KR20120020482A - Pigment dispersion composition, color resist, and color filter - Google Patents

Abstract

PURPOSE: A pigment dispersion composition is provided to have dispersity and disperse stability with maintaining optical properties like brightness, contrast ratio, etc, and to manufacture a superior color filter. CONSTITUTION: A pigment dispersion composition comprises at least one kind of pigment derivative selected from a compound in chemical formula 1. In chemical formula 1, Q is organic pigment residue, m is the integer of 0-4, R1 is selected from hydrogen, a substituted or non-substituted C1-20 (hetero)alkyl group, and a substituted or a non-substituted C3-30 (hetero)aryl group. R2 and Ar is selected from hydrogen, halogen, an amine group, a cyano group, a nitro group, a substituted or non-substituted C1-60 (hetero) alkyl group, a substituted or non-substituted C3-60 (hetero) aryl group, a substituted or the non-substituted C1-60 (hetero) alkoxy group, a substituted or non-substituted C3-60 (hetero) aryloxy group, a substituted or the non-substituted C1-60 (hetero) alkylamine group, and a substituted or non-substituted C3-60 (hetero) arylamine group.

Description

Pigment dispersion composition, color resist and color filter manufactured using the same {PIGMENT DISPERSION COMPOSITION, COLOR RESIST, AND COLOR FILTER}

The present invention relates to a pigment dispersion composition, a color resist and a color filter produced using the same.

Color filters used in the manufacture of liquid crystal color displays, imaging devices, and the like are coated with a pigment dispersion composition for color filters in which three pigments of red (R), green (G), and blue (B) are respectively dispersed in the photosensitive resin liquid. It is manufactured by a method of forming a desired pixel by forming a colored film, and exposing and developing the colored film using a photomask to pattern the colored film.

As the characteristics required for the pigment dispersion composition for color filters, excellent optical properties such as high brightness, color power, and high contrast ratio, dispersibility, and storage stability are required. In order to prepare a pigment dispersion composition for satisfying these characteristics, fine pigment particles of 100 nm or less should be dispersed with a uniform distribution.

Conventional main techniques for obtaining fine pigments suitable for pigment dispersion compositions for color filters include salt milling, in which salt particles are refined using salt, and fine pigments having a desired particle size and distribution can be obtained using this method. To improve optical properties such as high brightness, coloring power and high contrast ratio. However, when the pigment becomes finer, the reagglomeration power of the pigment particles themselves becomes strong, and the dispersibility and dispersion stability of the pigment become poor, which is a problem. In order to solve this problem, a technique using a dispersant or the like is also known, but it is still insufficient to obtain the characteristics required for the above-mentioned use.

Therefore, there is a need for the development of a pigment dispersion composition which not only satisfies optical properties such as high brightness, coloring power, and high contrast ratio, but also sufficiently satisfies high dispersibility and dispersion stability.

In order to solve the above problems, the present invention provides a pigment dispersion composition capable of sufficiently satisfying optical properties such as brightness and contrast ratio, dispersibility and dispersion stability, a color resist composition including the pigment dispersion composition, and the color resist composition. It is an object to provide a color filter.

As a means for solving the above problems,

The present invention provides a pigment dispersion composition comprising an organic pigment and at least one pigment derivative selected from compounds represented by the following general formula (1).

<Formula 1>

(Wherein Q is an organic dye residue, m is an integer of 0 to 4, R1 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted C3 to 30 ( Hetero) aryl group, R2 and R3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted C3 A (hetero) aryl group of ~ 60, a substituted or unsubstituted (hetero) alkoxy group of 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group of 3 to 60 carbon atoms, a substituted or unsubstituted C1-C It is selected from a (hetero) alkylamine group of 60, a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms.)

At least one or more of the triazine group, sulfonic acid substituents or both are present in at least one of R2 and R3 of Formula 1, the sum of the triazine groups present in R2 and R3 is one or more, and the sulfonic acid substituents present in R2 and R3 The sum may be two or more.

Formula 1 may be more specific and added to the following formula (2) and formula (3).

<Formula 2>

(Wherein Q, m, R1, and R2 are the same as in general formula (1), and R4 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted (hetero) having 3 to 30 carbon atoms) R5 and R6 are each independently selected from hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted C3 to 60 group Of (hetero) aryl groups, substituted or unsubstituted (hetero) alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aryloxy groups having 3 to 60 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 60 carbon atoms It is selected from a (hetero) alkylamine group, a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms.)

<Formula 3>

Wherein Q, m, R 1, R 4, R 5, and R 6 are the same as those of Formula 2, and R 7 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted C 3 to 30 R8 and R9 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted A (hetero) aryl group having 3 to 60 carbon atoms, a substituted or unsubstituted (hetero) alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 1-60 (hetero) alkylamine group, or a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms.)

The present invention also provides a pigment dispersion composition, wherein the organic pigment residue Q is a quinophthalone residue.

In addition, at least one or more of R5 and R6 of Formula 2 provides a pigment dispersion composition, characterized in that 1 to 4 sulfonic acid substituents are present.

In addition, at least one or more of R5, R6, R8, R9 of the formula (3) provides a pigment dispersion composition characterized in that 1 to 4 sulfonic acid substituents are present.

In addition, the organic pigment, at least one or more selected from CI Pigment Red 122, CI Pigment Red 177, CI Pigment Red 254 and CI Pigment Violet 19 provides a pigment dispersion composition.

In addition, with respect to 100 parts by weight of the organic pigment, 0.1 to 30 parts by weight of the pigment derivative is provided to provide a pigment dispersion composition.

In addition, an organic solvent is further included, and the organic solvent provides a pigment dispersion composition comprising 100 to 1,000 parts by weight based on 100 parts by weight of the organic pigment.

The present invention also provides a color resist composition comprising the pigment dispersion composition and a photosensitive film forming material.

The present invention also provides a color filter, wherein a pixel is formed using the color resist composition.

The pigment dispersion composition of the present invention having the above structural features can provide excellent dispersibility and dispersion stability while maintaining excellent optical properties such as brightness and contrast ratio. The pigment dispersion composition of the present invention can be included as a color resist composition component to produce an excellent color filter.

Hereinafter, the present invention will be described in more detail with reference to Examples. The following descriptions are for specific examples of the present invention, but are not intended to limit the scope of the rights defined by the claims, even if there is an assertive or limited expression.

The present invention provides a pigment dispersion composition comprising an organic pigment and a pigment derivative having a special chemical structure. The pigment dispersion composition may optionally further include a dispersant, a resin, an organic solvent, an additive, and the like.

Each component is demonstrated concretely below.

Pigment Derivatives

Since the granulated pigment particles are thermodynamically unstable, they tend to agglomerate in a direction to reduce the specific surface area, particularly in the case of ultrafine particles that are excessively atomized during the atomization process. The pigment derivative of the present invention is composed of a special chemical structure to exhibit the effect of preventing reaggregation of the atomized pigment particles to improve the dispersion stability and storage stability.

Pigment derivative according to an embodiment of the present invention is characterized in that it comprises at least one pigment derivative selected from compounds represented by the following formula (1).

<Formula 1>

The pigment derivative of the formula (1) is characterized in that the triazine group is connected to the organic pigment residue Q without a link structure such as an alkylene group or an arylene group, and the pigment derivative of the formula (1) of the present invention is linked by a link structure such as an alkylene group or an arylene group It was found that storage stability and contrast characteristics were superior to pigment derivatives having a chemical structure bonded with a triazine group (see Comparative Example described later).

In Formula 1, Q is an organic pigment residue, m is an integer of 0 to 4, R1 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms It is selected from a (hetero) aryl group, R2 and R3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted carbon number A (hetero) aryl group of 3 to 60, a substituted or unsubstituted (hetero) alkoxy group of 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group of 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 It is selected from the (hetero) alkylamine group of -60, and a substituted or unsubstituted (hetero) arylamine group of 3 to 60 carbon atoms. The type of the substituent is not particularly limited and may be acceptable as long as it is a substituent capable of chemical structure substitution at the hydrogen position. On the other hand, the meaning of “(hetero)” means that carbon is substituted or unsubstituted by a hetero element such as oxygen, nitrogen, or sulfur. More preferably, at least one of R2 and R3 of Formula 1 is present in a triazine group, a sulfonic acid substituent or both, the sum of the triazine groups present in R2 and R3 is at least one, and present in R2 and R3 More preferably, the sum of sulfonic acid substituents is two or more (see Examples).

When the organic pigment used in the pigment dispersion composition is at least one selected from CI Pigment Red 122, CI Pigment Red 177, CI Pigment Red 254 and CI Pigment Violet 19, Q is particularly preferably a quinophthalone moiety. .

Formula 1 is more preferably a compound represented by the following formula (2). Formula 2 is characterized in that two triazine structures have a structure joined by an amine group.

<Formula 2>

In Chemical Formula 2, Q, m, R1, and R2 are the same as those of Chemical Formula 1, and R4 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted C3-30 (hetero) R5 and R6 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted C3 to 60 (hetero) aryl groups, substituted or unsubstituted (hetero) alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aryloxy groups having 3 to 60 carbon atoms, substituted or unsubstituted carbon atoms 1 to 60 It is selected from the (hetero) alkylamine group of substituted, unsubstituted or unsubstituted (hetero) arylamine group of 3 to 60 carbon atoms.

In addition, at least one or more of R 5 and R 6 of Formula 2 may have 1 to 4 sulfonic acid substituents.

Formula 1 is also preferably a compound represented by the following formula (3). Formula 3 is characterized in that three triazine structures have a structure linked by an amine group.

<Formula 3>

In the above formula, Q, m, R1, R4, R5, R6 are the same as in the general formula (2), R7 is hydrogen, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms It is selected from a (hetero) aryl group, R8 and R9 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted carbon number A (hetero) aryl group of 3 to 60, a substituted or unsubstituted (hetero) alkoxy group of 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group of 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 It is selected from the (hetero) alkylamine group of -60, and a substituted or unsubstituted (hetero) arylamine group of 3 to 60 carbon atoms.

At least one or more of R 5, R 6, R 8, and R 9 of Formula 3 may have 1 to 4 sulfonic acid substituents.

In the pigment dispersion composition according to the embodiment of the present invention, the blending ratio of the pigment derivative is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the organic pigment, and more preferably 1 to 20 parts by mass. When the compounding ratio of the said pigment derivative is too small, it becomes difficult to fully acquire the target effect. Moreover, even if the said mixing | blending ratio is too much, the effect which is not proportional to it is not acquired, and it becomes a factor which reduces the various physical properties of a pigment composition and the coloring composition using the same, and changes the original color largely.

<Pigment>

The kind of pigment is not particularly limited. Red, green, blue, yellow, purple pigments and the like may be used alone or in combination. Examples of the organic pigments include azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinonepigments, and isododoline pigments. pigments, dioxazine pigments, quinophthalone pigments, diketopyrrolopyrole pigments, anthraquinone pigments, thioindigo pigments, Metal complex pigments and the like, but are not limited thereto.

C.I. Pigment Red 7, 14, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 146, 177, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272, etc. may be used, and in the case of the green pigment CI Pigment Green 7, 10, 36, 37, such as green pigments can be used, and in the case of the blue pigment C.I. Pigment Blue 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 80 and the like can be used, and the yellow pigment, C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214 and the like can be used, and in the case of the purple pigment CI Pigment Violet 23, 34, 35, 37, etc. can be used, These can be used individually or in mixture of 2 or more types.

In particular, in the case of a red pigment dispersion composition, the organic pigment is C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254 and C.I. It is preferred to select at least one from pigment violet 19.

The pigment described above is modified on the surface of the pigment derivative, which means that the pigment derivative is pulverized and bound on the surface of the atomized pigment through a grinding and dispersing process such as milling. It is possible to improve. That is, the pigment derivative forms a coating layer on the surface of the pigment, which means a continuous or discontinuous coating layer. Through the surface layer of such a pigment derivative, it becomes possible to improve the dispersion stability, storage stability and color characteristics of the pigment.

It is not necessary to combine the pigment derivative and the pigment which show the same color, and it is also possible to use the substance which shows a different color as needed. That is, it is possible to modify the surface of the red pigment with a yellow pigment derivative and to improve color characteristics, and also to improve color purity by using pigments and pigment derivatives having the same color.

<Dispersant>

In order to disperse | distribute the said pigment etc. in the said organic solvent, it is preferable to use a dispersing agent, Although it is not limited as such a dispersing agent, It is preferable to use a high molecular weight dispersing agent.

As the high molecular weight dispersant, preferably those having a weight average molecular weight in the range of 1,000 to 100,000 can be used, and more preferably, a high molecular weight dispersant having a weight average molecular weight of 10,000 to 30,000 is used. As such a high molecular weight dispersant, a commercially available product, for example, trade names EFKA4046 (manufactured by EFKA), PB-821 (manufactured by Ajinomoto Fine Techno), BYPER's DISPERBIK 160, 161, 162, 163, 164, 182 , 184 (brand name), SOLVESSE 22000, 24000, 28000 (brand name) of Avecia Limited, DISPARLON DA-234, 325, 375, 725 (brand name) of Kusumoto Kasei Corporation Although these etc. are mentioned, It is not limited to these.

Such a high molecular weight dispersant is not limited but may be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the pigment. If the dispersant content is less than 1 part by weight, a sufficient dispersing effect cannot be obtained, and if it exceeds 30 parts by weight, economical efficiency is lowered, which is not preferable.

<Resin>

The pigment dispersion composition may further include a resin. Examples include petroleum resin, casein, shellac, rosin-modified maleic acid resin, rosin-modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber, phenolic resin, alkyd resin, Polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylic resin, methacryl resin, polyurethane resin, silicone resin, fluorine resin, dry oil, synthetic dry oil , Styrene-modified maleic acid resins, polyamide resins, polyimide resins, benzoguanamine resins, melamine resins, urea resin polypropylene chlorides, butyral resins and vinylidene chloride resins.

Furthermore, a photosensitive resin can be used as the resin. As the photosensitive resin, for example, a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group by reaction between the linear polymer and a (meth) acryl compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group or cinnamic acid Linear polymer containing a resin obtained by introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group and an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer And a resin obtained by semi-esterification of a (meth) acryl compound having a hydroxy group such as hydroxyalkyl (meth) acrylate can be used. Such a resin can be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the pigment.

<Organic Solvents>

The organic solvent used in the pigment dispersion composition is not particularly limited as long as it can disperse the pigment and the like, and a solvent selected from esters of 3 to 12 carbon atoms, ketones, ethers, alcohols, hydrocarbons and the like is preferable. The ester, ketone, ether or alcohol may have a ring structure. Compounds having two or more functional groups (-O-, -CO- and -COO-) such as esters, ketones and ethers may also be used as the solvent, and other functional groups such as alcoholic hydroxy may be present at the same time. In the case of a solvent having two or more functional groups, many carbon atoms may be present within the range defined for the compound having the functional group.

Examples of the ester having 3 to 12 carbon atoms include ethyl formate, propyl formate, pentyl formate, methyl acetate, ethyl acetate or pentyl acetate. Examples of the ketone having 3 to 12 carbon atoms include acetone, methyl isobutyl ketone, methyl ethyl ketone, diethyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone and methylcyclohexanone. Examples of the ether having 3 to 12 carbon atoms include propylene glycol monomethyl ether acetate, diisopropyl ether, dimethoxymethane, dimethoxyethane, 1,4-dioxane, 1,3-dioxane, tetrahydrofuran, Anisole and phenitol are exemplified. Moreover, 2-ethoxyhexyl acetate, 2-methoxyethanol, and 2-butoxyethanol are mentioned as an organic solvent which has 2 or more types of functional groups. Alcohols usable in combination with the chlorinated organic solvents are also linear, branched or cyclic, of which saturated aliphatic hydrocarbons are preferred. The hydroxy group of the alcohol may be monovalent, divalent or trivalent. Examples of the alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, 1-pentanol, 2-methyl-2butanol, and cyclohexanol. Examples of the fluorinated alcohols include 2-fluoroethanol, 2,2,2-trifluoroethanol or 2,2,3,3-tetrafluoro-1-propanol. In addition, the hydrocarbon may be linear, branched or cyclic, and an aromatic hydrocarbon or an aliphatic hydrocarbon may be used. Aliphatic hydrocarbons can be used both saturated and unsaturated. Examples of such hydrocarbons include cyclohexane, hexane, benzene, ethylbenzene, toluene and xylene.

Such an organic solvent may be used in an amount capable of dispersing the pigment particles in the pigment dispersion composition, and is not particularly limited, but may be used in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the pigment. If the content of the organic solvent is less than 100 parts by weight, sufficient pigment dispersion cannot be obtained, the viscosity is high, and workability is lowered. If the content is more than 1,000 parts by weight, the pigment concentration is too low, making it difficult to sufficiently express a desired color. have.

<Other additives>

In addition, conventional auxiliaries or additives, such as surfactants, fillers, standardizers, antifoams, anti-dust agents, enhancers, antistatic agents, preservatives, drying retardants, wetting agents, antioxidants and the like, preferably the total weight of the pigment dispersion composition It may further comprise in an amount of 0.01 to 10% by weight, in particular 0.5 to 5% by weight.

On the other hand, in order to manufacture a pigment dispersion composition, it is transparency of the pigment composition obtained by using an organic pigment whose primary particle diameter is 100 nm or less, or using an organic pigment which made the primary particle diameter 100 nm or less by an atomization process. It is preferable from a viewpoint of the improvement of sharpness. As a method for atomizing the pigment, for example, a salt milling method for milling in the presence of a common salt, etc. (for example, JP-A-2001-220520 and JP-A-2001-264528) ), But is not limited to these.

The pigment dispersion composition according to the embodiment of the present invention may be prepared by mixing the organic pigment and the pigment derivative, respectively, by a conventionally known method (for example, Japanese Patent Application Laid-Open No. 2001-271004 and 2004-91497). have. For example, the method of mixing the powder of the said organic pigment and the said pigment derivative, the method of mixing the suspension of the said organic pigment and the said pigment derivative disperse | distributed to the water or the solvent which is soluble, and the process of manufacturing an organic pigment Although the method of adding the said pigment derivative to the process of etc. is mentioned, a manufacturing method is not specifically limited. As arbitrary processes in the said organic pigment manufacturing process, salt milling is mentioned, for example, It is not limited to this. When adding the said pigment derivative, although a form of powder, paste, and suspension is mentioned, it is not limited to this.

As an example, the pigment dispersion composition of the present invention may be prepared through a wet dispersion stabilization process of wetting the pigment powder while mixing a suitable amount of the above components and mixing with a stirrer, the pigment in the composition thus prepared is 20 to It has an average particle size of 150 nm. At this time, in consideration of the efficiency of the pigment dispersion, to maximize the physical impact force bead (beads) of 0.05 to 2.0mm diameter (beads) can be used, such beads may be a material such as glass, stainless steel or zirconium.

In addition, dispersers used in the stirring process include bead mills, roll mills, attritors, super mills, dissolvers, homomixers, sand mills, 3-roll mills, disc mills, paintsakers, and scandex. Bead mills are the most used.

On the other hand, the pigment dispersion composition of the present invention can also be used as a coating material, printing ink and the like, and can be applied as a pigment dispersion color resist composition which can be mixed with a photosensitive film forming material and capable of image formation by light irradiation. When the pixel is formed by a known method and structure using the color resist composition containing the pigment dispersion composition of the present invention, a color filter having excellent characteristics is obtained. A color resist composition is obtained by mixing and dispersing the pigment dispersion composition of this invention and the photosensitive film formation material. The photosensitive film forming material is not particularly limited. Generally, photosensitive resin varnishes, such as photosensitive polyacrylate resin, photosensitive acrylic resin, photosensitive polyamide resin, photosensitive polyimide resin, or photosensitive unsaturated polyester resin, or monomer or oligomer are further added as such a resin reaction diluent. Consisting of varnishes, photoinitiators (with sensitizers as necessary), solvents and the like. By using the pigment dispersion composition of this invention, the color resist composition for color filter pixel formation and color filter excellent in dispersibility, dispersion stability, transparency, and clarity can be obtained.

As said monomer or oligomer, (meth) acrylic acid ester, (meth) acrylic acid, (meth) acrylamide, vinyl acetate, styrene, (meth) acrylonitrile, (meth) acrylate oligomer, etc. are mentioned, for example. It is not limited to these. Examples of the photoinitiator include, but are not limited to, acetphenone series, benzoin series, benzophenone series, thioxanthone series, triazine series, carbazole series, imidazole series, and the like. Examples of the sensitizer include acylphosphine oxide, methylphenylglyoxylate, quinone-based, anthraquinone-based, and isophthalophenone-based. based, ester-based, benzyl-based, benzophenone-based and the like, but are not limited to these. Examples of the solvent include (poly) alkylene glycol monoalkyl ethers, (poly) alkylene glycol monoalkyl ether acetates, ethers, ketones, lactic acid alkyl esters, other esters, aromatic hydrocarbons, amides, and the like. It is not limited to these.

Hereinafter, specific examples and synthesis methods of the pigment derivative will be described through specific examples. The following description is an example of the present invention and is not limited to the listed structures and descriptions.

<Examples>

Preparation of Pigment Derivatives

(1) Synthesis of Pigment Derivative A

5 g of Pigment Yellow 138 and 28.5 ml of Chlorosulfonic acid were reacted at 50 ° C for 2 hours. Then, 9 g of thionyl chloride was added dropwise, reacted at 50 ° C. for 4 hours, and cooled to obtain a precipitate with ice water.

0.91 g of 2,4-Diamino-6-methyl-1,3,5-triazine was added thereto, reacted at 20 ° C. for 4 hours, filtered, washed with water, and dried to obtain a final product.

(2) Synthesis of Pigment Derivative B

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 0.92 g of N, N-dimethylethylenediamine was added dropwise and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative A was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(3) Synthesis of Pigment Derivative C

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 1.31 g of 2-Aminoethanesulfonic acid was added thereto and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative A was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(4) Synthesis of Pigment Derivative D

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 1.81 g of 4-Aminobenzenesulfonic acid was added thereto and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative A was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(5) Synthesis of Pigment Derivative E

5 g of the pigment derivative A was dissolved in 85 ml of Acetone, 0.89 g of Benzyl bromide was added dropwise, and reacted for 4 hours. Acetone was distilled off to obtain a final product.

(6) Synthesis of Pigment Derivative F

5 g of Pigment Yellow 138 and 28.5 ml of Chlorosulfonic acid were reacted at 50 ° C for 2 hours. Then, 9 g of thionyl chloride was added dropwise, reacted at 50 ° C. for 4 hours, and cooled to obtain a precipitate with ice water.

0.92 g of 1,3,5-Triazine-2,4,6-triamine was added thereto, reacted at 20 ° C. for 4 hours, filtered, washed with water, and dried to obtain a final product.

(7) Synthesis of Pigment Derivative G

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 0.92 g of N, N-dimethylethylenediamine was added dropwise and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative F was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(8) Synthesis of Pigment Derivative H

1.92 g of cyanuric chloride was dissolved in 40 ml of Acetone, and 1.84 g of N, N-dimethylethylenediamine was added dropwise and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative F was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(9) Synthesis of Pigment Derivative I

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 1.31 g of 2-Aminoethanesulfonic acid was added thereto and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative F was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(10) Synthesis of Pigment Derivative J

1.92 g of cyanuric chloride was dissolved in 40 ml of Acetone, and 2.61 g of 2-Aminoethanesulfonic acid was added and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative F was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(11) Synthesis of Pigment Derivative K

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 1.81 g of 4-Aminobenzenesulfonic acid was added thereto and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative F was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(12) Synthesis of Pigment Derivative L

1.92g of cyanuric chloride was dissolved in 40ml of Acetone, and 3.61g of 4-Aminobenzenesulfonic acid was added thereto and reacted at 20 ° C for 4 hours. Thereafter, 5 g of the pigment derivative F was dissolved in 85 ml of Acetone, and added dropwise and reacted for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(13) Synthesis of Pigment Derivative M

5 g of Pigment Yellow 138 and 28.5 ml of Chlorosulfonic acid were reacted at 50 ° C for 2 hours. Then, 9 g of thionyl chloride was added dropwise, reacted at 50 ° C. for 4 hours, and cooled to obtain a precipitate with ice water.

1.35 g of 2,4-Diamino-6-phenyl-1,3,5-triazine was added thereto, reacted at 20 ° C. for 4 hours, filtered, washed with water, and dried to obtain a final product.

(14) Synthesis of Pigment Derivative N

0.96 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 0.86 g of N, N-dimethylethylenediamine was added dropwise and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative M was dissolved in 85 ml of Acetone, and added dropwise thereto, followed by reaction for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(15) Synthesis of Pigment Derivative O

0.91 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 1.23 g of 2-Aminoethanesulfonic acid was added and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative M was dissolved in 85 ml of Acetone, and added dropwise and reacted for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(16) Synthesis of Pigment Derivative P

0.91 g of cyanuric chloride was dissolved in 20 ml of Acetone, and 1.70 g of 4-Aminobenzenesulfonic acid was added and reacted at 20 ° C. for 4 hours. Thereafter, 5 g of the pigment derivative M was dissolved in 85 ml of Acetone, and added dropwise and reacted for 4 hours. After completion of the reaction, the mixture was cooled and Hexane was added to obtain a precipitate. After filtration, washing and drying to obtain a final product.

(17) Synthesis of Pigment Derivative Q

5 g of Pigment Yellow 138 and 28.5 ml of Chlorosulfonic acid were reacted at 50 ° C for 2 hours. Then, 9 g of thionyl chloride was added dropwise, reacted at 50 ° C. for 4 hours, and cooled to obtain a precipitate with ice water.

1.25 g of 4-Chloro-3-nitroaniline was added thereto, reacted at 20 ° C. for 4 hours, filtered, washed with water, and dried to obtain a secondary product. The obtained secondary product was dissolved in 100 ml of THF, 0.91 g of 2,4-Diamino-6-methyl-1,3,5-triazine was added and refluxed for 7 hours, and then Hexane was added to obtain a precipitate. Drying gave the final product.

(18) Synthesis of Pigment Derivative R

5 g of Pigment Yellow 138 and 28.5 ml of Chlorosulfonic acid were reacted at 50 ° C for 2 hours. Then, 9 g of thionyl chloride was added dropwise, reacted at 50 ° C. for 4 hours, and cooled to obtain a precipitate with ice water.

1.25 g of 4-Chloro-3-nitroaniline was added thereto, reacted at 20 ° C. for 4 hours, filtered, washed with water, and dried to obtain a secondary product. The resulting secondary product was dissolved in 100 ml of THF, 0.91 g of 1,3,5-Triazine-2,4,6-triamine was added and refluxed for 7 hours. Hexane was added to obtain a precipitate, which was filtered, washed, and dried. The final product was obtained.

(19) Synthesis of Pigment Derivative S

5 g of Pigment Yellow 138 and 28.5 ml of Chlorosulfonic acid were reacted at 50 ° C for 2 hours. Then, 9 g of thionyl chloride was added dropwise, reacted at 50 ° C. for 4 hours, and cooled to obtain a precipitate with ice water.

1.25 g of 4-Chloro-3-nitroaniline was added thereto, reacted at 20 ° C. for 4 hours, filtered, washed with water, and dried to obtain a secondary product. The obtained secondary product was dissolved in 100 ml of THF, 1.36 g of 2,4-Diamino-6-phenyl-1,3,5-triazine was added and refluxed for 7 hours. Then, Hexane was added to obtain a precipitate, which was filtered and washed. Drying gave the final product.

<Production of Pigment Dispersion Composition>

Example  1-16 and Comparative example  1-3

Pigment, pigment derivative, dispersant, resin for dispersing, and solvent were mixed in the composition ratio as shown in Table 1 below, and 100 g of 0.5 mm zirconia was added thereto, followed by dispersion for 5 hours in a paint shaker to obtain a pigment dispersion composition.

<Evaluation of Examples and Comparative Examples>

Each composition was evaluated using the patterns formed using the pigment dispersion compositions of Examples 1 to 16 and Comparative Examples 1 to 3, and the results are shown in Table 2 below. Unless otherwise specified, the evaluation standard or a conventional method commonly used in the art).

(1) contrast

The pigment dispersion compositions of Examples 1 to 16 and Comparative Examples 1 to 3 were spin-coated to a glass substrate having a thickness of 0.5 mm of 60 mm x 60 mm size so that x = 0.650 after curing (C light source) was 90. After drying for 100 seconds at 100 ° C., an ultra-high pressure mercury lamp was used to perform ultraviolet exposure with a cumulative amount of light of 60 mJ / cm 2. The coated glass substrate was heated at 230 ° C. for 90 minutes, and then the luminance meter CT-1 (Tsubosaka) and The contrast value was computed using the polarizing plate as the ratio of the brightness in parallel and the brightness in orthogonality.

(2) luminance

The RY at x = 0.650 (C light source) was measured using a color luminance meter MCPD 3000 (Otsuka Co., Ltd.) as the luminance meter. In Dispaly, the x and y coordinates of each RGB component are represented by one point, where x is the size of the red component in the chromatic diagram and RY is the brightness of the red component (y is the size of the green component, GY is the size of the green component). Brightness, z is the magnitude of the blue component, BY is the brightness of the blue component).

(3) viscosity measurement

The pigment dispersion compositions of Examples 1 to 16 and Comparative Examples 1 to 3 were measured using DV-II + VISCOMETER (Brookfield) at an initial viscosity of 25 ° C. at 25 ° C., and then stored in a 25 ° C. low temperature incubator. After 20 days, the viscosity (based on 25 ℃) was measured to determine the change in viscosity over time.

TABLE 2 Evaluation results of Examples and Comparative Examples

As shown in Table 2, it can be seen that the pigment dispersion composition according to the embodiment of the present invention is excellent in storage stability due to the slight change in viscosity with time, and has a very good contrast compared to the pigment dispersion composition of the comparative example.

In particular, the pigment dispersion composition according to an embodiment of the present invention has a contrast of 3000 or more, except for a part, when the evaluation is performed according to the above-mentioned evaluation method, and when the luminance is measured, it is 21.0 cd / m 2 or more, and 20 days from the initial stage. The subsequent viscosity change is very good, below 4 cps.

Since the above description is an example for better understanding of the present invention, modifications, substitutions, modifications, omissions, and the like which can be added within the scope of the technical idea of the present invention are within the scope of the present invention defined by the claims. Included.

Claims (13)

A pigment dispersion composition comprising an organic pigment and at least one pigment derivative selected from compounds represented by the following general formula (1).

<Formula 1>

(Wherein Q is an organic dye residue, m is an integer of 0 to 4, R1 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted C3 to 30 ( Hetero) aryl group, R2 and R3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted C3 A (hetero) aryl group of ~ 60, a substituted or unsubstituted (hetero) alkoxy group of 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group of 3 to 60 carbon atoms, a substituted or unsubstituted C1-C It is selected from a (hetero) alkylamine group of 60, a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms.)
The pigment dispersion composition of claim 1, wherein the pigment derivative is a compound represented by the following Chemical Formula 2.

<Formula 2>

Wherein Q, m, R1, and R2 are the same as in Formula 1, and R4 represents hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted (hetero) group having 3 to 30 carbon atoms R5 and R6 are each independently selected from hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted C3 to 60 group Of (hetero) aryl groups, substituted or unsubstituted (hetero) alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aryloxy groups having 3 to 60 carbon atoms, substituted or unsubstituted carbon atoms having 1 to 60 carbon atoms It is selected from a (hetero) alkylamine group, a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms.)
The pigment dispersion composition according to claim 2, wherein the pigment derivative is a compound represented by the following Chemical Formula 3.

<Formula 3>

Wherein Q, m, R 1, R 4, R 5, and R 6 are the same as those of Formula 2, and R 7 is hydrogen, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted C 3 to 30 R8 and R9 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted A (hetero) aryl group having 3 to 60 carbon atoms, a substituted or unsubstituted (hetero) alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 1-60 (hetero) alkylamine group, or a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms.)
The pigment dispersion composition of claim 1, wherein the organic pigment residue Q is a quinophthalone residue.
The compound according to claim 1, wherein at least one of R2 and R3 of Formula 1 is present with a triazine group, a sulfonic acid substituent, or both, and the sum of the triazine groups present in R2 and R3 is at least one, and in R2 and R3, A pigment dispersion composition, characterized in that the sum of the sulfonic acid substituents present is two or more.
The pigment dispersion composition of claim 2, wherein at least one of R 5 and R 6 in Formula 2 has 1 to 4 sulfonic acid substituents.
The pigment dispersion composition of claim 3, wherein at least one of R 5, R 6, R 8, and R 9 of Formula 3 has 1 to 4 sulfonic acid substituents.
The pigment dispersion composition of claim 1, wherein the organic pigment is selected from at least one of CI Pigment Red 122, CI Pigment Red 177, CI Pigment Red 254, and CI Pigment Violet 19.
The pigment dispersion composition according to claim 1, wherein the pigment derivative is contained in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the organic pigment.
The pigment dispersion composition of claim 1, further comprising an organic solvent, wherein the organic solvent is included in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the organic pigment.
The method according to any one of claims 1 to 10, wherein the contrast is measured at least 3000 based on the evaluation method of the embodiment, the luminance is measured at least 21.0 cd / m 2, and the change in viscosity after 20 days from the initial stage is 4 cps. The pigment dispersion composition characterized by the following.
The color resist composition containing the pigment dispersion composition of any one of Claims 1-10, and the photosensitive film formation material.
The pixel is formed using the color resist composition of Claim 12, The color filter characterized by the above-mentioned.