TW201800497A - Novel compound, photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

A compound represented by Chemical Formula 1, a photosensitive resin composition including the same, and a color filter manufactured using the photosensitive resin composition are provided. [Chemical Formula 1] In Chemical Formula 1, each substituent is the same as defined in the specification. The compound represented by Chemical Formula 1 has excellent green spectral characteristics, a high molar extinction coefficient, and excellent solubility in an organic solvent and thus may be used as a dye for a green photosensitive resin composition for a color filter, and accordingly, a color filter including the dye may have excellent color strength, transmittance, luminance, and contrast ratio.

Description

Novel compounds, photosensitive resin compositions including the same, and color filters

This application claims priority and interest of Korean Patent Application No. 10-2016-0075318 filed with the Korea Intellectual Property Office on June 16, 2016, and Korean Patent Application No. 10 filed on January 9, 2017 at the Korea Intellectual Property Office. The benefit of -2017-0003109, the entire contents of which are incorporated herein by reference.

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

Among many types of displays, liquid crystal display devices have advantages in brightness, thinness, low cost, low operating power consumption, and adhesion to integrated circuits, and have been more widely used in notebook computers, monitors, and TVs. Screen. The liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed; and an upper substrate on which an active circuit portion and an ITO pixel electrode are formed, the active circuit portion A liquid crystal layer, a thin film transistor, and a capacitor layer are included.

Forming each of the plurality of color filters in a pixel region by sequentially stacking a plurality of color filters (generally, three primary colors such as red (R), green (G), and blue (B)) in a predetermined order A color filter is formed to form a black matrix layer in a predetermined pattern on a transparent substrate to form a boundary between pixels. The pigment dispersion method, which is one of the color filter forming methods, provides a color film by repeating a series of processes, such as coating a photopolymerizable composition containing a colorant on a transparent substrate containing a black matrix, thereby forming a film. The pattern is exposed, the unexposed portion is removed with a solvent, and it is thermally cured. The colored photosensitive resin composition for producing a color filter according to the pigment dispersion method generally contains an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, other additives, and the like. The pigment dispersion method is actively used to manufacture LCDs such as mobile phones, notebook computers, monitors, and TVs. However, for the pigment dispersion method, a photosensitive resin composition for a color filter has recently been required to have improved properties as well as an excellent pattern profile. Specifically, higher color reproducibility and higher brightness and high contrast characteristics are urgently needed.

Further, a color filter manufactured using a pigment-type photosensitive resin composition has limitations in brightness and contrast ratio due to pigment fineness. In addition, color image sensor devices for image sensors require smaller dispersed particle diameters to form a fine pattern. In order to meet the requirements, a photosensitive resin composition suitable for a dye has been prepared by introducing a dye which does not form particles instead of a pigment, in an attempt to obtain a color filter having improved brightness and contrast ratio. Therefore, a compound which is suitable as a dye for preparing a photosensitive resin composition and a photosensitive resin composition containing the same are required.

One embodiment provides a novel compound.

Another embodiment provides a photosensitive resin composition comprising the compound.

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

在化學式1中， R¹ 到R¹⁶ 獨立地是氫原子、鹵素原子、經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20烷氧基、經取代或未經取代的C6到C20芳基或經取代或未經取代的C6到C20芳氧基， 限制條件為R¹ 到R¹⁶ 中的至少一個由化學式2表示， [化學式2]

其中在化學式2中， R¹⁷ 和R¹⁸ 獨立地是鹵素原子， n1和n2獨立地是0到5範圍內的整數，且1≤n1+n2≤5。One embodiment provides a compound represented by Chemical Formula 1. [Chemical Formula 1]

In Chemical Formula 1, R ¹ to R ^{16 are} independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, substituted or not a substituted C6 to C20 aryl group or a substituted or unsubstituted C6 to C20 aryloxy group, with the constraint that at least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2, [Chemical Formula 2]

Wherein in Chemical Formula 2, R ¹⁷ and R ^{18 are} independently a halogen atom, and n1 and n2 are independently an integer in the range of 0 to 5, and 1 ≤ n1 + n2 ≤ 5.

[化學式3-2]

[化學式3-3]

[化學式3-4]

其中，在化學式3-1到化學式3-4中， R¹⁷ 和R¹⁸ 獨立地是鹵素原子。Chemical Formula 2 can be represented by one selected from Chemical Formula 3-1 to Chemical Formula 3-4. [Chemical Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Chemical Formula 3-4]

Among them, in Chemical Formula 3-1 to Chemical Formula 3-4, R ¹⁷ and R ^{18 are} independently a halogen atom.

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

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

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

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

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

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

[化學式6]

[化學式7]

[化學式8]

[化學式9]

[化學式10]

[化學式11]

[化學式12]

[化學式13]

[化學式14]

The compound represented by Chemical Formula 1 can be represented by one of Chemical Formula 5 to Chemical Formula 14. [Chemical Formula 5]

[Chemical Formula 6]

[Chemical Formula 7]

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical Formula 10]

[Chemical Formula 11]

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

The compound can be a green dye.

Green dyes have maximum transmission in the 445 nm to 560 nm wavelength range.

Another embodiment provides a photosensitive resin composition containing the compound represented by Chemical Formula 1.

The photosensitive resin composition may contain the compound represented by Chemical Formula 1 in an amount of from 1% by weight to 10% by weight based on the total amount of the photosensitive resin composition.

The photosensitive resin composition may further contain a binder resin, a colorant, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

The photosensitive resin composition may further contain a pigment.

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

Another embodiment provides a color filter made using a photosensitive resin composition.

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

The compound according to one embodiment has excellent green spectral characteristics, a high molar extinction coefficient, and excellent solubility in an organic solvent, and thus can be used as a dye for a green photosensitive resin composition of a color filter, and thus, Color filters containing dyes can have excellent color strength, transmittance, brightness, and contrast ratio.

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

As used herein, the term "substituted", when not specifically defined otherwise, is substituted by a substituent selected from the group consisting of halogen (F, Br, Cl or I), hydroxy, nitro, cyano, amino (NH). ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ^{202 are the} same or different and are independently C1 to C10 alkyl), indenyl, fluorenyl, fluorene a carboxy group, a carboxy 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, substituted Or an unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.

As used herein, the term "alkyl" refers to a C1 to C20 alkyl group and especially a C1 to C15 alkyl group, and the term "cycloalkyl" refers to a C3 to C20 cycloalkyl group and especially C3, when a specific definition is not otherwise provided. To a C18 cycloalkyl group, the term "alkoxy" refers to a C1 to C20 alkoxy group and especially a C1 to C18 alkoxy group, and the term "aryl" refers to a C6 to C20 aryl group and especially a C6 to C18 aryl group, the term "Alkenyl" means C2 to C20 alkenyl and especially C2 to C18 alkenyl, the term "alkylene" means C1 to C20 alkyl and especially C1 to C18 alkyl, and the term "strandyl" is Refers to C6 to C20 extended aryl and especially C6 to C16 extended aryl.

As used herein, when not specifically defined, "(meth)acrylate" means "acrylate" and "methacrylate", and "(meth)acrylic" means "acrylic" and " Methacrylate".

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

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

As used herein, when a specific definition is not otherwise provided, "*" indicates a point in which the same or different atom or chemical formula is attached.

在化學式1中， R¹ 到R¹⁶ 獨立地是氫原子、鹵素原子、經取代或未經取代的C1到C20烷基、經取代或未經取代的C3到C20烷氧基、經取代或未經取代的C6到C20芳基或經取代或未經取代的C6到C20芳氧基， 限制條件為R¹ 到R¹⁶ 中的至少一個由化學式2表示， [化學式2]

在化學式2中， R¹⁷ 和R¹⁸ 獨立地是鹵素原子， n1和n2獨立地是0到5範圍內的整數，且1≤n1+n2≤5。One embodiment provides a compound represented by Chemical Formula 1. [Chemical Formula 1]

In Chemical Formula 1, R ¹ to R ^{16 are} independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, substituted or not a substituted C6 to C20 aryl group or a substituted or unsubstituted C6 to C20 aryloxy group, with the constraint that at least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2, [Chemical Formula 2]

In Chemical Formula 2, R ¹⁷ and R ^{18 are} independently a halogen atom, and n1 and n2 are independently an integer in the range of 0 to 5, and 1 ≤ n1 + n2 ≤ 5.

The compound represented by Chemical Formula 1 has excellent green spectral characteristics and a high molar extinction coefficient. Further, during application to the color filter, the compound represented by Chemical Formula 1 has excellent solubility and excellent brightness and contrast ratio in an organic solvent by, if necessary, a substituent represented by Chemical Formula 2.

[化學式3-2]

[化學式3-3]

[化學式3-4]

其中，在化學式3-1到化學式3-4中， R¹⁷ 和R¹⁸ 獨立地是鹵素原子。Chemical Formula 2 can be represented by one selected from Chemical Formula 3-1 to Chemical Formula 3-4. [Chemical Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Chemical Formula 3-4]

Among them, in Chemical Formula 3-1 to Chemical Formula 3-4, R ¹⁷ and R ^{18 are} independently a halogen atom.

The substituent represented by Chemical Formulas 3-1 to 3-4 is an aryloxy group substituted with at least one halogen atom, and when at least one halogen atom is substituted, especially at the ortho and/or para position, brightness and The ratio can be further improved. In addition, when a halogen atom is substituted in the ortho and para positions (two halogen atoms are substituted), the luminance and the contrast ratio may be substituted with the halogen atom only in the ortho or para position (substitution of a halogen atom). Better than greater. However, when the halogen atom is substituted at a meta position (even if another halogen atom is substituted in the ortho and/or para position), the brightness and contrast ratio improvement may not be significant.

In other words, among the substituents represented by Chemical Formula 2, for example, in the substituents represented by Chemical Formulas 3-1 to 3-4, the luminance and the contrast ratio can be improved in the following order (i → ii → iii); i) At least one halogen atom is substituted at the meta position, ii) the halogen atom is substituted at the ortho or para position, and iii) the halogen is substituted at both the ortho and para positions.

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

For example, the substituent represented by Chemical Formula 4 can be represented by Chemical Formula 4-1. [Chemical Formula 4-1]

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

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 4, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 4, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4.

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 4, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 4, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4, and may not be The remainder represented by Chemical Formula 2 and Chemical Formula 4 may both be a halogen atom.

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

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 2, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 4, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4.

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 2, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 4, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4, and may not be The remainder represented by Chemical Formula 2 and Chemical Formula 4 may both be a halogen atom.

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

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 4, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 2, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4.

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 4, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 2, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4, and may not be The remainder represented by Chemical Formula 2 and Chemical Formula 4 may both be a halogen atom.

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

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 2, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 2, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4.

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 2, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 2, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 4, and may not be The remainder represented by Chemical Formula 2 and Chemical Formula 4 may both be a halogen atom.

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

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 2, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 2, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 2.

For example, R ² or R ³ may be represented by Chemical Formula 2, R ⁶ or R ⁷ may be represented by Chemical Formula 2, R ¹⁰ or R ¹¹ may be represented by Chemical Formula 2, and R ¹⁴ or R ¹⁵ may be represented by Chemical Formula 2, and may not be The remainder represented by Chemical Formula 2 may be a halogen atom.

[化學式6]

[化學式7]

[化學式8]

[化學式9]

[化學式10]

[化學式11]

[化學式12]

[化學式13]

[化學式14]

For example, the compound represented by Chemical Formula 1 may be represented by one of Chemical Formula 5 to Chemical Formula 14, but is not limited thereto. [Chemical Formula 5]

[Chemical Formula 6]

[Chemical Formula 7]

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical Formula 10]

[Chemical Formula 11]

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

The compound according to one embodiment can exhibit a clear color even in a small amount, and when used as a colorant, can be produced by including a substituent represented by Chemical Formula 2, for example, one of Chemical Formula 3-1 to Chemical Formula 3-4. A display device having excellent color characteristics such as brightness, contrast ratio, and the like. For example, the compound can be a color former 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 addition, the green dye may be a dye having a maximum absorbance in the wavelength range of 600 nm to 730 nm.

In general, dyes are the most expensive of the components used in color filters. Therefore, the expensive dyes may need more to achieve desired effects, such as high brightness, high contrast, etc. and thus increase the unit cost of production. However, when a compound according to one embodiment is used as a colorant, such as a dye in a color filter, the compound and/or polymer can achieve improved color characteristics (such as high brightness or high pair even with a small amount of use). Ratio) and reduce unit production costs.

According to another embodiment, the photosensitive resin composition comprises a compound according to one embodiment.

For example, the photosensitive resin composition contains: a coloring agent containing a compound according to the embodiment; a binder resin; a photopolymerizable compound; a photopolymerization initiator; and a solvent.

Each component is specifically described below. Colorant

The colorant may comprise a compound according to the examples.

The colorant may further comprise a green pigment and/or a yellow pigment.

For example, the colorant may include a compound represented by Chemical Formula 1, a green pigment dispersion, and a yellow pigment dispersion, and the compound represented by Chemical Formula 1 may necessarily contain a substituent represented by Chemical Formula 2.

Because the green dye has the highest transmittance in the 445 nm to 560 nm wavelength range and the maximum absorbance in the 600 nm to 730 nm wavelength range, when the green dye is used as a colorant together with the green pigment dispersion and the yellow pigment dispersion , achieves higher color coordinates, and can improve shading characteristics, brightness, and contrast ratio.

The colorant may include a compound represented by Chemical Formula 1, a green pigment dispersion, and a yellow pigment dispersion in an amount of from 1% by weight to 10% by weight (for example, from 3% by weight to 7% by weight) based on the total amount of the coloring agent, 60% by weight to 70% by weight and 20% by weight to 30% by weight. When the compound represented by Chemical Formula 1, the green pigment dispersion, and the yellow pigment dispersion in the amount range are contained in the colorant, a coloring agent having improved coloring characteristics can be realized, and also improved brightness and Contrast color filter.

For example, the green pigment in the green pigment dispersion may be C.I. Pigment Green 58, C.I. Pigment Green 59 or the like in the color index, which may be used singly or in the form of a mixture of two or more. Further, the yellow pigment in the yellow pigment dispersion may be C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment Yellow 150 or the like in a color index, which may be used singly or in the form of a mixture of two or more.

The lower the baseline in the above wavelength range, the higher the transmittance (brightness) is obtained in the higher color region. For absorption peaks occurring between 600 nm and 730 nm, higher peaks indicate higher color intensity, and herein, the dyes of the present invention show peaks about 1.5 times higher and therefore have CI Pigment Green 58 and CI Pigments Green 59 has a higher color intensity. In other words, when the dye of the present invention is used together with C.I. Pigment Green 58, C.I. Pigment Green 59, C.I. Pigment Yellow 138, etc., higher color coordinates can be achieved.

In general, dyes are the most expensive of the components used in color filters. Therefore, in order to achieve desired effects such as high brightness, high contrast ratio, etc., more expensive dyes should be used and thus unit manufacturing costs may be increased. However, when the compound of one embodiment is used as a dye in a color filter, the dye can achieve excellent color characteristics even in a small amount thereof, such as high brightness, high contrast ratio, and the like and thus lower unit manufacturing cost.

Green pigments and/or yellow pigments can be used with the dispersing agent to disperse the pigment. Specifically, the pigment may be pretreated with a dispersant on the surface or a pigment may be added to prepare a composition.

The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant or the like. Specific examples of the dispersant may be a polyolefin diol and an ester thereof, a polyoxyalkylene, a polyol ester alkylene oxide addition product, an alcohol alkylene oxide addition product, a sulfonate, a sulfonate, a carboxylate, a carboxylic acid A salt, an alkylguanamine alkylene oxide addition product, an alkylamine or the like, and may be used singly or in the form of a mixture of two or more.

Commercially available examples of dispersants may include DISPERBYK-101, Desbike-130, Desbike-140, Diss, manufactured by BYK Co., Ltd.克-160, dissip-161, dissip-162, dissip-163, dissip-164, dissip-165, dissip-166, dissick -170, Desbike-171, Desbike-182, Dissick-2000, Dissick-2001, etc.; Evka manufactured by EFKA Chemicals Co. (EFKA)-47, Evka-47EA, Evka-48, Evka-49, Evka-100, Evka-400, Evka-450, etc.; by Zeneka Co.) manufactured by Solsperse 5000, Sospers 12000, Sospos 13240, Sospos 13940, Sospos 17000, Sospos 20,000, Sospos 24000GR, Sospos 27000, Sos Persian 28000, etc.; or PB711, PB821 manufactured by Ajinomoto Inc.

The dispersant may be included in an amount of from 0.1% by weight to 15% by weight based on the total amount of the photosensitive resin composition. When the dispersant in the range is included, the composition has excellent stability, developability, and pattern forming ability due to improved dispersion characteristics during the production of the black column spacer.

The pigment can be pretreated with a water soluble inorganic salt and a wetting agent. When the pigment is pretreated, the average particle diameter of the pigment can become finer.

The pretreatment can be carried out by kneading the pigment with a water-soluble inorganic salt and a wetting agent, and then filtering and washing the kneaded pigment.

Kneading can be carried out at a temperature of from 40 ° C to 100 ° C, and filtration and washing can be carried out by filtering the pigment after washing off the inorganic salt with water or the like.

Examples of the water-soluble inorganic salt may be sodium chloride, potassium chloride or the like, but are not limited thereto. The humectant allows the pigment to be uniformly mixed with the water-soluble inorganic salt and pulverized. Examples of the humectant include an alkylene glycol monoalkyl ether such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, and the like; and an alcohol such as ethanol, isopropanol, butanol, hexanol, Cyclohexanol, ethylene glycol, diethylene glycol, polyethylene glycol, glycerol polyethylene glycol, and the like. These may be used singly or in the form of a mixture of two or more.

The pigment may have an average particle diameter in the range of from about 5 nm to about 200 nm, for example from about 5 nm to about 150 nm, after kneading. When the pigment has an average particle diameter within the range, the stability of the pigment dispersion can be improved and the pixel resolution may not deteriorate.

The solvent used to form the pigment dispersion may be ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether or the like.

Specifically, the pigment may be used in the form of a pigment dispersion liquid of a dispersant and a solvent which will be described later, and the pigment dispersion liquid may contain a solid pigment, a dispersant, and a solvent. The solid pigment may be included in an amount of 5 to 20% by weight, for example, 8 to 15% by weight, based on the total amount of the pigment dispersion.

The pigment dispersion may be contained in an amount of 10% by weight to 20% by weight, for example, 12% by weight to 18% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion in the range is included, the coloring effect, developing performance, and contrast ratio can be improved. Adhesive resin

The binder resin may comprise an acryl-based binder resin.

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

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

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

The diene unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, vinylbenzyl methyl ether or the like; an unsaturated carboxylic acid ester compound such as (A) Methyl acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzene (meth) acrylate Methyl ester, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, etc.; aminoalkyl ester compound of unsaturated carboxylic acid, such as 2-aminoethyl (meth)acrylate, 2-(meth)acrylic acid Dimethylaminoethyl ester or the like; a vinyl carboxylate compound such as vinyl acetate, vinyl benzoate or the like; an unsaturated carboxylic acid glycidyl ester compound such as glycidyl (meth)acrylate; an alkyl cyanide compound; For example, (meth)acrylonitrile or the like; an unsaturated guanamine compound such as (meth) acrylamide or the like; and the like, and may be used singly or in the form of a mixture of two or more.

Specific examples of the acrylonitrile-based binder resin may be a polybenzyl methacrylate copolymer, an acrylic acid/benzyl methacrylate copolymer, a methacrylic acid/benzyl methacrylate copolymer, or a methacrylic acid. /Methyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene / nail 2-hydroxyethyl acrylate copolymer or the like, but is not limited thereto. These may be used singly or in the form of a mixture of two or more.

The binder resin may have a weight average molecular weight of from 3,000 g/m to 150,000 g/mole, such as from 5,000 g/m to 50,000 g/mole, for example from 20,000 g/m to 30,000 g/mole. When the binder resin has a weight average molecular weight within the range, the photosensitive resin composition has good physical and chemical characteristics, appropriate viscosity, and close contact with the substrate during the production of the color filter.

The binder resin may be included in an amount of from 1% by weight to 30% by weight, for example, from 1% by weight to 20% by weight, based on the total amount of the photosensitive resin composition. When the binder resin within the above range is included, the developability can be improved and the excellent surface smoothness can be improved due to the improved crosslinking during the production of the color filter. Photopolymerizable compound

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

Due to the ethylenically unsaturated double bond, the photopolymerizable compound can cause sufficient polymerization during pattern formation, during exposure, and form a pattern having excellent heat resistance, light resistance, and chemical resistance.

Specific examples of the photopolymerizable compound may be ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, di(meth)acrylic acid. Propylene glycol ester, neopentyl glycol di(meth)acrylate, 1,4-butylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di Methyl) acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate Ester, dipentaerythritol tris(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy resin (meth) acrylate, ethylene glycol monomethyl Ethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris(meth) propylene methoxyethyl phosphate, phenolic epoxy (meth) acrylate, and the like.

Commercially available examples of photopolymerizable compounds can be as follows. The monofunctional (meth) acrylate may comprise Aronix M-101 ^® , M-111 ^® , M-114 ^® (Toagosei Chemistry Industry Co., Ltd.); KAYARAD TC-110S ^® , TC-120S ^® (Nippon Kayaku Co., Ltd.; V-158 ^® , V-2311 ^® (Osaka Organic) Chemical Ind., Ltd.)), etc. Examples of bifunctional (meth) acrylates may include Anix M-210 ^® , M-240 ^® , M-6200 ^® (East Asia Synthetic Chemical Industry Co., Ltd.), cards Arad HDDA ^® , HX-220 ^® , R-604 ^® (Nippon Chemical Co., Ltd.), V-260 ^® , V-312 ^® , V-335 HP ^® (Osaka Organic Chemical Industry Co., Ltd.), etc. (meth) acrylates may include Phoenix Ani ^{M-309 ®, M-400} ®, M-405 ®, M-450 ®, M-7100 ®, M-8030 ®, M-8060 ® ( Toagosei Chemical Industry Co., Ltd.; Kayarad TPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Chemical Co., Ltd.) ;V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Yuki Kayaku Kogyo Co. Ltd.) These may be used singly or in the form of a mixture of two or more.

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

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

The photopolymerization initiator may be a photopolymerization initiator commonly used in the photosensitive resin composition, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, an anthraquinone compound, or the like.

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

Examples of the benzophenone compound may be benzophenone, benzamidine benzoate, methyl benzylidenebenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone Ketone, 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 compound may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-chlorothioxanthone and the like.

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

Examples of the triazine compound may be 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3', 4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloro) Methyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis ( Trichloromethyl)-s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-three Pyrazine, 2-(naphthol 1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthol-1-yl)-4,6-bis ( Trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-silveryl-s-triazine, 2-4-bis(trichloromethyl)-6-(4- Methoxystyryl)-s-triazine and the like.

Examples of the quinone compound may be an O-quinone compound, 2-(O-benzylidene fluorenyl)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1- (O-acetamidine)-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxygen Amino-1-phenylpropan-1-one and the like. A specific example of the O-quinone compound may be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-benzene -butan-1-one, 1-(4-phenylthiophenyl)-butyl-1,2-dione 2-indole-O-benzoate, 1-(4-phenylthiophenyl) )-octane-1,2-dione 2-indole-O-benzoate, 1-(4-phenylthiophenyl)-oct-1-one oxime-O-acetate, 1-( 4-phenylthiophenyl)-butan-1-one oxime-O-acetate or the like.

In addition to the compound, the photopolymerization initiator may further contain a carbazole compound, a diketone compound, a lanthanum borate compound, a diazo compound, an imidazole compound, a biimidazole compound, an anthraquinone compound, or the like.

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

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

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

The solvent is a material which is compatible with, but does not react with, the compound, the pigment, the binder resin, the photopolymerizable compound, and the photopolymerization initiator according to one embodiment.

Examples of the solvent may include an alcohol such as methanol, ethanol, etc.; an ether such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl ether, tetrahydrofuran or the like; a glycol ether such as ethylene glycol monomethyl ether, B Glycol monoethyl ether, etc.; ethylene glycol ethyl ether, such as methyl glycol acetate diethyl ether, ethyl glycol ethyl acetate diethyl ether, diethyl glycol acetate ethyl ether, etc.; carbitol, such as methyl ethyl Kikabiol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, etc.; Propylene glycol alkyl ether acetate, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 4- Hydroxy-4-methyl-2-pentanone, methyl n-acetone, methyl n-butanone, methyl n-pentanone, 2-heptanone, etc.; a saturated aliphatic monocarboxylic acid alkyl ester such as ethyl acetate, N-butyl acetate, isobutyl acetate, etc.; lactate esters, such as methyl lactate, ethyl lactate, etc.; alkyl oxyacetate, such as methyl oxyacetate, ethyl oxyacetate, oxygen Butyl acetate and the like; alkyl alkoxyacetate such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.; An alkyl 3-oxopropionate such as methyl 3-oxypropionate, ethyl 3-oxypropionate or the like; an alkyl 3-alkoxypropionate such as 3-methoxypropionic acid Ester, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; alkyl 2-oxopropionate, such as 2-oxypropionic acid Methyl ester, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate, 2-methoxypropane Ethyl acetate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxy-2-methylpropionate, such as 2-oxy-2-methylpropionic acid Methyl ester, ethyl 2-oxy-2-methylpropionate, etc.; alkyl 2-alkoxy-2-methylpropanoate of monooxymonocarboxylic acid alkyl ester, such as 2-methoxy Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, Hydroxyethyl acetate, 2-hydroxy-3-methylmethyl butyrate, etc.; keto acid , Such as acetone and ethyl. In addition, high boiling solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformamide, N-methylacetamide, N,N-di can also be used. Methylacetamide, N-methylpyrrolidone, dimethyl hydrazine, benzyl ether, dihexyl ether, acetamidine, isophorone, caproic acid, octanoic acid, 1-octanol, 1- Sterol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, ethylene glycol ether Phenyl acetate and the like.

In view of miscibility and reactivity, a glycol ether such as ethylene glycol monoethyl ether or the like; an ethylene glycol alkyl ether acetate such as ethyl glycol acetate diethyl ether or the like; an ester such as propionic acid 2 can be preferably used. - hydroxyethyl ester, etc.; carbitol, such as diethylene glycol monomethyl ether; propylene glycol alkyl ether acetate, such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, etc.; and ketones, such as rings Hexanone.

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

The photosensitive resin composition according to one embodiment may further contain other additives such as malonic acid; 3-amino-1,2-propanediol; a decane coupling agent containing a vinyl group or a (meth) acryloxy group; A leveling agent; a surfactant; and a free radical polymerization initiator to prevent stains or spots during coating, thereby adjusting the leveling, or preventing pattern residues due to undeveloped.

The additive can be controlled depending on the desired characteristics.

The coupling agent may be a decane type coupling agent, and examples of the decane type coupling agent may be trimethoxy decyl benzoic acid, γ-methyl propylene decyl propoxy trimethoxy decane, vinyl triethoxy decyl hydride, Vinyl trimethoxy decane, γ-isocyanate propyl triethoxy decane, γ-glycidoxypropyl trimethoxy decane, β-(3,4-epoxycyclohexyl)ethyltrimethoxy decane Wait. These may be used singly or in the form of a mixture of two or more.

The decane coupling agent may be contained in an amount of from 0.01 part by weight to 10 parts by weight based on the total amount of the photosensitive resin composition.

Further, the photosensitive resin composition for a color filter may further contain a surfactant such as a fluorine-based surfactant.

Examples of the fluorine-based surfactant may include F-482, F-484, F-478, and the like manufactured by DIC Co., Ltd., but are not limited thereto.

The surfactant may be included in an amount of from 0.001% by weight to 5% by weight, preferably from 0.01% by weight to 2% by weight, based on the total amount of the photosensitive resin composition. When the amount is outside the range, foreign particles after development may be generated.

The photosensitive resin composition according to one embodiment may further contain an epoxy compound to improve adhesion to a substrate.

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

The epoxy compound may be included in an amount of from 0.01 part by weight to 20 parts by weight, for example, from 0.1 part by weight to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the amount is within the range, adhesion and storage can be enhanced.

Further, the photosensitive resin composition may contain a predetermined amount of other additives such as an antioxidant, a stabilizer, etc., unless the additive deteriorates the characteristics of the photosensitive resin composition.

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

The method of manufacturing a color filter is as follows.

The photosensitive resin composition is coated on a glass substrate by a suitable method such as spin coating, roll coating, spray coating or the like to form a photosensitive resin composition layer of 0.5 μm to 10 μm thick.

Subsequently, the substrate having the photosensitive resin composition layer is irradiated with light to form a desired pattern of the color filter. The radiation can be carried out by using UV, electron beam or X-ray as the light source, and the UV can be radiated, for example, in the region of 190 nm to 450 nm, and especially 200 nm to 400 nm. Radiation can be performed by further using a photoresist mask. After the irradiation process is performed in this manner, the photosensitive resin composition layer exposed to the light source is treated with a developer. Herein, the non-exposed regions in the photosensitive resin composition layer dissolve and form a pattern of color filters. This process can be repeated as many times as the desired number of colors to obtain a color filter having the desired pattern. In addition, when the image pattern obtained by the development in the above method is cured by reheating or irradiating the actinic radiation thereto, crack resistance, solvent resistance, and the like can be improved.

In the following, the invention will be described in more detail with reference to examples, however, these examples are not to be construed as limiting the scope of the invention. (Synthesis of Compound a) Synthesis Example 1: Synthesis of 4- (biphenyl-2-yloxy) -3,5,6-trichloro - phthalonitrile

5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.21 g of 2-phenylphenol, 3.9 g of K ₂ CO ₃ and 25 ml of acetone were placed in a 100 ml flask and then stirred while Heat at 70 °C. When the reaction was completed, the resultant was filtered and washed with acetone, and the liquid obtained therefrom was distilled to obtain a solid. Herein, the obtained solid is dissolved in a small amount of dichloromethane, and then washed several times with hexane, filtered and dried under vacuum to obtain 4-(biphenyl-2-yloxy)-3,5,6 - Trichloro-phthalonitrile. Synthesis Example 2 : Synthesis of 3,4,6- trichloro -5-(2,6- dichloro - phenoxy ) -phthalonitrile

5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.06 g of 2,6-dichlorophenol, 3.9 g of K ₂ CO ₃ and 25 ml of acetone were placed in a 100 ml flask, followed by stirring. At the same time, it was heated at 70 °C. When the reaction was completed, the resultant was filtered and washed with acetone, and the liquid obtained therefrom was distilled to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane and then washed several times with hexane, filtered and dried in vacuo to give 3,4,6-trichloro-5-(2,6-dichloro -phenoxy)-phthalonitrile. Synthesis Example 3 : Synthesis of 3,4,6- trichloro -5-(2,6 -dibromo - phenoxy ) -phthalonitrile

Place 5 g of 3,4,5,6-tetrachlorophthalonitrile, 4.75 g of 2,6-dibromophenol, 3.9 g of K ₂ CO ₃ and 25 ml of N,N-dimethylformamide In a 100 ml flask, stir while heating at 70 °C. When the reaction was completed, EA (ethyl acetate) was used for extraction. After the extraction, the resultant was concentrated to obtain a solid. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to give 3,4,6-trichloro-5-(2,6-dibromo-phenoxy)- Phthalic nitrile. Synthesis Example 4 : Synthesis of 3,4,6- trichloro -5-(2,6 -difluoro - phenoxy ) -phthalonitrile

Place 5 g of 3,4,5,6-tetrachlorophthalonitrile, 2.45 g of 2,6-difluorophenol, 3.9 g of K ₂ CO ₃ and 25 ml of N,N-dimethylformamide In a 100 ml flask, and then stirred while heating at 70 °C. When the reaction was completed, EA (ethyl acetate) was used for extraction. After the extraction, the resultant was concentrated to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane and then washed several times with hexane, filtered and dried in vacuo to give 3,4,6-trichloro-5-(2,6-difluoro -phenoxy)-phthalonitrile. Synthesis Example 5 : Synthesis of 3,4,6- trichloro -5-(2- chloro - phenoxy ) -phthalonitrile

5 g of 3,4,5,6-tetrachlorophthalonitrile, 2.41 g of 2-chlorophenol, 3.9 g of K ₂ CO ₃ and 25 ml of acetone were placed in a 100 ml flask and then stirred while at 70 Heat at °C. When the reaction was completed, the resultant was filtered and washed with acetone, and the liquid obtained therefrom was distilled to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and then dried in vacuo to give 3,4,6-trichloro-5-(2-chloro-phenoxy) )-phthalonitrile. Synthesis Example 6 : Synthesis of 3,4,6- trichloro -5-(2- bromo - phenoxy ) -phthalonitrile

5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.25 g of 2-bromophenol, 3.9 g of K ₂ CO ₃ and 25 ml of N,N-dimethylformamide were placed in a 100 ml flask Medium, and then stirred while heating at 70 °C. When the reaction was completed, EA (ethyl acetate) was used for extraction. After the extraction, the resultant was concentrated to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to give 3,4,6-trichloro-5-(2-bromo-phenoxy) - phthalonitrile. Synthesis Example 7 : Synthesis of 3,4,6- trichloro -5-(2- fluoro - phenoxy ) -phthalonitrile

5 g of 3,4,5,6-tetrachlorophthalonitrile, 2.10 g of 2-fluorophenol, 3.9 g of K ₂ CO ₃ and 25 ml of N,N-dimethylformamide were placed in a 100 ml flask Medium, and then stirred while heating at 70 °C. When the reaction was completed, EA (ethyl acetate) was used for extraction. After the extraction, the resultant was concentrated to obtain a solid. The obtained solid was dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to give 3,4,6-trichloro-5-(2-fluoro-phenoxy)-phthalic acid Formonitrile. Synthesis Example 8 : Synthesis of 3,4,6- trichloro -5-(2,5- dichloro - phenoxy ) -phthalonitrile

5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.06 g of 2,5-dichlorophenol, 3.9 g of K ₂ CO ₃ and 25 ml of acetone were placed in a 100 ml flask and then stirred. At the same time, it was heated at 70 °C. When the reaction was completed, the resultant was filtered and washed with acetone, and the liquid obtained therefrom was distilled to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to give 3,4,6-trichloro-5-(2,5-dichloro-benzene. Oxy)-phthalonitrile. Synthesis Example 9 : Synthesis of a compound represented by Chemical Formula 5

1.5 g of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile of Synthesis Example 1, 0.49 g of 3,4,6-trichloro- of Synthesis Example 2 5-(2,6-Dichloro-phenoxy)-phthalonitrile, 1.52 g of 1,8-diazabicyclo undec-7-ene and 14 g of 1-pentenol were placed in a 100 ml flask Medium, and then heated at 90 ° C, after the solid was dissolved, 0.23 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 5. [Chemical Formula 5]

Maldi-tof MS: 1656.79 m/z Synthesis Example 10 : Synthesis of a compound represented by Chemical Formula 6

1.6 g of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile according to Synthesis Example 1, 1.5 g of 3, 4, 6-three according to Synthesis Example 2. Chloro-5-(2,6-dichloro-phenoxy)-phthalonitrile, 1.74 g of 1,8-diazabicyclo undec-7-ene and 14 g of 1-pentenol were placed at 100 In a milliliter flask, and heated at 90 ° C, after the solid was dissolved, 0.34 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 6. [Chemical Formula 6]

Maldi-tof MS: 1649.57 m/z Synthesis Example 11 : Synthesis of a compound represented by Chemical Formula 7

1 g of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile, 2.9 g of Synthesis Example 2, 3,4,6-trichloro- 5-(2,6-Dichloro-phenoxy)-phthalonitrile, 3 g of 1,8-diazabicyclo undec-7-ene and 27 g of 1-pentenol were placed in a 100 ml flask While heating at 90 ° C, after the solid was dissolved, 0.45 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 7. [Chemical Formula 7]

Maldi-tof MS: 1642.36 m/z Synthesis Example 12: Synthesis of a compound represented by Chemical Formula 8

1.5 g of Synthesis Example 2 of 3,4,6-trichloro-5-(2,6-dichloro-phenoxy)-phthalonitrile, 0.87 g of 1,8-diazabicyclo-11 7-ene and 7 g of 1-pentenol were placed in a 100 ml flask, and then heated at 90 ° C. After the solid was dissolved, 0.17 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 8. [Chemical Formula 8]

Maldi-tof MS: 1635.14 m/z Synthesis Example 13 : Synthesis of a compound represented by Chemical Formula 9

1.5 g of Synthesis Example 3 of 3,4,6-trichloro-5-(2,6-dibromo-phenoxy)-phthalonitrile, 0.87 g of 1,8-diazabicyclo-11 7-ene and 7 g of 1-pentenol were placed in a 100 ml flask, and then heated at 90 ° C. After the solid was dissolved, 0.17 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid, and methanol was used for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 9. [Chemical Formula 9]

Maldi-tof MS: 1990.78 m/z Synthesis Example 14 : Synthesis of a compound represented by Chemical Formula 10

1.5 g of Synthesis Example 4 of 3,4,6-trichloro-5-(2,6-difluoro-phenoxy)-phthalonitrile, 0.87 g of 1,8-diazabicyclo-11 7-ene and 7 g of 1-pentenol were placed in a 100 ml flask and heated at 90 ° C. After the solid was dissolved, 0.17 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 10. [Chemical Formula 10]

Maldi-tof MS: 1503.53 m/z Synthesis Example 15 : Synthesis of a compound represented by Chemical Formula 11

1.5 g of Synthesis Example 5 of 3,4,6-trichloro-5-(2-chloro-phenoxy)-phthalonitrile, 0.87 g of 1,8-diazabicycloundec-7-ene And 7 g of 1-pentenol was placed in a 100 ml flask and heated at 90 ° C. After the solid was dissolved, 0.17 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 11. [Chemical Formula 11]

Maldi-tof MS: 1497.38 m/z Synthesis Example 16 : Synthesis of a compound represented by Chemical Formula 12

1.5 g of Synthesis Example 6 of 3,4,6-trichloro-5-(2-bromo-phenoxy)-phthalonitrile, 0.87 g of 1,8-diazabicycloundec-7-ene And 7 g of 1-pentenol was placed in a 100 ml flask and heated at 90 ° C. After the solid was dissolved, 0.17 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 12. [Chemical Formula 12]

Maldi-tof MS: 1675.19 m/z Synthesis Example 17 : Synthesis of a compound represented by Chemical Formula 13

1.5 g of Synthesis Example 7 of 3,4,6-trichloro-5-(2-fluoro-phenoxy)-phthalonitrile, 0.87 g of 1,8-diazabicycloundec-7-ene And 7 g of 1-pentenol was placed in a 100 ml flask and heated at 90 ° C. After the solid was dissolved, 0.17 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 °C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 13. [Chemical Formula 13]

Maldi-tof MS: 1435.57 m/z Synthesis Example 18 : Synthesis of a compound represented by Chemical Formula 14

1.6 g of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile of 1.5, and 1.5 g of 3,4,6-trichloro of Synthesis Example 8 were added. 5-(2,5-Dichloro-phenoxy)-phthalonitrile, 1.74 g of 1,8-diazabicyclo undec-7-ene and 14 g of 1-pentenol were placed in a 100 ml flask The mixture was heated at 90 ° C, and after the solid was dissolved, 0.34 g of zinc acetate was added thereto, and the mixture was stirred while heating at 140 ° C. When the reaction was completed, methanol was used for precipitation, and the precipitate obtained therefrom was filtered and dried under vacuum. The dried solid was purified by column chromatography. Next, dichloromethane was appropriately added to the purified solid to dissolve it, and methanol was added thereto for crystallization. The crystalline solid was filtered and dried under vacuum to obtain a compound represented by Chemical Formula 14. [Chemical Formula 14]

Maldi-tof MS: 1649.57 m/z Comparative Synthesis Example 1 : Synthesis of a compound represented by Chemical Formula X

1 g of 4-(2-sec-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile, 0.30 g of 1,8-diazabicyclo undec-7-ene, 7 Gram 1-pentenol and 0.12 g of zinc acetate were placed in a 100 ml flask and stirred while heating at 140 °C. When the reaction was completed, the resultant was concentrated and purified by column chromatography. The purified liquid was concentrated to obtain a solid. The crystalline solid was dried under vacuum to obtain the compound represented by the formula X. [Chemical Formula X]

Maldi-tof MS: 1584.04 m/z ( Synthesis of photosensitive resin composition ) Example 1

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

實例 2 Specifically, the photopolymerization initiator was dissolved in a solvent, and the solution was stirred at room temperature for 2 hours, a binder resin and a photopolymerizable compound were added thereto, and the mixture was stirred at room temperature for 2 hours. Subsequently, the compound of Synthesis Example 9 (represented by Chemical Formula 5) and the pigment as a coloring agent (in the state in which the pigment was dispersed) were added to the reactant, and the mixture was stirred at room temperature for 1 hour. Next, the product obtained therefrom was filtered three times to remove impurities, thereby preparing a photosensitive resin composition. [Table 1] (Unit: % by weight)

Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 10 (represented by Chemical Formula 6) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 7) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 8) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 9) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 10) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 11) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 12) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 13) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 14) was used instead of the compound of Synthesis Example 9 (represented by Chemical Formula 5). Example 11

In place of 3.7 wt% dye instead of 5% by weight dye, "2.5 wt% pigment G58 pigment dispersion and 13.7% by weight pigment Y138 pigment dispersion" was used instead of "15.0 wt% pigment Y138 pigment dispersion", and 30.1 wt% PGMEA was used. A photosensitive resin composition was prepared in the same manner as in Example 1 except that 30.0% by weight of PGMEA was used. Example 12

A photosensitive resin composition was prepared in the same manner as in Example 11 except that the compound of Synthesis Example 10 (represented by Chemical Formula 6) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 7) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 8) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 9) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 10) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 11) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 12) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 13) was used instead of the compound of Synthesis Example 9 (represented by Chemical 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 (represented by Chemical Formula 14) was used instead of the compound of Synthesis Example 9 (represented by Chemical Formula 5). Comparative example 1

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Comparative Synthesis Example 1 (represented by Chemical Formula X) was used instead of the compound of Synthesis Example 9 (represented by Chemical Formula 5). Comparative example 2

評估 1 ： 評估亮度和對比率 A photosensitive resin composition was prepared in the same manner as in Example 1 except that the following composition in Table 2 was used instead of the composition in Table 1. [Table 2] (Unit: % by weight)

Assessment 1 : Evaluate Brightness and Contrast Ratio

The photosensitive resin compositions according to Examples 1 to 20 and Comparative Examples 1 and 2 were respectively coated on a degreased glass substrate of 1 μm to 3 μm thick to 1 mm thick, and then dried on a hot plate at 90 ° C for 2 minutes to obtain membrane. The membrane was exposed by using a high pressure mercury lamp with a dominant wavelength of 365 nm. Subsequently, the film was dried in a forced convection drying boiler at 200 ° C for 5 minutes to obtain a sample. The luminance (Y) of the pixel layer and the contrast ratio were measured by using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are shown in Table 3. [table 3]

Referring to Table 3, compared with the photosensitive resin compositions of Comparative Examples 1 and 2, the photosensitive resin compositions of Examples 1 to 20 containing the compound according to one example as a dye, especially the photosensitive resin compositions of Examples 1 to 9 The object shows excellent color characteristics.

Although the present invention has been described in connection with what is presently considered as a practical example embodiment, it is understood that the invention is not limited to the disclosed embodiments, but rather, the invention is intended to cover the spirit and scope of the appended claims. Various modifications and equivalent configurations.

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Claims (17)

A compound represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R ¹ to R ^{16 are} independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, substituted or not a substituted C6 to C20 aryl group or a substituted or unsubstituted C6 to C20 aryloxy group, with the constraint that at least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2, [Chemical Formula 2] Wherein in Chemical Formula 2, R ¹⁷ and R ^{18 are} independently a halogen atom, n1 and n2 are independently an integer in the range of 0 to 5, and 1 ≤ n1 + n2 ≤ 5. The compound according to claim 1, wherein the chemical formula 2 is represented by one selected from the chemical formula 3-1 to the chemical formula 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] Wherein in Chemical Formula 3-1 to Chemical Formula 3-4, R ¹⁷ and R ^{18 are} independently a halogen atom. The compound according to item 1 of the scope of patent applications, in which R ¹ to R ^{16 is} at least one represented by Chemical Formula 2, R ¹⁶ to ¹ and R & lt least one represented by Chemical Formula 4: [Chemical Formula 4] . The compound according to claim 3, wherein at least one of R ¹ to R ¹⁶ is represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 4, and at least one of R ⁹ to R ¹² represented by chemical formula 4, R ¹³ to R ¹⁶ and at least one represented by chemical formula 4. The compound according to claim 3, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² It is represented by Chemical Formula 4, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 4. The compound according to claim 3, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 4, and at least one of R ⁹ to R ¹² It is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 4. The compound according to claim 3, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² It is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 4. The compound according to claim 1, wherein at least one of R ¹ to R ⁴ is represented by Chemical Formula 2, at least one of R ⁵ to R ⁸ is represented by Chemical Formula 2, and at least one of R ⁹ to R ¹² It is represented by Chemical Formula 2, and at least one of R ¹³ to R ¹⁶ is represented by Chemical Formula 2. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by one of Chemical Formula 5 to Chemical Formula 14: [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] . The compound of claim 1, wherein the compound is a green dye. The compound of claim 10, wherein the green dye has a maximum transmittance in a wavelength range from 445 nm to 560 nm. A photosensitive resin composition comprising the compound according to any one of claims 1 to 11. The photosensitive resin composition according to claim 12, wherein the photosensitive resin composition contains 1% by weight to 10% by weight of the compound based on the total amount of the photosensitive resin composition. The photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further comprises a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further contains a pigment. The photosensitive resin composition according to 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 as described in claim 12 of the patent application.