TW201638095A - Novel compound, photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

A compound represented by Chemical Formula 1, a photosensitive resin composition including the same, and a color filter manufactured using the photosensitive resin composition are provided. [Chemical Formula 1] In Chemical Formula 1, each substituent is the same as defined in the detailed description.

Description

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

The present invention relates to a novel compound, a photosensitive resin composition containing the compound, and a color filter.

A color filter manufactured by using a photosensitive type photosensitive resin composition has a limitation in brightness and contrast ratio due to the particle diameter of the pigment. In addition, the imaging sensor device requires a smaller dispersed particle size to form a fine pattern.

In order to satisfy the demand, it has been attempted to realize a color filter having improved color characteristics such as brightness, contrast ratio, and the like by fabricating a photosensitive resin composition by introducing a dye which does not form particles instead of a pigment.

Therefore, it is necessary to study a suitable compound which is used as a dye for producing a photosensitive resin composition.

One embodiment provides a novel compound.

Another embodiment provides a photosensitive resin composition comprising the compound.

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

One embodiment of the present invention provides a compound represented by Chemical Formula 1. [Chemical Formula 1]

In Chemical Formula 1, M is Cu, Zn, Co or Mo, and R ¹ to R ^{16 are} independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or unsubstituted C6-C20 aryl or a substituted or unsubstituted C6-C20 aryloxy group, and R ¹ to R ^{16 is} at least one represented by chemical formula 2, [ Chemical formula 2] Wherein, in Chemical Formula 2, R ¹⁷ and R ^{18 are} independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

Chemical Formula 2 can be represented by Chemical Formula 3. [Chemical Formula 3]

In Chemical Formula 3, R ¹⁷ and R ^{18 are} independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

At least one of R ¹ to R ¹⁶ may be represented by Chemical Formula 2, and at least one of R ¹ to R ¹⁶ may be represented by one of Chemical Formula 4 to Chemical Formula 7. [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7]

In Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group.

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 may be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ⁹ to R ¹² may be Chemical Formula 4 One of Chemical Formula 7 indicates that at least one of R ¹³ to R ¹⁶ may be represented by one of Chemical Formula 4 to Chemical Formula 7.

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, and at least one of R ⁹ to R ¹² may be represented by Chemical Formula 4 to Chemical Formula 7, and R At least one of ¹³ to R ¹⁶ may be represented by one of Chemical Formula 4 to Chemical Formula 7.

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 may be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ⁹ to R ¹² may be Chemical Formula 2 Represented, and at least one of R ¹³ to R ¹⁶ may be represented by one of Chemical Formula 4 to Chemical Formula 7.

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, and 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 one of Chemical Formula 4 to Chemical Formula 7.

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, and 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 can be represented by Chemical Formula 2.

The compound represented by Chemical Formula 1 can be represented by one of Chemical Formula 8 to Chemical Formula 16. [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16]

The compound can be a green dye.

Green dyes have maximum light transmission at wavelengths from 445 nm to 560 nm.

Another embodiment provides a photosensitive resin composition comprising the compound.

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

The photosensitive resin composition may further contain a pigment.

The pigment can be a yellow pigment.

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

Other embodiments of the invention are included in the following embodiments.

The compound according to one embodiment has excellent green spectral characteristics, high molar extinction coefficient, and improved organic solvent solubility, and thus can be used as a dye during preparation of a photosensitive resin composition for a green filter, And the color filter containing the dye can have excellent brightness and contrast ratio.

Embodiments of the invention are described in detail below. However, these embodiments are exemplary, and the invention is not limited thereto.

As used herein, the term "substituted", when not specifically defined otherwise, is substituted with a substituent selected from the group consisting of halogen (F, Br, Cl or I), hydroxy, nitro, cyano, amine ( NH ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different and independently C 1 to C 10 alkyl), indenyl, fluorenyl , mercapto, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic group, The substituted or unsubstituted aryl group and the substituted or unsubstituted heterocyclic group are substituted for the functional group of the present invention.

As used herein, the term "alkyl" refers to a C1 to C20 alkyl group and, in particular, a C1 to C15 alkyl group, and the term "cycloalkyl" refers to a C3 to C20 cycloalkyl group and is specific when a specific definition is not otherwise provided. The C3 to C18 cycloalkyl group, the term "alkoxy" means a C1 to C20 alkoxy group and specifically a C1 to C18 alkoxy group, and the term "aryl group" means a C6 to C20 aryl group and specifically C6 to C18 aryl, the term "alkenyl" means C2 to C20 alkenyl and specifically C2 to C18 alkenyl, and the term "alkylene" means C1 to C20 alkyl and specifically C1 to C18 Alkyl, and the term "extended aryl" refers to a C6 to C20 extended aryl group and, in particular, a C6 to C16 extended aryl group.

As used herein, "(meth)acrylate" means "acrylate" or "methacrylate" and "(meth)acrylic" means "acrylic" or "methyl" when no specific definition is provided. acrylic acid".

As used herein, the term "combination" refers to mixing or copolymerization when the definition is not otherwise provided. Further, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means a block copolymer or a random copolymer.

In the chemical formula of the present specification, unless a specific definition is additionally provided, when a chemical bond is not drawn at a position to be given, hydrogen bonding is at the position.

As used herein, "*" indicates a point connecting the same or different atoms or chemical formulas when no specific definition is provided.

One embodiment provides a compound represented by Chemical Formula 1. [Chemical Formula 1]

In Chemical Formula 1, M is Cu, Zn, Co or Mo, and R ¹ to R ^{16 are} independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or unsubstituted C6-C20 aryl or a substituted or unsubstituted C6-C20 aryloxy group, and R ¹ to R ^{16 is} at least one represented by chemical formula 2, [ Chemical formula 2] Wherein, in Chemical Formula 2, R ¹⁷ and R ^{18 are} independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by Chemical Formula 1 has excellent green spectral characteristics and a high molar extinction coefficient. Further, the compound represented by Chemical Formula 1 must contain the substituent represented by Chemical Formula 2 and thus may have improved solubility in an organic solvent, and exhibit excellent brightness when applied to a color filter.

In an exemplary embodiment, M can be Zn.

Chemical Formula 2 can be represented by Chemical Formula 3. [Chemical Formula 3]

In Chemical Formula 3, R ¹⁷ and R ^{18 are} independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by Chemical Formula 1 according to one embodiment must contain a substituent represented by Chemical Formula 2 (for example, Chemical Formula 3) and cause red-shift, and thus, compared with a composition containing a pigment such as a green pigment, The compound represented by Chemical Formula 1 according to one embodiment showed excellent brightness.

Further, the compound represented by Chemical Formula 1 according to one embodiment must contain a substituent represented by Chemical Formula 2 (for example, Chemical Formula 3) and exhibit greatly improved solubility in an organic solvent, and a phthalocyanine-based dye compound containing a decylamine substituent. The solubility in an organic solvent is drastically deteriorated.

R ¹ to R ¹⁶ may be represented by Chemical Formula 2, and R ¹ to R ¹⁶ may be at least one of the chemical formulas 4 to 7 one represented by the chemical formula. [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7]

In Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group.

For example, L ¹ may be substituted or unsubstituted methylene, substituted or unsubstituted extended ethyl, substituted or unsubstituted extended propyl, substituted or unsubstituted butyl Substituted, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted Substituted thiol or substituted or unsubstituted thiol.

In addition to the substituent represented by Chemical Formula 2, the compound according to one embodiment further contains a substituent represented by one of Chemical Formula 4 to Chemical Formula 7 and can increase solubility in an organic solvent and improve coloring characteristics.

For example, in Chemical Formula 1, R ¹ to R ⁴ may be represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ may be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ⁹ to R ¹² One may be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ¹³ to R ¹⁶ may be represented by one of Chemical Formula 4 to Chemical Formula 7.

For example, in Chemical Formula 1, 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, and at least one of R ⁹ to R ¹² may be Chemical Formula 4 to Chemical Formula 7. One of them is represented, and at least one of R ¹³ to R ¹⁶ may be represented by one of Chemical Formula 4 to Chemical Formula 7.

For example, in Chemical Formula 1, R ¹ to R ⁴ may be represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ may be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ⁹ to R ¹² It can be represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ can be represented by one of Chemical Formula 4 to Chemical Formula 7.

For example, in Chemical Formula 1, 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, and 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 one of Chemical Formula 4 to Chemical Formula 7.

For example, in Chemical Formula 1, 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, and 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, the compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 8 to Chemical Formula 16, but is not limited thereto. [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16]

Since the compound according to one embodiment can achieve a clearer color by a smaller amount than the substituent represented by Chemical Formula 2 (for example, Chemical Formula 3), it can be produced with excellent color characteristics by using the compound as a colorant. A display device (such as brightness, contrast ratio, etc.). For example, the compound can be a colorant, such as a dye, such as a green dye that can have, for example, a maximum light transmission in the wavelength range of 445 nm to 560 nm.

In general, dyes are the most expensive of the components used in color filters. Therefore, it may be desirable to use more expensive dyes to achieve desired effects, such as high brightness, high contrast ratios, and the like, and thus increase unit production costs. However, when a compound according to one embodiment is used as a dye for a color filter, the compound can achieve excellent color characteristics (such as high brightness, high contrast ratio, etc.) and reduce unit production cost even in a small amount.

Further, the compound according to one embodiment may contain a substituent represented by one of Chemical Formula 4 to Chemical Formula 7 in addition to the substituent represented by Chemical Formula 2 (for example, Chemical Formula 3), and thus may be modified in an organic solvent. Solubility and improved coloring properties.

According to one embodiment, a photosensitive resin composition comprising the compound according to the above embodiment is provided.

For example, the photosensitive resin composition contains the compound according to the above examples, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

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

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

The photosensitive resin composition may further contain a pigment such as a yellow pigment.

The yellow pigment may be C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment Yellow 150, and the like in the color index, and these pigments may be used singly or in the form of a mixture of two or more.

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

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

It may comprise from 1% by weight to 20% by weight, for example from 8% by weight to 20% by weight, for example from 8% by weight to 15% by weight, such as from 10% by weight to 20% by weight and for example 10% by weight, based on the total amount of the pigment dispersion A solid pigment in an amount of 15% by weight.

The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant, or the like. Specific examples of the dispersant may be a polyalkylene glycol and its ester, a polyalkylene oxide, a polyol ester alkylene oxide addition product, an alcohol alkylene oxide addition product, a sulfonate, a sulfonate, a carboxylate, a carboxylate An acid salt, an alkylguanamine alkylene oxide addition product, an alkylamine or the like, and may be used singly or in the form of a mixture of two or more.

Commercially available examples of the dispersing agent 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, manufactured by Zeneka Co., Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; or PB711, PB821, etc. manufactured by Ajinomoto Inc.

The dispersant may be included in an amount of from 1% by weight to 20% by weight based on the total amount of the pigment dispersion. When the dispersant in the above range is contained, the dispersion of the photosensitive resin composition can be improved due to the appropriate viscosity, and thus the optical and physicochemical qualities of the article can be maintained.

The solvent used for the pigment dispersion may be ethylene glycol acetate, ethylenecellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc. Wait.

The pigment dispersion may be contained in an amount of 10% by weight to 20% by weight, for example, 12% by weight to 18% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion in the range is contained, the process margin is advantageously ensured and the color reproducibility and the contrast ratio become excellent.

The alkali-soluble resin may be an acrylic resin.

The acrylic 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 acrylic repeating unit.

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

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

The diene unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, vinylbenzyl methyl ether or the like; an unsaturated carboxylic acid ester compound such as ( Methyl)methyl acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, (meth)acrylic acid Benzyl methyl ester, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, etc.; aminoalkyl ester of unsaturated carboxylic acid, such as 2-aminoethyl (meth) acrylate, (methyl) ) 2-dimethylaminoethyl acrylate or the like; a vinyl carboxylate compound such as vinyl acetate, vinyl benzoate or the like; an unsaturated carboxylic acid glycidyl ester compound such as glycidyl (meth)acrylate Esters and the like; vinyl cyanide compounds such as (meth)acrylonitrile and the like; unsaturated guanamine compounds such as (meth) acrylamide, etc.; and the like, and either alone or in both or more than two The mixture is used in the form of a mixture.

Specific examples of the acrylic resin may be acrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, methyl group Acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc., but not limited to this. These may be used singly or in the form of a mixture of two or more.

The acrylic resin may have a weight average molecular weight of from 3,000 g/mol to 150,000 g/mol, for example from 5,000 g/mol to 50,000 g/mol, and further, for example, from 20,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the acrylic resin is within the above range, the photosensitive resin composition for a color filter has good physical and chemical characteristics, appropriate viscosity, and close contact with the substrate during color filter manufacturing. characteristic.

The acrylic resin may have an acid value of from 15 mg KOH/g to 60 mg KOH/g, for example from 20 mg KOH/g to 50 mg KOH/g. When the acid value of the acrylic resin is within the range, the pixel pattern can have excellent resolution.

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

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 the exposure of the pattern forming process 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(methyl). Acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A II Methyl) acrylate, pentaerythritol di(meth) acrylate, pentaerythritol tri(meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate Ester, dipentaerythritol tri(meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl Ether (meth) acrylate, trimethylolpropane tri(meth) acrylate, tris(meth) propylene methoxyethyl phosphate, phenol aldehyde epoxy (meth) acrylate, and the like.

Commercially available examples of photopolymerizable compounds are as follows. Examples of the (meth)acrylic monofunctional ester 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 the (meth)acrylic difunctional ester may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (East Asia Synthetic Chemical Co., Ltd.); KAYARAD HDDA ^® , HX-220 ^® , R-604 ^® (Japan) Chemicals Co., Ltd.; V-260 ^® , V-312 ^® , V-335 HP ^® (Osaka Organic Chemical Co., Ltd.), etc. Examples of trifunctional esters of (meth)acrylic acid may include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-7100 ^® , M-8030 ^® , M-8060 ^® (East Asian Synthesis) Chemical Co., Ltd.; KAYARAD TMPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Chemical Co., Ltd.); V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Yuki Kayaku Kogyo Co. Ltd.) and so on. These may be used singly or in the form of a mixture of two or more.

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

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

The photopolymerization initiator is an initiator commonly used for a photosensitive resin composition, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, and an anthraquinone-based compound. Or a combination thereof.

Examples of the acetophenone-based compound may be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, and a third butyl group. Trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-( 4-(methylthio)phenyl)-2-morpholinylpropan-1-one, 2-benzyl-2-ethylamino-1-(4-morpholinylphenyl)-butyl- 1-ketone and so on.

Examples of the benzophenone-based compound may be benzophenone, benzhydryl benzoate, benzhydryl methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated Benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylamino Benzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.

Examples of the thioxanthone-based compound may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-chlorothioxanthone and the like.

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-based 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-double (trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-three Pyrazine, 2-(naphthol 1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthol-1-yl)-4,6-bis ( Trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperidinyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4- Methoxystyryl)-s-triazine and the like.

An example of the lanthanoid compound may be an O-indenyl lanthanide compound, 2-(o-benzylidene fluorenyl)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1 -(o-ethylhydrazinyl)-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]ethanone, O-ethoxycarbonyl- Α-oxyamino-1-phenylpropan-1-one and the like. A specific example of the O-mercapto lanthanide compound may be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4- -Phenyl)-butan-1-one, 1-(4-phenylthiophenyl)-butane-1,2-dione 2-indole-O-benzoate, 1-(4-benzene Thiophenyl)-octane-1,2-dione 2-indole-O-benzoate, 1-(4-phenylthiophenyl)-oct-1-one oxime-O-acetate And 1-(4-phenylthiophenyl)-butan-1-one oxime-O-acetate and the like.

The photopolymerization initiator may further contain an oxazole compound, a diketone compound, a lanthanum borate compound, a diazo compound, an imidazole compound, a biimidazole compound or the like in addition to the above compound.

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

Examples of the sensitizer may be tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-mercaptopropionate, dipentaerythritol tetrakis-mercaptopropionate or the like.

The photopolymerization initiator may be contained in an amount of 0.01% by weight to 10% by weight, for example, 0.1% by weight to 5% by weight based on the total amount of the photosensitive resin composition. When the photopolymerization initiator in the range is included, excellent reliability can be ensured due to sufficient curing during exposure of the pattern forming process, and the pattern can have excellent resolution and close contact characteristics as well as excellent heat resistance. It is resistant to light, chemical resistance, and can prevent deterioration of light transmittance due to non-reactive starter.

The solvent is a material having compatibility with, but not reacting with, the compound, the alkali-soluble resin, the photopolymerizable compound, and the photopolymerization initiator.

Examples of the solvent may include an alcohol such as methanol, ethanol, or the like; an ether such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran or the like; a glycol ether such as ethylene glycol monomethyl Ether, ethylene glycol monoethyl ether, etc.; ethylene glycol ethyl acetate, such as methyl glycol acetate diethyl ether, ethyl glycol ethyl acetate diethyl ether, diethyl glycol acetate ethyl ether, etc.; carbitol, such as a Ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether Etc.; propylene glycol alkyl ether acetate, such as propylene glycol monomethyl 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-propyl ketone, methyl n-butyl ketone, methyl n-amyl ketone, 2-heptanone, etc.; saturated aliphatic monocarboxylate a base ester such as ethyl acetate, n-butyl acetate, isobutyl acetate or the like; a lactate such as methyl lactate, ethyl lactate or the like; an alkyl oxyacetate , such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, etc.; alkyl alkoxyacetate, such as methyl methoxyacetate, ethyl methoxyacetate, methoxyacetate Ester, methyl ethoxyacetate, ethyl ethoxyacetate, etc.; alkyl 3-oxopropionate, such as methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.; - alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate Etc.; alkyl 2-oxopropionate, such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; 2-alkoxypropionic acid Alkyl esters, such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxygen Benzyl-2-methylpropionate, such as methyl 2-oxy-2-methylpropanoate, ethyl 2-oxy-2-methylpropionate, etc.; monooxyl monocarboxylic acid alkyl ester Alkyl 2-alkoxy-2-methylpropanoate, such as methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, and the like; Ester, such as 2-hydroxypropionate Propionate, ethyl 2-hydroxy-2-methyl acetate, hydroxyethyl acrylate, methyl methacrylate 2-hydroxy-butyric acid and the like; ketones esters, such as ethyl pyruvate and the like. In addition, high boiling solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformamide, N-methylacetamide, N,N-di can also be used. Methylacetamide, N-methylpyrrolidone, dimethyl hydrazine, benzyl ethyl ether, dihexyl ether, acetamidine, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1 - decyl alcohol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, B Glycol phenyl ether acetate and the like.

In view of miscibility and reactivity, a glycol ether such as ethylene glycol monoethyl ether or the like; ethylene glycol alkyl ether acetate such as ethyl glycol acetate ethyl ether or the like; ester such as 2-hydroxyethyl propionate, etc.; carbitol, such as diethylene glycol monomethyl ether, etc.; and propylene glycol alkyl ether acetate, such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate and many more.

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

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

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

The photosensitive resin composition may further contain a decane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, and the like to improve adhesion to a substrate.

Examples of the decane coupling agent include trimethoxydecyl benzoic acid, γ-methyl propylene oxy propyl trimethoxy decane, vinyl triethoxy decane, vinyl trimethoxy decane, γ-isocyanate propyl Triethoxy decane, γ-glycidoxypropyltrimethoxydecane, β-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, and the like. These may be used singly or in the form of a mixture of two or more.

The decane coupling agent may be contained in an amount of from 0.01 part by weight to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the decane coupling agent in the above range is contained, the close contact characteristics, the storage characteristics, and the like can be improved.

The photosensitive resin composition may further contain a surfactant to improve coating characteristics and suppress speckle generation.

Examples of surfactants may include lanthanide surfactants such as BM-1000 ^® and BM-1100 ^® (BM Chemie Inc.); MEGAFACE F 142D ^® , F 172 ^® , F 173 ^® and F 183 ^® (Dainippon Ink Kagaku Kogyo Co., Ltd.); FULORAD FC-135 ^® , FULORAD FC-170C ^® , FULORAD FC-430 ^® and FULORAD FC-431 ^® (Sumitomo 3M Co., Ltd. ( 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 ^® analogues (Toray Silicone Co., Ltd.) .

The surfactant may be contained in an amount of from 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant in the range is included, coating uniformity is ensured, stains are not generated, and the wetting characteristics of the glass substrate are improved.

The photosensitive resin composition may further contain a predetermined amount of other additives such as an antioxidant, a stabilizer, and the like when it is reduced in characteristics.

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

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

The process comprises applying a positive photosensitive resin composition to a support substrate by spin coating, slit coating, inkjet printing, or the like; drying the coated positive photosensitive resin composition to form a photosensitive The resin composition film is exposed; the positive photosensitive resin composition film is exposed; the exposed positive photosensitive resin composition film is developed in an alkaline aqueous solution to obtain a photosensitive resin film; and the photosensitive resin film is heat-treated. The conditions used in the patterning process are well known in the relevant art and will not be described in detail in this specification.

Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the following examples and comparative examples are provided for the purpose of description and the invention is not limited thereto. (Compound Synthesis) Synthesis Example 1: Synthesis of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.201 g), K ₂ CO ₃ (3.898 g) Acetonitrile (50 ml) was placed in a 100 ml flask and then heated and refluxed. When the reaction was completed, the resultant was filtered and washed with tetrahydrofuran and then concentrated to give a solid. Herein, the solid obtained is washed several times with hexane, filtered and dried in vacuo to give 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile. Synthesis Example 2: Synthesis of 3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy)-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dimethoxyphenol (7.21 g), K ₂ CO ₃ (3.898 g) and N,N-dimethyl Baseamfamide (50 ml) was placed in a 100 ml flask and then heated and stirred at 70 °C. When the reaction was completed, the resultant was extracted with ethyl acetate (EtOAc). After extraction, the resultant was concentrated and purified by column chromatography, then concentrated and dried in vacuo to give 3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy)- benzene. Dimethoxynitrile. Synthesis Example 3: Synthesis of 4-(2-t-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-tert-butylphenol (6.64 g), K ₂ CO ₃ (3.898 g) and acetonitrile (50 ml) were placed at 100 In a ml flask and then heated and refluxed. When the reaction was completed, the resultant was extracted with EA (ethyl acetate). After extraction, the resultant was concentrated and purified by column chromatography, then concentrated and dried in vacuo to give 4-(2-t-butyl-phenoxy)-3,5,6-trichloro-phthalic acid. Nitrile. Synthesis Example 4: Synthesis of 4-(4-t-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 4-tert-butylphenol (6.64 g), K ₂ CO ₃ (3.898 g) and acetonitrile (50 ml) were placed at 100 In a ml flask and then heated and refluxed. When the reaction was completed, the resultant was extracted with EA (ethyl acetate). After extraction, the resultant was concentrated, purified by column chromatography, and then concentrated and dried in vacuo to give 4-(4-t-butyl-phenoxy)-3,5,6-trichloro-o-phenylene. Formonitrile. Synthesis Example 5: Synthesis of 3,4,6-trichloro-5-(3-methyl-butoxy)-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), isoamyl alcohol (5.9 g), 1,8-diazabicycloundec-7-ene (3.898 g) and acetonitrile (50 ml) was placed in a 100 ml flask and then heated and refluxed. When the reaction was completed, the resultant was extracted with EA (ethyl acetate). After extraction, the obtained product was concentrated and purified by column chromatography, then concentrated and dried in vacuo to give 3,4,6-trichloro-5-(3-methyl-butoxy)-phthalic acid. Nitrile. Synthesis Example 6: Synthesis of 3,4,6-trichloro-5-(4-methoxy-phenoxy)-phthalonitrile

Place 3,4,5,6-tetrachlorophthalonitrile (5 g), 4-methoxyphenol (3.201 g), K ₂ CO ₃ (6.64 g) and acetonitrile (50 ml) in 100 ml The flask was then heated and refluxed. When the reaction was completed, the resultant was extracted with EA (ethyl acetate). After extraction, the obtained product was concentrated and purified by column chromatography, followed by concentration and dried in vacuo to give 3,4,6-trichloro-5-(4-methoxy-phenoxy)-phthalic acid. Formonitrile. Synthesis Example 7: Synthesis of a compound represented by Chemical Formula 8

4-(Biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1.0 g) of Synthesis Example 1, 3,4,6-trichloro of Synthesis Example 2 5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.32 g), 1,8-diazabicycloundec-7-ene (0.38 g), 1-pentyl Enol (7 g) and zinc acetate (0.15 g) were placed in a 100 mL flask and heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid from the purification was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 8. [Chemical Formula 8] Maldi-tof MS: 1647.95 m/z Synthesis Example 8: Synthesis of a compound represented by Chemical Formula 9

4-(Biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1.0 g) of Synthesis Example 1, 3,4,6-trichloro of Synthesis Example 2 5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.96 g), 1,8-diazabicycloundec-7-ene (0.58 g), 1-pentyl Enol (14 g) and zinc acetate (0.23 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 9. [Chemical Formula 9] Maldi-tof MS: 1631.91 m/z Synthesis Example 9: Synthesis of a compound represented by Chemical Formula 10

Synthesis of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (0.5 g) of Example 1, 3,4,6-trichloro of Synthesis Example 2 5-(2,6-Dimethoxy-phenoxy)-phthalonitrile (1.44 g), 1,8-diazabicycloundec-7-ene (0.58 g), 1-pentyl Enol (14 g) and zinc acetate (0.23 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 10. [Chemical Formula 10] Maldi-tof MS: 1615.86 m/z Synthesis Example 10: Synthesis of a compound represented by Chemical Formula 11

Synthesis of 4-(4-t-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g) of Example 4, Synthesis 3, 4, 6-III of Example 2. Chloro-5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.33 g), 1,8-diazabicycloundec-7-ene (0.41 g), 1 Pentenol (14 g) and zinc acetate (0.16 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 11. [Chemical Formula 11] Maldi-tof MS: 1587.98 m/z Synthesis Example 11: Synthesis of a compound represented by Chemical Formula 12

Synthesis of 3,4,6-trichloro-5-(3-methyl-butoxy)-phthalonitrile (1 g) of Example 5, Synthesis of 3,4,6-trichloro- of Example 2. 5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.40 g), 1,8-diazabicycloundec-7-ene (0.48 g), 1-pentyl Enol (14 g) and zinc acetate (0.19 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 12. [Chemical Formula 12] Maldi-tof MS: 1401.77 m/z Synthesis Example 12: Synthesis of a compound represented by Chemical Formula 13

Synthesis of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1 g) of Example 1, Synthesis of 3,4,6-trichloro- of Example 5 5-(3-methyl-butoxy)-phthalonitrile (0.4 g), 3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy) of Synthesis Example 2. - phthalonitrile (0.48 g), 1,8-diazabicycloundec-7-ene (0.58 g), 1-pentenol (14 g) and zinc acetate (0.22 g) It was placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 13. [Chemical Formula 13] Maldi-tof MS: 1565.89 m/z Synthesis Example 13: Synthesis of a compound represented by Chemical Formula 14

Synthesis of Example 2 of 3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy)-phthalonitrile (1 g), 1,8-diazabicyclo ring Eleven-7-ene (0.30 g), 1-pentenol (7 g) and zinc acetate (0.12 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 14. [Chemical Formula 14] Maldi-tof MS: 1599.82 m/z Synthesis Example 14: Synthesis of a compound represented by Chemical Formula 15

3,4,6-Trichloro-5-(4-methoxy-phenoxy)-phthalonitrile (1 g) of Synthesis Example 6, 3,4,6-trichloro of Synthesis Example 2 -5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.50 g), 1,8-diazabicycloundec-7-ene (0.65 g), 1- Pentenol (14 g) and zinc acetate (0.26 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 15. [Chemical Formula 15] Maldi-tof MS: 1509.74 m/z Synthesis Example 15: Synthesis of a compound represented by Chemical Formula 16

Synthesis of Example 3 of 4-(2-t-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g), Synthesis Example 2 of 3,4,6-three Chloro-5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.33 g), 1,8-diazabicycloundec-7-ene (0.41 g), 1 Pentenol (14 g) and zinc acetate (0.16 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 16. [Chemical Formula 16] Maldi-tof MS: 1587.98 m/z Comparative Synthesis Example 1: Synthesis of a compound represented by Chemical Formula 17

4-(2-Seconobutyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g), 1,8-diazabicycloundec-7-ene ( 0.30 g), 1-pentenol (7 g) and zinc acetate (0.12 g) were placed in a 100 mL flask and then heated and stirred at 140 °C. When the reaction was completed, the resultant was concentrated and then purified by column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain a compound represented by Chemical Formula 17. [Chemical Formula 17] Maldi-tof MS: 1584.04 m/z (synthetic photosensitive resin composition) Example 1

The photosensitive resin composition according to Example 1 was prepared by mixing the components of the composition given in Table 1 below.

Specifically, the photopolymerization initiator was dissolved in a solvent, stirred at room temperature for 2 hours, an alkali-soluble resin and a photopolymerizable compound were added thereto, and the mixture was stirred at room temperature for 2 hours. Subsequently, a compound according to Synthesis Example 7 (indicated by Chemical Formula 8) and a pigment (in the form of a pigment dispersion) were added as a colorant to the reactant, and the mixture was stirred at room temperature for one hour. Next, the product therein was filtered three times to remove impurities, and a photosensitive resin composition was prepared. [Table 1] (Unit: % by weight) Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 8 (represented by Chemical Formula 9) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 9 (represented by Chemical Formula 10) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 10 (represented by Chemical Formula 11) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 5

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 11 (represented by Chemical Formula 12) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 6

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 12 (represented by Chemical Formula 13) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 7

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 13 (represented by Chemical Formula 14) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 8

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 14 (represented by Chemical Formula 15) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Example 9

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 15 (represented by Chemical Formula 16) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Comparative example 1

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Comparative Synthesis Example 1 (represented by Chemical Formula 17) was used instead of the compound of Synthesis Example 7 (represented by Chemical Formula 8). Comparative example 2

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the components of the composition provided in Table 2 were mixed instead of the composition in Table 1. [Table 2] (Unit: % by weight) Comparative example 3

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

Each of the photosensitive resin compositions according to Examples 1 to 9 and Comparative Examples 1 to 3 was coated on a 1 mm thick degreased glass substrate to a thickness of 1 μm to 3 μm and dried on a hot plate at 90 ° C. 2 Minutes, the membrane was obtained. Subsequently, the film was exposed by using a high pressure mercury lamp having a dominant wavelength of 365 nm. Next, the film was dried in a forced convection drying oven at 200 ° C for 5 minutes to obtain a sample. The pixel layer was measured for the color coordinates (x, y), the luminance Y, and the contrast ratio by using a spectrophotometer (MCPD3000, Otsuka Electronics Inc.), and the results are shown in Table 3. [table 3]

Referring to Table 3, the photosensitive resin compositions of Examples 1 to 9 containing the compound according to one example as a dye showed excellent color characteristics as compared with the photosensitive resin compositions according to Comparative Examples 1 to 3.

Although the present invention has been described in connection with the exemplary embodiments of the present invention, it is understood that the invention is not limited to the disclosed embodiments Various modifications and equivalent configurations.

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no.

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Claims (16)

A compound represented by Chemical Formula 1: [Chemical Formula 1] Wherein in Chemical Formula 1, M is Cu, Zn, Co or Mo, and R ¹ to R ^{16 are} independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 alkoxy group, a substituted or unsubstituted C6-C20 aryl or a substituted or unsubstituted C6-C20 aryloxy group, and R ¹ to R ^{16 is} at least one represented by chemical formula 2, [Chemical Formula 2] Wherein in Chemical Formula 2, R ¹⁷ and R ^{18 are} independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group. A compound represented by Chemical Formula 1 as described in claim 1, wherein Chemical Formula 2 is represented by Chemical Formula 3: [Chemical Formula 3] Wherein in Chemical Formula 3, R ¹⁷ and R ^{18 are} independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group. A compound represented by Chemical Formula 1 according to the first aspect of the invention, wherein R ¹ to R ^{16 are} represented by Chemical Formula 2, and at least one of R ¹ to R ^{16 is} represented by one of Chemical Formula 4 to Chemical Formula 7 : [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] Wherein in Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. The compound represented by Chemical Formula 1 according to the first aspect of the invention, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ is from Chemical Formula 4 to Chemical Formula 7 One of them is that at least one of R ⁹ to R ^{12 is} represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ¹³ to R ^{16 is} represented by one of Chemical Formula 4 to Chemical Formula 7: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] Wherein in Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. The compound represented by Chemical Formula 1 according to the first aspect of the invention, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, and R At least one of ⁹ to R ^{12 is} represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ¹³ to R ^{16 is} represented by one of Chemical Formula 4 to Chemical Formula 7: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] Wherein in Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. The compound represented by Chemical Formula 1 according to the first aspect of the invention, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ is from Chemical Formula 4 to Chemical Formula 7 One of them is 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 one of Chemical Formula 4 to Chemical Formula 7: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] Wherein in Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. A compound represented by Chemical Formula 1 according to Claim 1, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, R ⁹ At least one of to R ¹² is represented by Chemical Formula 2, and at least one of R ¹³ to R ^{16 is} represented by one of Chemical Formula 4 to Chemical Formula 7: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] Wherein in Chemical Formula 6 and Chemical Formula 7, L ¹ is a substituted or unsubstituted C1 to C10 alkylene group, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. A compound represented by Chemical Formula 1 according to Claim 1, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, and at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, R ⁹ At least one of 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 represented by Chemical Formula 1 according to the first aspect of the invention, wherein the compound represented by Chemical Formula 1 is represented by one of Chemical Formula 8 to Chemical Formula: [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] . The compound represented by Chemical Formula 1 according to the first aspect of the invention, wherein the compound represented by Chemical Formula 1 is a green dye. The compound represented by Chemical Formula 1 as described in claim 10, wherein the green dye has a maximum light transmittance in a wavelength of 445 nm to 560 nm. A photosensitive resin composition comprising the compound represented by Chemical Formula 1 according to any one of Claim No. 1 to Claim No. 11. The photosensitive resin composition according to claim 12, 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 claim 13, wherein the photosensitive resin composition further comprises a pigment. The photosensitive resin composition according to claim 14, wherein the pigment is a yellow pigment. A color filter produced by using the photosensitive resin composition as described in claim 12 of the patent application.