KR101597603B1 - Dye-hybridized pigment derivatives, pigment dispersion composition, photo-sensitive color composition, and color filte - Google Patents

Abstract

The present invention relates to a dye hybrid pigment derivative (formula (1)) which can provide excellent color characteristics, such as tinting strength, which is a merit of a dye while eliminating the heat resistance which is a disadvantage of the dye, , A pigment dispersion composition, a photosensitive coloring composition including the pigment dispersion composition, and a color filter using the photosensitive coloring composition.
≪ Formula 1 >

Description

DYE-HYBRIDIZED PIGMENT DERIVATIVES, PIGMENT DISPERSION COMPOSITION, PHOTO-SENSITIVE COLOR COMPOSITION, AND COLOR FILTE, DYE HYBRID PIGMENT DERIVATIVES, PHOTO-SENSITIVE COLOR COMPOSITION, AND COLOR FILTER

The present invention relates to a dye hybrid pigment derivative, a pigment dispersion composition, a photosensitive coloring composition, and a color filter made using the same.

The color filter used in the production of liquid crystal color display and image pickup device is made by applying a pigment dispersion composition for a color filter in which three colors of red (R), green (G), and blue (B) To form a colored film, and the colored film is exposed and developed by using a photomask to form a desired colored film by patterning the colored film.

To date, techniques for manufacturing color filters are divided into four types, namely, dyeing method, vapor deposition method, printing method and pigment dispersion method. Among them, pigment dispersion method is applied as the most general technique of manufacturing color filters.

Although the pigment dispersion method is applied as the most general technique, this technique has problems in that the transparency or contrast is lowered due to agglomeration of the pigment particles. In contrast, the dye-type color filter, which does not require a dispersion process, has a characteristic of showing high transmittance and contrast because there is little scattering effect of particles due to molecular particles because there is little intermolecular aggregation.

Generally, dyes have excellent advantages in spectral characteristics such as color purity and transparency due to molecular behavior, but they are difficult to maintain the inherent color of RGB in the liquid crystal alignment process (230 ° C) because the stability against heat is lower than that of the pigments. And the like. Particularly, it is a key point to improve the heat resistance which is a necessary condition for commercialization of the dye type color filter.

DISCLOSURE OF THE INVENTION In order to solve the above problems, it is an object of the present invention to provide a dye hybrid pigment derivative having advantages of a dye while solving the drawbacks of the dye.

Another object of the present invention is to provide a pigment dispersion composition, a photosensitive coloring composition, and a color filter manufactured using the same, wherein redispersibility is greatly improved by introducing a functional group having improved water resistance and water resistance.

As means for solving the above problem,

The present invention provides a pigment derivative represented by the following formula (1).

≪ Formula 1 >

[In the above formula (1)

R ₁ to R ₃ are each independently of the other hydrogen, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, mono (C 1 -C 30) alkylamino, di Amino, di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;

,

,

,

,

,

, 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;A or B

,

,

,

,

,

(C1-C30) alkyl, (C6-C30) alkoxy, (C6-C30) aryl, mono Arylamino or di (C6-C30) arylamino;

R ₄ are each independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30 (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,

R ₅ is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6-C30) aryl, (C6-C30) aralkyl (C1-C30) alkyl, ( C3-C30) heteroaryl, (C1-C30) alkylcarbonyl,

o is an integer from 1 to 3,

p is an integer of 1 to 2, and when o and p are 2 or more, R ₄ may be the same or different;

M is Na, H, K, or Li;

Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of R ₁ to R ₃ above; R ₄ is alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl; And the alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of A or B are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C1- , (C6-C30) aryl, (C3-C30) heteroaryl, and the like.

Reacting a compound of formula (4) and a compound of formula (5) to obtain a compound of formula (6); And reacting the compound of formula (6) with the following formula (7) and (8) to prepare a pigment derivative represented by formula (1).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

AX

[Chemical Formula 8]

BX

The pigment dispersion composition containing the dye hybrid pigment derivative of the present invention having the above-mentioned constitutional characteristics can provide excellent color characteristics such as tinting power which is advantageous of dyes while solving the heat resistance which is a disadvantage of dyes, The re-solubility can be greatly improved.

Hereinafter, the present invention will be described in more detail with reference to examples. Although the following description relates to a specific example of the present invention, even if there is a definite and definite expression, the scope of the right defined by the claims is not limited.

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

Each component will be described in detail below.

<Pigment Derivative>

The pigment derivative according to one embodiment of the present invention is a dye hybrid pigment derivative. That is, it has a structure in which the pigment structure is denatured and derivatized with a dye structure. As a result, heat resistance and coloring power can be improved. In addition, since the finely divided pigment particles are thermodynamically unstable, they tend to agglomerate in the direction of reducing the specific surface area. Especially, in the case of ultra-fine tenants that are over-finely atomized during the atomization process, they tend to agglomerate. The pigment derivative of the present invention further comprises a specific chemical structure, thereby exhibiting an effect of preventing re-aggregation of the finely divided pigment particles, thereby improving dispersion stability and storage stability. In addition, by introducing a functional group having excellent water resistance, excellent solubility is provided.

The pigment derivative according to one embodiment of the present invention is characterized by containing at least one kind of pigment derivative selected from compounds represented by the following formula (1).

&Lt; Formula 1 >

[In the above formula (1)

R ₁ to R ₃ are each independently of the other hydrogen, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, mono (C 1 -C 30) alkylamino, di Amino, di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;

,

,

,

,

,

, 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;A or B

,

,

,

,

,

(C1-C30) alkyl, (C6-C30) alkoxy, (C6-C30) aryl, mono Arylamino or di (C6-C30) arylamino;

R ₄ are each independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30 (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,

R ₅ is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6-C30) aryl, (C6-C30) aralkyl (C1-C30) alkyl, ( C3-C30) heteroaryl, (C1-C30) alkylcarbonyl,

o is an integer from 1 to 3,

p is an integer of 1 to 2, and when o and p are 2 or more, R ₄ may be the same or different;

M is Na, H, K, or Li;

Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of R ₁ to R ₃ above; R ₄ is alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl; And the alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of A or B are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C1- , (C6-C30) aryl, (C3-C30) heteroaryl, and the like.

Specific examples of the above-mentioned formula (1) include the following derivatives. However, the present invention is not limited to the following examples.

The derivative (D-1)

The derivative (D-2)

The derivative (D-3)

The derivative (D-4)

The derivative (D-5)

The derivative (D-6)

The derivative (D-7)

The derivative (D-8)

In the pigment dispersion composition according to one embodiment of the present invention, the proportion of the pigment derivative is preferably 0.05 to 30 parts by mass, more preferably 0.1 to 20 parts by mass, particularly preferably 0.1 to 20 parts by mass based on 100 parts by mass of the organic pigment. 5 parts by mass is preferable. If the mixing ratio of the pigment derivative is too low, it is difficult to sufficiently obtain the desired effect. In addition, even if the blending ratio is too large, the effect proportional thereto can not be obtained, and the physical properties of the pigment composition and the coloring composition using the pigment composition are lowered, thereby causing the original color to largely change.

<Pigment>

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

In the case of the red pigment, 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, 210, 246, 254, 255, 264, 270, and 272 may be used. In the case of the green pigment, CI Pigment Green 7, 10, 36, 37 and the like can be used. In the case of the blue pigment, C.I. Blue pigments such as Pigment Blue 15: 1,15: 2,15: 3,15: 4,15: 6,16,80 can be used. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 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, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 169, 170, 171, 172, 173, 193, 194, 199, 213 and 214 can be used. In the case of the purple pigment, CI Pigment Violet 23, 34, 35, 37, etc. These may be used alone or in combination of two or more.

Particularly, in the case of the red pigment dispersion composition, the organic pigment is preferably selected from the group consisting of C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254 and C.I. Pigment Violet &lt; SEP &gt; 19 &lt; SEP &gt;

The above-mentioned pigment is surface-modified with the pigment derivative, which means that the pigment derivative is pulverized through milling and dispersion processes such as milling, and is bonded on the surface of the finely divided pigment, whereby the properties of the pigment It becomes possible to improve. That is, the pigment derivative forms a coating layer on the surface of the pigment, which means a continuous or non-continuous coating layer. The dispersion stability, storage stability and color characteristics of the pigment can be improved through the surface layer of the pigment derivative.

It is preferable to use the same series of the pigment coloring residue of the pigment derivative and the pigment. However, it is not always necessary to be the same, and it is not always necessary to combine those which exhibit the same hue, and it is also possible to use a material exhibiting a different hue if necessary. That is, it is also possible to modify the surface of the red pigment with a yellow pigment derivative to improve the color characteristic, and it is also possible to improve the color purity by using pigments and pigment derivatives having the same color.

<Dispersant>

In order to disperse the pigment or the like in the organic solvent, it is preferable to use a dispersing agent. The dispersing agent is not limited, but it is preferable to use a high molecular weight dispersing agent.

The high molecular weight dispersant may preferably have a weight average molecular weight in the range of 1,000 to 100,000, and more preferably 10,000 to 30,000 in the high molecular weight dispersant. Examples of such a high molecular weight dispersant include commercially available products such as EFKA4046 (trade name, manufactured by EFKA), PB-821 (manufactured by Ajinomoto Fine Techno), DISPERBIK 160, 161, 162, 163, 164 and 182 , DISPARLON DA-234, 325, 375, 725 (trade name) of Auxia Limited, SOLSPERSE 22000, 24000, 28000 (trade name) , But are not limited thereto.

The high molecular weight dispersant may be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the pigment. If the content of the dispersant is less than 1 part by weight, a sufficient dispersing effect can not be obtained. If the amount is more than 30 parts by weight, economical efficiency and color characteristics are deteriorated.

<Resin>

The pigment dispersion composition may further contain a resin. Examples of the thermoplastic resin include petroleum resin, casein, shellac, rosin-modified maleic resin, rosin-modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, A vinyl chloride resin, a vinyl chloride-vinyl acetate copolymer, an acrylic resin, a methacrylic resin, a polyurethane resin, a silicone resin, a fluorine resin, a drying oil, a synthetic drying oil, a polyester resin, an unsaturated polyester resin, an amino resin, , A styrene-modified maleic resin, a polyamide resin, a polyimide resin, a benzoguanamine resin, a melamine resin, a urea resin polypropylene chloride, a butyral resin and a vinylidene chloride resin.

Furthermore, a photosensitive resin can be used as the resin. As the photosensitive resin, a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group by reaction between a (meth) acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group or cinnamic acid, A linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an? -Olefin-maleic anhydride copolymer and a resin obtained by introducing a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group into a linear polymer having And (meth) acrylic compounds 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 solvent>

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 is preferably a solvent selected from esters, ketones, ethers, alcohols and hydrocarbons having 3 to 12 carbon atoms. 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 can also be used as solvents and other functional groups such as alcoholic hydroxyl groups can be present at the same time. In the case of a solvent having two or more functional groups, a large number of carbon atoms may be present within a defined range 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 phenetole are examples. Examples of the organic solvent having two or more functional groups include 2-ethoxyhexyl acetate, 2-methoxyethanol and 2-butoxyethanol. The alcohols usable in combination with the chlorinated organic solvent may be 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 alcohol include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, 1-pentanol, 2-methyl-2-butanol and cyclohexanol. Examples of the fluorinated alcohols include 2-fluoroethanol, 2,2,2-trifluoroethanol and 2,2,3,3-tetrafluoro-1-propanol. The hydrocarbons may be linear, branched or cyclic, and aromatic hydrocarbons or aliphatic hydrocarbons may be used. Aliphatic hydrocarbons can be used both saturated and unsaturated. Examples of such hydrocarbons include cyclohexane, hexane, benzene, ethylbenzene, toluene and xylene.

The organic solvent may be used in an amount that can disperse the pigment particles in the pigment dispersion composition. The organic solvent 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 can not be obtained, viscosity becomes high and workability is lowered, and when the amount is more than 1,000 parts by weight, the pigment concentration is too low, have.

<Other additives>

It is also possible to use conventional additives or additives such as surfactants, fillers, standardizers, antifoaming agents, antidandruff agents, enhancers, antistatic agents, preservatives, drying retarders, wetting agents and antioxidants, In an amount of 0.01 to 10% by weight, in particular 0.5 to 5% by weight, based on the total weight of the composition.

On the other hand, in order to prepare the pigment dispersion composition, it is preferable that the organic pigment has a primary particle diameter of 100 nm or less, or an organic pigment having a primary particle diameter of 100 nm or less by the atomization treatment, It is preferable from the viewpoint of improvement of sharpness. Examples of the atomization treatment of the pigment include a salt-milling method in which milling is carried out in the presence of a common salt (see, for example, JP-A-2001-220520 and JP-A-2001-264528 ), But the present invention is not limited thereto.

The pigment dispersing composition according to one embodiment of the present invention can be produced by mixing the organic pigment and the pigment derivative by a conventionally known method (for example, Japanese Patent Laid-Open Nos. 2001-271004 and 2004-91497) have. Examples thereof include a method of mixing powders of the organic pigment and the pigment derivative, a method of mixing suspensions between the organic pigment and the pigment derivative dispersed in water or a dissolvable organic solvent, And a method of adding the above pigment derivative to the process of the present invention, but the production method is not particularly limited. Examples of the optional step in the organic pigment production process include, but are not limited to, salt milling. The state of adding the pigment derivative may be in the form of powder, paste or suspension, but is not limited thereto.

As an example, the pigment dispersion composition of the present invention can be prepared through a wet dispersion stabilization process in which the respective components are added in an appropriate amount and wetted with the pigment powder while mixing with an agitator, and the pigment in the thus- And an average particle size of 150 nm. In order to maximize the physical impact force in consideration of the efficiency of pigment dispersion, beads having a diameter of 0.05 to 2.0 mm may be used. Such beads may be glass, stainless steel, zirconium or the like.

Examples of the dispersing machine used in the stirring step include a bead mill, a roll mill, an attritor, a super mill, a dissolver, a homomixer, a sand mill, a 3-roll mill, a disc mill, a paint shaker and a scandel. Bead mill is the most used.

On the other hand, the pigment dispersion composition of the present invention can be used as a paint, a printing ink, etc., and can be applied as a pigment-dispersed color resist composition which can be mixed with a photosensitive film-forming material and form an image by light irradiation. When a pixel is formed by a known method and structure using a color resist composition including the pigment dispersion composition of the present invention, a color filter having excellent characteristics is obtained. The color resist composition is obtained by mixing the pigment dispersion composition of the present invention and a photosensitive film-forming material in a highly dispersed state. The photosensitive film-forming material is not particularly limited. In general, a photosensitive resin varnish such as a photosensitive polyacrylate resin, a photosensitive acrylic resin, a photosensitive polyamide resin, a photosensitive polyimide resin or a photosensitive unsaturated polyester resin, or a monomer or oligomer is further added as such a resin reaction diluent A varnish, a photoinitiator (if necessary, together with a sensitizer), and a solvent. By using the pigment dispersion composition of the present invention, it is possible to obtain a color resist composition and a color filter for color filter pixel formation which are excellent in dispersibility, dispersion stability, transparency and clarity.

Examples of the monomer or oligomer include (meth) acrylic acid ester, (meth) acrylic acid, (meth) acrylamide, vinyl acetate, styrene, (meth) acrylonitrile, , But are not limited thereto. Examples of the photoinitiator include, but are not limited to, acetophenone, benzoin, benzophenone, thioxanthone, triazine, carbazole, and imidazole. Examples of the sensitizer include acylphosphine oxide, methylphenylglyoxylate, quinone-based, anthraquinone-based, isophthalophenone-based, based, ester-based, benzyl-based, benzophenone-based, and the like. Examples of the solvent include (poly) alkylene glycol monoalkyl ether, (poly) alkylene glycol monoalkyl ether acetate, ether, ketone, fatty acid alkyl ester, other esters, aromatic hydrocarbons and amides. But are not limited thereto.

Meanwhile, the pigment derivative of Formula 1 may be prepared by various methods without limitation. In a preferred embodiment of the present invention, there is provided a process for preparing a pigment derivative represented by the formula (1) by reacting a compound of the formula (6) with a compound of the formula (7) .

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

AX

[Chemical Formula 8]

BX

[In the above formulas (1) and (4) to (8)

R ₁ to R ₃ are each independently of the other hydrogen, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, mono (C 1 -C 30) alkylamino, di Amino, di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;

,

,

,

,

,

, 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;A or B

,

,

,

,

,

(C1-C30) alkyl, (C6-C30) alkoxy, (C6-C30) aryl, mono Arylamino or di (C6-C30) arylamino;

R ₄ are each independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30 (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,

R ₅ is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6-C30) aryl, (C6-C30) aralkyl (C1-C30) alkyl, ( C3-C30) heteroaryl, (C1-C30) alkylcarbonyl,

o is an integer from 1 to 3,

p is an integer of 1 to 2, and when o and p are 2 or more, R ₄ may be the same or different;

M is Na, H, K, or Li;

Each X is independently a leaving group;

Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of R ₁ to R ₃ above; R ₄ is alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl; And the alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of A or B are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C1- , (C6-C30) aryl, (C3-C30) heteroaryl, and the like.

Specific examples of the pigment derivative, synthesis method and the like will be described below through specific examples. The following description is only an example of the present invention, and thus the present invention is not limited to the structure or the description.

<Examples>

Production Example 1 < Synthesis of pigment-dye hybrid derivative (D-1) >

After dissolving cyanuric chloride (6.5 g, 35 mmol, 2.7 eq) in 30 ml of acetone, 3,5-diamino-2,4,6-trimethyl benzenesulfonic acid (3 g, 13 mmol, 1 eq) Add slowly to the flask at O &lt; 0 &gt; C. Na ₂ CO ₃ (2M) and set it to PH 6. After 2 hours of reaction, the reaction mixture is worked up with distilled water (100 ml X 3), filtered off with water and then dried with MgSO ₄ . (6.2 g, yield 86.8%)

To a solution of 3,5-bis ((4,6-dichloro-1,3,5-triazine-2-yl) amino) -2,4,6-trimethylbenzenesulfonic acid (5 g, 9.1 mmol, 1 eq) Add hexylamine (2.6 ml, 19.1 mmol, 2.1 eq) slowly at room temperature. Add Na ₂ CO ₃ (2M) to PH 6. After 6 hours of reaction, the reaction mixture is worked up with distilled water (100 ml X 3), dried with MgSO ₄ , filtered and dried. (4.5 g, yield 72.8%).

The flask was charged with 3,5-bis ((4-chloro-6- (hexylamino) -1,3,5-triazine-2-yl) amino) -2,4,6-trimethylbenzenesulfonic acid ) Was dissolved in 15 ml of benzene and then sodium 6 - ((2-hydroxynaphthalen-1-yl) diazenyl) naphthalene-2-sulfonate (3.7 g, 9.2 mmol, 2.1 eq) and sodium bicarbonate (0.7 g, 8.8 mmol, 2.0 eq ), And the mixture was refluxed at 85 ° C for 24 hours. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the solvent, and then worked up with distilled water (100 ml X 3), filtered off with MgSO ₄ , filtered and dried to obtain D-1. (5.1 g, yield 81.9%).

Production Example 2 < Synthesis of pigment-dye hybrid derivative (D-2) >

The flask was charged with 3,5-bis ((4-chloro-6- (hexylamino) -1,3,5-triazine-2-yl) amino) -2,4,6-trimethylbenzenesulfonic acid (4.4 g, 9.2 mmol, 2.1 eq) and sodium bicarbonate (0.7 g, 8.8 mmol) were dissolved in 15 ml of benzene, and sodium 4 - ((2,4-dimethylphenyl) diazenyl) -3-hydroxynaphthalene-2,7-disulfonate , 2.0 eq), and the mixture was refluxed at 85 ° C for 24 hours. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the solvent. Then, the reaction mixture was worked up with distilled water (100 ml × 3), dried over MgSO ₄ , filtered and dried to obtain D-2. (5.5 g, yield 79.3%).

Production Example 3 < Synthesis of pigment-dye hybrid derivative (D-3) >

The flask was charged with 3,5-bis ((4-chloro-6- (hexylamino) -1,3,5-triazine-2-yl) amino) -2,4,6-trimethylbenzenesulfonic acid eq) was dissolved in 15 ml of benzene and sodium 4 - ((2-hydroxy-6-sulfonatonaphthalen-1-yl) diazenyl) naphthalene-1-sulfonate (4.6 g, 9.2 mmol, 2.1 eq) and sodium bicarbonate , 8.8 mmol, 2.0 eq), and the mixture was refluxed at 85 ° C for 24 hours. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove the solvent, and then worked up with distilled water (100 ml X 3), filtered off with MgSO ₄ , filtered and dried to obtain D-3. (5.8 g, yield 81.3%).

Production Example 4 < Synthesis of pigment-dye hybrid derivative (D-4) >

The flask was charged with 3,5-bis ((4-chloro-6- (hexylamino) -1,3,5-triazin-2-yl) amino) -2,4,6-trimethylbenzenesulfonic acid ) Was dissolved in 15 ml of benzene and sodium 7-hydroxy-8 - ((4-sulfonatonaphthalen-1-yl) diazenyl) naphthalene-1,3-disulfonate (5.6 g, 9.2 mmol, 2.1 eq) and sodium bicarbonate 0.7 g, 8.8 mmol, 2.0 eq), and the mixture was refluxed at 85 ° C for 24 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the solvent was distilled off (100 ml X 3). After work-up, water was removed with MgSO ₄ , filtered, and dried to obtain AR18B. (6.4 g, yield 80.6%).

Production Example 5 < Synthesis of pigment-dye hybrid derivative (D-5) >

(5.0 g, 12 mmol) and octylboronic acid (2.1 g, 14 mmol) in a 250 ml two neck Schlenk flask and a solution of sodium 1-amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene- Was injected with 80 ml of toluene and 1M-K ₂ CO ₃ and bubbled with N ₂ gas. After the temperature was raised to 90, the catalyst Tetrakis (triphenylphosphine) palladium (0.7 g, 0.001 mol) was added and the temperature was raised to 125 ° C and stirred for 24 hours. After completion of the reaction, the reaction mixture was extracted with CHCl ₃ , washed with H ₂ O three times, dried over MgSO ₄ , and purified by flash column chromatography to obtain a compound. (7.0 g, yield 71.4%).

sodium 3,5-bis ((4-chloro-6- (hexylamino) -1,3,5-triazin-2-yl) amino) -2,4,6-trimethylbenzenesulfonate (3 g, 4.4 mmol, 1 eq) Is dissolved in 60 ml of acetone and sodium 1-amino-4-octyl-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (4.0 g, 9.2 mmol, 2.1 eq) is slowly added. Na ₂ CO ₃ (2M) to adjust to pH 6, and then increase the temperature. After 6 hours of reaction, the reaction mixture was worked up with distilled water (100 ml × 3), dried over MgSO ₄ , filtered and dried to obtain D-4. (5.2 g, yield 79.3%).

Production Example 6 < Synthesis of pigment-dye hybrid derivative (D-6) >

bis (4-chloro-1,3,5-trimethyl-5-sulfonato-1,3-phenylene) bis (azanediyl)) sodium 1,1 '- ((6,6' bis (4-octyl-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate) (3 g, 2.2 mmol, 1 eq) 3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-amine (0.8 g, 4.6 mmol, 2.1 eq) is slowly added. Na ₂ CO ₃ (2M) to adjust to pH 6, and then increase the temperature. After 6 hours of reaction, the reaction mixture was worked up with distilled water (100 ml × 3), dried over MgSO ₄ , filtered and dried to obtain D-6. (3.0 g, yield 82.9%).

Production Example 7 < Synthesis of pigment-dye hybrid derivative (D-7) >

bis (4-chloro-1,3,5-trimethyl-5-sulfonato-1,3-phenylene) bis (azanediyl)) sodium 1,1 '- ((6,6' bis (4-octyl-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate) (3 g, 2.2 mmol, 1 eq) After dissolving, 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3 (2H) -one (0.95 g, 4.6 mmol, 2.1 eq) is slowly added. Na ₂ CO ₃ (2M) to adjust to pH 6, and then increase the temperature. After 6 hours of reaction, the reaction mixture is worked up with distilled water (100 ml × 3), dried with MgSO ₄ , filtered, and dried to obtain BAPOB. (2.9 g, yield 78.5%).

Production Example 8 < Synthesis of pigment-dye hybrid derivative (D-8) >

bis (4-chloro-1,3,5-trimethyl-5-sulfonato-1,3-phenylene) bis (azanediyl)) sodium 1,1 '- ((6,6' bis (4-octyl-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate) (3 g, 2.2 mmol, 1 eq) was dissolved in 60 ml of acetone Sodium 3-amino-7-sulfonaphthalene-2-sulfonate (1.5 g, 4.6 mmol, 2.1 eq) is slowly added. Na ₂ CO ₃ (2M) to adjust to pH 6, and then increase the temperature. After 6 hours of reaction, the reaction mixture is worked up with distilled water (100 ml X 3), filtered off with MgSO ₄ , filtered and dried to obtain D-8. (3.4 g, yield 78.4%)

Reference Example 1 Preparation of acrylic resin solution 1 (AR-1)

700 g of cyclohexanone was added to a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introducing tube and a stirrer, and heated to 80 ° C. After the inside of the reaction vessel was purged with nitrogen, 133 g of n-butyl methacrylate, 46 g of 2-hydroxyethyl methacrylate, 43 g of methacrylic acid and 74 g of para-cumylphenol ethylene oxide modified acrylate (manufactured by Toagosei Co., Ltd. , ARONIX M110) and 4.0 g of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further maintained for 3 hours to obtain a solution of an acrylic resin having a weight average molecular weight (Mw) of 26,000. After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 캜 for 20 minutes to measure the nonvolatile content. Propylene glycol monoethyl ether acetate was added to the resin solution so that the nonvolatile matter was 20% by weight Acrylic resin solution was prepared.

Reference Example 2 <Preparation of red-treated pigment 1 (RK-1)

200 parts of diketopyrrolopyrrole red pigment CI Pigment Red 254 (IRGAZIN RED 2030, manufactured by Ciba), 1400 parts of sodium chloride and 350 parts of diethylene glycol were put into a stainless steel 1 gallon kneader (manufactured by Inoue Manufacturing Co., Ltd.) And kneaded at 80 DEG C for 6 hours. Next, this kneaded product was charged into 7000 parts of hot water and stirred for 2 hours while being heated to 80 DEG C to form a slurry, followed by filtration and washing with water to remove sodium chloride and diethylene glycol, followed by drying at 80 DEG C overnight, 190 parts of diketopyrrolopyrrole-based atomized pigment 1 (RK-1) was obtained.

[Example 1]

(Pigment dispersion composition (RD-1))

The following mixture was stirred and mixed, and then dispersed for 4 hours with Eigermill (mini model M-250 MKII, manufactured by Eiger Japan) using zirconia beads having a diameter of 0.2 mm, To prepare a pigment dispersion composition (RD-1) having a volatile component of 20 wt%.

Atomized pigment 1 (RK-1): 11.3 parts

(C.I. Pigment Red 254)

Acrylic resin solution 1: 21.2 parts

Resin type dispersant solution (SP55000 manufactured by Lubrizol): 8.2 parts

Dye derivative (derivative (D-1)): 0.5 part

Propylene glycol monomethyl ether acetate (PGMAC): 58.8 parts

[Examples 2 to 8]

The pigment dispersion compositions (RD-2 to RD-8) were prepared in the same manner as in the pigment dispersion composition (RD-1) except that the pigment, the resinous dispersant and the derivative were changed to the compositions shown in Table 1.

[Remark Example 1]

The pigment dispersion composition (RD-9) was prepared in the same manner as in the pigment dispersion composition (RD-1), except that the pigment, the resinous dispersant and the derivative were changed to the compositions shown in Table 1.

division Pigment dispersion composition
No. Mixing ratio Pigment Pigment derivative Dispersant Suzy PGMAC Kinds Amount (% by weight) Kinds Amount (% by weight) Amount (% by weight) Amount (% by weight) Amount (% by weight) Example 1 RD-1 RK-1 11.3 D-1 0.5 8.2 21.2 58.8 Example 2 RD-2 11.3 D-2 0.5 8.2 21.2 58.8 Example 3 RD-3 11.3 D-3 0.5 8.2 21.2 58.8 Example 4 RD-4 11.3 D-4 0.5 8.2 21.2 58.8 Example 5 RD-5 11.3 D-5 0.5 8.2 21.2 58.8 Example 6 RD-6 11.3 D-6 0.5 8.2 21.2 58.8 Example 7 RD-7 11.3 D-7 0.5 8.2 21.2 58.8 Example 8 RD-8 11.3 D-8 0.5 8.2 21.2 58.8 Remark Example 1 RD-9 11.8 - - 8.2 21.2 58.8

[Evaluation of coloring composition (pigment dispersion) for color filter]

The respective compositions were evaluated using patterns formed using the pigment dispersion compositions of Examples 1 to 8, and the results are shown in Table 2. (Items not specifically described in the evaluation method or standard will be referred to as &quot; According to an evaluation standard or an ordinary method commonly used in the field).

<Viscosity characteristics>

The initial viscosity (based on 25 ° C) was measured at 30 rpm using DV-II + VISCOMETER (Brookfield) in the pigment dispersion compositions of Examples 1 to 8, and after 15 days of storage at 25 ° C in a low temperature incubator, And the change in viscosity over time was confirmed. The results are shown as ⊚ (almost no increase in viscosity), ∘ (slight increase in viscosity but available range), Δ (unusable due to viscosity increase), × (not available due to significant viscosity increase).

<Contrast>

The pigment dispersion compositions of Examples 1 to 8 were spin-coated on a glass substrate of 60 mm × 60 mm size having a plate thickness of 0.5 so that x = 0.650 (C light source) after curing, dried at 90 ° C. for 100 seconds, The coated glass substrate was heated at 230 占 폚 for 30 minutes using a mercury lamp and irradiated with ultraviolet light at a total light amount of 60 mJ / cm2. Then, each dried coating film was irradiated with UV light using a luminometer CT-1 (Tsubosaka) The contrast value was calculated as the ratio of the luminance in the case of the right-handed case and the case of the right-handed case.

<Brightness>

As a luminance meter, RY was measured at x = 0.650 (C light source) using a color luminance meter MCPD 3000 (Otsuka). The x and y coordinates of each component of RGB on the display are represented by a point, where x is the size of the red component in the chromaticity 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 size of the blue component, and BY is the brightness of the blue component).

&Lt; Evaluation of heat resistance &

The pigment dispersion composition was coated on the transparent substrate so that the dry coating film was about 1.0, and dried at 70 DEG C for 20 minutes. Thereafter, the coated film was heated in an oven at 230 占 폚 for 1 hour and then cooled. The obtained coating film was measured with a Luminance spectrophotometer (OSP-SP200, manufactured by Olympus Optical Co., Ltd.) The measurements (L * (1), a * (1), b * (1)) were performed. (2), a * (2), and b * (2)) were similarly performed by heating in an oven at 250 ° C for one hour in the heat resistance test and the color difference? Eab * And the heat resistance of the coating film was evaluated in the following four stages.

△ Eab * = √ ((L * (2) -L * (1)) 2 + (a * (2) -a * (1)) 2 + (b * (2) -b * (1)) 2 )

⊚: △ Eab * is less than 1.5

?: Eab * is not less than 1.5 and not more than 3.0

DELTA: Eab * was 3.0 or more and less than 5.0

X:? Eab * is 5.0 or more

The results are shown in Table 2 below.

division Pigment dispersion composition Viscosity Contrast Luminance Heat resistance Early 15th Example 1 RD-1 5.8 5.8 3990 19.5 ◎ Example 2 RD-2 5.8 5.8 4040 19.5 ◎ Example 3 RD-3 5.6 5.5 3890 19.5 ○ Example 4 RD-4 5.5 5.5 4120 19.5 ◎ Example 5 RD-5 5.6 5.7 3980 19.5 ◎ Example 6 RD-6 5.9 6.0 4070 19.4 ◎ Example 7 RD-7 5.4 5.4 3960 19.4 ◎ Example 8 RD-8 6.1 6.1 3900 19.5 ◎ Remark Example 1 RD-9 9.5 12.3 3520 19.2 △

As shown in Table 2, it can be confirmed that the embodiment of the present invention is excellent in storage stability, contrast, luminance, and heat resistance.

[Example 9]

(Photosensitive coloring composition (RP-1))

The following mixture (100 parts in total) was stirred and mixed so as to be uniform, and then filtered through a 4.0 占 퐉 filter to obtain a photosensitive coloring composition (RP-1).

Pigment dispersion composition (RD-1): 50.0 parts

Acrylic resin solution 1: 7.5 parts

Photopolymerizable monomer (ARONIX M-402 manufactured by Toagosei Co., Ltd.): 2.0 parts

Dipentaerythritol hexaacrylate

Photopolymerization initiator (OXE-02 manufactured by Ciba): 1.5 parts

1- (9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]

Propylene glycol monomethyl ether acetate (PGMAC): 39.0 parts

[Examples 10 to 16, Remark Example 2]

(Photosensitive coloring composition (RP-2-9))

Photosensitive coloring compositions (RP-2 to RP-9) were obtained in the same manner as in the photosensitive coloring composition (RP-1) except that the pigment dispersion composition was changed from Table 3. In the preparation of each photosensitive coloring composition, 100 parts of the photosensitive coloring composition was adjusted by adding the total amount of the pigment dispersion composition to 50 parts.

division Photosensitive
Coloring composition No. Mixing ratio Pigment dispersion composition Suzy Monomer Initiator PGMAC Kinds Amount (% by weight) Amount (% by weight) Amount (% by weight) Amount (% by weight) Amount (% by weight) Example 9 RP-1 RD-1 50.0 7.5 2.0 1.5 39.0 Example 10 RP-2 RD-2 50.0 7.5 2.0 1.5 39.0 Example 11 RP-3 RD-3 50.0 7.5 2.0 1.5 39.0 Example 12 RP-4 RD-4 50.0 7.5 2.0 1.5 39.0 Example 13 RP-5 RD-5 50.0 7.5 2.0 1.5 39.0 Example 14 RP-6 RD-6 50.0 7.5 2.0 1.5 39.0 Example 15 RP-7 RD-7 50.0 7.5 2.0 1.5 39.0 Example 16 RP-8 RD-8 50.0 7.5 2.0 1.5 39.0 Remark Example 2 RP-9 RD-9 50.0 7.5 2.0 1.5 39.0

[Evaluation of coloring composition (photosensitive coloring composition) for color filter]

The respective compositions were evaluated using patterns formed using the photosensitive coloring compositions of Examples 9 to 16, and the results are shown in Table 4. (The matters not specifically described in the evaluation method or standard will be described later in the description According to an evaluation standard or an ordinary method commonly used in the field).

<Contrast>

The pigment-dispersed compositions of Examples 9 to 16 were spin-coated on a glass substrate having a size of 60 mm × 60 mm having a plate thickness of 0.5 so that x = 0.650 (C light source) after curing, dried at 90 ° C. for 100 seconds, The coated glass substrate was heated at 230 占 폚 for 30 minutes using a mercury lamp and irradiated with ultraviolet light at a total light amount of 60 mJ / cm2. Then, each dried coating film was irradiated with UV light using a luminometer CT-1 (Tsubosaka) The contrast value was calculated as the ratio of the luminance in the case of the right-handed case and the case of the right-handed case.

<Brightness>

As a luminance meter, RY was measured at x = 0.650 (C light source) using a color luminance meter MCPD 3000 (Otsuka). The x and y coordinates of each component of RGB on the display are represented by a point, where x is the size of the red component in the chromaticity 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 size of the blue component, and BY is the brightness of the blue component).

&Lt; Evaluation of heat resistance &

The pigment dispersion composition was coated on the transparent substrate so that the dry coating film was about 1.0, and dried at 70 DEG C for 20 minutes. Thereafter, the coated film was heated in an oven at 230 占 폚 for 1 hour and then cooled. The obtained coating film was measured with a Luminance spectrophotometer (OSP-SP200, manufactured by Olympus Optical Co., Ltd.) The measurements (L * (1), a * (1), b * (1)) were performed. (2), a * (2), and b * (2)) were similarly performed by heating in an oven at 250 ° C for one hour in the heat resistance test and the color difference? Eab * And the heat resistance of the coating film was evaluated in the following four stages.

△ Eab * = √ ((L * (2) -L * (1)) 2 + (a * (2) -a * (1)) 2 + (b * (2) -b * (1)) 2 )

⊚: △ Eab * is less than 1.5

?: Eab * is not less than 1.5 and not more than 3.0

DELTA: Eab * was 3.0 or more and less than 5.0

X:? Eab * is 5.0 or more

&Lt; Evaluation of Solubility of Developer &

The obtained photosensitive coloring composition was coated on a 60 mm x 60 mm glass substrate to a film thickness of 3.0 m using a spin coater. Subsequently, the substrate was subjected to vacuum drying to obtain a test substrate. Four such substrates were prepared. Subsequently, the test substrate was dissolved in 50 g of a developer composed of 0.2 mass part of potassium hydroxide aqueous solution. The solution was allowed to stand, and the presence or absence of a precipitate after one day was confirmed. The solubility of the developer was evaluated based on the following criteria.

○: No sediment

X: with sediment

&Lt; Evaluation of re-solubility &

The obtained photosensitive coloring composition was coated on a 60 mm x 60 mm glass substrate to a film thickness of 3.0 m using a spin coater. Subsequently, the substrate was subjected to vacuum drying to obtain a test substrate. Four such substrates were prepared. Subsequently, the test substrate was dissolved in 50 g of propylene glycol monomethyl ether acetate (PGMAC). This was checked and the presence of sediment after one day was confirmed. Based on the following criteria, the re-solubility was evaluated.

○: No sediment

X: with sediment

division Photosensitive
Coloring composition Contrast Luminance Heat resistance Solvent Solubility Re-solubility Example 9 RP-1 4180 19.6 ◎ ○ ○ Example 10 RP-2 4250 19.6 ◎ ○ ○ Example 11 RP-3 4080 19.6 ◎ ○ ○ Example 12 RP-4 4350 19.6 ◎ ○ ○ Example 13 RP-5 4200 19.6 ◎ ○ ○ Example 14 RP-6 4260 19.5 ◎ ○ ○ Example 15 RP-7 4170 19.5 ◎ ○ ○ Example 16 RP-8 4120 19.6 ◎ ○ ○ Remark Example 2 RP-9 3680 19.3 ○ × ×

The present invention can improve the tinting strength by using a pigment derivative hybridized with a dye structure, and it has been confirmed that the redispersibility is remarkably improved due to introduction of a functional group excellent in water resistance.

Therefore, it is intended that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents. * * * * * Recently Added Patents .

Claims (12)

1. A pigment derivative represented by the following formula (1).
[Chemical Formula 1]

[In the above formula (1)
R ₁ to R ₃ are each independently of the other hydrogen, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, mono (C 1 -C 30) alkylamino, di Amino, di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;
A or B

,

,

,

,

,

(C1-C30) alkyl, (C6-C30) alkoxy, (C6-C30) aryl, mono Arylamino or di (C6-C30) arylamino;
R ₅ is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6-C30) aryl, (C6-C30) aralkyl (C1-C30) alkyl, ( C3-C30) heteroaryl, (C1-C30) alkylcarbonyl,
o is an integer from 1 to 3,
p is an integer of 1 to 2, and when o and p are 2 or more, R ₄ may be the same or different;
M is Na, H, K, or Li;
Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of R ₁ to R ₃ above; R ₄ is alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl; And the alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of A or B are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C1- , (C6-C30) aryl, (C3-C30) heteroaryl,
Wherein R ₄ is independently selected from the group consisting of (C 6 -C 30) aryl, mono (C 1 -C 30) alkylamino, di (C 1 -C 30) alkylamino, mono (C 6 -C 30) Arylamino, carboxylic acid group, sulfonyl, halogen, cyano, amino or nitro;
Of said R ₄ alkyl, aryl, aralkyl, monoalkylamino, dialkylamino, mono-arylamino and diarylamino represents a halogen, a carboxylic acid group, a sulfonyl, cyano, nitro, hydroxy, (C1-C30) alkyl , (C6-C30) aryl, (C3-C30) heteroaryl, and the like.
The method according to claim 1,
Wherein R ₁ to R ₃ are independently hydrogen or (C ₁ -C 30) alkyl, and the alkyl of R ₁ to R ₃ is Which may further be substituted with any one or more selected from halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C 1 -C 30) alkyl, (C 6 -C 30) aryl and (C 3 -C 30) Pigment derivative.
delete The method according to claim 1,
Wherein the formula (1) is represented by the following formula (2) or (3).
(2)

(3)

[In the above formulas (2) and (3)
R ₁ to R ₃ are independently of each other hydrogen or (C 1 -C 30) alkyl;
R ₁₁ and R ₁₄ are independently of each other hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 6 -C 30) aryl (C 1 -C 30) alkyl;
R ₁₂ and R ₁₃ independently from each other are hydrogen, (C 1 -C 30) alkyl or a carboxylic acid group;
The alkyl of R ₁ to R ₃ , the alkyl, aryl and aralkyl of R ₁₁ and R ₁₄ and the alkyl of R ₁₂ and R ₁₃ are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, C30) alkyl, (C6-C30) aryl and (C3-C30) heteroaryl.
The method according to claim 1,
Wherein the formula (1) is selected from the following compounds.

Reacting a compound represented by the formula (4) and a compound represented by the formula (5) to obtain a compound represented by the formula (6); And
And reacting the compound of formula (6) with the following formula (7) and (8) to prepare a pigment derivative represented by formula (1).

[Chemical Formula 1]

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)
AX
[Chemical Formula 8]
BX

[In the above formulas (1) and (4) to (8)
R ₁ to R ₃ are each independently of the other hydrogen, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, mono (C 1 -C 30) alkylamino, di Amino, di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;
A or B

,

,

,

,

,

(C1-C30) alkyl, (C6-C30) alkoxy, (C6-C30) aryl, mono Arylamino or di (C6-C30) arylamino;
R ₅ is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6-C30) aryl, (C6-C30) aralkyl (C1-C30) alkyl, ( C3-C30) heteroaryl, (C1-C30) alkylcarbonyl,
o is an integer from 1 to 3,
p is an integer of 1 to 2, and when o and p are 2 or more, R ₄ may be the same or different;
M is Na, H, K, or Li;
Each X is independently a leaving group;
Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of R ₁ to R ₃ above; R ₄ is alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl; And the alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of A or B are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C1- , (C6-C30) aryl, (C3-C30) heteroaryl,
Wherein R ₄ is independently selected from the group consisting of (C 6 -C 30) aryl, mono (C 1 -C 30) alkylamino, di (C 1 -C 30) alkylamino, mono (C 6 -C 30) Arylamino, carboxylic acid group, sulfonyl, halogen, cyano, amino or nitro;
Wherein said alkyl, aryl, aralkyl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of R ₄ is optionally substituted with at least one substituent selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, , (C6-C30) aryl, (C3-C30) heteroaryl, and the like.
delete A pigment composition comprising at least one pigment derivative and organic pigment according to any one of claims 1, 2 and 4 to 6.
9. The method of claim 8,
The organic pigments include pigments such as azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, quinophthalone pigments, diketopyrrolopyrrole pigments A pigment, an anthraquinone pigment, a thioindigo pigment, and a metal complex system pigment.
9. The method of claim 8,
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.
9. A color resist composition comprising the pigment composition of claim 8.
A color filter produced using the color resist composition of claim 11.