TW201321802A - Photosensitive resin composition for color filter and color filter prepared by using the same - Google Patents

Abstract

This disclosure relates to a photosensitive resin composition for a color filter and a color filter manufactured using the same. The photosensitive resin composition for a color filter according to the present invention includes dye having specific spectral characteristics together with pigment, and thereby, a color filter manufactured using the same has excellent light transmittance, luminance, contrast, and color purity, and improved heat resistance.

Description

Photosensitive resin composition for color filter and color filter made using the same sheet

The present invention relates to a photosensitive resin composition for a color filter and a color filter made using the composition.

The color filter is used for a liquid crystal display, an organic light-emitting device, an optical filter of a camera, etc., and the color filter is usually subjected to staining, printing, electrodeposition, Manufactured by methods such as pigment dispersion.

The most common method of the pigment dispersion method described above is to disperse the pigment in a composition having a sensitivity in the wavelength range of 200 to 400 nm, and then to fabricate a color filter by a mask etching method.

Since the aforementioned pigment dispersion method uses a pigment and is stable to light or heat, a color filter can be produced by a relatively simple process. Further, the pigment dispersion method can control brightness and contrast by reducing the particle diameter of the pigment and controlling the dispersion.

However, in the pigment dispersion method, if the pigment content is increased to increase the color purity, the brightness and contrast may be relatively lowered, and the aforementioned problems cannot be solved only by controlling the particle diameter of the pigment.

Therefore, as a method for overcoming the limitations of the aforementioned pigment dispersion method, a method of using a dye instead of a pigment has been proposed.

However, since the dye is hardly soluble in the solvent, the usable content of the dye is limited. Although it has been suggested to increase the dye content by, for example, improving the solubility of the dye, when the dye content is high, the dye may precipitate after baking. Or the problem that the heat resistance may be lowered to lower the light transmittance still exists.

Accordingly, it is an object of the present invention to provide a photosensitive resin composition which can produce a color filter having excellent light transmittance, brightness, contrast, and color purity and having good heat resistance.

Another object of the present invention is to provide a color filter made using the foregoing composition.

According to an embodiment of the present invention, there is provided a photosensitive resin composition for a color filter comprising an adhesive resin; a reactive unsaturated compound; a blue pigment; having a wavelength range of 430 to 465 nm a light transmittance equal to or higher than 90%, and a light having a light transmittance equal to or lower than 55% in a wavelength range of 495 to 505 nm; a polymerization initiator; and a solvent.

According to another embodiment of the present invention, there is provided a photosensitive resin composition for a color filter comprising an adhesive resin; a reactive unsaturated compound; a green pigment; having a wavelength range of 530 to 540 nm a light transmittance equal to or higher than 95%, and a dye having a light transmittance equal to or lower than 55% in a wavelength range of 580 to 590 nm; a polymerization initiator; and a solvent.

In the composition of the above embodiment, the dye may be a compound represented by the following Chemical Formula 1: [Chemical Formula 1]

In the chemical formula 1, M is copper, cobalt, aluminum, zinc, nickel, platinum or chromium; N is nitrogen; and R ¹ to R ¹⁶ are each independently a hydrogen atom, a halogen atom, a carboxyl group, a hydroxyl group, a sulfonic acid group, a heterocyclic group-substituted sulfonic acid alkyl group, a sulfonic acid hydroxyl group, a sulfonic acid alkoxy group, a sulfonic acid aryl group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a carbon number of 6 to 20 An aryl group, a heteroalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

The dye may preferably be a compound represented by the following Chemical Formula 2: [Chemical Formula 2]

In the chemical formula 2, M is copper, cobalt, aluminum, zinc, nickel, platinum or chromium; N is nitrogen; O is oxygen; and R ^a to R ^h are each independently an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group of 3 to 20, an aryl group having 6 to 20 carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

Further, a dye having a light transmittance equal to or higher than 90% in a wavelength range of 430 to 465 nm, and a spectral characteristic having a light transmittance equal to or lower than 55% in a wavelength range of 495 to 505 nm is preferably selected. From Octa(2-ethylhexyloxy)Cu Phthalocyanine, Octa(2-ethylhexyloxy)Co Phthalocyanine, eight (2-ethylhexyloxy) Al Phthalocyanine, Octa(2-ethylhexyloxy)Zn Phthalocyanine, Eight (2) -Ethylhexyloxy Ni Phthalocyanine, Octa(2-ethylhexyloxy)Pt Phthalocyanine, and Eight (2-B) At least one compound of the group consisting of octyloxy)chromocyanine (Octa(2-ethylhexyloxy)Cr Phthalocyanine).

Further, a dye having a light transmittance equal to or higher than 95% in a wavelength range of 530 to 540 nm, and a spectral characteristic having a light transmittance equal to or lower than 55% in a wavelength range of 580 to 590 nm is preferably selected. From octa (1,4,7,10-tetraoxaundecyl) copper phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl)Cu Phthalocyanine), eight (1,4,7,10-four Octa (1,4,7,10-tetraoxaundecyl)Co Phthalocyanine, octa (1,4,7,10-tetraoxaundecyl)aluminum phthalocyanine (Octa) (1,4,7,10-tetraoxaundecyl)Al Phthalocyanine), octa(1,4,7,10-tetraoxaundecyl)zinc phthalocyanine (Octa(1,4,7,10-tetraoxaundecyl)Zn Phthalocyanine, Oct (1,4,7,10-tetraoxaundecyl)Ni Phthalocyanine, eight (1,4,7,10) -Tetradodecyl)platinum phthalocyanine (Octa(1,4,7,10-tetraoxaundecyl)Pt Phthalocyanine) and octa(1,4,7,10-tetraoxaundecyl)chromium phthalocyanine At least one compound of the group consisting of (Octa (1,4,7,10-tetraoxaundecyl)Cr Phthalocyanine).

Meanwhile, the photosensitive resin composition for a color filter of the above embodiment may comprise: 100 to 250 parts by weight of a reactive unsaturated compound based on 100 parts by weight of the adhesive resin; and 5 to 150 parts by weight Pigment; 50 to 250 parts by weight of the dye; 5 to 50 parts by weight of the polymerization initiator; and 100 to 500 parts by weight of the solvent.

The adhesive resin may be a co-polymer having at least one selected from the group consisting of (meth)acrylic acid, itaconic acid, and maleic acid (from 10 to 40% by weight). Maleic acid), fumaric acid, vinyl acetic acid, 2-acryloyloxyethyl hydrogen phthalate, and hydrogen phthalate 2-propene oxime A olefinic group monomer in a group consisting of 2-acryloyloxypropyl hydrogen phthalate, and at least one of 60 to 90% by weight selected from isobutyl (meth)acrylate ), tert-butyl (meth)acrylate, lauryl (meth)acrylate, ste(meth)aryl acrylate (ste(meth)) Arylacrylate), Cyclohexyl (meth) acrylate, isobonyl (meth) acrylate, bezyl (meth) acrylate, (methyl) ) 2-hydroxyalkyl (meth)acrylate, trimethoxybutyl (meth)acrylate, ethylcarbitol (ethylcarbitol) Meth)acrylate), phenoxyethyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate,phenoxyethylene glycol (meth) Phenoxyethyleneglycol (meth)acrylate, 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl (meth)acrylate Meth)acrylate), 2-acryloxyethyl 2-hydroxypropyl(meth)phthalate, 2-hydroxy-3-phenoxy 2-hydroxy-3-phenoxypropyl (meth)acrylate, triethylsiloxyethyl (meth)acrylate, and ethyltriethyl Glycol A (meth) acrylate monomer in a group consisting of (ethyl) acrylate (ethyl) acrylate.

Moreover, the reactive unsaturated compound may be selected from the group consisting of ethylene glycol di(meth)acrylate, diethyleneglycol di(meth)acrylate. , triethyleneglycol di (meth)acrylate, propylene glycol di(meth)acrylate, 1,4-butanediol di(meth) 1,4-butandiol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate ) pentoxide (pentererythritol di (meth) acrylate), pentaerythritol tri Pentaerythritol tetra(meth)acrylate, pentaerythritol penta(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol II (meth) acrylate (dipentaerythritol di(meth)acrylate), dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol five (meth) Dipentaerythritol penta (meth)acrylate, dipentaerythritol hexa (meth)acrylate, bisphenol A di(meth)acrylate , trimethylolpropane tri(meth)acrylate, novolacecoxy(meth)acrylate, dipentaerythritol penta(meth)acrylate having a carboxyl group Dipentaerythritol penta (meth)acrylate derivative, ethylene oxide glycerin trimethylolpropanetri(meth)acrylate, propylene oxide glycerol tris (meth) Propylene oxide glycerin tri(meth)acrylate, epoxy(meth)acrylate oligomer, urethane (meth)acrylate oligomer (uret) Hene (meth) acrylate oligomer, thiol (meth) acrylate oligomer, and polyester (meth) acrylate oligomer At least one compound in the population.

According to still another embodiment of the present invention, there is provided a color filter produced using the above photosensitive resin composition.

Since the photosensitive resin composition for a color filter of the present invention includes a dye having a specific spectral characteristic and a pigment, the color filter made using the photosensitive resin composition described above has excellent light transmittance, Brightness, contrast and color purity with good heat resistance.

1a to 1b and 2a to 2b are graphs showing spectral characteristics of pigments and dyes which can be added to the composition according to the embodiment of the present invention.

3 and 4 are comparative spectral characteristic diagrams of color filters made using the compositions of the examples and comparative examples.

5a to 5b show enlarged photographs of the appearance of a color filter made using the composition of the embodiment of the present invention.

Hereinafter, a photosensitive resin composition according to an embodiment of the present invention and a color filter made using the photosensitive resin composition will be described.

Unless otherwise stated, the nouns used in this specification are as defined below.

First, "(meth)acrylic acid" generally means acrylic acid and/or methacrylic acid.

Further, "(meth) acrylate" generally means acrylate and/or methacrylate.

Further, "alkyl" is defined as including an alkyl group having 1 to 20 carbon atoms; "cycloalkyl" is defined as a cycloalkyl group having a carbon number of 3 to 20; and "aryl" is defined as having a carbon number of 6 to 20 An aryl group; "heteroalkyl" is defined as a heteroalkyl group having a carbon number of 1 to 20; "heterocycloalkyl" is defined as a heterocycloalkyl group having 3 to 20 carbon atoms; "heteroaryl" is defined It is a heteroaryl group having 3 to 20 carbon atoms. Here, "hetero" means that at least one carbon atom is replaced by one atom selected from the group consisting of oxygen, sulfur, nitrogen, phosphorus, ruthenium, and combinations thereof.

Meanwhile, the inventors have confirmed in the research process of repeatedly performing the photosensitive resin composition for a color filter that the photosensitive resin composition can be exhibited if the dye having a specific spectral characteristic is used together with the pigment. A color filter that exhibits excellent light transmittance, brightness, contrast, and color purity and exhibits good heat resistance.

According to an embodiment of the present invention, there is provided a photosensitive resin composition for a color filter comprising an adhesive resin; a reactive unsaturated compound; a blue pigment; having a wavelength range of 430 to 465 nm a light transmittance equal to or higher than 90%, and a light having a light transmittance equal to or lower than 55% in a wavelength range of 495 to 505 nm; a polymerization initiator; and a solvent.

According to another embodiment of the present invention, there is provided a photosensitive resin composition for a color filter comprising an adhesive resin; a reactive unsaturated compound; a green pigment; having a wavelength range of 530 to 540 nm a light transmittance equal to or higher than 95%, and a dye having a light transmittance equal to or lower than 55% in a wavelength range of 580 to 590 nm; a polymerization initiator; and a solvent.

Hereinafter, a feeling for a color filter according to an embodiment of the present invention will be described. The light resin composition may include various constituent components.

Adhesive resin

The adhesive resin ensures the dispersion stability of the pigment and the dye, and at the same time, forms a pixel of a desired resolution in the development process.

The adhesive resin which can be used is not particularly limited, and it can be selected from an adhesive resin which is commonly used in the resin composition for color filters in the art.

According to an embodiment of the present invention, the adhesive resin may be a copolymer of at least one monomer having an enoic acid group and at least one (meth) acrylate monomer.

The adhesive resin may be 10 to 40% by weight of a monomer having an olefinic group and 60 to 90% by weight of a (meth) acrylate monomer, preferably 20 to 40% by weight. a monomer of an enoyl group and a copolymer of 60 to 80% by weight of a (meth) acrylate monomer, more preferably 25 to 35 wt% of a monomer having an enoyl group and 65 to 75 wt% ( A copolymer of methyl acrylate monomers.

Specifically, if the content of the monomer having an enoic acid group in the adhesive resin is less than 10% by weight, the solubility of the photosensitive resin composition in the alkaline developer may be lowered. Further, if the content of the monomer having an enoic acid group in the adhesive resin is more than 40% by weight, pattern loss and tearing may occur in a developing process using an alkali developer ( Tearing). Moreover, if the content of the (meth) acrylate-based monomer in the adhesive resin is less than 60% by weight, the adhesion to the substrate during the development process may be lowered, causing the tearing of the pattern to become severe. And the straightness of the formed pattern deteriorates. Also, if the content of the (meth) acrylate-based monomer in the adhesive resin is more than 90% by weight, the time required for development may increase, so that the yield is lowered.

The monomer having an enoic acid group may be selected from the group consisting of (meth)acrylic acid, itaconic acid, maleic acid, and fumaric acid ( Fumaric acid), vinyl acetic acid, 2-acryloyloxyethyl hydrogen phthalate, and 2-acryloyloxypropyl hydrogen phthalate At least one compound of the group formed.

Further, the (meth) acrylate-based monomer may be selected from (meth) propyl Isobutyl(meth)acrylate, tert-butyl(meth)acrylate, lauryl(meth)acrylate,ste Methyl aryl acrylate, cyclohexyl (meth) acrylate, isobonyl (meth) acrylate, (methyl) Benzyl methacrylate, 2-hydroxyalkyl (meth)acrylate, trimethoxybutyl (meth)acrylate , ethylcarbitol (meth)acrylate, phenoxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate (4) -hydroxybutyl(meth)acrylate), phenoxyethyleneglycol (meth)acrylate, 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl(meth)acrylate, 2-acryloxyethyl 2-hydroxypropyl (meth)phth Alate), 2-hydroxy-3-phenoxypropyl (meth)acrylate, triethylmethoxyethyl (meth)acrylate ( Triethylsiloxylethyl (meth)acrylate) and at least one compound of the group consisting of ethyltriglycol (meth)acrylate.

Further, the adhesive resin preferably has a weight average molecular weight (Mw) of 5,000 to 50,000 in consideration of adhesion to a substrate, dispersion stability of an additive component, and the like.

The content of the adhesive resin may be 5 to 15% by weight based on the total weight of the photosensitive resin composition. Specifically, the content of the adhesive resin is preferably equal to or higher than 5 wt% by the addition of the adhesive resin to exhibit the lowest dispersion stability, film strength, heat resistance and the like. Further, if the adhesive resin is used in an excessive amount, the viscosity of the photosensitive resin composition is excessively increased to lower the optical properties, physical properties, and process efficiency of the photosensitive resin composition. In order to improve this problem, the content of the adhesive resin is preferably equal to or lower than 15% by weight.

Reactive unsaturated compound

The photosensitive resin composition for a color filter according to the present invention comprises a reactive unsaturated compound. The reactive unsaturated compound is used in combination with the adhesive resin to impart viscosity to the photosensitive resin composition and to secure film strength.

Specifically, the reactive unsaturated compound may be selected from the group consisting of a thermal polymerization or photopolymerization monomer, a thermal polymerization reaction or a photopolymerization oligomer, and a mixture thereof.

The thermal polymerization or photopolymerization monomer may be selected from the group consisting of ethyleneglycol di(meth)acrylate and diethyleneglycol di(meth). Acrylate), triethyleneglycol di(meth)acrylate, propyleneglycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate (1,6-hexanediol di(meth)acrylate) Neopentylglycol di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol IV Pentaerythritol tetra(meth)acrylate, pentaerythritol penta(meth)acrylate, pentaerythritol hexa(meth)acrylate, two Dipentaerythritol di(meth)acrylate, Dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth) )acrylate), dipentaerythritol hexa(meth)acrylate, bisphenol A di(meth)acrylate, trimethylolpropane tris Trimethylolpropane tri(meth)acrylate, novolac epoxy (meth)acrylate, dipentaerythritol penta(meth)acrylate with carboxyl group a derivative, ethylene oxide glycerin trimethylopropane tri(meth)acrylate, and propylene oxide glycerol tris(methyl)propyl At least one compound of the group consisting of propylene oxide glycerin tri(meth)acrylate.

Further, the thermal polymerization or photopolymerization oligomer may be selected from the group consisting of epoxy (meth) acrylate oligomers and urethane (meth) acrylate oligomers. Urethane (meth) acrylate oligomer, thiol (meth) acrylate oligomer, and polyester (meth) acrylate oligomer At least one oligomer in the population.

The reactive unsaturated compound may be included in an amount of from 100 to 250 parts by weight, preferably from 150 to 250 parts by weight, more preferably from 100 to 200 parts by weight, based on 100 parts by weight of the adhesive resin. Specifically, in order to improve the problem of difficulty in realizing the pattern due to the low curing degree of the photosensitive resin, the content of the reactive unsaturated compound is preferably based on 100 parts by weight of the adhesive resin. It may be equal to or higher than 100 parts by weight. Further, if the amount of the reactive unsaturated compound added is too large, the degree of curing of the photosensitive resin composition is excessively increased, so that the tearing of the pattern at the time of development becomes severe, and the flatness of the pattern is lowered. In order to improve this problem, the content of the reactive unsaturated compound may preferably be equal to or lower than 250 parts by weight based on 100 parts by weight of the adhesive resin.

pigment

The photosensitive resin composition according to the present invention includes a pigment.

The pigment may be selected from blue or green pigments which are often used in the color resin composition for color filters in the technical field of the present invention.

The blue pigment may be a blue pigment based on copper phthalocyanine, and the preferred compound is classified by a color index of the pigment, and includes a color index pigment blue (Color Index (CI) Pigment Blue). 15, 15:3, 15:4, 15:6, 60 and other blue pigments.

The green pigment may be a green pigment based on halogenated phthalocyanine, and the preferred compound is classified by a color index of the pigment, and includes a color index pigment green (Color Index (CI) Pigment Green) 7, 36, 58 and other green pigments.

The pigment may be directly added to the photosensitive resin composition of the present invention as the pigment itself, or may be added to the photosensitive resin composition of the present invention in the form of a pigment dispersion liquid containing a dispersing agent or a solvent.

As the dispersing agent which may be included in the pigment dispersion liquid, a nonionic dispersing agent, an ionic dispersing agent, or a cationic dispersing agent may be selectively used, and specific examples thereof may include a polyalkyleneglycol and an ester thereof. Polyoxyalkylene; a multivalent alcohol ester alkylene oxide adduct; an alcohol alkylene oxide adduct; an alkylamine and a combination thereof . Further, the dispersant may be contained in an amount of 10 to 20 parts by weight based on 100 parts by weight of the pigment.

As a solvent which can be included in the pigment dispersion, ethyleneglycol acetate, ethyl cellosolve, propyleneglycol methylether acetate, ethyl lactate can be used. Ethyl lactate), polyethyleneglycol, cyclohexanone, propyleneglycol methylether, and the like. The content of the solvent is preferably controlled so that the pigment dispersion has a solid content of 5 to 30% by weight.

Meanwhile, the particle diameter of the pigment is determined in consideration of dispersion stability and pixel resolution, and the number average particle diameter of the pigment may be 30 to 200 nm.

The pigment may be included in an amount of from 50 to 150 parts by weight, preferably from 75 to 150 parts by weight, more preferably from 75 to 125 parts by weight, based on 100 parts by weight of the adhesive resin. Specifically, the color gamut, pattern formability, adhesion, curing property, and the like of the pigment are considered, and the content of the pigment is preferably within the above range.

dye

The photosensitive resin composition according to the present invention includes a dye.

In other words, the photosensitive resin composition of the present invention includes a dye (auxiliary dye) and the above-mentioned pigment (main pigment). According to the present invention, the dye has unique spectral characteristics in a specific wavelength range, and is controlled by the photosensitive resin composition by synergy with a pigment exhibiting a specific color. The light transmittance of the color filter and the light transmission width are used to improve color purity, brightness, contrast, and the like.

According to an embodiment of the present invention, if the pigment is a blue pigment, the dye represented by the chemical formula 1 may have a light transmittance equal to or higher than 90% in a wavelength range of 430 to 465 nm, preferably 90. a light transmittance of 99%, more preferably 93 to 99%, and a light transmittance of 55% or less in the wavelength range of 495 to 505 nm, preferably 45 to 55%. The compound is preferably a compound having a spectral characteristic of a light transmittance of 45 to 50%.

According to another embodiment of the present invention, if the pigment is a green pigment, the dye represented by the chemical formula 1 may have a light transmittance equal to or higher than 95% in a wavelength range of 530 to 540 nm, preferably 95. a light transmittance of up to 99%, and a light transmittance equal to or lower than 55% in a wavelength range of 580 to 590 nm, preferably a light transmittance of 45 to 55%, more preferably 45 to 50%. The compound of the spectral properties of the rate.

The dye having the above spectral characteristics may be a compound represented by the following Chemical Formula 1:

In the chemical formula 1, M is copper, cobalt, aluminum, zinc, nickel, platinum or chromium; N is nitrogen; and R ¹ to R ¹⁶ are each independently a hydrogen atom, a halogen atom, a carboxyl group, a hydroxyl group, a sulfonic acid group, a heterocyclic group-substituted sulfonic acid alkyl group, a sulfonic acid hydroxyl group, a sulfonic acid alkoxy group, a sulfonic acid aryl group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a carbon number of 6 to 20 An aryl group, a heteroalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

The dye having the above spectral characteristics may preferably be a compound represented by the following Chemical Formula 2:

In the chemical formula 2, M is copper, cobalt, aluminum, zinc, nickel, platinum or chromium; N is nitrogen; O is oxygen; and R ^a to R ^h are each independently an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group of 3 to 20, an aryl group having 6 to 20 carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

The compound represented by the chemical formula 1 or the chemical formula 2 exhibits blue or green depending on the structure of R ¹ to R ¹⁶ or R ^a to R ^h and the length of the substituent.

According to an embodiment of the present invention, the blue dye conforming to the above spectral characteristics may be, but not limited to, selected from the group consisting of Octa(2-ethylhexyloxy)Cu Phthalocyanine, and eight. (2-ethylhexyloxy)Co Phthalocyanine, Octa(2-ethylhexyloxy)Al Phthalocyanine, eight (2) -ethylhexyloxy)zinc phthalocyanine (Octa(2-ethylhexyloxy)Zn Phthalocyanine), octa(2-ethylhexyloxy)Ni Phthalocyanine, eight (2-B) At least one of the group consisting of Octa(2-ethylhexyloxy)Pt Phthalocyanine and Octa(2-ethylhexyloxy)Cr Phthalocyanine Compound.

Further, according to an embodiment of the present invention, the green dye satisfying the above spectral characteristics may be, but not limited to, selected from octa (1,4,7,10-tetraoxaundecyl) copper phthalocyanine (Octa ( 1,4,7,10-tetraoxaundecyl)Cu Phthalocyanine), octa (1,4,7,10-tetraoxadecyl)cobalt phthalocyanine (Octa(1,4,7,10-tetraoxaundecyl)Co Phthalocyanine ), octa (1,4,7,10-tetraoxaundecyl)aluminum phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl) Al Phthalocyanine), eight (1,4,7,10- Tetradodecyl) zinc phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl)Zn Phthalocyanine), octa (1,4,7,10-tetraoxadecyl) nickel phthalocyanine ( Octa(1,4,7,10-tetraoxaundecyl)Ni Phthalocyanine), octa (1,4,7,10-tetraoxaundecyl)platinium phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl) At least one compound of the group consisting of Pt Phthalocyanine) and octa (1,4,7,10-tetraoxaundecyl) Cr Phthalocyanine .

The dye may be included in an amount of from 50 to 250 parts by weight, preferably from 100 to 250 parts by weight, more preferably from 100 to 200 parts by weight, based on 100 parts by weight of the adhesive resin. Specifically, in order to exhibit the lowest influence depending on the spectral characteristics of the dye added, the content of the dye is preferably equal to or more than 50 parts by weight based on 100 parts by weight of the adhesive resin. Further, if the dye is used in an excessive amount, the dye may precipitate or the heat resistance may be lowered after baking. To improve the problem, the dye content is preferably 200 parts by weight based on 100 parts by weight of the adhesive resin. Share.

Polymerization initiator

The photosensitive resin composition according to the present invention includes a polymerization initiator. The polymerization initiator can be activated by heat or light or the like to initiate polymerization of the above-mentioned reactive unsaturated compound, and the polymerization initiator can be used by a user who is a person skilled in the art.

According to an embodiment of the present invention, the polymerization initiator may be selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, and a thioxanthone compound (thioxanthone- Based on a compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, and a mixture of the foregoing.

Specifically, the polymerization initiator may be 2,2'-diethoxyacetophenone (2,2'-diethoxyacetophenone), 2,2'-dibutoxyacetophenone (2, 2) '-dibutoxyacetophenone), (2-hydroxy-2-methylethyl)phenylketone, p-butyltrichloroacetophenone, P-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone (2,2' -dichloro-4-phenoxyacetophenone), 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinyl-1-propanone (2-methyl-1-(4-(methylthio)phenyl) An acetophenone-based compound such as -2-morpholinopropan-1-one); including benzophenone, benzoylbenzoic acid, benzoyl methylbenzoic acid, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino) 4,4'-bis(dimethyl amino)benzophenone, 4,4'- Bis(diethylamino)benzophenone, 4,4'-dichlorobenzophenone, 3,3' a benzophenone-based compound such as 3,3'-dimethyl-2-methoxybenzophenone; Thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thiophene Thiophenone ketone compounds such as 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2-chloro thioxanthone Including benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzophenone a benzoin ketone-based compound such as benzoin isobutyl ether or benzyl dimethylketal; including 2,4,6-trichloro-s-triazine (2,4,6- Trichloro-s-triazine), 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2- (3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine (2-(3',4'-dimethoxy styryl)-4,6- Bis(trichloro methyl)-s-triazine), 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine (2-(4'-methoxy naphthy) l)-4,6-bis(trichloromethyl)-s-triazine), 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine (2-(p -methoxy phenyl)-4,6-bis(trichloromethyl)-s-triazine), 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine (2-(p -tolyl)-4,6-bis(trichloromethyl)-s-triazine), 2-diphenyl-4,6-bis(trichloromethyl)-s-triazine (2-dipenyl-4,6-bis (trichloro methyl)-s-triazine), bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphthol- 1-yl)-4,6-bis(trichloromethyl)-s-triazine (2-(naphtho 1-yl)-4,6-bis(trichloro methyl)-s-triazine), 2-(4) -Methoxynaphthol-1-yl)-4,6-bis(trichloromethyl)-s-triazine (2-(4-methoxy naphtho 1-yl)-4,6-bis(trichloromethyl)- S-triazine), 2,4-trichloromethyl(piperonyl)-6-triazine, 2,4-trichloromethyl (4'- a triazinyl compound such as 2,4-trichloro methyl (4'-methoxy styryl-6-triazine); including 1,2-octanedione-1-( 4-phenylthio)phenyl-2-(o-benzylidene fluorene) (1,2-octanedione-1-(4-phenylthio)phenol-2-(o-be Nzoyloxime) and ethyl ketone-1-(9-ethyl)-6-(2-methylbenzimid-3-yl)-1-(o-ethylindenyl) a mercapto compound such as (ethanone-1-(9-ethyl)-6-(2-methylbenzoyl-3-yl)-1-(o-acetyloxime)); or a mixture of the foregoing compounds.

Further, as the polymerization initiator, a carbazole-based compound, a diketone compound, a sulfonium borate-based compound, a diazo compound ( A compound such as a diazo-based compound or a biimidazole-based compound.

The problem of a decrease in the light transmittance due to the unreacted starting agent after the polymerization reaction is considered, and the content of the polymerization initiator is determined by being able to sufficiently initiate the polymerization reaction. According to the present invention, the polymerization initiator may be contained in an amount of 5 to 50 parts by weight, preferably 10 to 50 parts by weight, more preferably 10 to 40 parts by weight based on 100 parts by weight of the binder resin.

Solvent

The photosensitive resin composition for a color filter according to the present invention includes a solvent.

The solvent is added to control the solubility and viscosity of the components and the like contained in the composition, and the solvent is not specified, and a solvent which is commonly used in the art can be used as long as the solvent does not occur with the above components. It reacts and is compatible with the above ingredients.

According to an embodiment of the present invention, the solvent may be, for example, methanol, ethanol, isopropylalcohol, butylalcohol, benzylalcohol, diacetoneal cohol, or the like. Alcohols; ethers such as dichloroethylether, n-butylether, diisoamylether, methylphenylether, tetrahydrofurane, etc.; Glycol ethers such as ethyleneglycol monomethylether, ethylene glycol monoethylether; such as methyl cellosolve acetate, ethyl cellosolve a cellosolve acetate such as ethyl cellosolve acetate or diethyl cellosolve acetate; such as methylethyl carbitol; Diethyl carbitol (diethyl Carbitol), diethylene glycol monomethylether, diethylene glycol monoethylether, diethylene glycol dimethylether, diethylene glycol Carbitol such as methylethylether), diethylene glycol diethylether, etc.; such as propyleneglycol methylethyl acetate, propyleneglycol methylether acetate, propylene glycol Alkyl ether acetates such as propyleneglycol propylether acetate; aromatic hydrocarbons such as toluene, xylene, etc.; such as methyl ethyl ketone ( Methylethylketone), cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, (4-hydroxy-4-methyl-2-pentanone), methyl-n-propyl ketone (methyl-n- Ketones such as propylketone), methyl-n-butylketone, methyl-n-amylketone, 2-heptanone, etc. ; such as ethyl acetate (acet Acic acid ethyl), saturated fatty monocarboxylic acid alkyl esters such as acetic acid-n-butyl or acetic acid isobutyl; such as lactic acid A lactic acid ester such as lactic acid methyl or lactic acid ethyl; such as oxy acetic acid methyl or oxy acetic acid ethyl , oxy acetic acid alkyl esters such as oxy acetic acid butyl; such as methoxy acetic acid methyl, methoxy acetic acid ethyl ), alkoxy acetic acid alkyl (meth), ethoxy acetic acid methyl, ethoxy acetic acid ethyl, etc. Ester); 3-oxopropionic acid alkyl such as 3-oxy propionic acid methyl or 3-oxy propionic acid ethyl (3-oxy Propionic acid alkyl ester); such as 3-methoxypropionic acid methyl ester (3-methoxy Propionic acid methyl), 3-methoxy propionic acid ethyl, 3-ethoxy propionic acid ethyl, 3-ethoxypropionic acid methyl ester (3- Ethyl propionic acid methyl), such as 3-alkoxy propionic acid alkyl ester; such as 2-oxypropionate methyl ester (2-oxyl Propionic acid methyl), 2-oxy propionic acid ethyl, 2-oxy propionic acid propyl, etc. 2-oxypropionic acid alkyl ester (2-oxypropionic acid propyl) Propionic acid alkyl ester); such as 2-methoxy propionic acid methyl, 2-methoxy propionic acid ethyl, ethyl 2-ethoxypropionate (2-ethoxykionic propionic acid ethyl), 2-alkoxy propionic acid alkyl ester or the like; 2-alkoxy propionic acid alkyl ester; 2-oxy-2-methyl propionic acid methyl, 2-oxy-2-methyl propionic acid ethyl, etc. 2 -2-oxy-2-methyl propionic acid ester; such as 2-methoxy-2-methyl propionic acid methyl 2-oxo-2-methylpropionic acid ethyl or the like 2-alkoxy-2-methylpropionic acid alkyl monooxymonocarboxylic acid alkyl Monooxy monocarboxylic acid alkyl ester of 2-alkoxy-2-methyl propionic acid alkyl; 2-hydroxy propionic acid ethyl, 2-hydroxy-2-methyl propionic acid ethyl, hydroxyl acetate acetic acid, An ester of 2-hydroxy-3-methyl butyric acid methyl or the like; a keonic acid ester such as pyruvic acid ethyl (ketonic acid) Ester); or a mixture of the foregoing compounds.

Further, the solvent may include N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide ), benzylethylether, dihexylether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol 1-octanol), 1-nonanol, benzylalcohol, acetic acid benzyl, benzoic acid ethyl, oxalic acid diethyl ), maleic acid diethyl, gamma-butyrolactone, ethyl carbonate Carbonate, phenyl cellosolve acetate, ethyleneglycol acetate, ethyl cellosolve, ethyl lactate ), polyethylene glycol (polyethyleneglycol) and the like.

In view of compatibility and reactivity, as the solvent, a glycol ether such as ethylene glycol monoethyl ether or the like; a cellosolve such as (ethyl cellosolve acetate) or the like is preferably used. Acetate); esters such as 2-hydroxy propionic acid ethyl; carbitols such as diethyleneglycol monomethyl ether; Such as propylene glycol alkyl ether acetate, propylene glycol propyl ether acetate, propylene glycol alkyl ether acetate; ethylene glycol acetate (ethyleneglycol acetate), Ethyl cellosolve, ethyl lactate, polyethyleneglycol or a mixture of the foregoing.

The content of the solvent is determined in consideration of the viscosity, coatability, and volatility of the solvent of the photosensitive resin composition. According to the present invention, the solvent may be contained in an amount of from 100 to 500 parts by weight, preferably from 150 to 450 parts by weight, most preferably from 200 to 400 parts by weight based on 100 parts by weight of the adhesive resin.

Other additives

The photosensitive resin composition according to the present invention may further include other additives commonly used in the art.

These additives can improve the storage stability, coatability, adhesion, and the like of the photosensitive resin composition. According to the present invention, the additive may be an epoxy compound, malonic acid, 3-amino-1,2-propandiol, or a decyl group ( Silane based) couplant, sulfhydryl or fluorine leveling agent, surfactant, and the like. Further, the content of the additive is determined depending on the controllability, and is not particularly limited as long as it does not adversely affect the photosensitive resin composition.

Meanwhile, according to another object of the present invention, a color filter made using the above photosensitive resin composition is provided.

The color filter is used in addition to the photosensitive resin composition of the present invention. In addition, it can be manufactured in a manner commonly used in the art.

According to an embodiment of the present invention, the color filter may be coated with a photosensitive resin composition by spin coating or slit coating to a substrate of 1 to 5 μm, and irradiated to form a color filter. The pattern is then fabricated by developer treatment and, if desired, a baking process to form the desired pattern.

Hereinafter, the present invention will be better understood by the preferred embodiments. However, the following examples are only intended to illustrate the invention, and the scope of the invention is not limited thereto.

[Preparation example]

Preparation example 1

(Preparation of adhesive)

100 parts by weight of the mixture contains 33 wt% methacrylic acid, 40 wt% benzylmethacrylate, 11 wt% ethyltriglycol methacrylate, and 16 wt%. 2-hydroxyethylmethacrylate, 4 parts by weight of a polymerization initiator (azobisisobutyronitrile, azobisisobutyronitrile) and 55 parts by weight of a solvent (propylene glycol monoethylether) Polymerization was carried out to prepare a polymer resin having a weight average molecular weight of 30,000.

Preparation Example 2-1

(Synthesis of blue dye: octa(2-ethylhexyloxy) copper phthalocyanine)

About 12.8 grams of 1,2-di(2-ethylhexyloxy)-4,5-dibromobenzene and about 7.0 grams of cyanide Copper (Copper cyanide) was added to the solvent of Dimethylformamide (about 130 mL), and the mixture was stirred at room temperature for 5 hours under a nitrogen atmosphere. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-di(2-ethylhexyloxy)-4,5-dibromobenzene (1,2-Di(2-ethylhexyloxy)-4,5-dibromobenzene. ).

Next, 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene (about 2 g), ammonia (about 2 g), and sodium (about 0.34 g) were added to the solvent methanol (about In 34 mL), the above mixture was stirred at room temperature for about 5 hours to obtain 1,3-diimido-5,6-di(2-ethylhexyloxy)isoindole (1,3-Diimino- 5,6-di(2-ethylhexyloxy)isoindole).

Mixed 1,3-diimido-5,6-di(2-ethylhexyloxy)isoindole (about 1.19 g) and copper (about 0.2 g) were reacted at a temperature of about 270 ° C for about 96 hours to obtain octa(2-ethylhexyloxy) copper phthalocyanine.

Preparation Example 2-2

(Synthesis of blue dye: octa(2-ethylhexyloxy)cobalt phthalocyanine)

About 12.8 g of 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene and about 7.0 g of copper cyanide were added to the solvent Dimethylformamide ( In about 130 mL), the above mixture was stirred at room temperature for 5 hours under a nitrogen atmosphere. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-di(2-ethylhexyloxy)-4,5-dibromobenzene (1,2-Di(2-ethylhexyloxy)-4,5-dibromobenzene. ).

Next, 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene (about 2 g), ammonia (about 2 g), and sodium (about 0.34 g) were added to the solvent methanol (about In 34 mL), the foregoing mixture was stirred at room temperature for about 5 hours to obtain 1,3-diimino-5,6-di(2-ethylhexyloxy)isoindole.

Mixing 1,3-diimido-5,6-bis(2-ethylhexyloxy)isoindole (about 2 g) and hydroquinone (about 0.215 g), reacting at a temperature of about 210 ° C About 48 hours was obtained to obtain Octa(2-ethylhexyloxy) Dihydrogen Phthalocyanine.

Thereafter, octa(2-ethylhexyloxy)dihydrophthalocyanine (about 1.0 g) and cobalt dichloride (about 0.363 g) were mixed and reacted at room temperature for about 24 hours to obtain octa(2-ethyl group). Hexyloxy)cobalt phthalocyanine.

Preparation Example 2-3

(Synthesis of blue dye: octa(2-ethylhexyloxy)platinium phthalocyanine)

About 12.8 g of 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene and about 7.0 g of copper cyanide were added to the solvent Dimethylformamide ( In about 130 mL), the above mixture was stirred at room temperature for 5 hours under a nitrogen atmosphere. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-di(2-ethylhexyloxy)-4,5-dibromobenzene (1,2-Di(2-ethylhexyloxy)-4,5-dibromobenzene. ).

Next, 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene (about 2 g), ammonia (about 2 g), and sodium (about 0.34 g) were added to the solvent methanol (about In 34 mL), the above mixture was stirred at room temperature for 5 hours to obtain 1,3-diimino-5,6-di (2-B) Hexyloxy)isoindole.

Mixing 1,3-diimido-5,6-bis(2-ethylhexyloxy)isoindole (about 1.5 g) and platinum dichloride (about 0.311 g), reacting at a temperature of about 270 ° C About 48 hours was obtained to obtain octa(2-ethylhexyloxy)platinium phthalocyanine.

Preparation Example 2-4

(Synthesis of blue dye: octa(2-ethylhexyloxy) dihydrophthalocyanine)

About 12.8 g of 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene and about 7.0 g of copper cyanide were added to the solvent Dimethylformamide ( In about 130 mL), the above mixture was stirred at room temperature for about 5 hours under a nitrogen atmosphere. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-di(2-ethylhexyloxy)-4,5-dibromobenzene (1,2-Di(2-ethylhexyloxy)-4,5-dibromobenzene. ).

Next, 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene (about 2 g), ammonia (about 2 g), and sodium (about 0.34 g) were added to the solvent methanol (about In 34 mL), the foregoing mixture was stirred at room temperature for about 5 hours to obtain 1,3-diimino-5,6-di(2-ethylhexyloxy)isoindole.

Mixing 1,3-diimido-5,6-bis(2-ethylhexyloxy)isoindole (about 2 g) and hydroquinone (about 0.215 g), the mixture at a temperature of about 210 ° C The reaction was carried out for about 48 hours to obtain octa(2-ethylhexyloxy)dihydrogen Phthalocyanine.

Preparation example 3-1

(Synthesis of green dye: octa (1,4,7,10-tetraoxaundecyl) copper phthalocyanine)

About 12.6 grams of 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene and about 6.05 grams of copper cyanide were added to the solvent Dimethylformamide (Dimethylformamide) In about 114 mL), the foregoing mixture was stirred at 130 ° C for about 15 hours under a nitrogen atmosphere. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-bis(1,4,7,10-tetraoxadecyl)-4,5-dicyanobenzene (1,2-Di(1). , 4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene).

Next, 1,2-bis(1,4,7,10-tetraoxaundecyl)-4,5- Dicyanobenzene (about 3.55 g), ammonia (about 2.0 g), and sodium (about 0.39 g) were added to the solvent methanol (about 39 mL), and the mixture was stirred at room temperature for about 5 hours to obtain 1,3-. Diimido-5,6-bis(1,4,7,10-tetraoxaundecyl)isoindole (1,3-Diimino-5,6-di(1,4,7,10) -tetraoxaundecyl)isoindole).

Mixing 1,3-diimido-5,6-bis(1,4,7,10-tetraoxaundecyl)isoindole (about 1 gram) and copper (about 0.140 gram), the aforementioned mixture The reaction was carried out at a temperature of about 220 ° C for about 18 hours to obtain octa (1,4,7,10-tetraoxaundecyl) copper Phthalocyanine.

Preparation Example 3-2

(Synthesis of green dye: octa(1,4,7,10-tetraoxaundecyl)cobalt phthalocyanine)

About 12.6 grams of 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene and about 6.05 grams of copper cyanide were added to the solvent Dimethylformamide (Dimethylformamide) In about 114 mL), the aforementioned mixture was stirred at 130 ° C for about 15 hours. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-bis(1,4,7,10-tetraoxadecyl)-4,5-dicyanobenzene (1,2-Di(1). , 4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene).

Next, 1,2-bis(1,4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene (about 3.55 g), ammonia (about 2.0 g), and sodium (about 0.39 g) was added to the solvent methanol (about 39 mL), and the mixture was stirred at room temperature for about 5 hours to obtain 1,3-diimido-5,6-di (1,4,7,10-tetra Isophthalic acid isoindole (1,3-Diimino-5,6-di(1,4,7,10-tetraoxaundecyl)isoindole).

Mixing 1,3-diimido-5,6-bis(1,4,7,10-tetraoxaundecyl)isoindole (about 1.60 g) and cobalt (about 0.419 g), the foregoing mixture The reaction was carried out at a temperature of about 280 ° C for about 17 hours to obtain octa (1,4,7,10-tetraoxaundecyl)Co Phthalocyanine.

Preparation Example 3-3

(Synthesis of green dye: octa (1,4,7,10-tetraoxadecyl) platinum phthalocyanine)

About 12.6 grams of 1,2-bis(2-ethylhexyloxy)-4,5-dibromobenzene About 6.05 grams of copper cyanide was added to the solvent Dimethylformamide (about 114 mL), and the mixture was stirred at 130 ° C for about 15 hours. Thereafter, the pressure is lowered to remove the solvent to obtain 1,2-bis(1,4,7,10-tetraoxadecyl)-4,5-dicyanobenzene (1,2-Di(1). , 4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene).

Next, 1,2-bis(1,4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene (about 3.55 g), ammonia (about 2.0 g), and sodium (about 0.39 g) was added to the solvent methanol (about 39 mL), and the mixture was stirred at room temperature for about 5 hours to obtain 1,3-diimido-5,6-di (1,4,7,10-tetra Isophthalic acid isoindole (1,3-Diimino-5,6-di(1,4,7,10-tetraoxaundecyl)isoindole).

1,3-Diimido-5,6-bis(1,4,7,10-tetraoxaundecyl)isoindole (about 1.5 g) and platinum dichloride (about 0.250 g) Addition to dimethylformamide (about 3.0 mL), the above mixture is allowed to react at room temperature for about 24 hours to obtain octa(1,4,7,10-tetraoxaundecyl)platinium phthalocyanine (Octa) (1,4,7,10-tetraoxaundecyl)Pt Phthalocyanine).

[examples and comparative examples]

Example 1

Based on 100 parts by weight of the adhesive resin of Preparation Example 1; about 175 parts by weight of a reactive unsaturated compound (about 50 parts by weight of bisphenol epoxy acrylate oligomer and about 125) were mixed. Dipentaerythritol hexaacrylate; about 625 parts by weight of blue dye dispersion (product name: DJBLUE-01, manufacturer: MIKYNI, solvent: propylene glycol methyl ether acetate, containing 15 wt% pigment a dispersion of about 93.75 parts by weight when converted to a pigment content; about 28.75 parts by weight of a polymerization initiator (about 6.25 parts by weight of product name OX-01, manufacturer: BASF, about 15 parts by weight of the product) The name Irgacure-369, manufacturer: BASF, and about 7.5 parts by weight of 4,4'-bisdiethylaminobenzophenone); about 316.25 parts by weight of solvent propylene glycol A Ether acetate; and about 0.05 parts by weight of a fluorine-containing leveling agent (product name: F-474, manufacturer: DIC), and the foregoing mixture was stirred at room temperature for about 2 hours, after which the impurities were removed using a 1.2 μm filter device.

About 125 parts by weight of the dye of Preparation Example 2-1 was mixed with the above mixture based on 100 parts by weight of the adhesive resin, and the resulting mixture was stirred at room temperature for about 2 hours to prepare a photosensitive resin composition.

Example 2

The photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 1, except that the dye of Preparation Example 2-1 was replaced with the dye of Preparation Example 2-2 in the same addition amount.

Example 3

A photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 1, except that the dye of Preparation Example 2-1 was replaced with the dye of Preparation Example 2-3, and Example 2 was prepared based on 100 parts by weight of the adhesive resin. The amount of dye added to -3 is about 100 parts by weight.

Comparative example 1

The photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 1, except that the dye of Preparation Example 2-1 was not added.

Comparative example 2

The photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 1, except that the dye of Preparation Example 2-1 was replaced with the dye of Preparation Example 2-4 in the same addition amount.

Example 4

Based on 100 parts by weight of the adhesive resin of Preparation Example 1; Mixing about 175 parts by weight of a reactive unsaturated compound (about 50 parts by weight of a bisphenol epoxy acrylate oligomer and about 125 parts by weight of dipentaerythritol hexaacrylate); 750 parts by weight of green dye dispersion (product name: DJGREEN-01, manufacturer: Special Pigment, solvent: propylene glycol methyl ether acetate, dispersion containing 15 wt% pigment, about 112.5 parts by weight when converted to pigment content ); about 28.75 parts by weight of a polymerization initiator (about 6.25 parts by weight of product name OX-01, manufacturer: BASF, about 15 parts by weight of product name Irgacure-369, made) Manufacturer: BASF, and about 7.5 parts by weight of 4,4'-bisdiethylaminobenzophenone); about 316.25 parts by weight of solvent propylene glycol methyl ether acetate; About 0.05 part by weight of a fluorine-containing leveling agent (product name: F-474, manufacturer: DIC), and the foregoing mixture was stirred at room temperature for about 2 hours, after which the impurities were removed using a 1.2 μm filter device.

About 187.5 parts by weight of the dye of Preparation Example 3-1 was mixed with the above mixture based on 100 parts by weight of the adhesive resin, and the resulting mixture was stirred at room temperature for about 2 hours to prepare a photosensitive resin composition.

Example 5

The photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 4 except that the dye of Preparation Example 3-1 was replaced with the dye of Preparation Example 3-2 in the same addition amount.

Example 6

The photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 4 except that the dye of Preparation Example 3-1 was replaced with the dye of Preparation Example 3-3, and Example 3 was prepared based on 100 parts by weight of the adhesive resin. The amount of dye added to -3 was about 162.5 parts by weight.

Comparative example 3

The photosensitive resin composition was prepared in the same manner and under the same conditions as in Example 4, except that the dye of Preparation Example 3-1 was not added.

[Experimental example]

Experimental example 1

(Measure the transmittance of pigments and dyes according to the wavelength range)

The spectral characteristics of the blue dyes used in Examples 1 to 3 (Fig. 1a) and the spectral characteristics of the dyes of Preparation Example 2-1 were measured using a colorimetric measuring device (manufacturer: Otsuka, model: MCPD-3000) (Fig. 1b) The spectral characteristics of the green dyes used in Examples 4 to 6, and the results are shown in Fig. 1 and Fig. 2.

As shown in FIG. 1b, it can be confirmed that the dye of Preparation Example 2-1 has a light transmittance equal to or higher than 90% in the wavelength range of 430 to 465 nm, and is in the wavelength range of 495 to 505 nm. It has a light transmittance equal to or lower than 55%.

Further, as shown in FIG. 2b, it can be confirmed that the dye of Preparation Example 3-1 has a light transmittance equal to or higher than 95% in the wavelength range of 530 to 540 nm, and has a wavelength equal to or lower than the wavelength range of 580 to 590 nm. 55% light transmittance.

Experimental example 2

The photosensitive resin compositions of the examples and comparative examples were respectively applied by a spin coating method to a glass substrate (10 X 10 cm) having a thickness of 2 μm, and prebaked on a hot plate at 90 ° C for 2 minutes, and thereafter, at room temperature. Cool for 1 minute. Light exposure was performed using an exposure apparatus at an exposure amount of 100 mJ/cm 2 (365 nm), followed by post-baking in a 220 ° C ventilated oven for 30 minutes.

Each of the samples produced by the above method was measured for spectral characteristics, light transmittance, brightness, contrast, and heat resistance in the following manner, and the results are shown in Tables 1 to 2 and Figs. 3 to 5.

(Measures the transmittance according to the wavelength range and the appearance of the color filter)

The light transmittance in the wavelength range of the color filter samples prepared using the photosensitive resin compositions of Example 2 and Comparative Example 1 was measured using a colorimetric measuring device (manufacturer: Otsuka, model: MCPD-3000), and measured. A color filter sample prepared using the photosensitive resin composition of Example 5 and Comparative Example 3 was used, and the results are shown in Fig. 3 and Fig. 4, respectively.

Further, the appearance of the color filter prepared using Example 2 and Example 5 was enlarged and observed, and the results are shown in Figs. 5a to 5b.

As shown in FIG. 3 and FIG. 4, it can be confirmed that since the sample is manufactured by using an example including a dye having a unique spectral characteristic in a specific wavelength range, the light transmittance and the light transmission width of the color filter are affected by the pigment. Synergistically controlled to increase color purity.

(light transmittance measurement)

The transmittance (%) of the post-baked substrate was measured using an MCPD-3000 apparatus (manufacturer: Otsuka), wherein the maximum light transmittance (Max%) of the blue pigment was measured in the wavelength range of 450 to 460 nm. The green pigment is in the range of 515 to 550 nm.

(measurement of brightness)

The brightness (Y) of the post-baked substrate was measured using an MCPD-3000 device (manufacturer: Otsuka), in which the brightness was compared based on a specific color coordinate, and the blue pigment was measured at x of 0.14 and y of 0.06, green. The pigment was measured at x of 0.25 and y of 0.63.

(contrast measurement)

The contrast according to polarization was measured using a CT-1 device (manufacturer: TSUBOSAKA), where the contrast was measured with a reference value of 30,000:1 for the bare state.

(heat resistance measurement)

The post-baked substrate was heated in an oven at 240 ° C for 30 minutes, after which the color difference (ΔEab) was measured.

As shown in Table 1 and Table 2, it was confirmed that the blue and green color filters prepared using the photosensitive resin compositions of Comparative Example 1 and Comparative Example 3 had lower light transmittance as compared with the examples. Brightness, and due to the particle scattering properties of the pigment, has a relatively low contrast.

Further, although the blue color filter made using the photosensitive resin composition of Comparative Example 2 has similar light transmittance, brightness, and contrast as compared with the example, it has low heat resistance, and thus is not suitable for use. The process includes a heat-treated liquid crystal display device.

On the contrary, the color filter samples prepared using the photosensitive resin compositions of Examples 1 to 6 have excellent light transmittance, brightness, and contrast, and are actually used. The desired heat resistance is a reference value of 3 or lower.

Claims (10)

A photosensitive resin composition for a color filter comprising: an adhesive resin; a reactive unsaturated compound; a blue pigment; a dye having a wavelength equal to or higher than 90% in a wavelength range of 430 to 465 nm Light transmittance, and light transmittance equal to or lower than 55% in the wavelength range of 495 to 505 nm; a polymerization initiator; and a solvent. A photosensitive resin composition for a color filter comprising: an adhesive resin; a reactive unsaturated compound; a green pigment; a dye having a transmittance equal to or higher than 95% in a wavelength range of 530 to 540 nm The light rate, and a light transmittance of 55% or less in the wavelength range of 580 to 590 nm; a polymerization initiator; and a solvent. The photosensitive resin composition for a color filter according to the first or second aspect of the invention, wherein the dye is a compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the chemical formula 1, M is copper, cobalt, aluminum, zinc, nickel, platinum or chromium; N is nitrogen; and R ¹ to R ¹⁶ are each independently a hydrogen atom, a halogen atom, a carboxyl group, a hydroxyl group, a sulfonic acid group, a heterocyclic group-substituted sulfonic acid alkyl group, a sulfonic acid hydroxyl group, a sulfonic acid alkoxy group, a sulfonic acid aryl group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a carbon number of 6 to 20 An aryl group, a heteroalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. The photosensitive resin composition for a color filter according to the first or second aspect of the invention, wherein the dye is a compound represented by the following Chemical Formula 2: [Chemical Formula 2] In the chemical formula 2, M is copper, cobalt, aluminum, zinc, nickel, platinum or chromium; N is nitrogen; O is oxygen; and R ^a to R ^h are each independently an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group of 3 to 20, an aryl group having 6 to 20 carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. The photosensitive resin composition for a color filter according to claim 1, wherein the dye is selected from the group consisting of octa(2-ethylhexyloxy) copper phthalocyanine (Octa(2-ethylhexyloxy)Cu). Phthalocyanine), Octa(2-ethylhexyloxy)Co Phthalocyanine, Octa(2-ethylhexyloxy)Al Phthalocyanine , Octa(2-ethylhexyloxy)Zn Phthalocyanine, Octa(2-ethylhexyloxy)Ni Phthalocyanine, Eight (2- At least one of the group consisting of Octa(2-ethylhexyloxy)Pt Phthalocyanine and Octa(2-ethylhexyloxy)Cr Phthalocyanine a compound. A photosensitive resin composition for a color filter according to claim 2, wherein the dye is selected from the group consisting of octa(1,4,7,10-tetraoxaundecyl) copper phthalocyanine. (Octa (1,4,7,10-tetraoxaundecyl)Cu Phthalocyanine), octa (1,4,7,10-tetraoxaundecyl)cobalt phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl) )Co Phthalocyanine), octa (1,4,7,10-tetraoxaundecyl)aluminum phthalocyanine (Octa(1,4,7,10-tetraoxaundecyl)Al Phthalocyanine), eight (1,4,7) , 10-tetraoxadecyl) zinc phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl)Zn Phthalocyanine), octa (1,4,7,10-tetraoxaundecyl)nickel Phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl) Ni Phthalocyanine), octa (1,4,7,10-tetraoxaundecyl)platinium phthalocyanine (Octa (1,4,7,10) -tetraoxaundecyl)Pt Phthalocyanine) and in the group consisting of octa (1,4,7,10-tetraoxaundecyl) chrome phthalocyanine (Octa (1,4,7,10-tetraoxaundecyl) Cr Phthalocyanine) At least one compound. The photosensitive resin composition for a color filter according to claim 1 or 2, comprising: 100 to 250 parts by weight of the reaction based on 100 parts by weight of the adhesive resin The unsaturated compound; 5 to 150 parts by weight of the pigment; 50 to 250 parts by weight of the dye; 5 to 50 parts by weight of the polymerization initiator; and 100 to 500 parts by weight of the solvent. The photosensitive resin composition for a color filter according to claim 1 or 2, wherein the adhesive resin is a co-polymer, and at least one selected from the group consisting of 10 to 40 wt% is selected from the group consisting of (meth)acrylic acid, itaconic acid, maleic acid, fumaric acid, vinyl acetic acid, Single acid group of one group consisting of 2-acryloyloxyethyl hydrogen phthalate and 2-acryloyloxypropyl hydrogen phthalate And at least one of 60 to 90 wt% selected from the group consisting of isobutyl (meth) acrylate, tert-butyl (meth) acrylate, (methyl) ) lauryl (meth) acrylate, ste (meth) aryl acrylate, cyclohexyl (meth) acrylate, (methyl) Isobonyl (meth)acrylate, bezyl (meth)acrylate, 2-hydroxyalkyl (meth)acrylate (2 -hydroxyalkyl(meth)acrylate), trimethoxybutyl (meth)acrylate, ethylcarbitol(meth)acrylate, (meth)acrylic acid Phenoxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, phenoxyethyleneglycol (meth) Acrylate), 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl(meth)acrylate, 2-propene oxime 2-acryloxyethyl 2-hydroxypropyl (meth) phthalate, 2-hydroxy-3-phenoxypropyl (meth) acrylate (2-hydroxy-3-phenoxypropyl(meth)acrylate), triethylsiloxyethyl (meth)acrylate, and ethyltriethylene glycol (meth)acrylate (ethyl) acrylate monomer in the group consisting of (ethyltriglycol (meth)acrylate). The photosensitive resin composition for a color filter according to claim 1 or 2, wherein the reactive unsaturated compound is selected from ethylene glycol di(meth)acrylate (ethyleneglycol di) (meth)acrylate), diethyleneglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, propylene glycol di(meth)acrylate Propyleneglycol di(meth)acrylate, 1,4-butandiol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate 1,6-hexanediol di(meth)acrylate, neopentyllglycol di(meth)acrylate, pentaerythritol di(meth)acrylate (pentaerythritol di(meth) Acetate), pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol penta (meth)acrylate (pentaerythritol penta (pentaerythritol penta) Meth)acrylate), pentaerythritol hexa(meth)acrylate Crylate), dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate (dipentaerythritol) Tetra(meth)acrylate), dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A di(methyl) Bisphenol A di(meth)acrylate, trimethylolpropane tri(methyl)propene Trimethylolpropane tri(meth)acrylate, novolacecoxy(meth)acrylate, dipentaerythritol penta(meth)acrylate derived from carboxyl group Etch, ethylene oxide glycerin trimethylolpropanetri(meth)acrylate, propylene oxide glycerin tri(meth) acrylate (propylene oxide glycerin tri(meth) acrylate) Acrylate, epoxy (meth) acrylate oligomer, urethane (meth) acrylate oligomer, sulfhydryl (meth) At least one compound of the group consisting of thiol (meth) acrylate oligomer and polyester (meth) acrylate oligomer. A color filter produced by using the photosensitive resin composition as described in claim 1 or 2.