KR20100003606A - Quinophthalone derivatives and pigment dispersion compositions comprising the same - Google Patents

Abstract

PURPOSE: A quinophthalone derivative and a pigment dispersion composition containing the same are provided to ensure excellent storage stability and transparency. CONSTITUTION: A quinophthalone derivative is denoted by chemical formula 1. In the chemical formula 1, Q is quinophthalone residue, m is 1-4 integer number, X1 is NR'SO2, SO2NR', CONR', CH2NR', COCH2NR' or NR'CO; and X2 is C1-20 arylene, X3 is NR' or oxygen atom, and A and B independently NR1R2CnH2n+2NR1R2. A pigment composition contains quinophthalone derivative and pigment. The pigment color is yellow, red, or green. The pigment dispersion composition contains 0.1-50 weight% of pigment composition, 1-20 weight% of dispersing agent, 1-50 weight% of dispersion resin, and 40-90 weight% of organic solvent. The composition additionally contains surfantant or organic acid additive.

Description

QUINOPHTHALONE DERIVATIVES AND PIGMENT DISPERSION COMPOSITIONS COMPRISING THE SAME}

The present invention relates to a novel quinophthalone derivative and a pigment dispersion composition which is excellent in storage stability, transparency and color clarity prepared using the same, and at the same time has improved development residues.

The color filter manufacturing method includes a dyeing method, a pigment dispersion method, an electrodeposition method and a printing method, among which a pigment dispersion method having advantages in productivity, quality and cost is mainly used. In recent years, new technologies such as a film transfer method, an inkjet printing method, and a laser transfer method have been developed in order to improve color characteristics, reduce manufacturing costs, and respond to large area substrates for color purity and transmittance.

In general, color filters are manufactured by forming patterns of three primary colors, ie, red, green, and blue, on a glass substrate. When the pigment dispersion method is applied, such a pattern forming process is performed. Applying a color resist containing a pigment corresponding to each color pixel on a substrate, heat-drying the applied composition to form a film, and applying a mask having a desired shape on the formed film. And optionally developing after exposure, and heating and curing the developed film.

In particular, in the case of the color filter of the liquid crystal display device, since high transparency is required, it is very important to implement a color filter in which a very fine pigment is uniformly dispersed in the transparent vehicle. However, it is very difficult to stably disperse fine pigment particles in a transparent vehicle, which causes various problems in the physical properties of the final product. Specifically, in the case of the pigment dispersion composition in which the fine pigment is dispersed, the pigment particles may be gradually aggregated during the dispersing process or storage, and the viscosity may increase, and the storage stability may be reduced due to the strong thixotropy, thereby decreasing the luminance and color during the storage period. There is a problem that the sharpness is lowered. In addition, when manufacturing a color resist with such a pigment dispersion composition and applying it to a substrate, there is a problem that the color clarity required when manufacturing a color filter by forming a development residue by the interaction of the substrate and the pigment dispersion composition.

As a conventional technique for solving the above problems, a method of preparing a pigment dispersion composition using, for example, a sulfonated yellow pigment 138 (CI Pigment Yellow 138), or an alkali metal or an amine addition salt thereof, and the like is proposed. (See Japanese Patent Publication Nos. 2003-167112, 2001-335711, 2002-121457, and 2002-121418). However, although the sulfone compounds of the yellow pigment show an effect of improving the dispersion of the pigment, the interaction of the chromium surface and the sulfonate may cause a problem of developing residue after the production of the color resist. In the case of having only basic functional groups, it is difficult to stabilize the micronized pigment because the acid group bonding strength with the dispersant whose pigment affinity group is commonly used is amine is poor. In order to overcome this, pigment dispersion compositions containing amphoteric quinophthalone derivatives having both acidic and basic functional groups have been reported (Japanese Patent Laid-Open No. 2001-382998), but the improvement effect on dispersion stability is great but development There is no significant improvement in the problem of developing residue on the substrate afterwards.

It is an object of the present invention to provide novel quinophthalone derivatives which have excellent storage stability, transparency and color clarity and which can produce pigment dispersion compositions without developing residues in the production of color resists.

In addition, another object of the present invention is to provide a pigment dispersion composition comprising the quinophthalone derivative.

In accordance with the above object, the present invention provides a quinophthalone derivative of the general formula (1):

Where

Q is a quinophthalone moiety, m is an integer from 1 to 4, X ₁ is NR'SO ₂ , SO ₂ NR ', CONR', CH ₂ NR ', COCH ₂ NR' or NR'CO, X ₂ is C _1-20 arylene, X ₃ is NR ′ or an oxygen atom, A and B are each independently —NR ₁ R ₂ C _n H _{2n + 2} NR ₁ R ₂ , and R ′, R ₁ and R ₂ are Each independently represent a hydrogen atom, a C _1-10 alkyl group or a phenyl group, n is an integer of 1 to 10;

The present invention also provides a pigment composition comprising a quinophthalone derivative (hereinafter referred to as the compound of formula 1) and a pigment.

Here, the compound of Formula 1 preferably contains 0.1 to 50 parts by weight based on 100 parts by weight of the pigment.

It is also preferred that the pigment is selected from the group consisting of yellow, red and green.

Here, the yellow pigment is C.I. Pigment Orange 38, C.I. Pigment Orange 71, Pigment Yellow 83, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 183 and C.I. Pigment yellow 185; Red pigment is C.I. Pigment Red 122, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 202, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment red 272; Green pigment is C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. It is preferably selected from the group consisting of pigment green 58.

The present invention also provides a pigment dispersion composition comprising a pigment composition, a dispersant, a resin for dispersion and an organic solvent.

Here, based on the total weight of the pigment dispersion composition, the pigment composition is 0.1 to 50% by weight; Dispersant 1 to 20% by weight; Dispersion resin is 1 to 50% by weight; And it is preferred to include 40 to 90% by weight of the organic solvent.

Wherein the dispersant is selected from the group consisting of acrylic block copolymers, polyurethanes and polyethylamines; The resin for dispersion is a polymer containing a monomer having a carboxyl group as a repeating unit, has a weight average molecular weight of 5,000 to 100,000, and has an acid value of 50 to 150; The organic solvent is preferably selected from the group consisting of alkylene glycol monoalkyl ethers and their acetate esters, ketones, and alcohols.

The present invention also provides a pigment dispersion composition further comprising an additive selected from the group consisting of a surfactant and an organic acid in the pigment dispersion composition.

The present invention also provides a color resist comprising the pigment dispersion composition.

The pigment dispersion composition obtained by the present invention has excellent transparency, contrast, storage stability, and can be usefully used for preparing pigment dispersion color resists and high-quality inks because it exhibits an improved development residue effect when producing color resists.

The compound of formula 1 according to the present invention is a pigment derivative having a structure in which a sulfone group and a triazine group are bonded to a quinophthalone structure, wherein a triazine group, which is a basic functional group, is further bonded by a specific linking group.

The compound of Formula 1 according to the present invention has both an acidic functional group and a basic functional group as a substituent in the mother nucleus having affinity with the organic pigment as described above, so that the acidic functional group of the pigment derivative is combined with the basic functional group of the dispersant to improve stability. Maximized and basic functional groups are combined with the dispersing resin to eliminate developing residues during development after color resist preparation.

The compound of Formula 1 may be prepared by reacting a quinophthalone pigment with chlorosulfonic acid followed by reaction with a triazine derivative.

The chlorosulfonic acid reaction can, for example, use an organic solvent and react with a quinophthalone pigment and chlorosulfonic acid in a 1 to 10 molar ratio therewith at a temperature of -10 to 150 ° C. Moreover, you may add cyanyl chloride and a phosphorus hydroxy halogenating agent. The number of m in the compound of Formula 1 may be appropriately selected depending on the amount of chlorosulfonic acid and the reaction temperature. The reaction between the reaction product and the triazine derivative obtained here can be carried out, for example, at a temperature of 0 to 150 ° C in an aqueous NaCl solution or an organic solvent.

The compound of Formula 1 may be used in the pigment composition of the present invention, based on 100 parts by weight of 0.1 to 50 parts by weight, preferably 1 to 30 parts by weight.

As the pigment used in the pigment composition of the present invention, a yellow, red or green pigment known to those skilled in the art may be used, and a green pigment may be further added thereto.

The yellow pigment is C.I. Pigment Orange 38, C.I. Pigment Orange 71, Pigment Yellow 83, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 183 and C.I. One or more selected from the group consisting of Pigment Yellow 185 can be used; As the red pigment, C.I. Pigment Red 122, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 202, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. One or more selected from the group consisting of Pigment Red 272 can be used; As the green pigment, C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. One or more selected from the group consisting of pigment green 58 may be used.

The pigment composition comprising the compound of Formula 1 and the pigment of the present invention is mixed with a conventional dispersant, a resin for dispersing, an organic solvent and other additives to provide a pigment dispersion composition, comprising the compound of Formula 1 and the pigment of the present invention The pigment composition may be included in 0.1 to 50% by weight, preferably 1 to 30% by weight based on the total weight of the pigment dispersion composition, wherein, if the content of the pigment composition exceeds 50% by weight pigment dispersion The viscosity stability of the composition may be lowered.

The dispersant used in the composition of the present invention may be an acrylic block copolymer, polyurethane, polyethylamine or mixtures thereof, and is characterized by including an amine group as a pigment affinity group.

Such dispersants may be commercially available, and representative examples thereof include disperbyk-160, dispervic-161, dispervic-165, and dispervic-168, which are commercially available from BYK-Chemie. Dispervic-170, Dispervic-171, Dispervic-2000 and Dispervic-2001, EFKA-4046, EFKA-4047 and EFKA-4340 from EFKA, Solsperse-24000 and Solsperth from Avecia And PB-821, PB-822, PB-824 and PB-827 from AJINOMOTO, each of which may be used alone or in combination of two or more thereof.

The dispersant may be included in 1 to 20% by weight, preferably 1 to 10% by weight based on the total weight of the pigment dispersion composition of the present invention. At this time, when the content of the dispersant exceeds 20% by weight, the storage stability of the pigment dispersion composition is excellent, but when the pigment dispersion color resist is prepared, the development speed for the alkaline developer may be slowed, and thus a residue may remain after development. Is preferably used in the minimum amount necessary for dispersion and dispersion stability of the organic pigment.

The dispersion resin may be a polymer including a monomer having a carboxyl group as a repeating unit, and representative examples of the monomer may include acrylic acid, methacrylic acid, maleic acid, and fumaric acid having one or more carboxyl groups in a molecule. . In addition, the monomers may be used alone or in combination of two or more as a compound having a carbon-carbon unsaturated bond, and representative examples of such a dispersion resin include aromatic vinyl compounds such as styrene and vinyltoluene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, benzyl meta Methacrylate methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate and Unsaturated carboxylate compounds such as benzyl methacrylate; Unsaturated aminoalkyl carboxylate compounds such as aminoethyl acrylate; And vinyl carboxylate compounds such as vinyl acetate and vinyl propionate.

The resin for dispersion used in the pigment dispersion composition of the present invention preferably has a weight average molecular weight of 5,000 to 100,000 and an acid value of 50 to 150, wherein when the acid value of the resin for dispersion exceeds 150, the storage stability of the pigment dispersion composition If it is lower than 50, the developing speed for the alkaline developer may be slow. The acid value of such a resin for dispersion can be adjusted by the molar ratio of the monomer which comprises resin.

The resin for dispersion may be included in 1 to 50% by weight based on the total weight of the pigment dispersion composition of the present invention, preferably 1 to 10% by weight.

As the organic solvent used in the pigment dispersion composition of the present invention, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether and ethylene glycol Alkylene glycol monoalkyl ethers such as monoethyl ether and acetates thereof; Ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone; And alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, and glycerin. These may be used alone or in combination of two or more.

The amount of the organic solvent may be 40 to 90% by weight, preferably 60 to 80% by weight based on the total weight of the pigment dispersion composition of the present invention.

In addition, the pigment dispersion composition of the present invention may further include a conventional surfactant or organic acid as an additive to improve the dispersion stability, thermal stability and alkali developability of the pigment.

The pigment dispersion composition of the present invention may be prepared through a wet dispersion stabilization process of wetting the pigment powder while mixing the components in an appropriate amount and then mixing with a stirrer, and the pigment in the composition thus prepared is 20 to 150 nm It will have an average particle size. At this time, in consideration of the efficiency of pigment dispersion, in order to maximize the physical impact force bead (beads) of 0.05 to 2.0mm diameter (beads) may be used, such beads may be of 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.

Since the pigment particles dispersed in the composition of the present invention are thermodynamically unstable, they tend to agglomerate in a direction to reduce specific surface area, particularly in the case of ultra-fine particles that are excessively dispersed during the dispersion process. Compound of the formula (1) of the present invention inhibits the aggregation of such pigment particles to improve the transparency and to improve the developability by increasing the acid base bond with the resin for dispersion.

The pigment dispersion composition of the present invention can also be used as a coating material, a printing ink, or the like, and can also be applied as a pigment dispersion color resist capable of forming an image by light irradiation by mixing with a photosensitive composition. Such pigment-containing color resists may generally comprise a pigment dispersion composition of the present invention, a polyfunctional monomer having two or more unsaturated double bonds, and a photopolymerization initiator, and because of containing the pigment dispersion composition of the present invention, transmittance and color Not only is it clear, it also has excellent storage stability.

Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are merely to illustrate the invention, the scope of the present invention is not limited to the following examples.

Preparation Example 1 Preparation of Quinophthalone Derivative A

Step 1

C.I. 50 g of Pigment Yellow 138 and 500 g of chlorosulfonic acid were slowly added with stirring at 10 to 20 ° C, followed by stirring at 90 ° C for 1 hour. 90 g of thionyl chloride was added to the obtained reaction product, stirred at 90 ° C. for 3 hours, cooled to room temperature, and 10 L of ice water was slowly added while maintaining the temperature at 10 ° C. or lower to obtain a precipitate. The resulting precipitate was slurried with 3 L of ice water, and then 20 g of 1,4-phenylenediamine was added thereto, stirred at 5 ° C. for 3 hours, and then stirred at 50 ° C. for 1 hour. The reaction product was filtered, washed with water and dried to afford 70 g of the title compound (yield 90%).

Elemental Analysis Value (C ₃₃ H ₁₃ Cl ₈ N ₃ O ₉ S ₂ )

C H Cl N O S Calculation 42.02 1.39 30.07 4.45 15.27 6.80 Measure 42.24 1.19 28.07 6.45 15.20 6.87

Step 2

After dissolving 11 g of cyanuric chloride in 160 g of dimethylacetamide, 10 g of N, N-dimethylethylenediamine was slowly added, followed by stirring at 5 ° C. for 3 hours. 5 g of triethylamine was added thereto, and after heating the temperature to 70 ° C., 10 g of the material obtained in Step 1 was dissolved in 160 g of dimethylacetamide, and then slowly added thereto, followed by stirring for 4 hours. After the reaction, the mixture was cooled and added to 3 L of water. The precipitate formed was filtered and the filtered solid was washed with water to obtain 25 g of a compound (yield: 64%).

Elemental Analysis Value (C ₄₄ H ₃₄ Cl ₈ N ₁₀ O ₉ S ₂ )

C H Cl N O S Calculation 42.0 3.07 23.53 11.94 12.05 5.37 Measure 44.24 2.87 23.74 11.73 12.05 5.37

Preparation Example 2 Preparation of Quinophthalone Derivative B

Step 1

C.I. 50 g of Pigment Yellow 138 was slowly added to 500 g of chlorosulfonic acid with stirring at 10 to 20 ° C, followed by stirring at 90 ° C for 1 hour. 90 g of thionyl chloride was added to the obtained reaction product, stirred at 90 ° C. for 3 hours, and then cooled to room temperature. 10 L of ice water was slowly added while keeping the temperature below 10 ° C. to obtain a precipitate. The resulting precipitate was slurried with 3 L of ice water, and then 10 g of p-phenylenediamine was added thereto, stirred at 5 ° C. for 3 hours, and then stirred at 50 ° C. for 1 hour. The reaction product was filtered, washed with water and dried to give 65 g of compound (yield 81%).

Elemental Analysis Value (C ₄₀ H ₁₉ Cl ₈ N ₃ O ₉ S ₂ )

C H Cl N O S Calculation 46.49 1.85 27.45 4.07 13.93 6.21 Measure 46.43 1.91 27.33 4.19 13.72 6.42

Step 2

After dissolving 11 g of cyanuric chloride in 160 g of dimethylacetamide, 10 g of N, N-dimethylethylenediamine was slowly added, followed by stirring at 5 ° C. for 3 hours. 5 g of triethylamine was added thereto, and after heating the temperature to 70 ° C., 10 g of the material obtained in Step 1 was dissolved in 160 g of dimethylacetamide, and slowly added thereto, followed by stirring for 4 hours. After the reaction, the mixture was cooled and added to 3 L of water. The precipitate formed was filtered and the filtered solid was washed with water to obtain 25 g of a compound (yield: 64%).

Elemental Analysis Value (C ₅₁ H ₃₉ Cl ₈ N ₉ O ₉ S ₂ )

C H Cl N O S Calculation 48.24 30.10 22.34 9.93 11.34 5.05 Measure 48.00 30.34 22.40 9.86 11.11 5.28

Comparative Production Example 1: Preparation of Quinophthalone Derivative C

Into a 500 mL four-necked flask, 450 g of 101% sulfuric acid prepared from 25% fuming sulfuric acid and sulfuric acid was added, followed by C.I. 45 g of Pigment Yellow 138 was added in portions. The mixture was stirred at 80 ° C. for 3 hours, and the sulfonate was precipitated while stirring the reaction solution in 5000 parts of ice water. The precipitated sulfonate was separated by filtration, washed with 2 L of 0.1% hydrochloric acid, and further washed with 2 L of purified water to obtain a sulfonated pigment (43 g).

Elemental Analysis Value (C ₂₇ H ₇ Cl ₈ NO ₇ S)

C H Cl N O S Calculation 41.95 0.91 36.69 1.81 14.49 4.15 Measure 41.90 0.96 36.63 1.74 14.40 4.06

Comparative Preparation Example 2 Preparation of Quinophthalone Derivative D

Into a 500 mL four-necked flask, 450 g of 101% sulfuric acid prepared from 25% fuming sulfuric acid and sulfuric acid was added, followed by C.I. 45 g of Pigment Yellow 138 was added in portions. The mixture was stirred at 80 ° C. for 3 hours, and the sulfonate was deposited while stirring the reaction solution in 5000 parts of ice water. The precipitated sulfonate was separated by filtration, washed with 2 L of 0.1% hydrochloric acid, and further washed with 2 L of purified water to obtain a sulfonated pigment. The resulting sulfonate paste was redispersed in 5 L of water and the pH value was adjusted to 11.5 while stirring the 10% aqueous NaOH solution. The resulting solution was further heated to 60 ° C., and an aqueous solution of 36 g of amine acetate (ceo-acetamine 24 manufactured by Kaobu Co., Ltd.) was added dropwise thereto, and the resulting precipitate was separated by filtration, washed with plenty of water, and dried at 80 ° C. 35g of aluminum salt of quinoline derivative was obtained.

Elemental Analysis Value (C ₄₂ H ₄₀ Cl ₈ N ₂ O ₇ S)

C H Cl N O S Calculation 50.42 4.03 28.35 2.80 11.19 3.21 Measure 50.12 4.33 28.11 3.04 11.12 3.28

Comparative Production Example 3: Preparation of Quinophthalone Derivative E

Into a 500 mL four-necked flask, 450 g of 101% sulfuric acid prepared from 25% fuming sulfuric acid and sulfuric acid was added, followed by C.I. 45 g of Pigment Yellow 138 was added in portions. The mixture was stirred at 80 ° C. for 3 hours, and the sulfonate was deposited while stirring the reaction solution in 5000 parts of ice water. The precipitated sulfonate was separated by filtration, washed with 2 L of 0.1% hydrochloric acid, and further washed with 2 L of purified water to obtain a sulfonated pigment. The resulting sulfonate paste was redispersed in 5 L of water and the pH value was adjusted to 11.5 while stirring the 10% aqueous NaOH solution. The resulting solution was further heated to 60 ° C., an aqueous solution of 47 g of aluminum chloride (hexahydrate) was added dropwise, the resulting precipitate was separated by filtration, washed with a large amount of water, dried at 80 ° C., and an aluminum salt of 38 g of quinoline derivatives. Got.

Examples 1-8, and Comparative Examples 1-12: Preparation of Pigment Dispersion Compositions

15 g of pigments (C.I. Pigment Yellow 138, C.I. Pigment Yellow 150, C.I. Pigment Green 36 and C.I. Pigment Red 254); 3 g of quinophthalone derivatives (quinophthalone derivatives A, B, C, D and E); BYK-2000 5g (40% solids); 3 g of resin for dispersion (30% solids, copolymerization ratio of acrylic acid / methacrylic acid / ethyl methacrylate / benzyl methacrylate copolymer = 10/30/20/40, weight average molecular weight 10,000); And 100g of 0.5mm zirconia in 74g of propylene glycol monoethyl ether was dispersed for 5 hours in a paint shaker to obtain a pigment dispersion composition. Specific compositions are shown in Table 1 below.

Evaluation of Examples and Comparative Examples

Each composition was evaluated using the pattern formed in the Example and the comparative example.

Contrast

The pigment dispersion compositions obtained in Examples 1 to 8 and Comparative Examples 1 to 12 were respectively mixed with the same amount of acrylic resin and sufficiently stirred to obtain a resin mixture. It was sprayed with a spin coater and dried in an oven at 80 ° C. for 10 minutes to form a coating film. For each film, (x, y, Y) was measured in a C light source using a colorimeter MCPD-3000 (Otsuka Co., Ltd.). It was. In addition, using the luminance meter LS-100 (Minolta Co., Ltd.) and a polarizer for each film, the minimum and maximum luminance values were measured, and a contrast value (maximum luminance value / minimum luminance value) was calculated based on the results. Is shown in Table 1 below

Storage stability

The compositions prepared in Examples 1 to 8 and Comparative Examples 1 to 12 were measured for an initial viscosity at 60 rpm using LDVE II manufactured by Brookfield. After putting into a low temperature incubator maintained at 45 ℃ two weeks after the viscosity was measured to determine the viscosity change over time. In general, if the viscosity change within 10% for two weeks it can be said to have excellent storage stability.

phenomenon Residue

The pigment dispersion compositions obtained in Comparative Examples 1 to 12 were mixed with the same amount of acrylic resin on a glass substrate coated with a chromium substrate and a resin black matrix, respectively, and sufficiently stirred to obtain a resin mixture. After spraying it with a spin coater, it was dried in an oven at 80 ° C. for 10 minutes to form a coating film. After developing in 1% aqueous KOH solution for 1 minute, the substrate state was measured by atomic force microscope (AFM) (marked with ◎ when Ra is 4 or less). , 4 to 8, △, 8 or more cases are represented by X).

From the results of Table 1, it can be seen that in the case of Examples 1 to 8 to which the compound according to the present invention is added, it is more excellent in storage stability and development residues, etc. than Comparative Examples 1 to 12.

Claims (12)

Quinophthalone derivatives characterized in that represented by the following formula (1): <Formula 1>

Where Q is a quinophthalone moiety, m is an integer from 1 to 4, X ₁ is NR'SO ₂ , SO ₂ NR ', CONR', CH ₂ NR ', COCH ₂ NR' or NR'CO, X ₂ is C _{1 - 20} arylene, X ₃ is NR 'or an oxygen atom, a and B are each independently selected from -NR ₁ R ₂ C _n and _{H 2n +2 NR 1 R 2,} R', R 1 and R ₂ are Each independently represents a hydrogen atom, a C _1-10 alkyl group or a phenyl group, n is an integer of 1 to 10; A pigment composition comprising the quinophthalone derivative of claim 1 and a pigment. The method of claim 2, A pigment composition comprising 0.1 to 50 parts by weight based on 100 parts by weight of the quinophthalone derivative. The method of claim 2, Pigment composition, characterized in that at least one pigment selected from the group consisting of yellow, red, and green. The method of claim 4, wherein Yellow pigment is C.I. Pigment Orange 38, C.I. Pigment Orange 71, Pigment Yellow 83, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 183 and C.I. At least one selected from the group consisting of Pigment Yellow 185; Red pigment is C.I. Pigment Red 122, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 202, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. At least one selected from the group consisting of Pigment Red 272; Green pigment is C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment green, characterized in that at least one selected from the group consisting of 58. A pigment dispersion composition comprising the pigment composition of claim 2, a dispersant, a resin for dispersing, and an organic solvent. The method of claim 6, Based on the total weight of the pigment dispersion composition a) 0.1 to 50% by weight of the pigment composition of claim 2; b) 1 to 20 weight percent dispersant; c) 1 to 50% by weight of resin for dispersion; And d) 40 to 90% by weight of organic solvent Pigment dispersion composition comprising a. The method of claim 6, Pigment dispersion composition, characterized in that the dispersing agent is at least one selected from the group consisting of acrylic block copolymers, polyurethanes and polyethylamines. The method of claim 6, The resin for dispersion is a polymer comprising a monomer having a carboxyl group as a repeating unit, has a weight average molecular weight of 5,000 to 100,000, and has an acid value of 50 to 150. The method of claim 6, Pigment dispersion composition, characterized in that the organic solvent is at least one selected from the group consisting of alkylene glycol monoalkyl ether and their acetate esters, ketones, and alcohols. The method of claim 6, Pigment dispersion composition, characterized in that it further comprises at least one additive selected from the group consisting of surfactants and organic acids. A color resist comprising the pigment dispersion composition of claim 6.