may be 1% to 20% by weight, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, such as 10% by weight to The solid content of 15% by weight contains pigments.

The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant, or the like. Specific examples of the dispersant may be polyalkylene glycol and its ester, polyoxyalkylene, polyhydric alcohol ester alkylene oxide addition product, alcohol alkylene oxide ) Addition products, sulfonate ester, sulfonate salt, carboxylate ester, carboxylate salt, alkylamide alkylene oxide addition Into products, alkyl amines, etc., and can be used alone or in the form of a mixture of two or more.

Commercial examples of the dispersant may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, manufactured by BYK Co., Ltd. DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc .; EFKA-47 manufactured by EFKA Chemicals Co. , EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc .; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse manufactured by Zeneka Co. 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc .; or PB711, PB821 manufactured by Ajinomoto Inc.

The dispersant may be included in an amount of 1 to 20% by weight based on the total weight of the pigment dispersion. When the dispersant is included in the range, the dispersion liquid of the photosensitive resin composition is improved due to an appropriate viscosity, and therefore, when the photosensitive resin composition is applied to a product, optical, physical, and chemical properties can be maintained quality.

The solvent used to form the pigment dispersion may be ethylene glycol acetate, ethylcellosolve, propylene glycol methyletheracetate, ethyllactate, Polyethylene glycol (polyethylene glycol), cyclohexanone (cyclohexanone), propylene glycol methyl ether (propylene glycol methylether) and so on.

The pigment dispersion liquid may be contained in an amount of 10 to 20% by weight (for example, 12 to 18% by weight) based on the total amount of the photosensitive resin composition. When the pigment dispersion liquid within the range is included, the process range can be secured, and color reproducibility and contrast ratio can be improved.

The alkali-soluble resin may be a propylene-based resin.

The propylene-based binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing at least one propylene-based repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer including at least one carboxyl group. Examples of the monomer include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5 to 50% by weight (for example, 10 to 40% by weight) based on the total amount of the propylene-based binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyl toluene, vinyl benzyl methyl ether (Vinylbenzylmethylether), etc .; unsaturated carboxylic acid ester compounds, such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate (Butyl (meth) acrylate), 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, ( Benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, etc .; unsaturated carboxylic acid Acid amino alkyl ester compounds, such as 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate), etc .; vinyl carboxylate compounds, such as vinyl acetate, vinyl benzoate (), etc .; unsaturated carboxylic acid condensation Water glyceride compounds, such as vinyl benzoate, etc .; vinyl cyanide compounds, such as (meth) acrylonitrile, etc .; unsaturated amidine compounds, For example, (meth) acrylamide, etc .; etc. These can be used alone or in the form of a mixture of two or more.

Specific examples of the propylene-based resin may be (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / methyl A benzyl acrylate / 2-hydroxyethyl methacrylate copolymer, a (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and the like are not limited thereto. These can be used alone or in the form of a mixture of two or more.

The weight-average molecular weight of the alkali-soluble resin may be in a range 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. When the alkali-soluble resin has a weight-average molecular weight within the range, the photosensitive resin composition may have excellent physical and chemical characteristics and appropriate viscosity, maintain appropriate developability and sensitivity, and exhibit during color filter manufacturing Excellent close contact with the substrate.

The alkali-soluble resin may have an acid value of 15 mgKOH / g to 60 mgKOH / g, such as 20 mgKOH / g to 50 mgKOH / g. When the alkali-soluble resin has an acid value within the range, the pixel has excellent resolution.

The alkali-soluble resin may be contained in an amount of 1 to 30% by weight, for example, 1 to 20% by weight based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is included in the above range, developability can be improved and excellent surface smoothness can be improved due to increased crosslinking during color filter manufacturing.

The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid containing at least one ethylenically unsaturated double bond.

The photopolymerizable compound has an ethylenically unsaturated double bond, and thus can cause sufficient polymerization during exposure during pattern formation and form a pattern having excellent heat resistance, light resistance, and chemical resistance.

Specific examples of the photopolymerizable compound may be 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 (Neopentyl glycol di (meth) acrylate), 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate , Pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate ), Dipentaerythritol di (meth) acrylate (dipe ntaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, hexa (meth) acrylate Dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate monomethylether (meth) acrylate), trimethylol propane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, Novolacepoxy (meth) acrylate, etc.

Examples of commercially available photopolymerizable compounds are as follows. The monofunctional (meth) acrylate may include Aronix M-101 ^® , M-111 ^® , M-114 ^® (Toagosei Chemistry Industry Co., Ltd.); KAYARAD TC-110S ^® , TC-120S ^® (Nippon Kayaku Co., Ltd.); V-158 ^® , V-2311 ^® (Osaka Organic Chemical Ind., Ltd.), etc. Examples of dysfunctional (meth) acrylates may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (Dongya Synthetic Chemical Industry Co., Ltd.), KAYARAD HDDA ^® , HX-220 ^® , R-604 ^® ( Nippon Kayaku Co., Ltd.), V-260 ^® , V-312 ^® , V-335HP ^® (Osaka Organic Chemical Co., Ltd.), etc. Examples of trifunctional (meth) acrylates may include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-710 ^® , M-8030 ^® , M-8060 ^® (East Asia Synthetic Chemical Industry Co., Ltd.), KAYARAD TMPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Kayaku Co., Ltd.), V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Yuki Kayaku Kogyo Co. Ltd.), etc. These can be used alone or in the form of a mixture of two or more.

The photopolymerizable compound may be treated with an acid anhydride to improve developability.

The photopolymerizable compound may be contained in an amount of 1 to 15% by weight, for example, 5 to 10% by weight based on the total amount of the photosensitive resin composition. When the photopolymerizable compound in the range is included, the photopolymerizable monomer is sufficiently cured during exposure during pattern formation and has excellent reliability, and the developability of the alkaline developer can be improved.

The photopolymerization initiator may be a photopolymerization initiator generally used in a photosensitive resin composition, such as an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, Oxime compounds, etc.

Examples of the acetophenone-based compound may be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylacetophenone, p-tert-butyl Trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (Methylthio) phenyl) -2-morpholinylpropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -but-1-one Wait.

Examples of the benzophenone-based compound may be benzophenone, benzophenone benzoate, benzophenethyl methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylic 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 thioxanthone compounds can produce thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-chlorothioxanthone and so on.

Examples of the benzoin-based compound may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.

Examples of the triazine compound may be 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (3 ', 4'-dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloro (Methyl) -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- (naphthol-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthol-yl) -4,6-bis (tris (Chloromethyl) -s-triazine, 2-4-bis (trichloromethyl) -6-piperonyl-s-triazine, 2-4-bis (trichloromethyl) -6- ( 4-methoxystyryl) -s-triazine and the like.

Examples of oxime compounds can produce O-fluorenyl oxime compounds, 2- (o-benzyl fluorenyl oxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (O-acetylamoxime) -1- [9-ethyl-6- (2-methylbenzyl) -9H-oxazol-3-yl] ethanone, O-ethoxycarbonyl-α-oxamine Phenyl-1-phenylpropan-1-one and the like. Specific examples of the O-fluorenyl oxime may be 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholine-4- -Phenyl) -butan-1-one, 1- (4-phenylthiophenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- (4-benzene (Thiophenyl) -octane-1,2-dione 2-oxime-O-benzoate, 1- (4-phenylthiophenyl) -oct-1-oneoxime-O-acetate , 1- (4-phenylthiophenyl) -butan-1-oneoxime-O-acetate, and the like.

In addition to the compound, the photopolymerization initiator may further include an oxazole-based compound, a dione-based compound, a fluorenyl borate compound, a diazonium-based compound, an imidazole-based compound, a biimidazole-based compound, a fluorene-based compound and the like.

The photopolymerization initiator may be used together with a photosensitizer capable of causing a chemical reaction by absorbing light and becoming an excited state and then transferring its energy.

Examples of the photosensitizer can produce tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, dipentaerythritol tetra-3-mercaptopropionate, and the like.

The photopolymerization initiator may be contained in an amount of 0.01 to 10% by weight, for example, 0.1 to 5% by weight based on the total amount of the photosensitive resin composition. When a photopolymerization initiator in the range is included, sufficient photopolymerization occurs during exposure in the pattern forming method, and excellent reliability may be achieved, which can improve the heat resistance, light resistance, and chemical resistance, resolution, and Close contact characteristics, and non-reactive initiator can prevent deterioration of transmittance.

The solvent is a material that is compatible with, but does not react with, the compound, pigment, alkali-soluble resin, photopolymerizable compound, and photopolymerization initiator according to an embodiment.

Examples of the solvent may include alcohols such as methanol, ethanol, etc .; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran, etc .; glycol ethers such as ethylene glycol monomethyl ether, Ethylene glycol monoethyl ether, etc .; Cellosolve acetates, such as methyl acetate, cellosolve ethyl acetate, cellosolve diethyl acetate, etc .; carbitols, such as methyl ethyl Carbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether Etc .; propylene glycol alkyl ether acetates, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc .; aromatic hydrocarbons, such as toluene, xylene, etc .; ketones, such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl n-acetone, methyl n-butanone, methyl n-pentanone, 2-heptanone, etc .; saturated aliphatic monocarboxylic acid alkyl esters, such as ethyl acetate Esters, n-butyl acetate, isobutyl acetate, etc .; lactate esters, such as methyl lactate, ethyl lactate, etc .; alkyloxyacetates, such as methyloxyacetate, oxygen Ethyl acetoacetate, butyl oxyacetate, etc .; alkyl alkoxyacetates, such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl acetate Ethyl ethoxylate, etc .; alkyl 3-oxypropionate, such as methyl 3-oxypropionate, ethyl 3-oxypropionate, etc .; alkyl 3-alkoxypropionate, such as 3 -Methyl methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc .; alkyl 2-oxypropionate, For example, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc .; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate , Ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc .; 2-oxy-2-methylpropionate, such as 2-oxy Methyl-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, etc .; monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-methylalkylpropionate , Such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc .; esters, such as 2-hydroxyethyl propionate, 2-hydroxy-propionate- 2-methyl ethyl ester, hydroxy ethyl acetate , 2-hydroxy-butyric acid methyl ester and the like; ketones esters, such as acetone and ethyl. In addition, high boiling point solvents such as N-methylformamide, N, N-dimethylformamide, N-methylformanilide (N -methylformanilide), N-methylacetamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylmethylene (Dimethylsulfoxide), benzylethylether, dihexylether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octyl Alcohol (1-octanol), 1-nonanol, 1-nonanol, benzylalcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, Diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, ethylene glycol ether phenyl acetate ( phenyl cellosolve acetate).

In view of miscibility and reactivity, glycol ethers, such as ethylene glycol monoethyl ether, etc .; ethylene glycol alkyl ether acetates, such as ethyl glycol ethyl ether, etc .; esters, such as propionic acid 2 -Hydroxyethyl, etc .; carbitol, such as diethylene glycol monomethyl ether, etc .; propylene glycol alkyl ether acetates, such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate; and / or ketones, such as Cyclohexanone.

The solvent is used in the balance, for example, 30% to 80% by weight based on the total amount of the photosensitive resin composition. When the solvent is included in the range, the photosensitive resin composition may have an appropriate viscosity, thereby improving the coating characteristics of the color filter.

The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve close contact characteristics with the substrate.

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

The epoxy compound may be contained in an amount of 0.01 to 20 parts by weight and, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When an epoxy compound within the range is included, close contact characteristics, storage characteristics, and the like can be improved.

In addition, the photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryl group, an isocyanate group, and an epoxy group to improve adhesion to the substrate.

Examples of the silane-based coupling agent may include trimethoxysilylbenzoic acid, γ-methacrylpropoxytrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyl Triethoxysilane, γ-glycidyloxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and the like. These can be used alone or in the form of a mixture of two or more.

The silane coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is included in the range, close contact characteristics, storage characteristics, and the like may be excellent.

In addition, if necessary, the photosensitive resin composition may further include a surfactant to improve coating characteristics and prevent defects.

Examples of the surfactant may be BM-1000 ^® and BM-1100 ^® (BM Chemie Inc.); MEGAFACE F 142D ^® , F 172 ^® , F 173 ^®, and F 183 ^® (Da Nihon Ink Chemical Company) (Dainippon Ink Kagaku Kogyo Co., Ltd.)); FULORAD FC-135 ^® , FULORAD FC-170C ^® , FULORAD FC-430 ^®, and FULORAD FC-431 ^® (Sumitomo 3M Co., Ltd.) ); SURFLON S-112 ^® , SURFLON S-113 ^® , SURFLON S-131 ^® , SURFLON S-141 ^® and SURFLON S-145 ^® (ASAHI Glass Co., Ltd.); and SH-28PA ^® , SH-190 ^® , SH-193 ^® , SZ-6032 ^® and SF-8428 ^® (Toray Silicone Co., Ltd.); Dainippon Ink Chemical Industry Co., Ltd. (DIC Co. , Ltd.) F-482, F-484, F-478, F-554, etc.

The surfactant may be contained in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When a surfactant in the range is included, it is excellent to ensure coating uniformity, no staining is found, and wetting characteristics of a glass substrate.

In addition, the photosensitive resin composition may further include other additives such as an oxidation inhibitor, a stabilizer, and the like in a predetermined amount unless the characteristics are deteriorated.

According to another embodiment, a color filter manufactured using the photosensitive resin composition according to the embodiment is provided.

The pattern forming method of the color filter is as follows.

The method includes applying a photosensitive resin composition according to an embodiment on a support substrate by a method such as spin coating, slit coating, inkjet printing, and drying the applied positive photosensitive resin composition to form a photosensitive property. A resin composition film; exposing the positive photosensitive resin composition film; developing the exposed positive photosensitive resin composition film in an alkaline aqueous solution to obtain a photosensitive resin layer; and heat-treating the photosensitive resin layer. The conditions for the patterning method are well known in the related art and will not be described in detail in this specification.

In the following, the present invention is explained in more detail with reference to examples, however, these examples do not interpret the meaning in any way to limit the scope of the present invention. (Synthesis of Compound) Synthesis Example 1-1: Synthesis of 3,4,6-trichloro-5- (4-methoxy-2-methyl - phenoxy) - phthalonitrile

Add 3,4,5,6-tetrachlorophthalonitrile (3,4,5,6-tetrachlorophthalonitrile) (5 g), 4-methoxy-2-methylphenol ) (3.12 g), K ₂ CO ₃ (3.9 g), and N, N-dimethylformamide (25 ml) were placed in a 100 ml flask and then heated with stirring at 70 ° C. When the reaction is complete, EA (ethyl acetate) is used for extraction. After extraction, a solid was obtained by concentration. Herein, the obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 3,4,6-trichloro-5- (4-methoxy-2- Methyl-phenoxy) -phthalonitrile. Synthesis Example 1-2: Synthesis of 4- (2-tert-butyl-4-methoxy-phenoxy) - 3,5,6-trichloro - phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-tert-butyl-4-methoxyphenol (4.07 g), K ₂ CO ₃ (3.9 g), N, N -Dimethylformamide (25 ml) was placed in a 100 ml flask and then heated with stirring at 70 ° C. When the reaction was complete, EA (ethyl acetate) was used for extraction. After extraction, a solid was obtained by concentration. Herein, the obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 4- (2-tert-butyl-4-methoxy-phenoxy)- 3,5,6-trichloro-phthalonitrile. Synthesis Example 1 : Synthesis of a compound represented by Chemical Formula 4

3,4,6-trichloro-5- (4-methoxy-2-methyl-phenoxy) -phthalonitrile (2 g), 1,8- Diazabicycloundec-7-ene (1.04 g) and 1-pentenol (10 g) were placed in a 100 ml flask and subsequently heated at 90 ° C to dissolve the solids, zinc acetate (0.25 g) It was added thereto, and the mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, dichloromethane was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 4. [Chemical Formula 4] Maldi-tof MS: 1527.82 m / z Synthesis Example 2 : Synthesis of a compound represented by Chemical Formula 5

3,4,6-trichloro-5- (4-methoxy-2-methyl-phenoxy) -phthalonitrile (1.5 g), 3,4, 5,6-tetrachlorophthalonitrile (0.36 g), 1,8-diazabicycloundec-7-ene (1.04 g) and 1-pentenol (14 g) were placed in a 100 ml flask The solid was dissolved by heating at 90 ° C, zinc acetate (0.25 g) was added thereto, and the mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 5. [Chemical Formula 5] Maldi-tof MS: 1425.72 m / z Synthesis Example 3 : Synthesis of a compound represented by Chemical Formula 6

3,4,6-trichloro-5- (4-methoxy-2-methyl-phenoxy) -phthalonitrile (1.1 g), 3,4, 5,6-tetrachlorophthalonitrile (0.80 g), 1,8-diazabicycloundec-7-ene (1.14 g) and 1-pentenol (14 g) were placed in a 100 ml flask The mixture was heated at 90 ° C to dissolve the solid, zinc acetate (0.27 g) was added thereto, and the obtained mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 6. [Chemical Formula 6] Maldi-tof MS: 1323.64 m / z Synthesis Example 4 : Synthesis of a compound represented by Chemical Formula 7

3,4,6-trichloro-5- (4-methoxy-2-methyl-phenoxy) -phthalonitrile (1.5 g), 3,4, 6-Trichloro-5-pentyloxy-phthalonitrile (0.43 g), 1,8-diazabicycloundec-7-ene (1.04 g) and 1-pentenol (14 g) In a 100 ml flask and heated at 90 ° C, after the solid was dissolved, zinc acetate (0.25 g) was added thereto, and the obtained mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 7. [Chemical Formula 7] Maldi-tof MS: 1477.84 m / z Synthesis Example 5 : Synthesis of a compound represented by Chemical Formula 8

4- (2-tert-butyl-4-methoxy-phenoxy) -3,5,6-trichloro-phthalonitrile (2 g), 1,8 according to Synthesis Example 1-2 -Diazabicycloundec-7-ene (0.93 g) and 1-pentenol (10 g) were placed in a 100 ml flask and subsequently heated at 90 ° C to dissolve the solids, zinc acetate (0.22 g ) Was added thereto, and the obtained mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 8. [Chemical Formula 8] Maldi-tof MS: 1696.01 m / z Synthesis Example 6 : Synthesis of a compound represented by Chemical Formula 9

4- (2-tert-butyl-4-methoxy-phenoxy) -3,5,6-trichloro-phthalonitrile (1.5 g), 3,4 according to Synthesis Example 1-2 , 5,6-tetrachlorophthalonitrile (0.32 g), 1,8-diazabicycloundec-7-ene (0.93 g) and 1-pentenol (14 g) were placed in 100 ml of The solid was dissolved in a flask and heated at 90 ° C, zinc acetate (0.22 g) was added thereto, and the obtained mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, dichloromethane was appropriately added to the obtained solid, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 9. [Chemical Formula 9] Maldi-tof MS: 1551.87 m / z Synthesis Example 7 : Synthesis of a compound represented by Chemical Formula 10

4- (2-tert-butyl-4-methoxy-phenoxy) -3,5,6-trichloro-phthalonitrile (1.1 g), 3,4 according to Synthesis Example 1-2 , 5,6-tetrachlorophthalonitrile (0.71 g), 1,8-diazabicycloundec-7-ene (1.02 g) and 1-pentenol (14 g) were placed in 100 ml of The solid was dissolved in a flask and heated at 90 ° C, zinc acetate (0.25 g) was added thereto, and the obtained mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 10. [Chemical Formula 10] Maldi-tof MS: 1407.73 m / z Synthesis Example 8 : Synthesis of a compound represented by Chemical Formula 11

3,4,6-trichloro-5- (4-methoxy-2-methyl-phenoxy) -phthalonitrile (1.5 g), 3,4, 6-trichloro-5-pentyloxy-phthalonitrile (0.39 g), 1,8-diazabicycloundec-7-ene (0.93 g) and 1-pentenol (14 g) The solid was dissolved in a 100 ml flask and heated at 90 ° C, zinc acetate (0.22 g) was added thereto, and the obtained mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, dichloromethane was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 11. [Chemical Formula 11] Maldi-tof MS: 1603.98 m / z Comparative Synthesis Example 1 : Synthesis of a compound represented by Chemical Formula C-1

Add 4- (2-sec-butyl-phenoxy) -3,5,6-trichloro-phthalonitrile (1 g), 1,8-diazabicycloundec-7-ene (0.30 G), 1-pentenol (7 g), zinc acetate (0.12 g) were placed in a 100 ml flask and heated at 140 ° C with stirring. When the reaction was completed, the resultant was concentrated and purified by column chromatography. After purification, the obtained liquid was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula C-1. [Chemical Formula C-1] Maldi-tof MS: 1584.04 m / z Comparative Synthesis Example 2 : Synthesis of a compound represented by Chemical Formula C-2

Add 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-dimethylphenol (2.75 g), K ₂ CO ₃ (3.9 g), and N, N-dimethyl Formamidine (25 ml) was placed in a 100 ml flask and then heated with stirring at 70 ° C. When the reaction was complete, EA (ethyl acetate) was used for extraction. After extraction, a solid was obtained by concentration. Herein, the obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 3,4,6-trichloro-5- (2,4-dimethyl- (Phenoxy) -phthalonitrile.

Add 3,4,6-trichloro-5- (2,4-dimethyl-phenoxy) -phthalonitrile (1 g), 1,8-diazabicycloundec-7-7- Ene (1.08 g) and 1-pentenol (14 g) were placed in a 100 ml flask and heated at 90 ° C to dissolve the solid, zinc acetate (0.26 g) was added thereto, and at 140 ° C The mixture was heated while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula C-2. [Chemical Formula C-2] Maldi-tof MS: 1463.84 m / z Comparative Synthesis Example 3 : Synthesis of a compound represented by Chemical Formula C-3

Add 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-dimethylphenol (3.47 g), K ₂ CO ₃ (3.9 g), and N, N-dimethyl Formamidine (25 ml) was placed in a 100 ml flask and then heated with stirring at 70 ° C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, a solid was obtained by concentration. Herein, the obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 3,4,6-trichloro-5- (2,4-dimethoxy -Phenoxy) -phthalonitrile.

Add 3,4,6-trichloro-5- (2,4-dimethoxy-phenoxy) -phthalonitrile (2 g), 1,8-diazabicycloundec-7 -Ene (0.99 g) and 1-pentenol (14 g) were placed in a 100 ml flask and heated at 90 ° C to dissolve the solid, zinc acetate (0.24 g) was added thereto, and at 140 ° C The mixture was heated while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, dichloromethane was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula C-3. [Chemical Formula C-3] Maldi-tof MS: 1591.80 m / z Comparative Synthesis Example 4 : Synthesis of a compound represented by Chemical Formula C-4

4- (2-tert-butyl-4-methoxy-phenoxy) -3,5,6-trichloro-phthalonitrile (0.7 g), 3,4 according to Synthesis Example 1-2 , 5,6-tetrachlorophthalonitrile (1.45 g), 1,8-diazabicycloundec-7-ene (1.38 g) and 1-pentenol (14 g) were placed in 100 ml of The solid was dissolved in a flask and heated at 90 ° C, zinc acetate (0.33 g) was added thereto, and the mixture was heated at 140 ° C while stirring. When the reaction was complete, the precipitate was confirmed with methanol, filtered and dried under vacuum. The dried solid was purified by column chromatography. After purification, methylene chloride was appropriately added to the obtained solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula C-4. [Chemical Formula C-4] Maldi-tof MS: 1237.54 m / z evaluation 1 : solubility

A diluted solvent (PGMEA) was added to 0.5 g of each of the compounds according to Synthesis Example 1 to Synthesis Example 8 and Comparative Synthesis Example 1 to Comparative Synthesis Example 4, and each corresponding solution thus obtained used a hybrid rotor (hybrid rotor VMR-5, Iuchi Seieido Co., Ltd.) was stirred at 25 ° C and 100 rpm for 1 hour, and the solubility results of each compound are shown in Table 1.

Reference for solubility evaluation: Dissolve compounds (solutes) greater than or equal to 10% by weight based on the total amount of diluted solvent: ○ Dissolve compounds (solutes) greater than or equal to 5% by weight and less than 10% by weight based on the total amount of diluted solvent: △ Compounds (solutes) that dissolve less than 5% by weight based on the total amount of the diluted solvent: X

[Table 1] (Unit:% by weight)

Referring to Table 1, compared with the compounds of Comparative Synthesis Example 1 to Comparative Synthesis Example 4, the compounds of Synthesis Example 1 to Synthesis Example 8 were produced. The compounds according to one embodiment showed excellent solubility in organic solvents, and therefore when It exhibits excellent color characteristics when used for photosensitive resin compositions. (Synthetic photosensitive resin composition) Example 1

The following components were mixed in the composition shown in Table 2 to prepare a photosensitive resin composition according to Example 1.

Specifically, the photopolymerization initiator was dissolved in a solvent, the solution was stirred at room temperature for 2 hours, an alkali-soluble resin and a photopolymerizable compound were added thereto, and the obtained mixture was stirred at room temperature for 2 hours. Subsequently, the compound of Synthesis Example 1 (a compound represented by Chemical Formula 4) was added to the reactant as a colorant and a pigment (pigment dispersion liquid), and the obtained mixture was stirred at room temperature for 1 hour. Next, the obtained product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

[Table 2] (Unit:% by weight) Example 2

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Synthesis Example 2 (a compound represented by Chemical Formula 5) was used instead of the compound of Synthesis Example 1 (a compound represented by Chemical Formula 4). Example 3

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Synthesis Example 3 (the compound represented by Chemical Formula 6) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Example 4

A photosensitive resin composition was prepared according to the same method as in Example 1, except that the compound of Synthesis Example 4 (the compound represented by Chemical Formula 7) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Example 5

A photosensitive resin composition was prepared according to the same method as in Example 1, except that the compound of Synthesis Example 5 (a compound represented by Chemical Formula 8) was used instead of the compound of Synthesis Example 1 (a compound represented by Chemical Formula 4). Example 6

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Synthesis Example 6 (the compound represented by Chemical Formula 9) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Example 7

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Synthesis Example 7 (the compound represented by Chemical Formula 10) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Example 8

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Synthesis Example 8 (the compound represented by Chemical Formula 11) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Comparative Example 1

A photosensitive resin composition was prepared according to the same method as in Example 1, except that the compound of Comparative Synthesis Example 1 (the compound represented by Chemical Formula C-1) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Comparative Example 2

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Comparative Synthesis Example 2 (the compound represented by Chemical Formula C-2) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Comparative Example 3

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Comparative Synthesis Example 3 (the compound represented by Chemical Formula C-3) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Comparative Example 4

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the compound of Comparative Synthesis Example 4 (the compound represented by Chemical Formula C-4) was used instead of the compound of Synthesis Example 1 (the compound represented by Chemical Formula 4). Comparative Example 5

A photosensitive resin composition was prepared according to the same method as in Example 1 except that the composition shown in Table 3 was used instead of the composition shown in Table 1. [Table 3] (Unit:% by weight) Comparative Example 6

A photosensitive resin composition was prepared in the same manner as in Comparative Example 5 except that the pigment dispersion liquid pigment G36 was used instead of the pigment dispersion liquid pigment G58. Evaluation 2 : color coordinates, brightness, and contrast ratio

The photosensitive resin compositions of Examples 1 to 8 and Comparative Examples 1 to 6 were coated on degreased and clean glass substrates having a thickness of 1 to 3 microns and 1 mm, respectively, and then on a 90 ° C hot plate Dry for 2 minutes to obtain each film. Subsequently, the film was exposed by using a high-pressure mercury lamp having a dominant wavelength of 365 nanometers. Subsequently, the film was dried in a forced convection drying boiler at 200 ° C for 5 minutes to obtain a sample. The brightness (Y) and contrast ratio of the pixel layer were measured by using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are shown in Table 4.

[Table 4]

Referring to Table 4, compared to the photosensitive resin composition according to Comparative Examples 1 to 6 which does not include the compound, the photosensitive resin composition including the example compound for producing a dye according to Examples 1 to 8 is shown. Excellent color characteristics.

Although the present invention has been described in connection with the present practical practical embodiments, it should be understood that the present invention is not limited to the disclosed embodiments, but rather, the present invention is intended to cover the spirit and scope included in the scope of the appended patents Various modifications and equivalent arrangements within.

no.

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Claims (18)

A compound represented by Chemical Formula 1: [Chemical Formula 1] Among them, in Chemical Formula 1, R ¹ to R ^{16 are} independently halogen atoms, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, at least two of the restrictions R ¹ to R ¹⁶ are represented by Chemical Formula 2, [Chemical Formula 2] Among them, in Chemical Formula 2, R ¹⁷ generates a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁸ generates a substituted or unsubstituted C1 to C20 alkoxy group. The compound according to item 1 of the scope of patent application, wherein Chemical Formula 2 is represented by Chemical Formula 3: [Chemical Formula 3] Among them, in Chemical Formula 3, R ¹⁷ produces a substituted or unsubstituted C1 to C20 alkyl group, and R ¹⁸ produces a substituted or unsubstituted C1 to C20 alkoxy group. The compound as described in claim 1 in which R ¹⁷ produces tert-butyl. The compound according to item 1 of the scope of patent application, wherein at least one of R ¹ to R ¹⁶ is a substituted or unsubstituted C1 to C20 alkoxy group. The compound according to item 1 of the patent application range, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² Is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2. The compound according to item 1 of the scope of patent application, wherein at least one of R ¹ to R ⁴ generates a substituted or unsubstituted C1 to C20 alkoxy group, and at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2 It means that at least one of R ⁹ to R ¹² is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2. The compound according to item 1 of the scope of patent application, wherein R ¹ to R ⁴ generate a halogen atom, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² is represented by Chemical Formula 2. And at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2. The compound according to item 1 of the patent application range, wherein R ¹ to R ⁸ generate a halogen atom, at least one of R ⁹ to R ¹² is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2 Means. The compound according to item 1 of the scope of patent application, wherein R ¹ to R ⁴ generate a halogen atom, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, R ⁹ to R ¹² generate a halogen atom, and R ¹³ to At least one of R ¹⁶ is represented by Chemical Formula 2. The compound according to item 1 of the scope of patent application, wherein the compound represented by Chemical Formula 1 is represented by one of Chemical Formula 4 to Chemical Formula 11: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] . The compound according to item 1 of the scope of patent application, wherein the compound is a green dye. The compound according to item 11 of the patent application range, wherein the green dye has a maximum transmittance in a wavelength range of 445 nm to 560 nm. A photosensitive resin composition comprising the compound according to any one of claims 1 to 12 of the scope of patent application. The photosensitive resin composition according to item 13 of the scope of application for a patent, wherein the compound is contained in an amount of 1% to 10% by weight based on the total amount of the photosensitive resin composition. The photosensitive resin composition according to item 13 of the scope of application for a patent, wherein the photosensitive resin composition further includes an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The photosensitive resin composition according to item 15 of the scope of patent application, wherein the photosensitive resin composition further includes a pigment. The photosensitive resin composition according to item 16 of the scope of patent application, wherein the pigment includes a yellow pigment, a green pigment, or a combination thereof. A color filter is manufactured using the photosensitive resin composition according to item 13 of the scope of patent application.