KR20170142096A - Novel compound,photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

Provided are a compound represented by chemical formula 1, a photosensitive resin composition containing the same, and a color filter produced by using the photosensitive resin composition. The detailed description of the chemical formula 1 is the same as defined in the present specification. According to an embodiment of the present invention, the compound of the present invention shows excellent spectral characteristics in green and high molar extinction coefficient.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, a photosensitive resin composition containing the same and a color filter,

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

In a color filter made of a pigment type photosensitive resin composition, there is a limit of luminance and contrast ratio resulting from the pigment particle size. Further, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet such a demand, attempts have been made to fabricate a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment, thereby realizing a color filter having improved color characteristics such as brightness and contrast ratio.

Therefore, it is necessary to study 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 above compound.

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

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

[Chemical Formula 1]

In Formula 1,

R ¹ to R ¹⁶ are each 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 aryl group, A substituted or unsubstituted C6 to C20 aryloxy group,

Provided that at least one of R ¹ to R ¹⁶ is represented by the following formula (2)

(2)

In Formula 2,

R ¹⁷ and R ¹⁸ are each independently a halogen atom,

n1 and n2 are each independently an integer of 0 to 5, provided that 1? n1 + n2? 5.

The formula (2) may be represented by any one selected from the group consisting of the following formulas (3-1) to (3-4).

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

In the above Formulas 3-1 to 3-4,

R ¹⁷ and R ¹⁸ are each independently a halogen atom.

At least one of R ¹ to R ¹⁶ is represented by Formula 2, and at least one of R ¹ to R ¹⁶ may be represented by Formula 4 below.

[Chemical Formula 4]

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 4, and at least one of R ⁹ to R ¹² is represented by Formula 4 at least one of said R ¹³ to R ¹⁶ may be represented by the general formula (4).

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 4 at least one of said R ¹³ to R ¹⁶ may be represented by the general formula (4).

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 4, and at least one of R ⁹ to R ¹² is represented by Formula 2 at least one of said R ¹³ to R ¹⁶ may be represented by the general formula (4).

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 said R ¹³ to R ¹⁶ may be represented by the general formula (4).

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 said R ¹³ to R ¹⁶ may be represented by the general formula (2).

The compound represented by the formula (1) may be represented by any one of the following formulas (5) to (14).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

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 above compound.

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

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

The photosensitive resin composition may further comprise a pigment.

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

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

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

The compound according to one embodiment has excellent green spectroscopic characteristics and a high molar extinction coefficient and is excellent in solubility in an organic solvent and can be used as a dye in the production of a photosensitive resin composition for a green color filter. Excellent brightness and contrast ratio can be obtained.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

Means that at least one hydrogen atom of the functional group of the present invention is substituted with 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, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group.

Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.

(Meth) acrylate "refers to both" acrylic acid "and" methacrylic acid " It means both are possible.

As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.

In addition, unless otherwise defined herein, "*" means the same or different atom or moiety connected to the formula.

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

[Chemical Formula 1]

In Formula 1,

R ¹ to R ¹⁶ are each 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 aryl group, A substituted or unsubstituted C6 to C20 aryloxy group,

Provided that at least one of R ¹ to R ¹⁶ is represented by the following formula (2)

(2)

In Formula 2,

R ¹⁷ and R ¹⁸ are each independently a halogen atom,

n1 and n2 are each independently an integer of 0 to 5, provided that 1? n1 + n2? 5.

The compound represented by Formula 1 has excellent green spectroscopic characteristics and a high molar extinction coefficient. Further, since the compound represented by Formula (1) necessarily includes the substituent represented by Formula (2), it can exhibit excellent solubility in an organic solvent and excellent brightness and contrast ratio when applied to a color filter.

The formula (2) may be represented by any one selected from the group consisting of the following formulas (3-1) to (3-4).

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

In the above Formulas 3-1 to 3-4,

R ¹⁷ and R ¹⁸ are each independently a halogen atom.

The substituents represented by the above formulas (3-1) to (3-4) are all aryloxy groups having at least one halogen atom substituted. In particular, when the halogen atom is substituted at the ortho and / or para positions, The luminance and the contrast ratio can be further improved. When the halogen atom is substituted (two halogen atoms substituted) at both the ortho and para positions, the halogen atom is substituted only at the ortho or para position Halogen atom substitution), the luminance and contrast ratio are improved. However, when the halogen atom is substituted at the meta position (even if another halogen atom is substituted at the ortho and / or para positions), the effect of improving the luminance and the contrast ratio is insignificant.

That is, in the substituent represented by the general formula (2), for example, the substituent represented by the general formulas (3-1) to (3-4), i) when at least one halogen atom is substituted at the meta position, ii) when the halogen atom is ortho- ii) iii) when the halogen atom is substituted at any position of the ortho and para positions, iii) when the halogen atom is substituted at both the ortho and para positions, The luminance and the contrast ratio can be further improved.

At least one of R ¹ to R ¹⁶ is represented by Formula 2, and at least one of R ¹ to R ¹⁶ may be represented by Formula 4 below.

[Chemical Formula 4]

For example, the substituent represented by the formula (4) may be represented by the following formula (4-1).

[Formula 4-1]

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 4, and at least one of R ⁹ to R ¹² is represented by Formula 4 at least one of said R ¹³ to R ¹⁶ may be represented by the general formula (4).

For example, R ² or R ³ may be represented by Formula 2, R ⁶ or R ⁷ may be represented by Formula 4, R ¹⁰ or R ¹¹ may be represented by Formula 4, R ¹⁴ or R ¹⁵ May be represented by the formula (4).

For example, R ² or R ³ may be represented by Formula 2, R ⁶ or R ⁷ may be represented by Formula 4, R ¹⁰ or R ¹¹ may be represented by Formula 4, R ¹⁴ or R ¹⁵ May be represented by the general formula (4), and all the residues not represented by the general formulas (2) and (4) may be halogen atoms.

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 4 at least one of said R ¹³ to R ¹⁶ may be represented by the general formula (4).

For example, R ² or R ³ may be represented by Formula 2, R ⁶ or R ⁷ may be represented by Formula 2, R ¹⁰ or R ¹¹ may be represented by Formula 4, R ¹⁴ or R ¹⁵ May be represented by the formula (4).

For example, R ² or R ³ may be represented by Formula 2, R ⁶ or R ⁷ may be represented by Formula 2, R ¹⁰ or R ¹¹ may be represented by Formula 4, R ¹⁴ or R ¹⁵ May be represented by the general formula (4), and all the residues not represented by the general formulas (2) and (4) may be halogen atoms.

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 4, and at least one of R ⁹ to R ¹² is represented by Formula 2 at least one of said R ¹³ to R ¹⁶ may be represented by the general formula (4).

For example, R ² or R ³ may be represented by Formula 2, R ⁶ or R ⁷ may be represented by Formula 4, R ¹⁰ or R ¹¹ may be represented by Formula 2, R ¹⁴ or R ¹⁵ May be represented by the formula (4).

For example, R ² or R ³ may be represented by Formula 2, R ⁶ or R ⁷ may be represented by Formula 4, R ¹⁰ or R ¹¹ may be represented by Formula 2, R ¹⁴ or R ¹⁵ May be represented by the general formula (4), and all the residues not represented by the general formulas (2) and (4) may be halogen atoms.

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 said R ¹³ to R ¹⁶ may be represented by the general formula (4).

For example, R ² or R ³ is represented by Formula 2, R ⁶ or R ⁷ is represented by Formula 2, R ¹⁰ or R ¹¹ is represented by Formula 2, R ¹⁴ or R ¹⁵ May be represented by the formula (4).

For example, R ² or R ³ is represented by Formula 2, R ⁶ or R ⁷ is represented by Formula 2, R ¹⁰ or R ¹¹ is represented by Formula 2, R ¹⁴ or R ¹⁵ May be represented by the general formula (4), and all the residues not represented by the general formulas (2) and (4) may be halogen atoms.

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 said R ¹³ to R ¹⁶ may be represented by the general formula (2).

For example, R ² or R ³ is represented by Formula 2, R ⁶ or R ⁷ is represented by Formula 2, R ¹⁰ or R ¹¹ is represented by Formula 2, R ¹⁴ or R ¹⁵ May be represented by the formula (2).

For example, R ² or R ³ is represented by Formula 2, R ⁶ or R ⁷ is represented by Formula 2, R ¹⁰ or R ¹¹ is represented by Formula 2, R ¹⁴ or R ¹⁵ Is represented by the general formula (2), and all the residues not represented by the general formula (2) may all be halogen atoms.

For example, the compound represented by the formula (1) may be represented by any one of the following formulas (5) to (14), but is not limited thereto.

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

Since the compound according to one embodiment contains a substituent represented by any one of the above-mentioned formulas (2), (3-1) to (3-4), for example, a clearer color can be expressed in a small amount, It is possible to manufacture a display device having excellent color characteristics such as contrast ratio and the like. For example, the compound may be a colorant such as a dye, such as a green dye, e.g., a dye having a maximum transmittance in the wavelength range of 445 nm to 560 nm.

In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, when the compound according to one 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 in a small amount, and production cost can be reduced.

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

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

The compound according to one embodiment serves as a coloring agent, for example, a dye, for example, a green dye in the photosensitive resin composition, and can exhibit 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 according to one embodiment is included in the above range, the color reproducibility and the contrast ratio are excellent .

The photosensitive resin composition may further comprise a pigment, for example, a yellow pigment, a green pigment, or a combination thereof.

The yellow pigments have a C.I. Pigment yellow 139, C.I. Pigment yellow 138, C.I. Pigment yellow 150, etc. These may be used alone or in combination of two or more.

The green pigment has a color index of not less than < RTI ID = 0.0 > C.I. Pigment green 58, C.I. Pigment green 59, etc. These may be used alone or in combination of two or more.

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 may be present in the pigment dispersion in an amount ranging from 1% to 20%, such as 8% to 20%, such as 8% to 15%, such as 10% to 20% 15% by weight.

As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols 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, and alkylamines. These may be used singly or in combination of two or more.

DISPERBYK-161, DISPERBYK-160, DISPERBYK-161, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160 and DISPERBYK-160 of BYK Co., -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.

The dispersing agent may be contained in an amount of 1 to 20% by weight based on the total amount of the pigment dispersion. When the dispersing agent is contained within the above range, the dispersibility of the photosensitive resin composition can be maintained because an appropriate viscosity can be maintained, so that optical, physical and chemical quality can be maintained when the product is applied.

As the 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 can be used.

The pigment dispersion may be contained in an amount of 10% by weight to 20% by weight, for example, 12% by weight to 18% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous in securing a process margin and excellent color reproduction ratio and contrast ratio.

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 with the first ethylenically unsaturated monomer, and is a resin containing at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl 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% by weight to 50% by weight, for example, 10% by weight to 40% by weight based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl 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; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly 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- (Meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited thereto, and they may be used singly or in combination of two or more kinds .

The weight-average molecular weight of the alkali-soluble resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 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, is suitable in viscosity, and has excellent adhesion with a substrate in the production of a color filter.

The acid value of the alkali-soluble resin may be from 15 mgKOH / g to 60 mgKOH / g, for example, from 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 contained in an amount of 1% by weight to 30% by weight, for example, 1% by weight to 20% by weight based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is contained within the above-mentioned range, the color filter is excellent in developability in the production of a color filter, and the cross-linkability is improved, whereby excellent surface smoothness can be obtained.

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

By having the ethylenically unsaturated double bond, the photopolymerizable compound can form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation step.

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, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethacrylate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.

Examples of 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 ^® and TC-120S ^{® from} Nihon Kayaku Co., Ltd.; 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 ^® and R-604 ^{® from} Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of ^{社V-260 ®, V-} 312 ®, V-335 HP ®. 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 ^® , copper M-8030 ^® , copper M-8060 ^® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ^®, copper DPCA-20 ^{®, ®} copper -30, -60 ^® copper, copper ^® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ^®, copper ^® -300, -360 ^® copper, copper -GPT ^®, copper -3PA ^®, and the like copper -400 ^®. These products may be used alone or in combination of two or more.

The photopolymerizable compound may be treated with an acid anhydride so as to give better developing properties.

The photopolymerizable compound may be contained in an amount of 1 wt% to 15 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the above-mentioned range, the pattern forming process sufficiently cures upon exposure to light, which is excellent in reliability and developability in an alkaline developer.

The photopolymerization initiator may be, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, an oxime-based compound, or a combination thereof as an initiator generally used in a photosensitive resin composition .

Examples of the acetophenone compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt Dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.

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

Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho- Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) (Trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like.

Examples of the oxime compounds include O-acyloxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Etc. may be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) Acetate and the like.

The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a nonimidazole compound, or a fluorene compound in addition to the above compounds.

The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .

The photopolymerization initiator may be included in an amount of 0.01 wt% to 10 wt%, for example, 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, the photopolymerization initiator is sufficiently cured upon exposure in the pattern formation step to obtain excellent reliability, and the pattern is excellent in heat resistance, light resistance, chemical resistance, resolution and adhesion, It is possible to prevent the transmittance from being lowered.

The solvent may be a compound, a pigment, an alkali-soluble resin, a photopolymerizable compound, and a compound having compatibility with a photopolymerization initiator but not reacting with the compound according to one embodiment.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl 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 methylethylcarbitol, diethylcarbitol, 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- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; 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 ketones such as cyclohexanone.

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

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 novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be contained in an amount of 0.01 to 20 parts by weight, 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 contained within the above range, the adhesiveness and storage stability are excellent.

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 in order to improve the adhesiveness to the substrate.

Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatepropyltriethoxysilane,? -Glycidoxine (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. These may be used alone or in combination of two or more.

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

The above-mentioned photosensitive resin composition may further contain a surfactant for improving coatability and preventing defect formation if necessary.

Examples of the surfactants include, BM Chemie BM-1000 ^® of社, BM-1100 ^®, and the like; Mechacup F 142D ^® , copper F 172 ^® , copper F 173 ^® , copper F 183 ^® and the like manufactured by Dainippon Ink & Chemicals Incorporated; 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 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, uniformity of coating is ensured, no staining occurs, and wetting of the glass substrate is excellent.

The photosensitive resin composition may contain a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.

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

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

Applying the photosensitive resin composition on a support 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; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.

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

(Synthesis of Compound)

Synthetic example 1: 4 - (Biphenyl-2- yloxy ) -3,5,6- trichloro - phthalonitrile  synthesis

Add 3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.21 g), K ₂ CO ₃ (3.9 g) and acetone (25 ml) into a 100 ml flask and stir while heating to 70 ° C. After completion of the reaction, the solid matter is obtained by filtering and distilling off the liquid obtained by washing with acetone. At this time, the obtained solid is dissolved in a small amount of dichloromethane, washed with nucleic acid several times, filtered and vacuum dried to obtain 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile.

Synthetic example 2: 3 , 4,6-Trichloro-5- (2,6- dichloro - phenoxy ) - phthalonitrile  synthesis

3,4,5,6-Tetrachlorophthalonitrile (5 g), 2,6-dichlorophenol (3.06 g), K ₂ CO ₃ (3.9 g) and acetone (25 ml) were placed in a 100 ml flask and stirred while heating to 70 ° C. After completion of the reaction, the solid matter is obtained by filtering and distilling off the liquid obtained by washing with acetone. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered, and vacuum dried to obtain 3,4,6-Trichloro-5- (2,6-dichloro-phenoxy) -phthalonitrile.

Synthetic example 3: 3 , 4,6-Trichloro-5- (2,6-dibromo- phenoxy ) - phthalonitrile  synthesis

To a 100 ml flask was added 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dibromophenol (4.75 g), K ₂ CO ₃ (3.9 g) and N, N-dimethylformamide 25 ml) was added, and the mixture was stirred while heating to 70 ° C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and vacuum dried to obtain 3,4,6-Trichloro-5- (2,6-dibromo-phenoxy) -phthalonitrile.

Synthetic example 4: 3 , 4,6-Trichloro-5- (2,6- difluoro - phenoxy ) - phthalonitrile  synthesis

To a 100 ml flask was added 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-difluorophenol (2.45 g), K ₂ CO ₃ (3.9 g) and N, N-dimethylformamide 25 ml) was added, and the mixture was stirred while heating to 70 ° C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and vacuum dried to obtain 3,4,6-Trichloro-5- (2,6-difluoro-phenoxy) -phthalonitrile.

Synthetic example 5: 3 , 4,6-Trichloro-5- (2- chloro - phenoxy ) - phthalonitrile  synthesis

Add 3,4,5,6-tetrachlorophthalonitrile (5 g), 2-chlorophenol (2.41 g), K ₂ CO ₃ (3.9 g) and acetone (25 ml) into a 100 ml flask and stir while heating to 70 ° C. After completion of the reaction, the solid matter is obtained by filtering and distilling off the liquid obtained by washing with acetone. The resulting solid is dissolved in a small amount of dichloromethane, washed with hexane several times, filtered and vacuum dried to obtain 3,4,6-Trichloro-5- (2-chloro-phenoxy) -phthalonitrile.

Synthetic example 6: 3 , 4,6-Trichloro-5- (2- bromo - phenoxy ) - phthalonitrile  synthesis

N, N-dimethylformamide (25 ml) was added to a 100 ml flask, to which was added 3,4,5,6-tetrachlorophthalonitrile (5 g), 2-bromophenol (3.25 g), K ₂ CO ₃ And the mixture was stirred while heating to 70 ° C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed with hexane several times, filtered and vacuum dried to obtain 3,4,6-Trichloro-5- (2-bromo-phenoxy) -phthalonitrile.

Synthetic example 7: 3 , 4,6-Trichloro-5- (2-fluoro- phenoxy ) - phthalonitrile  synthesis

N, N-dimethylformamide (25 ml) was added to a 100 ml flask, to which were added 3,4,5,6-tetrachlorophthalonitrile (5 g), 2-fluorophenol (2.10 g), K ₂ CO ₃ And the mixture was stirred while heating to 70 ° C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and vacuum dried to obtain 3,4,6-Trichloro-5- (2-fluoro-phenoxy) -phthalonitrile.

Synthetic example 8: 3 , 4,6-Trichloro-5- (2,5- dichloro - phenoxy ) - phthalonitrile  synthesis

Add 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,5-dichlorophenol (3.06 g), K ₂ CO ₃ (3.9 g) and acetone (25 ml) into a 100 ml flask and stir while heating to 70 ° C. After completion of the reaction, the solid matter is obtained by filtering and distilling off the liquid obtained by washing with acetone. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and vacuum dried to obtain 3,4,6-Trichloro-5- (2,5-dichloro-phenoxy) -phthalonitrile.

Synthetic example  9: Synthesis of Compound Represented by Formula 5

(Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (1.5 g) synthesized in Synthesis Example 1, 3,4,6-Trichloro-5- dichloro-phenoxy-phthalonitrile (0.49 g), 1,8-Diazabicycloundec-7-ene (1.52 g) and 1-pentanol (14 g) were added and heated at 90 ° C to dissolve the solid. And the mixture was stirred while heating to 140 ° C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (5).

[Chemical Formula 5]

Mald-tof MS: 1656.79 m / z

Synthetic example  10: Synthesis of Compound Represented by Formula 6

2-yloxy) -3,5,6-trichloro-phthalonitrile (1.6 g) synthesized in Synthesis Example 1, 3,4,6-Trichloro-5- (2,6- dichloro-phenoxy-phthalonitrile (1.5 g), 1,8-diazabicycloundec-7-ene (1.74 g) and 1-pentanol (14 g) And the mixture was stirred while heating to 140 ° C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 (6).

[Chemical Formula 6]

Mald-tof MS: 1649.57 m / z

Synthetic example  11: Synthesis of Compound Represented by Chemical Formula 7

To a 100 mL flask was added 4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (1 g) of Synthesis Example 1, 3,4,6-Trichloro-5- (2.9 g), 1,8-diazabicycloundec-7-ene (3 g) and 1-pentanol (27 g) were added and the solid was dissolved by heating at 90 ° C., zinc acetate Lt; 0 > C while stirring. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (7).

(7)

Mald-tof MS: 1642.36 m / z

Synthetic example  12: Synthesis of Compound Represented by Formula 8

3,4-dichloro-phenoxy) phthalonitrile (1.5 g), 1,8-diazabicycloundec-7-ene (0.87 g) and 1-pentane (7g) and heat at 90 ℃ to dissolve the solid. Add zinc acetate (0.17g) and heat with heating at 140 ℃. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (8).

[Chemical Formula 8]

Mald-tof MS: 1635.14 m / z

Synthetic example  13: Synthesis of Compound Represented by Formula 9

To a 100 mL flask was added 3,4,6-Trichloro-5- (2,6-dibromo-phenoxy) -phthalonitrile (1.5 g), 1,8-Diazabicycloundec-7-ene (0.87 g) (7g) and heat at 90 ℃ to dissolve the solid. Add zinc acetate (0.17g) and heat with heating at 140 ℃. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (9).

[Chemical Formula 9]

Maldi-tof MS: 1990.78m / z

Synthetic example  14: Synthesis of Compound Represented by Formula 10

3,4-dichloro-5- (2,6-difluoro-phenoxy) phthalonitrile (1.5 g), 1,8-diazabicycloundec-7-ene (0.87 g) and 1- (7g) and heat at 90 ℃ to dissolve the solid. Add zinc acetate (0.17g) and heat with heating at 140 ℃. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification to dissolve the solid, and then methanol is added to crystallize it. The crystallized solid is filtered and dried under vacuum to obtain a compound represented by the following general formula (10).

[Chemical formula 10]

Mald-tof MS: 1503.53 m / z

Synthetic example  15: Synthesis of Compound Represented by Formula 11

To a 100 mL flask was added 3,4,6-Trichloro-5- (2-chloro-phenoxy) phthalonitrile (1.5 g), 1,8-Diazabicycloundec-7-ene (0.87 g) 7 g) is added, and the mixture is heated to 90 ° C to dissolve the solid. Then, zinc acetate (0.17 g) is added thereto, and the mixture is stirred while heating to 140 ° C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and vacuum dried to obtain a compound represented by the following general formula (11).

(11)

Maldi-tof MS: 1497.38 < RTI ID = 0.0 > m / z

Synthetic example  16: Synthesis of the compound represented by the formula (12)

To a 100 mL flask was added 3,4,6-Trichloro-5- (2-bromo-phenoxy) phthalonitrile (1.5 g), 1,8-Diazabicycloundec-7-ene (0.87 g) 7 g) is added, and the mixture is heated to 90 ° C to dissolve the solid. Then, zinc acetate (0.17 g) is added thereto, and the mixture is stirred while heating to 140 ° C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (12).

[Chemical Formula 12]

Maldi-tof MS: 1675.19 m / z

Synthetic example  17: Synthesis of compound represented by formula (13)

To a 100 mL flask was added 3,4,6-Trichloro-5- (2-fluoro-phenoxy) phthalonitrile (1.5 g), 1,8-Diazabicycloundec-7-ene (0.87 g) 7 g) is added, and the mixture is heated to 90 ° C to dissolve the solid. Then, zinc acetate (0.17 g) is added thereto, and the mixture is stirred while heating to 140 ° C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (13).

[Chemical Formula 13]

Maldi-tof MS: 1431.57 m / z

Synthetic example  18: Synthesis of the compound represented by the formula (14)

4- (Biphenyl-2-yloxy) -3,5,6-trichloro-phthalonitrile (1.6 g) synthesized in Synthesis Example 1, 3,4,6-Trichloro-5- dichloro-phenoxy-phthalonitrile (1.5 g), 1,8-diazabicycloundec-7-ene (1.74 g) and 1-pentanol (14 g) And the mixture was stirred while heating to 140 ° C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification 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 general formula (14).

[Chemical Formula 14]

Mald-tof MS: 1649.57 m / z

compare Synthetic example  1: Synthesis of Compound Represented by Formula X

(1 g), 1,8-Diazabicycloundec-7-ene (0.30 g), 1-pentanol (7 g), and 4- (2-sec-Butyl-phenoxy) -3,5,6-trichloro-phthalonitrile zinc acetate (0.12 g) was added thereto, followed by stirring at 140 캜. After completion of the reaction, the mixture is concentrated and purified by 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 (X).

(X)

Mald-tof MS: 1584.04 m / z

(Synthesis of photosensitive resin composition)

Example  One

The photosensitive resin composition according to Example 1 was prepared by mixing the following components in the compositions shown in Table 1 below.

Specifically, a photopolymerization initiator was dissolved in a solvent, and the mixture was stirred at room temperature for 2 hours. Then, an alkali-soluble resin and a photopolymerizable compound were added thereto, followed by stirring at room temperature for 2 hours. Next, the obtained reaction product was added with the compound (compound represented by Chemical Formula 5) prepared in Synthesis Example 9 and a pigment (in the form of pigment dispersion) as a colorant, and the mixture was stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: wt%) Ingredients content coloring agent dyes The compound of Synthesis Example 9 5.0 Pigment dispersion Pigment Y138 pigment dispersion 15.0 Alkali-soluble resin (A) / (B) = 15/85 (w / w),
Molecular weight (Mw) = 22,000 g / mol
(A): methacrylic acid
(B): benzyl methacrylate 3.5 Photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 8.0 Photopolymerization initiator 1,2-octanedione 1.0 2- (4-methyl-benzyl) -l- (4-morpholin-4-yl-phenyl) -butan- 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 10 (the compound of Formula 6) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 11 (the compound of Formula 7) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  4

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 12 (the compound of Formula 8) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example 5

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 13 (the compound of Formula 9) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  6

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 14 (the compound of Formula 10) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  7

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 15 (the compound of Formula 11) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  8

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 16 (the compound of Formula 12) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  9

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 17 (the compound of Formula 13) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  10

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 18 (the compound of Formula 14) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  11

Instead of 5 wt% of dyestuff, 3.7 wt% was used, and "2.5 wt% of Pigment G58 pigment dispersion and 13.7 wt% of pigment dispersion of Pigment Y138 pigment" were used instead of "15.0 wt% of Pigment Y138 pigment dispersion" % By weight was used as the photosensitive resin composition.

Example  12

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 10 (the compound of Formula 6) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  13

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 11 (the compound of Formula 7) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  14

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 12 (the compound of Formula 8) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  15

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 13 (the compound of Formula 9) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  16

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 14 (the compound of Formula 10) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  17

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 15 (the compound of Formula 11) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  18

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 16 (the compound of Formula 12) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  19

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 17 (the compound of Formula 13) was used instead of the compound of Synthesis Example 9 (the compound of Formula 5).

Example  20

A photosensitive resin composition was prepared in the same manner as in Example 11, except that the compound of Synthesis Example 18 (the compound of Formula 14) was used in place of the compound of Synthesis Example 9 (the compound of Formula 5).

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 (the compound represented by the general formula X) was used instead of the compound of Synthesis Example 9 (the compound represented by the general formula 5).

Comparative Example  2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that the composition shown in Table 2 was used instead of the composition shown in Table 1.

(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) = 22,000 g / mol
(A): methacrylic acid
(B): benzyl methacrylate 2.5 Photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 5.0 Photopolymerization initiator 1,2-octanedione 1.0 2- (4-methyl-benzyl) -l- (4-morpholin-4-yl-phenyl) -butan- 0.5 menstruum Cyclohexanone 40.0 PGMEA (Propylene Glycol Monomethyl Ether Acetate) 16.0 Total 100.00

Evaluate: measure luminance and contrast

The photosensitive resin composition prepared in Examples 1 to 20, Comparative Example 1 and Comparative Example 2 was coated on a glass substrate having a thickness of 1 mm and washed to a thickness of 1 to 3 占 퐉, For 2 minutes to obtain a coating film. Subsequently, the coating film was exposed using a high-pressure mercury lamp having a main wavelength of 365 nm. Thereafter, the sample was dried in a hot air circulating drying oven at 200 DEG C for 5 minutes to obtain a sample. The pixel layer was measured for luminance (Y) and contrast ratio using a spectrophotometer (MCPD3000, Otsuka electronic Co.), and is shown in Table 3 below.

Luminance (Y) Contrast ratio Example 1 63.2 15,700 Example 2 63.6 15,600 Example 3 63.3 15,200 Example 4 63.3 15,200 Example 5 63.1 15,400 Example 6 62.8 15,300 Example 7 62.9 15,200 Example 8 63.0 15,300 Example 9 62.8 15,500 Example 10 62.6 15,500 Example 11 62.8 14,900 Example 12 63.0 14,800 Example 13 62.9 14,600 Example 14 62.8 14,700 Example 15 62.7 14,800 Example 16 62.6 15,000 Example 17 62.7 14,800 Example 18 62.7 14,700 Example 19 62.5 14,900 Example 20 62.4 14,800 Comparative Example 1 62.3 14,300 Comparative Example 2 62.1 13,800

From the above Table 3, it can be seen that the photosensitive resin compositions of Examples 1 to 20 containing the compound according to one embodiment as a dye, more specifically the photosensitive resin compositions of Examples 1 to 9, It can be confirmed that the photosensitive resin composition of Comparative Example 1 and Comparative Example 2 exhibits color characteristics superior to those of the photosensitive resin composition of Comparative Example 1 and Comparative Example 2.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.

Claims (17)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
R ¹ to R ¹⁶ are each 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 aryl group, A substituted or unsubstituted C6 to C20 aryloxy group,
Provided that at least one of R ¹ to R ¹⁶ is represented by the following formula (2)
(2)

In Formula 2,
R ¹⁷ and R ¹⁸ are each independently a halogen atom,
n1 and n2 are each independently an integer of 0 to 5, provided that 1? n1 + n2? 5.
The method according to claim 1,
Wherein the compound represented by Formula 2 is represented by any one selected from the group consisting of the following Formulas 3-1 to 3-4:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

In the above Formulas 3-1 to 3-4,
R ¹⁷ and R ¹⁸ are each independently a halogen atom.
The method according to claim 1,
At least one of R ¹ to R ¹⁶ is represented by the general formula (2)
Wherein at least one of R ¹ to R ¹⁶ is represented by the following formula (4).
[Chemical Formula 4]

The method of claim 3,
At least one of R &^lt; ¹ > to R &^lt; ⁴ >
At least one of R ⁵ to R ⁸ is represented by the general formula (4)
At least one of R ⁹ to R ¹² is represented by the formula 4,
Wherein at least one of R ¹³ to R ¹⁶ is the compound represented by the general formula (4).
The method of claim 3,
At least one of R &^lt; ¹ > to R &^lt; ⁴ >
At least one of R ⁵ to R ⁸ is represented by the formula 2,
At least one of R ⁹ to R ¹² is represented by the formula 4,
Wherein at least one of R ¹³ to R ¹⁶ is the compound represented by the general formula (4).
The method of claim 3,
At least one of R &^lt; ¹ > to R &^lt; ⁴ >
At least one of R ⁵ to R ⁸ is represented by the general formula (4)
At least one of R ⁹ to R ¹² is represented by the general formula (2)
Wherein at least one of R ¹³ to R ¹⁶ is the compound represented by the general formula (4).
The method of claim 3,
At least one of R &^lt; ¹ > to R &^lt; ⁴ >
At least one of R ⁵ to R ⁸ is represented by the formula 2,
At least one of R ⁹ to R ¹² is represented by the general formula (2)
Wherein at least one of R ¹³ to R ¹⁶ is the compound represented by the general formula (4).
The method according to claim 1,
At least one of R &^lt; ¹ > to R &^lt; ⁴ >
At least one of R ⁵ to R ⁸ is represented by the formula 2,
At least one of R ⁹ to R ¹² is represented by the general formula (2)
At least one of R ¹³ to R ¹⁶ is represented by the formula (2).
The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (5) to (14).
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

The method according to claim 1,
Wherein said compound is a green dye.
11. The method of claim 10,
Wherein the green dye has a maximum transmittance in a wavelength range of 445 nm to 560 nm.
A photosensitive resin composition comprising the compound of any one of claims 1 to 11.
13. The method of claim 12,
Wherein the compound is contained in an amount of 1 wt% to 10 wt% based on the total amount of the photosensitive resin composition.
13. The method of claim 12,
Wherein the photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
15. The method of claim 14,
Wherein the photosensitive resin composition further comprises a pigment.
16. The method of claim 15,
Wherein the pigment comprises a yellow pigment, a green pigment or a combination thereof.
A color filter produced by using the photosensitive resin composition of claim 12.