KR20180001068A - Novel compound, photosensitive resin composition comprising the same and color filter - Google Patents

Abstract

Provided are a compound represented by chemical formula 1, a photosensitive resin composition comprising the same and a color filter manufactured by using the photosensitive resin composition. In the chemical formula 1, each substituent is the same as defined in the specification. A compound of the present invention has excellent color properties so a photosensitive resin composition comprising the same can provide a color filter having excellent brightness, thermal resistance, processability, etc.

Description

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

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

The liquid crystal display device, which is one of the display devices, has advantages such as lightness, thinness, low cost, low power consumption driving and bonding with an excellent integrated circuit, and its use range is expanding for notebook computers, monitors and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and ITO pixel electrodes are formed, and an upper substrate on which an active circuit portion composed of a liquid crystal layer, a thin film transistor, and a capacitor layer and an ITO pixel electrode are formed. The color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate so as to shield the boundary between pixels and a plurality of colors (typically red (R), green (G), blue ) Are arrayed in a predetermined order, and the pixel portions are stacked in this order.

In the pigment dispersion method, which is one of the methods of implementing a color filter, a photosensitive resin composition containing a colorant is coated on a transparent substrate provided with a black matrix, a pattern of a shape to be formed is exposed, And a coloring thin film is formed by repeating a series of processes of thermosetting.

The photosensitive resin composition used in the production of the color filter according to the pigment dispersion method generally comprises 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 manufacture LCDs such as mobile phones, notebooks, monitors, and TVs.

However, in the pigment dispersion method, it is difficult to finely disperse the pigment powder and various additives are required because the dispersion state must be stable in the dispersion even when the pigment powder is dispersed, and the dispersing process is also very difficult. Further, There are disadvantages in that storage and transportation conditions are difficult to maintain the quality condition. In addition, in a color filter made of a pigment type photosensitive resin composition, there is a limit of brightness and contrast ratio resulting from the pigment particle size.

Accordingly, there has been a need to develop dyes having heat resistance and chemical resistance similar to those of pigments instead of pigments.

One embodiment is to provide a novel compound.

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

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

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

[Chemical Formula 1]

In Formula 1,

R ¹ 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 group,

R ² is a substituted or unsubstituted C 3 to C 20 alicyclic ring group or a substituted or unsubstituted C 6 to C 20 aryl group, provided that the aryl group is substituted with 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 alkylthio group,

R ³ to R ⁵ are each independently 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,

m and n are each independently an integer of 1 to 5,

L is represented by the following formula (2)

(2)

In Formula 2,

L ¹ is -O (C = O) - or -S-,

A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

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.

R ² may be a substituted or unsubstituted adamantyl group or a substituted or unsubstituted phenyl group. Provided that at least one substituent selected from the group consisting of 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 alkylthio group is substituted with a substituent Lt; / RTI >

R ² is an unsubstituted adamantyl group or a substituted or unsubstituted C 1 to C 10 alkylthio group, which may be substituted by a halogen atom, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 1 to C 10 alkoxy group, May be a phenyl group having as a substituent only at least one substituent selected from the group ".

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

The L may be represented by any one selected from the group consisting of the following formulas (3) to (7).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above 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 acyl group,

R ⁷ to R ⁹ are each independently a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, provided that at least one of R ⁷ and R ⁸ is a hydroxy group,

R ¹⁰ is a substituted or unsubstituted C1 to C10 alkyl group,

o and p are each independently an integer of 1 to 3, provided that 2? o + p? 5,

q is an integer of 0 to 4;

The substituted or unsubstituted amino group may be represented by the following general formula (8).

[Chemical Formula 8]

In Formula 8,

R ^x is a substituted or unsubstituted C1 to C10 alkyl group,

and z is an integer of 0 to 5.

The substituted or unsubstituted acyl group may be represented by the following general formula (9).

[Chemical Formula 9]

The R ⁶ may be a t-butyl group (tert-butyl group), a substituent represented by the formula (8) or a substituent represented by the formula (9).

Each of R ⁷ to R ⁹ independently represents a hydroxyl group or a t-butyl group (at least one of R ⁷ and R ⁸ may be a hydroxy group).

R ¹⁰ may be a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted pentyl group.

The formula (1) may be represented by the following formula (10-1) or (10-2).

[Formula 10-1]

[Formula 10-2]

In 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,

R ² is a substituted or unsubstituted C 3 to C 20 alicyclic ring group or a substituted or unsubstituted C 6 to C 20 aryl group, provided that the aryl group is substituted with 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 alkylthio group,

R ³ to R ⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

L is represented by the following formula (2)

(2)

In Formula 2,

L ¹ is -O (C = O) - and

A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, or a substituted or unsubstituted C6 to C20 aryl group.

The formula (1) may be represented by one of the following formulas (1-1) to (1-10).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

The compound represented by Formula 1 may be a dye.

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

Another embodiment provides a photosensitive resin composition comprising the above compound.

The photosensitive resin composition may further comprise a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

The photosensitive resin composition may further comprise a pigment.

The binder resin may include an acrylic binder resin, a cadmium binder resin, or a combination thereof.

The photosensitive resin composition may include malonic acid; 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine surfactants; A radical polymerization initiator; Or a combination thereof.

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

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

The color filter including the compound according to one embodiment is excellent, and when the photosensitive resin composition containing the compound is used, a color filter excellent in brightness, heat resistance, and processability can be provided.

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

Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Cl, Br or I), a hydroxyl group, a nitro group, a cyano group, an amino group NH _2, NH (R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently represent a C1 to C10 alkyl or C6 to C20 aryl group) Substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted alicyclic groups, A substituted aryl group, a substituted aryl group, and a substituted or unsubstituted heterocyclic group.

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

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

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

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

As used herein, the cadmium resin means a resin in which at least one functional group selected from the group consisting of the following formulas (11-1) to (11-11) is contained in the main backbone of the resin.

Unless otherwise defined herein, "*" means the same or different atom or moiety connected to a formula.

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

[Chemical Formula 1]

In 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 group,

R ² is a substituted or unsubstituted C 3 to C 20 alicyclic ring group or a substituted or unsubstituted C 6 to C 20 aryl group, provided that the aryl group is substituted with 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 alkylthio group,

R ³ to R ⁵ are each independently 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,

m and n are each independently an integer of 1 to 5,

L is represented by the following formula (2)

(2)

In Formula 2,

L ¹ is -O (C = O) - or -S-

A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

The compound according to one embodiment has the excellent spectroscopic characteristics and high molar extinction coefficient as compared with conventional dyes represented by the formula (1), and has excellent solubility in organic solvents such as cyclohexanone and PGMEA.

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, the heat resistance is lowered 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 group .

R ² may be a substituted or unsubstituted adamantyl group or a substituted or unsubstituted phenyl group. Provided that at least one substituent selected from the group consisting of 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 alkylthio group is substituted with a substituent Lt; / RTI >

For example, when R ² is a phenyl group substituted with a trifluoromethyl group, there is a problem that heat resistance is lowered as compared with the case where R ² is a phenyl group substituted with a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, or the like.

For example, R ² may be an unsubstituted adamantyl group or a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 1 to C 10 alkoxy group, Or a phenyl group having, as a substituent, at least one substituent selected from the group consisting of "

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

The L may be represented by any one selected from the group consisting of the following formulas (3) to (7).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above 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 acyl group,

R ⁷ to R ⁹ are each independently a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, provided that at least one of R ⁷ and R ⁸ is a hydroxy group,

R ¹⁰ is a substituted or unsubstituted C1 to C10 alkyl group,

o and p are each independently an integer of 1 to 3, provided that 2? o + p? 5,

q is an integer of 0 to 4;

For example, the substituted or unsubstituted amino group may be represented by the following general formula (8).

[Chemical Formula 8]

In Formula 8,

R ^x is a substituted or unsubstituted C1 to C10 alkyl group,

and z is an integer of 0 to 5.

For example, the substituted or unsubstituted acyl group may be represented by the following general formula (9).

[Chemical Formula 9]

For example, R ⁶ may be a t-butyl group (tert-butyl group), a substituent represented by the formula (8) or a substituent represented by the formula (9).

For example, each of R ⁷ to R ⁹ independently represents a hydroxyl group or a t-butyl group (at least one of R ⁷ and R ⁸ may be a hydroxy group).

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

In Formula 1, the position of R ¹ may be ortho, meta or para. For example, the position of R ¹ may be ortho or para, such as ortho. As the position of R ¹ is changed in the order of meta, para and ortho, luminance and heat resistance can be improved. That is a compound, the position of the R ¹ metadata (meta) of the position of the R ¹ p (para) of the compound, and the luminance and the heat resistance can be more excellent, the location is p (para) of the R ^1, rather than compound A compound in which the position of R < ¹ > is ortho may be more excellent in luminance and heat resistance.

For example, the compound represented by Formula 1 may be a compound represented by Formula 10-1 or a compound represented by Formula 10-2.

[Formula 10-1]

[Formula 10-2]

In 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,

R ² is a substituted or unsubstituted C 3 to C 20 alicyclic ring group or a substituted or unsubstituted C 6 to C 20 aryl group, provided that the aryl group is substituted with 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 alkylthio group,

R ³ to R ⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

L is represented by the following formula (2)

(2)

In Formula 2,

L ¹ is -O (C = O) - and

A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, or a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by the formula (1) may be represented by any one selected from the group consisting of a compound represented by the following formula (1-1) to a compound represented by the following formula (1-10).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

The compounds according to one embodiment are represented by the above formula (1), so that a clearer color can be expressed with a small amount, and a display device having excellent color characteristics such as luminance and contrast ratio can be manufactured when used as a colorant. For example, the compound may be a colorant, such as a dye, such as a blue or violet dye, for example a dye having a maximum absorbance in the wavelength range of 300 nm to 450 nm.

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

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

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

For example, the photosensitive resin composition may further comprise a pigment.

The compound according to one embodiment acts as a coloring agent such as a dye, for example, a blue or violet dye in the photosensitive resin composition, and can exhibit excellent color characteristics.

The pigments may include, but are not limited to, yellow pigments, green pigments, red pigments, blue pigments, violet pigments, or combinations thereof. For example, the pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.

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

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

As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, and alkylamines. These may be used singly or in combination of two or more.

DISPERBYK-161, DISPERBYK-160, DISPERBYK-161, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160 and DISPERBYK-160 of BYK Co., -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.

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

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

The pigment dispersion may be contained in an amount of 5% by weight to 30% by weight, for example, 10% by weight to 25% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous in securing a process margin and excellent color reproduction ratio and contrast ratio.

The binder resin may be an acrylic binder resin, a carcass binder resin, or a combination thereof.

The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and may be a resin containing at least one acrylic repeating unit.

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

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

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.

Specific examples of the acrylic binder resin include polybenzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate (Meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited thereto, and they may be used alone or in combination of two or more. Two or more kinds may be used in combination.

The weight average molecular weight of the acrylic binder resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the acrylic binder resin is within the above range, the photosensitive resin composition is excellent in physical and chemical properties, has an appropriate viscosity, and is excellent in adhesion to a substrate during the production of a color filter.

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

The cadmium binder resin may include a repeating unit represented by the following formula (11).

(11)

In Formula 11,

R ¹¹ and R ¹² are each independently a hydrogen atom or a substituted or unsubstituted (meth) acryloyloxyalkyl group,

R ¹³ and R ¹⁴ are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

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 each independently a hydrogen atom or a substituted or unsubstituted C 1 to C 20 alkyl group) Is any one of the linking groups represented by formulas (11-1) to (11-11)

[Formula 11-1]

[Formula 11-2]

[Formula 11-3]

[Formula 11-4]

[Formula 11-5]

(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.

[Formula 11-6]

[Formula 11-7]

[Formula 11-8]

[Formula 11-9]

[Chemical Formula 11-10]

[Formula 11-11]

Z ² is an acid anhydride residue,

m1 and m2 are each independently an integer of 0 to 4;

The cadmium-based binder resin may include a functional group represented by the following formula (12) in at least one of the two terminals.

[Chemical Formula 12]

In Formula 12,

Z ³ may be represented by the following formulas (12-1) to (12-7).

[Formula 12-1]

(Wherein R ^b and R ^c are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group or an ether group).

[Formula 12-2]

[Formula 12-3]

[Chemical Formula 12-4]

[Formula 12-5]

(Wherein R ^d is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, a C1 to C20 alkylamine group, or a C2 to C20 alkenylamine group).

[Chemical Formula 12-6]

[Chemical Formula 12-7]

Examples of the cationic binder resin include fluorene-containing compounds such as 9,9-bis (4-oxiranylmethoxyphenyl) fluorene; Benzene tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutanetetracarboxylic dianhydride, perylenetetracarboxylic dianhydride , Tetrahydrofuran tetracarboxylic acid dianhydride, tetrahydrophthalic anhydride and the like; Glycol compounds such as ethylene glycol, propylene glycol, and polyethylene glycol; Alcohol compounds such as methanol, ethanol, propanol, n-butanol, cyclohexanol and benzyl alcohol; Propylene glycol methyl ethyl acetate, and N-methyl pyrrolidone; Phosphorus compounds such as triphenylphosphine; And an amine or an ammonium salt compound such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, benzyltriethylammonium chloride, or the like.

In the case of the cadmium-based binder resin, the developability is low, and when the color filter is manufactured using the photosensitive resin composition containing the cadmium-based binder resin, it is difficult to control the developability of the pattern. In this case, the developability of the pattern can be controlled by using the above-mentioned acrylic binder resin together with the cadmium-based binder resin as a binder resin.

Furthermore, when the cationic binder resin is used together with the acrylic binder resin described above, a photosensitive resin composition having excellent adhesion and high resolution and high brightness characteristics can be obtained.

The weight average molecular weight of the cationic binder resin may be from 500 g / mol to 50,000 g / mol, such as from 3,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the cationic binder resin is within the above range, pattern formation is good without residue in the production of a color filter, no loss of film thickness during development, and good patterns can be obtained.

The cadmium binder resin may have an acid value of from 100 mgKOH / g to 140 mgKOH / g.

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

Since the photopolymerizable monomer has the ethylenically unsaturated double bond, sufficient polymerization is caused during exposure in the pattern formation step, whereby a pattern having excellent heat resistance, light resistance and chemical resistance can be formed.

Specific examples of the photopolymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol Acrylate such as 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 tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di Acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol There may be mentioned furnace methyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolak epoxy (meth) acrylate, and the like.

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

The photopolymerizable monomer may be treated with an acid anhydride to give better developing properties.

The photopolymerization initiator is an initiator generally used in a photosensitive resin composition, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, a oxime compound, Can be used.

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

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

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

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

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

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

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

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

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

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

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

The photosensitive resin composition according to one embodiment may contain at least one selected from the group consisting of malonic acid, malonic acid, and malonic acid to prevent spots and spots upon application, improve leveling performance, 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine surfactants; A radical polymerization initiator; Or a combination thereof, and the like.

Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatopropyltriethoxysilane,? -Glycidoxypropyltrimethoxysilane, and? - (3,4-epoxycyclohexyl) ethyltrimethoxysilane. These may be used singly or in combination of two or more.

Examples of the fluorine-based surfactant, BM Chemie Corporation ^{BM-1000 ®, BM-1100} ® , and the like; Mecha Pack F 142D ^® , Copper F 172 ^® , Copper F 173 ^® , Copper F 183 ^® and the like manufactured by Dainippon Ink & Chemicals Incorporated; M. Sumitomo Co., Inc. Pro rod FC-135 ^®, the same FC-170C ^®, copper FC-430 ^®, the same FC-431 ^®, and the like; Asahi Grass Co., Inc. Saffron S-112 ^®, the same S-113 ^®, the same S-131 ^®, the same S-141 ^®, the same S-145 ^®, and the like; Toray Silicone Co., Ltd.'s SH-28PA ^{®, ®} -190 copper, may be a commercially available product such as copper ^{-193 ®, SZ-6032 ®,} SF-8428 ®.

The content of the additive can be easily adjusted according to desired properties.

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

Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

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

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

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

Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.

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

(Synthesis of Compound)

Synthetic example  1-1: Synthesis of Compound Represented by Formula 2-1

2-Bromo-2-methoxyacetophenone (1 mole) was added to DMF (dimethylformamide, 250 ml) and stirred at room temperature. Phthalimide potassium (0.95 mol) was added to the reaction solution, followed by stirring for 3 hours. After completion of the reaction, the reaction product was precipitated by using 2500 ml of water, followed by filtration and drying to obtain the compound represented by the above formula (2-1). (Yield: 78%).

Synthetic example  1-2: Synthesis of Compound Represented by Formula 2-2

[Formula 2-2]

2-Bromo-4'-methoxyacetophenone was synthesized as a starting material in the same manner as in Synthesis Example 1-1 to obtain the compound represented by Formula 2-2. (Yield: 75.6%).

Synthetic example  1-3: Synthesis of Compound Represented by Formula 2-3

[Formula 2-3]

2-Bromo-2'-chloroacetophenone was synthesized as a starting material in the same manner as in Synthesis Example 1-1 to obtain the compound represented by Formula 2-3. (Yield: 74.5%).

Synthetic example  1-4: Synthesis of Compound Represented by Formula 2-4

[Chemical Formula 2-4]

2-Bromo-4'-chloroacetophenone was synthesized as a starting material in the same manner as in Synthesis Example 1-1 to obtain the compound represented by Formula 2-4. (Yield: 78.4%).

Synthetic example  1-5: Synthesis of Compound Represented by Formula 2-5

[Chemical Formula 2-5]

2-Bromo-4'-phenylacetophenone was synthesized as a starting material in the same manner as in Synthesis Example 1-1 to obtain the compound represented by Formula 2-5. (Yield: 76.8%)

Synthetic example  1-6: Synthesis of Compound Represented by Formula 2-6

[Chemical Formula 2-6]

2-Bromoacetophenone was synthesized as a starting material in the same manner as in Synthesis Example 1-1 to obtain the compound represented by Formula 2-6. (Yield: 81.5%).

Synthetic example  2: Synthesis of Compound Represented by Formula 3-1

Cyanoacetic acid (1.46 mol) and 2,6-di-tert-butyl-4-methylcyclohexanol (1.33 mol) were added to toluene (500 ml) and stirred at room temperature. Pyridine (1.59 mol) was added to this reaction solution and stirred. Acetic anhydride (2.65 mol) was added to this solution and stirred for 6 hours to complete the reaction. The reaction solution was washed twice with a 10% hydrochloric acid aqueous solution (500 g) and then twice with an aqueous sodium chloride solution (500 g). Water was removed with magnesium sulfate, followed by filtration and drying to obtain the compound represented by Formula 3-1. (Yield: 62.5%).

Synthetic example  3-1: Synthesis of Compound Represented by Formula 4-1

The compound represented by the formula (2-1) (3.8 mol) and the compound represented by the formula (3-1) (4.15 mol) were added to a mixture of methanol (10 ml) and water (10 ml) and stirred. A 48% aqueous solution of sodium hydroxide (8.36 mol) was added dropwise to the reaction solution, the temperature was raised to 70 캜 and the mixture was stirred for 3 hours. After the reaction was monitored by TLC, the reaction was completed. The solution was cooled to room temperature, filtered, washed with water and hexane, and dried to obtain the compound represented by Formula 4-1. (Yield: 69%).

Synthetic example  3-2: Synthesis of Compound Represented by Formula 4-2

[Formula 4-2]

The compound represented by Formula 2-2 was synthesized as a starting material in the same manner as Synthesis Example 3-1 to obtain the compound represented by Formula 4-2. (Yield: 71.8%)

Synthetic example  3-3: Synthesis of Compound Represented by Formula 4-3

[Formula 4-3]

The compound represented by Formula 2-3 was synthesized as a starting material in the same manner as Synthesis Example 3-1 to give the compound represented by Formula 4-3. (Yield: 70.2%).

Synthetic example  3-4: Synthesis of Compound Represented by Formula 4-4

[Formula 4-4]

The compound represented by Formula 2-4 was synthesized as a starting material in the same manner as Synthesis Example 3-1 to give the compound represented by Formula 4-4. (Yield: 69.2%).

Synthetic example  3-5: Synthesis of Compound Represented by Formula 4-5

[Formula 4-5]

The compound represented by Formula 2-5 was synthesized as a starting material in the same manner as Synthesis Example 3-1 to obtain the compound represented by Formula 4-5. (Yield: 70.1%).

Synthetic example  3-6: Synthesis of Compound Represented by Formula 4-6

[Formula 4-6]

The compound represented by Formula 2-6 was synthesized as a starting material in the same manner as Synthesis Example 3-1 to give the compound represented by Formula 4-6. (Yield: 73.4%)

Synthetic example  4-1: Synthesis of Compound Represented by Formula 5-1

The compound represented by the formula (4-1) (0.38 mol) was added to acetic acid (800 g) and stirred at room temperature. Triethyl orthoformate (0.23 mol) was added to the reaction solution, and the mixture was heated to 130 캜 and stirred for 10 hours. After completion of the reaction, the reaction mixture was filtered with acetonitrile (100 g), and then acetonitrile (100 g) was added and stirred. This solution was filtered, washed with acetonitrile (100 g) and dried to obtain the compound represented by the above formula (5-1). (Yield: 68.7%).

Synthetic example  4-2: Synthesis of Compound Represented by Formula 5-2

[Formula 5-2]

The compound represented by Formula 4-2 was synthesized as a starting material in the same manner as in Synthesis Example 4-1 to obtain the compound represented by Formula 5-2. (Yield: 70.4%).

Synthetic example  4-3: Synthesis of Compound Represented by Formula 5-3

[Formula 5-3]

The compound represented by Formula 4-3 was synthesized as a starting material in the same manner as Synthesis Example 4-1 to obtain the compound represented by Formula 5-3. (Yield: 69.6%).

Synthetic example  4-4: Synthesis of Compound Represented by Formula 5-4

[Formula 5-4]

The compound represented by Formula 4-4 was synthesized as a starting material in the same manner as Synthesis Example 4-1 to obtain the compound represented by Formula 5-4. (Yield: 71.9%).

Synthetic example  4-5: Synthesis of Compound Represented by Formula 5-5

[Formula 5-5]

The compound represented by Formula 4-5 was synthesized as a starting material in the same manner as Synthesis Example 4-1 to give the compound represented by Formula 5-5. (Yield: 74.2%).

Synthetic example  4-6: Synthesis of Compound Represented by Formula 5-6

[Formula 5-6]

The compound represented by Formula 4-6 was synthesized as a starting material in the same manner as Synthesis Example 4-1 to obtain the compound represented by Formula 5-6. (Yield: 72.8%).

Synthetic example  5-1: Synthesis of Compound Represented by Formula 6-1

The compound of formula 5-1 was added to toluene (17 ml) and stirred. Sodium hydroxide (40% aqueous solution, 0.036 mmol) was added dropwise to the solution. Then, TBAB (0.0012 mmol of tetrabutylammonium bromide) was added thereto at room temperature, and the mixture was stirred for 30 minutes, and the temperature of the reaction solution was lowered to 0 ° C using an ice bath. To the reaction solution was added 1-adamantanecarbonyl chloride (0.072 mmol). After removing the ice bath, the reaction was completed after stirring for 2 hours while raising the temperature to room temperature. Washed with 100 ml of water and 100 ml of ethyl acetate, and dried to obtain the compound represented by the above formula (6-1). (Yield: 72.5%).

Synthetic example  5-2: Synthesis of Compound Represented by Formula 6-2

[Formula 6-2]

The compound represented by Formula 5-1 and 4-methoxy-2-methylbenzoyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-2. (Yield: 74.2%).

Synthetic example  5-3: Synthesis of Compound Represented by Formula 6-3

[Formula 6-3]

The compound represented by the formula 5-2 and 1-adamantanecarbonyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by the above Formula 6-3. (Yield: 74.5%).

Synthetic example  5-4: Synthesis of Compound Represented by Formula 6-4

[Formula 6-4]

The compound represented by Formula 5-2 and 4-methoxy-2-methylbenzoyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-4. (Yield: 78.2%).

Synthetic example  5-5: Synthesis of Compound Represented by Formula 6-5

[Formula 6-5]

The compound represented by Formula 5-4 and 1-adamantanecarbonyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-5. (Yield: 72.6%).

Synthetic example  5-6: Synthesis of Compound Represented by Formula 6-6

[Formula 6-6]

The compound represented by Formula 5-5 and 1-adamantanecarbonyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-6. (Yield: 70.4%).

Synthetic example  5-7: Synthesis of Compound Represented by Formula 6-7

[Formula 6-7]

The compound represented by Formula 5-5 and 4-methoxy-2-methylbenzoyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-7. (Yield: 74.6%).

Synthetic example  5-8: Synthesis of Compound Represented by Formula 6-8

[Formula 6-8]

The compound represented by Formula 5-5 and 2-Methoxybenzoyl chloride were synthesized in the same manner as Synthesis Example 5-1 as a starting material to obtain the compound represented by Formula 6-8. (Yield: 75.1%).

Synthetic example  5-9: Synthesis of Compound Represented by Formula 6-9

[Formula 6-9]

The compound represented by Formula 5-5 and 2- (Methylthio) benzoyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-9. (Yield: 72.3%).

Synthetic example  5-10: Synthesis of Compound Represented by Formula 6-10

[Chemical Formula 6-10]

The compound represented by Formula 5-6 and 4-methoxy-2-methylbenzoyl chloride were synthesized in the same manner as in Synthesis Example 5-1 to obtain the compound represented by Formula 6-10. (Yield: 72.3%).

Synthetic example  6-1: Synthesis of Compound Represented by Formula 7-1

4-tert-Butylbenzoic acid (0.14 mol) and sodium methoxide (30% methanol solution, 0.14 mol) were added to a mixed solution of water (60 ml) / methanol (90 ml) and stirred. To this solution was added zinc sulfate heptahydrate (0.06 mol). The reaction was completed by stirring at room temperature for 1 hour. After the reaction, the mixture was filtered and washed with 1000 ml of water and 1000 ml of methanol to obtain a compound represented by the above formula (7-1). (Yield: 90.1%).

Synthetic example  6-2: Synthesis of Compound Represented by Formula 7-2

[Formula 7-2]

2- (2,3-Dimethylphenylamino) benzoic acid was synthesized as a starting material in the same manner as in Synthesis Example 6-1 to give the compound represented by Formula 7-2. (Yield: 93.3%).

Synthetic example  7-1: Synthesis of Compound Represented by Formula 1-1

Compound (6-1) (0.642 mmol) and compound (7-1) (0.835 mmol) were added to ethanol (10 ml) and stirred at room temperature. The reaction was confirmed with TCL and completed. Ethanol in the reaction solution was dried, washed with 100 ml of methylene chloride and 100 ml of water, and dried to obtain the compound represented by Formula 1-1. (Yield: 81.7%, Maldi tof Mass: 1454.8)

Synthetic example  7-2: Synthesis of Compound Represented by Formula 1-2

[Formula 1-2]

Maldi tof Mass: 1426.7

The compound represented by formula (6-4) and the compound represented by formula (7-1) were synthesized in the same manner as in synthesis example 7-1 to give the compound represented by formula (1-2). (Yield: 82.8%)

Synthetic example  7-3: Synthesis of Compound Represented by Formula 1-3

[Formula 1-3]

Maldi tof Mass: 1465.7

The compound represented by the formula (6-5) and the compound represented by the formula (7-1) were synthesized in the same manner as in Synthesis Example 7-1, thereby obtaining the compound represented by the above Formula 1-3. (Yield: 84.1%).

Synthetic example  7-4: Synthesis of Compound Represented by Formula 1-4

[Formula 1-4]

Maldi tof Mass: 1547.9

The compound represented by Formula 6-6 and the compound represented by Formula 7-1 were synthesized in the same manner as in Synthesis Example 7-1, to obtain the compound represented by Formula 1-4. (Yield: 87.2%).

Synthetic example  7-5: Synthesis of Compound Represented by Formula 1-5

[Formula 1-5]

Maldi tof Mass: 1491.7

The compound represented by the formula (6-8) and the compound represented by the formula (7-1) were synthesized in the same manner as in Synthesis Example 7-1 to obtain the compound represented by the above formula (1-5). (Yield: 82.2%).

Synthetic example  7-6: 1- To 6  Synthesis of displayed compounds

[Chemical Formula 1-6]

Maldi tof Mass: 1522.67

The compound represented by Formula 6-9 and the compound represented by Formula 7-1 were synthesized in the same manner as in Synthesis Example 7-1 as a starting material to obtain the compound represented by Formula 1-6. (Yield: 81.8%)

Synthetic example  7-7: Synthesis of a compound represented by the general formula 1-7

[Chemical Formula 1-7]

Maldi tof Mass: 1489.72

The compound represented by the formula (6-2) and the compound represented by the formula (7-2) were synthesized in the same manner as in Synthesis Example 7-1, thereby obtaining the compound represented by the above Formula 1-7. (Yield: 85.8%).

Synthetic example  7-8: Synthesis of Compound Represented by Formula 1-8

[Chemical Formula 1-8]

Maldi tof Mass: 1454.81

The compound represented by the formula (6-3) and the compound represented by the formula (7-1) were synthesized in the same manner as in Synthesis Example 7-1 to give the compound represented by the above Formula 1-8. (Yield: 82.3%).

Synthetic example  7-9: Synthesis of a compound represented by the general formula 1-9

[Chemical Formula 1-9]

Maldi tof Mass: 1541.49

The compound represented by Formula 6-7 and the compound represented by Formula 7-2 were synthesized in the same manner as in Synthesis Example 7-1 as a starting material to obtain the compound represented by Formula 1-9. (Yield: 84.3%).

Synthetic example  7-10: Synthesis of Compound Represented by Formula 1-10

[Chemical Formula 1-10]

Maldi tof Mass: 1569.52

The compound represented by Formula 6-8 and the compound represented by Formula 7-2 were synthesized in the same manner as in Synthesis Example 7-1 as a starting material to obtain the compound represented by Formula 1-10. (Yield: 80.6%).

compare Synthetic example  1: Synthesis of Compound Represented by Formula C-1

[Chemical formula C-1]

Maldi tof Mass: 1366.69

The compound represented by formula (6-10) and the compound represented by formula (7-1) were synthesized in the same manner as in synthesis example 7-1 to give the compound represented by formula (C-1). (Yield: 78.6%).

Evaluation 1: Measurement of solubility

A diluting solvent (Anone) was added to 0.5 g of the compound synthesized in Synthesis Examples 7-1 to 7-10 and Comparative Synthesis Example 1, and the solution was added to 25 (25 g) of the solution by a mix rotor (MIXROTAR VMR-5, After stirring at 100 rpm for 1 hour, the solubility of each compound was determined. The results are shown in Table 1 below. (Anone means cyclohexanone.)

Solubility evaluation criteria

2.5% by weight or more of the compound (solute) dissolved in the total amount of the diluting solvent: ○

Less than 2.5% by weight of compound (solute) dissolved in total diluent solvent Dissolution: X

(Unit: wt%) Solubility Synthesis Example 7-1 ○ Synthesis Example 7-2 ○ Synthesis Example 7-3 ○ Synthesis Example 7-4 ○ Synthesis Example 7-5 ○ Synthesis Example 7-6 ○ Synthesis Example 7-7 ○ Synthesis Example 7-8 ○ Synthesis Example 7-9 ○ Synthesis Examples 7-10 ○ Comparative Synthesis Example 1 X

It can be seen from Table 1 that the compounds of Synthesis Examples 7-1 to 7-10 which are the compounds according to one embodiment are superior in solubility to the organic solvent in comparison with the compound of Comparative Synthesis Example 1, It can be confirmed that the characteristics can be expressed.

(Synthesis of photosensitive resin composition)

Example  One

The photosensitive resin composition according to Example 1 was prepared by mixing the following components in the compositions shown in Table 2 below.

Specifically, a photopolymerization initiator was dissolved in a solvent, followed by stirring at room temperature for 2 hours. Then, a binder resin and a photopolymerizable compound were added thereto, followed by stirring at room temperature for 2 hours. Subsequently, the compound obtained in Synthesis Example 7-1 (compound represented by Formula 1-1) as a colorant was added to the obtained reaction product and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: wt%) Ingredients content Colorant (dye) The compound of Synthesis Example 7-1 5.0 Binder resin (A) / (B) = 15/85 (w / w)
Molecular weight (Mw) = 22,000 g / mol
(A): methacrylic acid
(B): benzyl methacrylate 3.0 Photopolymerizable compound Dipentaerythritol hexaacrylate (DPHA) 7.0 Photopolymerization initiator 1,2-octanedione 1.0 menstruum PGMEA (Propylene Glycol Monomethyl Ether Acetate) 84.0 Total 100.00

Example  2

Except that the compound of Synthesis Example 7-2 (the compound represented by Formula 1-2) was used instead of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1) was used instead of the compound of Synthesis Example 7-1, To prepare a resin composition.

Example  3

Except that the compound of Synthesis Example 7-3 (the compound represented by Formula 1-3) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1) To prepare a resin composition.

Example  4

Except that the compound of Synthesis Example 7-4 (the compound represented by Formula 1-4) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1) was used, To prepare a resin composition.

Example 5

Except that the compound of Synthesis Example 7-5 (the compound represented by Formula (1-5)) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula (1-1)), To prepare a resin composition.

Example  6

The procedure of Example 1 was repeated except that the compound of Synthesis Example 7-6 (the compound of Formula 1-6) was used in place of the compound of Synthesis Example 7-1 (the compound of Formula 1-1) To prepare a resin composition.

Example  7

Except that the compound of Synthesis Example 7-7 (compound represented by Formula 1-7) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1), the photosensitive To prepare a resin composition.

Example  8

Except that the compound of Synthesis Example 7-8 (compound represented by Formula 1-8) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1) was used instead of the compound of Synthesis Example 7-1 To prepare a resin composition.

Example  9

Except that the compound of Synthesis Example 7-9 (the compound represented by Formula 1-9) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1) was used, To prepare a resin composition.

Example  10

Except that the compound of Synthesis Example 7-10 (the compound represented by Formula 1-10) was used in place of the compound of Synthesis Example 7-1 (the compound represented by Formula 1-1) To prepare a resin composition.

Comparative Example  One

Except that the compound of Comparative Synthesis Example 1 (the compound represented by the formula C-1) was used instead of the compound of Synthesis Example 7-1 (the compound represented by the Formula 1-1), the photosensitive resin A composition was prepared.

Evaluation 2: Color coordinates , Brightness and contrast ratio

The photosensitive resin composition prepared in Examples 1 to 10 and Comparative Example 1 was coated on a 1 mm thick glass substrate having a thickness of 1 mu m to 3 mu m and then dried on a hot plate at 90 DEG C for 2 minutes And dried to obtain a coating film. Subsequently, a coating film was obtained by exposure using a high-pressure mercury lamp having a dominant wavelength of 365 nm. And dried in a hot air circulating drying oven at 200 ° C for 5 minutes. The color layer (x, y), luminance (Y), and contrast ratio were measured using a spectrophotometer (MCPD3000, Otsuka electronic Co.)

Luminance (Y) Example 1 10.61 Example 2 10.85 Example 3 10.61 Example 4 10.83 Example 5 10.81 Example 6 10.80 Example 7 10.67 Example 8 10.81 Example 9 10.79 Example 10 10.62 Comparative Example 1 10.59

From Table 3, it can be seen that the photosensitive resin compositions of Examples 1 to 10 containing the compound according to one embodiment as a dye exhibited color characteristics superior to those of the photosensitive resin composition of Comparative Example 1, have.

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

Claims (18)

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

In 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 group,
R ² is a substituted or unsubstituted C 3 to C 20 alicyclic ring group or a substituted or unsubstituted C 6 to C 20 aryl group, provided that the aryl group is substituted with 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 alkylthio group,
R ³ to R ⁵ are each independently 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,
m and n are each independently an integer of 1 to 5,
L is represented by the following formula (2)
(2)

In Formula 2,
L ¹ is -O (C = O) - or -S-
A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.
The method according to claim 1,
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 group.
The method according to claim 1,
Wherein R ² is a substituted or unsubstituted adamantyl group or a substituted or unsubstituted phenyl group, provided that the phenyl group is substituted with a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, A substituted or unsubstituted C1 to C10 alkylthio group as a substituent.
The method of claim 3,
Wherein R ² is an unsubstituted adamantyl group or a substituted or unsubstituted C 1 to C 10 alkylthio group which may be substituted by a halogen atom, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 1 to C 10 alkoxy group, ≪ / RTI > is a phenyl group having as a substituent only at least one substituent selected from the group < RTI ID = 0.0 >
The method according to claim 1,
And R ³ to R ⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group.
The method according to claim 1,
Wherein L is any one selected from the group consisting of the following formulas (3) to (7):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above 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 acyl group,
R ⁷ to R ⁹ are each independently a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, provided that at least one of R ⁷ and R ⁸ is a hydroxy group,
R ¹⁰ is a substituted or unsubstituted C1 to C10 alkyl group,
o and p are each independently an integer of 1 to 3, provided that 2? o + p? 5,
q is an integer of 0 to 4;
The method according to claim 6,
Wherein the substituted or unsubstituted amino group is represented by the following general formula (8), and the substituted or unsubstituted acyl group is represented by the following general formula (9):
[Chemical Formula 8]

[Chemical Formula 9]

In Formula 8,
R ^x is a substituted or unsubstituted C1 to C10 alkyl group,
and z is an integer of 0 to 5.
The method according to claim 6,
R ⁶ is a t-butyl group (tert-butyl group), a substituent represented by the following formula (8) or a substituent represented by the following formula (9)
Each of R ⁷ to R ⁹ is independently a hydroxy group or a t-butyl group (at least one of R ⁷ and R ⁸ is a hydroxy group,
R ¹⁰ is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group or a substituted or unsubstituted pentyl group;
[Chemical Formula 8]

[Chemical Formula 9]

In Formula 8,
R ^x is a substituted or unsubstituted C1 to C10 alkyl group,
and z is an integer of 0 to 5.
The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 10-1 or 10-2:
[Formula 10-1]

[Formula 10-2]

In 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,
R ² is a substituted or unsubstituted C 3 to C 20 alicyclic ring group or a substituted or unsubstituted C 6 to C 20 aryl group, provided that the aryl group is substituted with 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 alkylthio group,
R ³ to R ⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
L is represented by the following formula (2)
(2)

In Formula 2,
L ¹ is -O (C = O) - and
A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, or a substituted or unsubstituted C6 to C20 aryl group.
The method according to claim 1,
(1) is represented by any one of the following formulas (1-1) to (1-10).
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

[Chemical Formula 1-9]

[Chemical Formula 1-10]

The method according to claim 1,
Wherein the compound represented by Formula 1 is a dye.
12. The method of claim 11,
Wherein the dye has a maximum absorbance in a wavelength range of 450 nm to 600 nm.
A photosensitive resin composition comprising the compound of any one of claims 1 to 12.
14. The method of claim 13,
Wherein the photosensitive resin composition further comprises a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.
15. The method of claim 14,
Wherein the photosensitive resin composition further comprises a pigment.
14. The method of claim 13,
Wherein the binder resin comprises an acrylic binder resin, a carcass binder resin or a combination thereof.
15. The method of claim 14,
The photosensitive resin composition may include malonic acid; 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine surfactants; A radical polymerization initiator; Or a combination thereof. ≪ / RTI >
A color filter produced by using the photosensitive resin composition of claim 13.