TWI673325B - Compound, photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

The present disclosure provides a compound represented by Chemical Formula 1, a photosensitive resin composition containing the compound, and a color filter including a photosensitive resin film manufactured using the photosensitive resin composition. [Chemical Formula 1] (In Chemical Formula 1, each substituent is the same as defined in the specification.)

Description

Compound, photosensitive resin composition containing the same, and color filter

The present disclosure 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 the advantages of lightness, thinness, low cost, low operating power consumption, and high support for integrated circuits, and have been more widely used in laptops, monitors, And TV screen. The liquid crystal display device includes a lower substrate and an upper substrate. A black matrix, a color filter, and an indium tin oxide pixel electrode are formed on the lower substrate. An active device including a liquid crystal layer, a thin film transistor, and a capacitor layer is formed on the upper substrate. Circuit part and indium tin oxide pixel electrode. The pixel area is formed by sequentially stacking a plurality of color filters (generally, formed by three primary colors (eg, red (R), green (G), and blue (B))) in a predetermined order to form each pixel. A color filter is formed in the middle, and a black matrix layer is provided on the transparent substrate in a predetermined pattern to form a boundary between each pixel. As one of various methods of forming a color filter, the pigment dispersion method provides a colored film by repeating a series of processes such as coating a photosensitive resin composition containing a colorant on a transparent substrate including a black matrix, The formed pattern is exposed, a non-exposed portion is removed with a solvent, and it is thermally cured. The photosensitive resin composition for manufacturing a color filter according to a pigment dispersion method generally includes a binder resin, a photopolymerizable monomer, a photopolymerization initiator, a solvent, and other additives. The pigment dispersion method having the above characteristics is actively applied to manufacturing liquid crystal displays such as mobile phones, laptop computers, monitors, and televisions. However, the photosensitive resin composition for a color filter using the pigment dispersion method has some disadvantages because it is difficult to finely pulverize the pigment powder, and various additives are required to stabilize the dispersion liquid even if the pigment powder is dispersed, and Complex processes, and it is difficult to further maintain the optimal quality of pigment dispersions under complex storage and transportation conditions. In addition, a color filter manufactured using a pigment-type photosensitive resin composition has limitations on brightness and contrast due to the fineness of the pigment. Therefore, it is necessary to develop a dye having heat resistance and chemical resistance similar to those of pigments.

The examples of the present invention provide a novel compound.

Another embodiment provides a photosensitive resin composition including the compound.

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

An embodiment of the present invention provides a compound represented by Chemical Formula 1. [Chemical Formula 1] In Chemical Formula 1, R ¹ is a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aromatic group. R ² is a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the limitation that the aryl group has at least one selected from A halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituent in a substituted or unsubstituted C1 to C10 alkylthio group, R ³ to R ^{5 are} independently substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, or substituted or unsubstituted C6 to C20 aryl, m and n is independently an integer ranging from 1 to 5, and L is represented by Chemical Formula 2, [Chemical Formula 2] Among them, in Chemical Formula 2, L ¹ is -O (C = O)-or -S-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 lipid Ring cyclic group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C20 heteroaryl group.

The R ¹ may be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group.

The R ² may be a substituted or unsubstituted adamantyl group, or a substituted or unsubstituted phenyl group. The phenyl group has at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 C10 alkylthio substituents.

The R ² may be "the unsubstituted adamantyl group" or "the phenyl group has only at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted Substituted C1 to C10 alkoxy, and substituted or unsubstituted C1 to C10 alkylthio. "

The R ³ to R ⁵ may be independently a substituted or unsubstituted C1 to C20 alkyl group.

The L may be represented by one selected from Chemical Formula 3 to Chemical Formula 7. [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] In Chemical Formulas 3 to 7, R ⁶ is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted fluorenyl group, and R ⁷ to R ^{9 are} independent Is a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, with the limitation that at least one of R ⁷ and R ⁸ is a hydroxyl group, and R ¹⁰ is a substituted or unsubstituted C1 to C10 alkyl group, o and p are independently integers in the range of 1 to 3, with restrictions such that 2 ≤ o + p ≤ 5 and q is an integer in the range of 0 to 4.

The substituted or unsubstituted amino group may be represented by Chemical Formula 8. [Chemical Formula 8] In Chemical Formula 8, R ^x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5.

The substituted or unsubstituted fluorenyl group may be represented by Chemical Formula 9. [Chemical Formula 9]

The R ⁶ may be a tert-butyl group, the substituent represented by Chemical Formula 8, or the substituent represented by Chemical Formula 9.

The R ⁷ to R ⁹ may be independently a hydroxyl group or a tert-butyl group, and the limitation is that at least one of R ⁷ and R ⁸ is a hydroxyl group.

The R ¹⁰ may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or substituted or Unsubstituted pentyl.

Chemical Formula 1 may be represented by Chemical Formula 10-1 or Chemical Formula 10-2. [Chemical Formula 10-1] [Chemical Formula 10-2] In Chemical Formulas 10-1 and 10-2, R ¹ is a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, and R ² is a A substituted or unsubstituted C3 to C20 cycloaliphatic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the limitation that the aryl group has at least one member selected from a halogen atom, Substituents in substituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkoxy, and substituted or unsubstituted C1 to C10 alkylthio, R ³ to R ^{5 are} independently A substituted or unsubstituted C1 to C20 alkyl group, and L is represented by Chemical Formula 2, [Chemical Formula 2] Wherein, in Chemical Formula 2, L ¹ is -O (C = O)-, and A is a substituted or unsubstituted C1 to C20 alkyl group, and a substituted or unsubstituted C3 to C20 alicyclic ring Group, or a substituted or unsubstituted C6 to C20 aryl group.

Chemical Formula 1 may be represented by one selected from Chemical Formulas 1-1 to 1-12. [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12]

The compound represented by Chemical Formula 1 may be a dye.

The dye may have a maximum absorbance in a wavelength range of 450 nm to 600 nm.

Another embodiment provides a photosensitive resin composition including the compound as a dye.

The photosensitive resin composition including the compound as a dye may further include a binder resin, a pigment, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

The dye may be included in an amount of 5 to 20% by weight based on the total amount of the photosensitive resin composition.

The dye may be contained in an amount of 10 to 15% by weight based on the total amount of the photosensitive resin composition.

The pigment may include a blue pigment.

The adhesive resin may include an acrylic adhesive resin, a cardo-based adhesive resin, or a combination thereof.

Based on the total amount of the photosensitive resin composition, the photosensitive resin composition may include: 1 to 10% by weight of the binder resin; 45% to 80% by weight including the dye and The coloring agent of the pigment; 1 to 5 wt% of the photopolymerizable monomer; 0.1 to 3 wt% of the photopolymerization initiator; and the balance is the solvent.

The photosensitive resin composition may further include the following additives: malonic acid; 3-amino-1,2-propanediol; a silane-based coupling agent; a leveling agent; a fluorine-based surfactant; a radical polymerization initiator; or combination.

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

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

The compound according to the embodiment has color characteristics, and when a photosensitive resin composition containing the compound is used, a color filter having improved brightness, heat resistance, and processability can be provided.

Hereinafter, embodiments of the present invention will be explained in detail. However, these embodiments are exemplary, the present invention is not limited thereto and the present invention is defined by the scope of the claims.

In this specification, when a specific definition is not otherwise provided, the term "substituted" means that at least one hydrogen is replaced with at least one substituent selected from a halogen atom (F, Cl, Br or I), a hydroxyl group, a nitro , Cyano, amino (NH ₂ , NH (R ²⁰⁰ ) or N (R ²⁰¹ ) (R ²⁰² ), where R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different and are independently C1 to C10 alkyl or C6 to C20 aryl), fluorenyl, hydrazino, fluorenyl, carboxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted Or unsubstituted alicyclic organic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.

In this specification, when a specific definition is not otherwise provided, "alkyl" means C1 to C20 alkyl and especially C1 to C15 alkyl, and "cycloalkyl" means C3 to C20 cycloalkyl and especially C3 to C18 Cycloalkyl, "alkoxy" means C1 to C20 alkoxy and especially C1 to C18 alkoxy, "aryl" means C6 to C20 aryl and especially C6 to C18 aryl, "alkenyl" is Refers to C2 to C20 alkenyl and especially C2 to C18 alkenyl, "alkylene" refers to C1 to C20 alkylene and especially C1 to C18 alkylene, and "alkylene" refers to C6 to C20 alkylene And especially C6 to C16 arylene.

In this specification, unless a specific definition is provided separately, "(meth) acrylate means both" acrylate "and" methacrylate ", and" (meth) acrylic acid "means" acrylic acid "and "Methacrylate".

In this specification, when a specific definition is not provided otherwise, the term "combination" refers to mixing or copolymerization. In addition, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means block copolymer to random copolymer.

In the chemical formula of this specification, unless a specific definition is provided otherwise, when a chemical bond is not drawn where it should be given, a hydrogen atom is bonded at the position.

In the present specification, the cardo-based resin refers to a resin containing at least one functional group selected from Chemical Formula 11-1 to Chemical Formula 11-11 in its skeleton.

In this specification, when a specific definition is not otherwise provided, "*" indicates a point connecting the same or different atom or chemical formula.

The embodiment of the present invention provides a compound represented by Chemical Formula 1. [Chemical Formula 1] In Chemical Formula 1, R ¹ is a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aromatic group. R ² is a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the limitation that the aryl group has at least one selected from A halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituent in a substituted or unsubstituted C1 to C10 alkylthio group, R ³ to R ^{5 are} independently substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, or substituted or unsubstituted C6 to C20 aryl, m and n is independently an integer ranging from 1 to 5, and L is represented by Chemical Formula 2, [Chemical Formula 2] Among them, in Chemical Formula 2, L ¹ is -O (C = O)-or -S-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 lipid Ring cyclic group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C20 heteroaryl group.

The compound according to the embodiment is represented by Chemical Formula 1, and has excellent spectral characteristics compared to conventional dyes, a high molar extinction coefficient, and organic compounds such as cyclohexanone, propylene glycol monomethyl ether acetate, and the like. Excellent solubility of solvents.

For example, R ¹ may be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group. When R ¹ is a halogen atom, heat resistance is higher than when R ¹ is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl is degraded.

R ² may be substituted or unsubstituted adamantyl, or substituted or unsubstituted phenyl. The phenyl group may have at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 Substituents in alkylthio.

For example, when R ² is a phenyl substituted with a trifluoromethyl group, heat resistance may be deteriorated when R ² is a phenyl substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group.

For example, R ² may be "unsubstituted adamantyl" or "the phenyl has only at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted Substituted C1 to C10 alkoxy, and substituted or unsubstituted C1 to C10 alkylthio. "

R ³ to R ⁵ may independently be substituted or unsubstituted C1 to C20 alkyl.

L may be represented by one selected from Chemical Formula 3 to Chemical Formula 7. [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] In Chemical Formulas 3 to 7, R ⁶ is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted fluorenyl group, and R ⁷ to R ^{9 are} independent Is a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, with the limitation that at least one of R ⁷ and R ⁸ is a hydroxyl group, and R ¹⁰ is a substituted or unsubstituted C1 to C10 alkyl group, o and p are independently integers in the range of 1 to 3, with restrictions such that 2 ≤ o + p ≤ 5 and q is an integer in the range of 0 to 4.

For example, a substituted or unsubstituted amino group may be represented by Chemical Formula 8. [Chemical Formula 8] In Chemical Formula 8, R ^x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5.

For example, a substituted or unsubstituted fluorenyl group may be represented by Chemical Formula 9. [Chemical Formula 9]

For example, R ⁶ may be tert-butyl, a substituent represented by Chemical Formula 8, or a substituent represented by Chemical Formula 9.

For example, R ⁷ to R ⁹ may be independently a hydroxyl group or a tert-butyl group, with the limitation that at least one of R ⁷ and R ⁸ is a hydroxyl group.

For example, R ¹⁰ may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or Substituted or unsubstituted pentyl.

In Chemical Formula 1, the position of R ¹ may be ortho, meta, or para. For example, the position of R ¹ may be adjacent or para, for example, adjacent. When R ¹ becomes meta, para, and ortho in order, brightness and heat resistance may be excellent in the order. In other words, a compound having in the para position of R ¹ can have more excellent than the compound of R ¹ has the brightness in the meta and heat resistance, and the compound having a ratio R1 of the compound may have for R ¹ in the ortho position with More excellent brightness and heat resistance.

For example, the compound represented by Chemical Formula 1 may be a compound represented by Chemical Formula 10-1 or a compound represented by Chemical Formula 10-2. [Chemical Formula 10-1] [Chemical Formula 10-2] In Chemical Formulas 10-1 and 10-2, R ¹ is a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, and R ² is a A substituted or unsubstituted C3 to C20 cycloaliphatic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the limitation that the aryl group has at least one member selected from a halogen atom, Substituents in substituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkoxy, and substituted or unsubstituted C1 to C10 alkylthio, R ³ to R ^{5 are} independently A substituted or unsubstituted C1 to C20 alkyl group, and L is represented by Chemical Formula 2, [Chemical Formula 2] Wherein, in Chemical Formula 2, L ¹ is -O (C = O)-, and A is a substituted or unsubstituted C1 to C20 alkyl group, and a substituted or unsubstituted C3 to C20 alicyclic ring Group, or a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by Chemical Formula 1 may be represented by one selected from Chemical Formulas 1-1 to 1-12. [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12]

The compound represented by Chemical Formula 1 according to the embodiment can express clear colors even in a small amount, and when used as a colorant, a display device having excellent color characteristics such as brightness and contrast can be manufactured. For example, the compound may be a colorant, such as a dye, such as a blue or violet dye, such as a dye having a maximum absorbance in a wavelength range of 300 nm to 600 nm, such as 450 nm to 600 nm.

In general, dyes are the most expensive of the components used in color filters. As a result, more expensive dyes may be needed to achieve the desired effect (such as high brightness, high contrast, etc.), and therefore, the unit cost of production may be increased. However, when the compound according to the 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 contrast) even in a small amount. ), And reduce the unit cost of production.

According to another embodiment, a photosensitive resin composition including the compound according to the embodiment as a dye is provided.

For example, based on the total amount of the photosensitive resin composition according to the embodiment, the photosensitive resin composition includes an amount of 5 to 20% by weight, for example, 10 to 15% by weight, represented by Chemical Formula 1 Compounds, and thus brightness, heat resistance, and chemical resistance can be significantly improved. That is, the dye may be contained in an amount of 5 to 20% by weight, for example, 10 to 15% by weight based on the total amount of the photosensitive resin composition, and thus brightness, heat resistance, and chemical resistance are improved.

For example, the photosensitive resin composition may include a compound according to an embodiment, a pigment, a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

The compound according to the embodiment can function as a colorant (for example, a dye, such as a blue dye or a purple dye) in the photosensitive resin composition, and thus can achieve excellent color characteristics.

The pigment may include, but is not limited to, a yellow pigment, a green pigment, a red pigment, a blue pigment, a purple 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 liquid may include a solid pigment, a solvent, and a dispersant that uniformly disperses the pigment in the solvent.

Based on the total amount of the pigment dispersion liquid, it may contain 1 to 20% by weight, such as 8 to 20% by weight, such as 15 to 20% by weight, such as 8 to 15% by weight, such as 10% by weight. A solid pigment in an amount of from 20 to 15% by weight or, 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 polyalkylene glycol and its ester, polyoxyalkylene, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonate, sulfonate, carboxylic acid ester , Carboxylate, alkylamidoalkylene oxide addition products, alkylamines, etc., and these dispersants can be used alone or as a mixture of two or more.

Commercial examples of the dispersant may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161 made by BYK Co., Ltd. , DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001; EFKA Chemicals Co. .) Manufactured by EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450; Solsperse manufactured by Zeneka ) 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, 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 1 to 20% by weight based on the total amount of the pigment dispersion. When a dispersant is included in the range, the dispersibility of the photosensitive resin composition is improved due to an appropriate viscosity, and thus optical quality, physical quality, and the like can be maintained when the photosensitive resin composition is applied to a product, and Chemical quality.

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

The pigment dispersion liquid may be contained in an amount of 40% to 60% by weight, for example, 45% to 55% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion liquid is included in the range, a process margin can be ensured, and color reproducibility and contrast can be improved.

Pigments can be pretreated with water-soluble inorganic salts and wetting agents. When the pigment is pretreated, the initial particle size of the pigment can be made finer.

The pretreatment may be performed as follows: kneading the water-soluble inorganic salt and the wetting agent and the pigment, and then filtering and washing the kneaded pigment.

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

Examples of the water-soluble inorganic salt may be, but are not limited to, sodium chloride, potassium chloride, and the like. The wetting agent can uniformly mix and pulverize the pigment with the water-soluble inorganic salt. Examples of wetting agents include alkylene glycol monoalkyl ethers such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, and the like; and alcohols such as ethanol, isopropyl ether, Propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, polyethylene glycol, glycerol polyethylene glycol, and the like. These wetting agents may be used alone or as a mixture of two or more.

The kneaded pigment may have an average particle diameter ranging from 30 nm to about 100 nm. When the average particle diameter of the pigment is within the range, heat resistance and light resistance can be improved, and a fine pattern can be effectively formed.

The photosensitive resin composition contains a coloring agent containing a dye and a pigment, and may contain the coloring agent in an amount of 45% to 80% by weight, for example, 55% to 70% by weight based on the total amount of the photosensitive resin composition. When the coloring agent is included in the range, the brightness, color reproducibility, pattern curability, heat resistance, and chemical resistance are improved.

The adhesive resin may include an acrylic adhesive resin, a Cardo adhesive resin, or a combination thereof.

The acrylic adhesive 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 containing 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 5 to 50% by weight, for example, 10 to 40% by weight, based on the total amount of the acrylic adhesive resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyl toluene, vinyl benzyl methyl ether, etc .; an unsaturated carboxylic acid ester compound such as (methyl Base) 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 .; unsaturated aminoalkyl carboxylic acid ester compounds, such as 2-aminoethyl (meth) acrylate, 2-methyl (meth) acrylate Dimethylaminoethyl, etc .; Vinyl carboxylic acid ester compounds, such as vinyl acetate, vinyl benzoate, etc .; Unsaturated glycidyl carboxylic acid ester compounds, such as glycidyl (meth) acrylate, etc .; Acrylonitrile compounds , Such as (meth) acrylonitrile, etc .; unsaturated amidine compounds, such as (meth) acrylamide, etc .; and the second ethylenically unsaturated monomer may be used alone or as two or more Use as a mixture.

Specific examples of the acrylic adhesive resin may be a polybenzyl methacrylate copolymer, a (meth) acrylic acid / benzyl methacrylate copolymer, a (meth) acrylic acid / benzyl methacrylate / styrene Copolymer, (meth) acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate Ester copolymers and the like are not limited thereto. These acrylic adhesive resins can be used alone or as a mixture of two or more.

The weight average molecular weight of the acrylic adhesive resin may be 3,000 g / mol to 150,000 g / mol, such as 5,000 g / mol to 50,000 g / mol, or, for example, 20,000 g / mol to 30,000 g / mol. When the weight-average molecular weight of the acrylic adhesive resin is within the above range, the photosensitive resin composition has good physical properties and chemical properties, appropriate viscosity, and properties in close contact with the substrate during the manufacture of the color filter. .

The acid value of the acrylic adhesive resin may be 15 mgKOH / g to 60 mgKOH / g, such as 20 mgKOH / g to 50 mgKOH / g. When the acid value of the acrylic adhesive resin is within the range, the resolution of the pixel pattern is improved.

The Cardo-based adhesive resin may include a repeating unit represented by Chemical Formula 11. [Chemical Formula 11] In Chemical Formula 11, R ¹¹ and R ^{12 are} independently a hydrogen atom or a substituted or unsubstituted (meth) acryloxyalkyl group, and R ¹³ and R ^{14 are} independently a hydrogen atom, a halogen atom, or Substituted or unsubstituted C1 to C20 alkyl, and Z ¹ is a single bond, O, CO, SO ₂ , CR ¹⁵ R ¹⁶ , SiR ¹⁷ R ¹⁸ (wherein R ¹⁵ to R ^{18 are} independently a hydrogen atom or via One of substituted or unsubstituted C1 to C20 alkyl groups), or a linking group represented by Chemical Formula 11-1 to Chemical Formula 11-11, [Chemical Formula 11-1] [Chemical Formula 11-2] [Chemical Formula 11-3] [Chemical Formula 11-4] [Chemical Formula 11-5] (In Chemical Formula 11-5, R ^a is a hydrogen atom, an ethyl group, C ₂ H ₄ Cl, C ₂ H ₄ OH, CH ₂ CH = CH ₂ , or a phenyl group) [Chemical Formula 11-6] [Chemical Formula 11-7] [Chemical Formula 11-8] [Chemical Formula 11-9] [Chemical Formula 11-10] [Chemical Formula 11-11] Z ² is an acid dianhydride residue, and m1 and m2 are independently an integer ranging from 0 to 4.

At least one of the ends of the Cardo-type adhesive resin may include a functional group represented by Chemical Formula 12. [Chemical Formula 12] In Chemical Formula 12, Z ^{3 is} represented by Chemical Formula 12-1 or Chemical Formula 12-7. [Chemical Formula 12-1] (In Chemical Formula 12-1, R ^b and R ^{c are} independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group, or an ether group) [Chemical Formula 12-2] [Chemical Formula 12-3] [Chemical Formula 12-4] [Chemical Formula 12-5] (In Chemical Formula 12-5, R ^d is O, S, NH, substituted or unsubstituted C1 to C20 alkylene, C1 to C20 alkylamino, or C2 to C20 alkenylamino) [Chemical Formula 12-6] [Chemical Formula 12-7]

Cardo-based adhesive resins can be prepared, for example, by mixing at least two of the following: fluorene-containing compounds, such as 9,9-bis (4-oxiranylmethoxyphenyl) fluorene (9,9-bis (4-oxiranylmethoxyphenyl) fluorene); anhydride compounds such as pyromellitic dianhydride, naphthalenetetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutane Tetracarboxylic dianhydride, pyrene tetracarboxylic dianhydride, tetrahydrofuran tetracarboxylic dianhydride, and tetrahydrophthalic anhydride; glycol compounds such as ethylene glycol, propylene glycol, and polyethylene glycol; alcohol compounds such as methanol, ethanol , Propanol, n-butanol, cyclohexanol, and benzyl alcohol; solvent-based compounds such as propylene glycol methyl ethyl acetate and N-methylpyrrolidone; phosphorus compounds such as triphenylphosphine; and amine or ammonium salt compounds, Examples include tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, and benzyltriethylammonium chloride.

Cardo-type adhesive resins have low developability. When a color filter is formed of a photosensitive resin composition having a cardo-type adhesive resin, it is difficult to control the developability of a pattern. Here, the developability of the pattern may be controlled using an acrylic adhesive resin together with a Cardo-based adhesive resin as the adhesive resin.

In addition, when a Cardo-based adhesive resin is used together with an acrylic-based adhesive resin, a photosensitive resin composition having high resolution and high brightness characteristics and excellent close contact power can be obtained.

The weight average molecular weight of the Cardo-based adhesive resin may be 500 g / mol to 50,000 g / mol, for example, 3,000 g / mol to 30,000 g / mol. When the weight-average molecular weight of the Cardo-based adhesive resin is within the range, a pattern can be formed well without residue during the manufacture of a color filter, and the film thickness does not decrease during development.

Cardo-series adhesive resins can have an acid value of 100 mgKOH / g to 140 mgKOH / g.

The binder resin may be contained in an amount of 1 to 10% by weight, for example, 1 to 5% by weight based on the total amount of the photosensitive resin composition. When the binder resin is included in the range, excellent sensitivity, developability, resolution, and pattern linearity can be obtained.

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

The photopolymerizable monomer has an ethylenically unsaturated double bond, and therefore, it 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 monomer 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 di (Meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaisopentaerythritol hexa (meth) acrylate, dipentaerythritol di (Meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, Ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tri (meth) acryloxyethyl phosphate, phenolic epoxy (meth) acrylate, and the like.

Commercial examples of the photopolymerizable monomer are as follows. Monofunctional (meth) acrylates may include Aronix M-101 ^® , M-111 ^® , M-114 ^® (Toagosei Chemistry Industry Co., Ltd.); Kaya KAYARAD TC-110S ^® , TC-120S ^® (Nippon Kayaku Co., Ltd.); V-158 ^® , V-2311 ^® (Osaka Organic Chemical Co., Ltd. Ind., Ltd.)) and so on. Examples of difunctional (meth) acrylates may include Aronix M-210 ^® , M-240 ^® , M-6200 ^® (East Asia Chemical Co., Ltd.), KAYARAD HDDA ^® , HX -220 ^® , R-604 ^® (Nippon Kayaku Co., Ltd.), V-260 ^® , V-312 ^® , V-335 HP ^® (Osaka Organic Chemical Co., Ltd.), etc. Examples of trifunctional (meth) acrylates may include Aronix M-309 ^® , M-400 ^® , M-405 ^® , M-450 ^® , M-7100 ^® , M-8030 ^® , M- 8060 ^® (East Asia Chemical Co., Ltd.), KAYARAD TMPTA ^® , DPCA-20 ^® , DPCA-30 ^® , DPCA-60 ^® , DPCA-120 ^® (Nippon Kayaku Co., Ltd.), V-295 ^® , V-300 ^® , V-360 ^® , V-GPT ^® , V-3PA ^® , V-400 ^® (Osaka Organic Chemical Co., Ltd.), etc. These photopolymerizable monomers may be used alone or as a mixture of two or more.

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

The photopolymerizable monomer may be included in an amount of 1 to 5% by weight, for example, 1 to 3% by weight based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included in the range, the photopolymerizable monomer can be sufficiently cured upon exposure during the pattern forming process and thus reliability is improved, and developability by development with an alkaline developer Be improved.

The photopolymerization initiator is an initiator commonly used in a photosensitive resin composition, and may be, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an oxime-based compound. A compound, or a combination thereof.

Examples of the acetophenone-based compound may be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylacetophenone, p-tert-butyl Trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (Methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinyl) -but-1-one, etc. .

Examples of the benzophenone-based compound may be benzophenone, benzophenethyl benzoate, benzophenethyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated dibenzophenone Benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone Ketones, 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 so on.

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-phenyl4,6-bis (trichloromethyl) -s-triazine, 2- (3 ', 4 '-Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) ) -S-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis ( (Trichloromethyl) -s-triazine, 2-biphenyl 4,6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-tri Hydrazine, 2- (naphthalene-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthalene-1-yl) -4,6-bis ( (Trichloromethyl) -s-triazine, 2-4-bis (trichloromethyl) -6-piperidyl-s-triazine, 2-4-bis (trichloromethyl) -6- (4- Methoxystyryl) -s-triazine and the like.

Examples of the oxime-based compound may be an O-fluorenyl oxime-based compound, 2- (o-benzylidene oxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (O-ethylammonium oxime) -1- [9-ethyl-6- (2-methylbenzylidene) -9H-oxazol-3-yl] ethanone, O-ethoxycarbonyl-α-oxyl Amino-1-phenylpropan-1-one and the like. Examples of the O-fluorenyl oxime-based compound may be 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl- Phenyl) -butan-1-one, 1- (4-phenylthiophenyl) -butan-1,2-dione 2-oxime-O-benzoate, 1- (4-phenylthiobenzene ) -Octyl-1,2-dione 2-oxime-O-benzoate, 1- (4-phenylthiophenyl) -oct-1-oneoxime-O-acetate, and 1- (4-phenylthiophenyl) -butan-1-oneoxime-O-acetate.

In addition to the compound, the photopolymerization initiator may further include an oxazole-based compound, a dione-based compound, a boronic acid-based compound, a diazonium-based compound, an imidazole-based compound, a biimidazole-based compound, a fluorene-based compound, and the like.

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

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

The photopolymerization initiator may be contained in an amount of 0.1 to 3% by weight, for example, 0.1 to 2% by weight based on the total amount of the photosensitive resin composition. When a photopolymerization initiator within the range is included, since sufficient curing is performed during the exposure of the pattern forming process, excellent reliability can be ensured, and the transmittance can be prevented from being deteriorated by the non-reactive initiator.

The solvent is a material having compatibility with the compound according to the embodiment, a pigment, a binder resin, a photopolymerizable monomer, and a photopolymerization initiator but does not react therewith.

Examples of the solvent may include alcohols such as methanol, ethanol, and the like; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, anisole, tetrahydrofuran, and the like; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol Alcohol monoethyl ether, etc .; acetic acid cellosolve, such as methyl acetate cellosolve, ethyl acetate cellosolve, diethyl cellosolve, etc .; carbitol, such as methyl ethyl carbitol, diethyl Carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether, etc .; propylene glycol alkyl ether acetate, For example, 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-pentane Ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-pentyl ketone, 2-heptanone, etc .; saturated aliphatic monocarboxylic acid alkyl esters, such as ethyl acetate, n-butyl acetate Esters, isobutyl acetate, etc .; lactate esters, such as methyl lactate, ethyl lactate, etc .; alkyloxyacetates, such as methyloxyacetate, ethyloxyacetate, oxygen Butyl acetate, etc .; Alkoxy acetate, such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxylate, etc. ; Alkyl 3-oxypropionate, such as methyl 3-oxypropionate, ethyl 3-oxypropionate, etc .; alkyl 3-alkoxypropionate, such as 3-methoxypropionic acid Methyl ester, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc .; alkyl 2-oxypropionate, such as 2-oxypropionate Methyl ester, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc .; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate, 2-methoxypropionate Ethyl propionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc .; 2-oxy-2-methylpropionate, such as 2-oxy-2-methylpropionate Methyl esters, ethyl 2-oxy-2-methylpropionate, etc .; monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyl esters, such as 2-methoxy Methyl-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc .; esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate , Ethyl hydroxyacetate, 2-hydroxy-3-methyl Methyl butyrate and the like; ketoesters such as ethyl pyruvate and the like. In addition, high boiling point solvents such as N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-diamine Methylacetamide, N-methylpyrrolidone, dimethylarsine, benzylethyl ether, dihexyl ether, acetoacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonyl Alcohol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl acetate Cellosolve, etc.

In view of miscibility and reactivity, glycol ethers, such as ethylene glycol monoethyl ether, etc .; glycol alkyl ether acetates, such as ethyl cellosolve, etc .; esters, such as 2-hydroxypropyl Ethyl acetate, etc .; carbitol, such as diethylene glycol monomethyl ether, etc .; and propylene glycol alkyl ether acetate, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, and the like.

The remaining amount (for example, 15 to 50% by weight, or, for example, 20 to 40% by weight) of the photosensitive resin composition may be included. When the solvent is included in the range, the photosensitive resin composition may have an appropriate viscosity, and therefore, coating processability may be improved when applied to a product.

The photosensitive resin composition according to the embodiment may further include the following other additives to prevent the generation of stains or spots during coating, adjust the leveling characteristics, or prevent pattern residue due to being undeveloped: for example, malonic acid; 3-amino- 1,2-propanediol; silane-based coupling agent; leveling agent; fluorine-based surfactant; radical polymerization initiator; or a combination thereof.

Examples of the silane-based coupling agent may be trimethoxysilylbenzoic acid, γ-methacryloxypropyltrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, γ-isocyanate Propyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc., and the silane-based coupling agent may be It is used alone or as a mixture of two or more.

Examples of the fluorine-based surfactant may be the following commercially available fluorine-based surfactants: for example, 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.); SURFLON S-112 ^® , SURFLON S-113 ^® , SURFLON S-131 ^® , SURFLON S-141 ^® and SURFLON S-145 ^® (Asahi Glass Co., Ltd. ( Asahi Glass Co., Ltd.); and SH-28PA ^® , SH-190 ^® , SH-193 ^® , SZ-6032 ^® and SF-8428 ^® (Toray Silicone Co., Ltd. )).

The amount of these additives can be adjusted according to the desired properties.

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

The epoxy compound may include a phenol novolac epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A epoxy compound, an alicyclic epoxy compound, or a combination thereof.

In addition, unless the properties of the photosensitive resin composition are deteriorated by other additives, the photosensitive resin composition may include a predetermined amount of other additives such as an antioxidant, a stabilizer, and the like.

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

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

The process includes: coating a positive photosensitive resin composition on a support substrate by a method such as spin coating, slit coating, inkjet printing, and the like; and drying the coated positive photosensitive resin composition to form a photosensitive resin composition. Material film; exposing the positive-type photosensitive resin composition film; developing the exposed positive-type photosensitive resin composition film in an alkaline aqueous solution to obtain a photosensitive resin film; and heat-treating the photosensitive resin film. The conditions of the patterning process are well known in the related art and will not be described in detail in this specification.

Hereinafter, the present invention is explained in more detail with reference to examples, however, these examples should not be construed as limiting the scope of the present invention in any sense.

(Synthesis of compounds)

Synthesis Example 1-1: Synthesis of a compound represented by Chemical Formula 2-1 2-Bromo-2-methoxyacetophenone (1 mol) was added to dimethyl formamide (DMF, 250 ml) while being stirred at room temperature. To the reaction solution was added potassium phthalimide (0.95 mol), and the mixture was stirred for 3 hours. When the reaction was completed, a precipitate was obtained using water (2500 ml), and then filtered and dried to obtain a compound represented by Chemical Formula 2-1. (Yield: 78%)

Synthesis Example 1-2: Synthesis of compound represented by Chemical Formula 2-2 [Chemical Formula 2-2] A compound represented by Chemical Formula 2-2 was synthesized according to the same method as Synthesis Example 1-1 using 2-bromo-4'-methoxyacetophenone as a starting material. (Yield: 75.6%)

Synthesis Example 1-3: Synthesis of a compound represented by Chemical Formula 2-3 [Chemical Formula 2-3] A compound represented by Chemical Formula 2-3 was synthesized according to the same method as Synthesis Example 1-1 using 2-bromo-2'-chloroacetophenone as a starting material. (Yield: 74.5%)

Synthesis Example 1-4: Synthesis of a compound represented by Chemical Formula 2-4 [Chemical Formula 2-4] According to the same method as Synthesis Example 1-1, a compound represented by Chemical Formula 2-4 was synthesized using 2-bromo-4'-chloroacetophenone as a starting material. (Yield: 78.4%)

Synthesis Example 1-5: Synthesis of a compound represented by Chemical Formula 2-5 [Chemical Formula 2-5] A compound represented by Chemical Formula 2-5 was synthesized according to the same method as Synthesis Example 1-1 using 2-bromo-4'-phenylacetophenone as a starting material. (Yield: 76.8%)

Synthesis Example 1-6: Synthesis of compound represented by Chemical Formula 2-6 [Chemical Formula 2-6] A compound represented by Chemical Formula 2-6 was synthesized according to the same method as Synthesis Example 1-1 using 2-bromoacetophenone as a starting material. (Yield: 81.5%)

Synthesis Example 2: Synthesis of a compound represented by Chemical Formula 3-1 Toluene (500 ml) was added cyanoacetic acid (1.46 mol) and 2,6-di-tert-butyl-4-methylcyclohexanol (1.33 mol), and the mixture was stirred at room temperature. Pyridine (1.59 mol) was added to the reaction solution while stirring. To this solution was added anhydrous acetic acid (2.65 mol) and stirred for 6 hours at the same time to complete the reaction. The reaction solution was washed twice with a 10% aqueous hydrochloric acid solution (500 g) and twice with an aqueous sodium chloride solution (500 g). Water was removed using magnesium sulfate, and a compound represented by Chemical Formula 3-1 was obtained by filtering and drying it. (Yield: 62.5%)

Synthesis Example 3-1: Synthesis of a compound represented by Chemical Formula 4-1 To a mixed solution of methanol (10 ml) and water (10 ml) was added a compound represented by Chemical Formula 2-1 (3.8 mol) and a compound represented by Chemical Formula 3-1 (4.15 mol), and then simultaneously Stirred. A 48% aqueous sodium hydroxide solution (8.36 mol) was added dropwise thereto, and the mixture was heated to 70 ° C and stirred for 3 hours. The reaction was monitored using thin layer chromatography (TLC) and then completed. The resultant was cooled to room temperature, washed with water and hexane, and dried to obtain a compound represented by Chemical Formula 4-1. (Yield: 69%)

Synthesis Example 3-2: Synthesis of a compound represented by Chemical Formula 4-2 [Chemical Formula 4-2] A compound represented by Chemical Formula 4-2 was synthesized according to the same method as Synthesis Example 3-1 using a compound represented by Chemical Formula 2-2 as a starting material. (Yield: 71.8%)

Synthesis Example 3-3: Synthesis of a compound represented by Chemical Formula 4-3 [Chemical Formula 4-3] A compound represented by Chemical Formula 4-3 was synthesized according to the same method as Synthesis Example 3-1 using a compound represented by Chemical Formula 2-3 as a starting material. (Yield: 70.2%)

Synthesis Example 3-4: Synthesis of a compound represented by Chemical Formula 4-4 [Chemical Formula 4-4] A compound represented by Chemical Formula 4-4 was synthesized according to the same method as Synthesis Example 3-1 using a compound represented by Chemical Formula 2-4 as a starting material. (Yield: 69.2%)

Synthesis Example 3-5: Synthesis of a compound represented by Chemical Formula 4-5 [Chemical Formula 4-5] A compound represented by Chemical Formula 4-5 was synthesized according to the same method as Synthesis Example 3-1 using a compound represented by Chemical Formula 2-5 as a starting material. (Yield: 70.1%)

Synthesis Example 3-6: Synthesis of compound represented by Chemical Formula 4-6 [Chemical Formula 4-6] A compound represented by Chemical Formula 4-6 was synthesized according to the same method as Synthesis Example 3-1 using a compound represented by Chemical Formula 2-6 as a starting material. (Yield: 73.4%)

Synthesis Example 4-1: Synthesis of a compound represented by Chemical Formula 5-1 A compound represented by Chemical Formula 4-1 (0.38 mol) was added to acetic acid (800 g), and then at the same time, it was stirred at room temperature. To this reaction solution was added triethyl orthoformate (0.23 mol), and the mixture was heated to 130 ° C and stirred for 10 hours. When the reaction was completed, the resultant was filtered with acetonitrile (100 g), and acetonitrile (100 g) was added thereto, and the mixture was stirred. This solution was filtered and then washed with acetonitrile (100 g), and dried to obtain a compound represented by Chemical Formula 5-1. (Yield: 68.7%)

Synthesis Example 4-2: Synthesis of a compound represented by Chemical Formula 5-2 [Chemical Formula 5-2] A compound represented by Chemical Formula 5-2 was synthesized according to the same method as Synthesis Example 4-1 using a compound represented by Chemical Formula 4-2 as a starting material. (Yield: 70.4%)

Synthesis Example 4-3: Synthesis of a compound represented by Chemical Formula 5-3 [Chemical Formula 5-3] A compound represented by Chemical Formula 5-3 was synthesized according to the same method as Synthesis Example 4-1 using a compound represented by Chemical Formula 4-3 as a starting material. (Yield: 69.6%)

Synthesis Example 4-4: Synthesis of a compound represented by Chemical Formula 5-4 [Chemical Formula 5-4] A compound represented by Chemical Formula 5-4 was synthesized according to the same method as Synthesis Example 4-1 using a compound represented by Chemical Formula 4-4 as a starting material. (Yield: 71.9%)

Synthesis Example 4-5: Synthesis of a compound represented by Chemical Formula 5-5 [Chemical Formula 5-5] A compound represented by Chemical Formula 5-5 was synthesized according to the same method as Synthesis Example 4-1 using a compound represented by Chemical Formula 4-5 as a starting material. (Yield: 74.2%)

Synthesis Example 4-6: Synthesis of compound represented by Chemical Formula 5-6 [Chemical Formula 5-6] A compound represented by Chemical Formula 5-6 was synthesized according to the same method as Synthesis Example 4-1 using a compound represented by Chemical Formula 4-6 as a starting material. (Yield: 72.8%)

Synthesis Example 5-1: Synthesis of a compound represented by Chemical Formula 6-1 A compound represented by Chemical Formula 5-1 was added to toluene (17 ml), and at the same time, stirring was performed. To this solution was added dropwise sodium hydroxide (40% aqueous solution, 0.036 mmol). Subsequently, tetrabutyl ammonium bromide (TBAB, 0.0012 mmol) was added thereto at room temperature, the mixture was stirred for 30 minutes and cooled to 0 ° C using an ice bath. To the reaction solution was added 1-adamantane carbonyl chloride (0.072 mmol). The mixture was stirred for 2 hours while warming to room temperature after removing the ice bath to complete the reaction. The resultant was washed and dried with water (100 ml) and ethyl acetate (100 ml) to obtain a compound represented by Chemical Formula 6-1. (Yield: 72.5%)

Synthesis Example 5-2: Synthesis of a compound represented by Chemical Formula 6-2 [Chemical Formula 6-2] A compound represented by Chemical Formula 6-2 was synthesized by the same method as Synthesis Example 5-1 using a compound represented by Chemical Formula 5-1 and 4-methoxy-2-methylbenzidine chloride as a starting material. (Yield: 74.2%)

Synthesis Example 5-3: Synthesis of a compound represented by Chemical Formula 6-3 [Chemical Formula 6-3] According to the same method as in Synthesis Example 5-1, a compound represented by Chemical Formula 6-3 was synthesized using a compound represented by Chemical Formula 5-2 and 1-adamantanecarbamyl chloride as starting materials. (Yield: 74.5%)

Synthesis Example 5-4: Synthesis of a compound represented by Chemical Formula 6-4 [Chemical Formula 6-4] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-4 was synthesized using a compound represented by Chemical Formula 5-2 and 4-methoxy-4-methylbenzidine chloride as a starting material. (Yield: 78.2%)

Synthesis Example 5-5: Synthesis of a compound represented by Chemical Formula 6-5 [Chemical Formula 6-5] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-5 was synthesized using a compound represented by Chemical Formula 5-4 and 1-adamantanecarbamyl chloride as starting materials. (Yield: 72.6%)

Synthesis Example 5-6: Synthesis of a compound represented by Chemical Formula 6-6 [Chemical Formula 6-6] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-6 was synthesized using a compound represented by Chemical Formula 5-5 and 1-adamantanecarbamyl chloride as starting materials. (Yield: 70.4%)

Synthesis Example 5-7: Synthesis of compound represented by Chemical Formula 6-7 [Chemical Formula 6-7] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-7 was synthesized using a compound represented by Chemical Formula 5-5 and 4-methoxy-2-methylbenzidine chloride as a starting material. (Yield: 74.6%)

Synthesis Example 5-8: Synthesis of a compound represented by Chemical Formula 6-8 [Chemical Formula 6-8] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-8 was synthesized using a compound represented by Chemical Formula 5-5 and 2-methoxybenzidine chloride as a starting material. (Yield: 75.1%)

Synthesis Example 5-9: Synthesis of compound represented by Chemical Formula 6-9 [Chemical Formula 6-9] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-9 was synthesized using a compound represented by Chemical Formula 5-5 and 2- (methylthio) benzidine chloride as a starting material. (Yield: 72.3%)

Synthesis Example 5-10: Synthesis of a compound represented by Chemical Formula 6-10 [Chemical Formula 6-10] According to the same method as Synthesis Example 5-1, a compound represented by Chemical Formula 6-10 was synthesized using a compound represented by Chemical Formula 5-6 and 4-methoxy-2-methylbenzidine chloride as starting materials. (Yield: 72.3%)

Synthesis Example 5-11: Synthesis of a compound represented by Chemical Formula 6-11 [Chemical Formula 6-11] According to the same method as in Synthesis Example 5-1, a compound represented by Chemical Formula 6-11 was synthesized using a compound represented by Chemical Formula 5-2 and 2-trifluoromethylbenzidine chloride as a starting material. (Yield: 78.2%)

Synthesis Example 6-1: Synthesis of a compound represented by Chemical Formula 7-1 To a mixed solution of water (60 ml) / methanol (90 ml) was added 4-tert-butylbenzoic acid (0.14 mol) and sodium methoxide (30% methanol solution, 0.14 mol). To this solution was added zinc sulfate 7 hydrate (0.06 mol). The mixture was stirred at room temperature for 1 hour to complete the reaction. When the reaction was completed, the resultant was filtered, and washed with water (1000 ml) and methanol (1000 ml) to obtain a compound represented by Chemical Formula 7-1. (Yield: 90.1%)

Synthesis Example 6-2: Synthesis of a compound represented by Chemical Formula 7-2 [Chemical Formula 7-2] A compound represented by Chemical Formula 7-2 was synthesized by the same method as in Synthesis Example 6-1 using 2- (2,3-dimethylphenylamino) benzoic acid as a starting material. (Yield: 93.3%)

Synthesis Example 7-1: Synthesis of a compound (dye) represented by Chemical Formula 1-1 To ethanol (10 ml), a compound represented by Chemical Formula 6-1 (0.642 mmol) and a compound represented by Chemical Formula 7-1 (0.835 mmol) were added, and the mixture was stirred at room temperature. The reaction was checked by TLC and completed. After the ethanol of the reaction solution was dried, the resultant was washed with methylene chloride (100 ml) and water (100 ml) to obtain a compound represented by Chemical Formula 1-1. (Yield: 81.7%, matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (Maldi tof Mass): 1454.8)

Synthesis Example 7-2: Synthesis of a compound (dye) represented by Chemical Formula 1-2 [Chemical Formula 1-2] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1426.7 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-4 and a compound represented by Chemical Formula 7-1 were used as starting materials to synthesize from Chemical Formula 1 Compound represented by -2. (Yield: 82.8%)

Synthesis Example 7-3: Synthesis of compound (dye) represented by Chemical Formula 1-3 [Chemical Formula 1-3] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1465.7 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-5 and a compound represented by Chemical Formula 7-1 were synthesized as starting materials by Chemical Formula 1 Compound represented by -3. (Yield: 84.1%)

Synthesis Example 7-4: Synthesis of a compound (dye) represented by Chemical Formula 1-4 [Chemical Formula 1-4] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1547.9 According to the same method as in Synthesis Example 7-1, using the compound represented by Chemical Formula 6-6 and the compound represented by Chemical Formula 7-1 as starting materials, a compound of Chemical Formula 1 was synthesized. Compound represented by -4. (Yield: 87.2%)

Synthesis Example 7-5: Synthesis of compound (dye) represented by Chemical Formula 1-5 [Chemical Formula 1-5] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1491.7 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 1-5 was synthesized using a compound represented by Chemical Formula 7-1 as a starting material. (Yield: 82.2%)

Synthesis Example 7-6: Synthesis of compound (dye) represented by Chemical Formula 1-6 [Chemical Formula 1-6] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1522.67 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-9 and a compound represented by Chemical Formula 7-1 were used as starting materials. Compound represented by -6. (Yield: 81.8%)

Synthesis Example 7-7: Synthesis of compound (dye) represented by Chemical Formula 1-7 [Chemical Formula 1-7] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1498.92 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-2 and a compound represented by Chemical Formula 7-2 were used as starting materials to synthesize a compound of Chemical Formula 1 Compound represented by -7. (Yield: 85.8%)

Synthesis Example 7-8: Synthesis of compound (dye) represented by Chemical Formula 1-8 [Chemical Formula 1-8] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1454.81 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-3 and a compound represented by Chemical Formula 7-2 were used as starting materials. Compound represented by -8. (Yield: 82.3%)

Synthesis Example 7-9: Synthesis of compound (dye) represented by Chemical Formula 1-9 [Chemical Formula 1-9] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1541.49 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-7 and a compound represented by Chemical Formula 7-2 were used as starting materials. Compound represented by -9. (Yield: 84.3%)

Synthesis Example 7-10: Synthesis of compound (dye) represented by Chemical Formula 1-10 [Chemical Formula 1-10] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1649.52 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-8 and a compound represented by Chemical Formula 7-2 were used as starting materials. Compound represented by -10. (Yield: 80.6%)

Synthesis Example 7-11: Synthesis of compound (dye) represented by Chemical Formula 1-11 [Chemical Formula 1-11] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1429.17 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-2 and a compound represented by Chemical Formula 7-1 were used as starting materials. Compound (dye) represented by -11. (Yield: 85.8%)

Synthesis Example 7-12: Synthesis of compound (dye) represented by Chemical Formula 1-12 [Chemical Formula 1-12] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1401.11 According to the same method as in Synthesis Example 7-1, a compound represented by Chemical Formula 6-11 and a compound represented by Chemical Formula 7-2 were used as starting materials. Compound (dye) represented by -12. (Yield: 85.8%)

Comparative Synthesis Example 1: Synthesis of a compound represented by Chemical Formula C-1 [Chemical Formula C-1] Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1366.69 According to the same method as in Synthesis Example 7-1, using the compound represented by Chemical Formula 6-10 and the compound represented by Chemical Formula 7-1 as starting materials, a compound of Chemical Formula C was synthesized. Compound represented by -1. (Yield: 78.6%)

Evaluation 1: Solubility measurement

To 0.5 g of each compound synthesized in Synthesis Example 7-1 to Synthesis Example 7-12 and Comparative Synthesis Example 1, a diluent solvent (Anone) was added, and a rotary mixer (MIXROTAR) VMR was used. -5, Luchi Inc.) stirred each solution for 1 hour at 25 ° C and 100 rpm, and then confirmed the solubility of each compound and the results are shown in Table 1. (Anone refers to cyclohexanone.)

Solubility evaluation reference Based on the total amount of the diluted solvent, the compound (solute) is greater than or equal to 2.5% by weight: ○ Based on the total amount of the diluted solvent, the compound (solute) is less than 2.5% by weight: ×

[Table 1] (Unit:% by weight)

Referring to Table 1, the compounds according to Examples 7-1 to 7-12 (compounds according to Examples) have superior solubility with respect to organic solvents as compared to the compounds according to Comparative Synthesis Example 1, and therefore when used for photosensitive resins The composition exhibits excellent color characteristics when waiting.

(Synthesis of photosensitive resin composition)

Examples 1 to 14 and Comparative Examples 1 to 4

The photosensitive resin compositions according to Examples 1 to 14 and Comparative Examples 1 to 4 were prepared to have each composition using the following components shown in Tables 2 and 3.

Specifically, the photopolymerization initiator was dissolved in a solvent, 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, a dye and a pigment dispersion liquid were added as a colorant to the obtained reactant, and the obtained mixture was stirred at room temperature for one hour. Then, the product thus obtained was filtered three times to remove impurities to prepare a photosensitive resin composition.

(A) Adhesive resin Acrylic adhesive resin (OH-139, Samsung SDI Co., Ltd.)

(B) Colorant dye (B-1) Compound of Synthesis Example 7-1 (compound represented by Chemical Formula 1-1) (B-2) Compound of Synthesis Example 7-2 (compound represented by Chemical Formula 1-2) (B-3) Compound of Synthesis Example 7-3 (compound represented by Chemical Formula 1-3) (B-4) Compound of Synthesis Example 7-4 (compound represented by Chemical Formula 1-4) (B-5) Synthesis Compound of Example 7-5 (Compound represented by Chemical Formula 1-5) (B-6) Synthesis of compound of Example 7-6 (Compound represented by Chemical Formula 1-6) (B-7) Synthesis of compound of Example 7-7 (Compounds represented by Chemical Formulas 1-7) (B-8) Compounds of Synthesis Example 7-8 (compounds represented by Chemical Formula 1-8) (B-9) Compounds of Synthesis Example 7-9 (compounded by Chemical Formula 1-9 (B-10) The compound of Synthesis Example 7-10 (the compound represented by Chemical Formula 1-10) (B-11) The compound of Synthesis Example 7-11 (the compound represented by Chemical Formula 1-11) (B -12) Compound of Synthesis Example 7-12 (compound represented by Chemical Formula 1-12) (B-13) Comparative compound of Synthesis Example 1 (compound represented by Chemical Formula C-1) Pigment dispersion (B-14) C.I Pigment Blue 15: 6 dispersion (GC1679, Sanyo (Sanyo)) (B-15) "blue 15: violet dye 6+" co-dispersing liquid (GC1207, Sanyo)

(C) Photopolymerizable monomer DPHA (Nippon Kayaku Co., Ltd.)

(D) Photopolymerization initiator oxime-based initiator (OXE01, BASF)

(E) Solvent Propylene glycol monomethyl ether acetate (PGMEA, Kyowa Co., Ltd.)

(F) Other additives Fluorine-based surfactants (F-554, DIC Co., Ltd.)

[Table 2] (Unit:% by weight)

[Table 3] (Unit:% by weight)

Evaluation 2: Measurement of brightness, heat resistance, and chemical resistance

The photosensitive resin compositions according to Examples 1 to 14 and Comparative Examples 1 to 4 were coated on a 1 mm thick degreased glass substrate to a thickness of 1 μm to 3 μm, and then at 90 ° C. It was dried on a hot plate for 2 minutes to obtain a film (250 rpm to 350 rpm). The film was exposed using a high-pressure mercury lamp (exposure condition: 50 mJ / cm ² ) with a main wavelength of 365 nm, and a 111-fold diluted KOH developing solution (washing solution / developing solution = 1 / 0.8) in a developer Development took 60 seconds. Subsequently, the film was dried in a forced convection drying oven at 230 ° C. for 20 minutes to obtain a color sample.

The brightness of the color samples (based on 0.1065) was measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.) (based on C light source), and the results are shown in Table 4.

The color samples were dried for another 60 minutes in a convection oven at 230 ° C, and the color difference between the color samples before and after drying was measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.) based on the C light source, and The heat resistance (DEab *) of the sample was then measured, and the results are shown in Table 4.

The color samples were precipitated in a methylpyrrolidone (NMP) solution at 80 ° C for 1 minute, and the absorbance of the methylpyrrolidone solution of the color samples was analyzed using UV-VIS spectroscopy to measure their resistance The chemical properties (resistance to elution) are shown in Table 4.

[Table 4]

Referring to Table 4, compared to a photosensitive resin composition that does not include a compound represented by Chemical Formula 1 as a dye or a compound that exceeds a range described below, the total amount of the photosensitive resin composition contains 5 to 20% by weight. The photosensitive resin composition having the compound represented by Chemical Formula 1 as a dye in an amount of 10%, for example, 10% to 15% by weight, exhibits excellent color characteristics, heat resistance, and chemical resistance.

Although the invention has been described in connection with exemplary embodiments that are currently considered to be practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather, the invention is intended to cover the patents included in the accompanying application The spirit of the scope and various modifications and equivalent arrangements within the scope.

no.

no.

Claims (19)

A compound represented by Chemical Formula 1: Wherein, in Chemical Formula 1, R ¹ is a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl, R ² is a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the limitation that the aryl group has at least one A substituent selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, and a substituted or unsubstituted C1 to C10 alkoxy group, and R ³ to R ^{5 are} independently substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy, or substituted or unsubstituted C6 to C20 aryl, m and n are independently integers in the range of 1 to 5 , And L is represented by one selected from Chemical Formula 3, Chemical Formula 4, and Chemical Formula 6: [Chemical Formula 3] Among them, in Chemical Formula 3, Chemical Formula 4, and Chemical Formula 6, R ⁶ is a substituted or unsubstituted amino group, or a substituted or unsubstituted fluorenyl group, and R ⁷ to R ^{9 are} independently a hydroxyl group or substituted or unsubstituted For substituted C1 to C10 alkyl, the restriction is that at least one of R ⁷ and R ⁸ is a hydroxyl group, and o and p are independently integers ranging from 1 to 3, and the restriction is 2 o + p 5 and q is an integer ranging from 0 to 4. The compound as described in claim 1 in the scope of patent application, wherein R ¹ is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl. The compound according to item 1 of the scope of patent application, wherein R ² is a substituted or unsubstituted adamantyl group, or a substituted or unsubstituted phenyl group, with the limitation that the phenyl group has at least one A substituent selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, and a substituted or unsubstituted C1 to C10 alkoxy group. The compound according to item 3 of the scope of patent application, wherein R ² is the unsubstituted adamantyl group or has at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, and The phenyl group of a substituent in a substituted or unsubstituted C1 to C10 alkoxy group. The compound according to item 1 of the scope of patent application, wherein R ³ to R ^{5 are} independently a substituted or unsubstituted C1 to C20 alkyl group. The compound according to item 1 of the scope of patent application, wherein the substituted or unsubstituted amino group is represented by Chemical Formula 8, and the substituted or unsubstituted fluorenyl group is represented by Chemical Formula 9: Wherein, in Chemical Formula 8, R ^x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5. The compound according to item 1 of the scope of patent application, wherein R ⁶ is a substituent represented by Chemical Formula 8 or a substituent represented by Chemical Formula 9, and R ⁷ to R ^{9 are} independently a hydroxyl group or a tert-butyl group. Is that at least one of R ⁷ and R ⁸ is a hydroxyl group: Wherein, in Chemical Formula 8, R ^x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5. The compound according to item 1 of the scope of patent application, wherein Chemical Formula 1 is represented by Chemical Formula 10-1 or Chemical Formula 10-2: [Chemical Formula 10-2] Among them, in Chemical Formulas 10-1 and 10-2, R ¹ is a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, and R ² Is a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the limitation that the aryl group has at least one selected from a halogen atom, a substituted Or unsubstituted C1 to C10 alkyl, and substituents in substituted or unsubstituted C1 to C10 alkoxy, and R ³ to R ^{5 are} independently substituted or unsubstituted C1 to C20 alkyl And L is represented by Chemical Formula 2, [Chemical Formula 2] ^* -L ¹ -A wherein, in Chemical Formula 2, L ¹ is -O (C = O)-, and A is a substituted phenyl group. The compound according to item 1 of the scope of patent application, wherein Chemical Formula 1 is represented by one selected from Chemical Formula 1-7, Chemical Formula 1-9, and Chemical Formula 1-10: [Chemical Formula 1-7] [Chemical Formula 1-9] [Chemical Formula 1-10] The compound as described in claim 1, wherein the compound represented by Chemical Formula 1 has a maximum absorbance in a wavelength range of 450 nm to 600 nm. A photosensitive resin composition comprising, as a dye, the compound according to any one of claims 1 to 10 of the scope of patent application. The photosensitive resin composition according to item 11 of the patent application scope, wherein the photosensitive resin composition further includes a binder resin, a pigment, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. The photosensitive resin composition according to item 11 of the scope of application for a patent, wherein the photosensitive resin composition contains 5% to 20% by weight based on the total amount of the photosensitive resin composition. The amount of the dye. The photosensitive resin composition according to item 13 of the scope of application for a patent, wherein the dye is contained in an amount of 10 to 15% by weight based on the total amount of the photosensitive resin composition. The photosensitive resin composition according to claim 12 in the application scope, wherein the pigment is a blue pigment. The photosensitive resin composition according to item 12 of the scope of application for a patent, wherein the adhesive resin includes an acrylic adhesive resin, a Cardo adhesive resin, or a combination thereof. The photosensitive resin composition according to item 12 of the scope of application for a patent, wherein the photosensitive resin composition includes 1 to 10% by weight of the adhesive based on the total amount of the photosensitive resin composition. Resin; 45% to 80% by weight of a coloring agent containing the dye and the pigment; 1% to 5% by weight of the photopolymerizable monomer; 0.1% to 3% by weight of the photopolymerization Initiator; and the balance of the solvent. The photosensitive resin composition according to item 11 of the scope of the patent application, wherein the photosensitive resin composition further comprises the following additives: malonic acid; 3-amino-1,2-propanediol; silane-based coupling agent; leveling Agent; fluorine-based surfactant; radical polymerization initiator; or a combination thereof. A color filter includes a photosensitive resin film manufactured using the photosensitive resin composition according to item 11 of the scope of patent application.