KR102222402B1 - Colored photosensitive resin composition - Google Patents

Abstract

The present invention includes a colorant (A), a binder resin (B), a photopolymerizable compound (C), a photoinitiator (D), a solvent (E), and an alicyclic epoxy compound (F);
The colorant (A) comprises a compound represented by the following formula (1), and at least one selected from a pigment and a dye, a color filter prepared using the same, and the color filter. It relates to an image display device.

Description

Colored photosensitive resin composition TECHNICAL FIELD

The present invention relates to a colored photosensitive resin composition, a colored pattern formed from the resin composition, a color filter including the colored pattern, and an image display device having the same.

Color filters are widely used in various display devices such as image pickup devices and liquid crystal displays (LCDs), and their application range is rapidly expanding. The color filters used in the image pickup device and liquid crystal display device are composed of three colored patterns of red, green, and blue, or yellow, magenta, and cyan ( Cyan) consists of three colored colored patterns.

The colored pattern of each of the color filters is generally formed using a colored photosensitive resin composition containing a colorant such as a pigment or dye, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The colored pattern processing using the colored photosensitive resin composition is generally performed by a lithography process.

In recent years, various display devices including solid-state imaging devices such as digital cameras, and color filters for liquid crystal displays (LCDs) are required to have high luminance and high colorability in order to improve processability and quality.

Meanwhile, Korean Patent Publication No. 2013-0134494 discloses C.I Pigment Green 7 and C.I. A resin composition using Pigment Yellow 185 is disclosed, but there is a problem that high luminance and high colorability are not satisfied at the same time.

Republic of Korea Patent Publication No. 2013-0134494

The present invention, as conceived to solve the problem of the prior art,

It is an object of the present invention to provide a colored photosensitive resin composition having excellent luminance and colorability and excellent curability and solvent resistance.

In addition, an object of the present invention is to provide a color filter including the colored photosensitive resin composition and an image display device including the same.

The present invention,

A colorant (A), a binder resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), a solvent (E), and an alicyclic epoxy compound (F);

The colorant (A) provides a colored photosensitive resin composition comprising a compound represented by the following formula (1), and at least one selected from a pigment and a dye.

[Formula 1]

In Formula 1, A ¹ to A ¹⁶ are each independently Cl, Br or H, ^{1 to 6 of A 1} to A ¹⁶ are H, 0 to 5 are Cl, and 5 to 13 are Br.

In addition, the present invention

It provides a color filter including a pattern formed of the colored photosensitive resin composition.

In addition, the present invention

It provides an image display device including the color filter.

The colored photosensitive resin composition of the present invention has characteristics of high luminance and high sensitivity, and can provide an effect excellent in curability and solvent resistance.

1 is a graph showing a transmission spectrum when each colorant is used.

The present invention,

A colorant (A), a binder resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), a solvent (E), and an alicyclic epoxy compound (F);

The colorant (A) provides a colored photosensitive resin composition comprising a compound represented by the following formula (1), and at least one selected from a pigment and a dye.

[Formula 1]

In Formula 1, A ¹ to A ¹⁶ are each independently Cl, Br or H, ^{1 to 6 of A 1} to A ¹⁶ are H, 0 to 5 are Cl, and 5 to 13 are Br.

Hereinafter, each component constituting the colored photosensitive resin composition of the present invention will be described. However, the present invention is not limited to these components.

(A) colorant

The colorant (A) according to the present invention is a component capable of expressing colors such as red, green, or blue so that a pattern having a desired color can be prepared.

Pigment( a1 )

The colorant (A) contained in the colored photosensitive resin composition of the present invention is characterized by containing a compound represented by the following formula (1) as the pigment (a1). The compound represented by Formula 1 below has a structure of ZnPc (Zinc Phthalocyanine). When the coloring agent (A) of the present invention contains a compound represented by the following formula (1) There is an advantage of high color reproduction.

[Formula 1]

In Formula 1, A ¹ to A ¹⁶ are each independently Cl, Br or H, ^{1 to 6 of A 1} to A ¹⁶ are H, 0 to 5 are Cl, and 5 to 13 are Br;

More preferably 1 to 6 are H, 0 to 5 are Cl, and 7 to 13 are Br;

More preferably, 2 to 5 may be H, 0 to 3 may be Cl, and 8 to 13 may be Br. In this case, it is preferable in that the effect of the present invention is further maximized.

C.I. Pigment Green 58 (G58) has the advantage of high luminance, but the content of the pigment increases in order to realize high coloration.If the composition contains a lot of pigment, the developability decreases and the pattern formed by the composition is at risk of peeling off. There is a problem that the sensitivity is lowered may be accompanied.

However, in the present invention, by using the pigment represented by Formula 1 as a colorant, it is possible to design a resist with high color reproduction even if the content of the pigment is small.

On the other hand, when CI Pigment Green 7 (G7) is included in the resin composition, it can exhibit high colorability even if the pigment content is reduced, so that it is advantageous in use, but there is a problem with low luminance. However, the compound of Formula 1 included in the colored photosensitive resin composition of the present invention functions as a pigment to exhibit a transmission spectrum and color coordinates similar to those of CI Pigment Green 7 while being included in the colored photosensitive resin composition to exhibit excellent luminance. As can be seen in FIG. 1, the compound of Formula 1 has a transmission spectrum at a wavelength of 400 nm to 610 nm similar to CI Pigment Green 7.

In the present specification, Tmax means the wavelength at the point where the transmittance of the pigment is the maximum, and T _50% means the wavelength at the point where the transmittance of the pigment is 50% or more of the maximum value.

In one embodiment of the present invention, the Tmax of the compound represented by Formula 1 may be 500 to 530nm, and in this case, it is preferable in terms of excellent colorability.

In addition, in another embodiment of the present invention, T _{50 %} of the compound represented by Formula 1 may be 445 to 580 nm, and in this case, it is preferable in terms of excellent colorability.

The compound of Formula 1 is preferably contained in an amount of 0.05 to 30% by weight based on the total weight of the colored photosensitive resin composition of the present invention, more preferably 0.05 to 25% by weight, and contained in an amount of 0.05 to 20% by weight. It is more preferable. When the compound of Formula 1 is contained within the range of 0.05 to 30% by weight based on the above, it is preferable because it can express a high-brightness resist while having excellent colorability.

The colorant (A) according to the present invention is a component capable of expressing colors such as red, green, or blue so that a pattern having a desired color can be prepared, in addition to the compound of Formula 1, and is a pigment commonly used in the field. And one or more selected from the group consisting of dyes, and may be prepared in the form of a mill base.

The compound represented by Formula 1, and at least one selected from pigments and dyes, is preferably 1: 0.050 to 1: 18.0, more preferably 1: 0.1 to 1: 9, even more preferably 1: 0.2 to It is recommended to be included in a weight ratio of 1: 4. When included in the weight ratio described above, it is preferable because it has the advantages of high coloration and high luminance, and it has the advantages of improved process margin and excellent sensitivity.

In this case, the colorant including the compound of Formula 1 according to the present invention as a pigment may have a color coordinate of x=0.1 to 0.35 when y=0.6 or more in the XYZ color system.

The pigment (a1) includes an organic pigment and an inorganic pigment, and these may be used alone or in combination of two or more. The use of an organic pigment may be more preferable in terms of excellent heat resistance and color development. The organic pigment may be a synthetic colorant or a natural colorant.

If necessary, the organic pigment is rosin treated; Surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced; A graft treatment on the surface of a pigment using a polymer compound or the like; Fine-granulation treatment by a sulfuric acid fine-granulation method or the like; Or washing treatment with an organic solvent or water to remove impurities; It may have been.

Examples of the inorganic pigment include metal compounds such as metal oxides and metal complex salts, inorganic salts of barium sulfate (extender pigment), and the like. More specifically, the metal compounds include iron, cobalt, aluminum, cadmium, lead, copper, and titanium. , Oxides of metals such as magnesium, chromium, zinc, antimony, and carbon black, or complex metal oxides.

As a specific example of the pigment (a1), more preferably, a compound classified as a pigment in the Color Index (Publisher: The Society of Dyers and Colourists) may be mentioned, and more specifically, the following color index ( CI) Pigments exemplified by number may be mentioned, but the present invention is not limited thereto, and at least one selected from them may be used by co-dispersing them using a binder resin, a dispersant, or the like so as to suit the desired chromaticity.

Specific examples of CI pigment yellow include CI pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117 , 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180, 185, 194 and 214, and the like;

Specific examples of the CI pigment orange include CI pigment orange 13, 31, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71 and 73;

Specific examples of CI Pigment Red include CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254 , 255, 264 and 265;

Specific examples of CI Pigment Blue include CI Pigment Blue 15:3, 15:4, 15:6, 16, 22, 28, 60, and the like;

Specific examples of CI pigment violet include CI pigment violet 14, 19, 23, 29, 32, 177, and the like,

As a specific example of CI pigment green, CI pigment green 7, 36, 58, etc. are mentioned.

Among the pigments exemplified above, preferably, it may be more preferable to contain at least one selected from the group consisting of CI pigment yellow 138, CI pigment yellow 129, CI pigment yellow 150, and CI pigment yellow 185. have.

dyes( a2 )

The dye (a2) that may be included in the colorant (A) of the present invention may be used without limitation as long as it has solubility in an organic solvent or is dispersible. It is preferable to use a dye that has solubility in an organic solvent and can secure reliability such as solubility in an alkali developer, heat resistance, and solvent resistance. In the case of a dye that does not have solubility in an organic solvent, it is also possible to disperse and use it.

As the dye (a2), at least one selected from acidic dyes having an acidic group such as sulfonic acid or carboxylic acid, salts of acidic dyes and nitrogen-containing compounds, sulfonamides of acidic dyes, and derivatives thereof may be used. In addition, it is also possible to select from azo-based, xanthene-based, phthalocyanine-based acid dyes and derivatives thereof.

As the dye (a2), preferably, a compound classified as a dye in the color index (published by The Society of Dyers and Colorists), or a known dye described in a dyeing note (color dyeing company) can be mentioned.

Specific examples of the dye (a2),

C.I. Solvent Yellow No. 2, C.I. Solvent Yellow No. 14, C.I. Solvent Yellow No. 16, C.I. Solvent Yellow No. 33, C.I. Solvent Yellow No. 34, C.I. Solvent Yellow No. 44, C.I. Solvent Yellow No. 56, C.I. Solvent Yellow No. 82, C.I. Solvent Yellow No. 93, C.I. Solvent Yellow No. 94, C.I. Solvent Yellow No. 98, C.I. Solvent Yellow No. 116, C.I. Solvent yellow 135;

C.I. Solvent Orange No. 1, C.I. Solvent Orange No. 3, C.I. Solvent Orange No. 7, C.I. Solvent orange 63;

C.I. Solvent Red No. 1, C.I. Solvent Red No. 2, C.I. Solvent Red No. 3, C.I. Solvent Red No. 8, C.I. Solvent Red No. 18, C.I. Solvent Red No. 23, C.I. Solvent Red No. 24, C.I. Solvent Red No. 27, C.I. Solvent Red No. 35, C.I. Solvent Red No. 43, C.I. Solvent Red No. 45, C.I. Solvent Red No. 48, C.I. Solvent Red No. 49, C.I. Solvent Red 91:1, C.I. Solvent Red No. 119, C.I. Solvent Red No. 135, C.I. Solvent Red No. 140, C.I. Solvent Red No. 196, C.I. Solvent Red No. 197;

C.I. Solvent Violet No. 8, C.I. Solvent Purple No. 9, C.I. Solvent Purple No. 13, C.I. Solvent Purple No. 26, C.I. Solvent Purple No. 28, C.I. Solvent Purple No. 31, C.I. Solvent Purple No. 59;

C.I. Solvent Blue No. 4, C.I. Solvent Blue No. 5, C.I. Solvent Blue No. 25, C.I. Solvent Blue No. 35, C.I. Solvent Blue No. 36, C.I. Solvent Blue No. 38, C.I. Solvent blue 70;

CI Solvent Green No. 3, CI Solvent Green No. 5, and CI Solvent Green No. 7, but are not limited thereto.

The colorant (A) may be included in a weight fraction of preferably 5 to 70% by weight, more preferably 10 to 50% by weight, based on the solid content in the colored photosensitive resin composition. If the content of the colorant (A) is less than 5% by weight, the color separation ability of the formed pattern may be lowered, and if it exceeds 70% by weight, lithography performance may be degraded, resulting in problems such as residues or undeveloped.

In the present invention, the solid content in the colored photosensitive resin composition means the total content of the remaining components excluding the solvent from the colored photosensitive resin composition.

(B) binder resin

The binder resin (B) contained in the colored photosensitive resin composition of the present invention is a component that imparts solubility to the alkaline developer used in the developing step. In the present invention, the binder resin is not particularly limited, but it is preferably a copolymer of a monomer having a carboxyl group and another monomer copolymerizable therewith.

The monomer having a carboxyl group is not particularly limited, and specific examples thereof include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; Mono (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both ends, such as ω-carboxypolycaprolactone mono (meth)acrylate, and the like, and acrylic acid and methacrylic acid are more preferable. These can be used by selecting one or more.

The other copolymerizable monomer is not particularly limited as long as it is a monomer having a carbon-carbon unsaturated bond, and specific examples include aromatic vinyl compounds such as styrene, α-methylstyrene, and vinyl toluene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, benzyl meth Unsaturated carboxylate compounds such as acrylate; Unsaturated aminoalkylcarboxylate compounds such as aminoethylacrylate; Unsaturated glycidyl carboxylate compounds such as glycidyl methacrylate; Vinyl carboxylate compounds such as vinyl acetate and vinyl propionate; Vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, and α-chloroacrylonitrile; 3-methyl-3-acryloxymethyloxetane, 3-methyl-3-methacryloxymethyloxetane, 3-ethyl-3-acryloxymethyloxetane, 3-ethyl-3-methacryloxymethyloxetane, 3-methyl-3-acryloxyethyloxetane, 3-methyl-3-methacryloxyethyloxetane, 3-methyl-3-acryloxyethyloxetane, 3-methyl-3-methacryloxyethyloxetane, etc. And unsaturated oxetane carboxylate compounds. These monomers may be used alone or in combination of two or more.

According to the present invention, the molecular weight distribution of the binder resin (B), that is, the weight average molecular weight relative to the number average molecular weight (weight average molecular weight (Mw) / number average molecular weight (Mn)) is preferably 1.5 to 6.0, more preferably It is good in terms of developability to be 1.8 to 4.0.

The binder resin (B) is preferably contained in an amount of 5 to 85% by weight, more preferably 10 to 70% by weight based on the solid content in the colored photosensitive resin composition of the present invention. If the content of the binder resin (B) is 5 to 85% by weight based on the above, the solubility in the developer is sufficient, so that it is difficult to generate a development residue on the substrate in the non-pixel portion, and the film in the pixel portion of the exposed portion during development It is preferable because reduction is prevented and the omission of non-pixel portions tends to be good.

(C) Photopolymerization compound

The photopolymerizable compound (C) contained in the colored photosensitive resin composition of the present invention is a compound that can be polymerized by active radicals, acids, etc. generated from a photopolymerization initiator (D) described later by light irradiation, and is polymerized by the action of a photopolymerization initiator. It does not specifically limit as long as it is a possible compound. Preferably, a monofunctional monomer, a bifunctional monomer, or a trifunctional or higher polyfunctional monomer may be used, and at least one monomer selected from them may be used.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate or N-vinylpi Rolledon, etc. may be mentioned, and commercially available products include Aronics M-101 (Doagosei), KAYARAD TC-110S (Nippon Kayaku), or Biscotti 158 (Osaka Yuki Kagaku High School), but are limited thereto. It is not.

Specific examples of the bifunctional monomer include 1,4-butanedioldi(meth)acrylate, 1,6-hexanedioldi(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylic Rate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, propylene glycol dimethacrylate, urethane (meth)acrylate Commercially available products include Aaronix M-210, M-1100, 1200 (Doagosei), KAYARAD HDDA (Nippon Kayaku), Viscot 260 (Osaka Yuki Kagaku High School), AH-600, AT- 600 or UA-306H (Kyoeisha Chemical Co.), and the like, but are not limited thereto.

Specific examples of the trifunctional or higher polyfunctional photopolymerizable compound include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate , Pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol penta(meth)acrylate, ethoxyl Rated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like. -309, TO-1382 (Doagosei), KAYARAD TMPTA, KAYARAD DPHA or KAYARAD DPHA-40H (Nippon Kayaku), and the like, but is not limited thereto.

It is more preferable to use a trifunctional or higher polyfunctional monomer among the photopolymerizable compounds exemplified above, and (meth)acrylates and urethane (meth)acrylates have excellent polymerization properties and can improve strength. desirable.

The photopolymerizable compound (C) is preferably contained in an amount of 5 to 45% by weight, more preferably 10 to 35% by weight, based on the solid content in the colored photosensitive resin composition of the present invention. When the photopolymerizable compound (C) is in the range of 5 to 45% by weight based on the above, it is preferable because the strength and smoothness of the pixel portion become good.

(D) Light polymerization Initiator

The photopolymerization initiator (D) contained in the colored photosensitive resin composition of the present invention initiates polymerization of the photopolymerizable compound (C) described above by exposure to radiation such as visible light, ultraviolet rays, far ultraviolet rays, electron rays, and X-rays. It is a compound that generates radicals and the like.

The photopolymerization initiator is commonly used in the art within a range that does not impair the object of the present invention, and the type of the photopolymerization initiator is not particularly limited as long as it can polymerize the binder resin and the photopolymerizable compound. Representative examples include, but are limited to, oxime compounds, acetophenone compounds, benzoin compounds, benzophenone compounds, biimidazole compounds, triazine compounds, thioxanthone compounds, and anthracene compounds. It is not, and one or more can be selected and used from this. Among these, it may be more preferable to use an oxime compound in consideration of polymerization characteristics, initiation efficiency, absorption wavelength, and the like.

Examples of the oxime compound include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, (Z)-2-((benzoyloxy)imino)-1-(4- (Phenylthio)phenyl)octan-1-one (see formula 3 below), (E)-1-(((1-(9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3- Yl) ethylidine) amino) oxy) ethanone (see formula 4 below) and (E) -1-(((1-(6-(4-((2,2-dimethyl-1,3-dioxolane-)) 4-yl)methoxy)-2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl)ethylidine)amino)oxy)ethanone (see formula 5 below), and the like. OXE-01, OXE-02, etc. of BASF may be mentioned, but are not limited thereto.

[Formula 3]

[Formula 4]

[Formula 5]

In the present invention, the oxime-based compound is not particularly limited in its content as long as it is within a range capable of fulfilling its functions, and preferably may be included in an amount of 10 to 100% by weight based on the total weight of the photopolymerization initiator (D). When the content of the oxime compound is within the above range, brightness and sensitivity can be maximized.

Examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, and 2-hydroxy-1-[4-(2- Hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one , 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propane- 1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, and the like.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

Examples of the benzophenone-based compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra( tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, and the like.

Examples of the biimidazole-based compound compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2, 3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) Biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, 2,2-bis(2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole or imidazole compounds in which the phenyl group at the 4,4',5,5' position is substituted with a carboalkoxy group. Among these, more preferably 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole or 2,2-bis(2,6-dichlorophenyl)-4,4'5,5'-tetraphenyl-1,2'-biimidazole And the like.

Examples of the triazine-based compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)- 6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4- Bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2) -Yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-tri Azine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloro Methyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

Examples of the thioxanthone compound include 2-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichloro thioxanthone, 1-chloro-4-propoxy thioxanthone, etc. Can be mentioned.

Examples of the anthracene-based compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, etc. Can be mentioned.

Other specific examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9,10-phenanthrenequinone, campoquinone, phenylclioxyl Acid methyl, titanocene compounds, and the like.

The content of the photopolymerization initiator (D) is not particularly limited, but is preferably contained in an amount of 0.1 to 40% by weight based on the total weight of the solids in the binder resin (B) and the photopolymerizable compound (C), and 1 to 30% by weight It is more preferable to be included in %. When the content of the photopolymerization initiator is within the above range, the colored photosensitive resin composition is highly sensitive and thus the exposure time is shortened, so that productivity is improved and high resolution can be maintained. Further, the strength of the pixel portion formed by using the colored photosensitive resin composition of the present invention and the smoothness on the surface of the pixel portion can be improved, which is preferable.

(E) solvent

As long as the solvent (E) according to the present invention is effective in dissolving other components included in the colored photosensitive resin composition, a solvent commonly used in the art may be used without particular limitation. As a specific example, the solvent may be used by selecting one or more from ethers, acetates, aromatic hydrocarbons, ketones, alcohols, esters, and amides, but is not limited thereto.

Specifically, the ether solvents include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether;

Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; And the like.

The acetate solvents are specifically, alkylene glycol alkyl ether acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and the like. ;

Alkoxyalkyl acetates such as methoxybutyl acetate and methoxypentyl acetate; And the like.

Specific examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

Specific examples of the ketone solvent include methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone.

Specific examples of the alcohol solvent include ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.

Specifically, the ester solvents include cyclic esters such as γ-butyrolactone;

3-ethoxy ethylpropionate, 3-methoxy methylpropionate, ethyl 3-ethoxypropionate, etc. are mentioned.

Specific examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

The solvent (E) is preferably an organic solvent having a boiling point of 100° C. to 200° C. in terms of coating properties and drying properties, more preferably alkylene glycol alkyl ether acetates; Ketones; Esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate; more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 3-ethoxypropionic acid Ethyl, methyl 3-methoxypropionate, and the like. These solvents may be used alone or in combination of two or more.

The content of the solvent (E) contained in the colored photosensitive resin composition of the present invention is preferably contained in an amount of 60 to 90% by weight, more preferably 70 to 85% by weight, based on the total weight of the colored photosensitive resin composition of the present invention. Can be included as. When the solvent (E) is contained within the above-described range, the coating property becomes good when applied with a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), or inkjet. It can provide an effect.

(F) Alicyclic Epoxy compound

The colored photosensitive resin composition of the present invention contains an alicyclic epoxy compound (F) as a curing agent for improving curing performance. As a specific example, the alicyclic epoxy compound may be one or more selected from the following compounds (1) to (22), but is not limited thereto.

In the compounds (1) to (22), R ¹ to R ⁴⁴ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms;

Y ¹ is an oxygen or alkanediyl group; Y ² to Y ²¹ are each independently an alkanediyl group;

Z ¹ to Z ² are each independently an alkane triyl group;

T ¹ is an alkanetetrayl group having 1 to 20 carbon atoms; And

a to r are each independently an integer of 0 to 20.

More specifically, R ¹ to R ⁴⁴ are each independently hydrogen; Or a straight chain, branched or cyclic C1-C6 alkyl group having an alicyclic ring, of which the C1-C6 alkyl group is advantageous in terms of curing speed. R ¹ When to R ⁴⁴ is an alkyl group, the position bonded to the alicyclic ring is not particularly limited.

In addition, Y ¹ is an oxygen or alkanediyl group, and Y ² to Y ²¹ are each independently a cyclic alkanediyl group having a linear, branched or alicyclic ring. Among them, Y ² , Y ⁴ , Y ⁹ , Y ¹⁰ , Y ¹¹ , Y ¹² , Y ¹³ , Y ¹⁴ , Y ¹⁵ , Y ¹⁶ , Y ¹⁸ , Y ¹⁹ , Y ²⁰ , and Y ²¹ are eggs with 1 to 20 carbon atoms. It is a caldiyl group, and it is preferable that Y ¹ , Y ³ , Y ⁵ , Y ⁶ , Y ⁷ , Y ⁸ , and Y ¹⁷ are alkanediyl groups having 2 to 20 carbon atoms.

In addition, Z ¹ and Z ² are each independently an alkane triyl group having a linear, branched or alicyclic ring, of which Z ¹ is an alkanetriyl group having 2 to 20 carbon atoms, and Z ² is an alkane having 1 to 20 carbon atoms It is preferably a triyl group.

Moreover, ^{it is preferable that T 1} is a C1-C20 alkanetetrayl group which has a linear, branched, or alicyclic ring.

In addition, it is preferable that a to r are each independently an integer of 0 to 20.

As the alicyclic epoxy compound (F) of the present invention, when at least one selected from the aforementioned compounds (1) to (22) is used, a colored photosensitive resin composition exhibiting high luminance and excellent in solvent resistance and heat resistance can be provided. It is desirable because it has the advantage of being able to.

The alicyclic epoxy compound (F) may be generally contained in an amount of 0.02 to 10% by weight, more preferably 0.05 to 3% by weight, based on the solid content in the colored photosensitive resin composition of the present invention. When the content is contained within the range of 0.02 to 10% by weight based on the above, a resist having high brightness, good solvent resistance, and excellent heat resistance can be provided.

(G) additive

In addition to the above components, the colored photosensitive resin composition of the present invention includes additives such as other polymer compounds, surfactants, adhesion promoters, antioxidants, anti-aggregation agents, and pigment dispersants as needed by those skilled in the art within a range that does not impair the object of the present invention. ) May be further included.

As a specific example of the other polymer compound, a curable resin such as epoxy resin, maleimide resin, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, thermoplastic resin such as polyurethane, etc. However, it is not limited thereto.

The surfactant may be used to further improve the film formation property of the photosensitive resin composition, and as a specific example of the surfactant, a fluorine-based surfactant or a silicone-based surfactant may be preferably used.

Examples of the fluorine-based surfactant are commercially available products, such as Megapieces F-470, F-471, F-475, F-482, F-489, etc. manufactured by Dai Nippon Ink Chemical Co., Ltd.

Examples of the silicone surfactant are commercially available products such as DC3PA, DC7PA, SH11PA, SH21PA, and SH8400 of Dow Corning Toray Silicone, and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF- 4460 and TSF-4452.

Each of the above-exemplified surfactants may be used alone or in combination of two or more.

As specific examples of the adhesion promoter, vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2 -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyl At least one selected from trimethoxysilane, 3-isocyanatepropyltrimethoxysilane, and 3-isocyanatepropyltriethoxysilane may be used.

The adhesion promoter may be included in an amount of 0.01 to 10% by weight, more preferably 0.05 to 2% by weight, based on the solid content in the colored photosensitive resin composition of the present invention.

As a specific example of the antioxidant, 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, 2-[1-(2-hydroxy -3,5-di-tert-pentylphenyl)ethyl]-4,6-di-tert-pentylphenylacrylate, 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)prop Foxy]- 2,4,8,10 -tetra-tert-butyldibenz[d,f][1,3,2]dioxaphosphepine, 3,9-bis[2-{3-(3-tert) -Butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 2,2'-methylenebis( 6-tert-butyl-4-methylphenol), 4,4'-butylidenebis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(2-tert-butyl-5- Methylphenol), 2,2'-thiobis(6-tert-butyl-4-methylphenol), dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate , Distearyl 3,3'-thiodipropionate, pentaerythrityltetrakis (3-laurylthiopropionate), 1,3,5-tris (3,5-di-tert-butyl- 4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 3,3',3'',5,5',5''- Hexa-tert-butyl-a,a',a''-(mesitylene-2,4,6-triyl)tri-p-cresol, pentaerythritol tetrakis[3-(3,5-di-tert) -Butyl-4-hydroxyphenyl)propionate], 2,6-di-tert-butyl-4-methylphenol and 2,2'-thiobis(4-methyl-6-t-butylphenol), 2 ,6-di-t-butyl-4-methylphenol, and the like, but are not limited thereto.

Specific examples of the anti-aggregation agent may include sodium polyacrylate, but are not limited thereto.

The pigment dispersant is a component that can be added for deagglomeration and stability maintenance of the pigment (a1). As an example of a method for uniformly dispersing the particle diameter of the pigment (a1), there is a method of dispersing by adding a pigment dispersant, and through this, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

The pigment dispersant generally used in the art may be used without limitation. Preferably, an acrylate-based dispersant (hereinafter also referred to as an “acrylic dispersant”) including butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA) may be used. Commercially available products of the acrylate-based dispersant include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150, and DISPER BYK LPN-6919. Each of the acrylic dispersants exemplified above may be used alone or in combination of two or more.

In addition to the above-described acrylate-based dispersant, the pigment dispersant may use other resin type pigment dispersants. As the pigment dispersant of the other resin type, a known resin type pigment dispersant, in particular, of a polycarboxylic acid ester typified by polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and modified products thereof, or free An oily pigment dispersant such as an amide formed by reaction of a polyester having a carboxyl group with a poly (lower alkyleneimine) or a salt thereof; Water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinyl pyrrolidone; Polyester; Modified polyacrylate; And phosphate esters and adducts of ethylene oxide/propylene oxide.

As a commercial item of the above resin type pigment dispersant, for example, the brand names of BYK-Chemi: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK- 166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF's brand names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Trade names of Lubirzol: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; Kawaken Fine Chemical's trade names: Hinoact T-6000, Hinoact T-7000, Hinoact T-8000; Ajinomoto's brand names: AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823; Kyoeisha Chemicals' brand name: FLORENE DOPA-17HF, Floren DOPA-15BHF, Floren DOPA-33, Floren DOPA-44, and the like.

The manufacturing method of the colored photosensitive resin composition of the present invention will be described as an example as follows.

First, the pigment (a1) of the colorant (A) is mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, some or all of the pigment dispersant, the binder resin (B), or the dye (a2) may be mixed with the solvent (E) to dissolve or disperse.

In the mixed dispersion, the dye (a2), the remainder of the binder resin (B), the photopolymerizable compound (C) and the photopolymerization initiator (D), and optionally additives (F) and solvents (E) are added to a predetermined concentration. It can be added to prepare a colored photosensitive resin composition according to the present invention.

Further, the present invention includes a colored pattern made of the colored photosensitive resin composition. The colored pattern may be prepared by applying the colored photosensitive resin composition of the present invention on a substrate, photocuring, and developing. The thickness of the colored pattern is not particularly limited, and may be, for example, 1 to 6 μm.

The colored pattern may be formed, for example, in the following manner.

First, the colored photosensitive resin composition is applied onto a substrate or a layer consisting of a solid content of the previously formed photosensitive resin composition, and prebaked from the applied photosensitive resin composition layer to remove volatile components such as a solvent to obtain a smooth coating film.

As the coating method, for example, spin coating, casting coating, roll coating, slit-and-spin coating, or slit coating can be performed.

After the above application, a colored photosensitive resin composition layer is formed by heating after prebaking (heat drying) or drying under reduced pressure to volatilize volatile components such as a solvent. Here, the heating temperature is usually 70 to 200°C, preferably 80 to 130°C.

The thus obtained coating film is irradiated with ultraviolet rays through a mask for forming a target pattern. At this time, it is preferable to use a device such as a mask aligner or a stepper so that parallel light rays are uniformly irradiated to the entire exposed portion and accurate alignment of the mask and the substrate is performed.

Further, after that, the cured coating film is brought into contact with an alkali developer to dissolve and develop the non-exposed portion, whereby a desired pattern shape can be obtained. As the developing method, a liquid addition method, a dipping method, a spray method, or the like may be performed, and the substrate may be tilted at an arbitrary angle during development.

The developer used for development after patterning exposure is usually an aqueous solution containing an alkaline compound and a surfactant. The alkaline compound may be any of inorganic and/or organic alkaline compounds.

Specific examples of the inorganic alkaline compound include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, carbonic acid. Potassium, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium borate, potassium borate, ammonia, etc. are mentioned.

Specific examples of the organic alkaline compound include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, mono Isopropylamine, diisopropylamine, ethanolamine, etc. are mentioned. These inorganic and organic alkaline compounds may be used alone or in combination of two or more.

The concentration of the alkaline compound in the alkali developer is, for example, 0.01 to 10% by weight, more preferably 0.03 to 5% by weight.

The surfactant in the alkaline developer may be any of a nonionic surfactant, an anionic surfactant, or a cationic surfactant.

Specific examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene/oxypropylene block copolymers, and sorbitan fatty acids. Ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alkylamine, and the like.

Specific examples of the anionic surfactant include higher alcohol sulfuric acid ester salts such as sodium lauryl alcohol sulfate and sodium oleyl alcohol sulfate; Alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate; Alkylarylsulfonic acid salts such as sodium dodecylbenzenesulfonate and sodium dodecylnaphthalenesulfonate; And the like.

Specific examples of the cationic surfactant include amine salts such as stearylamine hydrochloride or lauryltrimethylammonium chloride; Quaternary ammonium salt; And the like.

These surfactants can be used alone or in combination of two or more.

The concentration of the surfactant in the alkaline developer is, for example, 0.01 to 10% by weight, preferably 0.05 to 8% by weight, and more preferably 0.1 to 5% by weight.

After the above development, washing with water may be performed, and post-baking for 10 to 60 minutes at 150 to 230° C. may be performed as needed.

<Color filter>

In addition, the present invention provides a color filter including a colored pattern made of the colored photosensitive resin composition. The color filter of the present invention includes a substrate and a colored pattern made of the colored photosensitive resin composition of the present invention on the substrate. The substrate is a transparent material, and a material having sufficient strength and support for stability of the color filter may be used. Preferably, glass having excellent chemical stability and high strength can be used.

As a method of manufacturing the color filter, a conventional method well known in the art may be used.

<Image display device>

Further, the present invention provides an image display device including the color filter. Specific examples of the image display device include a liquid crystal display (liquid crystal display; LCD), an organic EL display (organic EL display), a liquid crystal projector, a display device for a game machine, a display device for a portable terminal such as a mobile phone, and a display for a digital camera. And display devices such as a device and a display device for car navigation. In particular, a color display device is suitable.

The image display device includes a configuration known to a person skilled in the art, except that the color filter is provided, that is, the present invention includes an image display device to which the color filter of the present invention can be applied. .

Hereinafter, the present invention will be described in more detail using Examples and Comparative Examples. However, the following examples are intended to illustrate the present invention, and the present invention is not limited by the following examples, and various modifications and changes can be made within the scope of the present invention. The scope of the present invention will be determined by the technical idea of the claims to be described later.

In addition, "%" and "parts" indicating the content in the following Preparation Examples, Examples, and Comparative Examples are based on weight unless otherwise noted.

Preparation of colored photosensitive resin composition

To prepare a colored photosensitive resin composition having the composition and content shown in Table 1 below.

(weight%) division Example 1 Example 2 Comparative Example 1 Comparative Example 2 coloring agent
(A) A-1 3.90 3.90 3.90 3.90 A-2 2.40 2.40 2.40 2.40 Binder Resin (B) B-1 5.00 5.00 5.00 5.20 Photopolymerizable compound
(C) C-1 2.85 2.85 2.85 3.00 Photopolymerization
Initiator (D) D-1 0.30 0.30 0.30 0.30 Solvent (E) E-1 17.00 17.00 17.00 17.00 E-2 68.00 68.00 68.00 68.00 Cycloaliphatic epoxy
Compound (F) F-1 0.35 - - F-2 0.35 Additive (G) G-1 - - 0.35 - G-2 0.10 0.10 0.10 0.10 G-3 0.10 0.10 0.10 0.10 A-1: In the structure of Formula 1, Cl: 2, Br: 9, H: 5 (DIC), (Tmax: 515nm, T _{50 %} : 450 to 575nm)
A-2: Y129 (manufacturer: DIC)
B-1: Methacrylic acid: benzyl methacrylate = 31:69 (molar ratio), weight average molecular weight = 30,000, acid value = 105 copolymer of methacrylic acid and benzyl methacrylate
C-1: Dipentaerythritol hexaacrylate (KAYARAD DPHA; Manufacturer: Nippon Kayaku Co., Ltd.)
D-1: OXE-01 (manufacturer: Ciba)
E-1: Propylene glycol monomethyl ether acetate
E-2: ethyl 3-ethoxypropionate
F-1: CEL2021: (3'-4'-epoxycyclohexane) methyl 3'-4'-epoxycyclohexyl-carboxylate (Dicel Chemical Industries)
F-2: CEL3000: 1, 2, 8, 9-diepoxylimonene (Daicel Chemical Industries)
G-1: CNE-195XL-16 (CHANG CHUN PLASTICS CO., LTD)
G-2: Silicone surfactant (SH-8400)
G-3: adhesion promoter (3-methacryloxypropyltrimethoxysilane)

< Manufacturing example > Manufacturing of color filters

A color filter was manufactured using the colored photosensitive resin composition prepared in Examples 1 to 2 and Comparative Examples 1 to 2.

Each of the above colored photosensitive resin compositions was coated on a glass substrate by spin coating, and then placed on a heating plate and held at a temperature of 100° C. for 3 minutes to form a thin film. Subsequently, a test photomask having a pattern for changing the transmittance in a stepwise shape in the range of 1 to 100% and a line/space pattern of 1 µm to 50 µm is placed on the thin film, and the distance between the test photo mask is set to 100 µm. Was investigated. ^{At this time, the ultraviolet light source was irradiated with an illuminance of 100 mJ/cm 2} using a 1KW high-pressure mercury lamp containing all g, h, and i lines, and no special optical filter was used. The UV-irradiated thin film was developed by immersing it in a developing solution of a KOH solution having a pH of 10.5 for 2 minutes. The glass plate coated with this thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 220° C. for 1 hour to prepare a color filter. The film thickness of the color filter prepared above was 3.0 µm.

< Experimental example > Evaluation of colored photosensitive resin composition

Experimental example 1. Luminance measurement

The luminance was measured using a microscopic spectrometer OSP-SP2000, and the results are shown in Table 2 below.

<Brightness evaluation criteria>

○: Excellent luminance improvement-Luminance (Y)=33 or more at the same x,y value (Gx=0.213, Gy=0.683 standard)

×: Poor luminance improvement-luminance (Y) = less than 33 based on the same x and y values (Gx = 0.213, Gy = 0.683)

Experimental example 2: Solvent resistance Measure

The prepared color filter was immersed in an N-methylpyrrolidone solvent for 30 minutes to compare and evaluate the color change before and after the evaluation. The equation used at this time is calculated by the following equation (1) representing the color change in a three-dimensional colorimeter defined by L*, a*, and b*, and the smaller the color change value, the more reliable color filters can be manufactured.

<Equation 1>

△Eab* =[(△L*) ² +(△a*) ² +(△b*) ² ] ^1/2

○: Excellent chemical resistance-No change in pattern, △(Eab*) is less than 3.0

△: Good chemical resistance-There is a slight change in pattern, or △(Eab*) is 3.0 or more and less than 5.0

×: Poor chemical resistance-There is a change in pattern, or △(Eab*) is 5.0 or more

Experimental example 3: Heat resistance evaluation

Each of the colored photosensitive resin compositions prepared in Examples 1 to 2 and Comparative Examples 1 to 2 was spin-coated using a spin coater, and rotated so that the film thickness after drying was 2.5 μm on a glass substrate of 50 mm×50 mm. After adjusting the number and applying, it was dried for 3 minutes in an oven at 100°C. The dried substrate was exposed so that the distance between the photomask and the photomask was 300 µm, and the accumulated light amount of 313 nm wavelength of the fusion lamp was 40 mJ/cm ² to prepare a color filter. Then, using a spray developing apparatus, after developing with a KOH aqueous solution of pH 10.5 for 1 minute, it washed with water, and air-dried. Then, it was cured in an oven at 230°C for 20 minutes. Then, the color change (heat resistance) before and after 230°C/2hr was compared and evaluated.

It is calculated by the following equation (1) representing the color change in a three-dimensional colorimeter defined by L*, a*, and b*, and the smaller the color change value, the more reliable color filters can be manufactured.

<Equation 1>

△Eab* =[(ΔL*) ² +(Δa*) ² +(Δb*) ² ] ^1/2

<Evaluation criteria>

△Eab 2 or less: Excellent

ΔEab 2 or more to 3 or less: equivalent

△Eab 3 exceeded: Bad

Luminance Solvent resistance Heat resistance Example 1 O O Great Example 2 O O Great Comparative Example 1 X O Bad Comparative Example 2 O X equal

As can be seen from the results of Table 2, based on the same color coordinates, the colored photosensitive resin compositions of Examples 1 to 2 belonging to the scope of the present invention exhibit excellent luminance, and it can be confirmed that the solvent resistance and heat resistance are also excellent.

On the other hand, the colored photosensitive resin compositions of Comparative Examples 1 to 2 exhibited unsuitable results in one or more of luminance, solvent resistance, and heat resistance evaluation.

Claims (12)

A colorant (A), a binder resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), a solvent (E), and an alicyclic epoxy compound (F);
The colorant (A) includes a compound represented by the following formula (1), and at least one selected from a pigment and a dye;
The alicyclic epoxy compound (F) is a colored photosensitive resin composition, characterized in that at least one selected from the following compounds (1) to (22):
[Formula 1]

In Formula 1, A ¹ to A ¹⁶ are each independently Cl, Br or H, ^{1 to 6 of A 1} to A ¹⁶ are H, 0 to 5 are Cl, and 5 to 13 are Br;

In the compounds (1) to (22), R ¹ to R ⁴⁴ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms;
Y ¹ is an oxygen or alkanediyl group; Y ² to Y ²¹ are each independently an alkanediyl group;
Z ¹ to Z ² are each independently an alkane triyl group;
T ¹ is an alkanetetrayl group having 1 to 20 carbon atoms; And
a to r are each independently an integer of 0 to 20. delete The method according to claim 1,
The compound represented by Formula 1 is a colored photosensitive resin composition, characterized in that contained in an amount of 0.05 to 30% by weight based on the total weight of the colored photosensitive resin composition. The method according to claim 1,
As a weight fraction with respect to the solid content in the colored photosensitive resin composition,
5 to 70% by weight of the colorant (A); And
A colored photosensitive resin composition comprising 0.02 to 10% by weight of an alicyclic epoxy compound (F). The method according to claim 1,
A colored photosensitive resin composition, characterized in that the compound represented by Chemical Formula 1 and at least one selected from pigments and dyes are included in a weight ratio of 1: 0.050 to 1: 18.0. The method according to claim 1,
In Chemical Formula 1, ^{1 to 6 of A 1} to A ¹⁶ are H, 0 to 5 are Cl, and 7 to 13 are Br. The method according to claim 1,
In Chemical Formula 1, ^{2 to 5 of A 1} to A ¹⁶ are H, 0 to 3 are Cl, and 8 to 13 are Br. The method according to claim 1,
A colored photosensitive resin composition further comprising one or more additives selected from other polymer compounds, surfactants, adhesion promoters, antioxidants, anti-aggregation agents, and pigment dispersants. The method according to claim 1,
A colored photosensitive resin composition, characterized in that the Tmax of the compound represented by Formula 1 is 500 to 530 nm. The method according to claim 1,
_{T 50 %} of the compound represented by Formula 1 is a colored photosensitive resin composition, characterized in that 445 to 580 nm. A color filter comprising a colored pattern made of the colored photosensitive resin composition according to any one of claims 1 to 10. An image display device comprising the color filter of claim 11.

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