KR20160116988A - Color millbase composition and color filter using the same - Google Patents
Color millbase composition and color filter using the same Download PDFInfo
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- KR20160116988A KR20160116988A KR1020150045508A KR20150045508A KR20160116988A KR 20160116988 A KR20160116988 A KR 20160116988A KR 1020150045508 A KR1020150045508 A KR 1020150045508A KR 20150045508 A KR20150045508 A KR 20150045508A KR 20160116988 A KR20160116988 A KR 20160116988A
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- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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 includes a pigment derivative, an organic pigment, a dispersant and an additive, wherein the additive is selected from the group consisting of a stilbene derivative, an imidazole derivative, a coumarine derivative, a pyrazole derivative, a naphthalimide a quinacridone derivative, and a bisbenzoxazoline derivative. The color mill base composition according to the present invention can be used as a color mill base composition, In addition, it is possible to provide a high-quality color filter excellent in transparency and excellent in color reproducibility.
Description
The present invention relates to a color mill base composition for a color filter of a liquid crystal display and a color filter using the same.
A color filter, which is an optical material for realizing coloring in a liquid crystal display (LCD), disperses three colors of red (R), green (G), and blue (B) A color mill base composition for a color filter is applied to form a colored film and exposed and developed using a photomask to form a desired color 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.
The color mill base, which is one of the constituent materials of LCD, is a key material of color photoresist. It is composed of pigments, dispersants, monomers and solvents so that the particle size of pigments present as macromolecular macromolecules is dispersed to a particle size of 100 nm or less It says.
The color mill base composition for a color filter is required to achieve high sensitivity, high reliability in pattern formation, and high color reproducibility of high transmittance. Accordingly, the pigment concentration of the colored photosensitive resin composition used for manufacturing the color filter is continuously increased, and a colored photosensitive resin composition having the same sensitivity and reliability at a low exposure dose is required to improve the productivity and yield in the process.
An object of the present invention is to provide a color filter having excellent transparency and excellent color reproducibility by adding an additive as a color mill base composition for a color filter of a liquid crystal display.
However, the objects of the present invention are not limited to the above-mentioned objects, and other objects not mentioned can be clearly understood by those skilled in the art from the following description.
The present invention includes a pigment derivative, an organic pigment, a dispersant and an additive, wherein the additive is selected from the group consisting of a stilbene derivative, an imidazole derivative, a coumarine derivative, a pyrazole derivative, a naphthalimide a quinacridone derivative, a naphthalimide derivative, a quinacridone derivative, and a bisbenzoxazoline derivative. The present invention also provides a color mill base composition comprising at least two materials selected from the group consisting of naphthalimide derivatives, quinacridone derivatives and bisbenzoxazoline derivatives.
In the present invention, the additive preferably includes a stilbene derivative, a pyrazole derivative and a naphthalene derivative, and the stilbene derivative is added in an amount of 10 to 80 wt% A pyrazole derivative, and a naphthalimide derivative in an amount of 20 to 90 parts by weight based on the total weight of the composition.
The stilbene derivative of the present invention may be selected from the group consisting of 1,1 '- [(E) -1,2-Ethenediyl] dibenzene, 1,1' - [(E) -1,2-Ethenediyl] dibenzene, Dibenzene, 4,4'-Dihydrazinostilbene-2,2'-disulfonic acid, 2,2'-Diamino-4,4'-stilbenesulfonic acid, Disodium 4,4'- -diamino-2,2'-stilbenedisulfonate. < / RTI >
The pyrazole derivatives of the present invention can be prepared by reacting 4-methyl-1H-pyrazole, 4-methyl-3-phenyl- 1H-pyrazole, and 5-Amino-3-methyl-1-phenylpyrazole.
The present invention also relates to the above naphthalimide derivative, wherein the naphthalimide derivative is 4-amino-1,8-naphthalimide, 1,8-naphthalimide, 4-Amino- N- (2-azidoethyl) -1,8-naphthalimide, N- (2-hydroxyethyl) -1,8-naphthalimide.
The color mill base composition according to the present invention is characterized in that the additive is included in an amount of 1 to 10 parts by weight based on 100 parts by weight of the color mill base composition.
The present invention also provides a color mill base composition, wherein the pigment derivative is a pigment derivative represented by the following formula (1).
[Chemical Formula 1]
[In the above formula (1)
(C1-C30) alkyl, (C1-C30) alkoxy, mono (C1-C30) alkylamino, di Di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;
A or B
(C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (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,
R5 is selected from the group consisting of hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6- (C1-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, R4 may be different or the same;
M is Na, H, K, or Li;
Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of the above R1 to R3; R4 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.
The present invention also relates to the above-mentioned organic pigments, wherein the organic pigments are selected from the group consisting of azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, quinophthalone pigments, Wherein the pigment is at least one selected from the group consisting of a diketopyrrolopyrrole pigment, an anthraquinone pigment, a thioindigo pigment, and a metal complex system pigment.
The present invention also provides a color resist composition comprising the color mill base composition, and a color filter manufactured using the color resist composition.
The present invention can provide a high-quality color filter excellent in transparency and excellent in color reproducibility by adding a dopant to a pigment by adding an additive capable of removing impurities to lower transparency in the color mill base composition.
Also, the color mill base composition according to the present invention can provide a color filter including a dye hybrid pigment derivative and having improved color characteristics such as heat resistance and coloring power.
Before describing the present invention in detail, it is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the invention, which is defined solely by the appended claims. shall. All technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art unless otherwise stated.
Throughout this specification and claims, the word "comprise", "comprises", "comprising" means including a stated article, step or group of articles, and steps, , Step, or group of objects, or a group of steps.
On the contrary, the various embodiments of the present invention can be combined with any other embodiments as long as there is no clear counterpoint. Any feature that is specifically or advantageously indicated as being advantageous may be combined with any other feature or feature that is indicated as being preferred or advantageous. Hereinafter, embodiments of the present invention and effects thereof will be described with reference to the accompanying drawings.
The color mill base composition according to an embodiment of the present invention includes a pigment derivative, an organic pigment, a dispersant, and an additive, and may further optionally include a resin, an organic solvent, and the like.
Each component will be described in detail below.
1. Pigment derivatives
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).
≪ Formula 1 >
[In the above formula (1)
(C1-C30) alkyl, (C1-C30) alkoxy, mono (C1-C30) alkylamino, di Di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;
A or B
(C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (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,
R5 is selected from the group consisting of hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6- (C1-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, R4 may be different or the same;
M is Na, H, K, or Li;
Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of the above R1 to R3; R4 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 color mill base composition according to one embodiment of the present invention, the mixing ratio of the pigment derivative to the organic pigment is preferably 0.05 to 30 parts by weight, more preferably 0.1 to 20 parts by weight, particularly 0.1 To 5 parts by weight. 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.
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
2. Organic 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 and 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.
In particular, in the case of a red color mill base composition, the organic pigments are preferably C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254 and C.I. Pigment Violet < SEP > 19 < SEP >
From the viewpoints of improving the transparency and clarity of the obtained color mill base composition, it is preferable to use an organic pigment having a primary particle size of 100 nm or less or a primary particle diameter of 100 nm or less by an atomization treatment Do. 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 organic pigments described above are surface-modified with the pigment derivative, which means that the pigment derivative is pulverized through milling and dispersion processes such as milling to bind on the surface of the pigment, Can be improved. That is, the pigment derivative forms a coating layer on the surface of the organic 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.
3. 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 organic 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.
4. Additives
The color mill base composition according to an embodiment of the present invention may be used in combination with a stilbene derivative, an imidazole derivative, a coumarine derivative, a pyrazole derivative, a naphthalimide derivative, When a color filter is prepared by using the color mill base composition of the present invention by adding an additive comprising two or more substances selected from the group consisting of a quinacridone derivative and a bisbenzoxazoline derivative, It is possible to provide a high-quality color filter excellent in transparency and color reproducibility.
By providing an additive component according to an embodiment of the present invention, an invisible ray of an ultraviolet ray portion of a sun ray is reflected by a blue ray of a visible portion by a fluorescence function to further reveal whiteness of the color filter, thereby providing a color filter having excellent color reproducibility can do.
The additive preferably includes a stilbene derivative, a pyrazole derivative and a naphthalene derivative. The additive preferably comprises 10 to 80 parts by weight of the stilbene derivative per 100 parts by weight of the additive, , The pyrazole derivative and the naphthalimide derivative in an amount of 20 to 90 parts by weight.
The stilbene derivative may be selected from the group consisting of 1,1 '- [(E) -1,2-Ethenediyl] dibenzene, 1,1' - [(E) -1,2-Ethenediyl] dibenzene, (Z) -1,2-Ethylenediyl dibenzene, 4,4'-Dihydrazinostilbene-2,2'-disulfonic acid, 2,2'-Diamino-4,4'-stilbenesulfonic acid, Disodium 4,4'- But are not limited to, 2,2'-stilbenedisulfonate.
The pyrazole derivative may be at least one selected from the group consisting of 1 H-Pyrazole, 3,5-Dimethyl-1H-pyrazole, 3-Methyl-1H-pyrazole, 5-Amino-3-methyl-1-phenylpyrazole.
The naphthalimide derivative may be selected from the group consisting of 4-Amino-1,8-naphthalimide, 1,8-naphthalimide, 4-Amino- (2-azidoethyl) -1,8-naphthalimide, N- (2-hydroxyethyl) -1,8-naphthalimide.
The additive according to one embodiment of the present invention is preferably contained in an amount of 1 to 10% by weight, particularly 5 to 8% by weight, based on the total weight of the color mill base composition.
In addition, the color mill base composition according to an embodiment of the present invention may further include other conventional additives or additives such as surfactants, fillers, standardizers, antifoaming agents, antidandruff agents, enhancing agents, antistatic agents, preservatives, , Antioxidants and the like as additives.
5. Resin
The color mill base composition may further comprise 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.
6. Organic solvent
The organic solvent used in the color mill base 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 capable of dispersing the pigment particles in the color mill base composition and is not particularly limited, but may be used in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the pigment. If the content of the organic solvent is less than 100 parts by weight, sufficient pigment dispersion 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.
The color mill base composition according to an embodiment of the present invention may be prepared by mixing the organic pigments, the pigment derivatives, additives, and the like by a conventionally known method (for example, Japanese Unexamined Patent Application Publication Nos. 2001-271004 and 2004-91497) . 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 color mill base composition of the present invention can be produced through a wet dispersion stabilization process in which a pigment powder is wetted by mixing the components in an appropriate amount after mixing in an agitator, and the pigment in the composition thus prepared is 20 Lt; RTI ID = 0.0 > 150 nm. ≪ / RTI > 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 color mill base 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 color resist composition containing the color mill base composition of the present invention is used to form a pixel with a known method and structure, a color filter having excellent characteristics is obtained. The color resist composition is obtained by highly dispersing a color mill base composition of the present invention and a photosensitive film forming material in admixture. 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.
Example
Example 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) Lt; RTI ID = 0.0 > 0 C < / RTI > Add Na 2 CO 3 (2M) 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%).
To a flask was added 5-bis ((4-chloro-6- (hexylamino) -1,3,5-triazine-2-yl) amino) -2,4,6-trimethylbenzenesulfonic acid (3 g, 4.4 mmol, 1 eq) (3.7 g, 9.2 mmol, 2.1 eq) and sodium bicarbonate (0.7 g, 8.8 mmol, 2.0 eq) were dissolved in 15 ml of benzene, and then sodium 6 - And the mixture was refluxed at 85 ° C for 24 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure to remove the solvent. After work-up with distilled water (100 ml × 3) , water was removed with MgSO 4 , filtered and dried to obtain a pigment derivative (D-1). (5.1 g, yield 81.9%).
3.1 g of 4,4'-dihydrazinostilbene-2,2'-disulfonic acid, 1.2 g of 1H-pyrazole and 0.7 g of 1,8-naphthalimide were mixed and stirred for 1 hour at a rotation speed of 3,000 rpm using a homogenizer, AD-1).
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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 the completion of the reaction, the solvent was distilled off under reduced pressure to remove the solvent. After work-up with distilled water (100 ml × 3) , water was removed with MgSO 4 , filtered and dried to obtain a pigment derivative (D-2). (5.5 g, yield 79.3%).
6.2 g of 2,2'-diamino-4,4'-stilbenesulfonic acid, 2.2 g of 3,5-Dimethyl-1H-pyrazole and 1.6 g of 4-Amino-1,8-naphthalimide were mixed and stirred using a homogenizer And the mixture was stirred at 3,000 rpm for 1 hour to prepare additive (AD-2).
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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%).
0.2 g of 4-amino-N- (2-propynyl) -1,8-naphthalimide was added to a solution of 0.4 g of 1,1 '- [(E) -1,2-Ethenediyl] dibenzene, 0.4 g of 3-methyl- (AD-3) was prepared by mixing and stirring with a homogenizer at 3,000 rpm for 1 hour.
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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 completion of the reaction, the solvent was distilled off under reduced pressure to remove the solvent. After work-up with distilled water (100 ml × 3) , water was removed with MgSO 4 , filtered and dried to obtain a pigment derivative (D-4). (6.4 g, yield 80.6%).
1.7 g of 4-amino-N- (2-azidoethyl) -1,8-naphthalimide was added to a solution of 1.7 g of 1,1 '- [(E) -1,2- (AD-4) was prepared by mixing and stirring with a homogenizer at 3,000 rpm for 1 hour.
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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- , 80 ml of toluene and 1M-K2CO3 were injected and bubbled with N 2 gas. After raising the temperature to 90 ° C, 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. Add Na 2 CO 3 (2M) to adjust to pH 6 and warm. After 6 hours of reaction, the mixture was worked up with distilled water (100 ml × 3), dried over MgSO 4 , filtered and dried to obtain a pigment derivative (D-5). (5.2 g, yield 79.3%).
3.4 g of N- (2-hydroxyethyl) -1,8-naphthalimide, 3.4 g of 4-methyl-3-phenyl-1H- pyrazole, (AD-5) was prepared by mixing and stirring with a homogenizer at 3,000 rpm for 1 hour.
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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. Add Na 2 CO 3 (2M) to adjust to pH 6 and warm. After 6 hours of reaction, the mixture was filtered with distilled water (100 ml × 3), dried over MgSO 4 , filtered and dried to obtain a pigment derivative (D-6). (3.0 g, yield 82.9%).
0.3 g of 4,4'-Dihydrazinostilbene-2,2'-disulfonic acid, 0.4 g of 5-Amino-3-methyl-1-phenylpyrazole and 0.3 g of 1,8-naphthalimide were mixed and stirred with a homogenizer The mixture was stirred for 1 hour at rpm to prepare additive (AD-6).
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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. Add Na 2 CO 3 (2M) to adjust to pH 6 and warm. After 6 hours of reaction, the mixture is worked up with distilled water (100 ml X3), dried with MgSO 4 to remove water, filtered and dried to obtain a pigment derivative (D-7). (2.9 g, yield 78.5%).
1.5 g of 2,2'-diamino-4,4'-stilbenesulfonic acid, 1.0 g of 1H-pyrazole and 0.5 g of 4-amino-1,8-naphthalimide were mixed and homogenized using a homogenizer at a revolution of 3,000 rpm for 1 hour Followed by stirring to prepare additive (AD-7).
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Example 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. Add Na 2 CO 3 (2M) to adjust to pH 6 and warm. After the reaction for 6 hours, after work-up with distilled water (100 ml X 3), water is removed with MgSO 4 , filtered and dried to obtain a pigment derivative (D-8). (3.4 g, yield 78.4%)
4.0 g of Disodium 4,4'-diamino-2,2'-stilbenedisulfonate, 2.5 g of 3,5-Dimethyl-1H-pyrazole and 1.5 g of 1,8-naphthalimide were mixed and stirred at 3000 rpm using a homogenizer And the mixture was stirred for 1 hour to prepare an additive (AD-8).
The mixture shown in the following Table 1 was stirred and mixed, and 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 color mill base composition having a nonvolatile component of 20% by weight.
Comparative Example 1
Color mill base compositions were prepared in the same manner as the color mill base compositions according to the examples except that the pigment derivatives, organic pigments, dispersants, additives, resins, and organic solvents were changed to the compositions shown in Table 1 below.
RK-1: C.I. Pigment Red 254
DA-1: resinous dispersant solution (SP55000 manufactured by Lubrizol)
AR-1: acrylic resin solution
PGMAC: Propylene glycol monomethyl ether acetate
≪ Production of color filter &
The colored photosensitive resin composition containing the color mill base composition prepared according to Examples 1 to 8 and Comparative Example 1 was coated on a glass substrate by spin coating and then placed on a heating plate and maintained at a temperature of 100 ° C for 3 minutes to form a thin film . Subsequently, a test photomask having a pattern for changing the transmittance from 1 to 100% in a stepwise manner and a line / space pattern from 1 to 50 μm was placed on the thin film, and the distance from the test photomask was set to 300 μm And irradiated with ultraviolet rays. At this time, the ultraviolet light source was irradiated with 1 kw high pressure mercury lamp containing g, h and i lines at an illuminance of 40 mJ / cm 2, and no special optical filter was used. The thin film irradiated with ultraviolet rays was developed in a KOH aqueous solution of pH 12.5 for 80 seconds using a spray developing machine. The glass plate coated with the thin film was washed with distilled water, blown with nitrogen gas, dried, and heated in a 220 ° C heating oven for 20 minutes. The pattern shape (film) thickness of the color filter thus obtained was 1.9 to 2.1 mu m.
Experimental Example
(1) Color characteristic evaluation
The color mill base compositions of Examples 1 to 8 and Comparative Example 1 were coated on a glass substrate by a spin coating method for evaluation of color characteristics, prebaked on a hot plate at 90 DEG C for 3 minutes, And cooled for 1 minute. This was exposed using an exposure machine at an exposure amount of 100 mJ / cm 2 . Then, post-baking was carried out in a convection oven at 230 ° C for 30 minutes. Then, color coordinates and luminance were measured using a MCPD 3000 manufactured by Otsuka electronic Co., Ltd., which is a spectrophotometer, to measure optical characteristics. The results are shown in Table 2 below .
As shown in the following Table 2, it can be confirmed that the color mill base composition according to the present invention according to the present invention exhibits superior spectral characteristics to the color mill base composition according to Comparative Example 1.
(2) Evaluation of contrast
The color mill base 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 and dried at 90 ° C. for 100 seconds The coated glass substrate was heated at 230 占 폚 for 30 minutes, and then the coated film was subjected to ultraviolet exposure using an ultrahigh pressure mercury lamp at a total dose of 60 mJ / cm < 2 > The contrast value is calculated as a ratio of the luminance in the case of the right-handed case and the case of the right-handed case, and is shown in Table 2 below.
(3) Transparency measurement
The color filter was measured for color transparency using a color computer measuring instrument manufactured by SUGAINSTRUMENT. The results are shown in Table 3 in terms of total light transmittance and HAZE.
The features, structures, effects, and the like illustrated in the above-described embodiments can be combined and modified in other embodiments by those skilled in the art to which the embodiments belong. Therefore, it should be understood that the present invention is not limited to these combinations and modifications.
Claims (10)
The additive may be selected from the group consisting of a stilbene derivative, an imidazole derivative, a coumarine derivative, a pyrazole derivative, a naphthalimide derivative, a quinacridone derivative, Wherein the coloring composition comprises at least two materials selected from the group consisting of bisbenzoxazoline derivatives.
The additive necessarily includes a stilbene derivative, a pyrazole derivative, and a naphthalene derivative,
Wherein the stilbene derivative is contained in an amount of 10 to 80 parts by weight and the pyrazole derivative and the naphthalimide derivative are contained in an amount of 20 to 90 parts by weight based on 100 parts by weight of the additive. Mill base composition.
The stilbene derivative may be selected from the group consisting of 1,1 '- [(E) -1,2-Ethenediyl] dibenzene, 1,1' - [(E) -1,2-Ethenediyl] dibenzene, (Z) -1,2-Ethylenediyl dibenzene, 4,4'-Dihydrazinostilbene-2,2'-disulfonic acid, 2,2'-Diamino-4,4'-stilbenesulfonic acid, Disodium 4,4'- 2,2'-stilbenedisulfonate. ≪ / RTI >
The pyrazole derivative may be at least one selected from the group consisting of 1 H-Pyrazole, 3,5-Dimethyl-1H-pyrazole, 3-Methyl-1H-pyrazole, 5-Amino-3-methyl-1-phenylpyrazole.
The naphthalimide derivative may be selected from the group consisting of 4-Amino-1,8-naphthalimide, 1,8-naphthalimide, 4-Amino- (2-azidoethyl) -1,8-naphthalimide, N- (2-hydroxyethyl) -1,8-naphthalimide.
Wherein the additive is included in an amount of 1 to 10 parts by weight based on 100 parts by weight of the color mill base composition.
Wherein the pigment derivative is a pigment derivative represented by the following formula (1).
[Chemical Formula 1]
[In the above formula (1)
(C1-C30) alkyl, (C1-C30) alkoxy, mono (C1-C30) alkylamino, di Di (C6-C30) arylamino, hydroxy, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro;
A or B
(C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (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,
R5 is selected from the group consisting of hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C6- (C1-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, R4 may be different or the same;
M is Na, H, K, or Li;
Alkyl, alkoxy, monoalkylamino, dialkylamino, monoarylamino and diarylamino of the above R1 to R3; R4 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.
The organic pigment may be at least one selected from the group consisting of azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, quinophthalone pigments, Anthraquinone pigments, thioindigo pigments, and metal complex system pigments. The color mill base composition of claim 1,
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