TW201700460A - Novel fat-soluble compound, photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

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

Description

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

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

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

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

Therefore, it is necessary to study a suitable compound (especially an auxiliary dye compound) as a dye for producing a photosensitive resin composition.

One embodiment provides a novel lipid soluble compound.

Another embodiment provides a photosensitive resin composition comprising the fat-soluble compound.

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

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

In Chemical Formula 1, R ¹ is a cyano group, and R ² is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkylene group or a substituted or unsubstituted C6 to C20 aryl, n is an integer in the range of 2 to 5, and m is an integer in the range of 0 to 5, with the constraint being 2 ≤ n+m ≤ 5, and A being substituted or unsubstituted a C6 to C20 aromatic heterocyclic ring or a substituted or unsubstituted C3 to C20 alicyclic heterocyclic ring.

The aromatic heterocyclic ring and the alicyclic heterocyclic ring may contain at least one structure represented by Chemical Formula 2 in the ring. [Chemical Formula 2]

The aromatic heterocyclic ring can be represented by Chemical Formula 3. [Chemical Formula 3]

In Chemical Formula 3, R ³ is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, and R ⁴ to R ^{6 are} independently hydrogen, cyano group, Hydroxyl, substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl.

In Chemical Formula 3, R ³ may be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, R ⁴ may be a cyano group, and R ⁵ may be substituted or not substituted C1 to C20 alkyl, or a substituted or unsubstituted C6 to C20 aryl group, and R ⁶ is hydroxy may be.

The alicyclic heterocyclic ring can be represented by Chemical Formula 4. [Chemical Formula 4]

In Chemical Formula 4, R ⁷ and R ^{8 are} independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

The fat-soluble compound represented by Chemical Formula 1 may be a compound represented by one of Chemical Formula 5 to Chemical Formula 9. [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

The fat soluble compound can be a yellow dye.

Still another embodiment provides a photosensitive resin composition comprising the fat-soluble compound.

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

The photosensitive resin composition may further contain a pigment.

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

The color filter can be a green filter or a red filter.

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

According to one embodiment, the fat-soluble compound has excellent yellow spectral characteristics, high molar extinction coefficient, and excellent solubility in an organic solvent, and can be used during preparation of a photosensitive resin composition for a color filter. The auxiliary dye, and thus the color filter comprising the auxiliary dye and in particular the green filter or the red filter, can have excellent brightness and excellent contrast ratio.

The invention will be described more fully hereinafter, in which exemplary embodiments of the invention are described. However, the invention may be embodied in many different forms and should not be construed as being limited to the exemplary embodiments set forth herein. These exemplary embodiments are disclosed in this specification so that the invention will satisfy the applicable legal requirements.

As used herein, when a specific definition is not otherwise provided, the term "substituted" refers to substitution with a substituent selected from 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 independently C1 to C10 alkyl), formazanyl , mercapto, fluorenyl, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alicyclic organic The group, the substituted or unsubstituted aryl group and the substituted or unsubstituted heterocyclic group replace the functional group of the present invention.

As used herein, the term "alkyl group" refers to a C1 to C20 alkyl group and, in particular, a C1 to C15 alkyl group, and the term "cycloalkyl group" means, unless a specific definition is otherwise provided. C3 to C20 cycloalkyl and, in particular, C3 to C18 cycloalkyl, the term "alkoxy group" means C1 to C20 alkoxy and, in particular, C1 to C18 alkoxy, the term "aryl" (aryl group) means a C6 to C20 aryl group and specifically a C6 to C18 aryl group, and the term "alkenyl group" means a C2 to C20 alkenyl group and specifically a C2 to C18 alkenyl group, the term " "alkylene group" means C1 to C20 alkyl and specifically C1 to C18 alkyl, and the term "arylene group" means C6 to C20 extended aryl and specifically C6 to C16 extend to an aryl group.

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

As used herein, the term "combination" refers to mixing or copolymerization when no definition is otherwise provided. Further, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means a block copolymer or a random copolymer.

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

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

Further, when no definition is provided in the specification, "maximum absorbance range" indicates the maximum absorbance.

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

In Chemical Formula 1, R ¹ is a cyano group, and R ² is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkylene group or a substituted or unsubstituted C6 to C20 aryl, n is an integer in the range of 2 to 5, and m is an integer in the range of 0 to 5, with the constraint being 2 ≤ n+m ≤ 5, and A being substituted or unsubstituted a C6 to C20 aromatic heterocyclic ring or a substituted or unsubstituted C3 to C20 alicyclic heterocyclic ring.

The fat-soluble compound according to one embodiment is represented by Chemical Formula 1, and since the benzene ring in Chemical Formula 1 must contain at least two cyano groups, the compound can have excellent contrast ratio and excellent brightness as well as maintenance and conventional knowledge. A similar wavelength for yellow dyes. Further, the fat-soluble compound has a wavelength similar to a conventional yellow pigment (such as yellow G or the like) or a shorter wavelength, high heat resistance and coloring property, and in an organic solvent such as cyclohexanone, PGMEA, or the like. Excellent solubility.

Further, the compound according to one embodiment is fat-soluble and thus highly soluble in an organic solvent and has a structure and use different from those of a compound containing a water-soluble substituent such as a sulfonic acid group or the like or a salt thereof.

For example, in Chemical Formula 1, n may be an integer of 2, and m is an integer of 0.

For example, the aromatic heterocyclic ring and the alicyclic heterocyclic ring may contain at least one structure represented by Chemical Formula 2 in the ring. [Chemical Formula 2]

For example, an aromatic heterocyclic ring can be represented by Chemical Formula 3. [Chemical Formula 3]

In Chemical Formula 3, R ³ is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl, or a substituted or unsubstituted C6 to C20 aryl group, and R ⁴ to R ⁶ are independently hydrogen, cyano a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

For example, the fat-soluble compound represented by Chemical Formula 1 can be represented by Chemical Formula 1-1. [Chemical Formula 1-1]

In Chemical Formula 1-1, R ¹ to R ⁶ , n and m are the same as described above.

For example, R ³ may be substituted or unsubstituted C1 to C20 alkyl or substituted or unsubstituted C6 to C20 aryl, R ⁴ may be cyano, and R ⁵ may be substituted or unsubstituted substituted C1 to C20 alkyl, or a substituted or unsubstituted C6 to C20 aryl group, and R ⁶ is hydroxy may be.

For example, an alicyclic heterocyclic ring can be represented by Chemical Formula 4. [Chemical Formula 4]

In Chemical Formula 4, R ⁷ and R ^{8 are} independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

For example, the fat-soluble compound represented by Chemical Formula 1 can be represented by Chemical Formula 1-2. [Chemical Formula 1-2]

In Chemical Formula 1-2, R ¹ , R ² , R ⁷ , R ⁸ , n and m are the same as described above.

The fat-soluble compound represented by Chemical Formula 1 contains an aromatic heterocyclic ring represented by Chemical Formula 3 or an alicyclic heterocyclic ring represented by Chemical Formula 4, and thus can be similar to a conventional yellow pigment, in addition to at least two cyano groups. It has a maximum absorbance area at wavelength or shorter wavelengths and excellent heat resistance and coloring properties.

For example, the fat-soluble compound represented by Chemical Formula 1 can be represented by one of Chemical Formula 5 to Chemical Formula 9. [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

The fat-soluble compound according to one embodiment is represented by Chemical Formula 1 (for example, Chemical Formula 1-1 or Chemical Formula 1-2), and thus when used as a colorant (for example, an auxiliary dye), it is possible to achieve clear color even in a small amount and provide a pole A display device that has good color characteristics such as brightness, contrast ratio, and the like. For example, the liposoluble compound can be a yellow dye, such as a dye having a maximum absorbance region at a wavelength ranging from 150 nm to 450 nm (eg, 350 nm to 450 nm).

For example, a fat-soluble compound represented by Chemical Formula 1-1 (in the Chemical Formula 1, A is an aromatic heterocyclic ring, the aromatic heterocyclic ring is represented by Chemical Formula 3) may be in a wavelength ranging from 400 nm to 450 nm. The fat-soluble compound represented by Chemical Formula 1-2 (in Chemical Formula 1, A is an alicyclic heterocyclic ring and the alicyclic heterocyclic ring is represented by Chemical Formula 4) can be in the range of 150 nm to 400 nm. The maximum absorbance region at wavelengths (eg, 350 nm to 400 nm).

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

According to one embodiment, a photosensitive resin composition comprising a fat-soluble compound according to one embodiment is provided.

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

The photosensitive resin composition may further contain a pigment.

The fat-soluble compound according to one embodiment functions as a coloring agent (for example, a dye such as a yellow auxiliary dye) in the photosensitive resin composition and can realize excellent color characteristics.

The fat-soluble compound according to one embodiment may be used 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 photosensitive resin composition. When a compound according to one embodiment is used within the range, excellent color reproducibility and an excellent contrast ratio can be obtained.

The pigment may include, but is not limited to, a yellow pigment, a green pigment, a red pigment, or a combination thereof. For example, the pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion.

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

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

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

Commercially available examples of the dispersing agent may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163 manufactured by BYK Co., Ltd. DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc.; EFKA-47 manufactured by EFKA Chemicals Co., EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc.; Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, manufactured by Zeneka Co., Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; or PB711, PB821, etc. manufactured by Ajinomoto Inc.

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

The solvent used for the pigment dispersion may be ethylene glycol acetate, ethylenecellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc. Etc., but not limited to this.

The pigment dispersion liquid may be contained in an amount of from 5% by weight to 30% by weight, for example, from 10% by weight to 25% by weight based on the total of the photosensitive resin composition. When the pigment dispersion liquid within the range is contained, the processing allowance can be favorably ensured and the color reproducibility and the contrast ratio become excellent.

The alkali-soluble resin may be an acrylic resin.

The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing at least one acrylic repeating unit.

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

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

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

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

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

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

The alkali-soluble resin may be contained in an amount of from 1% by weight to 30% by weight, for example, from 1% by weight to 15% by weight based on the total of the photosensitive resin composition for the color filter. When the alkali-soluble resin in the above range is contained, the developability can be improved and excellent surface smoothness can be improved due to improved crosslinking during the manufacture of the color filter.

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

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

Specific examples of the photopolymerizable compound may be ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(methyl). Acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A II Methyl) acrylate, pentaerythritol di(meth) acrylate, pentaerythritol tri(meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate Ester, dipentaerythritol tri(meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl Ether (meth) acrylate, trimethylolpropane tri(meth) acrylate, tris(meth) propylene methoxyethyl phosphate, phenol aldehyde epoxy (meth) acrylate, and the like.

Commercially available examples of photopolymerizable compounds are as follows. Examples of the (meth)acrylic monofunctional ester may include Aronix M-101 ^® , M-111 ^® , M-114 ^® (Toagosei Chemistry Industry Co., Ltd.); KAYARAD TC-110S ^® , TC-120S ^® (Nippon Kayaku Co., Ltd.); V-158 ^® , V-2311 ^® (Osaka Organic Chemical Ind., Ltd.), etc. . Examples of the (meth)acrylic difunctional ester may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (East Asia Synthetic Chemical Co., Ltd.); KAYARAD HDDA ^® , HX-220 ^® , R-604 ^® (Japan) Chemicals Co., Ltd.; V-260 ^® , V-312 ^® , V-335 HP ^® (Osaka Organic Chemical Co., Ltd.), etc. Examples of trifunctional esters of (meth)acrylic acid may include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-7100 ^® , M-8030 ^® , M-8060 ^® (East Asian Synthesis) Chemical Co., Ltd.; KAYARAD TMPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Chemical Co., Ltd.); V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Yuki Kayaku Kogyo Co. Ltd.) and so on. These may be used singly or in the form of a mixture of two or more.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Examples of the epoxy compound may be a phenol novolac epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A epoxy compound, an alicyclic epoxy compound, or a combination thereof.

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

The photosensitive resin composition may further contain a decane coupling agent having a reactive substituent such as a carboxyl group, a methacryl oxime group, an isocyanate group or an epoxy group to improve adhesion to a substrate.

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

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

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

Examples of surfactants may include lanthanide surfactants such as BM-1000 ^® and BM-1100 ^® (BM Chemie Inc.); MEGAFACE F 142D ^® , F 172 ^® , F 173 ^® and F 183 ^® (Dainippon Ink Kagaku Kogyo Co., Ltd.); FULORAD FC-135 ^® , FULORAD FC-170C ^® , FULORAD FC-430 ^® and FULORAD FC-431 ^® (Sumitomo 3M Co., Ltd. ( Sumitomo 3M Co., Ltd.)); SURFLON S-112 ^® , SURFLON S-113 ^® , SURFLON S-131 ^® , SURFLON S-141 ^® and SURFLON S-145 ^® (ASAHI Glass Co., Ltd.)); and SH-28PA ^® , SH-190 ^® , SH-193 ^® , SZ-6032 ^® and SF-8428 ^{® ,} etc. (Toray Silicone Co., Ltd.).

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

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

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

The color filter may be a green filter or a red filter, but is not limited thereto.

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

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

Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the following examples and comparative examples are provided for the purpose of description and the invention is not limited thereto. (Synthesis of a fat-soluble compound) Synthesis Example 1: Synthesis of a fat-soluble compound represented by Chemical Formula 5

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to 4-aminophthalonitrile (2.5 mmol) to prepare a hydrazine ion, followed by the addition of a hydrazine ion to An azo compound was prepared by dissolving a 2-ethylhexyl-substituted pyridone compound (2.5 mmol) in a weakly basic aqueous solution obtained by adding an aqueous NaOH solution thereto. Herein, the solid obtained therefrom is filtered, purified, and vacuum dried to obtain a fat-soluble compound represented by Chemical Formula 5. [Chemical Formula 5]

¹ H NMR (300 MHz, CDCl ₃ ) 7.88-7.85 2H, 7.73-7.69 1H, 3.87 2H, 2.60 3H, 1.79 1H, 1.40-1.15 8H, 0.93-0.88 6H.

GC/MS 416 m/z. Synthesis Example 2: Synthesis of a fat-soluble compound represented by Chemical Formula 6

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to 3-aminophthalonitrile (2.5 mmol) to prepare a hydrazine ion, which was then added thereto by using 2- An ethylhexyl-substituted pyridone compound (2.5 mmol) was dissolved in a weakly basic aqueous solution obtained by an aqueous NaOH solution to obtain an azo compound. Herein, the solid obtained therefrom is filtered, purified, and vacuum dried to obtain a fat-soluble compound represented by Chemical Formula 6. [Chemical Formula 6]

GC/MS 416 m/z. Synthesis Example 3: Synthesis of a fat-soluble compound represented by Chemical Formula 7

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to 4-aminophthalonitrile (2.5 mmol) to prepare a hydrazine ion, and the hydrazine ion was added to An n-butyl compound was dissolved in a weakly basic aqueous solution obtained by NaOH aqueous solution (2.5 mmol) to prepare an azo compound. Herein, the solid obtained therefrom is filtered, purified, and vacuum dried to obtain a fat-soluble compound represented by Chemical Formula 7. [Chemical Formula 7]

¹ H NMR (300 MHz, CDCl ₃ ) 7.88-7.85 2H, 7.73-7.69 1H, 3.86 2H, 2.60 3H, 1.50-1.12 4H, 0.96-0.92 3H. Synthesis Example 4: Synthesis of a fat-soluble compound represented by Chemical Formula 8

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to 4-aminophthalonitrile (2.5 mmol) to prepare a hydrazine ion, and the hydrazine ion was added to A weakly basic aqueous solution obtained by dissolving barbituric acid (2.5 mmol) in an aqueous NaOH solution to prepare an azo compound. Herein, the solid obtained therefrom was filtered, purified and vacuum dried, to which 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added, and the mixture was reacted in DMF solvent, followed by purification and vacuum drying. Thereby, a fat-soluble compound represented by Chemical Formula 8 is obtained. [Chemical Formula 8]

¹ H NMR (300 MHz, CDCl ₃ ) 14.3 1H, 7.95-7.94 1H, 7.86-7.80 2H, 4.03-3.87 4H, 1.78-1.62 4H, 1.46-1.36 4H, 1.01-0.94 6H. Synthesis Example 5: Synthesis of a fat-soluble compound represented by Chemical Formula 9

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to 4-aminophthalonitrile (2.5 mmol) to prepare a hydrazine ion, and the hydrazine ion was added to The azo compound was prepared by dissolving a weakly basic aqueous solution obtained by dissolving the acid (2.5 mmol) in an aqueous NaOH solution. Herein, the solid obtained therefrom was filtered, purified and vacuum dried, to which 4-iodotoluene (5.5 mmol) and potassium carbonate (7.5 mmol) were added, and the mixture was reacted in DMF solvent, purified and dried in vacuo. A fat-soluble compound represented by Chemical Formula 9 is obtained. [Chemical Formula 9]

¹ H NMR (300 MHz, CDCl ₃ ) 14.3 1H, 7.95-7.94 1H, 7.86-7.80 2H, 7.21 2H, 7.06 2H, 2.36 3H. Comparative Synthesis Example 1: Synthesis of a fat-soluble compound represented by Chemical Formula 10

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to 4-aminophenol (2.5 mmol) to prepare a hydrazine ion, and a hydrazine ion was added to the barbituric acid ( 2.5 mmol) a weakly basic aqueous solution obtained by dissolving in an aqueous NaOH solution to prepare an azo compound. Herein, the solid obtained therefrom was filtered, purified and dried in vacuo, to which 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added, and the mixture was reacted in DMF solvent, purified and dried in vacuo. Thus, a fat-soluble compound represented by Chemical Formula 10 is obtained. [Chemical Formula 10]

GC/MS 360 m/z. Comparative Synthesis Example 2: Synthesis of a fat-soluble compound represented by Chemical Formula 11

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to aniline (2.5 mmol) to prepare a hydrazine ion, and a hydrazine ion was added to the pyridine substituted by 2-ethylhexyl. A ketone compound (2.5 mmol) was dissolved in a weakly basic aqueous solution obtained by an aqueous NaOH solution to prepare an azo compound. Herein, the solid obtained therefrom is filtered, purified, and vacuum dried to obtain a fat-soluble compound represented by Chemical Formula 11. [Chemical Formula 11]

¹ H NMR (300 MHz, CDCl ₃ ) 7.53 2H, 7.44 2H, 7.36 1H, 3.87 2H, 2.60 3H, 1.79 1H, 1.40-1.15 8H, 0.93-0.88 6H. Comparative Synthesis Example 3: Synthesis of a fat-soluble compound represented by Chemical Formula 12

Hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of a 1.25 M aqueous solution) were added to the aniline (2.5 mmol) to prepare a hydrazine ion, and the hydrazine ion was added to dissolve the barbituric acid (2.5 mmol). A weakly basic aqueous solution obtained in an aqueous NaOH solution was used to prepare an azo compound. Herein, the solid obtained therefrom was filtered, purified and vacuum dried, to which 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added, and the mixture was reacted in DMF solvent, followed by purification and vacuum drying. Thereby, a fat-soluble compound represented by Chemical Formula 12 is obtained. [Chemical Formula 12]

¹ H NMR (300 MHz, CDCl ₃ ) 14.1 1H, 7.71 2H, 7.59 2H, 7.46 1H, 4.03-3.87 4H, 1.78-1.62 4H, 1.46-1.36 4H, 1.01-0.94 6H. (Evaluation) Assessment 1: Solubility in organic solvents

The dilution solvent (cyclohexanone) was separately added to 0.5 g of each compound according to Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 to Comparative Synthesis Example 3, using a mixed rotor (MIXROTAR VMR-5, Wellscens Iechi Seieido Co., Ltd.) Each solution was stirred at 25 ° C and 100 rpm for 1 hour and the solubility results are provided in Table 1. (Anone indicates cyclohexanone.) Solubility Evaluation Reference

A compound (solute) dissolved in an amount of 2.5% by weight or more based on the total amount of the diluent solvent: ○

A compound (solute) dissolved in an amount of less than 2.5% by weight based on the total amount of the diluent solvent: X

[Table 1]

Referring to Table 1, the compounds of Synthesis Example 1 to Synthesis Example 5 according to one example showed excellent solubility in an organic solvent as compared with the compounds of Comparative Synthesis Example 1 to Comparative Synthesis Example 3, and thus when used for photosensitivity The resin composition or the like exhibits excellent color characteristics. Assessment 2: Coloring

The maximum absorption wavelength (λ _max ) of the compounds of Synthesis Example 1 to Synthesis Example 5 and Comparative Synthesis Example 1 to Comparative Synthesis Example 3 was measured by using a UV-1800 UV-Vis spectrometer and is provided in Table 2. Further, 20 mg of the synthesis example 1 to synthesis example 5 and the comparative synthesis example 1 to the comparative synthesis example 3 compound were respectively dissolved in cyclohexanone to obtain 20 g of a dense solution, and 0.1 g of the dense solution was diluted to 10 g, thereby obtaining 0.001% by weight dilute solution. The spectrum of the 0.001% by weight solution was measured at room temperature, and its molar extinction coefficient was calculated by the following Equation 1 and is provided in Table 2. [Equation 1] A = ecl (A: maximum absorbance, e: molar extinction coefficient, c: molar concentration, l: optical path length) [Table 2]

Referring to Table 2, unlike Comparative Synthesis Example 1 to Comparative Synthesis Example 3, the compounds of Synthesis Example 1 to Synthesis Example 5 according to one embodiment contained a cyano group and thus exhibited excellent coloring characteristics although the maximum absorption wavelength was similar.

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

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Claims (12)

A fat-soluble compound represented by Chemical Formula 1: [Chemical Formula 1] Wherein in Chemical Formula 1, R ¹ is a cyano group, and R ² is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkyl group or a substituted or unsubstituted C6 group. To a C20 aryl group, n is an integer in the range of 2 to 5, and m is an integer in the range of 0 to 5, with the constraint being 2 ≤ n+m ≤ 5, and A being substituted or not Substituted C6 to C20 aromatic heterocyclic ring or substituted or unsubstituted C3 to C20 alicyclic heterocyclic ring. The fat-soluble compound according to claim 1, wherein the aromatic heterocyclic ring and the alicyclic heterocyclic ring include at least one structure represented by Chemical Formula 2 in the ring: [Chemical Formula 2] . The fat-soluble compound according to claim 1, wherein the aromatic heterocyclic ring is represented by Chemical Formula 3: [Chemical Formula 3] Wherein in Chemical Formula 3, R ³ is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, and R ⁴ to R ^{6 are} independently hydrogen and cyanide. A hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group. The fat-soluble compound according to claim 3, wherein R ³ is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, and R ⁴ is a cyano group. R ⁵ is a substituted or unsubstituted C1 to C20 alkyl, or a substituted or unsubstituted C6 to C20 aryl group, R ⁶ is hydroxy. The fat-soluble compound according to claim 1, wherein the alicyclic heterocyclic ring is represented by Chemical Formula 4: [Chemical Formula 4] Wherein in Chemical Formula 4, R ⁷ and R ^{8 are} independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group. The fat-soluble compound according to the first aspect of the invention, wherein the fat-soluble compound represented by Chemical Formula 1 is a compound represented by one of Chemical Formula 5 to Chemical Formula 9: [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] . The fat-soluble compound according to claim 1, wherein the fat-soluble compound is a yellow dye. A photosensitive resin composition comprising the fat-soluble compound according to any one of the claims of claim 1 to claim 7. The photosensitive resin composition according to claim 8, wherein the photosensitive resin composition further includes an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The photosensitive resin composition according to claim 9, wherein the photosensitive resin composition further comprises a pigment. A color filter manufactured by using the photosensitive resin composition as described in claim 8 of the patent application. The color filter of claim 11, wherein the color filter is a green filter or a red filter.