KR20140122470A - Dye-hybridized pigment derivatives, pigment dispersion composition, photo-sensitive color composition, and color filter - Google Patents

Dye-hybridized pigment derivatives, pigment dispersion composition, photo-sensitive color composition, and color filter Download PDF

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KR20140122470A
KR20140122470A KR1020130039190A KR20130039190A KR20140122470A KR 20140122470 A KR20140122470 A KR 20140122470A KR 1020130039190 A KR1020130039190 A KR 1020130039190A KR 20130039190 A KR20130039190 A KR 20130039190A KR 20140122470 A KR20140122470 A KR 20140122470A
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Prior art keywords
derivative
pigment
carbon atoms
group
substituted
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KR1020130039190A
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Korean (ko)
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조규오
박상준
천호영
조용수
한명식
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주식회사 알파켐
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Publication of KR20140122470A publication Critical patent/KR20140122470A/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors

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 >

Figure pat00080

Description

DYE-HYBRIDIZED PIGMENT DERIVATIVES, PIGMENT DISPERSION COMPOSITION, PHOTO-SENSITIVE COLOR COMPOSITION, AND COLOR FILTER, 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. On the other hand, the dye-type color filter which does not require dispersion process has high transparency and contrast characteristics because there is little effect of particle scattering by 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 >

Figure pat00001

(Wherein Q represents an organic dye residue,

X 1 is a group selected from - (CH 2 ) n -, -NR'SO 2 -, -SO 2 NR'-, -CONR'-, -CH 2 NR'COCH 2 NR'- and -NR'CO- N is selected within the range of 1 to 10,

X 2 is at least one group selected from an arylene group having up to 20 carbon atoms, a substituted arylene group having up to 20 carbon atoms, a heteroaromatic ring having up to 20 carbon atoms and a substituted heteroaromatic ring having up to 20 carbon atoms or selected from these arylene groups and heteroaromatic rings and -NR'-, -O-, -SO 2 - and -CO- 2 a (divalent) connection (connecting group) refers to at least two groups bonded to each other selected from ,

X 3 represents -NR'-, -NR'SO 2 -, -SO 2 NR'- or -O-,

E is selected from an aryl group having up to 40 carbon atoms, a substituted aryl group having up to 40 carbon atoms, a heteroaromatic ring having up to 40 carbon atoms and a substituted heteroaromatic ring having up to 40 carbon atoms,

R1, R2 and R3 each independently represent a hydrogen atom, a halogen atom, an amine group, a cyano group, a nitro group, an alkyl group having 20 or less carbon atoms, a substituted alkyl group having 20 or less carbon atoms, A substituted or unsubstituted heteroaliphatic ring, an alkenyl group having up to 20 carbon atoms, a substituted alkenyl group having up to 20 carbon atoms, and an aryl group having 20 or fewer carbon atoms, or a substituted Aryl groups,

t is 1 or 2,

Wherein each R 'is independently a hydrogen atom, an alkyl group having up to 20 carbon atoms, a substituted alkyl group having up to 20 carbon atoms, an alkenyl group having up to 20 carbon atoms, a substituted alkane having up to 20 carbon atoms An aryl group having up to 20 carbon atoms, or a substituted aryl group having up to 20 carbon atoms.

In Formula 1, E may be a pigment derivative selected from the following Formulas (1A) to (1S).

Figure pat00002

Wherein R 1 is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 hydroxyalkyl, C 1 -C 12 cyanoalkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl,

Y 1 is nitro, cyano, trifluoromethyl, carboxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 acylamino or halogen,

Y 2 and Y 3 are each independently of the other hydrogen, nitro, cyano or halogen,

Y < 4 > is hydrogen, nitro, cyano or halogen,

Y 5 and Y 6 are each independently of the other hydrogen, nitro, cyano or halogen,

Y 7 is chlorine or -CONH 2 ,

Y 8 is chlorine, bromine, C 1 -C 12 alkyl or C 1 -C 12 alkoxy,

Y 9 is cyano, nitro or C 1 -C 12 alkoxycarbonyl,

Y 10 is hydrogen, bromine, chlorine, C 1 -C 12 alkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl,

Y 11 is hydrogen, cyano, nitro or -COR 1 , wherein R 1 is as defined above,

Y 12 , Y 13 and Y 14 are each independently hydrogen, bromine, chlorine, cyano, nitro or trifluoromethyl.

The organic dye residue may be an anthraquinone dye, a dianthraquinone dye (including Red 177), a diketopyrrolopyrrol dye (Orange 71, Orange 73, Red 254, Red 255, Red 264, Red 272) And a naphthalone system (including Yellow 138).

The present invention also provides a pigment dispersion composition comprising the pigment derivative and the organic pigment.

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

The present invention also provides a color filter characterized in that a pixel is formed using the color resist composition.

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 >

Figure pat00003

In the above formula, Q represents an organic dye residue and may have an organic pigment structure described later.

X 1 is a group selected from - (CH 2 ) n -, -NR'SO 2 -, -SO 2 NR'-, -CONR'-, -CH 2 NR'COCH 2 NR'- and -NR'CO- N is selected within the range of 1 to 10,

X 2 is at least one group selected from an arylene group having up to 20 carbon atoms, a substituted arylene group having up to 20 carbon atoms, a heteroaromatic ring having up to 20 carbon atoms and a substituted heteroaromatic ring having up to 20 carbon atoms or selected from these arylene groups and heteroaromatic rings and -NR'-, -O-, -SO 2 - and -CO- 2 a (divalent) connection (connecting group) refers to at least two groups bonded to each other selected from ,

X 3 represents -NR'-, -NR'SO 2 -, -SO 2 NR'- or -O-,

E is selected from an aryl group having up to 40 carbon atoms, a substituted aryl group having up to 40 carbon atoms, a heteroaromatic ring having up to 40 carbon atoms and a substituted heteroaromatic ring having up to 40 carbon atoms,

R1, R2 and R3 each independently represent a hydrogen atom, a halogen atom, an amine group, a cyano group, a nitro group, an alkyl group having 20 or less carbon atoms, a substituted alkyl group having 20 or less carbon atoms, A substituted or unsubstituted heteroaliphatic ring, an alkenyl group having up to 20 carbon atoms, a substituted alkenyl group having up to 20 carbon atoms, and an aryl group having 20 or fewer carbon atoms, or a substituted Aryl groups,

t is 1 or 2,

Wherein each R 'is independently a hydrogen atom, an alkyl group having up to 20 carbon atoms, a substituted alkyl group having up to 20 carbon atoms, an alkenyl group having up to 20 carbon atoms, a substituted alkane having up to 20 carbon atoms An aryl group having 20 or fewer carbon atoms, or a substituted aryl group having 20 or fewer carbon atoms.

In yet another embodiment,

E in the formula (1) may be selected from the following formulas (1A) to (1S).

Figure pat00004

Wherein R 1 is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 hydroxyalkyl, C 1 -C 12 cyanoalkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl,

Y 1 is nitro, cyano, trifluoromethyl, carboxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 acylamino or halogen,

Y 2 and Y 3 are each independently of the other hydrogen, nitro, cyano or halogen,

Y &lt; 4 &gt; is hydrogen, nitro, cyano or halogen,

Y 5 and Y 6 are each independently of the other hydrogen, nitro, cyano or halogen,

Y 7 is chlorine or -CONH 2 ,

Y 8 is chlorine, bromine, C 1 -C 12 alkyl or C 1 -C 12 alkoxy,

Y 9 is cyano, nitro or C 1 -C 12 alkoxycarbonyl,

Y 10 is hydrogen, bromine, chlorine, C 1 -C 12 alkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl,

Y 11 is hydrogen, cyano, nitro or -COR 1 , wherein R 1 is as defined above,

Y 12 , Y 13 and Y 14 are each independently hydrogen, bromine, chlorine, cyano, nitro or trifluoromethyl.

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)

Figure pat00005

The derivative (D-2)

Figure pat00006

The derivative (D-3)

Figure pat00007

The derivative (D-4)

Figure pat00008

The derivative (D-5)

Figure pat00009

The derivative (D-6)

Figure pat00010

The derivative (D-7)

Figure pat00011

The derivative (D-8)

Figure pat00012

The derivative (D-9)

Figure pat00013

The derivative (D-10)

Figure pat00014

The derivative (D-11)

Figure pat00015

The derivative (D-12)

Figure pat00016

The derivative (D-13)

Figure pat00017

The derivative (D-14)

Figure pat00018

The derivative (D-15)

Figure pat00019

The derivative (D-16)

Figure pat00020

The derivative (D-17)

Figure pat00021

The derivative (D-18)

Figure pat00022

The derivative (D-19)

Figure pat00023

The derivative (D-20)

Figure pat00024

The derivative (D-21)

Figure pat00025

The derivative (D-22)

Figure pat00026

The derivative (D-23)

Figure pat00027

The derivative (D-24)

Figure pat00028

The derivative (D-25)

Figure pat00029

The derivative (D-26)

Figure pat00030

The derivative (D-27)

Figure pat00031

The derivative (D-28)

Figure pat00032

The derivative (D-29)

Figure pat00033

The derivative (D-30)

Figure pat00034

The derivative (D-31)

Figure pat00035

The derivative (D-32)

Figure pat00036

The derivative (D-33)

Figure pat00037

The derivative (D-34)

Figure pat00038

The derivative (D-35)

Figure pat00039

The derivative (D-36)

Figure pat00040

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 pigment include pigments such as azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments ( isoindoline 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 EFKA 4046 (trade name, manufactured by EFKA), PB-821 (manufactured by Ajinomoto Fine Techno), DISPERBIK 160, 161, 162, 242, 18000 (trade name) of Avecia Limited, SOLSPERSE 22000, 24000, 28000 (trade name) of Avecia Limited, DISPARLON DA-234, 325, 375, ), But the present invention is 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 method of the pigment include a salt-milling method in which milling is carried out in the presence of a common salt (see, for example, Japanese Unexamined Patent Publication No. 2001-220520 and Japanese Unexamined Patent Application Publication No. 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, isophthalo phenone-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.

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) >

35 g of Red 255 pigment was gradually added to 117 g of chlorosulfonic acid with stirring at 10 to 20 占 폚.

After completion of the addition, the mixture was stirred for 1 hour at 40-50 &lt; 0 &gt; C. Then 90 g thionyl chloride was added and the resulting mixture was stirred at this temperature for 3 hours. The reaction mixture was cooled to room temperature, and 5 liters of ice water was gradually poured while maintaining the temperature below 10 DEG C to form a precipitate. The precipitate was filtered and washed with ice water to obtain the chlorosulfonated product (water-containing cake) of the diketopyrrolopyrrole derivative A. The chlorosulfonated product was slurried in 1.5 liters of ice water, 16 g of 3,5-phenylenediamine was added, and the mixture was stirred at 50 &lt; 0 &gt; C for 3 h then 5 &lt; 0 &gt; C. After the stirring was completed, filtration, washing with water and drying were carried out to obtain 40 g (70%) of the following intermediate A.

The thus obtained intermediate A was reacted with 160 g of 1,4-dioxane at a temperature of 60 DEG C or lower and a compound obtained by the coupling reaction of 3-amino-6-nitrobenzoisothiazole and N- (4-aminophenyl) maleimide 158 g of a mixed solution was gradually added and stirred for 4 hours. The reaction mixture was cooled to room temperature and then poured into 2.5 liters of water to form a precipitate. The precipitate was filtered, washed with water and dried to obtain 109 g (78%) of the pigment-dye hybrid derivative (D-1) of the formula (2).

(2)

Figure pat00041

Production Examples 2 to 36

The above-mentioned derivatives D-2 to D-36 were prepared in a manner similar to that described in Preparation Example 1.

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. , &Quot; ARONIX M110 &quot;) 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-based red pigment CI Pigment Red 254 ("IRGAZIN RED 2030" manufactured by CiJa · pan), 1400 parts of sodium chloride and 350 parts of diethylene glycol were mixed in a stainless steel first gallon kneader (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.

Reference Example 3 <Preparation of red-treated pigment 2 (RK-2)

Except that an anthraquinone-based red pigment CI Pigment Red 177 ("Cromophtal Red A3B" manufactured by Ciba Japan Ltd.) was used in place of the CI Pigment Red 254, and each step was performed under the same conditions as the finely divided pigment 1 (RK-1) To obtain 190 parts of an anthraquinone-based atomized pigment 2 (RK-2).

Reference Production Example 4 <Preparation of red-treated pigment 3 (RK-3)

Each step was carried out under the same conditions as the finely divided pigment 1 (RK-1), except that perylene-based red pigment CI Pigment Red 179 ("Paliogen Maroon L 3920" manufactured by Basf) was used instead of CI Pigment Red 254 Thus, 190 parts of perylene-based atomized pigment 3 (RK-3) was obtained.

[Example 1]

(Pigment dispersion composition (RD-1))

The following mixture was stirred and mixed, and then dispersed with Eigermill ("mini model M-250 MKII" manufactured by Eiger Japan) for 4 hours using zirconia beads having a diameter of 0.2 mm and then filtered with a filter of 6.0 μm , And a non-volatile component of 20 wt% was prepared.

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 9]

The pigment dispersion compositions (RD-2 to RD-9) 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 composition shown in Table 1 .

[Example 10]

(Pigment dispersion composition (RD-10))

The following mixture was stirred and mixed, and then dispersed with Eigermill ("mini model M-250 MKII" manufactured by Eiger Japan) for 4 hours using zirconia beads having a diameter of 0.2 mm and then filtered with a filter of 6.0 μm , And a non-volatile component of 20 wt% was prepared.

Atomized pigment 2 (RK-2): 11.3 parts

(C.I. Pigment Red 177)

Acrylic resin solution 1: 21.2 parts

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

Dye derivative (derivative (D-19)): 0.5 part

Propylene glycol monomethyl ether acetate (PGMAC): 58.8 parts

[Examples 11 to 18]

The pigment dispersion compositions (RD-11 to RD-18) were prepared in the same manner as in the pigment dispersion composition (RD-10) except that the pigment, the resinous dispersant and the derivative were changed to the composition shown in Table 1.

[Example 19]

(Pigment Dispersion Composition (RD-19))

The following mixture was stirred and mixed, and then dispersed with Eigermill ("mini model M-250 MKII" manufactured by Eiger Japan) for 4 hours using zirconia beads having a diameter of 0.2 mm and then filtered with a filter of 6.0 μm (RD-19) having a non-volatile component of 20 wt% was prepared.

Atomized pigment 3 (RK-3): 11.3 parts

(C.I. Pigment Red 179)

Acrylic resin solution 1: 21.2 parts

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

Dye derivative (derivative (A-19)): 0.5 part

Propylene glycol monomethyl ether acetate (PGMAC): 58.8 parts

[Examples 20 to 27]

The pigment dispersion compositions (RD-20 to 27) were prepared in the same manner as in the pigment dispersion composition (RD-19) except that the pigment, the resinous dispersant and the derivative were changed to the compositions shown in Table 1.

[Comparative Example 1]

The pigment dispersion composition (D-28) 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 composition shown in Table 1.

[Comparative Example 2]

The pigment dispersion composition (D-29) was prepared in the same manner as in the pigment dispersion composition (RD-10) except that the pigment, the resinous dispersant and the derivative were changed to the composition shown in Table 1.

[Comparative Example 3]

The pigment dispersion composition (D-30) was prepared in the same manner as in the pigment dispersion composition (RD-19) except that the pigment, the resinous dispersant and the derivative were changed to the composition 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 Example 9 RD-9 11.3 D-9 0.5 8.2 21.2 58.8 Example 10 RD-10 RK-2 11.3 D-19 0.5 8.2 21.2 58.8 Example 11 RD-11 11.3 D-20 0.5 8.2 21.2 58.8 Example 12 RD-12 11.3 D-21 0.5 8.2 21.2 58.8 Example 13 RD-13 11.3 D-22 0.5 8.2 21.2 58.8 Example 14 RD-14 11.3 D-23 0.5 8.2 21.2 58.8 Example 15 RD-15 11.3 D-24 0.5 8.2 21.2 58.8 Example 16 RD-16 11.3 D-25 0.5 8.2 21.2 58.8 Example 17 RD-17 11.3 D-26 0.5 8.2 21.2 58.8 Example 18 RD-18 11.3 D-27 0.5 8.2 21.2 58.8 Example 19 RD-19 RK-3 11.3 D-19 0.5 8.2 21.2 58.8 Example 20 RD-20 11.3 D-20 0.5 8.2 21.2 58.8 Example 21 RD-21 11.3 D-21 0.5 8.2 21.2 58.8 Example 22 RD-22 11.3 D-22 0.5 8.2 21.2 58.8 Example 23 RD-23 11.3 D-23 0.5 8.2 21.2 58.8 Example 24 RD-24 11.3 D-24 0.5 8.2 21.2 58.8 Example 25 RD-25 11.3 D-25 0.5 8.2 21.2 58.8 Example 26 RD-26 11.3 D-26 0.5 8.2 21.2 58.8 Example 27 RD-27 11.3 D-27 0.5 8.2 21.2 58.8 Comparative Example 1 RD-28 RK-1 11.8 - - 8.2 21.2 58.8 Comparative Example 2 RD-29 RK-2 11.8 - - 8.2 21.2 58.8 Comparative Example 3 RD-30 RK-3 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 27, 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), and the viscosity of the pigment dispersion composition of Examples 1 to 27 was measured at 25 ° C. for 15 days after storage in a low temperature incubator at 25 ° C. And the change in viscosity over time was confirmed. The results were expressed as? (Almost no increase in viscosity),? (Slight increase in viscosity but available range),? (Unusable due to viscosity increase), xx (unusable due to significant viscosity increase).

<Contrast>

The pigment-dispersed compositions of Examples 1 to 27 were spin-coated on a glass substrate of 60 mm x 60 mm in size with a thickness of 0.5 mm so that x = 0.650 (C light source) after curing and dried at 90 占 폚 for 100 seconds After the coated glass substrate was heated at 230 占 폚 for 30 minutes, the dried coating film was irradiated with ultraviolet light with a luminance meter CT-1 (Tsubosaka) and a polarizing plate The contrast value was calculated as the ratio of the luminance in the case of parallelism to the luminance in the case of orthogonalization.

<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 dispaly are indicated by a single 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, 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 mu m and dried at 70 DEG C for 20 minutes. Thereafter, the coated film was heated in an oven at 230 deg. C for 1 hour and then cooled, and the resulting coating film was exposed to light in a L * a * b * color space using a brown light spectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) (L * (1), a * (1), b * (1)). Thereafter, the color difference DELTA Eab * was calculated from the following equation by performing color measurement (L * (2), a * (2), b * (2)) by heating in an oven at 250 deg. And the heat resistance of the coating film was evaluated in the following four stages.

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

&Amp; cir &amp;: DELTA Eab * is less than 1.5

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

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

x: ΔEab * is 5.0 or higher

The results are shown in Table 2 below.

division Pigment dispersion composition Viscosity Contrast Luminance Heat resistance Early 15th Example 1 RD-1 9.7 9.6 7320 19.5 ◎ Example 2 RD-2 9.7 9.7 7380 19.5 ◎ Example 3 RD-3 9.5 9.6 7300 19.4 ○ Example 4 RD-4 9.6 9.4 7390 19.5 ◎ Example 5 RD-5 9.7 9.8 7210 19.5 ◎ Example 6 RD-6 9.4 9.4 7450 19.4 ◎ Example 7 RD-7 9.4 9.4 7470 19.5 ◎ Example 8 RD-8 9.8 9.9 7180 19.5 ◎ Example 9 RD-9 9.5 9.7 7330 19.5 ○ Example 10 RD-10 8.3 8.4 17950 14.8 ◎ Example 11 RD-11 8.4 8.5 17840 14.8 ○ Example 12 RD-12 8.6 8.7 17930 14.9 ◎ Example 13 RD-13 8.5 8.5 17750 14.8 ◎ Example 14 RD-14 8.3 8.2 18060 14.8 ◎ Example 15 RD-15 8.3 8.3 17990 14.8 ◎ Example 16 RD-16 8.7 8.6 17680 14.9 ◎ Example 17 RD-17 8.6 8.5 17870 14.8 ○ Example 18 RD-18 8.4 8.4 17840 14.8 ◎ Example 19 RD-19 7.9 7.8 1570 12.4 ◎ Example 20 RD-20 8.0 7.9 1520 12.4 ◎ Example 21 RD-21 8.1 8.2 1580 12.5 ○ Example 22 RD-22 8.0 8.0 1500 12.5 ◎ Example 23 RD-23 7.8 7.7 1610 12.4 ◎ Example 24 RD-24 8.2 8.0 1580 12.4 ◎ Example 25 RD-25 8.3 8.3 1470 12.4 ◎ Example 26 RD-26 8.2 8.3 1550 12.5 ○ Example 27 RD-27 8.0 7.9 1560 12.4 ○ Comparative Example 1 RD-28 10.8 13.6 6240 19.4 ○ Comparative Example 2 RD-29 10.4 15.1 16320 14.6 △ Comparative Example 3 RD-30 9.8 14.4 1280 12.3 △

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 28]

(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 Japan): 1.5 parts

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

Propylene glycol monomethyl ether acetate (PGMAC): 39.0 parts

[Examples 29 to 54, Comparative Examples 4 to 6]

(Photosensitive coloring composition (RP-2 to 30))

The photosensitive coloring compositions (RP-2 to 30) 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 28 RP-1 RD-1 50.0 7.5 2.0 1.5 39.0 Example 29 RP-2 RD-2 50.0 7.5 2.0 1.5 39.0 Example 30 RP-3 RD-3 50.0 7.5 2.0 1.5 39.0 Example 31 RP-4 RD-4 50.0 7.5 2.0 1.5 39.0 Example 32 RP-5 RD-5 50.0 7.5 2.0 1.5 39.0 Example 33 RP-6 RD-6 50.0 7.5 2.0 1.5 39.0 Example 34 RP-7 RD-7 50.0 7.5 2.0 1.5 39.0 Example 35 RP-8 RD-8 50.0 7.5 2.0 1.5 39.0 Example 36 RP-9 RD-9 50.0 7.5 2.0 1.5 39.0 Example 37 RP-10 RD-10 50.0 7.5 2.0 1.5 39.0 Example 38 RP-11 RD-11 50.0 7.5 2.0 1.5 39.0 Example 39 RP-12 RD-12 50.0 7.5 2.0 1.5 39.0 Example 40 RP-13 RD-13 50.0 7.5 2.0 1.5 39.0 Example 41 RP-14 RD-14 50.0 7.5 2.0 1.5 39.0 Example 42 RP-15 RD-15 50.0 7.5 2.0 1.5 39.0 Example 43 RP-16 RD-16 50.0 7.5 2.0 1.5 39.0 Example 44 RP-17 RD-17 50.0 7.5 2.0 1.5 39.0 Example 45 RP-18 RD-18 50.0 7.5 2.0 1.5 39.0 Example 46 RP-19 RD-19 50.0 7.5 2.0 1.5 39.0 Example 47 RP-20 RD-20 50.0 7.5 2.0 1.5 39.0 Example 48 RP-21 RD-21 50.0 7.5 2.0 1.5 39.0 Example 49 RP-22 RD-22 50.0 7.5 2.0 1.5 39.0 Example 50 RP-23 RD-23 50.0 7.5 2.0 1.5 39.0 Example 51 RP-24 RD-24 50.0 7.5 2.0 1.5 39.0 Example 52 RP-25 RD-25 50.0 7.5 2.0 1.5 39.0 Example 53 RP-26 RD-26 50.0 7.5 2.0 1.5 39.0 Example 54 RP-27 RD-27 50.0 7.5 2.0 1.5 39.0 Comparative Example 4 RP-28 RD-28 50.0 7.5 2.0 1.5 39.0 Comparative Example 5 RP-29 RD-29 50.0 7.5 2.0 1.5 39.0 Comparative Example 6 RP-30 RD-30 50.0 7.5 2.0 1.5 39.0

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

Each composition was evaluated using a pattern formed using the photosensitive coloring compositions of Examples 28 to 54, and the results are shown in Table 4. (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).

<Contrast>

The pigment-dispersed compositions of Examples 28 to 54 were spin-coated on a glass substrate of 60 mm x 60 mm size having a plate thickness of 0.5 mm so that x = 0.650 (C light source) after curing and dried at 90 占 폚 for 100 seconds After the coated glass substrate was heated at 230 占 폚 for 30 minutes, the dried coating film was irradiated with ultraviolet light with a luminance meter CT-1 (Tsubosaka) and a polarizing plate The contrast value was calculated as the ratio of the luminance in the case of parallelism to the luminance in the case of orthogonalization.

<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 dispaly are indicated by a single 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, Brightness, z is the size of the blue component, and BY is the brightness of the blue component).

&Lt; Evaluation of heat resistance &

The coloring composition was applied on the transparent substrate so that the dry coating film was about 1.0 mu m, and dried at 70 DEG C for 20 minutes. Thereafter, the coated film was heated in an oven at 230 deg. C for 1 hour and then cooled, and the resulting coating film was exposed to light in a L * a * b * color space using a brown light spectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) (L * (1), a * (1), b * (1)). Thereafter, the color difference DELTA Eab * was calculated from the following equation by performing color measurement (L * (2), a * (2), b * (2)) by heating in an oven at 250 deg. And the heat resistance of the coating film was evaluated in the following four stages.

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

&Amp; cir &amp;: DELTA Eab * is less than 1.5

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

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

x: ΔEab * is 5.0 or higher

&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 28 RP-1 7460 19.5 ◎ ○ ○ Example 29 RP-2 7520 19.5 ◎ ○ ○ Example 30 RP-3 7470 19.5 ◎ ○ ○ Example 31 RP-4 7510 19.6 ◎ ○ ○ Example 32 RP-5 7410 19.5 ◎ ○ ○ Example 33 RP-6 7620 19.5 ◎ ○ ○ Example 34 RP-7 7640 19.5 ◎ ○ ○ Example 35 RP-8 7340 19.5 ◎ ○ ○ Example 36 RP-9 7520 19.5 ○ ○ ○ Example 37 RP-10 18070 14.8 ◎ ○ ○ Example 38 RP-11 17950 14.8 ○ ○ ○ Example 39 RP-12 18050 14.9 ◎ ○ ○ Example 40 RP-13 17880 14.8 ◎ ○ ○ Example 41 RP-14 18170 14.8 ◎ ○ ○ Example 42 RP-15 18080 14.8 ◎ ○ ○ Example 43 RP-16 17810 14.9 ◎ ○ ○ Example 44 RP-17 17950 14.9 ◎ ○ ○ Example 45 RP-18 17960 14.8 ◎ ○ ○ Example 46 RP-19 1630 12.4 ◎ ○ ○ Example 47 RP-20 1590 12.4 ◎ ○ ○ Example 48 RP-21 1630 12.5 ◎ ○ ○ Example 49 RP-22 1560 12.5 ◎ ○ ○ Example 50 RP-23 1670 12.4 ◎ ○ ○ Example 51 RP-24 1650 12.4 ◎ ○ ○ Example 52 RP-25 1540 12.5 ◎ ○ ○ Example 53 RP-26 1610 12.5 ◎ ○ ○ Example 54 RP-27 1630 12.4 ○ ○ ○ Comparative Example 4 RP-28 6250 19.4 ○ x x Comparative Example 5 RP-29 16370 14.7 △ x x Comparative Example 6 RP-30 1280 12.3 ○ x x

The present invention can improve coloring power by using a pigment derivative in which a dye structure is hybridized. In particular, it has been confirmed that re-solubility is greatly improved by introducing a maleimide group having excellent 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 (11)

1. A pigment derivative represented by the following formula (1).
&Lt; Formula 1 >
Figure pat00042


(Wherein Q represents an organic dye residue,
X 1 is a group selected from - (CH 2 ) n -, -NR'SO 2 -, -SO 2 NR'-, -CONR'-, -CH 2 NR'COCH 2 NR'- and -NR'CO- N is selected within the range of 1 to 10,
X 2 is at least one group selected from an arylene group having up to 20 carbon atoms, a substituted arylene group having up to 20 carbon atoms, a heteroaromatic ring having up to 20 carbon atoms and a substituted heteroaromatic ring having up to 20 carbon atoms or selected from these arylene groups and heteroaromatic rings and -NR'-, -O-, -SO 2 - and -CO- 2 a (divalent) connection (connecting group) refers to at least two groups bonded to each other selected from ,
X 3 represents -NR'-, -NR'SO 2 -, -SO 2 NR'- or -O-,
E is selected from an aryl group having up to 40 carbon atoms, a substituted aryl group having up to 40 carbon atoms, a heteroaromatic ring having up to 40 carbon atoms and a substituted heteroaromatic ring having up to 40 carbon atoms,
R1, R2 and R3 each independently represent a hydrogen atom, a halogen atom, an amine group, a cyano group, a nitro group, an alkyl group having 20 or less carbon atoms, a substituted alkyl group having 20 or less carbon atoms, A substituted or unsubstituted heteroaliphatic ring, an alkenyl group having up to 20 carbon atoms, a substituted alkenyl group having up to 20 carbon atoms, and an aryl group having 20 or fewer carbon atoms, or a substituted Aryl groups,
t is 1 or 2,
Wherein each R 'is independently a hydrogen atom, an alkyl group having up to 20 carbon atoms, a substituted alkyl group having up to 20 carbon atoms, an alkenyl group having up to 20 carbon atoms, a substituted alkane having up to 20 carbon atoms An aryl group having up to 20 carbon atoms, or a substituted aryl group having up to 20 carbon atoms.
The method according to claim 1,
Wherein E in the formula (1) is selected from the following formulas (1A) to (1S).

Figure pat00043

Wherein R 1 is hydrogen, C 1 -C 12 alkyl, C 1 -C 12 hydroxyalkyl, C 1 -C 12 cyanoalkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl,
Y 1 is nitro, cyano, trifluoromethyl, carboxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 acylamino or halogen,
Y 2 and Y 3 are each independently of the other hydrogen, nitro, cyano or halogen,
Y &lt; 4 &gt; is hydrogen, nitro, cyano or halogen,
Y 5 and Y 6 are each independently of the other hydrogen, nitro, cyano or halogen,
Y 7 is chlorine or -CONH 2 ,
Y 8 is chlorine, bromine, C 1 -C 12 alkyl or C 1 -C 12 alkoxy,
Y 9 is cyano, nitro or C 1 -C 12 alkoxycarbonyl,
Y 10 is hydrogen, bromine, chlorine, C 1 -C 12 alkyl, C 5 -C 30 aryl or C 6 -C 36 aralkyl,
Y 11 is hydrogen, cyano, nitro or -COR 1 , wherein R 1 is as defined above,
Y 12 , Y 13 and Y 14 are each independently hydrogen, bromine, chlorine, cyano, nitro or trifluoromethyl.
The method according to claim 1,
A pigment derivative which is any one of compounds represented by the following structural formulas.

The derivative (D-1)
Figure pat00044


The derivative (D-2)
Figure pat00045


The derivative (D-3)
Figure pat00046


The derivative (D-4)
Figure pat00047


The derivative (D-5)
Figure pat00048


The derivative (D-6)
Figure pat00049


The derivative (D-7)
Figure pat00050


The derivative (D-8)
Figure pat00051


The derivative (D-9)
Figure pat00052


The derivative (D-10)
Figure pat00053


The derivative (D-11)
Figure pat00054


The derivative (D-12)
Figure pat00055


The derivative (D-13)
Figure pat00056


The derivative (D-14)
Figure pat00057


The derivative (D-15)
Figure pat00058


The derivative (D-16)
Figure pat00059


The derivative (D-17)
Figure pat00060


The derivative (D-18)
Figure pat00061


The derivative (D-19)
Figure pat00062

The derivative (D-20)
Figure pat00063


The derivative (D-21)
Figure pat00064


The derivative (D-22)
Figure pat00065


The derivative (D-23)
Figure pat00066


The derivative (D-24)
Figure pat00067


The derivative (D-25)
Figure pat00068


The derivative (D-26)
Figure pat00069


The derivative (D-27)
Figure pat00070


The derivative (D-28)
Figure pat00071


The derivative (D-29)
Figure pat00072


The derivative (D-30)
Figure pat00073


The derivative (D-31)
Figure pat00074


The derivative (D-32)
Figure pat00075


The derivative (D-33)
Figure pat00076


The derivative (D-34)
Figure pat00077


The derivative (D-35)
Figure pat00078


The derivative (D-36)
Figure pat00079

 The method according to claim 1,
Wherein the organic pigment residue is selected from anthraquinone, dianthraquinone, diketopyrrolopyrrole, and quinophthalone.
A pigment dispersion composition comprising the pigment derivative according to any one of claims 1 to 4 and an organic pigment.
6. The method of claim 5,
Wherein the organic pigment residue of the pigment derivative is the same as the organic pigment.
6. The method of claim 5,
Wherein the pigment derivative is contained in an amount of 0.05 to 30 parts by weight based on 100 parts by weight of the organic pigment.
6. The method of claim 5,
An organic solvent, and the organic solvent is contained in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the organic pigment.
6. The method of claim 5,
Wherein the viscosity change after 20 days from the initial stage based on the evaluation method of the embodiment is 4 cps or less.
A photosensitive coloring composition comprising the pigment dispersion composition of claim 5 and a photosensitive film forming material.
A color filter comprising a pixel formed by using the photosensitive coloring composition of claim 10.
KR1020130039190A 2013-04-10 2013-04-10 Dye-hybridized pigment derivatives, pigment dispersion composition, photo-sensitive color composition, and color filter KR20140122470A (en)

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