KR102355812B1 - Colored Photosensitive Resin Composition, Color Filter and Display Device - Google Patents

Abstract

Having a ^greater-the invention a coloring agent, a colored photosensitive resin composition comprising an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, wherein the colorant comprises a pigment and a dye, the dye is -COOM or -COO in the molecule a santhene compound, wherein the alkali-soluble resin includes a dicyclopentanyl group-containing repeating unit, the photopolymerization initiator includes an oxime ester compound in which a methyl radical is generated by irradiation with light, and the solvent has a hydroxyl group in the molecule Provided are a colored photosensitive resin composition containing an organic solvent, a color filter and an image display device manufactured using the same. The colored photosensitive resin composition according to the present invention has excellent transmittance, no residue or pattern tearing during the manufacture of color filters, does not decrease transmittance of adjacent pixel portions, and has excellent storage stability.

Description

Colored Photosensitive Resin Composition, Color Filter and Display Device

The present invention relates to a colored photosensitive resin composition, a color filter, and an image display device, and more particularly, has excellent transmittance, no residue or pattern tearing during color filter manufacturing, no decrease in transmittance of adjacent pixel portions, and excellent storage stability It relates to a colored photosensitive resin composition, a color filter formed using the same, and an image display device having the color filter.

A color filter is widely used in imaging devices, liquid crystal display devices, and the like, and its application range is rapidly expanding. A color filter is usually formed by applying a colored photosensitive resin composition containing a colorant corresponding to each color of red, green, and blue uniformly by spin coating on a substrate on which a black matrix is patterned, followed by heating and drying (hereinafter referred to as preliminary firing). It is manufactured by forming pixels of each color by repeating the operation of exposing, developing, and further heat-hardening (hereinafter, sometimes referred to as post-firing) for each color if necessary.

In recent years, the market demand for a high-quality display with high color reproducibility is increasing. Accordingly, the content of the coloring material of the colored photosensitive resin composition used for manufacturing the color filter is continuously increasing. In the case of a colored photosensitive resin composition for generating blue pixels, a blue pigment as a main color material and a violet pigment as an auxiliary color material were mainly used. However, as the color reproducibility increases, the transmittance decreases. Some are used instead [refer to Korean Patent Publication No. 10-2016-0118011].

However, when the dye is used as an auxiliary pigment, the degree of curing is insufficient, and the pattern formed during the development process with an alkali developer is peeled off. During high temperature curing, the dye is diffused to the adjacent green or red pixel part, and the transmittance of the green or red pixel part is lowered. It is necessary to improve the color transfer phenomenon, etc.

In addition, there is a demand for development of a colored photosensitive resin composition having no residue or pattern tearing during the manufacture of a color filter and excellent storage stability.

Korean Patent Publication No. 10-2016-0118011

One object of the present invention is to provide a colored photosensitive resin composition having excellent transmittance, no residue or pattern tearing during the manufacture of a color filter, no decrease in transmittance of adjacent pixel portions, and excellent storage stability.

Another object of the present invention is to provide a color filter formed using the colored photosensitive resin composition.

Another object of the present invention is to provide an image display device including the color filter.

On the other hand, the present invention provides a colored photosensitive resin composition containing a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, wherein the colorant comprises a pigment and a dye, the dye is -COOM or -COO in the molecule ^- includes a xanthene compound having a group, wherein M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N(R ¹² ) ₄ , four R ¹² may be the same or different, and R ¹² is a hydrogen atom, Representing a saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, the alkali-soluble resin includes a repeating unit represented by the following Chemical Formulas 1 to 2, and the photopolymerization initiator generates a methyl radical by light irradiation It provides a colored photosensitive resin composition comprising an oxime ester compound, wherein the solvent includes an organic solvent having a hydroxyl group in the molecule.

[Formula 1]

[Formula 2]

In the above formula,

R ^a and R ^b are each independently a hydrogen atom or methyl,

R ^c is an alkyl group having 1 to 20 carbon atoms,

n and m are each independently an integer from 1 to 500.

On the other hand, the present invention provides a color filter formed using the colored photosensitive resin composition.

On the other hand, the present invention provides an image display device, characterized in that the color filter is provided.

Colored photosensitive resin composition according to the present invention is -COOM or -COO within the ^molecule comprising an alkali-soluble resin containing a repeating unit comprising group dicyclopentanyl, comprises a xanthene dye having a group, the methyl radical by light irradiation Contains the generated oxime ester photopolymerization initiator, contains an organic solvent having a hydroxyl group in the molecule, and has excellent transmittance. There is no residue or pattern tearing during color filter manufacturing, and the transmittance of adjacent pixels does not decrease, and storage stability is excellent.

Hereinafter, the present invention will be described in more detail.

One embodiment of the present invention includes a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D) and a solvent (E), wherein the colorant (A) is a pigment and a dye and wherein the dye is -COOM or -COO in the ^{molecule-size} comprises Santen compound, the alkali-soluble resin (B) contains a repeating unit having a group comprises a dicyclopentanyl group, and the photopolymerization initiator (D) is an optical It includes an oxime ester compound in which a methyl radical is generated by irradiation, and the solvent (E) relates to a colored photosensitive resin composition comprising an organic solvent having a hydroxyl group in the molecule.

Colorant (A)

In one embodiment of the present invention, the colorant (A) comprises a pigment and a dye, the dye is -COOM or -COO within the ^molecule include compounds having a xanthine. In this case, M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N(R ¹² ) ₄ , four R ¹² may be the same or different, and R ¹² is a hydrogen atom, a saturated hydrocarbon having 1 to 20 carbon atoms. group or an aralkyl group having 7 to 10 carbon atoms.

Pigment (a1)

In one embodiment of the present invention, the pigment may be an organic pigment or inorganic pigment generally used in the art. As the pigment, various pigments used in printing inks, inkjet inks, etc. may be used, and specifically, water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, ferri Rennes pigment, perinone pigment, dioxazine pigment, anthraquinone pigment, dianthraquinonyl pigment, anthrapyrimidine pigment, anthanthrone pigment, indanthrone pigment, pravanthrone pigment, pyranthrone A pigment, a diketopyrroropyrrole pigment, etc. are mentioned. Examples of the inorganic pigment include metal compounds such as metal oxides and metal complex salts, or carbon black, and specifically, oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony. Or a composite metal oxide etc. are mentioned. Red and blue pigments are preferable, and in particular, the organic and inorganic pigments include C.I. Pigment Red, C.I. Pigment Blue, C.I. Pigment violet is preferable, but it is not necessarily limited thereto, and these may be used alone or in combination of two or more.

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 215, 216, 224, 242, 254, 255, 264 and 269

C.I. Pigment Blue 15 (15:3, 15:4, 15:6, etc.), 16, 21, 28, 60, 64 and 76

C.I. Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38

In one embodiment of the present invention, said pigment is in particular C.I. Pigment Blue 15:6, C.I. Pigment Red 254 or a mixture thereof.

As the pigment, it is preferable to use a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed. Examples of the method for uniformly dispersing the particle size of the pigment include a method of dispersing and dispersing the pigment dispersant (a2). According to the method, a pigment dispersion in a state in which the pigment is uniformly dispersed in a solution can be obtained. have.

Pigment dispersant (a2)

The pigment dispersant (a2) is added to deagglomerate and maintain stability of the pigment, and those generally used in the art may be used without limitation. Commercially available dispersants include LPN-6919, Disperbyk-101, 103, 107, 108, 110, 111, 112, 116, 130, 140, 142, 154, 161, 162, 163, 164, 165, 166 by BYK, 167, 168, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163, 2164 Lubrizol's SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 56000, 76500, etc.

These may be used alone or in mixture of two or more, preferably, BYK's LPN-6919, BYK's Disperbyk-2000, 2001, which is a dispersing agent having an acidic functional group, or Lubrizol's SOLSPERSE-3000, 21000, 26000, 36600 , 41000, and the like, but are not limited thereto.

The content of the pigment dispersant (a2) is 5 to 60 parts by weight, preferably 15 to 50 parts by weight, based on 100 parts by weight of the pigment (a1). If the content of the pigment dispersant (a2) exceeds 60 parts by weight, the viscosity may increase, and if it is less than 5 parts by weight, it may be difficult to atomize the pigment or may cause problems such as gelation after dispersion.

dye (a3)

In one embodiment of the present invention, the dye is -COOM or -COO within the ^molecule include compounds having a xanthine. In this case, M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N(R ¹² ) ₄ , four R ¹² may be the same or different, and R ¹² is a hydrogen atom, a saturated hydrocarbon having 1 to 20 carbon atoms. group or an aralkyl group having 7 to 10 carbon atoms.

-COOM or -COO within the ^{molecule-xanthine} compounds having a group can improve the transmission and reliability of the colored photosensitive resin composition, it is possible to suppress the phenomenon dichloride at high temperature bake.

Specifically, -COOM or -COO within the ^{molecule-xanthine} compounds having a xanthine compound may be represented by the following formula (4).

[Formula 4]

In the above formula,

R ¹ to R ⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and included in the saturated hydrocarbon group -CH ₂ - to be formed may be substituted with -O-, -CO- or -NR ^{11 -, R 1} and R ² may be bonded together to form a ring containing a nitrogen atom, R ³ and R ⁴ may be bonded together to form a ring containing a nitrogen atom,

R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms,

However, the compound represented by Formula 4 satisfies at least one of the requirements of (i) to (vi),

(i) R ¹ is a saturated hydrocarbon group having -COOM and having 1 to 20 carbon atoms ^{, at least one of R 2} to R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and in one molecule There is 1 -COOM included,

(ii) R ¹ and R ³ are an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM,

(iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM,

(iv) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM,

(v) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R ² is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM,

(vi) R ¹ and R ² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, ^{and at least one of R 3} and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM ego,

In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N(R ¹² ) ₄ , four R ¹² may be the same or different,

R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ¹ to R ⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

The art as the aromatic hydrocarbon group optionally having substituents, halogen ^{atoms, -R 8, -OH, -OR 8} , -SO 3 H, -SO 3 - Z +, -COOM, -CO 2 R 8, -SR 8, - _{^{SO 2 R 8, -SO 3 R}} 8 or -SO there may be mentioned ₂ NR ⁹ R ^10, the substituent thereof is preferably a hydrogen atom and a substituted aromatic hydrocarbon groups are included. Among these, as the ^{_{substituent, -SO 3 H, -SO 3 -}} Z +, -COOM and -SO ₂ NR ⁹ R ¹⁰ are preferred, and -SO ₃ ^- Z ^+, -COOM and -SO ₂ NR ⁹ R ¹⁰ is more preferably. -SO ₃ in this case ^- as Z ^+, a -SO ₃ N (R ¹¹⁾ ₄ are preferred. The aromatic hydrocarbon group WHEREIN: When -COOM is contained as a substituent, it is preferable that -COOM is couple|bonded with the meta position or para position with respect to a bond. When R ¹ to R ⁴ are these groups, in the colored photosensitive resin composition of the present invention containing the xanthene compound represented by the formula (4), it is possible to form a color filter with little foreign matter and excellent heat resistance.

R ⁸ represents a saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.

R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH ₂ - contained in the saturated hydrocarbon group is -O-, -CO-, - It may be substituted with NH- or -NR ^{8 -, and R 9} and R ¹⁰ may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ¹ to R ⁴ and R ⁸ to R ¹² include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, linear alkyl groups such as a nonyl group, a decyl group, a dodecyl group, a hexadecyl group, and an icosyl group; branched alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group and 2-ethylhexyl group; A C3-C20 alicyclic saturated hydrocarbon group, such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group, is mentioned. As for carbon number of the said saturated hydrocarbon group, it is more preferable that it is 1-10.

Hydrogen atoms contained art groups saturated hydrocarbon in R ¹ ~ R ⁴ are, for example, may be -COOM, optionally substituted aromatic hydrocarbon group or a halogen atom in the 6 to 10 carbon atoms as the substituent. Further, ^{in the saturated hydrocarbon group represented by R 1} to R ⁴ , it is preferable that a hydrogen atom bonded to a terminal carbon atom (primary carbon atom) is substituted with a substituent. R may, and substituting the hydrogen atoms of the ¹ ~ R ⁴ saturated hydrocarbon groups as good an aromatic hydrocarbon group of 6 to 10 carbon atoms, R s ¹ ~ R ⁴ having 6 to 10 aromatic hydrocarbon group, the same group a group exemplified as the in can

The hydrogen atom contained in the said saturated hydrocarbon group in R<^9> and R<^10> may be substituted with the hydroxyl group or a halogen atom as a substituent, for example.

Examples of the ring formed by bonding R ¹ and R ² together and the ring formed by bonding R ³ and R ^{4 together include the following.} * indicates a bond.

-OR ^{8 is} , for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group and an icosyloxy group. An alkyloxy group etc. are mentioned.

As -CO ₂ R ⁸ , for example, an alkyloxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group and an icosyloxycarbonyl group, etc. can be heard

Examples of -SR ⁸ include alkylsulfanyl groups such as a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.

Examples of -SO ₂ R ^8, for example, there may be mentioned an alkylsulfonyl group such as a methyl sulfonyl group, ethyl sulfonyl, butyl sulfonyl group, hexyl sulfonyl group, sulfonyl group and decyl Ikoma room sulfonyl group.

As -SO ₃ R ⁸ , for example, an alkyloxysulfonyl group such as a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group and an icosyloxysulfonyl group A phonyl group etc. are mentioned.

As -SO ₂ NR ⁹ R ¹⁰ , for example, a sulfamoyl group;

N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulf Pamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-(1,1-dimethylpropyl)sulfamoyl group, N-(1, 2-dimethylpropyl)sulfamoyl group, N-(2,2-dimethylpropyl)sulfamoyl group, N-(1-methylbutyl)sulfamoyl group, N-(2-methylbutyl)sulfamoyl group, N-( 3-methylbutyl)sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-(1,3-dimethylbutyl)sulfamoyl group, N-(3,3-dimethylbutyl)sulfamo group Diyl, N-heptylsulfamoyl group, N-(1-methylhexyl)sulfamoyl group, N-(1,4-dimethylpentyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl) N-1 substituted sulfamoyl groups such as sulfamoyl group, N-(1,5-dimethylhexyl)sulfamoyl group and N-(1,1,2,2-tetramethylbutyl)sulfamoyl group;

N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N such as N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, N,N-heptylmethylsulfamoyl group, An N-2 substituted sulfamoyl group etc. are mentioned.

As a C1-C6 alkyl group in R<^6> and R<^7> , a C1-C6 thing is mentioned among the alkyl groups mentioned above. Especially, as R<^6> , R<^7> , a hydrogen atom is preferable.

Examples of the aralkyl group having 7 to 10 carbon atoms for R ¹¹ to R ¹² include a benzyl group, a phenylethyl group, and a phenylbutyl group.

Z ⁺ is ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ¹¹ ) ₄ .

Examples of the N ⁺ (R ¹¹⁾ _4, of the four R ^11, preferably at least two saturated hydrocarbon group having a carbon number of 5-20. Moreover, 20-80 are preferable and, as for total carbon number of four R<^{11>, 20-60 are more preferable.}

However, the xanthene compound represented by Formula 4 satisfies at least one of the requirements of (i) to (vi), and at least one of the requirements of (i), (ii), (iv), and (v). It is desirable to meet the dog.

(i) R ¹ is -COOM, a saturated hydrocarbon group having 1 to 20 carbon atoms ^{, at least one of R 2} to R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and contained in one molecule There is one -COOM.

(ii) R ¹ and R ³ are an aromatic hydrocarbon group having -COOM and having 6 to 10 carbon atoms.

(iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM.

(iv) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM.

(v) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ² is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM.

(vi) R ¹ and R ² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, ^{and at least one of R 3} and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM to be.

In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N(R ¹² ) ₄ , and four R ¹² may be the same or different.

R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

It is especially preferable that M is a hydrogen atom.

R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

The xanthene compound represented by Formula 4 is included in an amount of 0.1 to 20% by weight, preferably 0.5 to 10% by weight, more preferably 0.5 to 5% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition. can When the xanthene compound represented by Formula 4 is included in an amount of less than 0.1% by weight, transmittance may be deteriorated, and when included in an amount of more than 20% by weight, reliability may deteriorate.

The colorant (A) may be included in an amount of 5 to 60% by weight, preferably 10 to 45% by weight, based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the content of the colorant (A) is within the above range, the color concentration of the pixel is sufficient when forming the thin film, and the omission property of the non-pixel portion is not reduced during development, so that no residue is generated.

In this invention, solid content in the coloring photosensitive resin composition means the sum total of the component from which the solvent was removed.

Alkali-soluble resin (B)

In one embodiment of the present invention, the alkali-soluble resin (B) usually has reactivity and alkali solubility under the action of light or heat, and acts as a dispersion medium for the coloring material.

The alkali-soluble resin (B) includes a repeating unit represented by the following Chemical Formulas 1 to 2.

[Formula 1]

[Formula 2]

In the above formula,

R ^a and R ^b are each independently a hydrogen atom or methyl,

R ^c is an alkyl group having 1 to 20 carbon atoms,

n and m are each independently an integer from 1 to 500.

As used herein, an alkyl group having 1 to 20 carbon atoms means a straight-chain or branched hydrocarbon having 1 to 20 carbon atoms, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i- Butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, nonadecyl, eicosanil, and the like, but are not limited thereto.

The repeating unit represented by Formula 1 may be introduced using dicyclopentanyl (meth)acrylate as a monomer.

The repeating unit represented by Formula 2 _{may be introduced using C 1} -C ₂₀ alkyl (meth)acrylate.

The alkali-soluble resin may further include a repeating unit represented by the following formula (3).

[Formula 3]

In the above formula,

R ^d and R ^f are each independently a hydrogen atom or methyl,

R ^e is a residue comprising a carboxylic acid derived from an acid anhydride,

q is an integer from 1 to 500;

Acid anhydride as used herein is succinic anhydride, methylsuccinic anhydride, (2-dodeken-1-yl) succinic anhydride ((2-dodecen-1-yl) succinic anhydride), phenyl Succinic anhydride, phthalic anhydride, maleic anhydride, citraconic anhydride, glutaric anhydride, 3,3-dimethylglutaric anhydride ( 3,3-dimethylglutaric anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, trimellitic anhydride, hexahydrophthalic anhydride, carbic anhydride, and the like.

The repeating unit represented by Formula 3 serves to impart photocurability and acid value to the alkali-soluble resin (B). The repeating unit represented by the formula (3) uses glycidyl (meth) acrylate as a monomer to introduce the glycidyl (meth) acrylate-derived repeating unit into the main chain of the alkali-soluble resin (B), It can be formed by reacting the glycidyl group of the repeating unit derived from glycidyl (meth)acrylate with (meth)acrylic acid, and then reacting the hydroxy group generated therefrom with an acid anhydride.

Through the repeating unit represented by the formula (3), it is possible to provide an acid value without introducing a carboxylic acid directly into the main chain of the alkali-soluble resin, thereby securing developability.

Since the alkali-soluble resin includes the repeating unit represented by Chemical Formula 3, it can exhibit a glass transition temperature of less than 0 ° C., and has excellent transparency to increase luminance, and at the same time improve the coating ability when applied with a slit coater to improve luminance It is possible to manufacture a color filter with excellent quality by suppressing non-uniformity and uncoating phenomenon.

The alkali-soluble resin (B) may be a block copolymer in which the repeating units represented by Chemical Formulas 1 to 3 are constantly repeated, or a random copolymer in which they are randomly repeated.

The alkali-soluble resin contains 1-90 mol% of the repeating unit represented by Formula 1, 1-90 mol% of the repeating unit represented by Formula 2, with respect to 100 mol% of the total repeating units constituting the alkali-soluble resin, and The repeating unit represented by Formula 3 may be included in an amount of 1 to 90 mol%.

When each of the repeating units represented by Formulas 1 to 3 is included within the mol% range, an alkali-soluble resin having good developability, solubility, and balance with a colorant can be obtained.

In addition, the alkali-soluble resin may further include a repeating unit derived from a monomer containing an unsaturated double bond.

The type of the monomer containing the unsaturated double bond is not particularly limited, for example, styrene, vinyltoluene, α-methylstyrene, 4-methylstyrene, p-chlorostyrene, o-methoxystyrene, m- Methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethylether, p-vinylbenzylmethylether, o-vinylbenzylglycidylether, m-vinylbenzylglycidylether and p -Aromatic vinyl compounds, such as vinylbenzyl 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;

alicyclic (meth)acrylates such as cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-dicyclopentanyloxyethyl (meth)acrylate and isobornyl (meth)acrylate; and

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

The monomers including the unsaturated double bond may be used alone or in combination of two or more.

The content of the monomer including the unsaturated double bond is not particularly limited, but is preferably contained in an amount of 5 to 50 mol% based on 100 mol% of the total repeating units constituting the alkali-soluble resin.

The method for preparing the copolymer is not particularly limited, and a conventionally known polymerization method may be used. Among the known polymerization methods, a solution polymerization method is preferable. In addition, the polymerization temperature or polymerization time varies depending on the type or ratio of the introduced monomer, the molecular weight and acid value of the desired alkali-soluble resin, for example, polymerization can be carried out at 60 to 130 ° C. for 1 to 10 hours.

In the case of using a solvent for the polymerization, a solvent used for a general radical polymerization reaction may be used, and specifically, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone , methyl isobutyl ketone, cyclohexanone, ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, methanol, ethanol, propanol, n-butanol, ethylene glycol monomethyl ether, propylene glycol monomethyl Ether, toluene, xylene, ethylbenzene, chloroform, dimethyl sulfoxide and the like can be used. These solvents can be used individually or in combination of 2 or more types.

As the polymerization initiator used during the polymerization, a polymerization initiator commonly used may be added, and is not particularly limited. Specifically, diisopropylbenzene hydroperoxide, di-t-butyl peroxide, benzoyl peroxide, t-butylperoxyisopropyl carbonate, t-amylperoxy-2-ethylhexanoate, t-butyl organic peroxides such as peroxy-2-ethylhexanoate; 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl 2,2'-azobis(2-methylpropionate), etc. nitrogen compounds. These can be used individually or in combination of 2 or more types.

During the polymerization, a chain transfer agent may be used to control the molecular weight or molecular weight distribution of the copolymer. Examples of the chain transfer agent include mercapto compounds such as n-dodecanthiol, mercaptoacetic acid, and methyl mercaptoacetate; α-methylstyrene dimer or the like can be used.

It is preferable that the acid value of the said alkali-soluble resin (B) is 30-150 mgKOH/g. When the acid value of the alkali-soluble resin is less than 30 mgKOH / g, it is difficult for the colored photosensitive resin composition to secure a sufficient development speed, and when it exceeds 150 mgKOH / g, the adhesion with the substrate is reduced, and a short circuit of the pattern is easy to occur, Due to poor compatibility with the dye, the dye may be precipitated, and the storage stability of the colored photosensitive resin composition may be lowered, and thus a viscosity may be increased.

In addition, the polystyrene reduced weight average molecular weight (hereinafter simply referred to as 'weight average molecular weight') measured by gel permeation chromatography (GPC; using tetrahydrofuran as the elution solvent) is 3,000 to 100,000, preferably 5,000 to 50,000 Alkali-soluble resins are preferred. When the molecular weight is in the above range, the hardness of the coating film is improved, the film remaining rate is high, the solubility of the non-exposed part in the developer is excellent, and the resolution tends to be improved, which is preferable.

It is preferable that it is 1.5-6.0, and, as for the molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of alkali-soluble resin (B), it is more preferable that it is 1.8-4.0. A molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of 1.5 to 6.0 is preferable because developability is excellent.

The alkali-soluble resin (B) may be included in an amount of 10 to 80% by weight, preferably 10 to 70% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the alkali-soluble resin (B) is included in the above range, the solubility in the developer is sufficient, so that the pattern formation is easy. It is preferable because

photopolymerization compound (C)

In one embodiment of the present invention, the photopolymerizable compound (C) is a compound that can be polymerized by the action of the following photopolymerization initiator (D), and a monofunctional monomer, a difunctional monomer or other polyfunctional monomer may be used, Preferably, a bifunctional or more polyfunctional monomer may be used.

Specific examples of the monofunctional monomer include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate or N-vinyl p Rollidone, and the like, but is not limited thereto.

Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di (meth) acrylate. , bis(acryloyloxyethyl)ether of bisphenol A, or 3-methylpentanediol di(meth)acrylate, but is not limited thereto.

Specific examples of the other polyfunctional monomer include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, penta Erythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa ( Meth) acrylate or dipentaerythritol hexa (meth) acrylate, but is not limited thereto.

The photopolymerizable compound (C) may be included in an amount of 5 to 45% by weight, particularly 7 to 45% by weight, based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the photopolymerizable compound (C) is included in the above range, the intensity or smoothness of the pixel portion may be improved.

light curing initiator (D)

In one embodiment of the present invention, the photopolymerization initiator generates a radical capable of initiating polymerization of the photopolymerizable compound (C) by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray, etc. is a compound.

The photopolymerization initiator includes an oxime ester compound (d1) in which a methyl radical is generated by irradiation with light.

As the oxime ester compound (d1) in which a methyl radical is generated by irradiation with light, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone 1-(O-acetyl) oxime), etc., and commercially available products include BASF's Igacure OXE 02 and Igacure OXE 03. Since the absorbance of each photoinitiator varies, it is preferable to use a mixture of two or more types.

The oxime ester compound (d1) in which a methyl radical is generated by the light irradiation may include 10 to 100 wt%, preferably 20 to 100 wt%, based on 100 wt% of the total photopolymerization initiator. When the oxime ester compound (d1) in which methyl radicals are generated by the light irradiation is included in an amount of less than 10% by weight, the decrease in sensitivity due to the dye cannot be overcome, and a short circuit of the pattern tends to occur during the developing process.

Moreover, within the range which does not impair the effect of this invention, you may further use together photoinitiator (d2) other than the oxime ester compound (d1) which generate|occur|produces a methyl radical by the said light irradiation. Specifically, it is preferable to use at least one compound selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, a triazine-based compound, a biimidazole-based compound, and a thioxanthone-based compound.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 2-hydroxy-1-[4-(2-hydroxyl) oxyethoxy)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, etc. are mentioned.

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

Specific 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-triazine , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl )-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine etc. are mentioned.

Specific examples of the biimidazole-based 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)biimi Dazole, 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 a biimidazole compound in which the phenyl group at the 4,4',5,5' position is substituted with a carboalkoxy group; have. Among them, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4' ,5,5'-tetraphenylbiimidazole and 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole are preferably used

Examples of the thioxanthone-based compound include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like. There is this.

In addition, the photopolymerization initiator (D) may be used in combination with a photopolymerization initiator auxiliary (d3) in order to improve the sensitivity of the colored photosensitive resin composition of the present invention. The colored photosensitive resin composition according to an embodiment of the present invention contains the photopolymerization initiation auxiliary (d3), thereby further increasing the sensitivity and improving productivity.

The photopolymerization initiation adjuvant (d3) may be, for example, at least one compound selected from the group consisting of an amine compound, a carboxylic acid compound, and a polyfunctional thiol compound.

Examples of the amine compound include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine; 4-dimethylaminobenzoic acid methyl, 4-dimethylaminobenzoic acid ethyl, 4-dimethylaminobenzoic acid isoamyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethylaminoethyl, N,N-dimethylparatoluidine, 4, Aromatic amine compounds such as 4'-bis(dimethylamino)benzophenone (common name: Michler's ketone) and 4,4'-bis(diethylamino)benzophenone can be used, and it is particularly preferable to use an aromatic amine compound. do.

The carboxylic acid compound is preferably aromatic heteroacetic acid, specifically phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, and dimethoxyphenyl. Thioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc. are mentioned.

Examples of the polyfunctional thiol compound include tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, trimethylolpropane tris-3-mercaptopropionate), pentaerythritol tetrakis-3- mercaptopropionate), dipentaerythritol hexa-3-mercaptopropionate), and the like.

The photoinitiator (D) may be included in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the total amount of the alkali-soluble resin (B) and the photopolymerizable compound (C). When the photoinitiator (D) is included in the above range, it is preferable because the colored photosensitive resin composition of the present invention is highly sensitive and the exposure time is shortened, so that productivity is improved and high resolution can be maintained. In addition, the strength and smoothness of the surface of the pixel portion formed by using the composition of the above-described conditions may be improved.

In addition, when the photopolymerization initiation adjuvant (d3) is further used, the photopolymerization initiation adjuvant (d3) is 0.1 to 40 parts by weight based on 100 parts by weight of the total amount of the alkali-soluble resin (B) and the photopolymerizable compound (C) , Preferably it may be included in an amount of 1 to 30 parts by weight. When the photopolymerization initiation adjuvant (d3) is included in the above range, the sensitivity of the colored photosensitive resin composition may be increased, and productivity of a color filter formed using the composition may be improved.

Solvent (E)

In one embodiment of the present invention, the solvent (E) includes an organic solvent having a hydroxyl group in the molecule.

Examples of the organic solvent having a hydroxyl group in the molecule include diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone, dipropylene glycol methyl ether, butyl cellosolve, 3-methoxy-1-butanol, and propylene. There are glycol methyl ether, ethyl lactate, etc., and 4-hydroxy-4-methyl-2-pentanone, propylene glycol methyl ether, and ethyl lactate, which have excellent storage stability of the colored photosensitive resin composition, are preferable, and are less prone to staining. -Hydroxy-4-methyl-2-pentanone is more preferable.

The organic solvent having a hydroxyl group in the molecule may be used alone or in combination of two or more.

In one embodiment of the present invention, the solvent may further include propylene glycol monomethyl ether acetate.

When the organic solvent having a hydroxyl group in the molecule is used in combination with propylene glycol monomethyl ether acetate, it is possible to suppress the generation of foreign substances and precipitation of dyes due to excellent storage stability, and has an appropriate viscosity due to excellent dispersibility. Contrast ratio of the formed color filter may be excellent.

The mixing ratio of the propylene glycol monomethyl ether acetate and the organic solvent having a hydroxyl group in the molecule may be 95:5 to 60:40 by weight. When the mixing ratio of the propylene glycol monomethyl ether acetate and the organic solvent having a hydroxyl group in the molecule is within the above range, the storage stability and dispersibility of the colored photosensitive resin composition are excellent.

The solvent (E) is effective in dissolving other components included in the colored photosensitive resin composition in addition to the organic solvent and propylene glycol monomethyl ether acetate having a hydroxyl group in the molecule. A solvent used in a conventional colored photosensitive resin composition is further mixed. so it can be used These can be used individually or in mixture of 2 or more types.

The solvent (E) may be included in an amount of 60 to 90% by weight, preferably 70 to 85% by weight based on 100% by weight of the total colored photosensitive resin composition. When the solvent (E) is included in the above range, the applicability will be good when applied with an application 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 an inkjet. can

Additive (F)

The colored photosensitive resin composition according to an embodiment of the present invention may contain antioxidants, fillers, other polymer compounds, curing agents, adhesion promoters, ultraviolet absorbers, and anti-aggregation agents according to the needs of those skilled in the art in the range that does not impair the purpose of the present invention in addition to the above components. It is also possible to use together additives (F), such as

The antioxidant may include one or more phenolic antioxidants and one or more phosphorus antioxidants, and the phenolic antioxidant is preferably a hindered phenolic antioxidant.

Commercially available phenolic antioxidants include ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50F, ADK STAB AO-60, ADK STAB AO-80, etc. from Adeka, and commercially available phosphorus antioxidants Adeka's ADK STAB 1178, ADK STAB TPP, ADK STAB 1500, ADK STAB 135A, ADK STAB 3010, and the like.

The antioxidant may be included in an amount of 1 to 100 parts by weight, preferably 2 to 50 parts by weight, based on 100 parts by weight of the photopolymerization initiator (D) based on the solid content. When the antioxidant is included in the above range, it can be expected to improve the transmittance of the colored layer without reducing the sensitivity of the colored photosensitive resin composition.

Specifically, the filler may be glass, silica, alumina, or the like, but is not limited thereto.

Specific examples of the other high molecular compounds include curable resins such as epoxy resins and maleimide resins, and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane. However, the present invention is not limited thereto.

The curing agent is used for deep curing and increasing mechanical strength, and specifically, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, etc. may be used, but the present invention is not limited thereto. Specifically, the epoxy compound is a bisphenol A-based epoxy resin, a hydrogenated bisphenol A-based epoxy resin, a bisphenol F-based epoxy resin, a hydrogenated bisphenol F-based epoxy resin, a novolak-type epoxy resin, other aromatic epoxy resins, alicyclic epoxy resins, Glycidyl ester-based resins, glycidylamine-based resins, or brominated derivatives of these epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof, butadiene (co)polymer epoxide, isoprene (co) ) Polymer epoxide, glycidyl (meth) acrylate (co) polymer, triglycidyl isocyanurate, etc. may be used, but is not limited thereto. Specifically, the oxetane compound may include carbonate bisoxetane, xylenebisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylic acid bisoxetane, and the like, but is not limited thereto. .

The curing agent may be used in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound together with the curing agent. Specifically, as the curing auxiliary compound, polyhydric carboxylic acids, polyhydric carboxylic acid anhydrides, acid generators, and the like may be used. As the polyhydric carboxylic acid anhydrides, commercially available epoxy resin curing agents may be used. As the commercially available epoxy resin curing agent, for example, ADEKAHADONA EH-700 (manufactured by Adeka Industry Co., Ltd.), Rikasiddo HH (manufactured by Shin-Nippon Ewha Co., Ltd.), MH-700 (manufactured by Shin-Nippon Ewha Co., Ltd.), etc. can be heard

The curing agent and curing auxiliary compound exemplified above may be used alone or in combination of two or more.

The adhesion promoter is specifically, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(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-mercaptopropyltri One or a mixture thereof selected from the group consisting of methoxysilane, 3-isocyanatepropyltrimethoxysilane and 3-isocyanatepropyltriethoxysilane may be used. The adhesion promoter may be included in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 2 parts by weight, based on 100 parts by weight of the solid content of the colored photosensitive resin composition.

Specifically, the ultraviolet absorber may be 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, alkoxybenzophenone, or the like, but is not limited thereto.

The aggregation inhibitor may be specifically sodium polyacrylate, but is not limited thereto.

The colored photosensitive resin composition according to an embodiment of the present invention can be produced, for example, by the following method.

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 is about 0.2 µm or less. At this time, if necessary, the pigment dispersant (a2), part or all of the alkali-soluble resin (B), or the dye (a3) may be mixed with the solvent (E) to be dissolved or dispersed. The remainder of the alkali-soluble resin (B), the photopolymerizable compound (C), the photopolymerization initiator (D) and the additive (F) and, if necessary, the solvent (E) are further added to the mixed dispersion to a predetermined concentration in the present invention According to the color photosensitive resin composition can be prepared.

One embodiment of the present invention relates to a color filter formed using the above-described colored photosensitive resin composition. A color filter according to an embodiment of the present invention is characterized in that it includes a colored layer formed by applying the above-described colored photosensitive resin composition on a substrate and exposing and developing in a predetermined pattern.

Hereinafter, the pattern formation method using the coloring photosensitive resin composition of this invention is demonstrated in detail.

A method of forming a pattern using the colored photosensitive resin composition of the present invention may use a method known in the art, but typically a coating step; exposure step; and a removing step. By apply|coating the coloring photosensitive resin composition of this invention on a base material, photocuring and developing, and forming a pattern, it becomes possible to use as a colored pixel (colored image).

Specifically, the colored photosensitive resin composition is applied on a glass substrate on which nothing is applied or on a glass substrate on which SiNx (protective film) is applied to a thickness of 500 to 1,500 Å using a suitable method such as spin coating or slit coating, 2.0 to It is applied to a thickness of 3.4 μm. After application, light is irradiated to form a pattern required for the color filter. After irradiating the light, if the coating layer is treated with an alkali developer, the unirradiated portion of the coating layer is dissolved and a pattern required for the color filter is formed. By repeating this process according to the required number of R, G, and B colors, a color filter having a desired pattern can be obtained. Further, in the above process, crack resistance, solvent resistance, and the like can be further improved by heating the image pattern obtained by development again or curing it by irradiation with actinic rays or the like.

One embodiment of the present invention relates to an image display device provided with the above-described color filter.

The color filter of the present invention can display various images such as an electroluminescent display (EL), a plasma display (PDP), a field emission display (FED), and an organic light emitting diode (OLED), as well as a general liquid crystal display (LCD). Applicable to the device.

The image display apparatus of the present invention includes a configuration known in the art, except for having the above-described color filter.

An image display device according to an embodiment of the present invention includes, in addition to the above-described color filter, a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles A color filter may be additionally provided. In such a case, the emitted light of the light source applied to the image display apparatus is not particularly limited, but a light source emitting blue light may be preferably used in terms of superior color reproducibility.

The image display device according to an embodiment of the present invention may further include a color filter including only two color pattern layers among a red pattern layer, a green pattern layer, and a blue pattern layer in addition to the above-described color filter. In such a case, the color filter further includes a transparent pattern layer that does not contain quantum dot particles. When only two types of color pattern layers are provided, a light source emitting light of a wavelength representing the remaining colors that is not included may be used. For example, when only the red pattern layer and the green pattern layer are included, a light source emitting blue light may be used. In such a case, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer transmits the blue light as it is to display blue color.

Hereinafter, the present invention will be described in more detail by way of Examples, Comparative Examples and Experimental Examples. These Examples, Comparative Examples, and Experimental Examples are only for illustrating the present invention, and it is apparent to those skilled in the art that the scope of the present invention is not limited thereto.

Synthesis example One: xanthene synthesis of compounds

Step 1: Formula ( Aa -33- IM ) of the compound represented by

Into a flask equipped with a cooling tube and a stirring device, 1 part by weight of the compound represented by the formula (X) (a neutralizing agent), 7 parts by weight of N-methylpyrrolidone, 1.0 part by weight of potassium carbonate, and ethyl 4-bromobutyrate 2.0 parts by weight was added and stirred at 100°C for 7 hours and a half. After cooling, 20 parts by weight of 2N hydrochloric acid was added to the obtained reaction solution, followed by extraction twice with 45 parts by weight of chloroform, the chloroform layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and dried under reduced pressure at 60°C to obtain 4.1 parts by weight of a crude compound represented by the formula (Aa-33-IM).

Identification of the compound represented by the formula (Aa-33-IM)

(Mass spectrometry) Ionization mode = ESI ⁺ : m/z = [M + H] ⁺ 803.5

Exact　Mass:　802.3

Step 2: Formula ( Aa Synthesis of compounds represented by -33)

To a flask equipped with a cooling tube and a stirring device, 4.1 parts by weight of the compound represented by the formula (Aa-33-IM), 9.8 parts by weight of methanol, and 3.5 parts by weight of an 8% aqueous sodium hydroxide solution were added, and the mixture was stirred at room temperature for 6 hours. The resulting reaction solution was added to 30 parts by weight of 2N hydrochloric acid and stirred at room temperature for 30 minutes to precipitate crystals. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 1.0 parts by weight of the compound represented by the formula (Aa-33).

Identification of the compound represented by the formula (Aa-33)

(Mass spectrometry) Ionization mode = ESI ⁺ : m/z = [M + H] ⁺ 747.5

Exact　Mass:　746.3

Synthesis example 2: xanthene synthesis of compounds

Step 1: Formula ( Aa -41- IM Synthesis of compounds represented by )

In a flask equipped with a cooling tube and a stirring device, 5 parts by weight of 3,6-dichlorosulfone fluorescein represented by the above formula (XX) (a neutralizing agent), 35 parts by weight of N-methylpyrrolidone, and 3-amino- 12.2 parts by weight of methyl 4-methylbenzoate was added, followed by stirring at 130°C for 7 hours. After standing to cool, the obtained reaction solution was added to an aqueous solution of 7.5 parts by weight of concentrated hydrochloric acid and 70 parts by weight of ion-exchanged water, followed by stirring at room temperature for 30 minutes to obtain crystals. The crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 6.6 parts by weight of a compound represented by the following formula (Aa-41-IM).

Identification of the compound represented by the formula (Aa-41-IM)

(Mass spectrometry) Ionization mode = ESI ⁺ : m/z = [M + H] ⁺ 663.5

Exact　Mass: 662.2

Step 2: Formula ( Aa -44- IM ) of the compound represented by

In a flask equipped with a cooling tube and a stirring device, 6 parts by weight of the compound represented by the above formula (Aa-41-IM), 42 parts by weight of N-methylpyrrolidone, 5.0 parts by weight of potassium carbonate and 6.6 parts by weight of 1-bromopropane Parts were added, and it stirred at 90 degreeC for 6 hours. After standing to cool, the obtained reaction solution was added to 210 parts by weight of ion-exchanged water and stirred at room temperature for 30 minutes to obtain crystals. The crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 5.9 parts by weight of a compound represented by the following formula (Aa-44-IM).

Identification of the compound represented by the formula (Aa-44-IM)

(Mass spectrometry) Ionization mode = ESI ⁺ : m/z = [M + H] ⁺ 747.8

Exact　Mass: 746.3

Step 3: Formula ( Aa Synthesis of compounds represented by -44)

To a flask equipped with a cooling tube and a stirring device, 3 parts by weight of the compound represented by the formula (Aa-44-IM), 21 parts by weight of methanol, and 8.0 parts by weight of an 8% aqueous sodium hydroxide solution were added, and the mixture was stirred at room temperature for 8 hours. The obtained reaction solution was added to 105 parts by weight of 2N hydrochloric acid and stirred at room temperature for 30 minutes to obtain crystals. The crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 2.5 parts by weight of a compound represented by the following formula (Aa-44).

Identification of the compound represented by the formula (Aa-44)

(Mass spectrometry) Ionization mode = ESI ⁺ : m/z = [M + H] ⁺ 719.5

Exact　Mass: 718.2

production example 1: pigment dispersion M1 manufacture of

As a pigment, C.I. Pigment Blue 15:6 10.0 parts by weight, LPN-6919 (manufactured by BYK) 5.0 parts by weight as a pigment dispersant, 20 parts by weight of 4-hydroxy-4-methyl-2-pentanone and propylene glycol monomethyl ether acetate as a solvent 65.0 parts by weight were mixed and dispersed by a bead mill for 12 hours to prepare a pigment dispersion M1.

production example 2: pigment dispersion M2 manufacture of

As a pigment, C.I. Pigment Red 254 10.0 parts by weight, LPN-6919 (manufactured by BYK) 5.0 parts by weight as a pigment dispersant, 20 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent, and 65.0 parts by weight of propylene glycol monomethyl ether acetate The parts were mixed and dispersed for 12 hours by a bead mill to prepare a pigment dispersion M2.

production example 3: Pigment Dispersion M3 manufacture of

As a pigment, C.I. Pigment Blue 15:6 10.0 parts by weight, C.I. 1.0 parts by weight of Pigment Violet 23, 4.0 parts by weight of LPN-6919 (manufactured by BYK) as a pigment dispersant, 20 parts by weight of 4-hydroxy-4-methyl-2-pentanone as a solvent, and 65.0 parts by weight of propylene glycol monomethyl ether acetate The parts were mixed and dispersed by a bead mill for 12 hours to prepare a pigment dispersion M3.

production example 4: pigment dispersion M4 manufacture of

As a pigment, C.I. Pigment Blue 15:6 10.0 parts by weight, 5.0 parts by weight of LPN-6919 (manufactured by BYK) as a pigment dispersant, and 85.0 parts by weight of propylene glycol monomethyl ether acetate as a solvent Mix and disperse for 12 hours using a bead mill to disperse the pigment dispersion M4 was prepared.

production example 5: Pigment dispersion M5 manufacture of

As a pigment, C.I. Pigment Green 58 12.0 parts by weight, BYK LPN-6919 (manufactured by BYK) 4.0 parts by weight as a pigment dispersant, and 84.0 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and dispersed by a bead mill for 12 hours to obtain a pigment dispersion M5 prepared.

Synthesis example 3: Synthesis of alkali-soluble resin

100 parts by weight of propylene glycol monomethyl ether acetate, 100 parts by weight of propylene glycol monomethyl ether, 5 parts by weight of AIBN, 20.0 parts by weight of 2-ethylhexyl acrylate in a flask equipped with a stirrer, thermometer, reflux cooling tube, dropping funnel and nitrogen introduction tube. Parts by weight, 11.7 parts by weight of dicyclopentanyl methacrylate, 40.0 parts by weight of glycidyl methacrylate, and 3 parts by weight of n-dodecyl mercaptan were added and nitrogen substituted. Then, while stirring, the temperature of the reaction solution was raised to 80° C. and reacted for 4 hours. Then, after lowering the temperature of the reaction solution to room temperature and replacing the atmosphere of the flask with air from nitrogen, 0.2 parts by weight of triethylamine, 0.1 parts by weight of 4-methoxyphenol, and 20.3 parts by weight of acrylic acid were added and reacted at 100° C. for 6 hours. . Thereafter, the temperature of the reaction solution was lowered to room temperature, 8.0 parts by weight of succinic anhydride was added, and the reaction was conducted at 80° C. for 6 hours.

The alkali-soluble resin thus synthesized had a solid content acid value of 43.1 mgKOH/g, and a weight average molecular weight (Mw) measured by GPC was about 6,560.

Synthesis example 4: Synthesis of alkali-soluble resin

100 parts by weight of propylene glycol monomethyl ether acetate, 100 parts by weight of propylene glycol monomethyl ether, 2 parts by weight of AIBN, 13.0 parts by weight of acrylic acid, benzyl meta into a flask equipped with a stirrer, thermometer, reflux cooling tube, dropping funnel and nitrogen introduction tube 87 parts by weight of acrylate and 3 parts by weight of n-dodecyl mercaptan were added and nitrogen substituted. Thereafter, the temperature of the reaction solution was raised to 110° C. with stirring and reacted for 6 hours. The alkali-soluble resin thus synthesized had a solid content acid value of 93.2 mgKOH/g, and a weight average molecular weight (Mw) measured by GPC was about 12,800.

Example 1: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M1 of Preparation Example 1, 0.27 parts by weight of the compound represented by the formula (Aa-33) synthesized in Synthesis Example 1, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, KAYARAD DPHA (manufactured by Nippon Kayaku) 5.05 parts by weight, 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

Example 2: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M1 of Preparation Example 1, 0.27 parts by weight of the compound represented by the formula (Aa-44) synthesized in Synthesis Example 2, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, KAYARAD DPHA (manufactured by Nippon Kayaku) 5.05 parts by weight, 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

Example 3: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M2 of Preparation Example 2, 0.27 parts by weight of the compound represented by the formula (Aa-33) synthesized in Synthesis Example 1, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, KAYARAD DPHA (manufactured by Nippon Kayaku) 5.05 parts by weight, 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

comparative example 1: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M1 of Preparation Example 1, 0.27 parts by weight of Acid Red 289, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, 5.05 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), Igacure OXE 02 (manufactured by BASF) ) 0.81 parts by weight and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

comparative example 2: Preparation of colored photosensitive resin composition

27.27 parts by weight of the pigment dispersion M3 of Preparation Example 3, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, 5.05 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and propylene glycol A colored photosensitive resin composition was prepared by mixing 51.70 parts by weight of monomethyl ether acetate.

comparative example 3: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M4 of Preparation Example 4, 0.27 parts by weight of the compound represented by the formula (Aa-33) synthesized in Synthesis Example 1, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, KAYARAD DPHA (manufactured by Nippon Kayaku) 5.05 parts by weight, 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

comparative example 4: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M1 of Preparation Example 1, 0.27 parts by weight of the compound represented by the formula (Aa-33) synthesized in Synthesis Example 1, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, KAYARAD DPHA (manufactured by Nippon Kayaku) 5.05 parts by weight, 0.81 parts by weight of Igacure OXE 01 (manufactured by BASF) and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

comparative example 5: Preparation of colored photosensitive resin composition

27.0 parts by weight of the pigment dispersion M1 of Preparation Example 1, 0.27 parts by weight of the compound represented by the formula (Aa-33) synthesized in Synthesis Example 1, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 4, KAYARAD DPHA (manufactured by Nippon Kayaku) 5.05 parts by weight, 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and 51.70 parts by weight of propylene glycol monomethyl ether acetate were mixed to prepare a colored photosensitive resin composition.

comparative example 6: Preparation of colored photosensitive resin composition

27.27 parts by weight of the pigment dispersion M2 of Preparation Example 2, 15.17 parts by weight of the alkali-soluble resin of Synthesis Example 3, 5.05 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.81 parts by weight of Igacure OXE 02 (manufactured by BASF) and propylene glycol A colored photosensitive resin composition was prepared by mixing 51.70 parts by weight of monomethyl ether acetate.

production example 6: For evaluation of otitis Preparation of colored photosensitive resin composition

43.8 parts by weight of the pigment dispersion M5 of Preparation Example 5, 10.9 parts by weight of the alkali-soluble resin of Synthesis Example 3, 3.6 parts by weight of KAYARAD DPHA (Nippon Kayaku) as a photopolymerizable compound, 0.7 parts by weight of Igacure OXE 02 (manufactured by BASF) and 41.0 parts by weight of propylene glycol monomethyl ether acetate to prepare a colored photosensitive resin composition.

Experimental example One

A color filter was prepared as follows by using the colored photosensitive resin composition prepared in Examples and Comparative Examples, and changes in viscosity, generation of foreign matter over time, transmittance, adhesion, residue and color transfer were measured in the following manner.

<Manufacture of color filter>

The colored photosensitive resin composition was coated on a glass substrate of 2 inches in width and length by spin coating (“EAGLE XG” manufactured by Corning Corporation), and then placed on a heating plate and maintained at a temperature of 100° C. for 3 minutes to form a thin film. Then, a test photomask having a line/space pattern of 1 µm to 100 µm was placed on the thin film, and ultraviolet rays were irradiated with an interval of 300 µm from the test photomask. At this time, the ultraviolet light source was irradiated at 40 mJ/cm 2 using a 1KW high-pressure mercury lamp containing all of the g, h, and i lines, and no special optical filter was used. The thin film irradiated with ultraviolet light was developed by immersing it in a KOH aqueous solution developing solution having a pH of 10.5 for 80 seconds. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 230° C. for 20 minutes to prepare a color filter.

(1) Viscosity change

The initial viscosity of the colored photosensitive resin composition was measured, and the viscosity was measured and then stored at 5° C. for 1 month, and the viscosity change was evaluated according to the following evaluation criteria. Viscosity was measured at 25° C. with a Brookfield Viscometer DVI+ (manufactured by BROOKFIELD). The results are shown in Table 1 below.

<Evaluation criteria>

○: Viscosity change 5% or less

△: Viscosity change more than 5% to 10% or less

×: Viscosity change more than 10%

(2) Generation of foreign matter over time

After each of the colored photosensitive resin composition was stored at 5° C. for 1 month, the occurrence of foreign matter was observed by observation with a reflection type optical microscope (observation magnification 2,500 times), and evaluation was performed according to the following evaluation criteria. The results are shown in Table 1 below.

<Evaluation criteria>

◎: 2 or less foreign objects

○: 3 to 5 foreign substances

△: 6 to 10 foreign substances

×: 11 or more foreign objects

(3) transmittance

A color filter was manufactured in the same manner except that a test photomask was not used when manufacturing the color filter, and transmittance was measured using a colorimeter (manufactured by Olympus, OSP-200). The thickness of the manufactured color filter was 2.2 μm. The results are shown in Table 1 below.

(4) Adhesion

The generated pattern was observed through an optical microscope, and adhesion was evaluated according to the following evaluation criteria to the degree of tearing on the pattern. The results are shown in Table 1 below.

<Evaluation criteria>

○: No tearing in pattern

△: 1 to 4 rips in the pattern

×: 5 or more torn patterns

(5) residue

The colored photosensitive resin composition was coated on a glass substrate of 2 inches in width and length by spin coating (“EAGLE XG” manufactured by Corning Corporation), and then placed on a heating plate and maintained at a temperature of 100° C. for 3 minutes to form a thin film. The thin film was developed by immersing it in a developing solution of an aqueous KOH solution having a pH of 10.5 for 80 seconds. The glass substrate was washed with distilled water, dried by blowing nitrogen gas, and then the transmittance of the glass substrate was measured using a colorimeter (manufactured by Olympus, OSP-200), and the residue was evaluated according to the following evaluation criteria. The results are shown in Table 1 below.

<Evaluation criteria>

○: 99.7% or more

△: 99.5% or more to less than 99.7%

×: less than 99.5%

(6) otitis phenomenon

<Production of the lower base material>

A green color filter was prepared as a lower substrate by using the colored photosensitive resin composition for color transfer evaluation of Preparation Example 7 above.

Specifically, the colored photosensitive resin composition for color transfer evaluation of Preparation Example 7 was coated on a glass substrate of 2 inches in width and length by spin coating (“EAGLE XG” manufactured by Corning Corporation), and then vacuum dried at 65 Pa and placed on a heating plate. A thin film was formed by maintaining at a temperature of 100° C. for 3 minutes. Then, a photomask having a 1: 1 line/space pattern of 30 µm to 100 µm was placed on the thin film, and ultraviolet rays were irradiated with an interval of 300 µm from the photomask. At this time, the ultraviolet light source was irradiated with an illuminance of 40 mJ/cm 2 using a 1KW high-pressure mercury lamp containing all of the g, h, and i lines, and no special optical filter was used. The thin film irradiated with ultraviolet light was developed by immersing it in a developing solution of a KOH aqueous solution having a pH of 10.5 for 2 minutes. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 230° C. for 25 minutes to prepare a green color filter.

The film thickness of the green color filter prepared above was 2.3 μm. The transmittance of each pattern was measured with a colorimeter (manufactured by Olympus, OSP-200).

<Measurement of otitis>

Each of the colored photosensitive resin compositions prepared in Examples and Comparative Examples was coated on the green color filter, dried in a vacuum at 65 Pa, placed on a heating plate, and maintained at a temperature of 100° C. for 5 minutes to form a thin film. Then, a photomask having a 1: 1 line/space pattern of 30 µm to 100 µm was placed on the thin film perpendicular to the pattern of the green color filter as a lower substrate, and ultraviolet rays were irradiated with an interval of 300 µm from the photomask. At this time, the ultraviolet light source was irradiated with an illuminance of 40 mJ/cm 2 using a 1KW high-pressure mercury lamp containing all of the g, h, and i lines, and no special optical filter was used. The thin film irradiated with ultraviolet light was developed by immersing it in a developing solution of a KOH aqueous solution having a pH of 10.5 for 2 minutes. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 230° C. for 25 minutes to prepare a color filter. By measuring the transmittance at the point where the line pattern portion of the lower substrate and the upper space portion intersect, the transmittance change was calculated by Equation 1 below to evaluate the color transfer according to the following evaluation criteria. The results are shown in Table 2 below.

[Equation 1]

Transmittance change (%) = Transmittance after manufacturing blue or red color filter / Transmittance of initial green color filter × 100

<Evaluation criteria>

○: Transmittance change 99.5% or more

△: Transmittance change 99.0% or more and less than 99.5%

×: less than 99.0% change in transmittance

As the change in transmittance in a small pattern is small, the diffusivity of the dye is suppressed during high-temperature baking, so that there is no transfer of color to adjacent pixels, thereby realizing a high-resolution pixel.

adhesion residue transmittance change in viscosity foreign matter Example 1 ○ ○ 11.95 ○ ○ Example 2 ○ ○ 11.99 ○ ○ Example 3 ○ ○ 20.06 ○ ○ Comparative Example 1 ○ × 11.92 ○ ○ Comparative Example 2 ○ ○ 11.51 ○ ○ Comparative Example 3 ○ ○ 11.73 × × Comparative Example 4 × ○ 11.99 ○ ○ Comparative Example 5 △ × 11.91 ○ ○ Comparative Example 6 ○ ○ 19.65 ○ ○

composition measurement pattern 100㎛ 50㎛ 40㎛ 30㎛ Example 1 ○ ○ ○ △ Example 2 ○ ○ ○ ○ Example 3 ○ ○ ○ ○ Comparative Example 1 ○ △ × × Comparative Example 2 ○ ○ ○ ○ Comparative Example 3 ○ ○ ○ ○ Comparative Example 4 ○ △ △ × Comparative Example 5 ○ ○ △ △ Comparative Example 6 ○ ○ ○ ○

As shown in Table 1 and Table 2, wherein the colorant comprises a pigment and a dye, wherein the dye is -COOM or -COO within the ^molecule is greater claw comprises Santen compound, the alkali-soluble resin having a fentanyl-based DC The colored photosensitive resin composition of Examples 1 to 3, including a repeating unit, wherein the photopolymerization initiator includes an oxime ester compound in which a methyl radical is generated by irradiation with light, and the solvent includes an organic solvent having a hydroxyl group in the molecule It can be seen that silver has excellent transmittance, there is no residue or pattern tearing during color filter manufacturing, and not only has excellent storage stability, but also suppresses color transfer and does not reduce transmittance of adjacent pixels even at high resolution with a small pattern size. In particular, it was confirmed that the colored photosensitive resin composition for blue pixels of Examples 1 and 2 increased transmittance by 2% or more compared to the colored photosensitive resin composition for blue pixels of Comparative Example 2 in which a dye was not added. In addition, it was confirmed that the colored photosensitive resin composition for a red pixel of Example 3 increased transmittance by 2% or more compared to the colored photosensitive resin composition for a red pixel of Comparative Example 6 in which a dye was not added.

On the other hand, it was confirmed that the colored photosensitive resin compositions of Comparative Examples 1 to 6 had lower transmittance, or residues, pattern tearing, storage stability, or color transfer occurred during the manufacture of the color filter, thereby lowering transmittance of adjacent pixel portions.

As the specific part of the present invention has been described in detail above, for those of ordinary skill in the art to which the present invention pertains, it is clear that these specific techniques are only preferred embodiments, and the scope of the present invention is not limited thereto. do. Those of ordinary skill in the art to which the present invention pertains will be able to make various applications and modifications within the scope of the present invention based on the above contents.

Accordingly, the substantial scope of the present invention will be defined by the appended claims and their equivalents.

Claims (10)

A colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, and a solvent,
The colorant comprises a pigment and a dye,
The dye includes a xanthene compound represented by the following formula (4),
The alkali-soluble resin comprises a repeating unit represented by the following formulas 1 to 2,
The photopolymerization initiator includes an oxime ester compound in which a methyl radical is generated by light irradiation,
A colored photosensitive resin composition wherein the solvent includes an organic solvent having a hydroxyl group in the molecule:
[Formula 1]

[Formula 2]

[Formula 4]

In the above formula,
R ^a and R ^b are each independently a hydrogen atom or methyl,
R ^c is an alkyl group having 1 to 20 carbon atoms,
n and m are each independently an integer from 1 to 500,
R ¹ to R ⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and included in the saturated hydrocarbon group -CH ₂ - to be formed may be substituted with -O-, -CO- or -NR ^{11 -, R 1} and R ² may be bonded together to form a ring containing a nitrogen atom, R ³ and R ⁴ may be bonded together to form a ring containing a nitrogen atom,
R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms,
However, the compound represented by Formula 4 satisfies at least one of the requirements of (i) to (vi),
(i) R ¹ is a saturated hydrocarbon group having -COOM and having 1 to 20 carbon atoms ^{, at least one of R 2} to R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and in one molecule There is 1 -COOM included,
(ii) R ¹ and R ³ are an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM,
(iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM,
(iv) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM,
(v) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R ² is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM,
(vi) R ¹ and R ² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, ^{and at least one of R 3} and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM ego,
In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N(R ¹² ) ₄ , and four R ¹² may be the same or different,
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. According to claim 1, wherein the pigment is C.I. Pigment Blue 15:6, C.I. Pigment Red 254 or a colored photosensitive resin composition comprising a mixture thereof. delete The colored photosensitive resin composition according to claim 1, wherein the alkali-soluble resin further comprises a repeating unit represented by the following formula (3):
[Formula 3]

In the above formula,
R ^d and R ^f are each independently a hydrogen atom or methyl,
R ^e is a residue comprising a carboxylic acid derived from an acid anhydride,
q is an integer from 1 to 500; 5. The method of claim 4, wherein the acid anhydride is succinic anhydride, methylsuccinic anhydride, (2-dodeken-1-yl)succinic anhydride, phenylsuccinic anhydride, phthalic anhydride, maleic anhydride, citraconic anhydride, glutaric anhydride , 3,3-dimethylglutaric anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, trimellitic anhydride, hexahydrophthalic anhydride and carbic anhydride A photosensitive resin composition. The colored photosensitive resin composition of claim 1, wherein the organic solvent having a hydroxyl group in the molecule comprises 4-hydroxy-4-methyl-2-pentanone. The colored photosensitive resin composition according to claim 1, wherein the solvent further comprises propylene glycol monomethyl ether acetate. The colored photosensitive resin composition according to claim 7, wherein the mixing ratio of propylene glycol monomethyl ether acetate and the organic solvent having a hydroxyl group in the molecule is 95:5 to 60:40 by weight. A color filter formed by using the colored photosensitive resin composition according to any one of claims 1, 2, and 4 to 8. An image display device comprising the color filter according to claim 9 .