CN107428766A - Compounds, photosensitive resin composition and colored filter containing it - Google Patents

Abstract

The present invention provides a compound represented by a specific chemical formula, a photosensitive resin composition containing the compound, and a color filter manufactured using the photosensitive resin composition.

Description

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

technical field

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

Background technique

A color filter manufactured by using a pigment-type photosensitive resin composition has limitations in brightness and contrast ratio due to the particle size of the pigment. In addition, imaging sensor devices require smaller dispersed particle sizes to form fine patterns. In order to meet the demand, attempts have been made to realize color filters with improved color characteristics such as brightness, contrast ratio, etc. by manufacturing photosensitive resin compositions by introducing non-particle-forming dyes instead of pigments.

Therefore, it is necessary to study an appropriate compound to be used as a dye for producing a photosensitive resin composition.

Contents of the invention

[Technical Direction]

One embodiment provides a novel compound.

Another embodiment provides a photosensitive resin composition comprising the compound.

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

[Technical solution]

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,

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 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, and

At least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2,

[chemical formula 2]

Wherein, in chemical formula 2,

R ¹⁷ and R ¹⁸ are independently substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl.

Chemical Formula 2 may be represented by Chemical Formula 3.

[chemical formula 3]

In Chemical Formula 3,

R ¹⁷ and R ¹⁸ are independently substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl.

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 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 can be represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ can be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ⁹ to R ¹² can be represented by Chemical Formula 4 to one of 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.

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 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 can be represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ can be represented by one of Chemical Formula 4 to Chemical Formula 7, and at least one of R ⁹ to R ¹² can 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.

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 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, 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.

The compound represented by Chemical Formula 1 may 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 may have maximum light transmittance in a wavelength of 445nm to 560nm.

Another embodiment provides a photosensitive resin composition comprising the compound.

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 be a yellow pigment.

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

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

[Beneficial effect]

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

detailed description

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

As used herein, when no specific definition is otherwise provided, the term "substituted" means substituted with a substituent selected from: halogen (F, Br, Cl or I), hydroxyl, 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 C1 to C10 alkyl), formamidino, hydrazino , hydrazone, carboxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic group, Substituted or unsubstituted aryl groups and substituted or unsubstituted heterocyclic groups replace the functional groups of the present invention.

As used herein, when no specific definition is otherwise provided, the term "alkyl" refers to C1 to C20 alkyl and specifically C1 to C15 alkyl, and the term "cycloalkyl" refers to C3 to C20 cycloalkyl and specifically For C3 to C18 cycloalkyl, the term "alkoxy" refers to C1 to C20 alkoxy and specifically C1 to C18 alkoxy, and the term "aryl" refers to C6 to C20 aryl and specifically C6 to C18 aryl, the term "alkenyl" refers to C2 to C20 alkenyl and specifically C2 to C18 alkenyl, the term "alkylene" refers to C1 to C20 alkylene and specifically C1 to C18 alkylene Alkyl, and the term "arylene" refers to a C6 to C20 arylene group and specifically a C6 to C16 arylene group.

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

As used herein, when no definition is provided otherwise, the term "combining" means mixing or copolymerizing. In addition, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

In the chemical formulas in this specification, unless a specific definition is provided otherwise, when a chemical bond is not shown where it should be given, hydrogen is bonded at the said position.

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

One embodiment provides a compound represented by Chemical Formula 1.

[chemical formula 1]

In Chemical Formula 1,

M is Cu, Zn, Co or Mo,

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 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, and

At least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2,

[chemical formula 2]

Wherein, in chemical formula 2,

R ¹⁷ and R ¹⁸ are independently substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl.

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

In an exemplary embodiment, M may be Zn.

Chemical Formula 2 may be represented by Chemical Formula 3.

[chemical formula 3]

In Chemical Formula 3,

R ¹⁷ and R ¹⁸ are independently substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl.

The compound represented by Chemical Formula 1 according to one embodiment must contain a substituent represented by Chemical Formula 2, such as Chemical Formula 3 and cause a red shift, so compared with a composition containing a pigment such as a green pigment, the compound represented by Chemical Formula according to one embodiment The compound represented by 1 exhibited excellent brightness.

In addition, the compound represented by Chemical Formula 1 according to one embodiment must contain a substituent represented by Chemical Formula 2, such as Chemical Formula 3, and shows greatly improved solubility in organic solvents, while the phthalocyanine dye compound containing an amide substituent in Solubility in organic solvents deteriorates sharply.

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 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 can be substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted propylene, substituted or unsubstituted butylene , substituted or unsubstituted pentylene, substituted or unsubstituted hexylene, substituted or unsubstituted heptylene, substituted or unsubstituted octylene, substituted or unsubstituted Nonylene or substituted or unsubstituted decylene.

The compound according to one embodiment further includes a substituent represented by one of Chemical Formula 4 to Chemical Formula 7 in addition to the substituent represented by Chemical Formula 2 and may increase solubility in an organic solvent and improve coloring properties.

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 one of Chemical Formula 4 to Chemical Formula 7, at least one of R ⁹ to R ¹² or 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 , R1 to R4 may be represented by Chemical Formula ² , at least one of R5 to ^R8 may be represented by Chemical Formula ² , at least one of ^R9 to ^R12 may be represented by Chemical Formula 4 to Chemical Formula 7 One of them is represented, and at least one of ^R13 to ^R16 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 one of Chemical Formula 4 to Chemical Formula 7, at least one of R ⁹ to R ¹² or 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 , R1 to R4 may be represented by Chemical Formula ² , at least one of R5 to ^R8 may be represented by Chemical Formula ² , at least one of ^R9 to ^R12 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 , R1 to R4 may be represented by Chemical Formula ² , at least one of R5 to ^R8 may be represented by Chemical Formula ² , at least one of ^R9 to ^R12 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 even in a smaller amount due to the substituent represented by Chemical Formula 2, for example, Chemical Formula 3, it is possible to manufacture a colorant having excellent color characteristics by using the compound as a colorant. A display device such as a display device having excellent brightness, contrast ratio, and the like. For example, the compound may be a colorant, such as a dye, such as a green dye which may have, for example, a maximum transmittance 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, more expensive dyes may need to be used to achieve desired effects such as high brightness, high contrast ratio, etc. and thus increase unit production costs. However, when the compound according to one embodiment is used as a dye of a color filter, the compound can realize excellent color characteristics such as high brightness, high contrast ratio, etc. even when used in a small amount, and reduce unit production cost.

In addition, the compound according to one embodiment may include a substituent represented by one of Chemical Formula 4 to Chemical Formula 7 in addition to the substituent represented by Chemical Formula 2, such as Chemical Formula 3, and thus may show improved Solubility and improved coloring properties.

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

For example, a photosensitive resin composition includes the compound according to the above-mentioned embodiments, 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 green dye) in a photosensitive resin composition and can realize excellent color characteristics.

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

The photosensitive resin composition may further include pigments, such as yellow pigments.

The yellow pigments may be C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment Yellow 150, etc. in Color Index, and these pigments may be used alone or as 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 liquid may contain 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 contain 1% by weight to 20% by weight, such as 8% by weight to 20% by weight, such as 8% by weight to 15% by weight, such as 10% by weight to 20% by weight and such as 10% by weight Solid pigment in an amount of up to 15% by weight.

The dispersant may be a nonionic dispersant, anionic dispersant, cationic dispersant, or the like. Specific examples of the dispersant may be polyalkylene glycol and its ester, polyoxyalkylene, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonate, sulfonate, carboxylate, carboxylate acid salts, alkylamide alkylene oxide addition products, alkylamines, etc., and may be used alone or in admixture of two or more.

Commercially available examples of the dispersant may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, manufactured by BYK Co., Ltd. DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc.; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA- 100, EFKA-400, EFKA-450, etc.; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 2800, etc. manufactured by Zenica Corporation; PB711, PB821, etc. manufactured by Zhisu Company.

The dispersant may be included in an amount of 1% by weight to 20% by weight based on the total amount of the pigment dispersion liquid. When the dispersant within the range is included, the dispersion liquid of the photosensitive resin composition can be improved due to proper viscosity, and thus the optical, physicochemical quality of the product can be maintained.

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

Based on the total amount of the photosensitive resin composition, the pigment dispersion liquid may be contained in an amount of 10% by weight to 20% by weight, for example, 12% by weight to 18% by weight. When the pigment dispersion liquid within the range is included, process margin is advantageously secured and color reproducibility and 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 comprising at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group. Examples of the monomer include (meth)acrylic acid, maleic acid, itaconic acid, fumaric acid, or combinations 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 acrylic resin.

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

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 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 alone or in admixture of two or more.

The weight average molecular weight of the alkali-soluble resin may be 3,000 g/mol to 150,000 g/mol, such as 5,000 g/mol to 50,000 g/mol, and further such as 20,000 g/mol to 30,000 g/mol. When the weight-average molecular weight of the acrylic resin is within the range, the photosensitive resin composition for color filters has good physical and chemical properties, proper viscosity, and close contact with substrates during color filter manufacturing characteristic.

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

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

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

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

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 Acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di( Meth)acrylate, Pentaerythritol Di(meth)acrylate, Pentaerythritol Tri(meth)acrylate, Pentaerythritol Tetra(meth)acrylate, Pentaerythritol Hexa(meth)acrylate, Dipentaerythritol Di(meth)acrylate Dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy (meth)acrylate, ethylene glycol monomethacrylate Ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tri(meth)acryloyloxyethyl phosphate, novolak epoxy (meth)acrylate, etc.

Commercially available examples of photopolymerizable compounds are as follows. Examples of monofunctional (meth)acrylates may include Aronix M- M- M- (Toa Gosei Chemical Co., Ltd.); KAYARAD TC- TC- (Nippon Kayaku Co., Ltd.); V- V- (Osaka Organic Chemical Co., Ltd.) and so on. Examples of difunctional (meth)acrylates may include Aronix M- M- M- (Toa Gosei Chemical Co., Ltd.); KAYARAD HX- R- (Nippon Kayaku Co., Ltd.); V- V- V-335 (Osaka Organic Chemical Co., Ltd.) and so on. Examples of trifunctional (meth)acrylates may include Aronix M- M- M- M- M- M- M- (Toa Gosei Chemical Co., Ltd.); KAYARAD DPCA- DPCA- DPCA- DPCA- (Nippon Kayaku Co., Ltd.); V- V- V- V- V- V- (Osaka Organic Chemical Co., Ltd.) and so on. These may be used alone or in admixture of two or more.

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

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

The photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, such as acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, oxime-based compounds or combinations thereof.

Examples of acetophenone-based compounds can be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyl Base trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-( 4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan- 1-keto and more.

Examples of benzophenone-based compounds may be benzophenone, benzoyl benzoate, benzoyl methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzphenone Ketone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminodiphenyl Methanone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone and the like.

Examples of thioxanthone-based compounds 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 triazine compounds 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 Azine, 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-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4- Methoxystyryl)-s-triazine and the like.

Examples of oxime compounds can be O-acyl oxime compounds, 2-(o-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-( o-acetyl oxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxy Amino-1-phenylpropan-1-one and the like. Specific examples of O-acyl oxime compounds can be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl -phenyl)-butan-1-one, 1-(4-phenylthiophenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylthio phenyl)-octane-1,2-dione 2-oxime-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 contain carbazole-based compounds, diketone-based compounds, sulfonium borate-based compounds, diazo-based compounds, imidazole-based compounds, biimidazole-based compounds, and the like in addition to the compounds.

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 tetra-3-mercaptopropionate, dipentaerythritol tetra-3-mercaptopropionate, and 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 is contained within the range, excellent reliability can be ensured due to sufficient curing during exposure in the pattern forming process, and the pattern can have excellent resolution and close contact characteristics as well as excellent durability. Heat resistance, light resistance and chemical resistance, and can prevent deterioration of light transmittance due to non-reaction initiator.

The solvent is a material that has compatibility with, but does not react with, the compound, alkali-soluble resin, photopolymerizable compound, and photopolymerization initiator.

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.; ethyl glycol acetate, such as methyl glycol acetate, ethyl glycol acetate, diethyl glycol acetate, etc.; carbitol, such as methyl 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 acetates, 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 monocarboxylic acid alkanes Alkyl esters, such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactate esters, such as methyl lactate, ethyl lactate, etc.; alkyl oxyacetates, such as methyl oxyacetate, oxygen ethyl oxyacetate, butyl oxyacetate, etc.; alkyl alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, Ethyl ethoxyacetate, etc.; Alkyl 3-oxypropionate, such as methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.; Alkyl 3-alkoxypropionate , such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; 2-oxypropionate Alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; alkyl 2-alkoxypropionates such as 2-methoxy Methyl propionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxy-2-methylpropionate , such as methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, etc.; 2-alkoxy-2- Alkyl methylpropionates, such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.; esters, such as 2-hydroxyethyl propionate esters, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate, 2-hydroxy-3-methylmethyl butyrate, etc.; ketoesters, such as ethyl pyruvate, etc. In addition, high boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, Amide, N-Methylpyrrolidone, Dimethylsulfoxide, Benzylethyl Ether, Dihexyl Ether, Acetylacetone, Isophorone, Caproic Acid, Caprylic Acid, 1-Octanol, 1-Nonanol, Benzene Methanol, Benzyl Acetate, Ethyl Benzoate, Diethyl Oxalate, Diethyl Maleate, Gamma-Butyrolactone, Ethylene Carbonate, Propylene Carbonate, Ethylene Glycol Phenyl Ether Acetate and more.

In consideration of miscibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether and the like; glycol alkyl ether acetates such as ethyl glycol ethyl acetate and the like; esters such as 2-hydroxyethyl propionate, etc.; carbitol, such as diethylene glycol monomethyl ether, etc.; and propylene glycol alkyl ether acetates, such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate wait.

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

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

Examples of epoxy compounds may be phenol novolac epoxy compounds, tetramethylbiphenyl epoxy compounds, bisphenol A epoxy compounds, alicyclic epoxy compounds, or combinations thereof.

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

The photosensitive resin composition may further include a silane coupling agent having reactive substituents such as carboxyl, methacryloyl, isocyanate, epoxy, and the like to improve adhesion to the substrate.

Examples of silane coupling agents include trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatepropyltrimethoxysilane, Ethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like. These may be used alone or in admixture of two or more.

Based on 100 parts by weight of the photosensitive resin composition, the silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight. When the silane coupling agent within the above range is contained, close contact properties, storage properties, and the like can be improved.

The photosensitive resin composition may further include a surfactant to improve coating properties and suppress generation of spots.

Examples of surfactants may include terpene-based surfactants, such as BM- and BM- (BM Chemicals); MEGAFACE F f f and F (Dainippon Ink Chemical Co., Ltd.); FULORAD FC- FULORAD FC- FULORAD FC- and FULORAD FC- (Sumitomo 3M Corporation); SURFLON S- SURFLON S- SURFLON S- SURFLON S- and SURFLON S- (Asahi Glass Co., Ltd.); and SH- SH- SH- SZ- and SF- Its analog (Toray Silicone Co., Ltd.).

Based on 100 parts by weight of the photosensitive resin composition, the surfactant may be included in an amount of 0.001 to 5 parts by weight. When the surfactant is contained within the range, coating uniformity may be ensured, no staining may be generated, and the wetting characteristics of the glass substrate may be improved.

The photosensitive resin composition may further contain other additives, such as antioxidants, stabilizers, etc., in predetermined amounts while reducing their properties.

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

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

The process includes coating a positive photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing, etc.; drying the coated positive photosensitive resin composition to form a photosensitive 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 film; and heat-treating the photosensitive resin film. Conditions for the patterning process are well known in the related art and will not be described in detail in this specification.

[embodiment of the invention]

Hereinafter, the present invention is explained in more detail with reference to Examples and Comparative Examples. However, the following examples and comparative examples are provided for description purposes and the present 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 (3,4,5,6-tetrachlorophthalonitrile) (5g), 2-phenylphenol (3.201g), K ₂ CO ₃ (3.898g) and Acetonitrile (50ml) was placed in a 100ml flask and then heated and refluxed. When the reaction was complete, the resultant was filtered and washed with tetrahydrofuran, and then concentrated to obtain a solid. Herein, the obtained solid was washed several times with hexane, filtered and dried under vacuum to obtain 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 (5g), 2,6-dimethoxyphenol (7.21g), K ₂ CO ₃ (3.898g) and N,N-dimethyl Formamide (50ml) was placed in a 100ml flask and then heated and stirred at 70°C. When the reaction was complete, the resultant was extracted with ethyl acetate (EA). After extraction, the resultant was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy)-o-phenyl Dicarbonitrile.

Synthesis Example 3: Synthesis of 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5g), 2-tert-butylphenol (6.64g), K ₂ CO ₃ (3.898g) and acetonitrile (50ml) were placed in a 100ml flask And then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the resultant was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalamide Nitrile.

Synthesis Example 4: Synthesis of 4-(4-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5g), 4-tert-butylphenol (6.64g), K ₂ CO ₃ (3.898g) and acetonitrile (50ml) were placed in a 100ml flask And then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the resultant was concentrated, purified via column chromatography, and then concentrated and dried in vacuo to obtain 4-(4-tert-butyl-phenoxy)-3,5,6-trichloro-phthalic di formyl nitrile.

Synthesis Example 5: Synthesis of 3,4,6-trichloro-5-(3-methyl-butoxy)-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5g), isoamyl alcohol (5.9g), 1,8-diazabicycloundec-7-ene (3.898g) and acetonitrile ( 50ml) was placed in a 100ml flask and then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the obtained resultant was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 3,4,6-trichloro-5-(3-methyl-butoxy)-phthalamide Nitrile.

Synthesis Example 6: Synthesis of 3,4,6-trichloro-5-(4-methoxy-phenoxy)-phthalonitrile

3,4,5,6-tetrachlorophthalonitrile (5 g), 4-methoxyphenol (3.201 g), K ₂ CO ₃ (6.64 g) and acetonitrile (50 ml) were placed in a 100 ml flask and Then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the obtained resultant was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 3,4,6-trichloro-5-(4-methoxy-phenoxy)-phthalic acid formyl nitrile.

Synthesis Example 7: Synthesis of compounds represented by Chemical Formula 8

4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1.0 g) from Synthesis Example 1, 3,4,6-trichloro-phthalonitrile from Synthesis Example 2 5-(2,6-Dimethoxy-phenoxy)-phthalonitrile (0.32g), 1,8-diazabicycloundec-7-ene (0.38g), 1-penta 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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid from purification was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 8.

[chemical formula 8]

Maldi-tof MS: 1647.95m/z

Synthesis Example 8: Synthesis of compounds represented by Chemical Formula 9

4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1.0 g) from Synthesis Example 1, 3,4,6-trichloro-phthalonitrile from Synthesis Example 2 5-(2,6-Dimethoxy-phenoxy)-phthalonitrile (0.96g), 1,8-diazabicycloundec-7-ene (0.58g), 1-penta 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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 9.

[chemical formula 9]

Maldi-tof MS: 1631.91m/z

Synthesis Example 9: Synthesis of compounds represented by Chemical Formula 10

4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (0.5 g) of Synthetic Example 1, 3,4,6-trichloro-phthalonitrile of Synthetic Example 2 5-(2,6-Dimethoxy-phenoxy)-phthalonitrile (1.44g), 1,8-diazabicycloundec-7-ene (0.58g), 1-penta 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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 10.

[chemical formula 10]

Maldi-tof MS: 1615.86m/z

Synthesis Example 10: Synthesis of compounds represented by Chemical Formula 11

4-(4-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g) from Synthesis Example 4, 3,4,6-trichloro-phthalonitrile from Synthesis Example 2 -5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.33g), 1,8-diazabicycloundec-7-ene (0.41g), 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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 11.

[chemical formula 11]

Maldi-tof MS: 1587.98m/z

Synthesis Example 11: Synthesis of compounds represented by Chemical Formula 12

3,4,6-trichloro-5-(3-methyl-butoxy)-phthalonitrile (1 g) of Synthetic Example 5, 3,4,6-trichloro-5 of Synthetic Example 2 -(2,6-Dimethoxy-phenoxy)-phthalonitrile (0.40g), 1,8-diazabicycloundec-7-ene (0.48g), 1-pentene Alcohol (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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 12.

[chemical formula 12]

Maldi-tof MS: 1401.77m/z

Synthesis Example 12: Synthesis of compounds represented by Chemical Formula 13

4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile (1 g) of Synthetic Example 1, 3,4,6-trichloro-5 of Synthetic Example 5 -(3-Methyl-butoxy)-phthalonitrile (0.4g), 3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy of Synthetic Example 2 )-phthalonitrile (0.48g), 1,8-diazabicycloundec-7-ene (0.58g), 1-pentenol (14g) and zinc acetate (0.22g) were placed in 100mL flask and then heated and stirred at 140 °C. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 13.

[chemical formula 13]

Maldi-tof MS: 1565.89m/z

Synthesis Example 13: Synthesis of compounds represented by Chemical Formula 14

3,4,6-trichloro-5-(2,6-dimethoxy-phenoxy)-phthalonitrile (1 g), 1,8-diazabicyclodeca Mono-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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 14.

[chemical formula 14]

Maldi-tof MS: 1599.82m/z

Synthesis Example 14: Synthesis of compounds represented by Chemical Formula 15

3,4,6-trichloro-5-(4-methoxy-phenoxy)-phthalonitrile (1 g) of Synthetic Example 6, 3,4,6-trichloro- 5-(2,6-Dimethoxy-phenoxy)-phthalonitrile (0.50g), 1,8-diazabicycloundec-7-ene (0.65g), 1-penta Enol (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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 15.

[chemical formula 15]

Maldi-tof MS: 1509.74m/z

Synthesis Example 15: Synthesis of a compound represented by Chemical Formula 16

4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g) from Synthesis Example 3, 3,4,6-trichloro-phthalonitrile from Synthesis Example 2 -5-(2,6-dimethoxy-phenoxy)-phthalonitrile (0.33g), 1,8-diazabicycloundec-7-ene (0.41g), 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 complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 16.

[chemical formula 16]

Maldi-tof MS: 1587.98m/z

Comparative Synthesis Example 1: Synthesis of a compound represented by Chemical Formula 17

4-(2-Second-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g), 1,8-diazabicyclounde-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 complete, the resultant was concentrated and then purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuo to obtain the compound represented by Chemical Formula 17.

[chemical formula 17]

Maldi-tof MS: 1584.04m/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, a 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, the compound according to Synthesis Example 7 (represented by Chemical Formula 8) and a pigment (in the form of a pigment dispersion liquid) were added to the reactant as a colorant, and the mixture was stirred at room temperature for one hour. Then, the product therein was filtered three times to remove impurities to prepare a photosensitive resin composition.

[Table 1]

(unit 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 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 according to the same method 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 according to the same method 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 according to the same method 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 according to the same method 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 according to the same method 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 according to the same method 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 according to the same method 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 according to the same method 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 according to the same method 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 weight%)

Comparative example 3

A photosensitive resin composition was prepared in the same manner as in Comparative Example 2 except that Pigment G36 pigment dispersion was used instead of Pigment G58 pigment dispersion.

Evaluation: Color Coordinates, Brightness and Contrast Ratio

Each photosensitive wax composition according to Example 1 to Example 9 and Comparative Example 1 to Comparative Example 3 was coated on a 1 mm thick degreased glass substrate to a thickness of 1 μm to 3 μm and dried on a 90° C. hot plate for 2 minutes, Obtain the film. 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 color coordinates (x, y), luminance Y, and contrast ratio by using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are provided in Table 3.

[table 3]

Color coordinates (x, y) Brightness (Y) contrast ratio Example 1 (0.284, 0.576) 63.0 15,700 Example 2 (0.279, 0.576) 62.3 15,300 Example 3 (0.281, 0.576) 62.9 15,100 Example 4 (0.278, 0.576) 62.7 15,800 Example 5 (0.280, 0.576) 63.3 15,600 Example 6 (0.278, 0.576) 63.1 15,500 Example 7 (0.277, 0.576) 62.1 15,900 Example 8 (0.279, 0.576) 62.2 15,700 Example 9 (0.282, 0.576) 62.8 15,800 Comparative example 1 (0.275, 0.575) 60.7 14,800 Comparative example 2 (0.275, 0.577) 61.4 14,400 Comparative example 3 (0.276, 0.577) 59.7 14,100

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

While the invention has been described in connection with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary is intended to cover various aspects included within the spirit and scope of the appended claims. Modifications and equivalent configurations.

Claims (16)

1. A compound, characterized in that, represented by chemical formula 1: [chemical formula 1] Wherein in chemical formula 1, M is Cu, Zn, Co or Mo, 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 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, and At least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2, [chemical formula 2] Wherein in chemical formula 2, R ¹⁷ and R ¹⁸ are independently substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl. 2. The compound according to 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 substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl. 3. The compound according to claim 1, 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 is a substituted or unsubstituted ^C1 to C10 alkylene, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. 4. The compound according to claim 1, wherein, At least one of R ¹ to R ⁴ is represented by Chemical Formula 2, ^At least one of R to R is represented by one of Chemical Formula ⁴ to Chemical Formula 7, At least one of ^R9 to ^R12 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 is a substituted or unsubstituted ^C1 to C10 alkylene, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. 5. The compound according to claim 1, wherein, At least one of R ¹ to R ⁴ is represented by Chemical Formula 2, ^At least one of R to R is represented by Chemical Formula ² , At least one of ^R9 to ^R12 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 is a substituted or unsubstituted ^C1 to C10 alkylene, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. 6. The compound according to claim 1, wherein, At least one of R ¹ to R ⁴ is represented by Chemical Formula 2, ^At least one of R to R is represented by one of Chemical Formula ⁴ to Chemical Formula 7, At least one of ^R9 to ^R12 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 is a substituted or unsubstituted ^C1 to C10 alkylene, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. 7. The compound according to claim 1, wherein, At least one of R ¹ to R ⁴ is represented by Chemical Formula 2, ^At least one of R to R is represented by Chemical Formula ² , At least one of ^R9 to ^R12 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 is a substituted or unsubstituted ^C1 to C10 alkylene, and R ¹⁹ is a substituted or unsubstituted C1 to C10 alkyl group. 8. The compound according to claim 1, wherein, At least one of R ¹ to R ⁴ is represented by Chemical Formula 2, ^At least one of R to R is represented by Chemical Formula ² , At least one of ^R9 to ^R12 is represented by Chemical Formula 2, and At least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2. 9. The compound according to claim 1, wherein the compound is 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] 10. The compound of claim 1, wherein the compound is a green dye. 11. The compound of claim 10, wherein the green dye has a maximum light transmittance at a wavelength of 445nm to 560nm. 12. A photosensitive resin composition, characterized by comprising the compound according to any one of claims 1-11. 13. The photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. 14. The photosensitive resin composition according to claim 13, wherein the photosensitive resin composition further comprises a pigment. 15. The photosensitive resin composition according to claim 14, wherein the pigment is a yellow pigment. 16. A color filter manufactured using the photosensitive resin composition according to claim 12.