KR102149968B1 - Novel compound,photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

(상기 화학식 1에서, 각 치환기는 명세서에 정의된 바와 같다.)A compound represented by the following Formula 1, a photosensitive resin composition including the same, and a color filter prepared using the photosensitive resin composition are provided.
[Formula 1]

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

Description

A novel compound, a photosensitive resin composition and a color filter comprising the same TECHNICAL FIELD [NOVEL COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION COMPRISING THE SAME AND COLOR FILTER}

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

In a color filter made of a pigment-type photosensitive resin composition, there is a limit to the brightness and contrast ratio resulting from the pigment particle size. In addition, in the case of a color image sensor for an image sensor, a smaller dispersion particle size is required to form a fine pattern. In order to meet such demands, attempts to implement a color filter having improved color characteristics such as brightness and contrast ratio by preparing a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment is continued.

Therefore, there is a need for research on a compound suitable as a dye used in the production of a photosensitive resin composition.

One embodiment is to provide a novel compound.

Another embodiment is to provide a photosensitive resin composition comprising the compound.

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

One embodiment of the present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

R ¹ to R ¹⁶ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 To C20 aryloxy group,

However, at least two or more of R ¹ to R ¹⁶ are represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group,

R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.

Formula 2 may be represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group,

R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.

R ¹⁷ may be a tert-butyl group.

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

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

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

Wherein R ¹ to R ⁴ are all halogen atoms, at least one of R ⁵ to R ⁸ is represented by Formula 2, at least one of R ⁹ to R ¹² is represented by Formula 2, and R ¹³ to At least one of R ¹⁶ may be represented by Formula 2.

All of R ¹ to R ⁸ are halogen atoms, at least one of R ⁹ to R ¹² may be represented by Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Formula 2.

R ¹ to R ⁴ are all halogen atoms, at least one of R ⁵ to R ⁸ is represented by Formula 2, and R ⁹ to R ¹² are all halogen atoms, and at least one of R ¹³ to R ¹⁶ May be represented by Formula 2 above.

The compound represented by Formula 1 may be represented by any one of Formulas 4 to 11 below.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

The compound may be a green dye.

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

Another embodiment provides a photosensitive resin composition comprising the compound.

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

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

The photosensitive resin composition may further include a pigment.

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

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

Other specifics of aspects of the present invention are included in the detailed description below.

The compound according to an embodiment has excellent green spectral properties, high molar absorption coefficient, and has excellent solubility in organic solvents, and thus can be used as a dye when preparing a photosensitive resin composition for a green color filter, and the color filter including the dye It can have excellent luminance and contrast ratio.

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

Unless otherwise specified in the specification, "substituted" to "substituted" means that at least one hydrogen atom in the functional groups of the present invention is a halogen atom (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group ( NH ₂ , NH (R ²⁰⁰ ) or N (R ²⁰¹ ) (R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different from each other, and each independently a C1 to C10 alkyl group), an amidino group, A hydrazine group, a hydrazone group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, and It means substituted with one or more substituents selected from the group consisting of substituted or unsubstituted heterocyclic groups.

Unless otherwise specified in the specification, “alkyl group” refers to a C1 to C20 alkyl group, specifically C1 to C15 alkyl group, and “cycloalkyl group” refers to a C3 to C20 cycloalkyl group, specifically C3 To C18 cycloalkyl group, "alkoxy group" refers to a C1 to C20 alkoxy group, specifically C1 to C18 alkoxy group, and "aryl group" refers to a C6 to C20 aryl group, specifically C6 to It means a C18 aryl group, and "alkenyl group" means a C2 to C20 alkenyl group, specifically C2 to C18 alkenyl group, and "alkylene group" means a C1 to C20 alkylene group, specifically C1 To C18 alkylene group, and "arylene group" refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.

Unless otherwise specified in the specification, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" means "acrylic acid" and "methacrylic acid" It means both are possible.

Unless otherwise defined herein, "combination" means mixing or copolymerization. In addition, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

Unless otherwise defined in the chemical formula in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded at the position.

In addition, unless otherwise defined in the specification, "*" means a part connected to the same or different atoms or chemical formulas.

One embodiment provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

R ¹ to R ¹⁶ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 To C20 aryloxy group,

However, at least two or more of R ¹ to R ¹⁶ are represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group,

R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.

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

The compound represented by Formula 1 has excellent green spectral properties and a high molar extinction coefficient. Further, since the compound represented by Formula 1 must contain at least two or more substituents represented by Formula 2, it may exhibit excellent solubility in an organic solvent and excellent brightness and contrast ratio when applied to a color filter.

For example, when the compound represented by Formula 1 contains only one substituent represented by Formula 2, the solubility, brightness and contrast ratio in the organic solvent are largely decreased, and it is difficult to use it as a colorant in the photosensitive resin composition for color filters. There may be.

Formula 2 may be represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group,

R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.

The substituent represented by Formula 3 has 1 alkyl group and 1 alkoxy group, the 1 alkyl group is substituted at the ortho position, and the 1 alkoxy group is substituted at the para position, And the contrast ratio can be further improved. For example, when the one alkyl group is substituted at the para position and the one alkoxy group is substituted at the ortho position, it may be difficult to implement a green pixel for a color filter.

For example, R ¹⁷ may be a tert-butyl group. R ¹⁷ is more advantageous in terms of brightness and contrast ratio in the case of a branch alkyl group such as tert-butyl group than in the case of a linear alkyl group such as a methyl group, an ethyl group, or an n-butyl group.

At least one of R ¹ to R ¹⁶ may be a substituted or unsubstituted C1 to C20 alkoxy group. For example, in Formula 1, "two of R ¹ to R ¹⁶ are represented by the following Formula 2, and at the same time, when at least one of R ¹ to R ¹⁶ is an alkoxy group", "two of R ¹ to R ¹⁶ are It is more advantageous in terms of solubility than the case represented by Chemical Formula 2 and all of the remaining substituents are halogen atoms.

Further, in Formula 1, when "four or more of R ¹ to R ¹⁶ are represented by the following Formula 2" (eg, at least one of R ¹ to R ⁴ is represented by Formula 2, and the R ⁵ to R ^When at least one of ⁸ is represented by Formula 2, at least one of R ⁹ to R ¹² is represented by Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Formula 2), the most excellent It can have solubility.

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

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

Wherein R ¹ to R ⁴ are all halogen atoms, at least one of R ⁵ to R ⁸ is represented by Formula 2, at least one of R ⁹ to R ¹² is represented by Formula 2, and R ¹³ to At least one of R ¹⁶ may be represented by Formula 2. For example, R ¹ to R ⁴ are all halogen atoms, at least one of R ⁶ and R ⁷ is represented by Formula 2, at least one of R ¹⁰ and R ¹¹ is represented by Formula 2, and R ^{All of 13} to R ¹⁶ may be halogen atoms.

All of R ¹ to R ⁸ are halogen atoms, at least one of R ⁹ to R ¹² may be represented by Formula 2, and at least one of R ¹³ to R ¹⁶ may be represented by Formula 2. For example, the R ¹ to R ⁸ are all halogen atoms, at least one of R ¹⁰ and R ¹¹ is a substituted or unsubstituted C1 to C20 alkoxy group, and at least one of R ¹⁴ and R ¹⁵ is represented by Formula 2 Can be displayed.

R ¹ to R ⁴ are all halogen atoms, at least one of R ⁵ to R ⁸ is represented by Formula 2, and R ⁹ to R ¹² are all halogen atoms, and at least one of R ¹³ to R ¹⁶ May be represented by Formula 2 above. For example, R ¹ to R ⁴ are all halogen atoms, at least one of R ⁶ and R ⁷ is represented by Formula 2, and R ⁹ to R ¹² are all halogen atoms, and among R ¹⁴ and R ¹⁵ At least one may be represented by Formula 2 above.

For example, the compound represented by Formula 1 may be represented by any one of Formulas 4 to 11 below, but is not limited thereto.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

Since the compound according to an embodiment contains two or more substituents represented by the above formula (2), it is possible to express a more vivid color even in a small amount, and when used as a colorant, the display device having excellent color characteristics such as brightness and contrast ratio Manufacturing is possible. For example, the compound may be a colorant, such as a dye, such as a green dye, such as a dye having a maximum transmittance in the wavelength range of 445 nm to 560 nm.

In general, dyes are the most expensive constituents among the constituents used in color filters. Therefore, in order to achieve a desired effect, such as high luminance or high contrast ratio, more expensive dyes must be used, resulting in an increase in production cost. However, when the compound according to an embodiment is used as a dye in a color filter, excellent color characteristics such as high luminance and high contrast ratio can be achieved even with a small amount, so that the production cost can be reduced.

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

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

The compound according to an embodiment may serve as a colorant, such as a dye, such as a green dye, in the photosensitive resin composition, and may exhibit excellent color characteristics.

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

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

The yellow pigment is C.I. in the Color Index. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment yellow 150, etc. are mentioned, and these can be used individually or in mixture of 2 or more types.

The green pigment is C.I. in the Color Index. Pigment Green 36, C.I. Pigment Green 58, C.I. Pigment green 59, etc. are mentioned, and these can be used individually or in mixture of 2 or more types.

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

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

The solid pigment is 1% to 20% by weight, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, such as 10% to 20% by weight, based on the total amount of the pigment dispersion. It may be included in 15% by weight.

Nonionic dispersants, anionic dispersants, cationic dispersants, and the like may be used as the dispersant. Specific examples of the dispersant include polyalkylene glycol and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, alkyl amines, etc., and these may be used alone or in combination of two or more.

For example, the commercially available products of the dispersant are BYK's DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, 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. from EFKA Chemical; Zeneka's Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; Alternatively, there are PB711 and PB821 of Ajinomoto.

The 　 dispersant may be included in an amount of 1% to 20% by weight based on the total amount of the pigment dispersion. When the dispersant is included within the above range, it is possible to maintain an appropriate viscosity, so that the photosensitive resin composition has excellent dispersibility, and thus optical, physical and chemical quality can be maintained when the product is applied.

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

The pigment dispersion may be included in an amount of 10% to 20% by weight, such as 12% to 18% by weight, based on the total amount of the photosensitive resin composition. When the pigment dispersion is included within the above range, it is advantageous to secure a process margin, and a color reproducibility and contrast ratio are 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 including at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxy group, and specific examples thereof include 　acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

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

The second ethylenically unsaturated monomers include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzylmethylether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth)acrylate and phenyl (meth)acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds such as (meth)acrylonitrile; Unsaturated amide compounds such as (meth)acrylamide; And the like, and these may be used alone or in combination of two or more.

Specific examples of the acrylic resin include (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/benzyl methacrylate/2-hydroxyethyl methacrylate Rate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like, but are not limited thereto, and these may be used alone or in combination 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, such as 20,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the alkali-soluble resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, has an appropriate viscosity, and has excellent adhesion to a substrate when manufacturing a color filter.

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

The alkali-soluble resin may be included in an amount of 1% to 30% by weight, such as 1% to 20% by weight, based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is included within the above range, developability is excellent and crosslinking property is improved when manufacturing a color filter, thereby obtaining excellent surface smoothness.

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

Since the photopolymerizable compound has the ethylenically unsaturated double bond, it is possible to form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation process.

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

Commercially available products of photopolymerizable compounds are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ^®, the same M-111 ^®, the same M-114 ^®; KAYARAD TC-110S ^® of Nihon Kayaku Co., Ltd., TC-120S ^®, etc.; Osaka yukki the like Kagaku Kogyo (main)社of ^{V-158 ®, V-2311} ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ^®, copper or the like M-240 ^®, the same M-6200 ^®; KAYARAD HDDA ^® , HX-220 ^® , R-604 ^{® of} Nihon Kayaku Co., Ltd.; Osaka Yuki Kagaku High School Co., Ltd.'s V-260 ^® , V-312 ^® , and V-335 HP ^® are listed. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ^®, the same M-400 ^®, the same M-405 ^®, the same M-450 ^®, Dong M -710 ^® , M-8030 ^® , M-8060 ^®, etc.; Nippon Kayaku (Note)社of KAYARAD TMPTA ^®, copper DPCA-20 ^{®, ®} copper -30, -60 ^® copper, copper ^® -120 and the like; Osaka Yuki Kayaku High School Co., Ltd.'s V-295 ^® , East-300 ^® , East-360 ^® , East-GPT ^® , East-3PA ^® , and East-400 ^® are listed. The above products can be used alone or in combination of two or more.

The photopolymerizable compound may be used after treatment with an acid anhydride in order to impart better developability.

The photopolymerizable compound may be included in an amount of 1% to 15% by weight, such as 5% to 10% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, hardening occurs sufficiently during exposure in the pattern formation process, so that reliability is excellent, and developability to an alkali developer is excellent.

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, an oxime compound, or a combination thereof You can use

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

Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4 '-Bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, and the like.

Examples of the thioxanthone-based compound include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- And chloro thioxanthone.

Examples of the benzoin-based compound include 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 include 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(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4, 6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-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, etc. are mentioned.

Examples of the oxime-based compound include O-acyloxime-based compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime )-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one Etc. can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane- 1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione2 -Oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime-O- Acetate, etc. are mentioned.

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

The photopolymerization initiator may be used together with a photosensitizer that absorbs light and becomes excited, and then transmits the energy to cause a chemical reaction.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, etc. Can be mentioned.

The photopolymerization initiator may be included in an amount of 0.01% to 10% by weight, such as 0.1% to 5% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, curing occurs sufficiently during exposure in the pattern formation process to obtain excellent reliability, excellent heat resistance, light resistance and chemical resistance of the pattern, excellent resolution and adhesion, and due to the unreacted initiator It is possible to prevent a decrease in transmittance.

The solvent may have compatibility with a compound, a pigment, an alkali-soluble resin, a photopolymerizable compound, and a photopolymerization initiator according to an exemplary embodiment, but materials that do not react.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactate esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl methoxy acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxypropionic acid alkyl esters such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-alkoxy propionic acid alkyl esters such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, and 3-ethoxy methyl propionate; 2-oxypropionic acid alkyl esters such as 2-oxy methyl propionate, 2-oxy ethyl propionate, and 2-oxy propionate propyl; 2-alkoxy propionic acid alkyl esters such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate, and 2-ethoxy methyl propionate; 2-oxy-2-methyl propionic acid esters such as 2-oxy-2-methyl methyl propionate and 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2- Monooxy monocarboxylic acid alkyl esters of alkyl 2-alkoxy-2-methyl propionate such as ethyl methyl propionate; Esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate, and 2-hydroxy-3-methyl methyl butanoate; Ketone acid esters such as ethyl pyruvate, and the like, and N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, N,N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, capronic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid High boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among these, in consideration of compatibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; And/or ketones such as cyclohexanone may be used.

The solvent may be included in the balance, for example, 30% to 80% by weight based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, the photosensitive resin composition has an appropriate viscosity, and thus processability is excellent in manufacturing a color filter.

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

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

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, based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included within the above range, adhesion and storage properties are excellent.

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

Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ-methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glycidok Cypropyl trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more.

The silane coupling agent may be included in an amount of 0.01 parts by weight to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is included within the above range, adhesion and storage properties are excellent.

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

Examples of the surfactants include, BM Chemie BM-1000 ^® of社, BM-1100 ^®, and the like; Mecha Pack F 142D ^® , F 172 ^® , F 173 ^® , F 183 ^{® of} Dai Nippon Inki Chemical Co., Ltd.; Sumitomo M. (Note)社Pro rod FC-135 ^®, the same FC-170C ^®, copper FC-430 ^®, the same FC-431 ^®, and the like; Asahi Grass Co., Saffron S-112 ^® of社, such S-113 ^®, the same S-131 ^®, the same S-141 ^®, the same S-145 ^®, and the like; Toray silicone (Note)社SH-28PA ^®, copper -190 ^®, may be used copper ^® -193, fluorine-based surfactants and commercially available under the name, such as ^{SZ-6032 ®, SF-8428} ®.

The surfactant may be used in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the above range, coating uniformity is ensured, stains do not occur, and wettability to the glass substrate is excellent.

In addition, a certain amount of other additives such as antioxidants and stabilizers may be added to the photosensitive resin composition within a range that does not impair physical properties.

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

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

Applying the photosensitive resin composition onto a supporting substrate by spin coating, slit coating, inkjet printing, or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film to light; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to prepare a photosensitive resin film; And a step of heat treating the photosensitive resin film. Since the above process conditions are widely known in the art, detailed descriptions thereof will be omitted herein.

Hereinafter, the present invention will be described in more detail with reference to examples, but the following examples are only preferred examples of the present invention, and the present invention is not limited to the following examples.

(Synthesis of compounds)

Synthesis example One- 1: 3 ,4,6-Trichloro-5-(4- methoxy -2-methyl- phenoxy Synthesis of )-phthalonitrile

In a 100ml flask, 3,4,5,6-tetrachlorophthalonitrile (5g), 4-methoxy-2-methylphenol (3.12g), K ₂ CO ₃ (3.9g), N,N-dimethylformamide (N,N-dimethylformamide) )(25ml) was added and stirred while heating to 70℃. After completion of the reaction, extraction was performed with ethyl acetate (EA). When concentrated after extraction, a solid can be obtained. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to obtain 3,4,6-Trichloro-5-(4-methoxy-2-methyl-phenoxy)-phthalonitrile.

Synthesis example One- 2: 4 -(2- tert -Butyl-4- methoxy - phenoxy )-3,5,6- trichloro - phthalonitrile synthesis

In a 100ml flask, 3,4,5,6-tetrachlorophthalonitrile (5g), 2-tert-Butyl-4-methoxyphenol (4.07g), K ₂ CO ₃ (3.9g), N,N-dimethylformamide (N,N Add -dimethylformamide) (25ml) and stir while heating to 70℃. After completion of the reaction, extraction was performed with ethyl acetate (EA). When concentrated after extraction, a solid can be obtained. The solid obtained at this time was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 4-(2-tert-Butyl-4-methoxy-phenoxy)-3,5,6-trichloro-phthalonitrile. Get

Synthesis example 1: Synthesis of a compound represented by Formula 4

In a 100 mL flask, 3,4,6-Trichloro-5-(4-methoxy-2-methyl-phenoxy)-phthalonitrile (2g), 1,8-Diazabicycloundec-7-ene (1.04g) of Synthesis Example 1-1, and Add 1-pentanol (10g) and heat to 90℃ to dissolve the solid, then add zinc acetate (0.25g) and stir while heating to 140℃. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried under vacuum to obtain a compound represented by the following formula (4).

[Formula 4]

Maldi-tof MS: 1527.82 m/z

Synthesis example 2: Synthesis of the compound represented by Formula 5

In a 100 mL flask, 3,4,6-Trichloro-5-(4-methoxy-2-methyl-phenoxy)-phthalonitrile (1.5 g), 3,4,5,6-Tetrachlorophthalonitrile (0.36 g) of Synthesis Example 1-1 , 1,8-Diazabicycloundec-7-ene (1.04g) and 1-pentanol (14g) were added and heated to 90°C to dissolve the solid, then zinc acetate (0.25g) was added and stirred while heating to 140°C. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula (5).

[Formula 5]

Maldi-tof MS: 1425.72 m/z

Synthesis example 3: Synthesis of the compound represented by Formula 6

In a 100 mL flask, 3,4,6-Trichloro-5-(4-methoxy-2-methyl-phenoxy)-phthalonitrile (1.1 g), 3,4,5,6-Tetrachlorophthalonitrile (0.80 g) of Synthesis Example 1-1 , 1,8-Diazabicycloundec-7-ene (1.14g) and 1-pentanol (14g) were added and heated to 90°C to dissolve the solid, then zinc acetate (0.27g) was added and heated to 140°C while stirring. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula (6).

[Formula 6]

Maldi-tof MS: 1323.64 m/z

Synthesis example 4: Synthesis of a compound represented by Formula 7

In a 100 mL flask, 3,4,6-Trichloro-5-(4-methoxy-2-methyl-phenoxy)-phthalonitrile (1.5g), 3,4,6-Trichloro-5-pentyloxy-phthalonitrile of Synthesis Example 1-1 (0.43g), 1,8-Diazabicycloundec-7-ene (1.04g) and 1-pentanol (14g) were added and heated to 90℃ to dissolve the solid, then zinc acetate (0.25g) was added and heated to 140℃. Stir. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula (7).

[Formula 7]

Maldi-tof MS: 1477.84 m/z

Synthesis example 5: Synthesis of the compound represented by Formula 8

In a 100 mL flask, 4-(2-tert-Butyl-4-methoxy-phenoxy)-3,5,6-trichloro-phthalonitrile (2g), 1,8-Diazabicycloundec-7-ene (0.93g) of Synthesis Example 1-2 ) And 1-pentanol (10g) are added and heated to 90°C to dissolve the solid, then zinc acetate (0.22g) is added and heated to 140°C while stirring. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula (8).

[Formula 8]

Maldi-tof MS: 1696.01 m/z

Synthesis example 6: Synthesis of the compound represented by Formula 9

In a 100 mL flask, 4-(2-tert-Butyl-4-methoxy-phenoxy)-3,5,6-trichloro-phthalonitrile (1.5g), 3,4,5,6-Tetrachlorophthalonitrile (0.32) of Synthesis Example 1-2 g), 1,8-Diazabicycloundec-7-ene (0.93g) and 1-pentanol (14g) are added and heated to 90℃ to dissolve the solid, then zinc acetate (0.22g) is added and heated to 140℃ while stirring. . After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried under vacuum to obtain a compound represented by the following formula (9).

[Formula 9]

Maldi-tof MS: 1551.87 m/z

Synthesis example 7: Synthesis of the compound represented by Formula 10

In a 100 mL flask, 4-(2-tert-Butyl-4-methoxy-phenoxy)-3,5,6-trichloro-phthalonitrile (1.1g), 3,4,5,6-Tetrachlorophthalonitrile (0.71) of Synthesis Example 1-2 g), 1,8-Diazabicycloundec-7-ene (1.02g) and 1-pentanol (14g) are added and heated to 90℃ to dissolve the solid, then zinc acetate (0.25g) is added and heated to 140℃ while stirring. . After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by Formula 10 below.

[Formula 10]

Maldi-tof MS: 1407.73 m/z

Synthesis example 8: Synthesis of the compound represented by Formula 11

In a 100 mL flask, 3,4,6-Trichloro-5-(4-methoxy-2-methyl-phenoxy)-phthalonitrile (1.5g), 3,4,6-Trichloro-5-pentyloxy-phthalonitrile of Synthesis Example 1-1 (0.39g), 1,8-Diazabicycloundec-7-ene (0.93g) and 1-pentanol (14g) were added and heated to 90℃ to dissolve the solid, then zinc acetate (0.22g) was added and heated to 140℃. Stir. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula (11).

[Formula 11]

Maldi-tof MS: 1603.98 m/z

compare Synthesis example 1: Synthesis of a compound represented by Formula C-1

In a 100 mL flask, 4-(2-sec-Butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (1 g), 1,8-Diazabicycloundec-7-ene (0.30 g), 1-pentanol (7 g), Add zinc acetate (0.12g) and stir while heating to 140℃. After completion of the reaction, the mixture was concentrated and purified through column chromatography. The liquid obtained after purification is concentrated to obtain a solid. The crystallized solid was vacuum-dried to obtain a compound represented by the following formula (C-1).

[Chemical Formula C-1]

Maldi-tof MS: 1584.04 m/z

compare Synthesis example 2: Synthesis of a compound represented by Formula C-2

In a 100ml flask, 3,4,5,6-tetrachlorophthalonitrile (5g), 2,4-dimethylphenol (2.75g), K ₂ CO ₃ (3.9g), N,N-dimethylformamide (N,N-dimethylformamide) ( 25ml) and stirred while heating to 70°C. After completion of the reaction, extraction was performed with ethyl acetate (EA). When concentrated after extraction, a solid can be obtained. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to obtain 3,4,6-Trichloro-5-(2,4-dimethyl-phenoxy)-phthalonitrile.

In a 100 mL flask, add 3,4,6-Trichloro-5-(2,4-dimethyl-phenoxy)-phthalonitrile (1 g), 1,8-Diazabicycloundec-7-ene (1.08 g) and 1-pentanol (14 g). The mixture is heated to 90°C to dissolve the solid, and then zinc acetate (0.26g) is added and heated to 140°C while stirring. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula C-2.

[Formula C-2]

Maldi-tof MS: 1463.84 m/z

compare Synthesis example 3: Synthesis of a compound represented by Formula C-3

In a 100ml flask, 3,4,5,6-tetrachlorophthalonitrile (5g), 2,4-dimethoxyphenol (3.47g), K ₂ CO ₃ (3.9g), N,N-dimethylformamide (N,N-dimethylformamide) ( 25ml) and stirred while heating to 70°C. After completion of the reaction, extraction was performed with ethyl acetate (EA). When concentrated after extraction, a solid can be obtained. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried under vacuum to obtain 3,4,6-Trichloro-5-(2,4-dimethoxy-phenoxy)-phthalonitrile.

In a 100 mL flask, add 3,4,6-Trichloro-5-(2,4-dimethoxy-phenoxy)-phthalonitrile (2 g), 1,8-Diazabicycloundec-7-ene (0.99 g) and 1-pentanol (14 g). The mixture is heated to 90℃ to dissolve the solid, and then zinc acetate (0.24g) is added and heated to 140℃ while stirring. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by the following formula C-3.

[Chemical Formula C-3]

Maldi-tof MS: (1591.80 m/z

compare Synthesis example 4: Synthesis of a compound represented by Formula C-4

In a 100 mL flask, 4-(2,4-dimethoxy-phenoxy)-3,5,6-trichloro-phthalonitrile (0.7g), 3,4,5,6-Tetrachlorophthalonitrile (1.45g), 1 of Synthesis Example 1-2 Add ,8-Diazabicycloundec-7-ene (1.38g) and 1-pentanol (14g) and heat to 90℃ to dissolve the solid, then add zinc acetate (0.33g) and heat to 140℃ while stirring. After completion of the reaction, the precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. After purification, the obtained solid eddichloromethane is appropriately added to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried in vacuo to obtain a compound represented by Formula C-4 below.

[Chemical Formula C-4]

Maldi-tof MS: 1237.54 m/z

Evaluation 1: solubility measurement

To 0.5 g of the compounds according to Synthesis Examples 1 to 8 and Comparative Synthesis Examples 1 to 4, a diluting solvent (PGMEA) was added, respectively, and the solution was mixed with a rotor (MIXROTAR VMR-5) After stirring at 25° C. and 100 rpm for 1 hour, the results of confirming the solubility of each compound are shown in Table 1 below.

Solubility evaluation criteria

Compound (solute) is dissolved in at least 10% by weight based on the total amount of the diluted solvent: ○

Compound (solute) is 5% by weight or more and less than 10% by weight, based on the total amount of the diluted solvent: △

Dissolution of less than 5% by weight of compound (solute) based on the total amount of diluent: X

(Unit: wt%) Solubility Synthesis Example 1 ○ Synthesis Example 2 △ Synthesis Example 3 △ Synthesis Example 4 ○ Synthesis Example 5 ○ Synthesis Example 6 △ Synthesis Example 7 △ Synthesis Example 8 ○ Comparative Synthesis Example 1 X Comparative Synthesis Example 2 X Comparative Synthesis Example 3 X Comparative Synthesis Example 4 X

From Table 1, the compounds of Synthesis Examples 1 to 8, which are compounds according to an embodiment, have better solubility in organic solvents than the compounds of Comparative Synthesis Examples 1 to 4, and are excellent when used in photosensitive resin compositions, etc. It can be seen that it can show color characteristics.

(Synthesis of photosensitive resin composition)

Example One

A photosensitive resin composition according to Example 1 was prepared by mixing the components mentioned below in the composition shown in Table 2 below.

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

(Unit: wt%) Ingredients content coloring agent dyes Compound of Synthesis Example 1 5.0 Pigment dispersion Pigment Y138 pigment dispersion 15.0 Alkali-soluble resin (A)/(B)=15/85(w/w),
Molecular weight (Mw)=22,000g/mol
(A): methacrylic acid
(B): Benzyl methacrylate 3.5 Photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 8.0 Photopolymerization initiator 1,2-octanedione 1.0 2-Dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one 0.5 menstruum Cyclohexanone 37.0 PGMEA (Propylene Glycol Monomethyl Ether Acetate) 30.0 Total 100.00

Example 2

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

Example 3

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

Example 4

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

Example 5

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

Example 6

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

Example 7

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

Example 8

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

Comparative example One

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

Comparative example 2

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

Comparative example 3

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

Comparative example 4

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

Comparative example 5

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the composition shown in Table 3 was mixed instead of the composition shown in Table 1 below.

(Unit: wt%) Ingredients content coloring agent Pigment dispersion Pigment G58 pigment dispersion 20.0 Pigment Y138 pigment dispersion 15.0 Alkali-soluble resin (A)/(B)=15/85(w/w),
Molecular weight (Mw)=22,000g/mol
(A): methacrylic acid
(B): Benzyl methacrylate 2.5 Photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 5.0 Photopolymerization initiator 1,2-octanedione 1.0 2-Dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one 0.5 menstruum Cyclohexanone 40.0 PGMEA (Propylene Glycol Monomethyl Ether Acetate) 16.0 Total 100.00

Comparative example 6

A photosensitive resin composition was prepared in the same manner as in Comparative Example 5, except that Pigment G36 pigment dispersion was used instead of Pigment G58 pigment dispersion.

Evaluation 2: Color coordinates , Brightness and contrast ratio measurement

The photosensitive resin composition prepared in Examples 1 to 8 and Comparative Examples 1 to 6 was applied to a thickness of 1 µm to 3 µm on a degreasing and washed glass substrate, and a hot plate at 90°C Drying on the bed for 2 minutes to obtain a coating film. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a dominant wavelength of 365 nm. Thereafter, it was dried for 5 minutes in a hot air circulation drying furnace at 200° C. to obtain a sample. For the pixel layer, the luminance (Y) and contrast ratio were measured using a spectrophotometer (MCPD3000, Otsuka electronic), and are shown in Table 4 below.

Luminance (Y) Contrast ratio Example 1 62.7 15,700 Example 2 62.5 15,400 Example 3 62.8 15,500 Example 4 62.4 15,300 Example 5 62.6 15,300 Example 6 62.3 15,000 Example 7 62.5 14,900 Example 8 62.3 15,200 Comparative Example 1 61.0 14,400 Comparative Example 2 60.8 14,600 Comparative Example 3 60.1 14,300 Comparative Example 4 59.7 14,100 Comparative Example 5 60.9 13,300 Comparative Example 6 58.6 13,600

From Table 4, the photosensitive resin compositions of Examples 1 to 8 including the compound according to an embodiment as a dye exhibit superior color characteristics than the photosensitive resin compositions of Comparative Examples 1 to 6 not including the compound. It can be confirmed that it appears.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims, the detailed description of the invention, and the accompanying drawings. It is natural to fall within the scope of the invention.

Claims (18)

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

In Formula 1,
R ¹ to R ⁴ are each independently a halogen atom or a substituted or unsubstituted C1 to C20 alkoxy group,
R ⁵ to R ⁸ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group or an aryloxy group represented by the following formula (3),
R ⁹ to R ¹² are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group or an aryloxy group represented by the following formula (3),
R ¹³ to R ¹⁶ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group or an aryloxy group represented by the following formula (3),
However, at least two or more of R ⁵ to R ¹⁶ are represented by the following formula (3),
[Formula 3]

In Chemical Formula 3,
R ¹⁷ is a substituted or unsubstituted C1 to C20 alkyl group,
R ¹⁸ is a substituted or unsubstituted C1 to C20 alkoxy group.
delete The method of claim 1,
Wherein R ¹⁷ is a tert-butyl group.
delete delete The method of claim 1,
At least one of the R ¹ to R ⁴ is a substituted or unsubstituted C1 to C20 alkoxy group,
At least one of R ⁵ to R ⁸ is represented by Formula 3,
At least one of R ⁹ to R ¹² is represented by Formula 3,
At least one of R ¹³ to R ¹⁶ is a compound represented by Formula 3.
The method of claim 1,
All of the R ¹ to R ⁴ are halogen atoms,
At least one of R ⁵ to R ⁸ is represented by Formula 3,
At least one of R ⁹ to R ¹² is represented by Formula 3,
At least one of R ¹³ to R ¹⁶ is a compound represented by Formula 3.
The method of claim 1,
All of the R ¹ to R ⁸ are halogen atoms,
At least one of R ⁹ to R ¹² is represented by Formula 3,
At least one of R ¹³ to R ¹⁶ is a compound represented by Formula 3.
The method of claim 1,
All of the R ¹ to R ⁴ are halogen atoms,
At least one of R ⁵ to R ⁸ is represented by Formula 3,
All of R ⁹ to R ¹² are halogen atoms,
At least one of R ¹³ to R ¹⁶ is a compound represented by Formula 3.
The method of claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 5 to 7 and Formulas 9 to 11.
[Formula 5]

[Formula 6]

[Formula 7]

[Formula 9]

[Formula 10]

[Formula 11]

The method of claim 1,
The compound is a green dye.
The method of claim 11,
The green dye is a compound having a maximum transmittance in a wavelength range of 445nm to 560nm.
A photosensitive resin composition comprising the compound of any one of claims 1, 3 and 6 to 12.
The method of claim 13,
The compound is a photosensitive resin composition containing 1% by weight to 10% by weight based on the total amount of the photosensitive resin composition.
The method of claim 13,
The photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
The method of claim 15,
The photosensitive resin composition is a photosensitive resin composition further comprising a pigment.
The method of claim 16,
The pigment is a photosensitive resin composition comprising a yellow pigment, a green pigment, or a combination thereof.
A color filter manufactured using the photosensitive resin composition of claim 13.