KR20200064822A - A red photosensitive resin composition, a color filter comprising the same, and a display devide comprising the color filter - Google Patents

Abstract

The present invention provides a red-color photosensitive resin composition, a color filter manufactured using the same, and a display device comprising the color filter. In particular, the red-color photosensitive resin composition comprises a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E), wherein the colorant (A) includes one or more selected from the group consisting of C.I. Pigment Red 179 and C.I. Pigment Red 264, the photopolymerization initiator (D) includes one or more selected from the group consisting of carbazole-based compounds and fluorene oxime-based compounds, and a thin film manufactured with the red-color photosensitive resin composition has a spectrum transmittance of 10% or less in the range of 590-595 nm.

Description

A red photosensitive resin composition, a color filter manufactured using the same, and a display device including the color filter {A RED PHOTOSENSITIVE RESIN COMPOSITION, A COLOR FILTER COMPRISING THE SAME, AND A DISPLAY DEVIDE COMPRISING THE COLOR FILTER}

The present invention relates to a red photosensitive resin composition, a color filter manufactured using the same, and a display device including the color filter.

The color filter is widely used in various display devices such as an imaging device and a liquid crystal display (LCD), and its application range is rapidly expanding. The color filter used in the image pickup device, the liquid crystal display device, etc. is composed of three colored patterns of red, green, and blue, or yellow, magenta, and cyan ( Cyan) consists of three colored coloring patterns.

The coloring pattern of each of the color filters is generally formed using a coloring photosensitive resin composition containing a coloring agent such as a pigment or dye, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The coloring pattern processing using the coloring photosensitive resin composition is usually performed by a lithography process.

The color filter is an essential material for liquid crystal display materials, organic light-emitting devices, displays, etc., and requires high reliability properties such as solvent resistance and adhesion. Also, the color filter has been further improved according to the recent trend of large screen and high-definition display. Technology development is required.

Republic of Korea Patent No. 10-1648607 discloses a technique related to an ink composition having an improved contrast ratio reduction under an external light source, a color filter manufactured using the same, and a display device including the color filter, but has low reliability when curing at a low temperature. There is a problem, and it seems that the color purity of the RED spectrum is also insufficient.

Republic of Korea Registered Patent No. 10-1648607

The present invention is intended to improve the above-mentioned conventional technical problems, and to improve the color purity of the RED spectrum, and at the same time, to provide a red photosensitive resin composition having excellent reliability such as solvent resistance and adhesion.

In addition, an object of the present invention is to improve the color characteristics of a red device including a thin film prepared using the red photosensitive resin composition.

In addition, an object of the present invention is to provide a color filter manufactured using the red photosensitive resin composition and a display device including the color filter.

In order to achieve the above object, the present invention is a red photosensitive resin composition comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent. (A) Colorant is CI Pigment Red 179 and C.I. Pigment Red 264 comprises at least one selected from the group consisting of, the (D) photopolymerization initiator comprises at least one selected from the group consisting of carbazole-based and fluorene oxime-based, prepared by the red photosensitive resin composition The resulting thin film provides a red photosensitive resin composition having a spectral transmittance in the range of 590 nm to 595 nm of 10% or less.

In addition, the present invention provides a color filter comprising a colored pattern made of the red photosensitive resin composition.

In addition, the present invention provides a display device including the color filter.

The red photosensitive resin composition of the present invention is a C.I. Pigment Red 179 and C.I. 590nm to 595nm for the thin film produced by using at least one selected from the group consisting of Pigment Red 264 and containing at least one selected from the group consisting of carbazole-based and fluorene oxime-based photopolymerization initiators The spectral peak transmittance of the range is 10% or less, and the spectral transmittance of 600 nm or more can satisfy the characteristics of 20% or more, thereby improving the color purity of the RED spectrum, and at the same time, the solvent resistance and adhesion can also achieve excellent effects. .

In addition, it provides an effect of improving the color characteristics of a red device comprising a thin film prepared using the red photosensitive resin composition.

In addition, a color filter manufactured using the red photosensitive resin composition and a display device including the color filter provide excellent characteristics in driveability and durability.

1 is a view showing a criterion for evaluating adhesion in the present invention.
Figure 2 is a graph measuring the spectral transmittance of a thin film made of a red photosensitive resin composition of Examples and Comparative Examples according to the present invention.
3 is an enlarged graph of a portion having a wavelength range of 590 nm to 600 nm in FIG. 2.

The present invention is a red photosensitive resin composition comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent, wherein the (A) colorant is C.I. Pigment Red 179 and C.I. Pigment Red 264 comprises at least one selected from the group consisting of, the (D) photopolymerization initiator comprises at least one selected from the group consisting of carbazole-based and fluorene oxime-based, prepared by the red photosensitive resin composition The thin film to be provided provides a red photosensitive resin composition having a spectral transmittance in the range of 590 nm to 595 nm of 10% or less, a color filter prepared using the same, and a display device including the color filter.

The red photosensitive resin composition according to the present invention is a C.I. Pigment Red 179 and C.I. 590nm to 595nm of a color filter produced using the same by using at least one selected from the group consisting of Pigment Red 264 and containing at least one selected from the group consisting of carbazole-based and fluorene oxime-based photopolymerization initiators It is possible to improve the color purity of the RED spectrum by satisfying the characteristics of the maximum spectral transmittance of 10% or less in the range and the spectral transmittance of 600nm or more in 20% or more, and at the same time, reliability such as solvent resistance and adhesion also provides a very good effect. Can be.

Therefore, it is possible to provide an effect of improving color characteristics of a red device including a thin film prepared using the red photosensitive resin composition according to the present invention.

Red photosensitive resin composition

Hereinafter, each component constituting the red photosensitive resin composition of the present invention will be described in detail. However, the present invention is not limited by these components.

(A) Coloring agent

The colorant is C.I. Pigment Red 179 and C.I. It characterized in that it comprises at least one selected from the group consisting of Pigment Red 264, and may further include at least one pigment (a1), at least one dye (a3), or a mixture thereof.

C.I. Pigment Red 179 and C.I. As it includes at least one selected from the group consisting of Pigment Red 264, as can be seen in FIG. 2, the spectral transmittance of the color filter manufactured using it is shifted to the right as a whole, whereby the color purity of the RED spectrum can be seen. Can be improved.

That is, as the spectral transmittance of the color filter moves to the right of the red wavelength series, the spectral transmittance of 590 nm to 595 nm range is 10% or less, and the spectral transmittance of 600 nm or more may be 20% or more, preferably 590 nm to 595 nm The maximum transmittance of the spectrum is 1% or more to 10% or less, and the spectrum transmittance of 600 nm or more may be 20% or more to 100% or less.

(a1) pigment

The pigment may be an organic pigment or an inorganic pigment commonly used in the art, and these may be used alone or in combination of two or more. In addition, the pigment may be subjected to resin treatment, surface treatment using a pigment derivative having an acidic or basic group introduced, if necessary, graft treatment of a pigment surface with a polymer compound, atomization treatment with a sulfuric acid atomization method, etc. to remove impurities. A washing treatment with an organic solvent, water, or the like, or removal treatment of ionic impurities by an ion exchange method or the like can also be performed.

As the organic pigment, various pigments used in printing ink, inkjet ink, and the like can be used, specifically, water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, Perylene pigments, perinone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinonyl pigments, anthrapyrimidine pigments, anthantrone pigments, indanthrone pigments, pravanthrone pigments, pyranthrone pigments, diketopyrrolopyrrole pigments And the like.

In addition, a metal compound such as a metal oxide or a metal complex salt may be used as the inorganic pigment. Specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, carbon black, organic And oxides of metals such as black pigments, titanium blacks and reds, greens, and blues, and black pigments, or composite metal oxides.

In particular, examples of the organic pigments and inorganic pigments include compounds classified as pigments in the color index (published by The society of Dyers and Colourists), and more specifically, the following color index (CI) numbers. Pigments can be mentioned, but are not limited to these.

C.I. Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 And 185;

C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 208, 215, 216, 224, 242, 254 and 255;

C.I pigment black 1 and 7;

The pigment is preferably C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Orange 38, C.I. Pigment Red 122, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 208, C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 255.

The pigment may be included in 5 to 60% by weight, preferably 10 to 45% by weight based on the total weight of solids in the red photosensitive resin composition. When the pigment is included in the above range, it is preferable to form a thin film, since the color density of the pixel is sufficient, and since the omission of the non-pixel portion does not decrease during development, residues are not generated.

It is preferable to use a pigment dispersion liquid in which the particle diameter of the pigment is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of a pigment may include a method of dispersing by containing a pigment dispersant (a2), and according to the above method, a pigment dispersion liquid in which the pigment is uniformly dispersed in a solution can be obtained. have.

(a2) pigment dispersant

The pigment dispersant is added to maintain the deagglomeration and stability of the pigment, and can be used without limitation, generally used in the art. Specific examples of the pigment dispersant are cationic, anionic, nonionic, and amphoteric, Surfactants, such as polyester type and polyamine type, etc. are mentioned, These can be used individually or in combination of 2 or more types.

Specific examples of the cationic surfactant include amine salts such as stearylamine hydrochloride and lauryl trimethylammonium chloride or quaternary ammonium salts.

Specific examples of the anionic surfactant include higher alcohol sulfate ester salts such as sodium lauryl alcohol sulfate ester and sodium oleyl alcohol sulfate, alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate, sodium dodecylbenzenesulfonate, and And alkyl aryl sulfonates such as sodium dodecyl naphthalene sulfonate.

Specific examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene/oxypropylene block copolymer, sorbitan fatty acid ester, And polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene fatty acid esters, and polyoxyethylene alkylamines.

Other examples include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, and polyethyleneimines. have.

In addition, the pigment dispersant preferably contains an acrylate-based dispersant (hereinafter, an acrylate-based dispersant) including butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA). Commercial products of the acrylate-based dispersants include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, or DISPER BYK-2150, and the acrylate-based dispersants can be used alone or in combination of two or more. Can be.

In addition to the acrylate-based dispersant, other resin-type pigment dispersants may be used. As the other resin type pigment dispersant, a known resin type pigment dispersant, in particular of polyurethane, polyacrylate, polycarboxylic acid ester, unsaturated polyamide, polycarboxylic acid, and polycarboxylic acid (partially) 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 their modified products, or free ) Oily dispersants such as amides or salts thereof formed by the reaction of polyesters having carboxyl groups with poly(lower alkyleneimines); 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 polyacrylates; Addition products of ethylene oxide/propylene oxide; And phosphate esters.

Commercially available products of the other resin type pigment dispersants include, for example, cationic resin dispersants, for example, BYK (Big) Chemicals: 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 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; Trade names of Kawaken Fine Chemicals: HINOACT T-6000, Hinoact T-7000, Hinoact T-8000; Ajinomoto's trade names: AJISPUR PB-821, AJISPUR PB-822, AJISPUR PB-823; Trade names of Kyoeisha Chemicals: FLORENE DOPA-17HF, Floren DOPA-15BHF, Floren DOPA-33, Floren DOPA-44, and the like.

In addition to the acrylate-based dispersants, other resin-type pigment dispersants may be used alone or in combination of two or more, or may be used in combination with the acrylate-based dispersants.

The pigment dispersant may be included in 5 to 60% by weight, preferably 15 to 50% by weight based on 100% by weight of the solid content of the pigment. When the pigment dispersant is included within the above range, it is possible to maintain an appropriate viscosity level for easy production of the red photosensitive resin composition, and it is preferable because the gelation process after atomization and dispersion of the pigment is easy.

(a3) dye

The dye can be used without limitation as long as it has solubility in an organic solvent. Preferably, it is preferable to use a dye which has a solubility in an organic solvent and ensures solubility in an alkali developer and reliability such as heat resistance and solvent resistance.

As the dye, an acidic dye having an acidic group such as sulfonic acid or carboxylic acid, a salt of an acidic dye and a nitrogen-containing compound, a sulfonamide body of an acidic dye, or the like and a derivative thereof can be used. In addition, azo-based, xanthene-based, and phthalocyanine Acidic dyes and derivatives thereof may also be selected. Preferably, the dye is a compound classified as a dye in a color index (published by The Society of Dyers and Colourists) or a known dye described in a dyeing note (dyeing company).

Specific examples of the dye, C.I. As a solvent dye,

C.I. Yellow dyes such as solvent yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;

C.I. Red dyes such as solvent red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179;

C.I. Orange dyes such as solvent orange 2, 7, 11, 15, 26, 41, 45, 56, and 62;

C.I. C.I. excellent in solubility in organic solvents among solvent dyes. Solvent Yellow 14, 16, 21, 56, 151, 79, 93; preferred and C.I. Solvent Yellow 21, 79; are more preferred.

In addition, C.I. As an acid dye,

CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 , 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184 Yellow dyes such as, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251 ;

CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88 , 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217 , 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349 , 382, 383, 394, 401, 412, 417, 418, 422, 426, and other red dyes;

Orange dyes such as C.I. acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

C.I. C.I. Acid Yellow 42 having excellent solubility in organic solvents in acid dyes; C.I. Acid Green 27 is more preferred.

Also as a C.I.direct dye,

CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129 , Yellow dyes such as 136, 138, 141;

CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211 Red dyes such as, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

Orange dyes such as C.I.direct orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

In addition, C.I. As a modanto dye,

Yellow dyes such as C.I. modanto yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

CI Modanto Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, Red dyes such as 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, and 95;

CI Modanto Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48 dyes;

The dyes may be used alone or in combination of two or more.

When the dye is included in the colorant, the content of the dye may be included in 0.5 to 80% by weight relative to 100% by weight of the solid content of the colorant, preferably 0.5 to 60% by weight, and more preferably 1 to 50% by weight. When the dye is included within the above content range, it is possible to prevent a problem of a decrease in reliability in which the dye is eluted by an organic solvent after pattern formation, and the sensitivity is high, which is preferable.

The content of the colorant may be included in 5 to 60% by weight, preferably 10 to 45% by weight based on the total weight of solids in the red photosensitive resin composition. When the colorant is included in the above range, it is preferable that the color density of the pixel is sufficient when forming a thin film, and the omission of the non-pixel portion does not deteriorate during development, so that residue is less likely to occur.

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

(B) alkali-soluble resin

The alkali-soluble resin is characterized in that it is produced by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group as an essential component in order to have solubility with respect to an alkali developer used in the developing treatment process when forming a pattern.

The content of the alkali-soluble resin may be included in 10 to 80% by weight, preferably 10 to 70% by weight based on the total weight of solids in the red photosensitive resin composition. When the alkali-soluble resin is included within the above range, the solubility in the developer is sufficient to facilitate pattern formation, and film development of the pixel portion of the exposed portion is prevented during development, and the omission of the non-pixel portion is improved, which is preferable. Do.

The acid value of the alkali-soluble resin is preferably 30 mg·KOH/g to 150 mg·KOH/g, and accordingly, compatibility with the dye and light stability of the red photosensitive resin composition may be improved. When the acid value of the alkali-soluble resin is less than 30 mg·KOH/g, it is difficult for the red photosensitive resin composition to secure a sufficient developing speed, and when it exceeds 150 mg·KOH/g, the adhesion to the substrate is reduced and short circuit of the pattern This is likely to occur, and compatibility with the dye may cause a problem, and the dye in the red photosensitive resin composition may precipitate or the viscosity of the red photosensitive resin composition may deteriorate and the viscosity may increase.

A hydroxyl group may be provided to secure additional developability of the alkali-soluble resin. When a hydroxyl group is added to the alkali-soluble resin, there is an effect that the development speed is improved.

It is preferable that the sum of the hydroxyl group values of the alkali-soluble resin and the photopolymerizable compound described below is 50 mg·KOH/g to 250 mg·KOH/g. When the sum of the alkali-soluble resin and the hydroxyl group of the photopolymerizable compound is less than 50 mg·KOH/g, a sufficient development rate cannot be secured, and when it exceeds 250 mg·KOH/g, the dimensional stability of the pattern formed It is easy to deteriorate, and the straightness of the pattern tends to be poor, and compatibility with the dye may be deteriorated, resulting in a problem of stability over time.

(b1) ethylenically unsaturated monomer having a carboxyl group

Examples of the ethylenically unsaturated monomer having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; And these anhydrides of dicarboxylic acids; and mono(meth)acrylates of polymers having carboxyl groups and hydroxyl groups at both ends, such as ω-carboxypolycaprolactone mono(meth)acrylate, and acrylic acid and methacrylic acid are preferred.

The alkali-soluble resin may be prepared by copolymerizing the ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group (b2). Alternatively, the alkali-soluble resin may be prepared by copolymerizing a copolymer of the ethylenically unsaturated monomer having a carboxyl group with a compound (b3) having a glycidyl group. Alternatively, the alkali-soluble resin may be prepared by copolymerizing the ethylenically unsaturated monomer having the carboxyl group, the ethylenically unsaturated monomer having the hydroxyl group, and the compound having the glycidyl group.

(b2) ethylenically unsaturated monomer having a hydroxyl group

Specific examples of the ethylenically unsaturated monomer having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 2-hydroxy- 3-phenoxypropyl (meth)acrylate, N-hydroxyethyl acrylamide, and the like, and 2-hydroxyethyl (meth)acrylate are preferred, and two or more kinds can be used in combination.

(b3) Compound having glycidyl group

Specific butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyrate, glycidyl methyl ether, ethyl glycyl of the compound having the glycidyl group Diyl ether, glycidyl isopropyl ether, t-butyl glycidyl ether, benzyl glycidyl ether, glycidyl 4-t-butyl benzoate, glycidyl stearate, aryl glycidyl ether, methacrylic acid glyc There is a cydyl ester, and butyl glycidyl ether, aryl glycidyl ether, and methacrylic acid glycidyl ester are preferred, and two or more kinds can be used in combination.

The alkali-soluble resin may be prepared by copolymerizing an unsaturated monomer (b4).

(b4) unsaturated monomer

The unsaturated monomers may be used alone or in combination of two or more, respectively, and are not limited to the following examples.

Styrene, vinyl toluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethylether, m-vinylbenzylmethylether, p-vinyl Aromatic vinyl compounds such as benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, and p-vinyl benzyl glycidyl ether;

N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide compounds such as -methylphenylmaleimide, Np-methylphenylmaleimide, No-methoxyphenylmaleimide, Nm-methoxyphenylmaleimide, and Np-methoxyphenylmaleimide;

Methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, alkyl (meth)acrylates such as sec-butyl (meth)acrylate and t-butyl (meth)acrylate; Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6]decane-8-yl (meth)acrylate, 2- Alicyclic (meth)acrylates such as dicyclopentanyloxyethyl (meth)acrylate and isobornyl (meth)acrylate;

Aryl (meth)acrylates such as phenyl (meth)acrylate and benzyl (meth)acrylate;

3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane, etc. Of unsaturated oxetane compounds.

(C) Photopolymerizable compound

The photopolymerizable compound is a compound that can be polymerized by the action of the photopolymerization initiator described below, and examples thereof include a monofunctional monomer, a bifunctional monomer, and other polyfunctional monomers.

Specific examples of the monofunctional monomer include nonylphenylcarbitolacrylate, 2-hydroxy-3-phenoxypropylacrylate, 2-ethylhexylcarbitolacrylate, 2-hydroxyethylacrylate, and N-vinylpy And rollidone. As specific examples of the bifunctional monomer, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate , Bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, and the like. Specific examples of other polyfunctional monomers include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and di And pentaerythritol hexa(meth)acrylate. Among them, a bifunctional or higher polyfunctional monomer is preferably used.

The photopolymerizable compound may be included in 5 to 50% by weight, preferably 7 to 45% by weight based on the total weight of solids in the red photosensitive resin composition. When the photopolymerizable compound is included in the above range, it is preferable because the strength and smoothness of the pixel portion tend to be good.

(D) Photopolymerization initiator

The photopolymerization initiator is characterized in that it comprises at least one member selected from the group consisting of carbazole-based and fluorene oxime-based. Thereby, reliability such as solvent resistance and adhesion of the red photosensitive resin composition according to the present invention containing a specific colorant can be improved.

It is preferable that the photopolymerization initiator includes a compound represented by Formula 1 below.

[Formula 1]

(In Formula 1, A is a CH or nitrogen atom,

R ₁ to R ₈ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a group represented by Formula 2, COR ₁₆ or NO ₂ ,

R ₁₃ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 12 carbon atoms, cycloalkenyl group having 4 to 8 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, phenyl group, or Naphthyl group,

R ₁₆ is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of an alkoxy group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms.)

[Formula 2]

(In the formula 2, R ₁₄ is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a phenyl group, or a naphthyl group,

R ₁₅ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

X is CO or a direct link,

* Is a bond with a carbon atom or a nitrogen atom.)

In addition, in the compound represented by Chemical Formula 1, A is -CH- or a nitrogen atom, and R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or at least one pair of R ₇ and R ₈ may be a group represented by Formula 3 below.

[Formula 3]

(In the formula (3), R ₉ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted phenyl group.)

The photopolymerization initiator may include, in addition to the compound represented by Chemical Formula 1, a photopolymerization initiator generally used in this field, in an amount of 5 to 40% by weight based on the total weight of the photopolymerization initiator.

Examples of the photopolymerization initiator generally used include triazine-based compounds, acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, and oxime-based compounds.

The triazine-based compounds include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloro methyl)-s-triazine, 2-(3',4'-dime Thoxy styryl)-4,6-bis(trichloro methyl)-s-triazine, 2-(4'-methoxy naphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2 -(p-methoxy phenyl)-4,6-bis(trichloro methyl)-s-triazine, 2-(p-tolyl-4,6-bis(trichloromethyl)-s-triazine, 2- Piphenyl-4,6-bis(trichloro methyl)-s-triazine, bis(trichloro betyl)-6-styryl-s-triazine, 2-(naphtho 1-yl)-4,6- Bis(trichloro methyl)-s-triazine, 2-(4-methoxy naphtho 1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-trichloro methyl ( Piperonyl)-6-triazine, 2,4-trichloro methyl (4'-methoxy styryl)-6-triazine, and the like.

Specific examples of the acetophenone-based compound, 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone , pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane And -1-one.

The benzophenone compounds include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethyl amino)benzophenone, 4,4'- And bis(diethyl amino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

Examples of the thioxanthone-based compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, and 2,4-diisopropyl thi. Oxanthone, 2-chloro thioxanthone, etc. are mentioned.

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

The oxime-based compound is 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione and 1-(o-acetyloxime)-1-[9-ethyl- And 6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone.

In addition to the exemplified above, carbazole-based compounds, diketone compounds, sulfonium borate-based compounds, diazo-based, biimidazole-based compounds, and the like can also be used as the photopolymerization initiator.

The photopolymerization initiator may be included in 0.1 to 10% by weight, more preferably 3 to 8% by weight based on the total weight of solids in the red photosensitive resin composition. When the photopolymerization initiator is included within the above range, photopolymerization occurs sufficiently during exposure in the pattern forming process, and may not cause a decrease in transmittance due to unreacted initiator remaining after photopolymerization.

(E) Solvent

If the solvent is effective for dissolving other components included in the red photosensitive resin composition, a solvent used in a typical red photosensitive resin composition can be used without particular limitation, and in particular, ethers, aromatic hydrocarbons, ketones, alcohols, esters Classes or amides are preferred.

The solvent is specifically ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoalkyl ethers such as ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, Diethylene glycol dialkyl ethers such as diethylene glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, Alkylene glycol alkyl ether acetates such as propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and methyl ethyl ketone , Ketones such as acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin, 3-ethoxypropionate ethyl, 3- And esters such as methyl methoxypropionate, and cyclic esters such as γ-butyrolactone.

The solvent is preferably an organic solvent having a boiling point of 100°C to 200°C in terms of coatability and dryness, and more preferably, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butalac Tate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like can be used.

The solvents exemplified above may be used alone or in combination of two or more, and may be included in an amount of 60 to 90% by weight, preferably 70 to 85% by weight, based on the total weight of the red photosensitive resin composition of the present invention. When the solvent is included within the above content range, the effect of improving the coatability when applied with an application device such as a roll coater, spin coater, slit and spin coater, slit coater (sometimes referred to as die coater), inkjet, etc. It is preferred because it provides.

(F) additive

The red photosensitive resin composition according to the present invention may further include additives as necessary, and for example, at least one selected from a dispersant, a wetting agent, a silane coupling agent, and an anti-agglomeration agent may be used.

As the dispersant, a commercially available surfactant can be used, and examples of the surfactant include a silicone-based surfactant, a fluorine-based surfactant, a silicone-based surfactant having a fluorine atom, and mixtures thereof. Examples of the silicone surfactant include surfactants having a siloxane bond. As commercially available products, Torreysilicon DC3PA, Torreysilicon SH7PA, Torreysilicon DC11PA, Torreysilicon SH21PA, Torreysilicon SH28PA, Torreysilicon 29SHPA, Torreysilicon SH30PA, Polyether modified silicone oil SH8400 (manufactured by Torreysilicon Co., Ltd.), KP321 , KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Silicone), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufactured by GE Toshiba Silicon Co., Ltd.), etc. Can be lifted.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain. Specifically, Prolinate (brand name) FC430, Prolinate FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megapack (brand name) F142D, Megapack F171, Megapack F172, Megapack F173, Megapack F177, Megapack F183, Megapack R30 (manufactured by Dainippon Ink Kagaku Kogyo Co., Ltd.), F-top (brand name) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Shin-Akita Kasei Co., Ltd.), Seo Pron (brand name) S381, Surfon S382, Surfon SC101, Surfon SC105 (manufactured by Asahi Glass Co., Ltd.), E5844 (manufactured by Daikin Fine Chemicals Gen.), BM-1000, BM-1100 (product Name: BMChemie).

Examples of the silicone-based surfactant having a fluorine atom include a siloxane bond and a surfactant having a fluorocarbon chain. Specifically, Megapack (trade name) R08, Megapack BL20, Megapack F475, Megapack F477, Megapack F443 (manufactured by Dainippon Ink Kagaku Kogyo Co., Ltd.) and the like can be exemplified.

Examples of the wetting agent include glycerin, diethylene glycol, and ethylene glycol, and may include one or more selected therefrom.

Examples of the silane coupling agent include aminopropyl triethoxysilane, γ-mercaptopropyl trimethoxysilane, and γ-methacryloxypropyl trimethoxysilane, and commercially available products include SH6062, SZ6030 (Toray-Dow Corning Silicon co., Ltd.), KBE903, KBM803 (Shin-Etsu silicone co., Ltd.).

Examples of the aggregation inhibitor include sodium polyacrylate.

Color filter and display

In addition, the present invention provides a color filter including a colored pattern made of a red photosensitive resin composition according to the present invention, and a display device including the color filter.

A display device that may include such a color filter may include a liquid crystal display device, an OLED, and a flexible display, but is not limited thereto, and all display devices known in this field that can be applied may be exemplified.

The color filter can be produced by applying the red photosensitive resin composition of the present invention on the substrate, photocuring and developing to form a pattern.

First, a red photosensitive resin composition is applied to a substrate and then dried by heating to remove volatile components such as a solvent to obtain a smooth coating film.

As the coating method, for example, it can be carried out by a spin coating method, a flexible coating method, a roll coating method, a slit and spin coating or a slit coating method. After application, heating and drying (pre-baking) or drying under reduced pressure is followed by heating to volatilize volatile components such as solvents. Here, the heating temperature is usually 70 to 200°C, preferably 80 to 130°C. The thickness of the coating film after heating and drying is usually about 1 to 8 µm. The coating film thus obtained is irradiated with ultraviolet light 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 is uniformly irradiated to the entire exposed portion and accurate alignment of the mask and the substrate is performed. When irradiated with ultraviolet rays, curing of a region irradiated with ultraviolet rays is achieved.

As the ultraviolet rays, g-rays (wavelength: 436 nm), h-rays, i-rays (wavelength: 365 nm), or the like can be used. The irradiation amount of ultraviolet light may be appropriately selected as necessary, and the present invention is not limited thereto. The desired pattern shape can be formed by contacting the developer after curing is completed by dissolving and developing the non-exposed portion.

The developing method may be any of a liquid addition method, a dipping method, and a spray method. Further, the substrate may be tilted at an arbitrary angle during development. The supernatant is usually an aqueous solution containing an alkaline compound and a surfactant. The alkaline compound may be any of inorganic and organic alkaline compounds. Specific examples of the inorganic alkaline compound include sodium hydroxide, potassium hydroxide, dihydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, potassium carbonate , Sodium hydrogen carbonate, potassium hydrogen carbonate, sodium borate, potassium borate, ammonia and the like. Further, specific examples of the organic alkaline compound include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, And monoisopropylamine, diisopropylamine, and ethanolamine.

These inorganic and organic alkaline compounds can be used alone or in combination of two or more. The concentration of the alkaline compound in the alkali developer is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.

The surfactant in the alkali developer may use at least one selected from the group consisting of nonionic surfactants, anionic surfactants, or cationic surfactants.

Specific examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene/oxypropylene block copolymer, sorbitan fatty acid ester, And polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene fatty acid esters, and polyoxyethylene alcohol amines.

Specific examples of the anionic surfactant include lauryl alcohol sulfate, higher alcohol sulfate ester salts such as sodium sterol or oleyl alcohol sulfate ester, alkyl sulfates such as sodium lauryl sulfate or ammonium lauryl sulfate, and dodecylbenzenesulfonic acid And alkylarylsulfonates such as sodium and sodium dodecylnaphthalenesulfonate.

Specific examples of the cationic surfactant include amine salts such as stearylamine hydrochloride and lauryl trimethylammonium chloride or quaternary ammonium salts. These surfactants may be used alone or in combination of two or more.

The concentration of the surfactant in the developer is usually 0.01 to 10% by mass, preferably 0.05 to 8% by mass, more preferably 0.1 to 5% by mass. After development, it is washed with water, and if necessary, post-baking may be performed at 150 to 230°C for 10 to 60 minutes.

Hereinafter, the present invention will be described in more detail based on examples, but the embodiments of the present invention disclosed below are merely examples, and the scope of the present invention is not limited to these embodiments. The scope of the invention is indicated in the claims, and furthermore, includes all changes within the meaning and scope equivalent to the claims of the claims. In addition, "%" and "part" showing content in the following Examples and Comparative Examples are based on mass unless otherwise specified.

Examples and Comparative Examples: Preparation of red photosensitive resin composition

Example 1

(A) C.I. 25 parts of Pigment Red 179 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as photopolymerizable compound, (D) 1 part of OXE-02 (BASF) as photopolymerization initiator, and (E) A red photosensitive resin composition according to Example 1 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Example 2

(A) C.I. 25 parts of Pigment Red 264 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as photopolymerizable compound, (D) 1 part of OXE-02 (BASF) as photopolymerization initiator, and (E) A red photosensitive resin composition according to Example 2 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Example 3

(A) C.I. Pigment Red 179 (pigment) 12.5 parts, C.I. Pigment Red 264 (pigment) 12.5 parts, pigment dispersant as BYK-2001 (BYK) 4 parts and propylene glycol monomethyl ether acetate 71 parts mixed, 30 parts of pigment dispersion with sufficient dispersion of the pigment using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as photopolymerizable compound, (D) 1 part of OXE-02 (BASF) as photopolymerization initiator, and (E) A red photosensitive resin composition according to Example 3 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Example 4

(A) C.I. 25 parts of Pigment Red 179 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as photopolymerizable compound, (D) 1 part of OXE-03 (BASF) as photopolymerization initiator, and (E) A red photosensitive resin composition according to Example 4 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Example 5

(A) C.I. 25 parts of Pigment Red 179 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as an alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as a photopolymerizable compound, (D) 1 part of SPI-03 (Samyang Co.) as a photopolymerization initiator, and (E) A red photosensitive resin composition according to Example 5 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Comparative Example 1

(A) C.I. 25 parts of Pigment Red 254 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as photopolymerizable compound, (D) 1 part of OXE-02 (BASF) as photopolymerization initiator, and (E) A red photosensitive resin composition according to Comparative Example 1 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Comparative Example 2

(A) C.I. 25 parts of Pigment Red 177 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as photopolymerizable compound, (D) 1 part of OXE-02 (BASF) as photopolymerization initiator, and (E) A red photosensitive resin composition according to Comparative Example 2 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Comparative Example 3

(A) C.I. 25 parts of Pigment Red 179 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as an alkali-soluble resin, (C) 5 parts of A9550 (Shinakamura) as a photopolymerizable compound, (D) 1 part of I-369 (ciba) as a photopolymerization initiator, and (E) A red photosensitive resin composition according to Comparative Example 3 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Comparative Example 4

(A) C.I. 25 parts of Pigment Red 179 (pigment), 4 parts of BYK-2001 (BYK) and 71 parts of propylene glycol monomethyl ether acetate as a pigment dispersant, and 30 parts of a pigment dispersion in which pigments were sufficiently dispersed using a bead mill, ( B) 10 parts of SPCY-6L (Showa Polymer Co.) as an alkali-soluble resin, (C) 5 parts of A9550 (Cinnakamura) as a photopolymerizable compound, (D) 1 part of I-907 (ciba) as a photopolymerization initiator, and (E) A red photosensitive resin composition according to Comparative Example 4 was prepared by mixing 54 parts of propylene glycol monomethyl ether acetate as a solvent.

Preparation Example: Preparation of a color filter using a red photosensitive resin composition

The red photosensitive resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 4 were coated on a bare glass substrate by spin coating, then placed on a heating plate and held at a temperature of 100° C. for 2 minutes to form a thin film. Subsequently, a test photomask having a pattern in which the transmittance is changed stepwise in the range of 1 to 100% and a line/space pattern of 1 to 100 µm is placed on the thin film, and the distance from the test photomask is 200 µm. Was investigated. At this time, the ultraviolet light source was irradiated with an illuminance of 50 mJ/cm 2 using a 1 KW high-pressure mercury lamp containing all g, h, and i rays, and no special optical filter was used. The thin film irradiated with ultraviolet rays was developed by immersing it in a KOH aqueous solution developing solution having a pH of 10.5 for 2 minutes. After the process, the baking was performed for 20 minutes on a 230°C hotplate. The film thickness of the color filters of the red photosensitive resin compositions according to Examples 1 to 5 and Comparative Examples 1 to 4 prepared accordingly was 2.5 μm.

Test Example: Evaluation of physical properties of a color filter using a red photosensitive resin composition

1. Evaluation of solvent resistance

The color filter prepared according to the above production example was immersed in a 23° C. NMP solvent for 30 minutes to compare and evaluate color changes before and after immersion. At this time, the color change is calculated by [Equation 1] below, and the values calculated by [Equation 1] below are shown in Table 1 below.

[Equation 1]

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

[Equation 1] represents the color change in the 3D colorimeter defined by L*, a*, b*, and the smaller the color change value calculated by [Equation 1], the higher the reliability of the solvent resistance. It is possible to manufacture color filters.

<Evaluation criteria>

○: Excellent solvent resistance (no pattern change, △(Eab*) less than 3.0)

△: Good solvent resistance (pattern change slightly or △(Eab*) is 3.0 or more and less than 5.0)

×: poor solvent resistance (pattern change or Δ(Eab*) of 5.0 or more)

2. Evaluation of adhesion

The color filter prepared according to the above production example was immersed in NMP solvent at room temperature, waited for 10 minutes, and then OK and NG were judged through whether or not the formed pattern was detached. 1 is a view showing a criterion for evaluating such adhesion. If the pattern remains after immersion, it is OK, and if the pattern is detached after immersion, it is determined as NG, and the results are shown in Table 1 below.

3. Spectral transmittance measurement

The spectral transmittance of the color filter prepared according to the above production example was measured using a microscopic spectrophotometer, OSP-SP2000 (Olympus). The results are shown in FIGS. 2 and 3, of which spectral transmittance in the range of 590 nm to 595 nm is shown in Table 1 below.

On the other hand, since Examples 4 to 5 and Comparative Examples 3 to 4 exhibit substantially the same spectral transmittance as Example 1 containing the same colorant, in FIGS. 2 and 3, Examples 1 to 3 and Comparative Examples 1 to 2 Only spectral transmittance is shown.

division Solvent resistance Adhesion 590~595nm
Transmittance Example 1 O OK 3-10% Example 2 O OK 4-10% Example 3 O OK 2~9% Example 4 O OK 3-10% Example 5 O OK 3-10% Comparative Example 1 O OK 70~81% Comparative Example 2 O OK 12-29% Comparative Example 3 X NG 3-10% Comparative Example 4 X NG 3-10%

Referring to Table 1, FIGS. 2 and 3, Examples 1 to 5 according to the present invention have a spectral transmittance in the range of 590 nm to 595 nm of 10% or less, and a spectral transmittance of 600 nm or more in 20% or more, Comparative Example 1 And 2, it can be confirmed that the spectral transmittance was shifted to the right as a whole. That is, in the case of a color filter manufactured by using the red photosensitive resin composition according to the present invention, the spectral transmittance is concentrated in a region of the red series, thereby exhibiting better RED spectral color purity.

In addition, in Examples 1 to 5 using a carbazole-based or fluorene oxime-based compound as an initiator, while showing excellent effects in both solvent resistance and adhesion, Comparative Example 3 using an initiator other than the carbazole-based and fluorene oxime-based compounds And in the case of 4, it can be seen that both solvent resistance and adhesion are poor.

Therefore, when a color filter is manufactured using the red photosensitive resin composition according to the present invention, the spectral peak transmittance in the range of 590 nm to 595 nm is 10% or less, and the spectral transmittance of 600 nm or more can be 20% or more, and accordingly While the color purity of the RED spectrum is improved, a color filter excellent in solvent resistance and adhesion can be obtained at the same time.

Claims (7)

A red photosensitive resin composition comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent,
The colorant (A) includes at least one selected from the group consisting of CI Pigment Red 179 and CI Pigment Red 264,
The (D) photopolymerization initiator includes at least one selected from the group consisting of carbazole-based and fluorene oxime-based,
The red photosensitive resin composition of the thin film made of the red photosensitive resin composition has a spectral transmittance of 10% or less in a range of 590 nm to 595 nm.
The method according to claim 1,
The red photosensitive resin composition, characterized in that the thin film made of the red photosensitive resin composition has a spectral transmittance of 20% or more of 600 nm or more.
The method according to claim 1,
The (D) photopolymerization initiator is a red photosensitive resin composition, characterized in that it comprises a compound represented by the formula (1).
[Formula 1]

(In Formula 1, A is a CH or nitrogen atom,
R ₁ to R ₈ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a group represented by Formula 2, COR ₁₆ or NO ₂ ,
R ₁₃ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 12 carbon atoms, cycloalkenyl group having 4 to 8 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, phenyl group, or Naphthyl group,
R ₁₆ is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of an alkoxy group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms.)
[Formula 2]

(In the formula 2, R ₁₄ is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a phenyl group, or a naphthyl group,
R ₁₅ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
X is CO or a direct link,
* Is a bond with a carbon atom or a nitrogen atom.)
The method according to claim 3,
In Formula 1, at least one pair of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ is Red photosensitive resin composition characterized in that the group represented by:
[Formula 3]

(In the formula (3), R ₉ to R ₁₂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted phenyl group.)
The method according to claim 1,
The total weight of solids in the red photosensitive resin composition,
(A) 5 to 60% by weight of the coloring agent,
10 to 80% by weight of the (B) alkali-soluble resin,
(C) 5 to 50% by weight of the photopolymerizable compound, and
The (D) photopolymerization initiator contains 0.1 to 10% by weight,
The (E) solvent is a red photosensitive resin composition, characterized in that contained in 60 to 90% by weight relative to the total weight of the red photosensitive resin composition.
A color filter comprising a colored pattern made of the red photosensitive resin composition of claim 1.
A display device comprising the color filter of claim 6.

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